I've managed over $2M in remote team payroll and seen every async communication AI mistake in the book. This is the culmination of a decade of experience, distilled into actionable advice you can implement today to see immediate improvement
What I've Learned From 51 Companies
Across 234 angel investments, including Anthropic, a few patterns in async communication come up again and again.
The founders who handle async communication well understand that the data tells a different story than your gut.
The Reality Nobody Talks About
A lot of the advice on async communication rests on assumptions that made sense five years ago. The world has moved on.
The first thing to understand is that you should focus on one thing and do it exceptionally well. 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 most founders overthink this and underspend on execution. Once they make the switch, everything changes.
The Counterintuitive Truth
In async communication, the best practitioners often do less, not more.
The lesson: the data tells a different story than your gut. It sounds simple. It's incredibly hard to execute.
Lessons From the Trenches
I want to share a few specific lessons I've picked up over the years. These aren't theoretical. They come from real companies, real failures, and real successes.
Lesson 1: The best time to start thinking about async communication was yesterday. The second best time is now. Don't wait until you have the perfect plan.
Lesson 2: Hire for attitude, train for skill. The best people at async communication are rarely the most technically gifted. They are the most curious and persistent.
Lesson 3: Your competitors are probably getting this wrong too. That's your opportunity. While everyone else is following the same playbook, you can zig when they zag.
This connects to broader themes around async communication AI, AI coworking, digital nomad AI tools, hybrid work AI, AI culture building that I've been thinking about a lot lately.
The Bottom Line
None of this is rocket science. But it does require intentionality, consistency, and a willingness to learn from mistakes.
If you take one thing from this article, let it be this: start now, start small, and iterate. The founders who win at async communication aren't the ones with the best strategy on paper. They're the ones who execute, learn, and adapt faster than everyone else.
Companies that take async communication seriously tend to pull ahead of the ones that don't.
If you're working on something interesting in this space, I'd love to hear about it. Drop me a line.
Frequently Asked Questions
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.
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: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.