After 200+ angel investments, I've seen the same i almost destroyed my company with bad ai mistake destroy companies over and over.
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.
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 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 customer feedback is the only metric that matters. 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: 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: you should focus on one thing and do it exceptionally well 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.
What I Tell Founders
When a founder in my portfolio asks me about i almost destroyed my company with bad ai, I usually start with three questions:
- What's your timeline? Because the right approach for a company with 6 months of runway is very different from one with 3 years.
- What have you already tried? Most founders have tried something. Understanding what didn't work is often more valuable than knowing what might.
- Who on your team owns this? If the answer is "everyone" or "no one," that's your first problem to solve.
These questions seem simple but they reveal a lot about where a company actually stands.
This connects to broader themes around AI change management, managing AI teams, leading through uncertainty that I've been thinking about a lot lately.
What's Next
The world of i almost destroyed my company with bad ai is moving fast. What worked last year might not work next year. That's both the challenge and the opportunity.
My advice: stay curious, stay humble, and stay close to the people who are actually doing the work. Read less thought leadership and do more experiments. Talk to fewer consultants and more practitioners.
And if you're a founder building in this space, remember that the best time to get i almost destroyed my company with bad ai right is before you need to. Don't wait for a crisis to force your hand.
I'll keep sharing what I learn. This stuff matters too much to keep to myself.
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.
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'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.