I've been investing in AI companies since before it was cool. i almost destroyed my company with bad ai is the thing that separates winners from losers.
I confess: my initial approach to AI was a disaster. I'm sharing the painful story of my biggest leadership failure and the redemption that followed, hoping you can avoid my near-fatal mistakes.
What I've Learned From 118 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 almost destroyed my company with bad ai.
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 customer feedback is the only metric that matters.
I remember sitting with the Anthropic team early on and discussing how they thought about i almost destroyed my company with bad ai. Their approach was counterintuitive but brilliant.
The Reality Nobody Talks About
Most people approach i almost destroyed my company with bad ai 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 customer feedback is the only metric that matters. 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.
The Framework That Actually Works
I'm going to share the exact framework I use when evaluating i almost destroyed my company with bad ai. It's not complicated, but it requires discipline.
Step 1: your team matters more than your technology This is where most people go wrong. They skip this step entirely and jump straight to execution. Don't do that.
Step 2: the market doesn't care about your roadmap 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 almost destroyed my company with bad ai are the ones that treat it as an ongoing process, not a one-time project.
The Numbers Don't Lie
I've tracked the performance of companies in my portfolio that take i almost destroyed my company with bad ai seriously versus those that don't. The difference is stark.
Companies that invest early in i almost destroyed my company with bad ai 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 AI change management, AI transformation leadership, managing AI teams that I've been thinking about a lot lately.
The Bottom Line
Look, i almost destroyed my company with bad ai isn't rocket science. But it does require intentionality, consistency, and a willingness to learn from mistakes.
If you take one thing from this article, let it be this: start now, start small, and iterate. The founders who win at i almost destroyed my company with bad ai aren't the ones with the best strategy on paper. They're the ones who execute, learn, and adapt faster than everyone else.
I've been doing this for over a decade. The patterns are clear. The companies that take i almost destroyed my company with bad ai seriously outperform the ones that don't. Every single time.
If you're working on something interesting in this space, I'd love to hear about it. Drop me a line.
Frequently Asked Questions
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.
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 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.