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Founder Failures: Post-Mortems · Episode 13 · 11 min · 21 May 2026

Brutal Boardroom: Startup Post-Mortems That Pull No Punches

Two founders dissect their biggest business blunders—raw, unfiltered, and too insightful to keep secret.

What this episode covers

Two founders dissect their biggest business blunders—raw, unfiltered, and too insightful to keep secret.

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1,739 words · the script as narrated

Forty-two percent of startups fail because there is no market need for their product. Just… poof. Gone. All that work, all that money, for something nobody actually wanted. Exactly. And last week on the show we were digging into these huge, public business blunders, but this forty-two percent thing… that’s not a blunder. That’s a tragedy. And it’s one we know all too well. We do. We absolutely do. Are we really going to do this? I think we have to. We can’t sit here every week and dissect other people’s failures without looking at our own. So, let’s talk about Aura. Aura. Wow. Even saying the name feels… heavy. It was supposed to be the "one device to rule them all" for the smart home.

Remember the pitch? How could I forget? "An elegant, ambient interface that unifies your fragmented digital life." We were poets! We weren't just building a gadget; we were solving digital chaos. We thought the problem was chaos. We thought people hated switching between their Philips Hue app, and their Sonos app, and their Nest app. We were convinced that a single, beautiful piece of hardware was the answer. And the hardware was beautiful. Milled aluminum, a soft glowing light, that reactive e-ink display… We spent nine months just on the industrial design. Nine months. And that's the first lesson right there. Here's what that means if you're a founder: if you're spending more time on the physical casing than on validating the core problem with actual users, you are already in deep trouble.

Hold on—to be fair, we thought we were validating it. We saw the market size. Everyone was buying smart home stuff. It was a mess of apps and competing standards. The problem was obvious. It was obvious to us. We confused market size with customer urgency. That’s the Basis smartwatch mistake all over again. They raised thirty million dollars because they saw a huge market for health tracking, but they didn't realize that "health-conscious consumers" wasn't a group of people in acute pain. They were just… curious. And our users were the same. They were curious. They weren’t desperate. No one was losing sleep because they had to open two different apps to adjust their lights and music.

We got pre-orders, though. That's the insidious part. We got a couple thousand pre-orders and thought we had it. We were validated! Oh god, the pre-orders. That was the worst kind of validation because it was just other gadget nerds like us. It wasn't the mainstream user who was supposed to be our ultimate customer. It was a focus group of ourselves, basically. And we ignored the feedback from anyone who wasn't exactly like us. Remember that first beta tester, Sarah? The non-technical friend-of-a-friend we roped in? I do. She used it for a week and then sent that email. The email we laughed at. We did. We totally dismissed it. She wrote, "This is really pretty, but why wouldn't I just use my phone?

It feels like an extra step." And we said… what did we say? We said, "She doesn't get it. She's not the visionary user." We were so arrogant. We were building this incredibly complex back-end, a "Large Action Model for the home," we called it. We were so in love with our own technical solution, we couldn't hear the simplest, most profound question: "Why?" That’s exactly what the founders of Wasp said about their programming language. They built this whole new language because they thought it was the only way to solve the problem. But developers didn't want a new language. They just wanted the problem solved. We were doing the same thing. We were.

We were building a new religion when people just wanted a better prayer book. And Sarah’s feedback was the canary in the coal mine. We just… we chose to ignore the dead bird. So we push through, we finish the software, we go into production. We spend another six hundred thousand dollars on the first manufacturing run. Our money. Not VC money. Our own. Our own money. And launch day arrives. We've got the press releases cued up. We have our celebratory dinner reservation booked. We flip the switch. And then… silence. Not total silence. The tech blogs wrote about it. They said it was "an ambitious attempt" and "a beautifully designed piece of hardware." "Ambitious" is what they call you when they think you're going to fail.

It's the polite version of "insane." The Rabbit R1 got the same treatment. "AI innovation alone is not enough without strong execution and validation." That was the verdict. It was our verdict too. The sales dashboard was brutal. After the initial tiny bump from the last few pre-orders, it just flatlined. A few sales a day. Then one a day. Then one every few days. And the support tickets started coming in. Not angry tickets. Worse. Confused tickets. "How do I connect this to my garage door?" "Does this work with my smart-blinds from 2019?" We had built a universal remote that wasn't universal at all. Every one of those tickets felt like a personal failure.

Every single one was just a new way of saying "you didn't think about me." And the returns started. People who loved the idea of Aura got the reality of it and sent it back. Poor battery life. The connection to the cloud was laggy. It was just… clunky. It wasn't magic. It was supposed to be magic. That was the whole point. That’s the thing that really gets me. The moment I knew—I mean really knew—we were dead. It wasn't the sales numbers. It was about three months after launch. I was at a friend's house for a party. And he was one of our pre-order customers. A supporter. Oh, I don't think I've heard this story. I walked into his living room, and on the bookshelf, I saw it.

The Aura. Unplugged. With a little layer of dust on it. Oof. He hadn't even bothered to pack it up and return it. It wasn't worth the effort. It had just become… shelf-art. An expensive paperweight. And I just stood there looking at it, with my drink in my hand, and my stomach just dropped out. We hadn't even failed loudly enough for him to hate it. We had just… become irrelevant. That’s it. That’s the feeling. It’s not the anger or the backlash. It’s the indifference. The crushing, silent indifference of the market. And that's when the personal toll really started. Because for two years, Aura wasn't a project. It was us. My identity was completely fused with it.

When we got a good review, I was brilliant. When a line of code worked perfectly, I was a genius. And when it failed… It wasn't the business that failed. I failed. I was a failure. That's what it felt like. That Harvard Business School research about founders merging their identity with their company? I read that and I just nodded. It’s not an intellectual concept. It’s a gut-level reality. Every low felt like a reason to doubt ourselves. I stopped going to tech meetups. I didn't want to answer the question, "So, how's Aura doing?" I felt so much shame. Like I'd let everyone down. You, our families, the twenty-five hundred people who bought the damn thing.

The shame is the worst part. It’s not just the financial loss, which was… significant. It’s the feeling that you were uniquely stupid. That you were the only one who didn't see it coming. But the thing is, we weren't. Forty-two percent. That's a huge club to be in. We just built a very expensive, very beautiful solution to a problem that didn't exist with the urgency we imagined. So what do we do with that? What’s the lesson for the person listening to this right now, who is sketching out their own "Aura" on a napkin? Don't build the beautiful hardware first. For God's sake, don't. Build the ugliest, scrappiest, most embarrassing version of your solution you can.

A simple app. A web form. A concierge service you run through text messages. A "Wizard of Oz" prototype. Exactly. Be the man behind the curtain pulling the levers manually before you spend a dime on building the automated curtain-pulling machine. Find ten people who have the problem you think you're solving—not your friends, not other tech people. Find normal humans. And ask them to pay you for your ugly solution. And if they won't pay you for the ugly, cheap version… They will never, ever pay you for the beautiful, expensive one. That’s the brutal truth. You have to validate the pain before you design the painkiller. We designed a gorgeous, diamond-encrusted bottle for a vitamin C tablet.

People wanted an aspirin they could get at a gas station. And listen to the feedback. Especially the feedback that makes you defensive. The feedback you want to dismiss as "they don't get it." That's the feedback that matters. Sarah was our oracle, and we treated her like a crank. We have to be willing to let our beautiful ideas die. That’s the job. The job isn’t to be right about our initial vision. The job is to find a real problem and solve it for real people. Our love for the solution, for the elegance of the code, for the milled aluminum… that was the anchor that drowned us. It was a beautiful anchor, though. It really was. The best-designed anchor on the bottom of the ocean.

So, here's what that means if you're a founder: fall in love with your customer's problem, not your solution. Because the solution will have to change. It will have to evolve. It might even have to be thrown away entirely. But the customer's problem? If it's real, it'll still be there, waiting for you to finally solve it correctly. And that’s the part that gives me hope. Failure isn’t a dead end unless you stop learning. We learned. It cost us about a million dollars and two years of our lives, but we learned. So the question for everyone listening is not "is my idea good?" The question is, who is bleeding, and how can I offer them a bandage they are actually willing to pay for?

And are you willing to listen when they tell you your bandage is the wrong shape?

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.

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