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

• Sid Vanderpool’s Gym (SydFit Health Centre) – Boxing training for all levels, from beginners to elite athletes. 
• Boxing Gym Growth Academy – Coaching for gym owners to build successful businesses.
• Champion for Charity Boxing Event - Annual boxing event raising money for McMaster Children’s Hospital and other charities.

• LinkedIn
• Instagram
• Facebook

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 – Why fear, self-doubt, and emotional regulation play a bigger role in boxing (and life) than most people realize.
• Knowing when to walk away – How Sid made the rare, smart decision to retire before taking too much damage—a choice most fighters struggle with.
• What happened to boxing? – Why the sport isn’t in the spotlight like it was in the Ali and Tyson eras, and how UFC stepped in.
• Coaching beyond the ring – Sid’s work training not just fighters, but also gym owners and business leaders on discipline, strategy, and resilience.
• Stepping outside your comfort zone – Whether it’s boxing, business, or life, pushing past fear is where real growth happens.

Every other week, join your host Bob Mathers, keynote speaker for conversations designed to push you out of your comfort zone. Each episode delivers boundless insights and ideas that matter by inspiring you to get off autopilot and keep chasing curiosity.