One Lunch Away From the Only Job He's Ever Had

Aug 5, 2026

Aaron Vaccaro was a senior in college, striking out on every internship, staring into the abyss. One spring afternoon, after an investment club presentation, he spotted a board member in the lunchroom and did something most people wouldn't — he asked if they could grab lunch.

That board member knew a guy in Seattle. Didn't really know what he did. Just had a feeling they'd connect.

That feeling turned into a phone call. That phone call turned into a summer internship. That internship turned into 12 years working alongside Eric Anderson — investor, visionary, and the man Aaron credits for everything he knows about business and life.

In this episode, Aaron unpacks what it actually looks like to find the right mentor, earn their trust, and grow alongside them for over a decade — from scaling TopGolf to building Singularity University.

We get into:

• The one lunchroom moment that changed everything
• What to look for in a mentor — and what they're looking for in you
• Why capability plus values alignment is the formula for any great partnership
• The art of unbundling complex problems — and why most people conflate everything
• Visionary leaders vs. execution leaders — and figuring out which one you are
• What succession planning looks like when your mentor is your north star
• Why deep tech, energy, biology, and robotics are where Aaron is placing his bets next
• The unexpected lesson of becoming a first-time dad

If you've ever wondered what it takes to find the right person to learn from — and how to make the most of it — this one's for you.