Here's something nobody tells you about i almost destroyed my company with bad ai: the conventional wisdom is mostly backwards.
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.
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 timing is everything in this game. 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 best solutions are often the simplest ones. Once we made the switch, everything changed.
Why Most Approaches Fail
Let me be direct: about 70% of the approaches I see to i almost destroyed my company with bad ai 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 AI Angle
I can't talk about i almost destroyed my company with bad ai 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 almost destroyed my company with bad ai 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 leading through uncertainty, AI transformation leadership, chief AI officer, managing AI teams 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
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.
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.