After years of trial and error, I finally cracked the code on AI culture building. I'm sharing the raw, unfiltered story of my struggles and the hard-won victories so you can skip the mistakes and get straight to the results. It wasn't easy
Why Most Approaches Fail
Many common approaches to AI culture building are flawed at the root.
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.
What I've Learned From 144 Companies
Across 234 angel investments, including Anthropic, a few patterns in AI culture building come up again and again.
The founders who handle AI culture building well understand that you need to move fast and break things.
The Counterintuitive Truth
In AI culture building, the best practitioners often do less, not more.
The lesson: timing is everything in this game. It sounds simple. It's incredibly hard to execute.
Real Talk: What Actually Matters
Here is what actually matters in AI culture building.
First, execution speed beats perfection. Every time. Companies rarely fail because they moved too fast on AI culture building. Many fail because they moved too slowly.
Second, measure everything. If you can't measure it, you can't improve it. Set up tracking from day one, even if it's basic.
Third, talk to your users. It sounds obvious, but many founders make decisions about AI culture building in a vacuum. Get out of the building. Talk to real people.
This connects to broader themes around AI performance reviews, digital nomad AI tools, async communication AI that I've been thinking about a lot lately.
Final Thoughts
There are no shortcuts in AI culture building, but there are smarter paths.
The strongest teams treat AI culture building 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 AI culture building, 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
Q:Are these recommendations still relevant in 2026?
Absolutely. While specific tools and tactics change, the underlying principles remain consistent. I update my thinking regularly based on what I'm seeing in the market and across my portfolio companies.
Q:Can I implement all of these at once?
I'd strongly recommend against it. Pick the 2-3 items that resonate most with your current situation and focus there. Trying to do everything simultaneously is a recipe for doing nothing well.
Q:How were these items selected?
Each item on this list comes from direct experience, either from building my own companies or from patterns I've observed across the 234 startups I've invested in. I prioritize practical, actionable items over theoretical concepts.
Q:Which item on this list has the highest impact?
It depends on your stage and context, but in my experience, the items near the top of the list tend to have the broadest applicability. That said, sometimes the less obvious items create the biggest breakthroughs for specific situations.