I've managed over $4M 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 44 Companies
A few patterns in AI coworking come up again and again.
The founders who handle AI coworking well understand that you need to move fast and break things.
The Reality Nobody Talks About
A lot of the advice on AI coworking rests on assumptions that made sense five years ago. The world has moved on.
The first thing to understand is that you need to move fast and break things. 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 the market doesn't care about your roadmap. Once they make the switch, everything changes.
The Counterintuitive Truth
In AI coworking, the best practitioners often do less, not more.
The lesson: the market doesn't care about your roadmap. 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 performance reviews, async communication AI, digital nomad AI tools, AI coworking, AI culture building that I've been thinking about a lot lately.
What's Next
Best practice in AI coworking 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 coworking 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 are the most common mistakes with AI coworking?
The biggest mistake I see is overcomplicating things early on. Start with the simplest version that works, get real feedback, and iterate from there. Another common trap is copying what worked for someone else without understanding the context behind their decisions.
Q:What tools do I need to get started?
Start with the basics. You don't need expensive software or fancy tools. A spreadsheet, a note-taking app, and direct access to your customers will get you further than any enterprise platform. Add tools only when you hit a specific bottleneck.
Q:How long does it take to get AI coworking right?
The timeline varies depending on your starting point and resources. For most founders, expect 2-4 weeks for initial setup and 2-3 months to see meaningful results. I've seen teams move faster when they focus on one thing at a time rather than trying to do everything at once.
Q:Do I need technical skills for AI coworking?
Not necessarily. While technical understanding helps, the most important skills are clear thinking and the ability to break problems into smaller pieces. Many successful founders I've invested in started with zero technical background and either learned enough to be dangerous or found the right technical partner.