Founder Failures: Post-Mortems · Episode 10 · 9 min · 30 April 2026
Brutal Business Blunders: Behind Closed Doors with Founders
Candid, no-holds-barred post mortems on startup missteps—lessons from failures you were never meant to hear.
What this episode covers
Candid, no-holds-barred post mortems on startup missteps—lessons from failures you were never meant to hear.
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Transcript
1,453 words · the script as narrated
The Humane AI Pin. Two hundred and forty million dollars in funding, two hundred engineers, five years of development... and by February 2025, every single one of those seven-hundred-dollar devices will be a brick. They're shutting it all down. Hits a little too close to home this week, doesn't it? That feeling of a rocket that just… fails to ignite. A little? It's the only thing I've been thinking about. Which is why we have to talk about it. We have to talk about Project Atlas. Okay. Let's do it. A post-mortem, for the public record. Where do you even want to start with that beautiful, glorious, quarter-million-dollar mistake? Let’s start at the beginning.
The assumption. Because we were so damn sure. We saw a handful of our top one-percent power users doing this incredibly complex workaround in our system. And we thought— Hold on—we didn't just think. We got arrogant. We thought, "We've discovered a secret desire! A hidden need!" We were geniuses. Exactly! We were convinced we'd found the next big thing. We were going to build this elegant, integrated solution right into the core product. No more workarounds. We were going to save them. Except we never stopped to ask if they actually wanted to be saved. Or, more importantly, if anyone else on the planet cared. It’s that classic line I read about the Humane Pin: "A founder belief is not a customer problem." And boy, did we have a belief.
We had a religion. And Project Atlas was our cathedral. It reminds me of the Juicero story. They raised one hundred and twenty million dollars to build this Wi-Fi connected, four-hundred-dollar machine to squeeze a proprietary bag of juice pulp. Only for a journalist at Bloomberg to find out you could just… squeeze the bag with your bare hands and get the exact same amount of juice. The exact same! They built a technological marvel to solve a problem that literally did not exist. And that's what we did. We saw five people building their own canoes to cross a river, and we decided to build a nuclear-powered submarine for them, instead of just asking if a simple bridge would do.
And here's what that means if you're a founder or a product lead listening to this. Those power users? They can be a trap. They love complexity. They love being the smartest person in the room who figured out the workaround. Building for them can feel like progress, but you might just be building a beautiful, expensive thing for an audience of five. We mistook a niche behavior for a universal need. And once we made that mistake, the momentum took over. The sunk cost fallacy is a monster. Once the first check is written, once the engineers are assigned… that train does not want to stop. I was reading the post-mortem from the CEO of Monarch Tractor.
They built these incredible autonomous, electric tractors. Raised over two hundred and forty million. The tech worked. But the business model didn't. He said, and this quote is haunting me, "We should have pivoted harder and faster. If we had done that two years ago, it would have been a different story." Oh, that hurts to hear. Because we had that moment. Remember that meeting in March? Sarah from marketing… bless her heart… she came in with the survey data. We’d surveyed five hundred customers. And the feature that became Project Atlas? It ranked dead last. Number fifteen out of fifteen requested features. I remember it perfectly. We looked at the data, we nodded, and we said, "They just don't get the vision yet.
They'll understand when they see it." We were so deep in our own Kool-Aid. We dismissed the data. We dismissed the one person in the room telling us the emperor had no clothes. Because walking it back then? It would have meant admitting to the board, to the team, that our big, brilliant idea was a dud. It was easier to just keep building. That's the key for anyone managing a team. The pressure to stick with the plan is immense. You've sold the vision in the all-hands. You've promised it to investors. Pivoting feels like failure. But as the Monarch CEO said, not pivoting is failure. It's just a slower, more expensive, and more painful one.
We chose the expensive one. So we finished it. Six months of work. Late nights. Our best engineers. We polished every pixel. We launched it. We sent the email, wrote the blog post, popped a bottle of cheap champagne in the office. And then… silence. No, it was worse than silence. It was data. The dashboard was our report card, and it was a straight F. Zero. Point. Zero. Percent. Adoption. Outside of the original five guys who were doing the workaround anyway. The failure was, to borrow a phrase from the Humane analysis, "immediate and total." There was no "wait and see." There was no "maybe it needs more marketing." The market just gave us a collective, silent, and brutal "no." I have to admit something.
For the first forty-eight hours, I was checking the analytics dashboard every five minutes. I was literally hitting refresh, like a gambling addict at a slot machine, just hoping… willing the numbers to move. It was pathetic. We all were. That's the fantasy, right? That you're just one blog post, one tweet, one influencer away from it all turning around. But it never does. And here's the lesson. If you're a founder, if you're a PM, that dashboard is not a wishing well. It will not magically change because you want it to. It's telling you the truth. And the truth for us was that we had spent a quarter of a million dollars building a feature nobody wanted.
So we had to kill it. And that conversation… that was the worst part of this whole thing. Worse than losing the money. A hundred times worse. Standing in front of the engineering team. The same people who had cancelled weekend plans, who had poured their creativity and intelligence into this thing for half a year… and telling them we were turning it off. That their work was being shelved. One of the junior engineers, Alex, asked, "So… all that work was for nothing?" And I didn't have a good answer. I said something about "learnings" and "iteration," and it just sounded so hollow. Like corporate jargon to paper over a massive screwup.
Because it was. We can dress it up now, but in that moment, we failed them. We wasted their time. Their talent. That's the real cost. The money is just numbers in a spreadsheet. The loss of trust and morale with your team… that’s so much harder to earn back. And the money isn't just numbers, not really. That quarter-million-dollar hole in our runway? That's three hires we can't make this year. That's the marketing campaign we can't run. That mistake has a real, tangible impact on our future. It's not some abstract "learning." It's a constraint. So what’s the actual takeaway? For us, for anyone listening who just felt a knot in their stomach because they have a Project Atlas of their own in the works right now?
For me, it’s that you have to separate the user from the behavior. We saw a behavior—the workaround—and we fell in love with it. We never stopped to understand the user. Why were they doing it? What was their real goal? We built a solution for the what, not the why. I think that’s right. Mine is a little more brutal. You have to be willing to kill your darlings. Everyone says that. But they mean you have to kill them when they're on the whiteboard. You have to find the fatal flaw when it's just a sketch, an idea, a line in a document. Before it has a project name and a budget. Exactly. Because once it has a budget and a team, it’s not a darling anymore.
It’s a zombie. And it will eat your company's brains if you let it. We let it wander around for six months before we finally put it down. A zombie. That's perfect. Project Atlas was our zombie. Okay, I'm taking away two things. One: "A founder belief is not a customer problem." I'm getting that tattooed on my forehead. And the second? Don't build nuclear submarines for people who just need a bridge. Ask them. For God's sake, just ask them what they want. It all sounds so simple when we say it now, after the fire. The real question is, will we be brave enough to actually listen next time?
About Founder Failures: Post-Mortems
Two founders dissect a business decision that went badly wrong, with the kind of brutal honesty you normally only hear behind closed doors.
