I've managed over $8M in remote team payroll and seen every AI culture building mistake. This is a decade of my experience, distilled into actionable advice you can use today.
The Reality Nobody Talks About
A lot of the advice on AI culture building rests on assumptions that made sense five years ago. The world has moved on.
The first thing to understand is that the data tells a different story than your gut. I've seen this play out across dozens of companies. The pattern is unmistakable.
Many teams spend months on the wrong path before realizing that timing is everything in this game. Once they make the switch, everything changes.
The Counterintuitive Truth
In AI culture building, the best practitioners often do less, not more.
The lesson: the best solutions are often the simplest ones. It sounds simple. It's incredibly hard to execute.
The Numbers Don't Lie
Investing early in AI culture building can be 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 digital nomad AI tools, AI culture building, hybrid work AI, async communication AI, AI performance reviews that I've been thinking about a lot lately.
What's Next
Best practice in AI culture building is changing 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.
If you're building in this space, the best time to get AI culture building 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
Q: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 234 startups including Anthropic, OpenAI, and Scale AI. I write about what I've lived.
Q: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.
Q: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.