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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.
