Promoting From Within to Preserve Culture

Most people think AI is overhyped. Nick Holzherr thinks it's drastically undervalued. After selling Whisk to Samsung and scaling it from zero to 120 people across eight time zones, he's now building Gitlaw—an AI agent that creates and reviews legal documents for free, making legal services accessible to small businesses that have been priced out of the market.

In this episode, Nick breaks down why fully remote distributed teams are the most effective way to scale fast, why async should be the default operating system for high-performing companies, and how he's doing the work of 50 people with a team of 15 by putting AI agents to work on everything from code to design to user feedback. He also shares why he promotes from within rather than parachuting in external managers, and how relationships built during one intense week together sustain distributed teams for the entire year.

What you'll learn:

🌍 Why hiring globally in a 3-4 hour time zone beats limiting yourself to local talent

🤖 How AI is undervalued—and why most businesses are only scratching the surface

⚡ Why async work should be your default operating system, not just a productivity hack

👥 How one intense week together physically sustains remote team relationships for a year

💼 Why legal services are fundamentally unfair—and how AI can level the playing field

🚀 How to do the work of 50 people with 15 by orchestrating AI agents effectively

Who should listen:

✔️ Founder-CEOs scaling distributed or remote teams and navigating hiring challenges

✔️ Tech leaders implementing AI and trying to understand its true potential beyond hype

✔️ Anyone building products where top 5% talent makes the difference between success and failure

✔️ Leaders interested in async-first cultures and alternatives to office-based work

Book recommendations:

Poor Charlie's Almanac - Charles T. Munger - https://www.amazon.co.uk/Poor-Charlies-Almanack-Expanded-3rd/dp/1578645018

Four Thousand Weeks - Oliver Burkeman - https://www.amazon.co.uk/Four-Thousand-Weeks-Management-Mortals/dp/1847924522

How to Win Friends and Influence People - Dale Carnegie - https://www.amazon.co.uk/How-Win-Friends-Influence-People/dp/0091906814

Podcast recommendation:

Lenny's Podcast - Lenny Rachitsky - https://www.lennyspodcast.com/

About the Guest:

Nick Holzherr is the founder of Gitlaw, an AI agent platform that helps small businesses create and review legal documents for free—democratizing access to legal services that have historically been too expensive or too slow for SMEs. Before Gitlaw, he founded Whisk, a recipe and food tech company he scaled from zero to 120 people distributed across eight time zones (minus eight to plus eight GMT) before selling it to Samsung in 2019, where he stayed for seven years.

He's a strong believer that AI's value is massively undervalued despite stock market hype, that async work should be the default for high-performing companies, and that legal documents will become 100 times cheaper and 10 times faster within one to two years. Nick has built his recent companies entirely as fully remote distributed teams, having learned that trying to hire top 5% specialized talent locally is nearly impossible unless you're paying Google or Facebook rates. Instead, he hires the best people globally within a 3-4 hour time zone, brings everyone together physically once a year for an intense week of relationship-building, and orchestrates AI agents to amplify what his lean team can accomplish.

GitLaw:

https://git.law/?utm_source=Interview&utm_medium=Podcasts&utm_campaign=Curious_Leadership

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Chapters:

00:00 Introduction

01:04 Nick’s background in startups, investment, and launching GitLaw

03:05 Why AI will make legal work cheaper and faster

07:09 The case for async work as an operating system

10:01 Async culture as the foundation for AI integration

12:46 Tools and rituals for managing high-output remote teams

19:46 Why most companies underestimate AI’s real capabilities

23:00 Using AI to 10x output without bloating team size

25:58 Making legal services more accessible through GitLaw

27:22 Leveraging different AI models for specific tasks

29:45 Risk of AI bias, hallucination, and misplaced trust

32:11 Timeless books that shaped Nick’s thinking and leadership

35:33 Promoting from within vs parachuting external leaders

37:26 How shared history and company culture drive better leadership