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Rob Walling has invested in 211 SaaS companies, runs MicroConf, and sold Drip in 2016 without ever taking venture money. His 1-9-90 rule says only 1% of startups should raise VC — and that the rest of us have been brainwashed by what he calls the venture industrial complex. He includes himself in the brainwashed.

Rob Walling is saying no, and he is not saying it once. He lines the noes up, one after another, the way you wave off a stack of bad ideas being slid across a table at you.

“It’s like, no, no, no, no, no,” he says.

What he is refusing is a story. The story goes like this: you have an idea for a software company, so you raise money, and you try to become Uber, and then you try to become Facebook, and if you do not clear that bar you have failed. Rob has spent twenty-five years and six companies demonstrating that the story is optional, and he still cannot quite get over how many people accept it as physics.

“This bullshit narrative,” he calls it, “that everybody who does a startup has to raise funding. It’s just not true.”

He has a rule for this. He says it the way a man says a thing he has said on a hundred podcasts and still means. Of all the software startups that get born into the world, he figures about one percent should even consider raising venture capital. About nine percent should consider some other kind of funding — friends and family, an angel round, the non-venture money he runs an accelerator to provide. And the rest, the ninety percent, should bootstrap. One, nine, ninety. He can recite it in his sleep.

The number that stops me is not the ninety. It is the one.

Because I have spent my whole adult life inside an industry that behaves as if the number is closer to a hundred. I have watched roadmaps get bent toward whatever story raises the next round. I have watched a marketplace feature get greenlit not because customers wanted it but because marketplaces carry higher valuations. And I got, as I tell Rob somewhere in the middle of our conversation, red-pilled on the whole thing when all of my friends got laid off at once. I got lucky. I kept my job. But I watched a year of other people’s lives get spent chasing a valuation multiple, and I could not un-see it after that.

Rob has a longer version of the same disillusionment, and he dates it precisely.

“The venture industrial complex has brainwashed us all,” he says. “Me included, back in the early 2000s.”

That last clause is the one I keep turning over. He does not exempt himself. He is not standing outside the machine describing it to me from a clean distance — he is a former believer, someone who once assumed, like everyone around him, that the only way to build something real was to raise buckets of money and swing for a decacorn. The 1-9-90 rule is not a theory he arrived at in a business-school seminar. It is the shape of a mind that changed.

Here is the part the venture story cannot account for, the part Rob keeps returning to. There are, by his count, fifty or sixty thousand B2B SaaS companies in the world doing real revenue. Boring ones. Companies that started as an email tool or an invoicing utility or a scheduling widget and grew into businesses that pay their founders extremely well. None of them will ever be written about. None of them will trend. They are, he says, and this is the image I cannot shake afterward, like an iceberg under the water.

“If folks go to tinyseed.com slash portfolio,” he tells me, “they can see, I don’t know, there’s like boring B2B SaaS businesses that I’ve invested in. And it just gives you an idea of the types of things, the niches you can be in.”

The tip of the iceberg is the part everyone sees. The Ubers. The Facebooks. The companies that raise enough money to buy the attention. What Rob spends his days doing — through TinySeed, the accelerator he built for exactly these founders, and MicroConf, the conference he has run for the bootstrapped crowd for over a decade — is funding the part underwater. The mass of it. The businesses that do not photograph well.

Drip was one of them. It is the proof he reaches for when I ask him to make the abstract concrete, and it is worth sitting inside the story for a moment, because it is the whole argument in miniature. In 2012 Rob wanted a small email-capture widget for websites. He and his co-founder Derek Reimer built it. It did not take off. It took fourteen months of grinding — nine of them after the public launch — to reach what Rob considers strong product-market fit, and even that came only after he made a hard call on incomplete information and turned an email tool into a marketing automation platform.

What made it work was not a war chest. It was a gap. On one side sat the cheap, dumb email tools — MailChimp, AWeber, Constant Contact — none of which could automate anything. On the other side sat the expensive marketing automation platforms, the Marketos and Infusionsofts, with their four-hundred-dollars-a-month floors and their two-thousand-dollar onboardings and their annual commits. In between was a whole population of people who just wanted to pay fifty or a hundred bucks a month and not talk to a salesperson. Drip slid into that middle. No venture money required. Just a founder who had been listening long enough to hear the gap that nobody was filling.

“It wasn’t luck,” Rob says, and then, because he is honest, he immediately complicates it. “I also happened to see the gap.”

We spend a while on luck, because Rob refuses to pretend it did not matter and equally refuses to let it become the whole explanation. His framing is the cleanest I have heard. Luck, he says, is a multiplier. Not a cause — a multiplier. It scales whatever you have already built. He points at Basecamp, at Jason Fried and DHH, whom he once asked directly why the company succeeded. Their answer was luck and timing, one and two. But Rob does the arithmetic underneath the modesty. Basecamp is doing, he guesses, somewhere north of a hundred million a year. Strip the luck out entirely and you are still looking at a ten- or twenty-million-dollar business.

“It’d still be a great fucking business,” he says.

That is the sentence the venture narrative has no slot for. A great business that is merely great. A ten-million-dollar-a-year company that will never be a headline and will make its founders wealthy and free for the rest of their lives. Rob mentions, almost in passing, DHH describing how he and Fried simply split four million dollars off the bottom line at the end of a year — the kind of number you do not get to keep at a venture-backed startup, where the money belongs to the next round before it ever reaches you.

The whole time we talk, I keep thinking about opportunity cost, because that is what the venture story actually costs the ninety percent who buy it. Not just the companies that raise and fail. The ones that raise and, in doing so, agree to chase a size they never needed, on someone else’s timeline, until the thing that could have been a wonderful ten-million-dollar business gets managed into the ground reaching for a hundred. You can pull profit out of a bootstrapped company every year it exists. You can sell it someday if you want. Either way it belongs to you, and the decisions belong to you, and nobody in a board meeting gets to bend your roadmap toward a multiple.

Rob is not anti-ambition. This is the thing people miss about him. He wanted, badly, to build a multimillion-dollar business, and he did it more than once. He is anti-VC-narrative. He is against the single story that got installed in all of us — him first, back in the early 2000s — that says the raise is the beginning of the journey and the size of the raise is the measure of the ambition.

Near the end I find myself thinking about the founders he funds. The ones building something niche and unglamorous, the invoicing tool, the scheduling widget, the boring vertical SaaS nobody will ever cover. They are not failing to be Uber. They were never trying to be Uber. They are down under the surface where most of the actual water is, building businesses that will quietly make them free, and the only reason it looks like nothing is happening down there is that the part of the ocean we photograph is the tip.

Rob spends his life pointing at the water under the tip. Ninety percent of it, by his count.

Guest Bio: Rob Walling

Rob Walling is the Co-Founder of TinySeed, a year-long remote accelerator for bootstrapped and non-unicorn SaaS founders, and the Founder of MicroConf, the original community for self-funded software entrepreneurs. Rising to prominence in the mid-2000s through prolific writing and podcasting, he became one of the most recognized voices in the bootstrapped SaaS movement — widely regarded as the practical counterpoint to the venture-capital-centric startup narrative.

Previously, he co-founded Drip, an email marketing and automation platform, in 2012. Alongside co-founder Derek Reimer, he bootstrapped Drip from a small email capture utility to a full marketing automation suite, achieving strong product–market fit after 14 months of grinding and eventually reaching millions in annual recurring revenue. Drip was acquired by Leadpages in 2016, the liquidity event Rob has described as his “never have to work again” moment. Through TinySeed, which he founded with Einar Vollset, he has since funded more than 200 SaaS companies, with a reported millionaire rate of 43% across the portfolio.

His earlier career included developer-for-hire roles at a credit card company, a startup, and a consulting firm in the early 2000s, followed by a stint as a real estate investor (four properties, seven units in Los Angeles) before fully committing to bootstrapped software. His first small software win, NET Invoice — invoicing software that generated $2,000–$4,000 per month — proved the model was viable without outside funding.

As host of Startups for the Rest of Us, a weekly podcast he has published without interruption since 2010, Rob has shipped over 738 episodes and accumulated more than 15 million downloads. He is also the author of Start Small, Stay Small (2010), a foundational text for developer-entrepreneurs, and The SaaS Playbook (2023).

Hey,

Thanks for reading this. I mean that. There’s a lot of content out there competing for your attention, and you spent some of it here. I hope it was worth it. Even better, I hope it prompted you to think about something differently enough that you’d share it with someone who’d get something out of it too.

I started this podcast because tactics never stuck with me. What stuck were stories — business biographies, autobiographies, the decisions people made and why they made them. The principle only clicks once you know the story behind it.

So I built the thing I wanted to listen to. Every week I have two conversations with people who build in technology and product. Then I write the essay in my premium newsletter (Taste Maker) to distill the principles and reflect on the narrative — one that puts you inside the conversation, through my eyes. What caught me off guard. What I kept thinking about after we hung up. Where the principle actually lives once you strip away the jargon.

I make this for myself first. If you read the way I do, you’ll want it too.

PS — If you want to pitch coming on the show, or you know someone I should talk to, shoot me an email at caden@hey.com with "January752" in the subject line so it gets past my filters. I'm not optimizing for famous guests. I'm optimizing for interesting conversations, even from people who aren't LinkedIn influencers.

Listen to this episode on Spotify or Apple Podcasts

Marcelo Calbucci is describing a product manager who has done everything right, and who is about to make a mistake.

The setup is mundane on purpose. The customer wants tags. They’ve asked for tags. Ten support tickets came in this month asking for the same thing — the ability to label their files, their emails, organize them their own way. The product manager pulls the tickets together and walks into the leadership meeting with a clean story. This is important. Lots of people are asking for it. Here is the evidence.

“And you go to the leadership,” Marcelo says, half-acting the part, “and it’s like, this is so important. Lots of people are asking for it.”

He lets the picture hang there for a second, because the picture is the trap.

“The real question is like, wait a second. Why are they trying to do that? What exactly are they trying to do?”

I’ve watched a lot of product people walk into that exact meeting. I’ve been in the room for the version where the tickets win and the team ships the tags and nobody asks the second question. So I want to know what Marcelo thinks the second question reveals. He answers with the rest of the story.

“Maybe what they need is a consolidated list at the end of the month, because they have to provide a report to someone.” He pulls the thread one more turn. “And you’ll be like, wait a second. You don’t need tagging to do that.”

Marcelo Calbucci is the author of The PRFAQ Framework, the book he published in January 2025 adapting Amazon’s Working Backwards process for people who don’t have Amazon’s resources behind them. He has the résumé to make the claim land: roughly seven years at Microsoft, where he led engineering at Bing; about two years at Amazon, on a product and engineering team inside the HR organization, watching the PRFAQ machine run at full scale; six startups co-founded across Seattle and London over 18 years; more than $40 million raised across them. He wrote his first software at 12 and sold a CRM tool for MS-DOS at 16. We’re on a video call in late February, the book just out, and I’ve steered us toward the question everyone is asking him: where does AI fit in a methodology that is fundamentally about writing?

His answer is not the answer I expected from someone whose whole brand is a writing framework. It’s more useful than that. It’s a line — a border he draws straight down the middle of all the writing a person does at work, with the model on one side and the human alone on the other.

On one side: the tactical. The résumé. The pattern-based document where the shape is already known and ten thousand good examples already exist in the world. “If you’re doing things that are more tactical,” he says, “you need to write your own résumé — it doesn’t require a lot of strategy there.” Hand it to the model. It has seen more résumés than you ever will. The same goes, he says, for the tagging feature, once you’ve established that tagging is actually what’s needed. “Oh, let me research all the ten ways there are to do tagging, all the examples, all the patterns.” That is exactly the work a language model is built to do. “You’re not gonna create that much value by doing the work yourself. So you might as well leverage the LLM.”

On the other side: the strategic. And here his voice changes — not louder, just firmer, the way someone gets when they’re saying the part they actually care about.

“When you ask ChatGPT, like, create a business plan, or create a strategy for an app, or for a website, or for a podcast, whatever — you are telling AI, do the thinking for me, and just gimme the results. You are losing so much by doing that.”

I ask him to be precise about what’s being lost, because “losing so much” could mean the output is worse, and that’s not quite his claim.

It’s not about whether the idea is good, he tells me. It’s that your brain was never engaged. The plan arrives fully formed, and you skipped the part where producing it forced you to confront what you didn’t know. “The writing helps you think about what you don’t know,” he says, “and forces you to do some research to come back and finish the writing.” The model removes that friction. It does the research and the writing in one motion, and hands you a document you never had to struggle toward — which means you never found the holes, because finding the holes was the struggle.

This is the inversion at the center of how he thinks, and it took me the back half of our conversation to see how completely it reorganizes the AI question. Most people frame AI writing as a quality problem: is the output good enough? Marcelo frames it as an engagement problem. The output might be excellent. That’s not the point. The point is what happens — or doesn’t — inside the head of the person who was supposed to do the thinking.

Which is why the tagging story matters so much to him, and why he keeps the two halves of it apart. There’s the question of whether to build tagging — strategic, the kind of thing where the writing has to surface the real customer problem hiding under the stated one. And there’s the question of how to build tagging well once you’ve decided it’s right — tactical, ten patterns, hand it to the model. The PRFAQ is for the first. A PRD, the product requirements document engineers actually build from, is for the second. And the failure mode he sees everywhere is people running an LLM over the first kind of question, generating a confident plan for the wrong feature, and never noticing because the document looked so finished.

“It is very rare,” he tells me, “when you should use an LLM for most requirement docs.” He says it almost as a correction to himself, mid-thought, as if he’s surprised by how far the principle extends once he follows it honestly. The more strategic the document, the less the model should touch the core of it.

He’s careful, though, not to turn this into a prohibition. He uses AI. He’s emphatic that you can hand the model your assumptions and ask it to argue against them, ask it to surface the questions you haven’t thought of, ask it to brainstorm. “Not that you can’t use ChatGPT to ask questions and help you brainstorm certain things,” he says. “But you want to do the core of the thinking.” The model is allowed in the room. It just doesn’t get to be the one who decides what the room is for.

There’s a version of this distinction that sounds like a productivity tip — use AI for the boring stuff, do the important stuff yourself. But the longer he talks, the clearer it gets that he’s describing something closer to a discipline, and the discipline is harder than it sounds, because the model is so good and so fast that refusing it requires you to choose friction on purpose.

He gives me the harder case, the one where the line gets blurry. A premium feature — something behind a paywall, something that decides whether a user upgrades or churns. On the surface it’s just a feature, the same as tagging. But the questions underneath it are strategic ones. Are we going to lose users who feel this should be free? Where does it sit in the plan? “That is very strategical,” he says. “Because now we are talking about, hey, are we gonna lose users if they don’t pay?” His ruling: that one should have been a PRFAQ before it was ever a PRD. You do the strategic writing first — by hand, with the blank page, finding the holes — and only then do you let the model help you execute.

The work, in other words, is knowing which kind of writing you’re doing before you reach for the tool. And the temptation runs entirely one direction. Nobody is tempted to hand-write their résumé from scratch for the joy of the struggle. The temptation is always to let the model take the strategic document too, because it can, and because the result looks just as polished, and because the polish hides the fact that no one did the thinking.

I tell him this is starting to sound less like advice about AI and more like advice about character — the willingness to do the slow version when a fast version is sitting right there, indistinguishable from the outside. He doesn’t disagree. He reframes it in the language he uses for everything else.

“You’re moving from a bias to action,” he says, “to a bias to impact.”

That phrase had come up earlier in our conversation, aimed at a different target — the product manager who measures himself by how much he ships. But it lands differently here, pointed at the AI question. Bias to action is what a language model is perfectly built to serve. It will produce, instantly, on demand, a plan, a strategy, a business case, as much as you want, as fast as you can ask. It is the most powerful bias-to-action engine ever made. And that, in Marcelo’s telling, is exactly the danger. The thing that makes it irresistible is the thing that lets you skip the only part that mattered.

I keep coming back to that product manager from the start, the one with the ten tickets and the clean story. He didn’t do anything lazy. He gathered evidence, he found a pattern, he built a case. In a bias-to-action world he is a model employee. He shipped. And he shipped the wrong thing, because the writing he needed to do — the slow, strategic kind that would have forced him to ask what the customer was actually trying to accomplish — was precisely the kind a tool could have done for him in 30 seconds, leaving the real question unasked.

The tags would have worked. The feature would have shipped. The tickets would have closed. And somewhere a customer would still be exporting their tagged files by hand at the end of every month, building the report they needed all along, wondering why the thing they asked for didn’t give them the thing they wanted.

That was never the easy part. It only looked easy because a machine could do it.

Guest Bio: Marcelo Calbucci

Marcelo Calbucci is the author of The PRFAQ Framework, a six-time founder, and a seasoned CPO/CTO with 25 years in technology spanning Microsoft, Amazon, and 18 years of startup building across Seattle and London. Rising to prominence in the Seattle startup ecosystem through the 2000s and 2010s, he became known for translating enterprise innovation practices into frameworks accessible to founders and product leaders at any stage — culminating in his 2025 book adapting Amazon’s Working Backwards process for organizations of all sizes.

Previously, as a product and engineering leader at Amazon, Calbucci led a team inside the company’s HR organization, an experience that gave him a firsthand view of the PRFAQ process operating at full scale — with months-long document cycles, financial modeling, and cross-functional research teams backing major bets. Before Amazon, he spent approximately seven years at Microsoft, where he led engineering at Bing, then left to pursue 18 years of entrepreneurship, raising more than $40M across multiple startup ventures and studios in Seattle and London.

Earlier in his career, he helped build foundational institutions in the Seattle tech community, including what became the GeekWire Awards and the GeekWire 200. He currently organizes the Acquired Seattle meetup and Seattle Flow, two communities for operators and founders in the Pacific Northwest.

As the author of The PRFAQ Framework, Calbucci distills the Working Backwards methodology into a one-to-two-week process for individual contributors, startup founders, and executives who lack Amazon’s organizational infrastructure — arguing that the framework’s real value is teaching innovators to think critically about whether an idea is worth building at all.

Hey,

Thanks for reading this. I mean that. There’s a lot of content out there competing for your attention, and you spent some of it here. I hope it was worth it. Even better, I hope it prompted you to think about something differently enough that you’d share it with someone who’d get something out of it too.

I started this podcast because tactics never stuck with me. What stuck were stories — business biographies, autobiographies, the decisions people made and why they made them. The principle only clicks once you know the story behind it.

So I built the thing I wanted to listen to. Every week I have two conversations with people who build in technology and product. Then I write the essay in my premium newsletter (Taste Maker) to distill the principles and reflect on the narrative — one that puts you inside the conversation, through my eyes. What caught me off guard. What I kept thinking about after we hung up. Where the principle actually lives once you strip away the jargon.

I make this for myself first. If you read the way I do, you’ll want it too.

PS — If you want to pitch coming on the show, or you know someone I should talk to, shoot me an email at caden@hey.com with "January752" in the subject line so it gets past my filters. I'm not optimizing for famous guests. I'm optimizing for interesting conversations, even from people who aren't LinkedIn influencers.

Listen to this episode on Spotify or Apple Podcasts

Ashley Jablow spent a year inside the EPA’s Office of Pesticide Programs as a Presidential Innovation Fellow, watching paper files travel by hand and by email between people who couldn’t share a building. The innovation she remembers most clearly wasn’t a system overhaul or a policy rewrite. It was a woman at a desk who figured out she could sign a PDF and stop printing it.

Ashley Jablow is somewhere inside the Environmental Protection Agency, in the Office of Pesticide Programs, doing the unglamorous version of her job. She is running research interviews. She is asking the people who actually review the safety and efficacy of the pesticides that get used on the country’s food supply how their work moves from one person to the next. The answer, she finds, is paper. Hundreds of pages of paper. A reviewer signs a file, scans it, emails it, and the next person prints it, signs it, scans it, and sends it on. The buildings are spread out. The people inside them are dedicated. The system runs on toner.

One afternoon a woman at one of the desks calls Ashley over.

“Ashley, I wanna show you something that I’ve figured out,” the woman says.

“Please, show me what — show me your work,” Ashley says back.

“This is what I’ve figured out,” the woman says. “Instead of printing each file every time I receive it, I have figured out how to put my digital signature, my electronic signature, on this PDF, so that I don’t have to print out hundreds of pages.”

Ashley admits, when she tells me this, that her first reaction was not the right one.

“I was like, yeah, like, what’s so exciting about that?” she says. “Doesn’t everybody know how to annotate a PDF?”

I want to sit with her admission for a second, because it is the thing the essay is about. Ashley Jablow came to the EPA from IDEO. She had already spent years inside a design and innovation company so famous for its method that the word design lost a syllable when consultants said it. She had then helped run Open IDEO, the open-innovation startup that crowdsourced design challenges for social and environmental impact — a niche inside a niche inside a niche, which she could feel narrowing around her. Six weeks after she got the call accepting her to the Presidential Innovation Fellows program, she had moved her husband and her fifteen-month-old son from San Francisco to the East Coast and reported for a one-year tour of duty inside a federal agency. The fellowship was supposed to broaden her aperture. It did. She has lived in Virginia for over a decade now.

And there she was, standing over the shoulder of a public servant, looking at an annotated PDF, thinking: that’s it?

The honest answer is yes. That’s it.

She tells me what she had to unlearn to see it. At IDEO, the pace was such that she used to fantasize about a single pill that would give her every nutrient she needed at lunchtime so she would not have to stop working. Moving into government, she says, felt like stepping off the moving walkway at the airport — the involuntary lurch forward, the sense that something underneath you had stopped without warning, the long recalibrating look around. How are we ever going to get anything done at this pace? she remembers thinking.

The other thing she had to unlearn was the front page. In the private sector, the front page of the newspaper is the prize — let’s have some wins, let’s share them, let’s blow up our launch metrics in public. Inside the government, the front page is the failure condition. If you are on it, something has gone wrong with public money. She names it without preamble: in the public sector, the goal is to avoid being on the front page, and that is the gravitational field every person around her was working inside. Conservatism is not a personality trait there. It is the structure of the building.

I’m not going to flatten this into a clean Silicon-Valley-bad, government-good fable, because Ashley does not, and the woman at the desk would not. The point of the digital signature is not that government is virtuous. The point is that, inside that incentive structure, the innovation that survived was the one she could prove was harmless. No press release. No keynote. A reviewer figured out that the Sign tool in Acrobat existed, and the cascade of printers downstream went quiet by however much paper one workflow accounted for. The frontier of innovation, for that office, was an annotation menu nobody had bothered to open.

I ask Ashley to tell me what the word innovation even means to her after a year of looking at things like that, and she goes to the Latin.

“The Latin root of the word innovation means change,” she says. “Means to begin again, to renew.”

Then, almost as an afterthought: change is actually everywhere. It’s a constant. The seasons change. Babies learn to walk. We get older. Change is quite neutral when you think about it out in nature. Innovation, on her reading, is a fancy borrowed word for the most ordinary thing in the world. It is not novelty. It is not flash. It is not the front page. It is the act, performed honestly inside a constraint, of beginning again.

This is where I have to disclose something, because the essay would be dishonest without it. I’d spent the first part of our call indulging a long tangent about K-Pop Demon Hunters — the way the animation studio behind Spider-Verse sweated the pre-production until the story landed; the way Sony quietly sold the film to Netflix for a fraction of what it later earned; the way Ted Sarandos called it Netflix’s Frozen. I was using it as a stand-in for stewardship. Care about the narrative, I was saying, and the audience shows up. Skip the narrative, green-light the IP because you bought it, and the audience does not. Ashley listened. She let me finish. And then she did something that was, in retrospect, the entire move of the conversation: she pulled the example back to the EPA woman. The studio in Los Angeles and the reviewer at the EPA were doing the same thing, just on different stages. They were performing the unglamorous work and not skipping it.

It struck me, late, that the reason her example was easier to dismiss than mine was that hers did not flatter the listener. There is no founder myth at the end of a digital signature. There is no Netflix chart. There is only the next file, signed without printing, passed to the next person. The cost compounds invisibly. The savings compounds invisibly. The work is the same.

This is the part where, on most podcast calls, the guest would pivot to a framework. Ashley does not. She tells me, instead, about being an imposter at IDEO. I remember spending my time at IDEO honestly like such an imposter, she says — there was so much to learn, there was a lot of jargon, there was a kind of black box process she was trying to learn on the job. She left, did the EPA year, and only then, metabolizing what she had learned, came to the realization that it was quite simple. There was, she says, an awful lot of peacocking around the word. Shiny and bright and innovation, this hallowed space. The reality was always more ordinary: figure out what people want, what they will use, what they’re struggling with. Imagine some possibilities. Try the smallest, fastest, cheapest thing you can try right now to learn the most.

It is not rocket science. It is not brain surgery.

The way she puts the prototype piece is the line I keep replaying. One of the leaders at IDEO, when she was still there, told her that a prototype is a prop that tells a story. The prop is what you bring to a research session to ask: how do you think you might use this? Where do you see it breaking? Tell me the story of that. The digital signature, in that frame, was already a prototype. The reviewer at the EPA was already a designer. She just had not been peacocked at long enough to know what to call herself.

Late in the call I make the mistake — the useful kind — of asking Ashley how she would coach somebody whose candor cuts the people around them. I am thinking, when I ask, about Steve Jobs in his exile years. I am also thinking, transparently, about myself, because I have been candid to the point of making people feel small, and I have not entirely figured out how to stop. Ashley does not answer the question I asked. She answers a better one.

She turns the lens on the relationship.

Let’s say I have a value of predictability, she says. I like structure, I like order, I like a plan. And let’s say, Caden, you have a value of spontaneity, the creative process, that aha moment.

Neither of those values is right or wrong. Neither is the smart one. We are assigned to work on a project together. We have six weeks. She is going to walk into the first meeting and say: what is our plan, what is our schedule, what are our midpoints? I am going to walk into that meeting and say: I need some openness, some time and space, to let it come to me. We are going to have conflict, she says, not because either of us is unprofessional but because we are approaching the same problem from different values, and we have forgotten to name the values out loud.

I should be clear about what just happened. She was not running an exercise. She was reading me. I do not like giving estimates I have not earned the right to give. I do, in fact, ask for two weeks of exploration before I will commit to a number. I do, in fact, lurch when the calendar is the only thing in the room. She named my actual operating system using the example, and she did it without making me feel small.

This, I realize later, was the actual demonstration of the coaching skill she had just been describing. The hardest part of learning to lead, she quotes the coach Jerry Colonna, is learning to lead yourself. She does not say it about me. She says it about Steve Jobs. But she put it in the air between us, and then she modeled the same thing she was naming. The being and the doing. How you show up next to a person, before you ask the person to do anything.

Soft skills, the cliché says, are the soft stuff. Hard results are the hard stuff. Ashley spent the call quietly inverting that. The reason a P&L lands at the end of a quarter is that, six weeks earlier, two people with different values walked into the same room and agreed on how to work together. The reason a pesticide review actually moves through the building is that a reviewer at a desk decides, on her own, to stop printing. The reason a film is good is that someone sweated the script while the calendar said ship.

The work, in every one of those frames, is the same. It is small. It is specific. It is operational. It is the thing you can do today inside the constraint you are inside. You can call it innovation if you like. The Latin word means to begin again, which is what the woman at the EPA was doing, file by file, while the front page elsewhere belonged to the people who did not have to.

I think about her, after the call. The reviewer Ashley still remembers. Whoever she is, she is presumably still at her desk somewhere, signing pesticide files. She is not on the front page. The work, by definition, has not been on the front page. Pages that did not need to be printed do not show up in any news cycle.

They show up, instead, in the absence of themselves. In a printer that did not run. In a toner cartridge that did not get replaced. In a paragraph at the end of a podcast about a woman whose name nobody learned, whose change everybody benefits from, whose innovation Ashley Jablow can still describe twelve years later as the one that mattered.

That is the front page Ashley spent a year learning to read.

Guest Bio: Ashley Jablow

Ashley Jablow is the Founder and Principal of Wayfinders Collective and creator of Life Design School, a creative studio dedicated to helping leaders and professionals redesign their work and lives with human-centered intention. Rising to prominence in the 2010s through her work at the intersection of design thinking, civic innovation, and leadership development, she became known for translating the methods of the world’s leading design consultancies into practical frameworks for individuals and organizations navigating change. Since founding Wayfinders Collective in 2017, she has accumulated 500-plus hours of coach training through the Coaches Training Institute and built a practice spanning executive coaching, organizational facilitation, and on-demand learning resources.

Previously, as a Presidential Innovation Fellow in the Obama Administration, she embedded with federal agencies to bring human-centered design methods into government — most notably at the Environmental Protection Agency, where she studied workflow bottlenecks in the Office of Pesticide Programs, and at the National Archives, where she led open design of technology for citizen access to historical records. The fellowship, originally a one-year commitment, permanently relocated her family from San Francisco to Virginia. She subsequently served as Vice President of Development & Impact at Vizzuality, a Spanish data visualization and design firm, where she was their first U.S. hire and launched the company’s inaugural American office.

Earlier in her career, she joined IDEO as the first full-time hire on the OpenIDEO platform, a global crowdsourcing initiative running online design challenges for social and environmental impact. She holds a BA in Sociology and Spanish from the University of Michigan and an MBA in Marketing and Corporate Responsibility from Boston University.

As creator of The Clarity Kit, a free 30-minute on-demand workshop available at lifedesignschool.co, she helps participants identify the core problem they need to solve before entering solution mode — applying the same diagnostic rigor she developed across IDEO, government, and consulting to the challenge of personal reinvention.

Hey,

Thanks for reading this. I mean that. There’s a lot of content out there competing for your attention, and you spent some of it here. I hope it was worth it. Even better, I hope it prompted you to think about something differently enough that you’d share it with someone who’d get something out of it too.

I started this podcast because tactics never stuck with me. What stuck were stories — business biographies, autobiographies, the decisions people made and why they made them. The principle only clicks once you know the story behind it.

So I built the thing I wanted to listen to. Every week I have two conversations with people who build in technology and product. Then I write the essay in my premium newsletter (Taste Maker) to distill the principles and reflect on the narrative — one that puts you inside the conversation, through my eyes. What caught me off guard. What I kept thinking about after we hung up. Where the principle actually lives once you strip away the jargon.

I make this for myself first. If you read the way I do, you’ll want it too.

PS — If you want to pitch coming on the show, or you know someone I should talk to, shoot me an email at caden@hey.com with "January752" in the subject line so it gets past my filters. I'm not optimizing for famous guests. I'm optimizing for interesting conversations, even from people who aren't LinkedIn influencers.

Listen to this episode on Spotify or Apple Podcasts

They removed the timer from a recording app. They added balloons, then quadrupled her rate from $400 a month to $1,800. Molly walked — and used the story to explain something I’ve been circling for years: most product roadmaps are written for the board, not the customer.

Molly is twenty minutes into a story about a phone call she had with Riverside, the video-recording software her podcast agency was using to record clients. She is not laughing. She is doing the slightly-controlled-anger voice of someone who has had to say the same obvious thing in three different meetings.

“You are killing my cost, man,” she tells me she told them. “You are killing my cost of goods sold.”

She is in Costa Rica. I am in Utah. There is a kind of dry, transactional warmth in how she lays it out, the way someone who runs an actual business talks about a vendor who doesn’t run one. Molly owns Heartcast Media — twenty-five years in multimedia, the company that produces over a thousand podcast episodes for clients who include the Department of Health, NATO, and a long list of CEOs who hire her specifically so that they don’t have to think about microphones. She knows what an agency needs from a recording tool. She knows what an agency does not need.

What an agency does not need, she tells me, is balloons.

“They added balloons. They added all this crap that no agency is ever going to use, and then they turned around and said, ‘We’re going to change your rate from four hundred a month to eighteen hundred a month because now you have emojis and balloons, and you can make magic clips.’”

The list itself is the joke — emojis, balloons, magic clips, four times the price — and she delivers it flat, the way you read a receipt out loud. She is still annoyed about it years later. You can tell because she still remembers the exact dollar figures.

“They took the timer off for two and a half months a couple years ago,” she says. “I’m like, this is literally the very backbone of a recording is the timer.”

A timer. The one piece of an interface that tells the agency producer how long the conversation has been running, so they can pace it, cut to break, know when to wrap. Riverside removed it. For two and a half months. Then they came back with the new pricing.

“Like, tell me you don’t know anything about recording,” Molly says, “without telling me you don’t know anything about recording.”

I think about this line for the rest of our conversation. It is doing two things at once. It is making fun of a meme-shaped sentence — Molly knows exactly which corner of the internet she is borrowing from — and it is making a precise accusation. The people who built the product had stopped using the product. Or had never used it. Or had used it once, in a demo, and gone back to building features they could put in a Friday email so investors would feel motion.

“I’m an agency,” Molly says she told them. “We use Adobe. I’m never going to use your shitty editor, and I’m never going to give you eighteen hundred a month.”

So she didn’t. She left for a few years. She kept paying Zoom about five hundred a month instead, which she also thought was too much, but at least Zoom was not pretending to be something it wasn’t. Riverside lost her account. They lost six thousand dollars a year off one customer.

“And it’s easy to do that in any business,” she says. “Especially with AI. You’re like, oh, I can do all these things. But if you can’t do it consistently, if you can’t create a system around it, and if it doesn’t have any real value, then you’re just cluttering the inbox and you’re training people, including your clients, to ignore you.”

Training people, including your clients, to ignore you.

The pattern she’s describing isn’t unique to Riverside. I have watched a version of this play out at every venture-backed software company I’ve ever worked near.

There is a roadmap and the roadmap has features on it, and the features have shipping dates, and the shipping dates correspond to board meetings or all-hands or fundraises. The shape of the calendar dictates the shape of the product. Someone, at some point, decided that the answer to “how do we charge more” was “ship more,” and “ship more” became its own moral category. It stopped being a means and became the work itself.

I told Molly I think of myself as the “anti-product-management product manager”. That is the only way I know how to describe what I do. I run a product builder podcast, I have done product management along with design for years, and the thing I keep arguing with my own profession about is exactly this — the gap between making plans for teams and actually delivering value to a person who is going to write a check.

“It was probably some PM,” I say, “that thought, hey, we could justify charging them more if we just add more features, rather than worrying about value, like making a more reliable tool.”

There is a thing that happens inside companies where shipping becomes performance, and the performance is mostly for investors. You need something to tell at the next board meeting. Pointing at revenue is hard because revenue is slow and full of caveats. Pointing at features is easy. The features compound visually on a slide. The features sound like motion.

The customer, in this performance, is a kind of background actor. They appear in the dashboard as a churn number. They do not appear as Molly, on a call, telling you that you have killed her cost of goods sold.

This is the thing I want to fix and don’t know how to.

Molly’s story sits inside a larger argument she has been making for the full episode, which is about positioning. She runs Heartcast Media with what she calls singular clarity — podcast production as a business development tool, podcast booking, podcast growth, period. That is the sentence. It does not change. She has owned a company before, called One Love Massive, that supported community through art, music, and culture. Nineteen employees. A hundred and sixty artists. A three-story building in DC. And every week in the staff meeting she would have everyone do the elevator pitch, and nobody could agree on what they actually sold. She tells that story like a person who has paid the tuition. She’s not running that company anymore.

Heartcast is the second version. Heartcast is the company she built after she learned what it costs to be unclear.

So when she watches Riverside lose her account because they added emojis and balloons, what she is watching is the same lesson she paid for at One Love Massive, except this time it is someone else’s lesson and the someone else is the kind of company that gets covered in tech press. She is in the position of the seasoned business owner watching the unseasoned business owner make the obvious mistake. She is not surprised. She is annoyed.

“I’d say like, you guys gotta put yourself in the seat of the user,” she tells me she told the Riverside executives, after she escalated up the corporate line and got into one of their meetings. “You jumped the shark, man, big time.”

I keep thinking about that meeting. Molly, a paying customer with a six-thousand-dollar-a-year contract on a service that is supposed to be the core infrastructure of her agency, getting into a room with the executives and telling them they jumped the shark. I want to know what the executives were thinking during that meeting. I want to know if the PM was in the room. I want to know which of the people in that meeting was the one who shipped balloons.

I don’t actually know if Riverside is doing well now. Molly mentioned that they reportedly made ten million dollars in a year, plus another ten from an investor — the math of the venture funnel adds up even when the customers are angry. Riverside might be fine. Zoom might be fine. The companies that ship the wrong things often are fine, in the short run, because the financial mechanisms that fund them are not actually tied to whether the customers like the product. They are tied to whether the next round can be raised.

But the customer is keeping a ledger. Molly is the customer. Her ledger has a line on it that says six thousand a year, gone for years, because someone added balloons.

The thing about positioning, the thing Molly keeps trying to teach me across this conversation, is that the customer’s ledger is the only ledger that matters in the long run. You can perform velocity for the board for a few quarters. You can press-release your way through a fundraise. You can put balloons on the recording app and sell that as innovation. But the customers are forming opinions about you, in their own internal accounting, and those opinions calcify into reputation, and reputation is what makes the phone ring.

Or doesn’t.

“And I think that they hurt their reputation a lot,” she says, almost as an afterthought, “because it’s like you’re working for the investors, you’re not working for the people.”

She says it the same way she said the rest of it — without drama, the way you describe the weather. The way someone who has been doing this for twenty-five years describes a pattern she has seen before and will see again.

Six thousand dollars a year. One customer. One feature decision.

That’s the receipt.

Guest Bio: Molly Ruland

Molly Ruland is the CEO and Founder of Heartcast Media, a full-service podcast production studio she established in Washington, D.C. in 2018. Rising to prominence in the late 2010s as the demand for branded B2B podcasting accelerated, she became known for repositioning podcast production as a direct business development tool — not a media vanity project — for brands, NGOs, and founders seeking high-trust relationships with ideal clients. Under her leadership, Heartcast Media has produced more than 1,000 podcast episodes, including 7 programs that rank in the top 10% globally, with clients spanning the U.S. Department of Health, DC Government, NATO, and a range of entrepreneurs.

Previously, Ruland spent approximately 20 years running One Love Massive, a multi-sensory creative platform she built in Washington, D.C. that supported community through art, music, and culture. At its peak the operation employed 19 staff, managed 160 artists, and operated out of a three-story building — an experience that sharpened her understanding of brand clarity and the operational cost of an undefined offer. She credits One Love Massive with the hard lessons behind Heartcast Media’s singular positioning: podcast production as a business development and lead generation engine, period.

In 2026, Ruland co-authored Speak Your Way to Sales alongside nine other women entrepreneurs, a book focused on generating revenue through speaking, podcasting, and guesting. The title debuted at number one in Amazon’s small business category. She also hosts her own content marketing podcast and maintains a separate political interview series as a passion project.

Hey,

Thanks for reading this. I mean that. There’s a lot of content out there competing for your attention, and you spent some of it here. I hope it was worth it. Even better, I hope it prompted you to think about something differently enough that you’d share it with someone who’d get something out of it too.

I started this podcast because tactics never stuck with me. What stuck were stories — business biographies, autobiographies, the decisions people made and why they made them. The principle only clicks once you know the story behind it.

So I built the thing I wanted to listen to. Every week I have two conversations with people who build in technology and product. Then I write the essay in my premium newsletter (Taste Maker) to distill the principles and reflect on the narrative — one that puts you inside the conversation, through my eyes. What caught me off guard. What I kept thinking about after we hung up. Where the principle actually lives once you strip away the jargon.

I make this for myself first. If you read the way I do, you’ll want it too.

PS — If you want to pitch coming on the show, or you know someone I should talk to, shoot me an email at caden@hey.com with "January752" in the subject line so it gets past my filters. I'm not optimizing for famous guests. I'm optimizing for interesting conversations, even from people who aren't LinkedIn influencers.

Listen to this episode on Spotify or Apple Podcasts

In January 2025, Marcelo Calbucci sat down to write a PRFAQ for a new investment vehicle he was thinking of starting. By the end of the document, he had decided not to start it. The author of The PRFAQ Framework — six-time founder, ex-Amazon, ex-Microsoft — walks me through what writing forces you to see that a pitch deck never does.

“Let me say something that might surprise you,” Marcelo Calbucci tells me.

We are an hour into a conversation about a book he spent a year writing, and he says it the way a man lays a card face-up on the table — without flourish, watching to see what I do with it. “Most PRFAQs lead to a no-go decision.”

I should explain what a PRFAQ is, because the name does it no favors. It is the document at the center of Amazon’s Working Backwards process: a press release for a product that does not exist yet, followed by a long list of frequently asked questions about it. You write the thing as if it has already shipped, and then you interrogate it. Marcelo spent two years inside Amazon watching this process run at full weight — months of writing and review for a single bet, financial modeling, user research, the whole apparatus — and then he left and wrote a book adapting it for the people who never get that apparatus: founders, designers, product managers at companies with no research team to lean on.

So when the author of the book tells me that most of the documents the book teaches you to write should end in no, I do the thing I suspect he wants me to do. I push back. That sounds like failure. You do weeks of work, and the deliverable is that you don’t build the thing?

He has heard this before. I can tell because he doesn’t reach for theory. He reaches for himself.

“This is very personal,” he says. Last January, he sat down to write a PRFAQ for something he genuinely wanted: a new investment vehicle for founders. Not a thought experiment. A real next move for a man who has started six companies and raised more than forty million dollars doing it. He knew the shape of the thing. He could have built a pitch deck for it in an afternoon and felt good walking out of the room.

Instead he opened a blank document and started writing the press release for it — the announcement he’d make if the thing already existed and had already worked. Then the questions underneath it, the ones his own framework forces: who is the customer, whether the problem he was so sure existed actually existed or just felt like it did, how the people he wanted to serve were already solving it without him. Each answer he was confident about sent him to go check, and the checking sent him back to the document less confident than he’d started, and somewhere in that loop the thing began doing what he wrote an entire book about. It started talking back.

This is the part outsiders never see about a man with his record — six companies founded, more than forty million dollars raised across them, eighteen years spent deciding what to build and convincing other people to fund it. You would assume that by now the deciding gets easier, that a founder six times over walks into his seventh idea with the confidence of someone who has been right before. What he was describing instead was a person voluntarily sitting down with the one tool guaranteed to make a good idea harder to keep believing in. He did not have to write the document. Nobody was making him. He wrote it because he has learned not to trust an idea he has not yet tried to talk himself out of.

I want to know what it said. I want to know whether a man who has done this six times can really sit in a room with his own idea and let a Word file argue him out of it, or whether that is the kind of thing you say in an interview and not the kind of thing that happens at a kitchen table in January.

He pauses on the word realized, like he is deciding how honest to be about what came next.

What he decided that month — and the reframe he handed me when I called it a waste — is the part of the conversation I have been turning over since we hung up.

What this profile covers

1. What that document did to a founder who has been right six times before — and the reframe he handed me when I called the whole exercise a waste. The shift he names is small, a single change in what you choose to measure, and he uses it to separate the product managers who last from the ones who burn out. Once he said it, I could not unsee how much of product work is built to reward the wrong number.

2. Why the process can’t simply be lifted out of Amazon and dropped into your company — the part of his book that got ahead of every objection I came in with. It starts with a sixty-minute meeting that opens with twenty minutes of total silence, and it ends somewhere uncomfortable for anyone who has ever said “let’s just do it the way Apple does it.”

3. And the line he draws through the middle of 2026’s most tempting shortcut: what you can hand to an AI to write, and what you must refuse to. The example that makes it concrete is the most boring feature request in software — a customer asking for tags — and what Marcelo does with it is the whole argument for why the thinking is still yours.

Read more

Listen to this episode on Spotify or Apple Podcasts

Drew Bridewell spent years at LinkedIn and Facebook with no access to the P&L, then watched AI dissolve both the cost of learning the finances and the cost of the design-system maintenance that used to eat the time he would have needed to learn them. What’s left is the thing only designers can do: visualize what doesn’t yet exist with enough specificity that other people see it, align around it, and believe in it.

About a third of the way into our call, Drew Bridewell catches himself mid-thought and reframes the word he’s been using for his job.

“I’ve really shifted into, like, this operator language,” he says, “because as an operator for any business or any company you, you participate in, you need to understand the finances, you need to understand the economics, you need to understand how the company makes money, how they lose money, then, and then also how much it costs to have a team, how much it costs to have AI as a resource.”

He says it the way someone says a phrase they’ve grown into recently. Operator. Not designer. Not head of product & design, which is what his title at GrowthDay said for five years. Operator, with all the inheritance the word carries — that you spend somebody’s money, or you make it, or you don’t, and the people in the room know which.

The shift, when he describes it, isn’t a re-branding. It’s a diagnosis.

“All the things that I love about the, the, like, the foundations and principles of UX don’t even matter if you don’t understand how the company is supposed to operate,” he tells me. “’Cause then you can’t work backwards, you can’t figure out, like, the root of the problems. You’re just basically taking orders.”

Just basically taking orders. He doesn’t put it sharper than that, and he doesn’t have to. The whole career argument designers spent the last twenty years making — that craft matters, that thinking matters, that we should be in the room where the product decisions get made — collapses in front of that sentence. The room was never refusing the craft. The room was refusing the conversation that happens in the language of dollars, and the craft, on its own, couldn’t get there.

I came up through this argument from the other side. I have a human-computer interaction degree. I was a UX-pilled graduate of my design school in the era when companies hired UI talent, not UX talent — when the market rewarded the people who could ship the prettiest screen, not the people who could explain why the screen should exist. I watched designers fight, decade after decade, for the seat. The fight was real and the seat is real. What I underestimated was how much the seat was always financial.

Drew makes it concrete with where he learned it.

“I learned it more as I got further and further away from big tech,” he says. “Because, you know, at, like, LinkedIn and Facebook, I’m not, I wasn’t, like, getting, um... I, I didn’t have access to the, the P&L of those massive companies, but I definitely, you know, we, we’d see the movement, and we had, we had really strong VPs and, and leadership there, but we weren’t, you know, that wasn’t a discussion that designers got to have, uh, and that was a big problem. And I think we would all have been more successful 10 years ago if literally everybody in the company understood the finances.”

That last clause is the breakthrough sentence of the whole conversation. We would all have been more successful ten years ago. Not the designers — all of us. The thing he’s describing isn’t a missing skill on the design side. It’s a structural choice on the company side, made when finance was an expensive specialty and giving everyone a window into the P&L would have been more risk than reward. So the designers spent the decade making craft arguments to people who were having a different conversation in a different language in another room. And the designers who eventually did get into that other room got there by going someplace small enough that they couldn’t avoid the finances anymore — which is the path Drew describes for himself, getting smaller and smaller until the numbers were on the same table as the work.

For a long time, the cost of learning that other language was high enough that it sorted people. You either spent two years and a hundred thousand dollars on a degree that taught you to speak finance, or you accepted that someone else would always be the one in the room translating between the design and the business. That sort was the gate. It wasn’t subtle, and it wasn’t fair, and the people on the inside of it ran most of the companies the designers were trying to influence.

Two things changed in the last couple of years, and Drew has spent his own money learning both of them.

The first is that the financial half of the literacy stopped being expensive. The frameworks and the vocabulary — what a P&L is, what a balance sheet is, how revenue and cost of revenue and contribution margin actually move — are a short course away now. The math you used to need to do by hand is something a spreadsheet does, and the moments where you’d freeze because you didn’t know the next move are moments where you can ask. You don’t need a degree to price a design decision anymore. You need the patience to learn the words and a tool that handles the arithmetic. Drew is matter-of-fact about it. The barrier wasn’t conceptual; it was access. Access just dropped.

The second is that AI removed the other half of the cost — the half nobody was talking about. For most of Drew’s career as a senior design leader, the unglamorous job underneath the title was maintenance. Maintaining the Figma library. Versioning the components. Mediating the requests for new variants. Shipping the tickets that kept the design system internally consistent so the rest of the team could move. That work was real, and necessary, and it consumed exactly the hours a designer might otherwise have spent learning the business.

About a year before our conversation, Drew started paying out of pocket for the maxed-out versions of Claude Code, Bolt.new, and Codex — a hundred to two hundred dollars a month of his own money. He started testing into onboarding funnels at GrowthDay, building variants in Claude Code or Bolt.new, shipping them, watching them, tearing them down. By his count, hundreds of variations in a year. By the end of the year, the engineering team trusted him to migrate to production.

Then he did the thing that’s hard to describe without making it sound either smaller or more dramatic than it was.

“I ended up reproducing our entire, like, Figma, basically Figma design library inside of Cloud Code,” he tells me. He means Claude Code; the audio system has been hearing the brand name as “Cloud” all conversation and I’ve stopped correcting it in my head. “It allowed my CEO or anybody to go and pull from that Git repo and then just ask for anything that you want, and then it would just produce it.”

What he just described is the dissolution of the design-system-maintenance job. Not its outsourcing. Its encoding. Five years of accumulated taste — every button, every type ramp, every brand decision people argued into existence — translated into a system that could produce in the brand’s voice from natural-language prompts. Anyone on the team, including the CEO, could ask for a funnel page or a post and get something brand-consistent back. The library went from a thing a person had to maintain in tickets to a thing the company carried in code. The job that used to eat the senior designer’s week stopped existing in the form that ate it.

And here is the conjunction the conversation hangs on. The two costs that kept designers out of the operator conversation — the cost of learning the finances and the cost of maintaining the system — both dropped at roughly the same time, on roughly the same curve, for roughly the same reasons. What was a permanent trade-off five years ago became, in the course of a year, a choice.

I ask Drew what a designer does with that, once they see it. He doesn’t pause.

“That’s why I think I’ve really shifted into, like, this operator language,” he says again. The word lands differently the second time. The first time he said it, it sounded like an identity move. The second time, it sounds like an point of view about where the work is now.

This is, I notice, the same Drew who introduced himself at the top of the call by giving me a title I hadn’t heard before.

“My name is Drew Bridwell,” he’d said. “I’m now a chief design operator. I’m primarily focused on helping founders bring their visions to life.”

Chief design operator. The compound is doing real work. The design half is the craft — twenty years of Lynda.com and LinkedIn and Facebook and InVision and GrowthDay. The operator half is what he learned the hard way, going small enough that the P&L finally got close enough to read. Sitting between the two is what AI freed him to actually do — visualize, make the unbuilt thing legible, get the people who have to fund it and ship it and sell it to look at the same picture.

Because that last part — visualization — is the thing that doesn’t get cheaper.

The frameworks you can buy. The maintenance you can encode. What you can’t outsource is the act of seeing what doesn’t yet exist with enough specificity that other people can see it too. That’s still a designer’s job, and it’s still rare, and it’s the thing the operator language was supposed to be in service of all along. When a founder is staring at a blank space and a board is staring at the same blank space and the team is waiting to be told which version of the thing to start building, the person who can put something concrete enough on the table for everyone to react to is the person doing the load-bearing work.

That work creates alignment, in the most literal sense of the word. The picture is on the table. We’re looking at it together. We agree this is the thing.

“He had to learn, and he’s not like any other CEO,” he says of Brendon. “He’s like, like a high-performing CEO, so he’s like learning and doing things as well and learning from us ‘cause, you know, I write about all this stuff in my status update every week, right? So I’m like, I’m, I’m a transparent, I’m a transparent beast. Like I’m gonna share it all.”

Transparent beast. He says it without irony. The transparency is how the visualization earns belief — not as a one-shot demo, but as an ongoing public record of the thing coming together. He wrote the weekly status update the whole way through. By the time the design library was in the repo, nobody had to be sold on what they were looking at. They’d been reading the receipts for months. The picture had been forming in their inboxes one Friday at a time, in his voice, on the record, and the day the keys were available the team had already been living in the thing they were now being handed.

What design at the operator level actually does, then, sits on top of both the craft and the finances rather than choosing between them. The work is making something invisible — a strategy, a brand, a year of decisions — visible enough that a roomful of people can agree it exists. Then writing the receipts every week so the agreement isn’t dependent on you being in the room.

There’s a line at the end of our call I keep replaying. Drew is talking about the next twenty years, about the five to ten founders he’ll work with, about the small businesses about to get well-made software for the first time. He says he projects one to two million dollars a year in this next phase. He says it like arithmetic, not a target. And then he adds, almost as an aside, the line that turns out to be the answer to the whole conversation:

“I’m trying to teach the whole system, not, not just one thing.”

The whole system. Not as the sum of the craft and the finances and the picture, but as the practice of holding all three in the same room at the same time. Designers spent twenty years asking for a seat at the table, and what they were really asking for was the conversation the table was having — the one in dollars, the one in trade-offs, the one about what gets built and what doesn’t. The conversation is open now. The seat costs what it always cost. The price just stopped being out of reach.

Guest Bio: Drew Bridewell

Drew Bridewell is a Chief Design Operator and fractional product design leader, helping founders across industries build custom digital products at a fraction of traditional costs. Rising to prominence in the 2010s as a design educator and systems architect, he became known for bridging the gap between UX craft, business operations, and high-performance team design — a practice built over two decades at companies including LinkedIn, InVision, and GrowthDay. He holds a Certified High Performance Coach (CHPC) credential and is the founder of Next Level UX, an operating system for designers and operators combining 20 years of design practice with research-backed high-performance habits.

Previously, as Head of Product Design at GrowthDay — a personal development platform built around Brendon Burchard’s six high-performance habits framework — Bridewell spent five years leading product experiments, testing hundreds of onboarding funnel variations using Claude Code and Bolt.new, and shipping code directly to production. He rebuilt GrowthDay’s entire Figma design library inside Claude Code, enabling the CEO to self-serve product iteration without a dedicated engineering headcount. Over three years of the engagement, he taught weekly live design and performance frameworks on the platform, reaching the company’s subscriber community of coaches, executives, and high-performance practitioners.

His career highlights include serving on the Design Transformation team at InVision, where he mapped the design systems and organizational maturity of hundreds of enterprise clients. Earlier, at Lynda.com prior to its acquisition by LinkedIn, Bridewell hosted Practical UX Weekly on LinkedIn Learning — a widely-followed series on interaction design principles that introduced a generation of early-career designers to the foundations of UX. He earned his degree from the Savannah College of Art and Design.

As founder of Next Level UX, Bridewell coaches designers, operators, and founders through systems built at the intersection of design thinking and financial literacy — teaching the operator skills that enable practitioners to price design decisions, understand P&L, and deliver at the level of a full product team as a single fractional contributor.

Hey,

Thanks for reading this. I mean that. There’s a lot of content out there competing for your attention, and you spent some of it here. I hope it was worth it. Even better, I hope it prompted you to think about something differently enough that you’d share it with someone who’d get something out of it too.

I started this podcast because tactics never stuck with me. What stuck were stories — business biographies, autobiographies, the decisions people made and why they made them. The principle only clicks once you know the story behind it.

So I built the thing I wanted to listen to. Every week I have two conversations with people who build in technology and product. Then I write the essay in my premium newsletter (Taste Maker) to distill the principles and reflect on the narrative — one that puts you inside the conversation, through my eyes. What caught me off guard. What I kept thinking about after we hung up. Where the principle actually lives once you strip away the jargon.

I make this for myself first. If you read the way I do, you’ll want it too.

PS — If you want to pitch coming on the show, or you know someone I should talk to, shoot me an email at caden@hey.com with "January752" in the subject line so it gets past my filters. I'm not optimizing for famous guests. I'm optimizing for interesting conversations, even from people who aren't LinkedIn influencers.

For years Brian Donohue thought the six-week cycle was the sweet spot — they’d arrived at it independently, the same place Basecamp landed. Then Intercom rebuilt its support product around large language models, and the cycle, the triad, and the stable teams all went out the window.

Listen to this episode on Spotify or Apple Podcasts

Guest Bio: Brian Donohue

Brian Donohue is the VP of Product at Intercom, where he leads product development for Fin, the company’s AI agent for customer support. Rising to prominence through more than a decade at Intercom, he became one of the defining figures behind the company’s transformation from a traditional SaaS helpdesk into an AI-first customer service platform. Under his leadership, Fin grew from a June 2023 launch with a 25% resolution rate to a sustained average of 65% resolution across all paying customers — widely regarded as one of the most measurable success records in enterprise AI product development.

Previously, as Director of Product Management at Intercom, Donohue oversaw multiple product areas during the company’s rapid growth years, building deep expertise in outcomes-driven development, user onboarding, and messenger interface design. Before Intercom, he served as Director of Design at Houghton Mifflin Harcourt, where he accumulated more than twenty years of combined design and product leadership experience across enterprise and consumer contexts.

Donohue has been a vocal advocate for technical rigor in AI product development, having championed the adoption of consumer-grade A/B testing methodologies within Intercom’s R&D organization and the firm’s transition to outcome-based pricing — charging per resolved customer conversation rather than per seat.

Key Conversation Topics

1. Continuous reassessment as strategy — Intercom questioned “are we going bold enough?” every three months rather than making one big bet. Incremental big swings added up to a massive shift.

2. Inherited product blindness — Even though Fin was “built from scratch,” Intercom was still anchored to old UX decisions (button-based resolution confirmation) that took two years to recognize and fix. The fix actually significantly improved resolution rates.

3. Outcome-based pricing aligning incentives — Charging per resolution ($0.99/resolution) aligned what customers want, what the product team optimizes for, and what finance cares about in a way seat-based pricing never could. Resolution rate climbed from ~25% at launch to ~65%.

4. The AI operating model shift — Throwing out the six-week cycle, the triad, and traditional team topology. “Follow the work” rather than organizing around stable teams. Destabilizing but effective for speed.

5. Technical uplift required for AI product managers — Natural language as the programming interface doesn’t lower the bar — it raises it. Engineers think in rule sets and constraints; PMs now need that same rigor.

6. R&D Services as a critical new muscle — Forward-deployed R&D folks (like Palantir’s model) are essential for getting customers to value. AI transformation requires hands-on implementation support. PLG counterintuitively did NOT get amplified by AI.

7. Build to think / prototyping value for PMs — The real opportunity for PMs isn’t doing final design — it’s using AI tools to prototype fast enough to validate ideas before bringing in designers.

Themes

• AI agent product development at scale

• Outcome-based pricing in SaaS

• Organizational transformation under AI pressure

• The paradox of technical uplift under “democratized” technology

• A/B testing rigor borrowed from consumer product applied to AI

Hey,

Thanks for reading this. I mean that. There's a lot of content out there competing for your attention, and you spent some of it here. I hope it was worth it. Even better, I hope it prompted you to think about something differently enough that you'd share it with someone who'd get something out of it too.

I started this podcast because tactics never stuck with me. What stuck were stories — business biographies, autobiographies, the decisions people made and why they made them. The principle only clicks once you know the story behind it.

So I built the thing I wanted to listen to. Every week I have two conversations with people who build in technology and product. Then I write the essay in my premium newsletter (Taste Maker) to distill the principles and reflect on the narrative — one that puts you inside the conversation, through my eyes. What caught me off guard. What I kept thinking about after we hung up. Where the principle actually lives once you strip away the jargon.

I make this for myself first. If you read the way I do, you’ll want it too.

PS — If you want to pitch coming on the show, or you know someone I should talk to, shoot me an email at caden@hey.com with "January752" in the subject line so it gets past my filters. I'm not optimizing for famous guests. I'm optimizing for interesting conversations, even from people who aren't LinkedIn influencers.

Listen to this episode on Spotify or Apple Podcasts

“I’ve got a quick example if I got time for it,” Vance Morris says. “Is that okay?”

It’s his interview. I tell him to go ahead.

So he tells me about an insurance agency. He’d been brought in to fix one specific thing: the way they answered the phone. It sounds small until you realize that answering the phone was the agency’s number one source of new business. Every lead came through that one ringing line, and the people picking it up sounded like everyone else who has ever picked up a phone. “Thank you for calling Dave’s Insurance. How can I help you?” Pleasant. Forgettable. Indistinguishable from the agency across the street and the one across the country.

Then Vance walked into the owner’s office. Gold records on the wall. Autographed guitars. The man was a rock and roll fanatic, and his entire personality was hanging there in frames, and nobody had thought to let it leak into the business. “We should really lean into this personality a bit,” Vance told him. And then comes the part Vance wants me to hear: the fix came from the receptionist. The idea was to answer the phone by channeling Wolfman Jack, the rock-radio howl. From then on, the phone got answered a different way.

“Thank you for calling Dave’s Allstate, the agency that rocks.”

I laugh, because it works, and because it’s the kind of thing that sounds like a gimmick until you sit with it for a second. Vance has clearly sat with it for longer than a second. He breaks it apart for me like he’s done it a hundred times, because he has. What to do: answer the phone. How to do it: the agency that rocks. And then he slows down on the third one, the one he actually cares about.

Why do we do it that way?

“Your marketing is designed to do two things,” he says. “Attract the people you wanna do business with and repel the people you don’t.” Answer the phone like a rock station and you start sorting your callers before they’ve said a word. The people who smile are your people. The people who frown and hang up were never going to be easy clients anyway. And underneath the sorting, there’s a second thing happening, which is that nobody else in the country is answering the phone that way, so the agency has quietly become the only one of its kind. “He owns it,” Vance says.

That’s when he gives me the line I anchor on. The why is what lets your employees “really have something that they can wrap their brains around.”

I want to stay on that, because I think it’s the whole interview hiding inside a phone greeting.

Vance spent about ten years at Walt Disney World. He was on the opening teams for the Yacht and Beach Club, for Pleasure Island, for Animal Kingdom, and his signature build was Chef Mickey’s, the character dining experience at the Contemporary Resort. He is, by his own cheerful admission, a lousy employee. “I just don’t like to be told what to do,” he tells me near the top of our conversation, which puts him “in the unemployable realm of things.” A man like that staying somewhere for a decade is worth paying attention to. He didn’t stay because Disney told him what to do. He stayed because, for nine and a half of those years, Disney was building things, and he got to build them. He was on the opening team. There was creation going on, and systems and processes being invented rather than maintained, and that was the work that held him.

And then it stopped, and that’s the part that should make every executive nervous. Growth slowed. “Processes and systems were just being managed as opposed to being created,” he tells me, and I can hear the moment land in his telling. “That’s where I kind of start to feel, eh, I’m not feeling overly creative anymore. I should look somewhere else.” Nothing went wrong. No one mistreated him. The company simply finished its 20 percent and settled into running the 80, and the man whose whole value was the 20 percent felt himself becoming redundant in a building that no longer needed anyone to invent anything. So he left. The lesson cuts both ways: the 20 percent isn’t only where you differentiate your product. It’s where you keep the people who can build the next one.

But the thing he carried out the door wasn’t the magic. It was the plumbing.

“Disney runs on systems and processes,” he says, and he knows how that lands. He knows the word “process” makes people picture employees behaving like robots, creativity drained out of them by a checklist. He thinks that’s exactly backward. “If you design a great process, an extraordinary process, it’s gonna deliver an extraordinary result.” That’s how a company gets 75,000 employees all singing the same song. There’s a process for waiting on a table. There’s a process for changing a bus tire. There’s a process for nearly everything, and the processes are simple, and that simplicity is the point.

Here’s the mechanism he describes, and it’s the part that reorganized something in my head. When the job becomes muscle memory, what he calls “muscle reflex memory by rote,” you stop spending your attention on the job. “It gives your brain 20 to 25% excess capacity,” he says, “’cause you’re not thinking about your job, you’re just doing it.” The systems aren’t there to make people smaller. They’re there to free up the exact slice of a person that the company actually wants: the part that takes the photo, gives the directions, signs the autograph, notices the kid who dropped his ice cream. The 80 percent runs itself so the 20 percent can show up.

Vance took that home and pointed it at three businesses nobody dreams about as a kid: carpet cleaning, mold remediation, an Oriental rug washing facility. He built a marketing system, a retention system, an operations system. He hired a general manager and gave him a single instruction. “Just manage the systems. Don’t screw with anything, just manage the systems.” They meet for an hour every Friday morning at 7:30 to talk through any improvements, and then the manager marches off and executes. Vance spends the other half hour of his week on the accounting, because he doesn’t let anyone touch the checkbook. Ninety minutes a week, total, on three companies. That’s what a well-designed 80 percent buys you.

I tell him what I think I’m hearing, because by now I can feel a shape forming. You systematize the 80 percent, the table stakes that don’t set you apart, precisely so you can stop sweating it. And the reason you tell employees this isn’t to keep them in their lane. It’s to draw the lane on purpose. This part is table stakes, so don’t waste your creativity reinventing it. This other part, the 20 percent, is where we actually compete, and that’s where we need your brain.

“Yeah,” Vance says, and he starts listing the companies that live this way. The Ritz-Carlton. Harley-Davidson. Apple. Each of them has the systems-and-processes piece locked down, and each of them also has the part that asks, constantly, “How do we make this thing better? Or how do we make it completely new?” They go hand in hand. And then he tells me where most people get it wrong, which is by giving the creative part too much room. “20% is enough,” he says. “’Cause otherwise you’re just going off in a myriad of directions and you kind of just flounder around and get lost.”

This is the trap I’ve watched product teams fall into from the other side. They systematize the wrong fifth. They build rigid process around the very thing that’s supposed to set the company apart, and they leave the table stakes to improvisation, so the differentiator calcifies while the basics stay sloppy. It’s the inversion of everything Vance is describing. The phone greeting gets standardized into beige, and the actual personality — the gold records on the wall — never makes it into the building.

What strikes me, sitting with all of it, is that the three words aren’t really a management framework. They’re a way of treating people like they can hold an idea. Most businesses stop at two because two is enough to get the task done. You can tell someone what to do and how to do it and the phone will get answered. But you’ll have built a person-shaped machine, and machines don’t channel their inner Wolfman Jack. The third word is the one that says: here is the reason this matters, and I trust you to do something with it.

And the proof, in Vance’s story, isn’t him. It’s the insurance company owner that had an affinity for rock and roll.

Vance didn’t hand down a script. He gave the owner a why: lean into who you actually are. And somewhere down the chain, a person who answers the phone for a living heard that why and invented the how. The agency that rocks.

That’s the line still ringing at that office, and no consultant wrote it. Someone who finally understood the “why” did.

Guest Bio: Vance Morris

Vance Morris is the Founder of Deliver Service Now!, a consulting and coaching firm that teaches small and midsize businesses how to implement Disney-caliber customer experience systems combined with direct response marketing. Rising to prominence through a decade of leadership at Walt Disney World, he became the creative lead behind Chef Mickey’s — Disney’s flagship character dining experience at the Contemporary Resort — a concept whose systems have remained largely unchanged for more than 25 years. He also built and systematized three home service businesses in Maryland (a carpet cleaning company, a mold remediation company, and an Oriental rug washing facility) to operate on 90 minutes of his attention per week.

Previously, as a manager and trainer at Walt Disney World through the 1990s expansion era, Morris served on the opening teams of the Yacht & Beach Club Resorts and Animal Kingdom, and acted as All-Island Duty Manager at Pleasure Island. He was recognized for generating $125,000 in business from a single marketing campaign, earning the Marketer of the Year award at a GKIC competition in 2015 and an International Marketing Award in a Dan Kennedy competition.

His consulting client roster has included NASA, the Smithsonian, the Kennedy Center for the Performing Arts, Legal Seafoods, Tyson, Rainforest Café, and Compass Group. He has shared stages with Daymond John, Dan Kennedy, Joe Polish, and Jack Canfield across more than 40 years of speaking experience.

Morris is also the creator of 52 Ways to WOW Your Customer, a free resource delivering one customer experience tactic per week of the year.

Hey,

Thanks for reading this. I mean that. There's a lot of content out there competing for your attention, and you spent some of it here. I hope it was worth it. Even better, I hope it prompted you to think about something differently enough that you'd share it with someone who'd get something out of it too.

I started this podcast because tactics never stuck with me. What stuck were stories — business biographies, autobiographies, the decisions people made and why they made them. The principle only clicks once you know the story behind it.

So I built the thing I wanted to read. Every week I have two conversations with people who build in technology and product. Then I write the essay I wish I could find — one that puts you inside the conversation, through my eyes. What caught me off guard. What I kept thinking about after we hung up. Where the principle actually lives once you strip away the jargon.

I make this for myself first. If you read the way I do, you’ll want it too.

PS — If you want to pitch coming on the show, or you know someone I should talk to, shoot me an email at caden@hey.com with "January752" in the subject line so it gets past my filters. I'm not optimizing for famous guests. I'm optimizing for interesting conversations, even from people who aren't LinkedIn influencers.

Listen to this episode on Spotify or Apple Podcasts

Partway through our conversation, I admit something to Khurram Mir that I’m not proud of.

“Whenever I have friction with a QA partner,” I tell him, “it’s because I feel like they’re being nitpicky about something.” They block the launch. They say no, this doesn’t work about something that, to me, looks finished enough to ship. I’ve been guilty of this recently — the quiet resentment that builds when the person whose entire job is to find problems keeps finding them at the exact moment you want to be done.

I expect Khurram to take my side. He has, after all, spent his career on the testing side of the table. He started in software testing in 2001, drawn to it because it asked him to think like a user instead of an engineer. He built Qualitum into a consulting firm with offices in five countries and more than fifteen years behind it. If anyone is going to defend the QA person against the impatient product manager, it should be him.

He doesn’t defend the QA person. He doesn’t defend me either. He does something more useful — he tells me the friction is a symptom, and then he tells me what it’s a symptom of.

“If you bring in QA early,” he says, “this is the best thing you could do for your own product.”

Then he stops, and takes a step back, the way you do when you realize the listener is holding the wrong frame entirely.

“Let’s not think QA as technical software engineers,” he says. “Let’s think of this person as somebody who is going to look at your application like an end user.”

I tell him I think I see where this is going, and he keeps pulling the thread. The QA person, he says, can be your beta user. Your friend who’s going to use the app. And then he says the line that reorganizes the whole problem for me.

“Let’s not even use the word test here. This person is going to use your application.”

There’s a weight on the word use when he says it — not a correction so much as a reveal, like he’s been waiting the whole conversation to put it that plainly. Because the consequence is immediate and it lands on me, not on the tester. “If you don’t bring this guy up to the speed on what the product is supposed to do,” he says, “and you don’t give them enough time and enough understanding of how the product is supposed to work as a user, they cannot really look into this application and give you any valuable feedback.”

I want to argue. I don’t, because I already know he’s right, and I know it because of a complaint I make about my own QA partners constantly. They tell me the form isn’t working. The submit button isn’t working. The field doesn’t validate. Khurram names this before I can.

“They may be able to tell you, this form is not working, this field is not working, my submit button is not working,“ he says, “but that even a CTO can figure out.”

That stings in the specific way that true things sting. The feedback I’ve been dismissing as nitpicky is exactly the feedback a context-starved tester is able to give. It’s the floor. It’s what’s left when you hand someone a finished build and no reason to care about it.

Earlier in our conversation I’d reached for a metaphor without realizing it was about to indict me. I’d been talking about video game testers — the ones you see in shows like Mythic Quest, paid to sit and play a game all day and log what breaks.

The reframe I loved was that they’re not outside the game. They’re playing it. They’re immersed, in character, trying to be the god of war in the game about being the god of war. And then I’d said the part I should have heard more carefully the first time: if all you do is hand someone a game with no context and tell them to play it, what can they possibly give you back?

“You just point out all the — everything that’s wrong with it,” I’d said. “Well, yeah, this button doesn’t work. Oh, the border radius is off by this many pixels.“ Because, I’d told him, “I need to justify my position, and you’re not giving me a lot to work with.”

The border radius. That’s the picture I can’t shake now. A person who was hired to protect the quality of your product, reduced to counting pixels, because counting pixels is the only thing left to do when nobody told them what the product was for. The nitpicking isn’t pettiness. It’s a person doing the only job you actually gave them.

Khurram takes the idea somewhere I hadn’t. The difference between a developer and a tester, he tells me, isn’t seniority or skill. It’s what they do with a user story.

“If you share a user story,” he says, “the developer will think, Oh, I need to implement this user story, and I have to write the code this way. But a tester needs to think of everything around that user story.”

He lets that sit, and then sharpens it.

“What is not written in that user story is what a tester has to think about.”

This is the whole craft compressed into a sentence. The developer builds what the story says. The tester is responsible for the negative space — every way a real person will use the thing that nobody bothered to write down, because the feature you shipped to be used one way will reach a customer who uses it some other way entirely. And a person can only see the negative space if you’ve shown them the whole picture first. You cannot ask someone to imagine what’s missing from a document they were never given.

Which is when Khurram describes the trap his testers live inside, and I recognize it as the exact trap I’ve been blaming them for.

“QA guys have this problem,” he says. “If they don’t report everything, then the team says, Oh, you didn’t report this. And if they over-report, then people say, Oh, you are wasting your time, because we have to filter out all the unnecessary stuff.“

So the tester logs everything, including the border radius, because the one time they don’t log something it becomes the thing that shipped, and then it’s their fault. Over-report and you’re nitpicky. Under-report and you’re negligent. There is no safe move available to a person who doesn’t know what matters. The double-bind isn’t a personality flaw in the QA team. It’s the predictable output of a system where nobody told them what to care about.

I say it out loud, because by now it’s the only honest thing left to say. If QA is being nitpicky, it’s my fault — because they don’t know what to look at. They don’t know what to evaluate.

Khurram answers with a question I’ve been circling the entire conversation without landing on.

“What is the priority?”

He says it like the question contains its own answer, and it does. “As a product manager,” he says, “you must prioritize it for them. You must tell them, Look, in terms of priority, these are the features that we need to look at.“ Not because the tester is incapable of judgment — the opposite. He’s clear that QA needs to come back with their own opinion, their own suggestions, their own sense of where the product could be better. But the priority, the frame, the this is what good looks like for this release — that has to come from the person holding the vision. That’s not testing work. That’s product work. I’d been outsourcing my own job and then resenting the people I outsourced it to for doing it badly.

There’s a number Khurram offers that makes the cost of getting this wrong concrete. He tells me you are far better off having a QA person hand you two extra bugs than having a customer send you a single one. The math isn’t close. A bug a customer finds engages your support team, your developers, your reputation, and your own attention, all at once, at the worst possible time. A bug your tester finds costs you a conversation. The nitpicky QA person you’ve been quietly resenting is the cheapest insurance you will ever buy, and the resentment is just the sound of you misreading the invoice.

Near the end, Khurram makes the shift explicit, and it reframes the whole category for me. Imagine, he says, the tester comes back not with a list of broken buttons but with something else: I used this. Here’s how you could make it better.

“QA shifts, in my opinion, from a cost center to a value center,” he says, “the moment you start thinking of QA as not just somebody finding me issues.”

I’ve spent years treating the QA function as a tollbooth between me and shipping.
A job family that exists to slow me down — and occasionally to embarrass me.

Khurram has spent his career on the other side of that glass, watching product managers like me hand a finished build to a stranger, withhold every reason to care about it, and then take the resulting pixel-counting as proof that testing is a tax.

The border radius was never the problem. The border radius was the answer to the only question I’d actually asked.

Guest Bio: Khurram Mir

Khurram’s Substack

Contrarian takes on software quality and engineering leadership.

By Khurram Javed Mir

https://www.linkedin.com/in/khurrammir/

https://www.youtube.com/@khurramjmir

Khurram Mir is the Co-Founder and Chief Marketing Officer of Kualitatem, a specialized software quality engineering and information systems auditing firm operating across the United States, UAE, Saudi Arabia, Qatar, the United Kingdom, the Nordics, and Asia, and the Co-Founder of Kualitee, an AI-powered test management platform that grew out of Kualitatem’s internal tooling. Rising to prominence after beginning his career in software testing in 2001, Mir has spent more than two decades building the methodology and infrastructure that define enterprise QA at scale, accumulating over 500,000 hours of testing delivery and working with more than 200 client organizations across more than 350 applications.

Mir co-founded Kualitatem in 2009 on the conviction that independent quality assurance should be a non-negotiable phase of every software development lifecycle, not an afterthought appended at the end of a release cycle. The firm achieved TMMi Level 5 certification — the highest maturity designation in the Testing Maturity Model integration framework — and has maintained ISO 27001 and ISO 9001 certification for six consecutive years. Kualitatem also developed an internal training institute to build consistent QA discipline across its geographically distributed team. A banking engagement that became a defining case study demonstrated that involving QA teams at the requirements stage — a shift-left approach — eliminated 33 percent of defects before formal testing even began.

In 2016, Kualitatem productized the internal consistency tooling it had built to maintain uniform service quality across multiple countries, launching Kualitee as a standalone test management platform. The platform’s generative AI engine produces test cases directly from user stories and test scenarios, with Kualitatem’s own teams reporting a 23 to 27 percent reduction in testing time as a result. Kualitee now serves more than 2,000 engineering teams worldwide, including clients such as Emirates, T-Mobile, and Cox Enterprises, and has been recognized by G2 as a leading test management solution across multiple regional and segment reports. Mir serves as product manager for Kualitee in addition to his operational role at Kualitatem — a dual function that reflects the firm’s broader thesis: that the services mindset and the product mindset must be learned separately, even when one organization spawns the other.

Hey,

Thanks for reading this. I mean that. There's a lot of content out there competing for your attention, and you spent some of it here. I hope it was worth it. Even better, I hope it prompted you to think about something differently enough that you'd share it with someone who'd get something out of it too.

I started this podcast because tactics never stuck with me. What stuck were stories — business biographies, autobiographies, the decisions people made and why they made them. The principle only clicks once you know the story behind it.

So I built the thing I wanted to read. Every week I have two conversations with people who build in technology and product. Then I write the essay I wish I could find — one that puts you inside the conversation, through my eyes. What caught me off guard. What I kept thinking about after we hung up. Where the principle actually lives once you strip away the jargon.

I make this for myself first. If you read the way I do, you’ll want it too.

PS — If you want to pitch coming on the show, or you know someone I should talk to, shoot me an email at caden@hey.com with "January752" in the subject line so it gets past my filters. I'm not optimizing for famous guests. I'm optimizing for interesting conversations, even from people who aren't LinkedIn influencers.

Listen to this episode on Spotify or Apple Podcasts

John Long has spent 15 years selling technology — and the clearest pattern he’s noticed is that when product and sales stop trusting each other, the company doesn’t just slow down, it inverts.

“Developing product is a little bit like playing Battleship,” John Long tells me. “We do our best to get close. But we’re lobbing things over and hoping that we hit something.”

He says it without drama, the way you describe a thing you’ve made peace with. And it would be a perfectly ordinary metaphor — every product person has felt the fog of guessing what a customer actually wants — except that Long doesn’t stop at the guessing. He stops at what happens after the miss. Because the miss, in his telling, is where the trust starts to die.

Long has spent 15 years selling technology, and he’s a particular kind of seller. The kind who digs into the product until he barely needs a sales engineer, who can demo the thing himself because he’s bothered to learn how it actually works. That’s rarer than it sounds. “Some organizations don’t even allow that,” he says — they keep sellers out of the product entirely. He’s spent his career on the other side of that wall, close enough to product to watch the relationship between the two functions either compound or collapse. Now he’s the CEO of Thynk AI, a company building AI agents that handle the parts of selling no one enjoys. But the thing he keeps returning to isn’t the technology. It’s the human seam between the people who build and the people who sell, and how easily it tears.

Start with what it looks like when the seam holds, because Long has lived that too. He describes it almost wistfully. “If you have sales in one silo and product in another silo and the two never meet, product market fit is going to be a disaster.” The inverse — sales and product cross-pollinating — is the only way he’s seen a company nail it. He puts it bluntly: “If the guys developing don’t know what the guys using are actually doing with the tools, it’s not gonna work.” When that gap stays open, the seller is left doing something absurd. “You’re trying to sell ice cubes to Eskimos.” The product does A, B, and C. The customer needs X, Y, and Z. And so, Long says, “I spend 90% of the sales process trying to convince them that A, B and C is actually what they want to buy.” His favorite saying cuts the other way, toward the thing the silos make impossible: “Sell the customer what they want to buy.”

But the slow rot doesn’t announce itself as a strategy failure. It announces itself as friction, and the friction has a sound. Long can reproduce it from memory. The sales leadership preaching down at the reps: “Sell what’s on the truck. Don’t make up things. Don’t sell vaporware. Don’t sell things that don’t exist.” The sales leader carrying complaints up to the product leader: we need the product to do these things, and it’s not doing them. And the product leader, if he’s lost touch with what the customer actually needs, firing back the line that tells you the trust is already gone. “Hey, no, we gave you the perfect product. Quit complaining and go and sell what we’ve built.”

I ask him what the early symptoms are, the things you’d notice before anyone names the problem. He doesn’t reach for a framework. He reaches for the implementation team — the people downstream of every overpromise, the ones who inherit the gap between what was sold and what exists. He voices them, and you can hear that he’s heard this exact lament more than once. “Ah, I wish the sales reps would actually represent the product accurately. I’m having to fix all of their problems. I’ve got customers that are frustrated from day one.” Overpromising, churn, a backlog of broken implementations — these are the visible signs. Underneath them is the invisible one: “this spiral downward of friction, frustration.”

Then we get to Battleship, and the metaphor turns out to be sharper than it first appeared. Because the problem isn’t that people miss. Everyone misses. The problem is what each side is allowed to conclude from a miss.

Watch what happens, Long says, when a sales rep brings real intelligence back from the field — the customer needs it to do these things — and the product team builds toward it and lands close but wrong. “We splashed the ship, but we didn’t hit the ship.” A reasonable outcome. A near miss in a game that is mostly near misses. But the conclusion the product team draws is not reasonable. “The product team inherently says, ‘Oh, the sales rep doesn’t know what he’s talking about. He doesn’t know how to gather requirements. I don’t trust him. I’m not gonna listen to him anymore. I’m doing this on my own.’”

One miss, and the channel closes.

Now run the same miss the other direction. The product team, working from its own instincts, builds something and it doesn’t land. Same result, same splash, same near miss. But the verdict flips entirely. “If the product team develops something and they miss the ship, then they’re like, ‘Well, it’s okay. We got closer.’” The miss becomes a milestone. Foundational. A step in the right direction. “Suddenly it’s okay.”

That asymmetry is the whole thing. The sales rep’s miss is evidence he can’t be trusted. The product team’s miss is evidence they’re learning. Same game, same odds, two completely different scorecards — and the scorecard is what determines whether anyone keeps listening to anyone. Long isn’t bitter about it; if anything, he’s generous to both sides. “We all miss,” he says, twice, like he wants to make sure it lands for each camp. And then the line that defuses the blame entirely: “I genuinely don’t think anyone ever sets out to be like, ‘I’m gonna build a product that really doesn’t do anything.’”

He’s quick to point out the miss isn’t even fully anyone’s fault, because the target keeps moving. “There’s generally a lot of cooks in the kitchen on the customer side.” He acts out the contradiction the product team is asked to satisfy: one customer insists the button belongs in the upper left corner, because that’s where everybody looks. The next person in the same company is just as certain it belongs in the bottom left, for the same reason. “You’re never gonna get it exactly right.” The honest goal isn’t precision. It’s persistence. “Hopefully we’re hitting boats every once in a while. And then we’ve got something solid and we can start to kinda hit around that.” Like Battleship, he says, you eventually sink the ship — but only if both players are still willing to call out coordinates.

Which is why the cure he describes isn’t a process. It’s a relationship. And he has a specific one in mind.

“Inherent in that type of relationship is a foundation of trust,” he says, and then he gets concrete in a way that turns the abstraction into a person. His business partner today — at the AI company he’s building right now — is the same man who ran product at a company where Long was selling 15 years ago. The product guy. The one developing while Long was out selling what got developed. I ask, and the number he gives me lands hard enough that I say “wow” out loud. The two of them have traveled together, he estimates, “well over 100 times.”

Not for offsites. For customers. “We were constantly connected at the hip. I was selling, he was developing, and we had this deep level of trust with each other.” For seven or eight years, multiple times a month, they got on planes together — the seller and the builder, going to see the same customers with the same eyes. “We were cross-pollinating our two worlds on a regular basis every single week. Either I was in with the product team or he was with me on sales calls, one or the other.”

That’s the antidote to the Battleship asymmetry, and notice what it actually requires. It’s not better requirements documents. It’s proximity sustained long enough that neither side can hide behind the wall. When the product guy is sitting in the customer meeting, he doesn’t get to dismiss the sales rep’s intelligence as secondhand — he heard it himself. When the seller is sitting in the product room, he doesn’t get to treat a miss as betrayal — he watched how the sausage got made. The trust Long describes isn’t a feeling they decided to have. It’s a residue, the thing left behind by a hundred shared flights.

What strikes me, listening to him, is that the trust came first and the results followed, not the other way around. Long has had the dialed-in experiences every seller dreams about — the products so well-fit that customers wanted a quote before he finished the pitch, the runs of growth where the scaling never scaled complexity. But when he traces those back, they don’t start with a great product. They start with a seller and a builder who refused to operate in separate rooms.

The spiral he describes — the one that starts with a single near miss and ends with two functions that have stopped speaking — is the default. It’s what happens when you let the wall stand and let each side keep its own scorecard. The companies that escape it don’t escape because they miss less. They escape because someone decided that a miss was a coordinate, not a verdict, and kept playing.

Near the end, Long is describing the AI company he’s building, and he mentions, almost in passing, that his co-founder is that same product guy. The one from the first story. The one he’s flown with more than a hundred times. They scrapped one plan, elevated another, and ended up here — still the seller and the builder, still connected at the hip, fifteen years and one industry later.

He doesn’t frame it as proof of anything. But it is. The whole conversation has been about what happens when sales stops trusting product, and the answer has been sitting in front of me the entire time, in the shape of a man who never let it happen.

Guest Bio: John Long

John Long is the CEO and Co-Founder of Thynk AI, a Utah-based company building AI communication agents that handle the full pre-sales motion — cold outreach, lead qualification, scheduling, and beyond — without a human ever touching the conversation. Rising to prominence in enterprise technology sales over a 15-year career, Long built his reputation not as a manager of sales teams but as the kind of operator who embeds so deeply with product that the line between salesperson and builder disappears entirely. He was once the lone sales representative tasked with opening a brand-new market segment, and over the course of more than 100 trips with his product team, he helped construct what became a multimillion-dollar recurring revenue line from scratch. The product partner he worked alongside on that run is now his co-founder at Thynk AI.

Founded in mid-2024, Thynk AI entered the market with a thesis that most AI SDR tools are window dressing — capable of sending a templated email but unable to hold a real conversation, respond to replies, or carry a prospect from cold contact through to a qualified meeting without human intervention. Long and his co-founder built Eric, Thynk AI’s AI sales agent, to close that gap end-to-end. Eric makes and receives calls, sends texts and emails, conducts live phone meetings, qualifies and disqualifies prospects, and books follow-ups autonomously. The company’s own website reflects the conviction: there is no human contact available until Eric has qualified you. In its first 90 days of operation, the platform generated $13,440,000 in pipeline for its users with no human SDRs and no ad spend.

Long sees AI communication agents as a platform, not a point solution. Thynk AI has already extended Eric beyond outbound sales into customer service, HR, and accounting functions — any workflow where a business currently deploys a human to conduct a structured, repeatable conversation. The company operates from Lehi, Utah, and Long continues to serve as an advisor and speaker on practical AI deployment for growth-stage companies.

Hey,

Thanks for reading this. I mean that. There's a lot of content out there competing for your attention, and you spent some of it here. I hope it was worth it. Even better, I hope it prompted you to think about something differently enough that you'd share it with someone who'd get something out of it too.

I started this podcast because tactics never stuck with me. What stuck were stories — business biographies, autobiographies, the decisions people made and why they made them. The principle only clicks once you know the story behind it.

So I built the thing I wanted to read. Every week I have two conversations with people who build in technology and product. Then I write the essay I wish I could find — one that puts you inside the conversation, through my eyes. What caught me off guard. What I kept thinking about after we hung up. Where the principle actually lives once you strip away the jargon.

I make this for myself first. If you read the way I do, you’ll want it too.

PS — If you want to pitch coming on the show, or you know someone I should talk to, shoot me an email at caden@hey.com with "January752" in the subject line so it gets past my filters. I'm not optimizing for famous guests. I'm optimizing for interesting conversations, even from people who aren't LinkedIn influencers.

Listen to this episode on Spotify or Apple Podcasts

There was a time, Michael Ferranti reminds me, when people who loved Sonos would not shut up about it.

He says it almost fondly, the way you’d describe a friend’s old enthusiasm. The rabid fan base. The audiophiles who treated their speakers as a personality trait. Sonos wasn’t just good equipment — it was a great experience, he says, the kind where everything in the house seemed to talk to everything else without you having to think about it. Everything just worked together. People evangelized it.

“At least until a couple of years ago.”

That clause is the whole story, and Michael lets it sit there for a second before picking it back up. He’s the VP of marketing at Unleash now, an open-source feature management company based out of Oslo, and he’s spent well over a decade in and around dev tools and infrastructure — the kind of person who reads other companies’ engineering blogs for fun and remembers what they said. Which is why the Sonos story bothers him the way it does. Because Sonos, by his account, knew better. They had written down exactly how to avoid what they were about to do to themselves.

“From a DevOps perspective,” he says, “they had an internal engineering blog where they were always talking about, hey, we’re on Kubernetes now, we’re using containers, we’re doing CI/CD, we’re doing all these things, we’re monitoring with Datadog.” He runs through the list like a man reading a résumé that should have prevented a tragedy. By every technical measure, this was a company that understood how to ship software safely — incrementally, in small controlled batches, watching the metrics, ready to roll back.

And then, Michael says — and here his voice picks up a particular relish — “probably because of the pointy-headed business people.”

He catches himself. “No offense.” A beat. “People have accused me of being a pointy-headed business person myself, so I say that with love.” It’s a good line, and he knows it, and it does a real piece of work in the story: he is not an engineer taking a shot at the suits. He is one of the suits, indicting his own kind.

What the business people wanted was a moment. A new set of headphones, unveiled to the market all at once. Not just the headphones — a new version of the hardware, a new mobile app, the whole constellation lighting up on the same day so that anyone who owned all of it would have a single, coordinated, mind-blowing experience. To pull that off, they did the one thing the engineering blog warned against. “They held a bunch of changes that they wanted to make,” Michael says, “until this big bang release.”

He pauses, because we both know where this goes.

“Not surprisingly, since I’m talking about it on this podcast” — a small grin in the voice — “the outcome wasn’t everybody loved it and applauded.” He lets the real sentence land flat and hard. “The outcome was it broke everything.”

It took them months to unwind. And the part Michael keeps returning to isn’t the engineering damage, it’s what the engineering damage cost. The thing Sonos had spent years building — that rabid, won’t-shut-up loyalty — “they took this brand loyalty that they had accumulated through blood, sweat, and tears over the last couple of years, and just flushed it down the toilet.” He wants me to know he isn’t reaching for drama. “I’m really not exaggerating. Their market cap tanked.” Over $100 million in lost direct revenue, by his count — and that figure doesn’t even include the market capitalization or the brand equity, the harder-to-tally erosion of all those people who used to evangelize and now just felt burned.

The diagnosis is brutal in its simplicity. They didn’t follow their own blog.

I ask him how that happens. How a company writes the correct playbook, publishes it, brags about it, and then does the opposite. Michael doesn’t pretend it’s mysterious. “When the CEO says jump,” he says, “you say how high.” The blog was true. The incentives were truer. Somewhere above the engineers who knew how to release software incrementally was a person who wanted the splash, the unveil, the keynote moment where everything works at once — and the closer you sit to that person, the harder it is to be the one who says we should do this slowly, in pieces, where it’s less impressive and far less likely to detonate.

This is the failure mode Michael has built his argument around, and the Sonos story is its cleanest illustration. The instinct toward the big bang isn’t stupidity. It’s seductive. It promises that if you can just get the latest hardware and the latest app and the new product to land together, you’ll deliver something nobody could feel any other way. The trouble is what it requires you to ignore. To make the coordinated experience perfect, Sonos effectively told most of its existing customers — the ones a few generations back on hardware — that they weren’t sure how it would work for them yet. “For everybody else,” Michael says, channeling the bet they made, “people that are on four generations ago, we’re not sure how it’s gonna work yet. So we’re not gonna try to do that now.”

You’re either in the mind-blowing experience or you’re a casualty of it. There is no middle setting on a big bang.

What he wishes they’d done instead is the thing his whole company exists to make easy. “What’s the experience that we’re trying to create,” he says, “and how do we know categorically that we’re creating that experience?” You measure the user experience as you roll the products out. You do it in small batches over time. You build a feature, expose it to a few, watch what actually happens, and keep your finger near the switch. Underneath that is the mechanism — feature flags, the ability to turn functionality on and off in production safely, in a controlled way, without a deployment. And the piece he keeps coming back to, the one that would have saved Sonos, he calls surgical rollback. “If ever there’s an issue, you can roll it back very, very surgically.” Not a months-long unwind. A scalpel, applied to the one thing that broke, while everything else keeps running.

Picture the same launch run the way he describes it. The new app goes to internal users first, then to a small group of customers who like being on the latest and greatest, then to one region, then everywhere — each step measured, each step reversible. The hardware reaches the people on current-generation gear first, where the team is confident, before anyone promises a mind-blowing experience to a customer four generations back. Nothing gets held in a vault for a single coordinated detonation. The release stops being one enormous unobserved bet and becomes a series of small observed ones. And underneath it is the way Michael thinks about a feature across its whole life — he watches it travel from an idea to code to the thing a customer can actually touch, and then he decides what happens to it. “Sometimes I kill the feature because it doesn’t work,” he says. “Sometimes I roll it out globally.” A big bang offers exactly one of those endings and quietly removes your ability to choose between them. By the time you learn which one you got, it’s already everywhere, and the only tool left is the months-long unwind.

The deeper point, and the one that makes the Sonos story more than a cautionary anecdote, is about who holds the knowledge versus who holds the decision. The engineers knew. The blog proved they knew. But the call belonged to people optimizing for a different kind of metric — the launch, the narrative, the moment — and the org chart made sure the people with the safest path had the smallest voice. Michael’s case for feature ops is, underneath the tooling, a case for changing that. For giving the people who understand how software actually behaves a real seat when the irreversible decisions get made. “A developer could be like shrug emoji” if you ask them whether to ship to everyone, he tells me elsewhere — not because they can’t answer, but because the question was never fully theirs to answer alone. Sonos is what happens when nobody with the scalpel is in the room when the CEO says jump.

I find myself thinking about the fans. The ones who used to evangelize, who treated the brand as a piece of their identity, who would not shut up about how well it all worked together. A big bang is supposed to be for them — the grand coordinated experience, the payoff for their loyalty. Instead it was aimed straight at the thing they loved most.

Sonos got their market cap back, eventually. The headphones shipped. The systems got unwound. But Michael’s phrasing stays with me, because it names the part that doesn’t show up on a balance sheet. The loyalty, accumulated through blood, sweat, and tears, flushed in a single release.

You can recover revenue. The people who used to not shut up about you are quieter now.

Guest Bio: Michael Ferranti

Michael Ferranti is the VP of Marketing at Unleash, the world’s largest open-source feature management platform, where he leads go-to-market strategy for a company that has more than 500 enterprise customers, 13,500+ GitHub stars, and 35 million downloads. Rising to prominence in the 2010s through a series of infrastructure and developer-tools companies, Ferranti built a reputation as a marketer who can translate technically dense products — container storage, zero-trust access, feature flags — into category-defining narratives for engineering and platform buyers.

Previously, as Chief Marketing Officer at Teleport, the open-source infrastructure access platform, Ferranti joined in late 2021 and led the company’s marketing organization through a period of rapid enterprise expansion. Before Teleport, he spent nearly four years at Portworx as VP of Product Marketing and Corporate Marketing, where he helped build the category around Kubernetes-native persistent storage before Portworx was acquired by Pure Storage in 2020 in a deal valued at $370 million.

Earlier in his career, Ferranti held marketing and product roles at ClusterHQ and at Rackspace, where he worked in the early days of OpenStack and most recently served as head of marketing for Mailgun by Rackspace, the developer email API. A Virginia Commonwealth University undergraduate, he relocated from Richmond, Virginia to the Paris metropolitan area in 2023. At Unleash, he has been part of the team that tripled ARR over three consecutive years, closed the $35 million Series B in March 2026 led by One Peak with participation from Spark Capital, Frontline Ventures, and Firstminute Capital, and expanded the customer roster to include Lloyds Banking Group, Wayfair, Prudential, and Lenovo.

Hey,

Thanks for reading this. I mean that. There's a lot of content out there competing for your attention, and you spent some of it here. I hope it was worth it. Even better, I hope it prompted you to think about something differently enough that you'd share it with someone who'd get something out of it too.

I started this podcast because tactics never stuck with me. What stuck were stories — business biographies, autobiographies, the decisions people made and why they made them. The principle only clicks once you know the story behind it.

So I built the thing I wanted to read. Every week I have two conversations with people who build in technology and product. Then I write the essay I wish I could find — one that puts you inside the conversation, through my eyes. What caught me off guard. What I kept thinking about after we hung up. Where the principle actually lives once you strip away the jargon.

I make this for myself first. If you read the way I do, you’ll want it too.

PS — If you want to pitch coming on the show, or you know someone I should talk to, shoot me an email at caden@hey.com with "January752" in the subject line so it gets past my filters. I'm not optimizing for famous guests. I'm optimizing for interesting conversations, even from people who aren't LinkedIn influencers.

Under every answer Fin gave, for two years, sat two buttons.

The AI would resolve a customer’s question, list its sources, and then ask: Did this answer your question? Below it, the only two ways to respond. Yes. Or: Talk to the team.

“It was, like, crazy bad UX,” Brian Donohue tells me, walking through it the way you walk through a photo of yourself from 15 years ago. “It was, like, the wrong question to ask at the wrong time.” Listen to the shape of the thing. Did this answer your question? Yes. Or: talk to the team. “You couldn’t say no and continue it,” he says. The interface presumed the conversation was over at the exact instant the whole point was to keep it going. “It was, like, a way no one would ever ask this.”

Brian is the VP of Product for Fin, Intercom’s AI agent for customer support — the thing he’s spent the last two and a half years going, in his own words, “progressively, progressively, progressively, more and more and more” all in on. He’s been at Intercom for 11 years. He’s watched the company carry its support product from the old rule-based bots, “where there’s a little bit of ml” and “mostly deterministic stuff going on,” all the way to a system rebuilt from the ground up around large language models. He’s proud of it. You can hear the pride in the way he narrates the early days — the summer of 2022, before ChatGPT, when one of his ML engineers stood up at a show-and-tell to demo summarizing a support conversation and the verdict was “it just still doesn’t work that well.” And then, a few months later, it did. “It immediately was good enough there,” he says. “That opened the door.”

So when he says the company built Fin from scratch, he means it. They threw away the old bots. They restarted on the new system. “That was ground up, from rebuilding.”

Which is what makes the buttons such a strange thing to find still standing.

They weren’t a corner of the product nobody looked at. “This is anchored into our whole system,” he says. “This is how we calculate resolutions. This is how we charge. It’s a fundamental UX part of the system.” The buttons weren’t a cosmetic afterthought. They were load-bearing. The company’s revenue ran through them.

And the team that built Fin from scratch — the team that prides itself on having thrown the old world away — did not see them. For two years.

“We were blind,” he says. “It was inherited product we were blind to.” He keeps circling the same disbelief, the way you do when you’re still metabolizing it in real time. “Oh, we built Fin from scratch.” A beat. “But no, we didn’t.” His voice catches the way it does when a person hears himself mid-sentence. “We still had parts of the system we were anchoring on, and two years later — oh my God, I can’t believe we still inherited that design and hadn’t challenged it.”

I tell him this is exactly the conversation I wanted. Earlier I’d said something I meant as a compliment and a confession of my own: I’m glad I’m talking to him and not to the CPO. The CPO is a fantastic storyteller, buttoned up and polished, and for good reason. “I want the documentary,” I tell Brian. “I don’t want the blockbuster.”

This is the documentary. A team rebuilds its entire product around the most disruptive technology of the decade, and the thing holding it back turns out to be a design decision they’d already declared finished. Not a hard technical problem. A button. A question phrased wrong, shipped fast, and never looked at again — because, as Brian puts it, “it’s slow, it’s deep in the process system, and so everyone’s reluctant to change it.”

What he says next is the first of three moments in this conversation where Brian admits that the thing he was most certain of was exactly the thing he had to unlearn. The button. Then a process he was sure would never die. Then the way he charged for the whole thing.

What this profile covers

The buttons are the first of three certainties Brian had to unlearn at Intercom. What it took for a team that prides itself on having rebuilt Fin from scratch to finally see the two-year-old design they’d been carrying — and what showed up on the dashboard the day they finally moved it.

The second is the operating model he and Basecamp once independently arrived at: the six-week cycle Basecamp made famous in Shape Up, the sweet spot Brian was sure would never die. He threw it out anyway, along with the triad and stable teams, in favor of a one-line mantra — follow the work — and a cost he names without flinching.

The third is how Intercom charges for Fin. Ninety-nine cents a resolution, billed only when the bot actually answers a customer’s question without escalating to a human. A pricing bet from a company with what Brian calls “a pretty bumpy history with pricing,” and what it collapsed about an entire category of product work he used to do.

Through-line: three things an 11-year intercom veteran was surest of, each one quietly the inherited debt. What he’s learned to distrust about the feeling of certainty itself.

Read more

Listen to this episode on Spotify or Apple Podcasts

Before Issac Hicks built a company that erases tedious work, he spent years watching people fight to keep it.

He tells me about the consulting days. He was at one of the Big Four, parachuting into companies in the middle of acquisitions — his job, specifically, to manage the software migrations and technology transitions that follow when one company swallows another. And the thing he kept seeing, no matter what the project was, no matter what he’d been staffed to, was a particular kind of resistance. A company gets bought. Somewhere four levels up, somebody made a lot of money. And the people on the ground, the ones who actually run the workflows, look at the new systems they’re being asked to learn and dig in their heels.

“They had such, so much pain in what they were doing,” he says, “but at least it was a pain they knew.”

That line stops me. Because it explains something I’d never been able to name. The resistance was never really about the new system being worse. It was about the old pain being familiar. He acts out the internal monologue of the bitter employee: “Oh, so I have to learn a whole new bag of crap that I have to do now? Are you serious?” The crap they already had was at least theirs. They’d built a kind of grim competence around it.

Hicks is an aerospace engineer by training who decided, somewhere along the way, that he didn’t want to pursue that career further. Consulting came next, then a turn that now looks prescient: he started building custom AI solutions before most people knew what that meant. This was the era when you had to design the neural nets yourself — perceptrons, regression analysis, basic sentiment analysis stitched together from a limited vocabulary, all of it before the transformer paper made the whole thing legible to the rest of us. He filed the paperwork for Autonomi in February of 2021. It didn’t take off until years two and three, which is to say, until the rest of the world caught up to where he already was.

So when I bring up the fear — the disruption everyone’s bracing for, the careers built entirely on being willing to do the schlep work nobody else wanted — I expect him to hedge. To do the responsible thing and acknowledge the human cost.

He doesn’t hedge. He reframes.

“I’m really an optimist about the whole AI thing,” he says, “because there’s kind of two ways you can look at it.” The first way is the one we all already know. AI comes, displaces a bunch of jobs, and what are these people going to do? Unemployment skyrockets. What about the working man. He’s not dismissive of it — he just thinks it’s overweighted. “It gets a lot of traction. I think it has a lot more traction than it deserves, and the reason I think it has more traction than it deserves is because it’s fear, uncertainty, doubt. It works well in news cycles. It’s gonna get the views, it’s gonna get the clicks.”

Then the other way. The way he actually lives in.

“If those are already profitable workers,” he says, “how much more profitable could they be if they were doing more meaningful work?” He keeps going, and the questions stack on each other like he’s been waiting to ask them. How much more could you accomplish? How much more market share could you have? How much more productivity could you get as a business owner?

The logic underneath it is almost boring in its sturdiness. A worker you employ is, by definition, someone you make money on — that’s what employment is. So the displacement instinct, the cut-the-headcount reflex, is throwing away an asset you’ve already paid to acquire. “It is more efficient to repurpose labor that is already a culture fit, that is already aligned, that you can already trust,” he says, “than it is to try to just get rid of people and then bring on systems that aren’t proven, that you have to figure out yourself or hire somebody to implement.” The person already inside your company is the cheapest, most trustworthy resource you have. The fear narrative treats them as the cost. He treats them as the gain.

I want to know what the tedious work actually is, the stuff he’s automating away. He doesn’t reach for an abstraction. He reaches for a spreadsheet.

“It just makes life so much better when you don’t have to spend hours doing that mind-numbing, soul-crushing” — he searches for the example and lands on the most ordinary one imaginable — “it’s like, ‘Oh, I’m gonna design a spreadsheet for six hours.’”

He almost laughs at it. “Who wants to do that? Nobody wants to design a spreadsheet. Are you kidding me?”

This is the part of his thinking that I find most persuasive, and it’s the part that has nothing to do with technology. Earlier in our conversation he’d described the math of it — a worker spending two-plus hours a day filling out forms, sending routine emails, checking records to make sure things are validated. Multiply that across dozens or hundreds or thousands of people and you’re talking about tens of thousands of work hours. He frames it as a cost problem, which it is. But then he says the thing that I think actually drives him: “That’s also just a morale problem. Somebody who’s spending two-plus hours a day doing that kind of thing — do you think they like that? Are they likely to stick around? What’s your employee attrition look like?”

And then he does something I didn’t expect. He gets meta with it.

“If that’s how they feel during the day,” he asks, “what are they doing outside of work? What’s their family life like? How are they interacting with strangers?” His voice slows here, the salesman tone gone entirely. “What is that doing for society at large whenever you have a bunch of people who are going through their lives just frustrated with the crap that they have to do day in and day out?”

That’s the moment the conversation stops being about automation and starts being about something older. The tedium isn’t just expensive. It’s corrosive. It follows people home. Hicks didn’t start Autonomi because he loves operational workflows — he started it, he tells me, because “I kind of saw an opportunity to both fill a market need and just kind of remove all the crap that was in people’s lives.” The market need was the business case. Removing the crap was the actual point. “I thought it would be a good thing to do to just help people stop doing stuff like that.”

I recognize the impulse — I was the guy who built the spreadsheet, every time, because someone had to. What Hicks names so cleanly is the trap inside that role: the work was always a tax, never the job.

There’s a popular essay among engineers called “Glue Work” — about the unglamorous coordination labor that holds teams together. Its hardest truth is that the risk of doing glue work is that you were never hired to do it in the first place. You do the necessary, invisible thing, and the org promotes the person who shipped the feature instead. Tedium has always operated this way. It’s necessary, nobody wants it, and the people who absorb it rarely get rewarded for absorbing it.

So here is what Hicks is really saying, underneath the optimism, and it’s the thing the displacement story gets backwards. The jobs AI takes are not the jobs people wanted. They’re the jobs people endured. As Hicks puts it, the core ethos is “just being able to get rid of those really tedious things that nobody really wants to do in the first place, but you have to — and now you can automate those.” Nobody’s calling at career built on dread. They’re calling it a career because there was no alternative, and the dread came bundled with the paycheck. Remove the dread and you haven’t removed the person. You’ve removed the tax they were paying to keep the job.

The fear assumes the tedium was the value. Hicks has watched enough acquisitions and built enough systems to know it was the opposite — the tedium was what stood between people and the value they could actually create. He’s not naive about the transition; he knows real disruption is coming, that some people whose entire identity is wrapped around the drudgery will refuse to relearn and will lose out. But the worker who’s willing to move is worth more on the other side, not less.

Which leaves the question he keeps circling back to, the one that lingered after we hung up. When the crap is gone, what fills the space?

“What else could they have been doing?” he asks. “What’s that backlog of work?” Every company he’s ever walked into has one — the pile of things everyone knew mattered and no one ever had the hours for. The strategy that never got written. The customer problem that never got solved. The thing you kept saying you’d get to.

“What would have taken you a year,” he says, “that you can now do in two or three months?”

The backlog was always there. It was just buried under six hours of building a spreadsheet nobody wanted to build.

Guest Bio: Issac Hicks

Issac Hicks is the Founder and CEO at Autonomi, an AI and automation consulting firm that helps mid-market and enterprise companies make critical work reliably repeatable. Rising to prominence in the applied AI space in the early 2020s, Hicks built Autonomi into a recognized force in business process automation — earning a seat on the Forbes Technology Council — by focusing on a thesis most consulting firms won’t touch: that the biggest source of wasted enterprise spend isn’t bad strategy, it’s the avalanche of tedious, repetitive operational work that consumes employees’ days. His firm has driven over $50 million in wasted spend back to the bottom line across deployments spanning custom applications, AI-enabled workflows, and end-to-end process automation.

Hicks arrived at entrepreneurship through an unlikely path. He earned a Bachelor’s Degree in Aerospace, Aeronautical and Astronautical Engineering from Missouri University of Science and Technology (class of 2016), then spent roughly a year working as an aerospace engineer for the government before pivoting into Big Four business consulting. In that role he specialized in technology implementation for companies undergoing software migrations and acquisitions — work that put him inside some of the most operationally chaotic moments a company can experience. He watched acquired employees dread every transition, buried under work that existed solely because no one had built a system to handle it. In February 2021, he left consulting to found Autonomi with the conviction that the gap between a business problem and a scalable AI solution was bridgeable — and that bridging it was more valuable than any single consulting engagement.

Autonomi operates across the full spectrum of automation maturity: from $5,000 pilot deployments to full-scale engagements starting at $25,000, with a primary focus on companies generating $2 million or more in annual revenue. The firm’s product portfolio includes Autonomy Books, an automated bookkeeping solution built specifically for CPA firms — a vertical where reconciliation and data entry remain stubbornly manual despite being near-perfectly suited to automation. Rather than pursue venture capital and the growth-at-any-cost model that comes with it, Hicks chose to build Autonomi as a profitable, self-sustaining business, retaining the operational control he now helps his clients achieve.

Hey,

Thanks for reading this. I mean that. There's a lot of content out there competing for your attention, and you spent some of it here. I hope it was worth it. Even better, I hope it prompted you to think about something differently enough that you'd share it with someone who'd get something out of it too.

I started this podcast because tactics never stuck with me. What stuck were stories — business biographies, autobiographies, the decisions people made and why they made them. The principle only clicks once you know the story behind it.

So I built the thing I wanted to read. Every week I have two conversations with people who build in technology and product. Then I write the essay I wish I could find — one that puts you inside the conversation, through my eyes. What caught me off guard. What I kept thinking about after we hung up. Where the principle actually lives once you strip away the jargon.

I make this for myself first. If you read the way I do, you’ll want it too.

PS — If you want to pitch coming on the show, or you know someone I should talk to, shoot me an email at caden@hey.com with "January752" in the subject line so it gets past my filters. I'm not optimizing for famous guests. I'm optimizing for interesting conversations, even from people who aren't LinkedIn influencers.

Listen to this episode on Spotify or Apple Podcasts

Paul Glover spent 30 years as “Mad Dog” — a Chicago trial attorney who would do whatever it took to win. That instinct carried him into 33 white-collar felonies and five and a half years in federal prison. He got out in his 50s with no law license and no network. Today his largest coaching client is a billion-dollar distribution company.

“I’m also a recovering lawyer,” Paul says, maybe thirty seconds into the call.

He lists it the way you’d mention a hobby. “I practiced labor law in the city of Chicago for 30 years. I’m also an ex-felon. I went to prison for five and a half years for committing white-collar crimes.” Then he keeps moving, smooth, like the prison sentence was one bullet on a résumé he’s read aloud a hundred times. “Got out in 2001 and decided, since I could no longer practice law, to start a coaching business.”

“Wow,” I say. And then again, because the first one didn’t cover it. “Wow.”

I’d come in with the question I usually save for people who’ve made a hard pivot — the one about limiting beliefs, about what they had to unlearn. I start to ask it. Paul cuts the frame out from under me before I finish.

“When you talk about limiting beliefs, I have a different term for it,” he says. “I call it blind spots.”

The distinction matters more than it sounds. A limiting belief is something you hold. A blind spot is something that holds you, and you can’t see it doing the holding.

“Everybody has blind spots,” Paul says. “They’re called blind spots because we don’t see them, but everybody else does. And every blind spot has a trigger attached to it, and if you don’t know what your trigger is and you don’t know what your blind spots are, you are primed to be manipulated by the world. You will not be able to choose your own course because somebody else will choose it for you.”

His own blind spot was the size of a courtroom. “I had an extraordinarily large ego. I truly believed I was the smartest guy in every room.” He’s not bragging when he says it — he’s diagnosing. The ego came from winning, and the winning came easy, and that was the trap. “Once you become successful, you start to live in your own echo chamber, and people will surround you in that echo chamber doing exactly that, continuing to tell you how good you are. At some point, you’ll believe it. Once you believe it, then you start to fail.”

At trial, they called him Mad Dog. “I would do whatever was necessary to win,” he says. “Unethical behavior was fine with me. I just looked at it differently.” He was good. He was also bored. A trial lawyer, he tells me, is an adrenaline junkie — a performer in a room with a referee and an opponent, and he loved the performance. The problem was everything between performances. “When you’re not at trial, when you’re doing preparation, that’s not adrenaline, that’s drudge, and I hated it. So I started to seek adrenaline, and I got it from my clients, who were not nice people, to be kind.”

They were criminals. Good ones. “Good grifters, they find your blind spots and your triggers immediately, and they pressed mine right away.” What they found was a man from a broken home who wanted to belong. They gave him a group. “But the initiation fee,” Paul says, “was committing crimes.”

He paid it 33 times.

There’s a scene he tells next that I keep turning over after the call ends.

Two trials. The first ended in a hung jury. The second convicted him. He’s standing in front of the sentencing judge, looking at seven years, and the judge offers him a deal — a way to cut the sentence by twenty percent. A year and a half, maybe two years, back. All he has to do is two things. Admit he committed the crimes. And help the prosecutor go after the men who committed them with him.

“And my answer to both of those was no,” Paul says.

He’s already convicted. He’s already going to prison. The math is not subtle — two years of his life, free for the taking. He turns it down anyway, and he tells me exactly why, and the why is the whole man in two sentences. “First, I could not admit I was wrong and got caught. Second, I could not give up the people who were in my group.”

The ego that made him a felon followed him all the way to the chair in front of the judge. The blind spot doesn’t care that you’ve already lost. It just wants to keep you from saying the words.

What broke it wasn’t the sentence. It was the traffic.

For the first two and a half years inside, Paul ran revenge fantasies. He was going to get even with everyone who put him there. He’d accepted no responsibility for any of it. And then he started noticing the men who’d already served their time and walked out — coming back. Returning. To prison.

“That shocked me,” he says, “because why would anybody wanna come back to prison? It’s a terrible place.” He’d watched freedom get taken from him without understanding what it weighed until he saw other men volunteer to lose it again. “When they started coming back, I realized that if I did not change, I was going to become a career criminal, because I would return to exactly the same situation I had left.”

He has a theory about this now, built from the inside. “If you have blind spots and triggers, something has to break the pattern, because otherwise there’s no reason for you to change.” For most people the something never arrives, and they stay the same until they die. For Paul it arrived as a turnstile of returning men, and it was enough.

Here is the part that should not work and somehow does.

A 50-year-old ex-felon walks out of federal prison with his law license revoked — thirteen years before he can even apply to get it back. He has, by his own accounting, narrow options and a personality that has never played well with others. So he reaches for the only tools he kept: he can tell a story, and he has failed at the highest possible level and survived it.

He decides to coach. But coaching, as it’s usually sold, makes him wince. “The concept of coaching, to me, always felt too soft,” he says. “And that’s not who I am, and therefore, that’s not how I could coach.”

What he reached for instead, he found in a book he read in prison. In medieval courts, the king was anointed by divine power, which meant challenging the king was heresy, which meant death. “The one exception to that was the fool,” Paul says. The jester in the gaudy outfit, jumping and dancing at the foot of the throne — we remember him as entertainment. He was something else. “Because they were seen as being crazy, they had an exception to the rule of being able to tell the king the truth. So that psychological safety allowed them to tell the king when they were behaving badly or making a bad decision.”

That, Paul decided, was the job. “I’m going to present myself as that person that cares enough about you to give you the gift of truth.” The branding wrote itself. The No BS Executive Coach isn’t a slogan about being blunt. It’s a man who spent 30 years living inside an echo chamber appointing himself the one voice in the room allowed to puncture someone else’s.

His first proof that it might work came as a reference, or rather two of them. Within two years of getting out, Paul asked a client to vouch for him. The client offered a choice. “He said, ‘The first one is, Paul’s an acquired taste, like cyanide.’” Paul laughs telling me this. “I said, ‘I don’t think I’m gonna use that one. Give me the second one.’”

The second one became his entire philosophy. “Paul is a Sherpa. He will get you to the mountaintop, but he will not carry your pack.”

He means it structurally, not just spiritually. Paul puts half his fee on the outcome. A one-year contract, goals set together, and if the year ends without those goals met, he collects only half his compensation. “I believe I have to have skin in the game,” he says. “If I don’t have skin in the game, then I’ll let you off the hook. If my money’s at stake, I’m gonna put my boot up your tail if you’re not doing what you’ve agreed to do.”

I tell him this is, whatever else it is, excellent positioning — clear about who he’s for and unbothered by everyone else. He agrees without flinching. “If you don’t like the taste, I’m okay with that. It’s not gonna work, I don’t wanna take your money, and I don’t wanna waste my time.”

He is not a life coach. He says this twice, in case I miss it. “I’m a performance coach. I get hired to improve performance, and I will push you to the edge. I will not accept mediocrity.” His clients are already successful — that’s the point, he says, that’s how they can afford him. The work isn’t getting them from struggling to fine. “Everybody can be high-performing,” he says. “That’s no longer the goal. The goal is you wanna be world-class. World-class requires a much different set of requirements and effort.” Most people stop short, comfortable, well-paid, respected. He calls that the comfort zone and tells them, gently, that they’ll never get better inside it.

I ask him what he actually sees when a new executive walks in the door. The answer comes fast, like he’s been waiting for the question.

“They are trying to do too much too soon to make that impression that they believe is necessary to convince the person who put them in the position it was the right choice,” he says. They don’t breathe. They don’t listen. They invent problems so they can solve them. Paul has a 90-day program he runs new executives through, and the first instruction is always the same: slow down.

“Start to talk to the people,” he says. Mine what’s already there before you decide what to build on top of it. Most new leaders got promoted for being doers, and now they’re suddenly supposed to lead — a different skill set entirely. The instinct to do more, faster, is the very instinct that will bury them.

Then he gets to the part I don’t expect. He talks about sleep. About exercise. About family time. “If you’re not gonna take care of yourself physically and mentally, I don’t want you in my program,” he says. He runs a monthly audit — a full 24-hour walkthrough of how his clients spend their time and energy. He wants to know where the hours go. Travel, he tells me, is the worst productivity suck in corporate life. And family gets sacrificed first, always. “People who are promoted sacrifice family first, and that is a short-term — just a — it’s an ignorant way to look at it,” he says. “Your family is your support base outside of work. They are the ones that you should care about more than the job, so don’t shortcut them.”

He advocates for two phones — work and personal — and for turning the work phone off. “That freaks people out,” he says, and something in his voice suggests he enjoys the freaking out. “There’s this thing called voicemail. You’d be shocked how it works.”

The mechanism underneath all of it is the same one that saved him in prison. Something has to matter more than your ego. Something has to break the pattern. “If you’re still self-centered, there’s no reason to change,” he tells me. “It’s when you suddenly realize the impact you’re having on others that gives you the necessary strength to break the pattern.” For his clients, that something is usually their family. For Paul, it was the men coming back through the gates.

I ask him why the people at the very top — the ones who answer to no one but a board — are the ones who hire coaches. He gives me the line that reframes the whole conversation.

“The more successful you are, the more you need a coach.”

Then he reaches back across two thousand years for the picture. A conquering general gets his parade through Rome, the loot and the prisoners marched in front of him, the general himself in a gold chariot behind six white stallions. And riding in the chariot with him, the entire length of the procession, a slave. The slave has one job. “To continually whisper in the general’s ear,” Paul says, “’You are but a man.’ Because that type of success will overwhelm you and start to convince you that you are more than a man, and that means you think you’re infallible.”

That’s the chariot Paul rode for 30 years with no one whispering anything. The echo chamber had no slave in it. Everyone in there told him he was the smartest man in the room, and eventually he believed them, and then he committed 33 crimes and told a judge he’d done nothing wrong.

So he built the thing he never had and rents it out by the year. The man who could not say I was wrong to save two years of his own freedom now makes his living saying it for other people, before the parade, while there’s still time to climb down from the chariot.

It’s an acquired taste. He’s the first to tell you. He’s also, somehow, the only one in the room allowed to.

Guest Bio: Paul Glover

Paul Glover is the No BS Executive Workplace Coach at Paul Glover Coaching, where he works with C-suite leaders and high-performing executives across the United States on performance, accountability, and organizational resilience. Rising to prominence over more than two decades of coaching work following a complete professional reinvention, he became known for a performance coaching model built around blind spots, outcome-contingent fees, and a refusal to allow clients the comfort of self-deception. His largest active client is a billion-dollar distribution organization.

Previously, Glover spent 30 years as a labor employment trial attorney in Chicago, earning a reputation as an aggressive courtroom litigator. His legal career ended in 1995 when he was indicted on 33 counts of white-collar crimes — including kickbacks, bribery, and tampering with government witnesses — and subsequently sentenced to federal prison. He refused to cooperate with prosecutors to reduce his sentence, and served approximately five years before beginning what would become a second career launched from scratch in his fifties.

Released in 2001 with his law license revoked and ineligible for reinstatement for 13 years, Glover rebuilt entirely as a coach, eventually building a national practice. He structures his engagements as one-year contracts with 50 percent of his fee contingent on clients achieving mutually defined goals — a model designed to give him skin in the game and eliminate the incentive to let clients off the hook. His coaching approach draws directly from his own reckoning with ego, echo chambers, and the moment accountability finally broke through.

Glover is the author of WorkQuake™, a book on surviving and thriving in the Knowledge Economy, praised by executive coach Marshall Goldsmith as agitating “the business status quo.”

Hey,

Thanks for reading this. I mean that. There's a lot of content out there competing for your attention, and you spent some of it here. I hope it was worth it. Even better, I hope it prompted you to think about something differently enough that you'd share it with someone who'd get something out of it too.

I started this podcast because tactics never stuck with me. What stuck were stories — business biographies, autobiographies, the decisions people made and why they made them. The principle only clicks once you know the story behind it.

So I built the thing I wanted to read. Every week I have two conversations with people who build in technology and product. Then I write the essay I wish I could find — one that puts you inside the conversation, through my eyes. What caught me off guard. What I kept thinking about after we hung up. Where the principle actually lives once you strip away the jargon.

I make this for myself first. If you read the way I do, you’ll want it too.

PS — If you want to pitch coming on the show, or you know someone I should talk to, shoot me an email at caden@hey.com with "January752" in the subject line so it gets past my filters. I'm not optimizing for famous guests. I'm optimizing for interesting conversations, even from people who aren't LinkedIn influencers.

Listen to this episode on Spotify or Apple Podcasts

I ask Joshua Altman what the first ninety days look like when a company hires him, and he does something I don’t expect. He doesn’t talk about audits or deliverables or brand guidelines. He tells me to get a piece of paper.

“Divide it into story, narrative, brand,” he says. “Write that stuff down for your company.”

He makes it sound simple. Three columns. But then he starts explaining what goes in each one, and I realize the exercise is a trap — the kind of trap a good diagnostician sets, where the patient discovers the problem by trying to describe it.

Story, he tells me, is what you tell your friends at the bar. It has characters, setting, situation. A beginning, a middle, a present — not an end, because “we’re still telling this story.” It’s largely unstructured. This happened, then that happened, and on the way there someone got a phone call. Story is the stuff.

Narrative is harder. Narrative answers questions. “What are we saying about who we are? How do these events connect to our themes? And what should people conclude from our connected stories?”

He lets that last one sit. What should people conclude. I write it down because it sounds like the kind of sentence that reorganizes a company if the founders actually try to answer it.

And brand — brand is everything else. “It’s logos, it’s the website, it’s social media handles,” he says, and then he keeps going past the things I expected. “Your product packaging is part of your brand. If you’re a physical retailer, the music you play is part of your brand.” Giveaway pens. Customer interactions. The whole surface area of contact between a company and the people it touches.

The framework sounds clean when he lays it out like that — three layers, each building on the one below it. But the reason companies call Joshua is that they’ve been building from the top down.

“People call us at the brand stage when they really haven’t figured out the story and the narrative yet,” he says. He’s not frustrated when he says it. He’s diagnosing. “Which makes it much harder to effectively communicate that brand, because if narrative is connecting things to our theme, it’s what people should conclude — brand builds on that.”

I think about all the startups I’ve worked with. The ones that came to me with a polished deck and a hollow center. They had logos. They had color palettes. They had a website that said all the right things in all the right fonts. And when you asked what people should conclude from the company’s existence, you got a silence shaped exactly like the one Joshua is describing.

He tells me about the second framework, the one he layers on top of the first. He calls it the Four Languages Model. “What people read, see, hear, and experience.”

Read is intuitive — text on a page. See starts broader — visuals, video, infographics, signage. Hear is where it gets interesting. “It’s that in-store audio experience where they’re putting a lot of investment right now,” he says. “It’s if you do a branded podcast, if your leadership goes on podcasts.” And then experience, the one that trips people up.

“People tend to think it means big experiential events,” he says. “It does. That’s one part of it. But then there’s also how people experience what they read, see, and hear.”

He gives me the example that makes it click. “We are having the same information,” he says, meaning this podcast, this conversation. “We’re listening to the same conversation, but we have two very different experiences.” Someone listening while walking the dog. Someone watching the video. Same words, different encounter. He extends it to product: “Mobile versus desktop interactions, or app, native app, versus the web browser version on a phone. Two very different experiences with the same product.”

I come from product design and management, and I recognize this immediately — it’s user experience thinking applied to communications. But I’ve never heard anyone frame it as a language. Not a channel, not a medium. A language. The implication being that each one has its own grammar, its own rules for how meaning gets made.

I want to see what happens when the framework meets a real company, so I ask him to walk me through a client engagement. He doesn’t give me a name, but he gives me the pattern.

“Most have to wrestle through it a little bit,” he says, “because they haven’t really thought about it as much.” The problem he keeps encountering is a gap between intent and perception. “What we might be saying, people are coming in cold, we don’t know about your company yet. What we conclude might be very different than what you are intending for us to conclude.”

And then the harder version. “Especially when we’re dealing with founder-led companies,” he says. “It might actually be called Smith Corp., where that founder really has a strong tie to it. There could be a lot of pushback. It’s their baby.”

I can hear the diplomacy in how he phrases that. He’s describing a situation where he has to tell someone that the thing they built — the thing they named after themselves, the thing they’ve been explaining to investors and friends and their mother for two years — is sending a message they didn’t intend. The narrative they think they’re telling is not the narrative people are receiving.

“Narrative is the hardest part of the whole structure,” he says, “because it has to answer questions.” He pauses. “People can go and AI themselves a logo. You can pull a website off the shelf of a template, and even now, AI fill in the blanks for me, make it look pretty. Narrative’s a lot harder. It requires you to really look internally at what you’re doing, because you’re asking to make connections, and that becomes a lot harder.”

This is the sentence that earns the headline. The reason most companies call at the wrong stage is that brand is the layer you can buy. Story is the layer you already have, whether you’ve articulated it or not — it’s the stuff that happened. But narrative is the layer you have to build, and building it means sitting with questions that don’t have comfortable answers. What are we actually saying about who we are? Not what do we wish we were saying. What are we saying.

He uses Apple to show me what it looks like when a company has done the work. Not the obvious Apple — not the keynotes or the product launches, though he gets there. He starts with a detail I’ve never heard before.

“The direction the Apple logo appears when the laptop is closed and facing you,” he says, “was a huge debate within Apple.”

I know he can tell I’m interested, because he keeps going. “That might sound inconsequential, but it’s actually very important, because once you flip the screen up, that’s what everyone in the world sees if you’re sitting in a coffee shop.” The logo serves two audiences. Toward the user when closed, it tells you which way is up. Toward the public when open, it’s an advertisement. Apple went back and forth on this “over periods of product release.”

What I hear in that story is a company where brand decisions go all the way down to the hinge. That’s what happens when narrative is resolved — when you’ve answered the question of what people should conclude. Every subsequent decision becomes easier, because you have a principle to decide against. The Apple logo debate wasn’t about a logo. It was about who the laptop is for in the moment it’s being seen.

I bring up David Bowie, because Bowie is the version of this I think about most. A musician who made a chart-topping album every decade by intentionally reinventing himself. Different look, different sound, different era — but always, unmistakably, Bowie.

Joshua takes the example and turns it corporate. “You can’t get too far ahead, you can’t be too far behind,” he says. The trick is knowing “where to inject yourself as a company, as a business. You don’t have to be on, talking on every topic, because you can’t.” He tells me brands do periodic refreshes the same way Bowie did reinventions — deliberate, timed to the culture, but rooted in something consistent underneath.

“These things can change over time,” he says. “What you’re saying was your narrative when you started two years ago might not be the exact same narrative today, because it will change. It should change if you are doing things right.”

I ask him the thing I suspect a lot of founders are afraid to hear: does that mean abandoning what they started with?

Not quite. “Those core things might not change,” he says. “But a lot of what you do and what people might need to conclude will, and that’s just a natural part of your business growing and being more successful.”

He gives me the Amazon version. “When Amazon was just selling books, he was selling books out of the trunk of his car and putting them in the mail, no one was asking him about the gas mileage of his car.” Now they run Amazon Logistics, and environmental stewardship is something a lot of people care about. The story changed. The narrative had to change with it. The brand followed — not led.

Near the end of the conversation, I try to name the through line back to him. “There’s a ton of things that happen before brand,” I say. “Branding gets a lot easier when you’re very clear on how you’re positioning yourself, how you’re deciding to show up.”

He agrees, and then says the thing I think a lot of companies need to hear but won’t find in any branding deck.

“Sometimes you just have to get something live. It has to go up. You have to start somewhere. And it might not be the prettiest, it might not be the best, but it’s getting something out there.” Fifty percent of what you want, he tells me, is fifty percent more than nothing. “You can always change it. You can grow, you can iterate.”

And then: “We say all the time, there’s no content police.”

He means it literally. There is no authority that will penalize you for experimenting in public, for changing your colors, for posting more or less, for trying something and pulling it back. The only people who can tell you whether your narrative is working are the people receiving it, and the only way to find out is to put it in front of them.

I tell him it reminds me of comedians testing material. The hour-long Netflix special where every joke kills — nobody sees the thousands of hours in dive bars that got it there. “They’re testing out their jokes,” Joshua says. “They’re seeing what works, because the only way to do it is in front of a live audience, because they need to know — does this bomb?”

He’s describing narrative development as a live process, not a boardroom exercise. The comedian doesn’t write the special and then perform it. The comedian performs fragments, reads the room, rewrites, performs again, and the special assembles itself from what survived. That’s what narrative work looks like for a company too — if the company is willing to do it in front of people instead of waiting until everything is perfect.

The piece of paper Joshua told me to get at the beginning — story, narrative, brand, three columns — is still sitting in my head. I think about how many founders would fill in the brand column first, because brand is visible and concrete and feels like progress. How many would leave narrative blank, or write something that sounds like narrative but is actually just story wearing a suit. And how the ones who do the hard work of filling in that middle column — what are we saying about who we are, how do these events connect, what should people conclude — end up with a brand that doesn’t need to be explained. Because the explanation is already built into the structure underneath it.

Joshua started as a news producer, carrying fifty pounds of gear into assignments that a phone handles now. He left journalism thinking he’d go back. Instead he found companies that needed what he’d spent years learning to do — not the gear, not the software, but the ability to look at a set of facts and decide what story they tell, what narrative they support, and what the audience should walk away believing.

The tools changed. The question didn’t.

Guest Bio: Joshua Altman

Joshua Altman is the Founder and Managing Director of Beltway Media, a Washington, D.C.-based communications firm that provides fractional chief communications officer services to technology companies and startups. Rising to prominence over more than two decades in strategic communications, he became known for his Story-Narrative-Brand framework and Four Languages model, which help organizations align what people read, see, hear, and experience into a coherent communications strategy. His client roster spans scrappy startups to federal agencies including the U.S. Department of Justice and U.S. Department of Commerce.

Previously, Joshua served as a multimedia journalist at The Hill, where he covered federal policy across energy, healthcare, immigration, defense, and criminal justice, and reported from the front lines of multiple high-stakes election cycles. His background as a news producer — shooting, editing, and cutting four to five videos per day — gave him the operational reps and editorial instinct that now underpin his consulting work.

Joshua holds an M.A. in Communication, Culture and Technology from Georgetown University and a B.A. in Journalism and Mass Communications from The George Washington University. He is a member of The Telly Awards Judging Council and publishes The Comms Chief on Substack.

Hey,

Thanks for reading this. I mean that. There's a lot of content out there competing for your attention, and you spent some of it here. I hope it was worth it. Even better, I hope it prompted you to think about something differently enough that you'd share it with someone who'd get something out of it too.

I started this podcast because tactics never stuck with me. What stuck were stories — business biographies, autobiographies, the decisions people made and why they made them. The principle only clicks once you know the story behind it.

So I built the thing I wanted to read. Every week I have two conversations with people who build in technology and product. Then I write the essay I wish I could find — one that puts you inside the conversation, through my eyes. What caught me off guard. What I kept thinking about after we hung up. Where the principle actually lives once you strip away the jargon.

I make this for myself first. If you read the way I do, you’ll want it too.

PS — If you want to pitch coming on the show, or you know someone I should talk to, shoot me an email at caden@hey.com with "January752" in the subject line so it gets past my filters. I'm not optimizing for famous guests. I'm optimizing for interesting conversations, even from people who aren't LinkedIn influencers.

Listen to this episode on Spotify or Apple Podcasts

Adam Spector has a wonderful executive assistant. He wants me to know that before he tells this story, because the story sounds ruthless if you don’t know that part first.

“I have a wonderful EA,” he says. “She — I’ve gone through a lot of EAs ‘cause I’ve had a lot of bad EAs, but I have a great one now.”

The great one does a lot of work that involves pulling data from a few different places and centralizing it so Adam can see what his day looks like — meetings, messages, the information a founder needs to absorb before the morning gets away from him. Copy, paste, organize, surface. Useful work. Work that keeps things running.

And Adam told her he was going to automate it.

“I told her a long time ago,” he says. “’I’m gonna probably automate this because it’s something that I don’t think you need to do. It’s a low quality use of your time.’” He didn’t fire her. He didn’t even reassign her. He just built the thing. Had an AI pull all his messages and information and move it to the right place. The work she’d been doing by hand, done by a system he created himself.

Then he says the sentence I keep turning over for the rest of the conversation.

“I would argue she should have built that herself.”

He doesn’t say it with cruelty. He says it the way a coach says you had the open lane and you didn’t take it. The opportunity was visible. She knew the roadmap — he’d told her what was coming. If she had built the automation before he did, she would have owned the product. It would have been her system, running on her logic, something Adam depended on without fully understanding how it worked. Instead, he built it, and now the work is off her plate permanently.

“This is sort of the creative destruction — disruption theory, right? You need to disrupt yourself before your competitor does.” He pauses. “The moment I disrupted it for her, that’s now off her plate, and it’s not gonna come back because I’ve now built it. I’ve disrupted her.”

I ask him to hold that thought, because I want to understand where this intensity comes from. A man doesn’t build a company called Chore — a company that literally does other companies’ back-office work for them — unless he’s been burned by the alternative.

He has.

Adam Spector is a four-time founder who has invested in over two hundred companies. He was a product manager at Twitter. He hosts the Entrepreneurial Excellence Podcast. And when I ask him why he started Chore, the answer isn’t a market thesis. It’s a confession.

“That’s literally why Chore started,” he says. “I experienced this pain myself.” In his previous companies, the pattern was always the same: his technical co-founder went to build the product, and Adam was tasked with running the business. Payroll. Compliance. Taxes. “Or,” he says, “I could spend my time making sure our go-to-market is flawless, making sure we’re getting more customers.”

He couldn’t do both. Nobody can. But the trap is that the operational work feels productive — you’re checking boxes, filing things, keeping the lights on — while the strategic work feels risky and uncertain. So you do the safe thing, and your company dies slowly because nobody’s selling.

I tell him my own version. I tried to run a consulting side hustle and decided I could recreate the accounting software myself. Before AI, even — just stitching tools together. “I ended up spending most of my time doing bookkeeping, and it was distracting from sales,” I say. “That’s the reason that business failed.”

He nods, but he wants to reframe it. “I would actually put it differently,” he says. “You can’t save your way to the future. You need to invest in things.”

He gives me the financial version: money in a bank account versus money in the S&P 500. One earns effectively zero after inflation. The other compounds at ten percent a year. Saving feels responsible. Investing feels risky. But the saver’s money is shrinking, and the investor’s money is working. “It’s the same thing when I invest in spending it on making my podcast better or making my team better,” he says. “Don’t be penny-wise and pound-foolish.”

This is where the conversation turns from operations advice into something sharper. Because Adam isn’t just talking about founders who do their own bookkeeping. He’s talking about employees — specifically, the ones who think their job is to wait for instructions.

“If you wanna sit back and have your manager tell you what to do,” he says, “show you someone who’s gonna be unemployed soon.”

The line lands hard enough that I want to push on it. He pushes further.

“If that is the mindset that you have, would anyone ever promote you?” he asks. “Why do you think you’re owed some promotion ‘cause you’re able to sit in a seat and do some work?” He’s talking about product managers, specifically — I’d mentioned that I hear PMs say it’s not their job to understand how their product works. He says it like he’s stating something obvious. “This is why you won’t have a job in a year.”

What he’s describing is a world where curiosity is no longer optional. Not curiosity as a personality trait — curiosity as a survival mechanism. “The more curious you are, the more questions you ask, the better you will do,” he says. “The more the company will say, ‘This person’s critical for our business.’” And the tools to act on that curiosity are free. He calls Claude Code “the best product managers of all time” and means it literally — a PhD in your pocket, ready to solve whatever you point it at.

“All I need is to have curiosity and a willingness to spend some time to do it,” he says, “and I can get anything I want out of it.”

I bring up the cost of agency. There’s a framework I’ve been thinking about — the most valuable commodity shifts across eras of human history. In the Middle Ages, it was security. During the Industrial Revolution, it was capital. In the information age, it was data. Each era had a ruling class built around whoever controlled the scarce resource. And now the price of agency itself has collapsed. You can exercise agency for free. Ask an AI to explore a problem, get a first draft, form a point of view — all before your manager even knows the problem exists.

Adam takes that and sharpens it. “There is no excuse to say, ‘Hey, I already did my own version of this and I checked it. Here’s what I think is the right choice,’” he says. The old workflow was receive problem, pass it to a teammate, wait for the answer, relay it upward. The new workflow is receive problem, take a first pass with AI, arrive with a recommendation. “My manager’s gonna do the same darn thing,” he says. The implication is clear: get there first.

He tells me about an article he read that morning — a factory in Connecticut shutting down, the last manufacturing plant in a town that used to be built around these factories. Moving overseas, cheaper labor, better technology. His take isn’t sentimental. “There’s no reason why you can’t manufacture great things in America,” he says, “but you need people with the right attitude and mindset to go do it.” The workers, he suggests, were protected by unions and fought change instead of asking the harder question: how do we get better at this than the alternative?

“If you are fighting progress,” he says, “you will lose in the end.”

I sit with that because it’s blunt in a way that most people in my world won’t say out loud. The version I hear in product circles is gentler — we need to upskill, we need to adapt. Adam’s version doesn’t have the padding. Learn the new thing or lose. Adopt the tool or become replaceable. There is no third option where you get to keep doing it the way you’ve always done it and everything turns out fine.

“It’s imperative to have a point of view,” he says near the end of our conversation, and this is the line that reframes the whole thing for me. It used to be expensive to have a point of view. Before AI, forming a strategic opinion on something outside your core job meant not doing your core job — and if you were wrong, you were exposed. Now the cost is nearly zero. You can build a prototype instead of scheduling a meeting. You can run an analysis instead of requesting one. You can arrive with a recommendation instead of arriving with a question.

“If you aren’t bringing your unique perspective,” Adam says, “then why don’t I just have AI do it? What am I paying you as a human for?”

The EA story keeps coming back to me. Not because it’s cruel — Adam kept her on, moved her to higher-value work, made clear he wasn’t replacing her. What makes the story stick is the missed window. She knew the automation was coming. He told her the roadmap. The system she could have built and owned, the system that would have made her irreplaceable, was sitting right in front of her. Someone else built it instead.

“The people who disrupt themselves,” Adam says, “will be the ones who stick around long term, because they’ve now owned a key product that I didn’t build.”

That’s the offer and the threat compressed into a single sentence. Build the thing before anyone asks you to. Own it before someone else does. The price of curiosity has never been lower, which means the cost of not being curious has never been higher.

Guest Bio: Adam Spector

Adam Spector is the Founder and CEO of Chore, a back-office operations company that handles HR, finance, compliance, and equity for venture-backed startups. Rising to prominence as a 4x founder and investor in more than 200 startups since 2011, he became known for his conviction that founders should spend zero time on undifferentiated operational work. Under his leadership, Chore has grown from 7 to more than 40 team members, serving hundreds of venture-backed companies across the United States.

Previously, Adam co-founded AbstractOps, which raised approximately $10 million from tier-one venture capital firms before pivoting in 2022, with its operations arm spinning off to become Chore. Across his earlier three venture-backed companies, he raised a combined $30 to $40 million in funding, with one company acquired for $400 million. He also served as a Product Manager at Twitter before turning full-time to founding and investing.

Adam holds a JD/MBA and a degree from Vanderbilt University. He co-founded the Autopilot Fund, an investment vehicle focused on AI-related data sets, and hosts the Entrepreneurial Excellence Podcast, where he interviews founders on the operational realities of building companies.

Hey,

Thanks for reading this. I mean that. There's a lot of content out there competing for your attention, and you spent some of it here. I hope it was worth it. Even better, I hope it prompted you to think about something differently enough that you'd share it with someone who'd get something out of it too.

I started this podcast because tactics never stuck with me. What stuck were stories — business biographies, autobiographies, the decisions people made and why they made them. The principle only clicks once you know the story behind it.

So I built the thing I wanted to read. Every week I have two conversations with people who build in technology and product. Then I write the essay I wish I could find — one that puts you inside the conversation, through my eyes. What caught me off guard. What I kept thinking about after we hung up. Where the principle actually lives once you strip away the jargon.

I make this for myself first. If you read the way I do, you’ll want it too.

PS — If you want to pitch coming on the show, or you know someone I should talk to, shoot me an email at caden@hey.com with "January752" in the subject line so it gets past my filters. I'm not optimizing for famous guests. I'm optimizing for interesting conversations, even from people who aren't LinkedIn influencers.

Steve Jobs Became a Billionaire Through an Animation Studio

He bought a small graphics company from George Lucas for $10 million and poured in close to $50 million more — over half his net worth at the time. What made Pixar work wasn’t the technology; it was years of relentless pre-production before a single frame got animated. Jobs carried that operating model back to Apple, and it’s the same one quietly running the most valuable companies today.

In November 1995, Toy Story opened, Pixar went public, and by close of the first trading day Steve Jobs was worth about $1.17 billion on paper. I don’t think people realize that Steve became a billionaire through an animation studio. Not a computer company. Not a software play. An animation studio he’d bought from George Lucas for $10 million a decade earlier and then poured close to $50 million more into — over half his net worth at the time.

It’s incredibly hard to become a billionaire in tech. Harder in the movie industry. And that detail reorganized how Jobs spent the rest of his career.

Ten years earlier, 1985. Jobs is thirty, freshly exiled from Apple, sitting on a hundred-million-dollar windfall from selling his shares. He starts NeXT. He buys a small computer graphics division from Lucasfilm. The graphics company bleeds money for years. But something else is happening inside it.

John Lasseter, a former Disney animator disillusioned by the waste of the big studio system, placed an intense focus on relentless iterative pre-production before a single frame was animated.

The method was called a story reel — rough cuts of the film voiced by the animators themselves to test narrative with their peers.

Lasseter called the process “story reboarding” because they didn’t do it once. They did it over and over, screening every few months for a brain trust of senior creatives who gave candid feedback. If the narrative wasn’t working, they went back to the script.

This could take two or three years. Before a single actor was hired for a multimillion-dollar retainer. Before a single frame was animated by Ed Catmull’s engineering team.

It turns out it’s cheaper to make prototypical movies with a small staff of elite creative talent over many years than it is to jump straight into the cost of a six-month production with a bad script.

Jobs stayed mostly out of the day-to-day operations, but by watching Catmull and Lasseter he witnessed a completely different approach to creating world-class products. The principle was simple and non-negotiable: you don’t start production until the narrative is undeniable.

That company became Pixar.

So in 1997, when Jobs returned to Apple as its CEO — ninety days from bankruptcy — he immediately tears everything down and rebuilds how decisions get made. The operating style looks remarkably similar to how he and the team at Pixar worked. And honestly, if I made a billion dollars working this way, I would do it at every company I went to.

At Apple, they didn’t debate ideas. They debated artifacts.

Getting in a room and selling your idea wasn’t part of the culture. Every major feature started as a demo, and for a demo to be useful it had to be concrete and specific.

The iPhone keyboard — they used a device called a Wallaby connected to a Mac to test out the autocomplete function. Just enough to test the interaction and get signal.

When demos went poorly, there was the same stream of constructive criticism, but there was never finger-pointing. The expectation was that there would be a follow-up demo, and the new demo would include a response to the feedback from previous demos. The one essential demo expectation: progress. (Ken Kocienda)

“We always started small, with some inspiration. We made demos. We mixed in feedback. We listened to guidance from smart colleagues. We blended in variations. We honed our vision. We followed the initial demo with another and then another. We improved our demos in incremental steps. We evolved our work by slowly converging on better versions of the vision. Round after round of creative selection moved us step by step from the spark of an idea to a finished product.”
— Ken Kocienda, Creative Selection: Inside Apple’s Design Process During the Golden Age of Steve Jobs ​

Tony Fadell said each team used internal heartbeats — aggressive prototype deadlines to force learning cycles. Tight deadlines force focus. It’s hard to make an end-to-end complicated workflow when you’re given two days to make the next demo.

The demos went through multiple rounds of review and phase gates, progressively moving up the org chart until a final gatekeeper — usually a VP — decided if it was ready to be shown to Steve.

Every feature would eventually make it to him. And he decided which features got greenlit to go to production.

Within two years, this operating model put Apple back in the black. Within the next ten, they became one of the world’s most valuable companies. What had worked for a small animation studio — don’t start production until the narrative is undeniable — now ran the largest corporation on earth.

At Steve’s memorial service, Jony Ive eulogized: “Steve loved ideas and loved making stuff, and he treated the process of creativity with a rare and wonderful reverence.”

The principle had scaled. Not because Steve was a genius who couldn’t be replicated, but because it was an operating model. The creative process treated with reverence. Artifacts over arguments. Pre-production before production. An operating model can be copied.

Brian Chesky heard a version of this story and it reorganized his company.

Before the reorganization, Airbnb was already in trouble. The brand was being tarnished by poor customer experience, random features, and a fractured narrative. Chesky had been doing things the “right way” — the product model, empowered teams — and it wasn’t working. The more people they hired, the more projects they ran, the less the product actually improved, and the more the cost went up.

Chesky had the privilege of being mentored by Jony Ive. One day, while venting to him, Jony showed Brian that Apple was run like a studio. Small number of focused bets. One roadmap of focused products. Designers as architects. A CEO who treated the company itself as a design problem.

Brian said: “I had forgotten about the magic of this design renaissance that Steve Jobs had created at Apple. Everything I was taught about how you run a company was opposite of how Steve ran Apple.”

He made his decision. He wasn’t going to apologize anymore for wanting to operate his company his way. He spent the following years reorganizing Airbnb around these operating principles — principles that treated the creative process with reverence and gave space for the best ideas to surface. One lineage. One idea about how the best creative work gets made. The first movie they greenlit was rebooting the core Airbnb experience. They divested from everything else. No more multiple roadmaps, no more each executive owns their own thing.

By 2025 they reported $12.2 billion in revenue, $4.6 billion in free cash flow. Brian said that’s more free cash flow per dollar earned than Apple or Google — and they did it by not trying to make money. They did it by focusing on the core experience and focusing on one thing: narrative.

This isn’t a personality cult. It’s an operating model. Operating models can be copied.

But I’m not running Airbnb.

Back in 2023, I attempted to operate this way before AI made it cheap. I was doing hybrid design and PM work. I reported to the CTO, and I gained a reputation for getting big projects done and quickly building trust with engineers. But I was doing two jobs, and it was brutal.

Eventually I threw in the towel. I told my CTO I was open to making the switch to one of the full-time roles, and because I wanted to stay strategic and support the design team, I switched to PM full-time. At first it was great — suddenly I had more time to be on top of my responsibilities. But over time, the job became mostly blocking and tackling. Alignment meetings. Decision docs. One-pagers. PRDs. None of these meetings led to meaningful outcomes. Nobody was reading the docs.

I was depressed, and I discovered firsthand that getting in a room and talking it out isn’t a strategy.

Then Claude Sonnet 3.5 came out. AI suddenly got really good at writing, and I started experimenting. I set up a project instruction that said, “You’re my ghostwriter. Don’t make up content. Just interview me, then write the one-pager.” In a tenth of the time, I was creating memos that gave clear descriptions of my intent. I started using Granola for meeting notes, and my mental bandwidth freed up. Suddenly I had time to work the way I wanted to work — to craft my own narrative of what I thought the product should be.

So I immediately started making demos and getting them in front of stakeholders and customers.

One day I was shadowing another PM on a customer call. His demo was not going well. The customer was in the wrong segment. The prototype had nothing to do with her job. The interview was dying. I messaged the PM on Slack: “When you’re done, can I have a few minutes at the end?”

I spent the next five minutes pulling up that customer’s actual data and loading it into my prototype. He hands the mic over to me. I send her a link and she opens it.

“This is nice. Wait — is this my data? Are these my customers? I can see all these invoices? Yeah, this is what I’ve been asking for. When are you gonna make this?”

The customer sold herself because the prototype had her data, her workflow, her problem. The narrative was right, I understood the problem, and the artifact proved it. From that moment on, I knew I was never going back.

AI didn’t change the game. It changed who could play.

Making demos at the volume and speed required to discover the right narrative used to be psychologically and operationally brutal. It involved overcoming apprehensions about committing time and effort to ideas you aren’t sure are right, exposing rough work to colleagues who level pointed criticism, knowing that almost all demos fail in the dead-end sense. Remember when it took two weeks to make a janky Figma prototype just to test one idea?

It isn’t anymore.

I did five full prototypes of an AI-native workflow in five weeks — with backends and everything. The first three, I couldn’t get them to work. Threw them away, and it didn’t hurt to throw them away because AI did the grunt work to set them up. By the fourth, I was getting interest.

By the fifth, two VPs were offering me engineers. Developers were asking to join. target users sold themselves mid-demo. My demo was greenlit and officially on the roadmap. Not a single PRD written. It wasn’t talked about in an off-site. It happened because you don’t need to ask permission to do this kind of work.

The artifact argues better than you ever could. Leadership just means you have followers. As long as it works and it’s exciting, people will follow you.

There’s one objection left, and it’s the real one.

“That’s great, Caden, but you’re technical. You know how databases work. How am I supposed to make demos if I studied graphic design?”

So let me tell the story of Jeremy Fry.

Fry made his fortune selling motorized valves for industrial pipelines. But he was not a pipeline man at heart. He was a builder of things that didn’t exist yet. He discovered a promising young talent from a local university and took him under his wing.

One day, the young man went to tell Jeremy about his amazing idea — likely looking for advice, maybe fishing for a compliment, secretly hoping to impress his mentor. Jeremy didn’t ask for a plan. He didn’t ask for a sketch. He pointed to the workshop. “You know where it is. Go and do it.”

At some point they needed to weld something. The young man didn’t know how to weld. He asked if they could hire a welder. Jeremy didn’t blink. He pointed to the welding equipment. “There’s the welder. Go weld it. Figure it out.”

He suggested they bring someone who knew about hydrodynamics just to be sure. Jeremy pointed at the lake. “The lake’s down there. The Land Rover’s over there. Take a plank of wood, drag it through the water, and look at what happens.”

The young man Jeremy took under his wing was James Dyson.

Dyson studied art. Not engineering. Not physics. Art. His first cyclonic vacuum cleaner was built from cereal packets and masking tape. He didn’t fully understand the physics behind it yet. He built it first and learned second — roughly ~5,000 prototypes over five years, before the internet, before AI. And now he owns one of the world’s most impressive engineering companies, employing over ~4,000 engineers and designers.

The credential did not make the invention. The obsession with the narrative did.

Dyson said: “After the idea, there’s plenty of time to learn the technology.”

The companies and the people in these stories share one operating principle. They didn’t start with the best tools. They didn’t start with the right credentials. They started with a narrative they believed in and then iterated relentlessly — in pre-production — until the narrative was undeniable. Then they let the artifact argue for them.

AI has given everybody a camera. It can write the PRD, make the design, ship the code at the median professional level. So why is success still concentrated? Because the best filmmakers spend their time on everything that happens before the camera turns on. The concept. The framing. The narrative. The sequencing. By the time they go into production, the movie has already been made on paper.

It was never about the camera. It was always about the person willing to stand away from it long enough to find out what the story was.

Diagram: My AI Native Design Process

About: Caden Damiano

Caden Damiano is a software designer and product manager who has spent his career untangling problems in industries most people overlook — tertiary finance, real estate technology, working capital for agriculture, and financial operations for small and mid-size businesses. He hosts Way of Product, a podcast and Substack newsletter where, over eight years and 180+ episodes, he has interviewed designers, PMs, and engineers about how good work actually gets done.

PS — If you want to pitch coming on the show, or you know someone I should talk to, shoot me an email at caden@hey.com with "January752" in the subject line so it gets past my filters. I'm not optimizing for famous guests. I'm optimizing for interesting conversations, even from people who aren't LinkedIn influencers.

I ask Adam a hypothetical, the kind that almost always gets a hedged answer.

Could he have started Pentane — his profitability operating system, three years in, used by e-commerce founders to figure out whether they’re actually making money — if he hadn’t spent the decade before it running BottleKeeper?

“Absolutely not,” Adam says. “No way.”

No throat-clearing. No “well, probably not, but you could argue.” Just the flat refusal. He says it the way you say something you’ve already considered from every angle and stopped re-litigating. The certainty is the kind that only comes from having tried to imagine the alternative and failed.

Pentane is a profitability OS. The phrase sounds modular and abstract, the kind of thing pitched at a SaaS demo day. But the actual product is something simpler than that: it answers the question most e-commerce operators don’t have a clean way to ask, which is whether the next ad dollar makes them money or loses them money, and why.

Adam built BottleKeeper from 2013 onward — a beverage insulator brand that grew from zero to $60 million in total sales and exited via private equity. He lives in Montana, does hard physical things in the woods because he believes adversity is a muscle you have to train deliberately. He’s been on Shark Tank. He has the operator’s posture of someone whose CV is mostly stories about the hours nobody filmed.

The Pentane thesis is that he could not have built Pentane any other way. Not on a whiteboard. Not from market research. Not from talking to other operators. Only from being the operator who’d run out of answers.

“I was CEO of a company with no employees doing $8 million a year,” he tells me, and the line lands without performance. He isn’t bragging. He’s establishing the conditions. “I literally did everything — all the customer service, all the paid ads, built the campaigns, spent millions in ad budget, did the creative, built the website.”

He qualifies it a beat later. “My cousin and I — he was my partner, he did most of the finance and shipping and fulfillment and things like that.”

Two people. Eight million in revenue. The math of that is the whole story.

The Facebook video ads moment came in August 2014. Adam shot a video of the product in action — the kind of thing that, in retrospect, was the inflection. Revenue went from two thousand a month to forty to sixty to eighty to a hundred and fifty.

“We sold out of product and we just chased that for years,” he says.

In those first three years he didn’t need systems. He couldn’t spend the ad money fast enough. The growth was hosing him down. WordPress, then WooCommerce, eventually Shopify. The systems were unnecessary because the problem was unaddressed.

Then 2016, 2017. CPMs going up. Returns coming down. He saw it the way anyone in paid media that window saw it — the loose-attribution years closing, the spreadsheets getting more honest. He was about to hire his first team member. The slack in the business was disappearing.

“I needed to get a much better handle on the decisions I was making around what to spend, how much to spend, where to spend it, how it needed to return in order for us to be profitable,” he says. “’Cause we had to be profitable. And what happened if we ran a sale, or what happened if I increased prices — which is something we did really aggressively. And then as we hired people, how was I going to ensure that our customer acquisition and revenue was built in a way that could pay for those people, so we weren’t just spending into a hole.”

The math didn’t exist anywhere he could find. So he wrote it. In spreadsheets, for himself, as the CEO who had nowhere else to send the question. He was answering questions, he tells me, that he “couldn’t find answers to anywhere else.”

That’s the part most product-origin stories skip. Adam didn’t start by trying to solve a market. He was trying to not run out of money. The spreadsheets weren’t a product. They were a way of staying alive.

The company sold. A year after the acquisition, he got bored.

“I went to companies I had invested in and asked if I could help,” he says. “Realized they had the same problems. They just didn’t have the system to help solve the problem and answer the question. So I just rebuilt what I had already done in them and it completely changed them.”

That’s the moment the survival math became a product. Not because he had a vision. Because three founders he respected were drowning in the same way he had been, and his hand-built thing pulled them out.

“I built the thing because I had to,” he says when I ask him to describe Pentane’s actual genesis. “Because I had companies that were using it and it dramatically impacted their net profit outcomes.”

The genesis is causal, not creative. He didn’t have an idea. He had a discovery.

He keeps coming back to the way finance and marketing speak different languages — that gap is where companies bleed. Pentane lives in the gap. The math is provided by the system; an AI layer applies Adam’s mental framework to the operator’s specific situation. The equations don’t come from the model. The model isn’t allowed to invent them.

“It can do math really well,” he says of AI, “but it’s freaking awful at creating the equations if they’re not entirely logical.”

This is the technical detail that doubles as a worldview. You don’t let the AI decide what to measure. You let the operator who’s lived the problem decide what to measure, and you let the AI execute against that decision faster than the operator could.

Three years in, Adam is at a different point on the curve. He’s rebuilt the Pentane product three times by now. V1 was the dev shop he handed fifty thousand dollars to, with a spreadsheet and an instruction: make this. It took the money and produced functional software that made perfect sense to Adam and no sense to anyone else.

V2 took nine months. Better, still not great.

V3, the one his customers are testing now, he built in a weekend.

“I just recreated our entire platform in three days,” he says, and his dev team’s response was “holy hell, this is incredible. They’re fully in support of it.”

He showed it to a customer the day before our recording. The customer’s response, verbatim: “Holy shit, this is so much better. Can I have this now?”

I tell him about the equivalent moment in my own work — pulling a client’s data into a prototype, sending them the link, watching them realize they’re finally looking at the thing they’ve been describing for months. The feedback loop collapses from quarters to minutes. The fidelity arrives at conversational pace.

But Adam frames the speed in a way I don’t want to lose. The reason he can rebuild Pentane in a weekend isn’t the AI. It’s the two and a half years of trying to build it and getting it wrong.

“I don’t know what to tell the AI to do unless I have the last two and a half years of breaking it and screwing it up,” he says.

The acceleration is real. The acceleration is downstream of the operational pain that came first. AI didn’t compress his timeline. His timeline compressed his AI.

Near the end of the conversation we’re talking about something else — DoorDash, whether a logistics platform could vertically integrate into restaurant management software now that the tooling exists — when Adam reaches for an image that I think is the real thesis of his career, and the real reason Pentane exists at all.

“DoorDash probably can spin up that vertical,” he says, “but only because they’ve spent the last 15 years with the people at the top of that company chewing on glass. Almost failing over and over and over to get the product to where it is today.”

Chewing on glass. The verb is grotesque on purpose. It’s the part of the operator’s experience that doesn’t make it into the case study, what gets sanded off when the story gets retold for the press release. And it is, in Adam’s worldview, the only reliable source of product taste.

There is no shortcut to it. There is no AI that can simulate it. There is no consultant who can bottle it.

You eat the glass, or you don’t get the taste.

I think about what that means for everyone now standing at the edge of vibe coding with a copy of Cursor open, building the thing they always wished they had. The tools are there. The math is cheap. The aperture is enormous.

But the question is the one Adam started with. Have you lived the problem? Have you sat at a kitchen table at 2 a.m. trying to figure out whether the next thousand dollars in ad spend is going to pay for itself? Have you watched the CPMs climb and felt the slack in the business disappear?

If you have, the AI is a multiplier on something real.

If you haven’t, it’s a multiplier on a guess.

Adam built Pentane because he had to. The mental model he was selling was the one he’d needed in order to survive. He didn’t get the taste from a book. He got it from the years.

The rest was just figuring out how to put the years in a box.

Guest Bio: Adam Callinan

Adam Callinan is the founder and CEO of Pentane, a profitability operating system for e-commerce and direct-to-consumer brands. Pentane emerged directly from the decade Callinan spent building BottleKeeper — a beverage insulator he co-founded with his cousin in 2013 — from zero revenue to $60 million in total sales and a private equity exit, running customer service, paid advertising, creative, and the website almost entirely himself. The core insight behind Pentane: most e-commerce operators are drowning in dashboards but can’t answer the one question that matters — are we profitable, and why — because no one has codified the right equations for them.

BottleKeeper’s growth was neither gradual nor accidental. In August 2014, when Facebook launched its video ad platform, Callinan shot a clip of the product in motion and watched monthly revenue spike from $2,000 to $40,000 to $60,000 to $80,000 to $150,000 in a matter of months. He spent the next several years doing it almost entirely himself — handling customer service, paid advertising, creative, and the website — while his cousin managed finance and fulfillment. The company appeared on Shark Tank before eventually selling to a private equity buyer.

Callinan lives in Bozeman, Montana, where he pursues hard physical experiences outdoors as deliberate mental conditioning — a framework he traces directly to resilience under business adversity. He actively mentors founders and business owners.

Hey,

Thanks for reading this. I mean that. There's a lot of content out there competing for your attention, and you spent some of it here. I hope it was worth it. Even better, I hope it prompted you to think about something differently enough that you'd share it with someone who'd get something out of it too.

I started this podcast because tactics never stuck with me. What stuck were stories — business biographies, autobiographies, the decisions people made and why they made them. The principle only clicks once you know the story behind it.

So I built the thing I wanted to read. Every week I have two conversations with people who build in technology and product. Then I write the essay I wish I could find — one that puts you inside the conversation, through my eyes. What caught me off guard. What I kept thinking about after we hung up. Where the principle actually lives once you strip away the jargon.

I make this for myself first. If you read the way I do, you’ll want it too.

PS — If you want to pitch coming on the show, or you know someone I should talk to, shoot me an email at caden@hey.com with "January752" in the subject line so it gets past my filters. I'm not optimizing for famous guests. I'm optimizing for interesting conversations, even from people who aren't LinkedIn influencers.

Eric Ries helped invent the playbook a generation of startups used to build fast. Incorruptible is what he learned in the years he spent watching many of those companies become unrecognizable — and the governance structures founders can put in place to prevent it. Your can get your copy here

We’re a few minutes into our conversation when Eric tells me a story about a founder he was advising.

The founder was in earnest. He wanted to know how to bind his company so the technology they were developing, something serious, something medical, would only ever be used to cure people — not kill them. It was the kind of question you ask when you’ve already imagined the version of yourself that wouldn’t ask it.

Eric had been listening. But he had to wrap; he was due at an event in honor of a different founder, a man he’d advised for 10 or 15 years. The young founder was curious. What kind of event?

Eric watched people stream in. A retirement, sort of, he said. Look — there are people at this event who this founder had to fire. They’ve come back to celebrate.

“Mad respect,” the young founder said. “That’s so rare. That’s the kind of company I want to be.”

“You’re not hearing me, man,” Eric said. “This isn’t a party. It’s a wake. He doesn’t work there anymore.”

There’s a beat in Eric’s telling where he says, “He’s like, what?” — and you can hear him reaching for the right way to land what comes next. Because what he had to say was the bridge from one founder’s career to the question he gets asked every week now.

“Yeah,” Eric said. “Even though he made all this money for all his investors, they wanted more, and they ousted him.”

“Is that gonna happen to me someday?” the founder asked.

“Yeah,” Eric said. “That’s what I’ve been trying to tell you this whole conversation. This whole system, by default, unless you take the protective action early — this is what happens to you.”

The founder put it to him this way: Is it possible to build an incorruptible organization?

“Good news, bad news,” Eric said. “Yes. I will tell you how. But you’ve already taken some of the steps in the wrong direction.”

That’s the line that won’t leave me.

Not because it’s clever. Because it inverts every assumption I had about how good companies go bad. I had assumed corruption was a thing that happened to companies later — at some inflection point, after the IPO or the acquisition or the second growth round. That if your founder was good, your culture was strong, and your values were clear, you’d be fine until then. That you could see it coming, the way weather comes from a long way off.

The first chapter of Incorruptible is about Sol Price, who built FedMart and mentored Jim Sinegal of Costco, and who was eventually ousted by his own board, who didn’t want to operate the company the way he wanted to operate it. They wanted to extract value. The system rewarded them for it. What Eric will show you over the rest of the book is that this isn’t a story about one bad board. It is a story about a default state.

Eric Ries has been at the center of the startup movement for 15 years. The Lean Startup made the Minimum Viable Product a household term among the kind of households that have whiteboards in them. He went on to found the Long-Term Stock Exchange, a registered U.S. exchange built for companies that want to opt out of quarterly thinking. A startup law firm. An AI research lab with Jeremy Howard. He has had a particular vantage on the last decade and a half.

“I’ve seen the good,” he tells me. “And I’ve seen the value that’s been created. And I have seen the dark underbelly too. Companies that are being destroyed of their own success.”

He says it the way someone reports something they’ve watched too many times to be surprised by anymore.

He tells me about going to dinner with a group of friends two nights in a row. Two different cities. Both restaurants highly recommended.

First night, the friend who’d picked the place took one bite, set down his fork, and asked the table: “Did private equity take over this restaurant?” Someone pulled out a phone. Yes. The new owners had bought it some months back.

Second night. Different restaurant. Different city. Different recommender. Same first bite. “Is this the same damn private equity firm?” Different firm. Same taste.

“We’ve all had this experience,” Eric says. “Companies that get acquired, that go public, they get bought out — where they just lose that special spark. What made them worth backing and trusting in the first place.”

You can taste it. That is what’s interesting. The thing that’s happened to the company shows up in the food.

The mechanism is what Eric is interested in. Not the symptom. He wants you to understand what changes between the moment a place is good and the moment it isn’t — because the same thing happens at every scale, in every industry, and almost none of the people inside it know it’s happening to them.

To show me how it works, he takes us back to the 1940s. Robert Wood Johnson II, the second-generation owner of Johnson & Johnson, is planning to take the company public during World War II. He’s worried about what that will do to the company over time. So he writes a document, the Johnson & Johnson Credo, that lays out the company’s fiduciary commitments. Patients first. Then doctors and nurses. Then employees. Then communities. Investors last.

The exact opposite of what we now teach as the corporate governance best practice.

He worries people will forget. So he has the credo carved into 10-foot-high limestone blocks and installed in corporate headquarters, where they still stand today. Every person who works there walks past the credo on their way in and on their way out.

For 40 years, executives walked by those blocks. During the same window, the company’s marketing leaned heavily on the credo and MBA case studies held it up as exemplary. Johnson & Johnson also knowingly sold baby powder mixed with cancerous asbestos. And tried to cover it up.

“We know that they tried to cover it up,” Eric says, “because of course these things always come out in litigation. And now we have the internal documents.” A pause. “The same people who put asbestos in the baby powder and tried to cover it up walked by the credo every day.”

The values were carved in stone. The incentives moved. The values lost.

This is where I expect Eric to land on a moral argument. Where he tells me what those executives should have done.

He doesn’t.

He says the executives almost certainly believed they were in compliance with the credo. That they assumed someone at a higher pay grade had worked out how the metrics they were chasing aligned with the values on the wall. That the system they were operating inside had quietly collapsed the distinction between the two.

“This whole modern business philosophy that we’ve all come to live in,” he says, “that puts investors first, that preaches an extraction of value rather than the creation of value — I think that whole way of doing business is corrupt. And I think most founders agree.”

He’s not arguing the executives were bad. He’s arguing they were operating inside a system that produced this outcome by default. The credo was a sign. It was not a structure. And a sign cannot hold a roof up.

The young founder Eric was advising — the one trying to figure out how to make sure his technology only ever cured people — had assumed his good intentions were the structure. That because he meant well, the company would mean well. Eric’s argument, the one that landed so hard, is that this is exactly backward. Good people do not protect organizations from misaligned incentives. They are the ones eaten by them.

The corruption is not a betrayal. It is what the default settings produce.

So when Eric says “you’ve already taken some of the steps in the wrong direction,” he doesn’t mean the founder has done anything wrong. He means the founder has signed a standard incorporation, accepted a standard investor structure, agreed to a standard board composition, and quietly assumed those defaults are neutral. They aren’t. Each of them is a bend in the road. Each of them tilts the company, by a few degrees, toward the wake at the end of the founder’s career.

“Build something worth protecting,” Eric says, “and then actually protect it.”

The corollary is this: there are other defaults available.

Eric tells me about a couple named August and Marie Krogh, who lived in Denmark in the 1920s. August had just won the Nobel Prize. Marie had been diagnosed with diabetes — at the time, a death sentence. They were on a lecture tour of North America when, at one of the dinners, a scientist mentioned to Marie that someone in Canada had figured out how to synthesize insulin.

They went to Canada. They worked out a license to bring the technology back to Denmark.

And then they did something specific. They built the new venture, which they named Nordisk Insulin Lab, as a nonprofit foundation that owned a for-profit subsidiary. A structure called an industrial foundation. They did it because they were worried about pricing power. About what would happen, years from now, if someone realized that a lifesaving drug could become power over the people whose lives depended on it.

That structure is still standing. It’s why Novo Nordisk exists. It is the structure behind Ikea and Hershey, behind several companies you’ve interacted with without realizing the bones underneath were unusual. And here is the part Eric saves for last: companies with this structure are six times more likely to last 50 years than conventionally structured companies.

A founder hears this and asks his lawyer. The lawyer says, oh, no — that’s an old-fashioned thing from Denmark. We don’t do that anymore. We have a much better set of best practices.

Eric, to me, with a small dry smile in his voice: “These advisors may indeed be very smart. But are you sure you’re smarter than a Nobel laureate?”

What I’ve come away with isn’t a list of governance structures. It is a recalibration.

I had been thinking of corruption as a thing companies fell into. A late-stage problem. Something that arrived with the wrong investor, or the wrong CEO, or the wrong acquirer. Eric has me thinking about it the way he thinks about Minimum Viable Products — as something the system produces by default unless you intervene. The intervention isn’t a value statement. It is structural. It is something carved into the company’s bones before the pressure arrives, because once the pressure arrives, there is nothing left to carve into.

This is what the headline means, the one Eric keeps trying to land on the young founder in his office: corruption isn’t the inevitable price of scale. It is a choice you make before you know you’re making it. Every founder who hasn’t architected against it has, by the silence of that omission, chosen it.

Eric ends our conversation the way he ends his book.

“Build something worth protecting. Then actually protect it. So when the pressure comes, when the temptation comes, when the rain comes — the roof is still there.”

That’s the line I keep coming back to. Not the credo on the wall, not the values in the deck, not the founder’s intentions — the roof.

Guest Bio: Eric Ries

Eric Ries is the author of The Lean Startup (2011), The Startup Way (2017), and Incorruptible: Why Good Companies Go Bad, and How Great Companies Stay Great (May 26, 2026). The Lean Startup — which introduced the Build-Measure-Learn feedback loop and the concept of the Minimum Viable Product — has been translated into nearly 30 languages, became required reading at Y Combinator, and established the dominant framework for product development and entrepreneurship for the better part of fifteen years. Ries co-founded IMVU, the social avatar platform, in 2004 with Will Harvey, where he first developed and applied the customer development practices that would later become the methodology.

In 2011, Ries outlined the idea for a fundamentally different kind of stock exchange inside The Lean Startup. He spent the better part of a decade making it real: the Long-Term Stock Exchange (LTSE) received SEC approval as a national exchange in 2019 and launched trading in September 2020, designed expressly for companies committed to long-term value creation over short-term shareholder extraction. He has since co-founded Answer.ai with Jeremy Howard of fast.ai — an AI research lab focused on practical applications — and founded Virgil, a startup law firm designed around founder needs rather than billable hours.

Incorruptible draws on more than 200 years of case studies — from Johnson & Johnson and Costco to Novo Nordisk and Ikea — to argue that the governance structures most companies adopt by default are engineered to destroy the values that made them worth building. Ries’s thesis: companies that last aren’t those with better culture decks, but those whose founders protected the organizational structure before they lost control of it.

Hey,

Thanks for reading this. I mean that. There's a lot of content out there competing for your attention, and you spent some of it here. I hope it was worth it. Even better, I hope it prompted you to think about something differently enough that you'd share it with someone who'd get something out of it too.

I started this podcast because tactics never stuck with me. What stuck were stories — business biographies, autobiographies, the decisions people made and why they made them. The principle only clicks once you know the story behind it.

So I built the thing I wanted to read. Every week I have two conversations with people who build in technology and product. Then I write the essay I wish I could find — one that puts you inside the conversation, through my eyes. What caught me off guard. What I kept thinking about after we hung up. Where the principle actually lives once you strip away the jargon.

I make this for myself first. If you read the way I do, you’ll want it too.

PS — If you want to pitch coming on the show, or you know someone I should talk to, shoot me an email at caden@hey.com with "January752" in the subject line so it gets past my filters. I'm not optimizing for famous guests. I'm optimizing for interesting conversations, even from people who aren't LinkedIn influencers.

Tyler has six agents running at once.

He’s walking me through it. There’s a 36-inch monitor in front of him, and on it: Conductor, a desktop app he tells me a team built in Rust. Inside Conductor, his repo. Off that repo, multiple Git worktrees, which he describes as parallel clones of the same codebase. In each worktree, a Claude Code instance. One is building a feature he’s been planning. Another is cleaning up tech debt. A third is on research. A fourth is doing new work he wants to fold in before he comes back to the first. And in another window, almost as an afterthought, a chief of staff agent managing his email, his calendar, his Slack operations channels.

“I want that thing running as often as I can get it running,” he tells me, by which he means his $200-a-month Claude Max account. “I want it running 24/7.”

He’s not bragging. He’s stating a budget logic. If you’ve already paid for the compute, the question is what fraction of the hour the compute is actually doing work. Most people, he implies, gently, are running maybe ten percent. He is running it like a small factory.

Tyler Wells spent 25 years in engineering. Skype, Microsoft, Twilio, where he stayed for seven and a half years and left as a Senior Director. He oversaw large engineering organizations and stopped writing code somewhere along the way. He went back to building in 2021 because he missed it. He is now co-founder and CTO of BrainGrid AI, three people total, and one of those people is, by his own description, running fleets of agents as a normal Tuesday workflow.

I ask him about the economics. Not the cost of compute, which is the obvious version of the question, but the cost of not using compute. The cost of the alternative.

He has a clean answer.

“I mean, I think it’s way more expensive now to talk about it, right?”

There’s a small beat after he says this, like he wants to make sure I heard it the way he means it.

“It’s — yeah. Think of two Silicon Valley engineers and a PM sitting in a room discussing what they want. That’s an expensive burn.”

He sketches the alternative the way someone draws a stick figure.

“Whereas the PM could’ve just sat there with, hey, I’ve got this idea, let me go prototype it. Boom. Oh no, that doesn’t quite work. Okay, let me fix it. Oh okay, there it is. Great.”

There’s a way to hear that as glib. I don’t think it is. The “boom” and the “okay” aren’t doing rhetorical work. They’re doing time-compression work. Tyler is telling me that the loop between have-an-idea and see-the-idea-running used to be measured in weeks at the absolute fastest, more often in months, and now it’s measured in the time it takes to type a paragraph and wait for the agent to finish a build.

This is the part of the conversation where the economics flip in your head, if you let them.

For most of the history of software, the expensive thing was building. Engineering was the biggest line item on the P&L because building took the most time, the most specialized people, and the longest feedback loops. Talking was cheap because talking was triage, a way to figure out what you should be building before you spent the expensive thing on it. Meetings, whiteboards, spec docs, pitch decks: all of these were optimizations on the build budget. You talked so you wouldn’t build the wrong thing.

Tyler is saying that ratio has inverted.

Now talking is the thing with the highest cost-per-unit-of-outcome, and building has the lowest. Which means the structures we built to optimize for the old ratio, the planning meeting, the executive review, the “let’s circle up on this next week,” the three-engineer-and-a-PM whiteboard, are now where the budget is actually leaking.

I tell him about a smaller version of this I noticed in my own work. I edit podcasts. AI tools have become a multiplier on what I can process. When I run out of monthly credits, I spend $20 to get more.

“I just spent $20 on lunch,” I tell him. “My brain burning calories to think is more expensive than this.”

He’s with me on this. He keeps saying yeah.

The full sentence is: I probably have to eat multiple meals to get the calories needed to edit this many podcasts with my brain. Or I just spend $20 and get the same amount of podcasts processed. Talking’s way expensive. Don’t just talk. Do more creative stuff and planning.

What I’m describing in that moment is the same economic flip Tyler is describing about software, just dragged into the much narrower context of a single creator’s monthly content output. It’s the same shape. The build budget got cheap, and the talk budget, which used to be the cheap one, now looks comparatively absurd.

I want to push him on one thing, though.

The story Tyler is telling sounds, on its surface, like the same story technologists have been telling for years about every new tool that lowers the cost of building. Faster computers, better languages, more frameworks, lower-friction deploys. Every cycle gets a “this changes everything” claim. Why is this one different?

His answer is in the workflow on his monitor.

The earlier productivity gains, he implies, never broke the bottleneck that talking-about-building represented. You could build faster, sure, but the rate-limiter on a product team was never the coding speed of a senior engineer. It was the rate at which a team could agree on what to build, decide what to ship, review what got shipped. The talking layer was the bottleneck. Faster compilers didn’t fix that. Better languages didn’t fix that. More frameworks didn’t fix that.

What agents fix, in Tyler’s telling, is the entire chain from intent to implementation. You don’t need to align five humans to ship a feature anymore. You can describe it once, hand it to an agent, and check on its progress while another agent does something else. The unit of decision shrinks from a team to a person. The unit of time shrinks from sprint to afternoon.

“I’ve heard people talking about — hey, I had this idea, started on Friday night,” Tyler tells me. “By Sunday I was giving friends the URL so they could use it.”

This is the part you have to sit with. Not because the timeline alone is new. People have always built things on weekends. The difference is that the thing being built has, almost imperceptibly, gotten substantial enough that the weekend prototype is now what the team used to ship after a quarter of planning.

Friday-to-Sunday is not the new sprint. Friday-to-Sunday is the new quarter.

And if Friday-to-Sunday is the new quarter, then most of what used to happen in the quarter, the planning meeting, the spec review, the architecture debate, the “let me get back to you on that,” is the thing that’s actually too expensive.

There’s a corollary I keep returning to. It’s about ego.

Pre-AI, there was a real cost to opening your work to critique. You’d spent weeks or months — capital, time, attention, political will — getting the thing into a state where someone else could look at it. If they said it was bad, that wasn’t just an aesthetic loss. It was a credibility loss. You’d been wrong, expensively. You’d talked to a team about something that turned out not to be worth talking about. Egos protected themselves from this by getting cautious about what they showed.

Execution’s cheap now. So the cost of being wrong is small. Talk is cheap, so we should talk more. Execution’s cheap, so we should execute more. That’s the inversion of the Spotify line I keep coming back to. The expensive thing in the new economy isn’t the failed experiment. It’s the un-run experiment that the team is still discussing.

This is the change Tyler is actually pointing at when he calls his workflow what he calls it. He doesn’t say parallelization. He doesn’t say agent orchestration. He uses the language of running something, I want it running 24/7, because the basic ethical posture of his workflow is that compute is sitting there idle and that’s the waste. Not the wrong experiment. The unstarted one.

When you talk to product people right now, there are two camps. The first camp is treating AI like a productivity tool. They are getting faster at building specs, faster at writing emails, faster at producing artifacts that look like the artifacts they used to produce. The second camp, Tyler’s camp, is treating AI like an economy change. They are reorganizing their entire week around the idea that the constraint they grew up under has moved. The bottleneck isn’t engineering anymore. It’s the meeting that was built to optimize engineering.

The first camp will look back, three or four years from now, and find that they made themselves slightly more efficient inside a structure that was about to become obsolete. The second camp will already be operating on a different time horizon.

Tyler is in the second camp. He doesn’t make a big deal of it. He just describes his Tuesday afternoon. Six things running at once, two on agents, one on his chief of staff, one on his own attention. And the implication of the description is that the version of you about to ask “should we have a meeting about this?” is the version that lost time it didn’t have.

We end the call. He has, by his own count, several things running. The agents kept building while we talked.

That’s the part that stays with me.

Building stayed cheap. Talking is what cost us the hour.

Guest Bio: Tyler Wells

Tyler Wells is the Co-founder and CTO of BrainGrid AI, a planning-layer platform that acts as an AI product manager and tech lead before a coding agent writes a single line of code. Founded in 2025 alongside co-founder Nico Acosta, BrainGrid takes a plain-language idea and converts it into structured product specifications, task breakdowns, and implementation blueprints ready for tools like Cursor and Claude Code — targeting the domain experts, operators, and non-developers who have ideas they’ve never had the capital or technical background to build. The company emerged from the collapse of Wells’ prior startup, which he and Acosta wound down in late 2024 when they realized that the planning layer they were building for themselves was the product.

Previously, Wells spent seven and a half years at Twilio, ascending from individual contributor to Senior Director of Engineering before departing in 2021. At Twilio, he oversaw large engineering organizations and was responsible for cloud infrastructure operations — the environment where he first watched runaway AWS and Snowflake costs become six-figure surprises and developed the discipline around inference limits and cost management that now shapes BrainGrid’s architecture. Earlier in his career, he held engineering roles at Skype and Microsoft, accumulating more than 25 years of professional software engineering experience across the stack.

Wells is also the host of the Data Chaos Podcast and previously co-founded Propel Data, a prior analytics venture. He returned to individual-contributor engineering work when he co-founded BrainGrid — a deliberate choice to get back to building after years in senior management — and now operates a three-person team shipping product with parallel agent fleets across isolated Git worktrees.

Hey,

Thanks for reading this. I mean that. There's a lot of content out there competing for your attention, and you spent some of it here. I hope it was worth it. Even better, I hope it prompted you to think about something differently enough that you'd share it with someone who'd get something out of it too.

I started this podcast because tactics never stuck with me. What stuck were stories — business biographies, autobiographies, the decisions people made and why they made them. The principle only clicks once you know the story behind it.

So I built the thing I wanted to read. Every week I have two conversations with people who build in technology and product. Then I write the essay I wish I could find — one that puts you inside the conversation, through my eyes. What caught me off guard. What I kept thinking about after we hung up. Where the principle actually lives once you strip away the jargon.

I make this for myself first. If you read the way I do, you’ll want it too.

PS — If you want to pitch coming on the show, or you know someone I should talk to, shoot me an email at caden@hey.com with "January752" in the subject line so it gets past my filters. I'm not optimizing for famous guests. I'm optimizing for interesting conversations, even from people who aren't LinkedIn influencers.