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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.

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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.

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