I’m a 2x education entrepreneur who has worked with thousands of founders on-the-ground in 22 countries. My writing shares lessons learned about startups, video, and AI.
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How to Run a Personal Board of Directors Meeting (a crazy idea that, ten years later, has simultaneously deepened my friendships made me more successful)
Tracking Down Jack White: Lessons behind a manhunt for a grammy-winning rockstar (how to do outreach to important people)
Kobe Bryant’s Secret Handbook: Look Where No One Else is Looking (how to get secret advantages)
Beating Perfectionism Means Striving For Collisions, Not Beauty
Seeing is Believing? Not According to Cognitive Scientist Donald Hoffman
Be Careful What You Carry (a story about life in Austin in the early 2000s)
Blog
- The Last Moat
- Mexico Stories and Observations
- A Simple Rule for Managing Complexity: The Double Cushion
- It’s Perfectly Fine that Origin Stories are Lies
- Go Bigger When You Talk About Your Ideas
- The Best Conference of the Year (So Far)
- Centuries Old Wisdom in MrBeast’s Leaked Playbook
- When Your Uber Driver Asks You to Lie to the Police
- You’re Not Using AI Enough
- Winning an Award and the Power of Relationships
- Don’t Leave Money on the Table: The Secret of Free Upside
- High-throughput AI: “Speech In, Text Out” (SITO)
- The Secret Killer of Startup Ideas: Mexico Month Part 5
- Notes From a Fever Dream: Mexico Month Part 4
- Agave and Anarchy: My Day in Tequila: Mexico Month Part 3
- Business Lessons from a Guy with a Face Tattoo: Mexico Month Part 2
- Invisible Architecture of Opportunity: Mexico Month Part 1
- Schwarzenegger and the 50/50 Rule
- The 10% Rule of Camera Presence
- Expert Showdowns: A Riff on Live Learning
- Stumbling to Greatness
- Unfakeable Expertise
- The Art Of Approaching Strangers: Lessons From Humans Of New York
- The Time I Told My Biggest Customer to Go F*ck Themselves
- Oversmiling: A Simple Trick To Come Across Warmer On Camera
- How (and why) to run a personal shareholder meeting
- Beware Filter Bubbles
- Tune Your Linkedin Profile To Create Opportunities
- The Ask And Offer
- “If You Are Here, Who Is Driving The Ship?”
- What To Do When Someone Calls You a Copycat
- You Already Have The Answer
- Western Art in Denver
- How To Shoot Your Shot With an Important Person
- The first thing your customers see
- How I Go From Idea to Filming
- I Got Taken for a Ride in India
- The Upside of Getting Screwed Over
- Where Nobody Wants You to Become a Millionaire
- Ask For More
- Big Ideas Aren’t Enough
- The Time We Turned Down NBC’s The Office
- The Magic of the First Few Cohorts
- How to make your work feel more valuable
- What Would Life Be Like if Rejection Didn’t Hurt?
- A Review of Buildspace’s Nights and Weekends Program
- Beating Perfectionism Means Striving For Collisions, Not Beauty
- Be Careful What You Carry
- The Beautiful Game
- Seeing is Believing? Not According to Donald Hoffman.
Newsletter
All of my best writing is in my weekly newsletter: