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Misfit Entrepreneur 15: Kelly Roach

Dave Lukas Chats with Dre Baldwin

432:  Work on Your Game, How Dre Baldwin Turned Hustle, YouTube, and Discipline Into a Thriving Business Empire

This week’s Misfit Entrepreneur is Dre Baldwin.  Dre is an interesting entrepreneur who owns the brand, Work on Your Game.  He is a former pro-basketball player playing in 8 countries during this career.  But, he wasn’t a superstar from the start.  He had to work harder than anyone and walk on at a division 3 school to get his shot.  And he made the most of it succeeding and turning pro.

He was an early adopter of YouTube and has a massive following and since leaving pro basketball, he has authored 35 books, created over 400 products, given 4 Ted Talks on Discipline, Confidence, Mental Toughness, and Personal Initiative.  His daily Work on Your Game Masterclass has been downloaded over 7.5 million times! 

Hearing all of that, you can see why I asked him to be on the show and I love his no-nonsense straightforward approach to success because it’s a lot like mine.

www.WorkonYourGame.com 

​Free Copy Dre's New Book:  The Third Day
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Show Notes

Dre grew up in Philadelphia .  His journey into basketball began at age 14 after exploring other sports. Despite challenges, including only making his high school team as a senior and sitting on the bench, he pursued his passion for basketball. He walked on at a Division III college team and hustled to turn pro after graduation, attending an exposure camp and then hustling to get and agent. His pro career began in Lithuania in 2005. Simultaneously, Dre became an early adopter of YouTube, initially uploading content to preserve basketball footage. Over time, he discovered an audience eager to learn from him. This realization marked the start of building his personal brand, which evolved into a thriving business teaching discipline, confidence, mental toughness, and personal initiative.

What does it really mean to "work on your game"?
  • Understand Your Game: Clearly identify what "game" or business you are in. Many people think they’re in one area but are actually playing another.
  • Develop Your Skills: Hone the specific skills needed to succeed in that game.
  • Perform and Produce Results: Apply those skills consistently to achieve tangible outcomes and reap rewards.

How can people discover what game they’re truly in?
  • Ask Insightful Questions: The key is asking individuals reflective questions to help them uncover their true path.
  • Focus on What They Say: Use their own insights to guide them toward clarity.
  • Reveal the "Real Reason": Often, people's surface-level answers are not the root of their desires. Dig deeper into their emotional motivations.

How do the four pillars—discipline, confidence, mental toughness, and personal initiative—work together?
  • Discipline: The ability to show up and do the work consistently, regardless of motivation.
  • Confidence: Built on disciplined effort and progress, enabling belief in one’s abilities.
  • Mental Toughness: Acts as a shield for mental health, ensuring perseverance when things get tough.
  • Personal Initiative: The drive to take action and turn thoughts into results.

How can people tap into their "burning desire"?
  • Ask "Why?": Repeatedly question why you want something to uncover emotional motivations.
  • Combine Logic and Emotion: Logic acts as the steering wheel, but emotion is the gas pedal that propels action.
  • Be Honest: Identify the deeply personal reasons driving you, even if they’re not socially acceptable to share.

"Your emotions are the gas pedal, and your logic is the steering wheel. You need both, but your emotions fuel the fire to take action. Without emotional investment, you won’t move forward."

What steps can someone take to create success online?
  • Serve Your Audience: Start by answering questions from those you aim to serve, especially if they are in a position you were once in.
  • Repackage Messages: Deliver the same core messages in different ways to engage a broader audience.
  • Stay Consistent: Post content regularly and maintain discipline even when growth feels slow.

 What are the benefits of waking up at 3:45 a.m. every day?
  • Dre started this habit to make time for basketball workouts while working a corporate job.
  • He values the edge it provides—by early morning, he’s accomplished more than most do in a full day.
  • Though now modified with a "smart alarm" since becoming a parent, the habit continues to fuel his productivity.

 What lessons from being a pro athlete have helped you in entrepreneurship?
  • Performance Matters: The scoreboard is an objective measure of results, free from bias or politics.
  • Meritocracy Mindset: Sports taught Dre the importance of earning rewards through performance, a principle he carries into business.
  • Resilience: Success is not guaranteed by talent alone—strategy, persistence, and adaptability are crucial.

What advice do you have for aspiring African-American entrepreneurs?
  • "The same as I would give to any entrepreneur..."
  • Provide Value: Identify a problem, offer a solution, market it effectively, and ask for the sale.
  • Avoid Victim Mentality: Focus on mindset and resilience rather than external challenges.
  • Learn from Success Stories: Seek inspiration and strategies from others who have succeeded.

​"Life is a performance and results-based business. Your rewards are determined by the results you produce, not by your story. People care about your story only after you’ve achieved the results."

Best Quote

  • Discipline is your willingness and ability to show up day after day to do the work, even when you don't feel motivated. Professionals rely on discipline, not motivation, because motivation doesn't always show up, but discipline does
Misfit Three

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 Life is Results-Based: Rewards are earned through performance, not stories. Results open doors and inspire   others to care about your journey.

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Turn Motivation Into Discipline: Motivation is fleeting, but discipline sustains long-term success.

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You Don’t Have Time: Act with urgency and avoid procrastination. Life is finite, and no one is guaranteed more time.


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