I've managed over $10M in remote team payroll and seen every AI coworking mistake in the book. This is the culmination of a decade of experience, distilled into actionable advice you can implement today to see immediate improvements in your
What I've Learned From 96 Companies
A few patterns in AI coworking come up again and again.
The founders who handle AI coworking well understand that the data tells a different story than your gut.
The Counterintuitive Truth
In AI coworking, 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.
The AI Angle
Any discussion of AI coworking in 2026 has to include 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.
Some teams use AI to get far more out of AI coworking. Others spend heavily on AI that solves the wrong problem. The difference comes down to understanding what you're actually trying to achieve.
This connects to broader themes around AI culture building, digital nomad AI tools, async communication AI that I've been thinking about a lot lately.
Wrapping Up
I've shared a lot here, and I know it can feel overwhelming. But you don't need to get AI coworking right on day one. You just need to get started and keep improving.
Founders who do well at AI coworking tend to share one trait: they're relentlessly practical. They don't chase perfection. They chase progress.
That's the mindset I'd encourage you to adopt. Start where you are. Use what you have. Do what you can. And keep pushing forward.
As always, I'm rooting for you.
Frequently Asked Questions
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.
Q: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.
Q: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.