We recently had the chance to connect with Dre Baldwin and have shared our conversation below.
Dre, we’re thrilled to have you with us today. Before we jump into your intro and the heart of the interview, let’s start with a bit of an ice breaker: What are you most proud of building — that nobody sees?
The personal discipline of waking up every morning and training when no one is watching.
It’s not about motivation — it’s about showing up whether I feel like it or not. That physical discipline carries over into everything else I do. It’s where my structure starts. It’s what gives me the authority to speak on mindset, performance, and consistency — because I live it before I ever say it. Most people never see it happen, but they feel the results of it every time I show up.
Can you briefly introduce yourself and share what makes you or your brand unique?
My name is Dre Baldwin — I’m the CEO and founder of Work On Your Game Inc. I’m a former 9-year professional basketball player turned author, speaker, and business coach. My brand is built around helping high performers apply structure, discipline, and mental toughness to dominate in business and life. I’ve written 41 books, delivered 4 TEDx Talks, and created over 50 courses — all focused on mindset, strategy, systems, and accountability. What makes my brand unique is that everything I teach, I’ve lived. From the discipline of showing up daily as an athlete to building a multi-six-figure coaching business from scratch — Work On Your Game is more than a brand. It’s a lifestyle.
Okay, so here’s a deep one: Who taught you the most about work?
My parents.
They didn’t work glamorous jobs — but they got up every day and went to work, even when I’m sure they didn’t feel like it and probably didn’t enjoy what they were doing. That daily consistency taught me discipline and work ethic by example. Even though I’ve chosen completely different fields than they did, the foundation they set has stayed with me every step of the way.
What did suffering teach you that success never could?
Suffering taught me that most people quit the moment things get tough — often before it even gets truly hard. They lack mental toughness, internal discipline, and personal standards. They don’t know how to hold themselves accountable when no one’s watching. I’ve been through challenging times and kept showing up with the same energy and execution — whether things were going great or falling apart. That consistency is rare, and suffering revealed just how few people are built for it. Success could never teach me that, because success hides weakness — struggle exposes it.
Alright, so if you are open to it, let’s explore some philosophical questions that touch on your values and worldview. Where are smart people getting it totally wrong today?
Smart people today are getting it wrong by thinking that information or facts still win arguments or change minds. They don’t. We live in a world where no one is obligated to accept truth — even when it’s accurate and well-presented. People choose their realities, and thanks to algorithms and echo chambers, they can reinforce their beliefs no matter how flawed. So the game isn’t about who has the best facts anymore — it’s about who has the most influence. The real power now lies in your ability to persuade, resonate, and mobilize, not just inform.
Okay, we’ve made it essentially to the end. One last question before you go. What will you regret not doing?
Every pretty woman I ever saw looking my way that I didn’t immediately approach. That’s the tongue-in-cheek answer — but it’s also real. And it speaks to a bigger principle: we almost always regret what we didn’t do more than what we did. Especially when the opportunity was a coin flip. The truth is, most people live without courage. They talk a big game but don’t act. The ones who do — the ones who take the shot — win far more often than they lose. Not because the odds are better, but because they actually stepped up.
Contact Info:
- Website: http://www.WorkOnYourGame.com
- Instagram: http://Instagram.com/DreBaldwin
- Linkedin: http://LinkedIn.com/in/DreAllDay
- Twitter: http://X.com/DreAllDay
- Facebook: http://Facebook.com/WorkOnYourGameUniversity
- Youtube: http://YouTube.com/Dreupt
