Dre Baldwin: From Athlete To Entrepreneur; 5 Work Ethic Lessons We Can Learn From Athletes

Business can get hectic fast when there’s no plan in place — the better a business is doing, the more important planning is.

As a part of our series about the work ethic lessons we can learn from professional athletes, I had the pleasure of interviewing Dre Baldwin.

Dre is a former 9-year pro basketball player who traveled 8 countries in his career after walking on at an NCAA Division 3 school.

Dre is now a full-time entrepreneur who has authored 27 books and performed 4 TEDxTalks on Discipline, Confidence, Mental Toughness & Personal Initiative. He has over 135,000 subscribers on YouTube, and his daily Work On Your Game podcast has been downloaded over 3 million times.

Dre built his company, Work On Your Game Inc. on giving as much “game” as possible to many people as possible.

Link to Dre’s webpage: https://dreallday.com/

Thank you so much for doing this with us! It is a great honor. Our readers would love to learn more about your personal background. Can you tell us the story of how you grew up?

Glad to be here!!

I’m from Philadelphia, PA, and started playing basketball at age 14. I was terrible at first, but stuck with it and finally made my high school varsity team as a senior — where I set the world on fire by averaging 2 points per game.

I walked on to play college basketball at the NCAA Division 3 level, and didn’t even play my senior season due to getting lost in the shuffle of a coaching change in the basketball program.

Undeterred, I hustled my way into professional basketball, piecing together a 9-year career that took me through 8 countries.

Concurrently, I built a brand around my basketball training content and mindset materials, which has led to me authoring 27 books and doing 4 TEDxTalks on the Mental Game.

What or who inspired you to pursue your career as a high level professional athlete?

What inspired me was the fact that I was always athletic and into sports; I started with football (never played officially as my family could not afford equipment) and then baseball (which I was not good at).

I decided around the age of 16 that I wanted to become a professional athlete, even though I had no official athletic success to my name at that point, no one taking me under their wing, and no blueprint for exactly how to do so.

None of us can achieve success without some help along the way. Was there a particular person who you feel gave you the most help or encouragement to be who you are today? Can you share a story about that?

I’ve always been what some people call a “sponge:” I soak up tidbits of knowledge and information from every source I come across! I learned from books, articles, an offhand comment from a teammate here and there.

There isn’t one person who stands out above everyone else — I give credit to every person who ever crossed my path, both positive and not-so-great. Everything played a part in inspiring me to achieve — especially the less-than-ideal experiences, which triggered my competitiveness.

If I had to credit a specific person, I’ll have to mention my parents: they laid the foundation of discipline, respecting authority, and following through on things I wanted.

Neither of my parents was an athlete — they’re 5’7” and 5’9” in height, while I sprouted to 6’4” — but I applied the lessons they taught to my sports experiences.

Can you share the funniest or most interesting mistake that occurred to you in the course of your sports career? What lesson or take away did you learn from that?

Only one??? Okay, sure…

The most interesting experience of my career was my time playing professionally in México.

My México experience was not a “mistake” — I wouldn’t trade the stories for anything — but if my time there was anything, it was unpredictable.

We (my American teammates and me) often didn’t know what towns we were in, when our next games would be, who we’d be playing against, and we sometimes played two or three games in the same day!

One teammate and I once got robbed by Mexican police while walking the streets late one night coming home from a nightclub. I caught an eye infection that had me thinking I was losing my vision; a toe infection that had me on crutches.

Luckily, I’d taken many years of Spanish classes in high school; midway through my stay in Mexico I was having full-on conversations with locals who didn’t speak a word of English.

My México experience was the most interesting, unpredictable and fun time I had of all the places I’ve seen as an athlete — off the court, at least.

OK, thank you for all of that. Let’s now shift to the core focus of our interview. Can you tell us the story of your transition from a professional athlete to a successful business person?


3–4 years into the start of my career, I found myself an unsigned free agent who was struggling to find my next playing opportunity. Though I surely wanted to continue playing, I also wanted to find or make a way to where I could control my income for the future.

It was then that I asked myself a great question: How can I combine doing the things I love (basketball + the Internet) with making money?

The result of my answer: investing more time into the small-but-growing following I was developing online via basketball and Mental Game content.

The audience I cultivated became my first customers when I started selling my own products a year later.

I didn’t stop playing basketball at this time — I was both playing Overseas Basketball while selling products online. I kept this up for 5–6 years before I stopped playing professionally and I’ve been a full time entrepreneur ever since.

What are some of the most interesting or exciting projects new you are working on now?

Right now I am building out The Overseas Basketball Blueprint, which is a full framework for basketball players who want to play professionally: all the tools they’ll need to start and further their career, to where their lives go after basketball.

Do you think your experience as a professional athlete gave you skills that make you a better entrepreneur? Can you give a story or example about what you mean?


One reason: Athletes have discipline instilled in us.

We’re used to showing up every day and doing the same things over and over again.

We’re used to hearing the same mottos from our coaches. We know what’s coming every day in practice or training, and even though it’s not always fun, we respect the process.

When I played overseas, we often had a 10:1 practices-to-games ratio. If you didn’t like practicing, you would grow to love it!

That discipline has paid off in many ways for me as an entrepreneur; one being that part of my brand philosophy is teaching discipline and how it contributes to growth and success in business, sports and life.

Another reason: Athletes are coachable.

No athlete walks into the business world knowing everything. We know this, so we seek out mentors and coaches who can show us what we don’t even know we are ignorant of.

I didn’t always agree with my coaches, and didn’t always like what they said to me. But it all helped to build me and improve my game — mentally, if not also physically.

In sports, even the best players still have coaches. In business, many entrepreneurs don’t follow this principle.

One more reason: Athletes understand performance culture.

In professional sports, you are judged 100% by your performance and results. You can’t fake it when you’re not performing; everyone can see you. And if you’re not producing results, you’ll be quickly replaced.

In Overseas Basketball, under performing players get released every day.

The business world is the same way, save for the fact that most businesses don’t have clear scoreboards like sports does: you have to create your own.

Ok. Here is the main question of our interview. Entrepreneurs and professional athletes share a common “hustle culture”. Can you share your “5 Work Ethic Lessons That Entrepreneurs Can Learn From Athletes”? Please share a story or an example for each.

1) Develop routines and habits.

As an athlete, I followed the same process every day of each aspect of my career — off season conditioning, in-season practice, or solo skill work.

I could execute my routines in my sleep, just from the sheer amount of repetition I’d been through.

Today, my business works much more smoothly when everything is done by routine, rather than everyone randomly deciding how to handle every challenge.

Routines are what make McDonald’s as great as it is: the food may not be the best, but the process is never deviated from!

2) Have a plan.

Business can get hectic fast when there’s no plan in place — the better a business is doing, the more important planning is.

There are too many things to be done, and too many things that we “can do” in business, to be working without a plan. Whenever I found myself working without a plan, I was always working extremely hard, fatigued at the end of the day, yet making very little progress.

The same thing happens in sports.

I couldn’t tell you how many times athletes have reached out to me, challenged with not knowing what to do on the court to work on their games. These questions led to me creating and selling training programs for players.

The small (or big) amount of time invested into up-front planning saves us lots of time on the back end; it also gives us a clear plan to follow every day at work, offering valuable peace of mind.

3) Maximize your strengths.

Often I speak to an up-and-coming basketball player and ask them what they plan to work on in the offseason to get better.

The common answer: “Everything.”

While this sounds good and makes logical sense — all of us are a work in progress, and nobody’s ever perfect — it’s not practical for a few reasons.

One, we can’t work on everything at the same time — and even if we were able to pull that off, the returns won’t be worth the effort because our focus is divided.

Secondly, not “everything” deserves the same level of our attention!

A great salesperson is better off focusing on sales and the complimentary skills that go with it (copywriting and marketing, for example) than on learning CSS coding for the company website. If a website update is needed, it would be much more efficient to hire for that skill than to learn it on your own.

Every professional basketball player needs a pro-level “differentiating skill” that separates them from other players. As a player, my best skill was my athleticism, and later in my career, my outside shooting.

Those skills alone made me more money than any other aspect of my game; and not because I wasn’t good at other things — but because in professional basketball, every player needs something that makes them stand out.

That “something” is always the player’s best strength.

In all areas of life, we get more out of maximizing what we’re good at than out of forcing ourselves to try and turn weaknesses into mediocrity (at best).

The world does not pay for mediocre products, people, or results — but it does pay handsomely for expertise and best-in-its-class abilities.

4) The RIGHT Work > Hard Work.

Related to the above point, knowing what to work on is just as important as the work itself.

As I have this brand and business called “Work On Your Game,” many people have misconstrued the message of the philosophy to mean they should just blindly work hard at everything and expect good things to occur as a result.

This could not be further from the truth.

One key aspect of success is choosing wisely. Business professionals should know where the highest potential ROI exists for each action they could take in their business.

When I was aiming to get into professional basketball, there were many routes I could take: try out for semipro teams; try to convince an agent to represent me; just keep practicing and hope something miraculous happens.

The best thing I could do, though, was attend an exposure camp (picture a job fair, but for athletes playing their sport on-location) and show my skills to a gym full of decision makers all at once. I’d also have the footage of the games I’d played in, which I could then show to any team or agents who had not seen me in person at the camp.

That choice paid off: my first exposure camp performance launched my basketball career.

5) Have a unique angle.

As I explained above regarding differentiating skills, entrepreneurs need to differentiate themselves from the crowd the same way.

Professional sports teams look for players based on the skills they feel would best compliment their teams — and they canvas the landscape for the players who fit those needs. The better a player is known for having the needed skill, the higher the probability they’ll be the player a team comes looking for.

It’s the same in business. Entrepreneurs need to decide what exactly they want their audience, and the wider marketplace, to know them for. The more established you are in “owning” a specific niche area, the more you’ll dominate the minds of the consumers who are looking for it.

What would you advise to a young person who aspires to follow your footsteps and emulate your career? What advice would you give?

Self-educate as soon as possible!

The best knowledge I gained did not come from school, even though I have a business degree from Penn State University. The most important and most applicable knowledge I have came from my own independent reading of books, enrolling in courses, mentorship, and personal experience.

Self education is something that I wish I knew about and was more intentional about earlier in life.

In the course of this self-education, get deeply immersed in personal development.

I define personal development as any material or experience that makes you better, smarter and an overall more valuable person to yourself and to others.

Books are great for this, as the author is taking the most essential aspects of years of learning and experience and condensing it down into a few hundred pages or so — you’re getting 1–50 years of life experience in 3 weeks (or however long it takes you to read a book). That’s a great return on investment.

You are by all accounts a very successful person. How have you used your success to bring goodness to the world?

That’s the only thing I’ve been doing since I started!

My brand started with me sharing material for improving at basketball, then evolved into Mental Game materials and then overall personal growth and development. Today I still do those things, along with helping people advance in their business and sports careers.

If I wasn’t giving people value, I would have no resume to speak of.

My business grows only one way: by making other people better and showing them how to keep the process going even after finishing the book or after the speech is over or the consulting call ends.

You are a person of enormous influence. If you could inspire a movement that would bring the most amount of good to the most amount of people, what would that be? You never know what your idea can trigger. 🙂

That movement is “Work On Your Game!!” It’s about developing your game, making yourself better from the inside-out and never allowing circumstances to hold you back.

Can you share your favorite “Life Lesson Quote”? Why does that resonate with you so much?

My favorite quote is “Work On Your Game” — one reason being that I created it, and because it will be forever connected to me.

I’ve always believed that people need to be their own inspiration at times, as we won’t always be able to call on others or watch someone’s video to get ourselves activated.

This quote inspires anyone to run off of your own energy — which is the highest peak of self-reliance!

We are very blessed that some of the biggest names in Business, VC funding, Sports, and Entertainment read this column. Is there a person in the world, or in the US whom you would love to have a private breakfast or lunch with, and why? He or she might just see this, especially if we both tag them 🙂

Sean Combs. I’ve never met him, but he’s been a virtual mentor of mine for a long time who I look to for inspiration when I’m not looking to myself.

Many times, Sean wasn’t even the most talented person in the room — but he put all the talented people in place to be their best. Everyone he worked with did better with him than they did without him.

I’d want to learn about his leadership principles, focus and vision.

Learn more about Meditation