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March 18, 2025 45 mins

Today we talk to Syd "The Jewel" Vanderpool—former boxer with a pro record of 35-4 with 23 knockouts.  He was super middleweight champion and he did what virtually no boxers do - he walked away at the top of his game.  He now owns his own boxing gym, coaches Olympic athletes and works with business leaders to take what he learned in the ring to help them build thriving businesses of their own.


It’s hard to believe as I sit here in this comfy leather chair that Syd and I are the same species.  He had his first fight when he was 6 years old and spent his life getting in the ring with trained killers.  I’ve been in 2 fights in my life, they didn’t go well and I pretty much spent the rest of my life avoiding conflict.  But as Syd says, boxing isn’t about fighting - it’s about discipline, resilience and knowing when to stand your ground.  And that hit me right between the eyes.


Syd’s got some incredible stories from inside and outside the ring.  And he is a wisdom soundbite machine. Here are 2 I can’t get out of my head.

"If you don’t believe in yourself, no amount of training, coaching, or preparation will save you. At some point, you have to decide you belong."

"If you never feel like an imposter, you’re not pushing yourself hard enough.” 

Man, this conversation really hit home.  


Please enjoy, Sid Vanderpool.


Links & Resources


Follow Sid Vanderpool Online


Key Takeaways

  • The making of "The Jewel" – How Sid got his nickname and why it represents more than just a catchy ring name.
  • First fight at six years old?! – The wild story of how Sid’s boxing career started when his dad volunteered him on the spot.
  • The mental and emotional game.css-j9qmi7{display:-webkit-box;display:-webkit-flex;display:-ms-flexbox;display:flex;-webkit-flex-direction:row;-ms-flex-direction:row;flex-direction:row;font-weight:700;margin-bottom:1rem;margin-top:2.8rem;width:100%;-webkit-box-pack:start;-ms-flex-pack:start;-webkit-justify-content:start;justify-content:start;padding-left:5rem;}@media only screen and (max-width: 599px){.css-j9qmi7{padding-left:0;-webkit-box-pack:center;-ms-flex-pack:center;-webkit-justify-content:center;justify-content:center;}}.css-j9qmi7 svg{fill:#27292D;}.css-j9qmi7 .eagfbvw0{-webkit-align-items:center;-webkit-box-align:center;-ms-flex-align:center;align-items:center;color:#27292D;}
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