Two of my portfolio companies had opposite approaches to how my ai startup almost died before we. The one you'd expect to win didn't.
I've been in the Silicon Valley trenches for over a decade, and I've never seen a shift as massive as AI in healthcare. I'm sharing the hard-won lessons from my own startups and investments—the wins, the failures, and the counterintuitive strategies that actually work.
What I've Learned From 132 Companies
After investing in 200+ startups and running two companies to successful exits, I've developed a pretty clear picture of what works with how my ai startup almost died before we.
The biggest misconception is that you need to simplicity beats complexity every time. That's backwards. The companies that win are the ones that the best solutions are often the simplest ones.
I remember sitting with the Anthropic team early on and discussing how they thought about how my ai startup almost died before we. Their approach was counterintuitive but brilliant.
The Reality Nobody Talks About
Most people approach how my ai startup almost died before we with assumptions that made sense five years ago. The world has moved on. When I look at my portfolio companies, the ones that succeed are doing something fundamentally different.
The first thing to understand is that most founders overthink this and underspend on execution. I've seen this play out across dozens of companies. The pattern is unmistakable.
At RemoteTeam, we learned this the hard way. We spent months going down the wrong path before realizing that you need to move fast and break things. Once we made the switch, everything changed.
Lessons From the Trenches
I want to share a few specific lessons I've picked up over the years. These aren't theoretical. They come from real companies, real failures, and real successes.
Lesson 1: The best time to start thinking about how my ai startup almost died before we was yesterday. The second best time is now. Don't wait until you have the perfect plan.
Lesson 2: Hire for attitude, train for skill. The best how my ai startup almost died before we practitioners I've met weren't the most technically gifted. They were the most curious and persistent.
Lesson 3: Your competitors are probably getting this wrong too. That's your opportunity. While everyone else is following the same playbook, you can zig when they zag.
This connects to broader themes around AI diagnostics, biotech AI, clinical AI, drug discovery AI, AI mental health that I've been thinking about a lot lately.
Wrapping Up
I've shared a lot here, and I know it can feel overwhelming. But here's the thing about how my ai startup almost died before we: you don't need to get everything right on day one. You just need to get started and keep improving.
The founders in my portfolio who excel at how my ai startup almost died before we share one trait: they're relentlessly practical. They don't chase perfection. They chase progress.
That's the mindset I'd encourage you to adopt. Start where you are. Use what you have. Do what you can. And keep pushing forward.
As always, I'm rooting for you.
Frequently Asked Questions
Do all experts agree with this view?
No, and that's fine. The best ideas in business are often contrarian. I share my perspective based on my experience and data, but I encourage you to seek out opposing viewpoints and form your own conclusions.
What's the most common pushback you get on this?
People often push back by citing exceptions or edge cases. And they're usually right that exceptions exist. But building a strategy around exceptions rather than patterns is a losing game for most founders.
How has this view evolved over time?
My thinking on most topics has changed significantly over the years. Early in my career, I held many conventional views that experience proved wrong. I try to update my beliefs when the evidence changes.