FREE AGENTS
An ambitious, unconventional community. Most of us have taken a career break, are on one, or are seriously considering one.
WHAT IT IS
Free Agents is a small private community. We meet monthly, talk async in a group chat, and help each other through the slow work of figuring out what's next.
Instead of startup networking or unemployed buddies complaining together, we focus on real conversations, to do the inner work and the building work in parallel.
WHO'S HERE
Members come from ambitious backgrounds like tech, finance, startups, and consulting.
Some examples:
• An ex-investment banker who went to the White House, then into local government leadership
• An ex-software engineer building a live immersive experience company
• A big tech product designer who's now a surf content creator and actress
• A former PM who cooked at a two-Michelin-star restaurant, and is now a jiu jitsu coach and part-time barista
• An ex-hedge fund investor starting his own men's fashion brand
What unites us isn't a job title. It's an orientation.
A LITTLE PHILOSOPHY
There are missionaries. They give themselves to a mission, sometimes at the cost of everything else.
There are mercenaries. They optimize for the biggest paycheck.
Most of Silicon Valley (or corporate America) tells you to pick one.
A Free Agent picks neither. They channel missionary passion without sacrificing themselves. They practice mercenary discipline around earnings without making money the only metric. They envision, experiment, and design careers that fit their actual life. Just like professional athletes, free agents are devoted to the practice, not the team.
FOUR PRINCIPLES
Dare to question the norm.
We're in pursuit of greater things and a more meaningful life.
Integration over optimization.
A whole life, not a maximized one.
Curiosity over legibility.
It's okay if your path doesn't fit on a LinkedIn page.
Ambition on our own terms.
We love being ambitious. We don't shy away from wanting success. We just define what success means for ourselves.
A SHORT STORY
In 2022, I was a Senior PM at Afterpay. Just promoted and living in Hawaii. I surfed in the mornings, journaled, practiced yoga, and ate well. From the outside, dialed.
But something quietly felt off.
It took me almost a year to admit the ladder I was climbing didn't go anywhere I wanted to go. I left without a next move lined up.
Leaving the default path is exhilarating. It's also lonely and scary. Friends want to hang but might not get it. Family has opinions, sometimes helpful, often unsolicited.
I started Free Agents because I couldn't find the space I needed back then. So I'm building it now.
HOW IT WORKS
Free. Lightweight. Small.
We meet once a month on a group call. There's a WhatsApp group for occasional updates. That's pretty much it.
GET IN TOUCH
Want to join?
Shoot me a message if something here resonates. I'll let you know what we're up to and whether it's the right time to join.
✉️ matt.r.yao [at] gmail [dot] com
© Matt Yao 2026
Palo Alto · ongoing