Cut From the NBA, Built a Million-Dollar Coaching Empire

Cut From the NBA, Built a Million-Dollar Coaching Empire

What does it take to turn 60 rejections into a nine-year pro basketball career and then build an entirely new business from scratch?

In this episode of From Underdog to Entrepreneur, Pat Miller sits down with Dre Baldwin, founder of Work On Your Game, a TEDx speaker, 43-time author, and former professional basketball player who spent nine years playing overseas. Dre shares how he went from a walk-on at a Division III college to building a company that helps entrepreneurs and experts install the mindset, systems, and strategy needed to scale from six to seven figures.

Dre opens up about cold-calling 60 basketball agents and mailing VHS tapes of his footage just to land his first pro contract and how he started posting training videos on YouTube back in 2005, years before "influencer" was even a word. That early audience-building experience taught him lessons about ownership, platforms, and personal branding that still guide his business today.

What You'll Learn Why being an underdog can actually be an execution advantage

How relationships and "tap-rooting" knowing someone who knows the right person open doors in business

The real difference between motivation and discipline, and why only one of them is repeatable

Why building on rented platforms (social media) means you don't actually own your audience

How relatability and authenticity build stronger connections than raw talent or fame

Why slowly transitioning clients to other team members protects a business built around one person

The importance of structure, self-discipline, and controlling distractions as your own boss

About Dre Baldwin Dre Baldwin is the founder of Work On Your Game, a company that helps experts and entrepreneurs install the mindset, systems, and strategy needed to scale their businesses from six to seven figures. He's a TEDx speaker and a 43-time author. Before entrepreneurship, Dre spent nine years as a professional basketball player overseas, mostly in Europe, after walking on at the Division III college level. While still playing, he began posting training videos on YouTube back in 2005, building an audience that eventually extended beyond basketball players to professionals and entrepreneurs interested in his lessons on discipline, confidence, and mental toughness. In 2015, he stopped playing basketball to focus full-time on that mindset-driven business, moving through professional speaking before shifting i