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HBO and The Ringer's Bill Simmons hosts the most downloaded sports podcast of all time, with a rotating crew of celebrities, athletes, and media staples, as well as mainstays like Cousin Sal, Joe House, and a slew of other friends and family members who always happen to be suspiciously available.
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Greg Bennick Returns: How to Avoid Comparison and Leap into the Dark | Chasing Curiosity and Sharing Boundless Insights from Ideas that Matter
The Growth Mixtape: Chasing Curiosity and Sharing Boundless Insights from Ideas that Matter
Manage episode 522263918 series 3550946
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Today we talk to Greg Bennick—writer, speaker, punk rocker, coin collector, juggler, and the first ever returning guest on the podcast.
Greg is one of those people whose passion is contagious. He can make anything interesting—coins, kindness, counterstamped nickels from 1860—and somehow ties it all back to living a life that actually means something. Our first conversation was the episode I recommended most when people asked what this podcast is all about, and this one might be even better.
We talk about the terrifying beauty of taking creative risks, the unexpected power of noodles in a hotel lobby, and why staying in the game—whatever your game is—might be the most important decision you ever make. He also shares what it’s been like to release his first book into the world, and why the chapter he almost left out might be the one that changes everything.
This conversation is about passion, purpose, and possibility.
Please enjoy, Greg Bennick.
Key Takeaways
- “Do it your way.” Greg shares how skipping the networking events at a major speaker conference—and eating Pad Thai alone in the hotel lobby—led to the most authentic connections of his career.
- Writing his first book taught him that vulnerability is part of the process—and that success often starts with just staying in the game.
- The chapter he almost didn’t include—on kindness—became the one readers connected with most. Sometimes others see the heart of your work more clearly than you do.
- Creativity isn’t magic—it’s a muscle. The breakthrough moments come after you’ve put in the reps, not before.
- Greg’s obsession with rare coins isn’t really about the coins—it’s about history, relationships, and finding connection in unlikely places.
- Comparison will kill you. We all assume everyone else has it figured out, but the truth is most of us are just doing our best to stay curious and keep going.
- Greg’s advice for anyone looking to start something new: Leap into the dark—not to fear failure, but to embrace the possibility of success.
- Purpose doesn’t have to be some grand external mission. Sometimes it’s sitting quietly in the lobby with a bowl of noodles, choosing to live a life that’s yours.
Connect with Bob Mathers
The Restless Leader Newsletter on Substack: https://bobmathers.substack.com/
Links & Resources
Greg’s website: https://www.gregbennick.com/
Greg on LinkedIn: https://www.linkedin.com/in/gregbennick
Greg on Instagram: https://www.instagram.com/gregbennick
54 episodes
