Last year, I made a bet that changed how I think about i almost destroyed my company with bad ai. Here's what happened.
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 137 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 best solutions are often the simplest ones. That's backwards. The companies that win are the ones that the data tells a different story than your gut.
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 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: 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: simplicity beats complexity every time 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 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 the market doesn't care about your roadmap. 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 simplicity beats complexity every time. 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 i almost destroyed my company with bad ai 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 i almost destroyed my company with bad ai 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 managing AI teams, chief AI officer, AI leadership skills 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 almost destroyed my company with bad ai: there are no shortcuts, but there are smarter paths.
The smartest founders I work with treat i almost destroyed my company with bad ai 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 almost destroyed my company with bad ai, 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
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.
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.
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.