Here's something nobody tells you about i lost $100,000 on a bad deal. here's: the conventional wisdom is mostly backwards.
Before I ever saw a 100x return, I made a rookie mistake that cost me dearly. I'm sharing the full story of how I misread a syndicate investing and lost $100,000, so you don't have to learn this lesson the hard way. It was a painful but powerful education in what really matters in venture.
The Counterintuitive Truth
Here's what surprised me most about i lost $100,000 on a bad deal. here's: 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 the market doesn't care about your roadmap. It sounds simple. It's incredibly hard to execute.
The Reality Nobody Talks About
Most people approach i lost $100,000 on a bad deal. here's 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 you need to move fast and break things. 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 the data tells a different story than your gut. Once we made the switch, everything changed.
The Numbers Don't Lie
I've tracked the performance of companies in my portfolio that take i lost $100,000 on a bad deal. here's seriously versus those that don't. The difference is stark.
Companies that invest early in i lost $100,000 on a bad deal. here's see, on average, 2-3x better outcomes within 18 months. That's not a small edge. That's the difference between raising your next round and running out of runway.
One of my portfolio companies went from struggling to profitable in under a year after they finally got serious about this. The founder told me later that they wished they'd started sooner.
This connects to broader themes around syndicate investing, secondary markets, rolling funds, SPVs 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 $100,000 on a bad deal. here's: there are no shortcuts, but there are smarter paths.
The smartest founders I work with treat i lost $100,000 on a bad deal. here's 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 $100,000 on a bad deal. here's, 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'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 can I apply this thinking to my own situation?
Start by identifying the core principle behind the opinion, not the specific example. Then ask yourself: does this principle apply to my context? If yes, test it in a small, low-risk way before going all in.
What experience informs this perspective?
This perspective comes from over a decade of building companies in Silicon Valley, two successful exits (RemoteTeam to Gusto, MovieLaLa to Gfycat), and investing in 200+ startups including Anthropic, OpenAI, and Scale AI. I write about what I've lived.
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.