438 | Colby Wilson | How To Turn Failure into a $275K Comeback

What happens when early success turns into your biggest obstacle?

In this powerful conversation, Chris Thomson sits down with Colby Wilson, a Wilfrid Laurier business student and three-year Student Works Management Program veteran who’s now preparing to become a mini coach. After a strong rookie season and a complacent second year that nearly derailed his progress, Colby shares the turning point that reignited his drive, and how he built a $275K business through leadership, ownership, and humility.

He dives deep into lessons learned from failure, the mindset shift that rebuilt his confidence, and the joy of helping others believe in themselves.

Listen now because if you’ve ever felt “not ready” to lead, Colby’s story proves that greatness starts the moment you dive in headfirst. Don’t wait for perfect. Just start.

Timestamped Highlights

• [00:03:39] – Ambitious but naive: Colby’s life before Student Works
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• [00:05:30] – “An accelerated capsule of growth”: lessons from year one
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• [00:09:30] – The trap of complacency and how two lazy months cost him big
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• [00:12:08] – Facing failure, humility, and the moment everything changed
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• [00:17:15] – How clear planning and weekly execution rebuilt his business
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• [00:18:42] – The secret to enrolling a motivated team that owns the goal
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• [00:23:33] – What top performers like James, Landon, and Caleb all do differently
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• [00:27:13] – Why Colby is stepping up to coach the next generation of leaders
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About the Guest

Colby Wilson is a fourth-year business student at Wilfrid Laurier University and a three-time operator with the Student Works Management Program. After scaling his business from $100K to $275K, Colby is stepping into a new challenge as a mini coach, mentoring future entrepreneurs while running his own high-performing team. Known for his humility, grit, and growth mindset, Colby’s story reflects the transformation that happens when ambition meets accountability.

🔗 LinkedIn

Resources & Links Mentioned

• The Coaching Habit by Michael Bungay Stanier
• Actualize Club Performance Coaching (by Cam Russelle)
• Matthew McConaughey’s Oscar Acceptance Speech (leadership lesson)
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Important Links

• Connect with Chris: Website | LinkedIn
• Learn more about the Student Works Management Program
• Apply to be an Owner / Operator in the Management Program
• Looking for a fun job this summer? Summer Job Opportunities
• Hear more Alumni Success Stories

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