Nick Holzherr has really done it all.
He’s sold companies, bought companies, invested in over 20 startups…
AND he’s taken Whisk from zero to 120 people – all before selling it to Samsung in 2019.
He also runs fully distributed teams. Always has.
Most people think that’s mental, but for Nick it’s the only way to scale fast (if you’re not Google or Facebook, and let’s face it, you aren’t).
This conversation is about why fully remote beats office-based (with data arguments on both sides), why async work is the actual operating system for high-performing teams, and why the majority of people are drastically undervaluing AI.
Nick’s currently building GitLaw – an AI agent that drafts and reviews legal documents.
He’s seeing what 15 people can do when they’re doing the work of 50 – all without the communication overhead that slows down a team of that size.
This is some of what we go over:
- Why hiring globally for top 5% talent beats hiring locally for “pretty good” talent
- The three-to-four-hour time zone rule (Korea to San Francisco was too extreme)
- How async work creates perfect context for AI
- Why his original leadership team is still with him 15 years later
- Why legal services being accessible only to rich companies is fundamentally unfair
There’s also a brilliant moment about measuring productivity in distributed teams (you can’t rely on “they bring donuts and make coffee” anymore), and why the bottleneck for AI isn’t technology – it’s having really smart people who can judge when the AI is right and when it’s wildly wrong.