Dre Baldwin

Success occurs from the inside-out: your inner Mental Game determines your actions, and those actions determine your results. Master your Mental Game and the actions will take care of themselves.


In just 5 years, Dre Baldwin went from his high school team’s bench to the first contract of a 9-year professional basketball career. Concurrently, Dre pioneered new genres of personal branding via content publishing.

Dre has been blogging since 2005 and began publishing video to YouTube in 2006. He has over 7,000 published videos, with content going out to 134,000+ subscribers and being viewed over 44 million times. Dre’s daily Work On Your Game Show has over 1,300 episodes and 2.5 million downloads.

Dre has given 4 TED Talks on Discipline, Confidence, Mental Toughness & Personal Initiative and has authored 25 books. Dre 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.

Where did the idea for Work On Your Game Inc. come from?

The idea for Work On Your Game Inc. came from me talking to my audience back in 2009.

I’d already been regularly publishing basketball training videos and was starting to get a lot of questions from viewers, most centered around how they could improve at the game.

I recorded a video in the gym right after a workout and explained, very directly, that many players were failing at the game because they were playing xbox, hanging out and watching me instead of doing what they needed to be doing: Working On Your F***ing Game.

Viewers commented that they liked the phrase and I kept using it. When I made my business official, there wasn’t a need for alternate naming ideas.

What does your typical day look like and how do you make it productive?

Wake between 3:40-4AM
Yoga + meditation
Workout (running or gym)
Shower & dress
Morning walk
Protein shake
** work begins 7:30 AM **
Daily work consists of: writing, recording, outreach (for media & speaking engagements), product and sales funnel creation.

How do you bring ideas to life?

Think of something
Do it!
If it works — do more. If not — discard

What’s one trend that excites you?

Everyone is creating and publishing content now — which makes it even more obvious what GOOD content looks, reads and sounds like.

I know the value of my content — both my personal opinion and proven results of my audience — so every new player in the content world only makes it more clear how valuable my contribution is.

What is one habit of yours that makes you more productive as an entrepreneur?

Learn – codify – delegate.

I learn how to perform a certain task on my own (or at least most of that task, so I have a clear understanding of what I want and how it needs to be done).

Then I codify the process, so I am able to explain to anyone what I want done and how it should be done (and if you have a better way, tell me!).

Then I can delegate that work to others and (eventually) do ONLY things that I’m great at and that I enjoy doing. This is an ongoing process.

What advice would you give your younger self?

Invest in your self-education!

School is the last time in life when someone will force you to learn what they’re teaching. After that, any education you acquire will be acquired by choice, not by default.

I went to school and have a business degree from Penn State University — but I don’t use anything that I learned there in my daily business.

All that knowledge came from books, conferences, podcasts, mentors, coaches and the rest. I wish someone had told me about that sooner so I could have been doing more or it more intentionally earlier in my life.

Tell us something that’s true that almost nobody agrees with you on.

There is no such thing as “Too Much Confidence.”

Confidence, when we look at other people’s, is relative. The phrases “cocky” and “arrogant” are matters of judgment, not objective reasoning. We only see someone as having “too much” when we ourselves don’t have enough.

Get around different people, and the same traits that made people judge you negatively could not be celebrated.

Most people are afraid of becoming “too confident” merely due to the judgements they’ll receive from their peer group. The truth is, though, that most people have never come close to having enough confidence, let alone “too much” of it.

Think about it: how many times has “too much confidence” caused a problem in your life…?

Now — how many times has a LACK of confidence hurt you or cost you an opportunity???

As an entrepreneur, what is the one thing you do over and over and recommend everyone else do?

As a subject-matter expert, it’s important for me to start top-of-mind with my audience — so I publish a lot.

Publishing allows me to reach and engage with my audience.
It forces me to make sense of my ideas in such a way that others can understand them.
Publishing puts me in position to figure out what parts of my experiences and observations can be translated in a way that relates to my area of expertise, a creativity exercise.

What is one strategy that has helped you grow your business?

Learning to use sales funnels and systematize customer experience.

Sales funnels take customers to the “next step” automatically, which allows me to offer more and more value to people without having to remember to do it manually (which is nearly impossible with even just 100 paying clients).

Sales funnels use emails, landing pages, order forms, upsells, advertisements, even free content — the strategy I’ve used is to continue learning about utilizing and optimizing all aspects of funnels to make my business more predictable for both me and my clients.

What is one failure you had as an entrepreneur, and how did you overcome it?

Spending too much time chasing speaking gigs. Speaking gigs are fun and a great ego boost — but they are one-off sales that require you to go and get another one after that current one is done. You’re constantly chasing them.

I overcome this by investing more into my own content and serving them with my self-contained products and services, and spreading my message that way — which led to speaking opportunities coming to me instead.

What is one business idea that you’re willing to give away to our readers?

Create an application that allows someone to live stream to all the streaming platforms — Instagram, YouTube, Facebook, Periscope, anyone else — from one feed at the same time.

This would be great for everyone who doesn’t have the luxury of multiple phones / tablets, and / or who would like to live stream on the go and isn’t set up in a studio — but wants to reach all their audiences at once.

What is the best $100 you recently spent? What and why?

Buying books on amazon and audible!!

Authors take years of their lives to do research or take years of living life and condense that into 250-300 pages. If the book takes you 3 months to read, you’ve acquired 5 or 10 years of experience in 90 days!

Books are one of the best investments you can possibly make for a small amount of money.

What is one piece of software or a web service that helps you be productive?

Google Docs, the free web-based word processor from Google. I do all my articles and book writing there, and keep the notes for my podcasts in Docs. It’s also where I take notes when I attend events and read books or take courses.

What is the one book that you recommend our community should read and why?

Good To Great by Jim Collins. The book explains the main elements that make a company exceptional — and even if you’re not a publicly-traded organization like the ones Collins studied for his book (mine is not either), the principles shared apply across the board not just in business but in life.

What is your favorite quote?

“Work On Your Game.” – Dre Baldwin

Key Learnings:

  • Success occurs from the inside-out: your inner Mental Game determines your actions, and those actions determine your results. Master your Mental Game and the actions will take care of themselves.
  • Master your communication skills. You’ll need this for conveying your message to your audience, to properly lead your team, and most importantly, to deal with yourself!
  • Never stop investing in yourself and your business. Once you complete your formal education, any and all learning you do will be by choice. Take ownership of your post-school education!