Built Online Podcast: How He Has Turned Sports Lessons Into Entrepreneurial Success | ft. Dre Baldwin

Host: Cody McGuffie
Guest: Dre Baldwin
Release Date: September 15, 2025

Episode Overview

In this episode of the Built Online podcast, host Cody McGuffie speaks with Dre Baldwin—former pro basketball player turned entrepreneur, author, and founder of the 'Work On Your Game' company. Dre shares how the mindset, discipline, and systems he cultivated in sports have translated into lasting business success. The conversation is rich with actionable insight for aspiring and active entrepreneurs, focusing on the mental game, building effective habits, and turning challenge into opportunity.

Key Discussion Points & Insights

Dre’s Background and Entrepreneurial Journey

[01:16-03:07]

• Dre grew up in Philadelphia, started basketball at 14 (late by competitive standards), played Division 3, but was overlooked for pro opportunities. He hustled his way into a pro basketball career overseas, playing in eight countries over nine years.
• In 2005, Dre began posting VHS footage on the early YouTube platform, building brand momentum first among basketball players, then among a wider audience as he moved into topics like mindset.
• By 2010, he was monetizing content, self-publishing books, and developing what would become his company, Work On Your Game, systematizing and teaching the discipline, performance, and accountability gained from sports.

Core Principles: From Sports to Business

[03:54-05:06]

• Dre’s ideal client isn’t an athlete but a high-performing entrepreneur—someone striving for ownership, control, and excellence.
• Universal Mindset: “The principles I pulled out of sports are universal. They're profession agnostic.” – Dre Baldwin [04:13]

The Inner Game of Success

[06:10-08:46]

• Dre asserts that real, sustainable success starts with identity and mindset, not simply action:

  • 3-Step Process:
    1. Outcome (Goal)
    2. Actions (The Work)
    3. Being (Who You Are)
  • “Success starts on the inside… Success is something that you are doing. It's not an achievement. It's not a destination.” – Dre Baldwin [08:31]

• Dre cites Earl Nightingale’s definition: “Success is the pursuit of a worthy ideal.”

Why Being > Doing

[09:32-12:28]

• Dre explains why people with the same knowledge and actions may get different results—it’s about your internal posture and who you are being.
• “Until we change the mindset, the internal posture of the person, they can have all the information in the world… They still won't act on the information because… their internal posture has not become the type of person who would do those things.” – Dre Baldwin [11:53]

How to Change Your Internal Identity

[12:41-21:51] Dre outlines three key methods for mental conditioning and identity shift:

1. Repetition
   • Repeating thought patterns or actions until they’re internalized. (“You sing the ABC song a million times, so you know the letters.” – Dre Baldwin [13:49])
   • Practical comparison to muscle memory in basketball and driving to work.
2. Emotionalization
   • Experiencing something with enough emotional charge can fast-track subconscious programming. (“Emotion contains energy, and energy… can alter you immediately.” – Dre Baldwin [16:18])
   • Using motivational speakers and music as tools for emotionalization.
3. Immersion
   • Placing yourself in new, focused environments (conferences, communities) where growth behaviors are modelled and supported.
   • “When you're immersed in a certain energy, you are more likely to do things that you wouldn't do if you are home by yourself.” – Dre Baldwin [19:45]

“You combine all three—immersion, emotionalization, and repetition—you can reprogram the subconscious mind to be anything that you want it to be.” – Dre Baldwin [21:37]

How Long Does It Take?

[22:28-24:05]

• There’s no expiration date or endpoint—you continually practice being successful. Referencing his YouTube advice, Dre says: “How long do you want to be good?... The best performers… continually keep their game sharp even once they get to the point of being good.”

Building a Legacy Business

[24:15–25:14]

• Dre’s current mission is to codify his framework so that it stands alone—so that companies like Microsoft could implement his concepts even if he isn’t there.
• “I want to be more of the driver and then eventually more of the passenger and let the engine be the entity of work on your game.” – Dre Baldwin [24:17]

Notable Quotes & Memorable Moments

• On Success:
  “Success starts on the inside… as soon as you achieve [a goal] and you don't have anything else to go after next, at that moment, you're not a success. Right? Success is something that you are doing.”
  — Dre Baldwin [08:31]

• On Mindset vs. Action:
  “Most people usually logically understand: ‘I'm going to have to do something different.’... but until we change the mindset, the internal posture... they still won't act on the information.”
  — Dre Baldwin [11:42]

• On Subconscious Reprogramming:
  “The subconscious mind is programmed or altered in three specific ways: repetition, emotionalization, and immersion.”
  — Dre Baldwin [13:49]

Rapid Fire Segment

Favorite business book?

• “48 Laws of Power by Robert Greene.” – Dre Baldwin [26:50]

Biggest lesson before starting?

• “That you had to sell people what they want while at the same time giving them what they need… It's kind of like feeding medicine to a dog. Dog needs the medicine. But if you just give them the pill, they won't eat it. So you have to hide it in some deli meat so they actually eat it.”
  — Dre Baldwin [26:58, 27:11]

Worst advice received?

• “You need to have a website and an LLC before you start your business… It's an excuse that a lot of people use to not actually get started.”
  — Dre Baldwin [27:56, 28:06]

How many hours per week do you work?

• “I've been a 60 hour a week guy, but I'm getting that down… more about effectiveness than just productivity. A lot of entrepreneurs… are looking for productivity when what they really need is effectiveness.”
  — Dre Baldwin [28:38, 29:44]

Athlete’s Perspective and Entrepreneurship

[32:06-34:21]

• Dre and Cody both reflect on how relentless effort (grinding) helped them in sports and business, but both are now shifting to more effective, leveraged approaches.

• Business, unlike sports, isn’t a pure meritocracy: “In the business world, you can outwork your competition and still come in last place.”
  — Dre Baldwin [32:22]

• “There comes a point in entrepreneurship… the hard work and the grinding is necessary until you get to a certain point… Then you get to an inflection point where you have to evolve.”
  — Dre Baldwin [32:59]

Resources & Where to Find Dre

[34:42-35:01]

• Main site: workonyourgame.com
• Search “Dre Baldwin” on any social media platform

For Listeners

This episode is a playbook for anyone looking to instill the athlete's mindset of continuous improvement, discipline, and resilience into their entrepreneurial journey. Dre’s frameworks for inner work, practical mental conditioning, and creating a business that outlasts your personal hustle are especially valuable for those ready for their next level.

Listen to the full episode for Dre’s actionable insights and strategies for building lasting success.