Planningupfront

This is part of the series Startup that Failed . The Moment I Knew Month 6. I was debugging a HIPAA compliance issue at 2 AM that would affect maybe three users. And I remember thinking: This isn’t going to work. Not the bug. The whole thing. The startup. The vision. The 18-month plan I’d laid out so carefully. I knew. Deep in that part of your brain that’s honest when the rest of you isn’t. I knew the math didn’t work. I knew the market didn’t care. I knew I was building something impressive that nobody wanted. ...

This is part of the series Startup that Failed . The Irony of the Minimum Viable Product Here’s a fun exercise: Take the definition of MVP ~ Minimum Viable Product ~ and tell me which word matters most. If you said Product, congratulations, you’re me 18 months ago. If you said Viable, you’re getting warmer but still wrong. The answer, painfully obvious in retrospect, is Minimum. But minimum is boring. Minimum doesn’t impress investors. Minimum doesn’t showcase your technical prowess. Minimum feels like giving up before you even start. ...

This is apart of the series Startup that Failed . The Problem with Problems Here’s the thing about building startups — everyone talks about solving problems. But there’s a massive difference between a problem existing and a problem worth solving. And an even bigger gap between a problem worth solving and a problem someone will actually pay to solve. I learned this the hard way. Or did I learn it at all? That’s the existential dread that keeps me up at night. ...

This is a no-fuss summarization of what I’ve learned from running my own startup and failing hard at it. The good, the bad, and the brutally honest. It’s a series of short essays where I dissect every mistake, every win, and every “what the hell was I thinking?” moment. If you’re thinking about a side project, already knee-deep in one, or just enjoy watching someone learn expensive lessons so you don’t have to - then this series of essays is for you. ...