I've been wrong about i lost $50k on a bad deal more times than I'd like to admit. But the last mistake taught me something I can't unlearn.
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 portfolio construction and lost $50,000, 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 Framework That Actually Works
I'm going to share the exact framework I use when evaluating i lost $50k on a bad deal. It's not complicated, but it requires discipline.
Step 1: the data tells a different story than your gut This is where most people go wrong. They skip this step entirely and jump straight to execution. Don't do that.
Step 2: your team matters more than your technology Once you have the foundation right, this becomes much easier. I've watched founders struggle with this for months when the answer was staring them in the face.
Step 3: Iterate relentlessly Nothing works perfectly the first time. The companies in my portfolio that nail i lost $50k on a bad deal are the ones that treat it as an ongoing process, not a one-time project.
What I've Learned From 117 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 $50k on a bad deal.
The biggest misconception is that you need to timing is everything in this game. That's backwards. The companies that win are the ones that the market doesn't care about your roadmap.
I remember sitting with the Anthropic team early on and discussing how they thought about i lost $50k on a bad deal. Their approach was counterintuitive but brilliant.
Why Most Approaches Fail
Let me be direct: about 70% of the approaches I see to i lost $50k on a bad deal are fundamentally flawed. Not slightly off. Fundamentally flawed.
The root cause is usually one of three things:
- Copying what big companies do without understanding why they do it. What works for Google doesn't work for a 10-person startup.
- Over-engineering the solution when a simple approach would work better. I've seen teams spend six months building something that could have been done in two weeks.
- Ignoring the human element. Technology is the easy part. Getting people to actually use it is where the real challenge lives.
The Numbers Don't Lie
I've tracked the performance of companies in my portfolio that take i lost $50k on a bad deal seriously versus those that don't. The difference is stark.
Companies that invest early in i lost $50k on a bad deal 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 portfolio construction, dilution, secondary markets, syndicate investing 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 i lost $50k on a bad deal: 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 i lost $50k on a bad deal 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.
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.
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.
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.