In just 5 years, Dre Baldwin went from the end of his high school team’s bench, to the first contract of a 9-year professional basketball career. While playing professional basketball, Dre pioneered new genres of personal branding and entrepreneurship via an ever-growing content publishing empire. Dre started blogging in 2005 and began publishing videos to YouTube in 2006. He has published over 7,000 videos to 134,000+ subscribers, his content being viewed over 73 million times to date. Dre’s daily Work On Your Game Podcast MasterClass has over 1,500 episodes and more than 3 million downloads. Dre has given 4 TED Talks on Discipline, Confidence, Mental Toughness & Personal Initiative and has authored 27 books. He has appeared in national campaigns with Nike, Finish Line, Wendy’s, Gatorade, Buick, Wilson Sports, STASH Investments and DIME magazine. A Philadelphia native and Penn State alum, Dre lives in Miami.

What is your business and what do you do?

At Work On Your Game, we help people get to the top of their “game” — those games can range from the up-and-coming & professional athletes we’ve worked with from my sports background, to the entrepreneurs and business professionals we serve today. When I first started out online, I was simply publishing basketball workouts for players to learn from. That led to me making content about the “Mental Game” tools of Discipline, Confidence, Mental Toughness & Personal Initiative that players asked me about — and in doing that, I attracted an audience of non-athletes who told me that my messages applied outside of the sports world! That planted the seed in my mind that, after my pro basketball career, I had an open lane to serve an audience of people who didn’t play sports. Today our clients are small business owners, entrepreneurs and athletes looking to join the pros. 

What sparked your vision to launch your business? 

The vision for my business was sparked by the understanding that sports careers don’t last long, and my challenges in not always knowing when my next playing contract would happen. That forced me to start thinking critically about life after sports, even while I was still playing: I could see the uncertainty in my career and needed some control over my destiny. It naturally led me to entrepreneurship, as I’ve always been into selling and I love the “blank canvas” that the internet presented when it came to crafting a message and image for an audience. Plus, I didn’t want any parts of a “regular job” — growing up, I’d seen the adults around me working those and none of them ever seemed excited to go to work! 

What has been your favorite failure and what did you learn? 

I wouldn’t classify any of my failures as “favorite,” but I’d say the year I spent after college working those very “regular jobs” that I despised before singing my first professional basketball contract. That year was a challenge to my vision, discipline and mental toughness since I had no professional prospects and there was also very little information out there about how exactly to play professional basketball overseas (information that I’ve since created). What I learned was that I had a skill of perseverance that many of my peers simply didn’t have — that year away from the game caused most players to give up on the goal of joining the top 1% of professional athletes. The fact that I stuck with it and made it happen became the very foundation of my brand and business. 

What was your most memorable day of your career and why?

That’s easy: As an entrepreneur, the day when I created and released my first ever product: a $4.99 self-training program for basketball players. People actually went and bought it! This was huge for me because I realized something: I could create an idea and a product from nothing more than an idea and make money from it. When this happened, I immediately knew that creating products and selling them was my calling — and a skill that would last longer than my 40-inch vertical in basketball. 

How do you continue to learn so you stay ahead in your industry? 

I’m always taking in information — from books, podcasts, articles, videos — that not only bolster my knowledge, but that also material that challenges my thinking and opens my mind to new ways of seeing things. At the same time, I produce more than I consume: I create and publish new content every single day, which I have been doing for over 15 years online. I focus on a few people who I trust to have solid knowledge on certain topics, and don’t allow myself to drown in the sea of information online, which is endless. 

What is some bad advice you hear in your industry or with entrepreneurship that people should avoid?

“Fake It ‘Til You Make It.” This is bad advice because the human brain can’t be fooled by “faking!” If you want to create real change from within, don’t fake it — decide that you have BECOME it and live it out — at that point it’s real, not fake. This can happen in an instant and it fully based on how you choose to see yourself when you look in the mirror. 

Where can readers find you on social media?