Most of what you've read about i lost $1,000,000 on a follow-on investment and is wrong. I know because I believed it too, and it cost me.
Before hitting a big win, I made a costly mistake in follow-on investing that lost me $1,000,000. I’m sharing the full story so you can avoid making the same error. This was a tough lesson that changed how I approach venture investing.
The Reality Nobody Talks About
Most people approach i lost $1,000,000 on a follow-on investment and 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 the data tells a different story than your gut. 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 most founders overthink this and underspend on execution. Once we made the switch, everything changed.
The Counterintuitive Truth
Here's what surprised me most about i lost $1,000,000 on a follow-on investment and: the best practitioners do less, not more.
When I was building MovieLaLa, we tried to do everything at once. We had the best technology, the smartest team, and we still almost failed because we spread ourselves too thin.
The lesson I took from that experience, and from watching hundreds of other companies, is that you should focus on one thing and do it exceptionally well. It sounds simple. It's incredibly hard to execute.
What I've Learned From 123 Companies
After investing in 200+ startups and running two companies to successful exits, I've developed a pretty clear picture of what works with i lost $1,000,000 on a follow-on investment and.
The biggest misconception is that you need to the data tells a different story than your gut. That's backwards. The companies that win are the ones that you need to move fast and break things.
I remember sitting with the Anthropic team early on and discussing how they thought about i lost $1,000,000 on a follow-on investment and. Their approach was counterintuitive but brilliant.
The AI Angle
I can't talk about i lost $1,000,000 on a follow-on investment and in 2026 without mentioning AI. As someone who's invested in Anthropic, OpenAI, Scale AI, and Hugging Face, I have a front-row seat to how AI is transforming this space.
The short version: AI makes good practitioners better and bad practitioners worse. It's an amplifier, not a replacement.
I've seen companies use AI to 10x their i lost $1,000,000 on a follow-on investment and capabilities. I've also seen companies waste millions on AI solutions that solved the wrong problem. The difference comes down to understanding what you're actually trying to achieve.
This connects to broader themes around rolling funds, secondary markets, follow-on investing, term sheets, portfolio construction that I've been thinking about a lot lately.
Final Thoughts
After two exits, 200+ investments, and more mistakes than I can count, here's what I know for sure about i lost $1,000,000 on a follow-on investment and: there are no shortcuts, but there are smarter paths.
The smartest founders I work with treat i lost $1,000,000 on a follow-on investment and as a competitive advantage, not a checkbox. They invest in it early, measure it obsessively, and never stop improving.
If you're just getting started with i lost $1,000,000 on a follow-on investment and, don't be intimidated. Everyone starts somewhere. The key is to start with the right mindset and the right framework, and then execute like your company depends on it. Because it probably does.
Frequently Asked Questions
What would you do differently looking back?
I'd move faster on the things that were working and cut the things that weren't sooner. Most founders, myself included, hold onto failing strategies too long because of sunk cost. Speed of learning is everything.
Can these results be replicated?
The specific numbers will vary, but the underlying patterns and principles are transferable. The key is understanding the context behind the results, not just copying the tactics. Every company has unique constraints that shape what works.
How long did it take to see results?
Most meaningful business results take 3-6 months to materialize. Anyone promising overnight success is selling something. The companies in my portfolio that grew fastest were the ones that stayed patient and consistent.