We caught up with the brilliant and insightful Dre Baldwin a few weeks ago and have shared our conversation below.
Dre, appreciate you joining us today. Getting that first client is always an exciting milestone. Can you talk to us about how you got your first customer who wasn’t a friend, family, or acquaintance?
Well, that would be two different stories.
My first dollar was not a client, but a customer of a product that I created. I first got myself known online through publishing basketball training drills to YouTube; the players who were watching me eventually asked me if I could make programs that would allow them to train themselves the same way that I trained myself.
So, my first dollar as an entrepreneur making my own stuff was a $5 sale of a training program for basketball players to practice dribbling and shooting in 2009. At the time I was still playing professional basketball, but the sale showed me what I could do long after I would be done playing.
My first client, on the other hand, found me through a live streaming app called Periscope that no longer exists. I used to do 15 minute Livestreams every day sharing principles of mindset, business, strategy, and professional development. One day a viewer asked me if I offered coaching. I told him I did, even though at the time I had never offered to coach anyone. He sent me an email, and I sold him coaching!
Once I got to working with him, I realized that the stuff that he was asking me about were things that I absolutely could help with; and coaching him told me that there were probably many other people who had the same challenges that he did. That’s how I got into the coaching business.

As always, we appreciate you sharing your insights and we’ve got a few more questions for you, but before we get to all of that can you take a minute to introduce yourself and give our readers some of your back background and context?
I got into business by sharing value with my audience for free through social media (before it was even called “social media”).
At first I was blogging, then came YouTube, then live streaming, podcasting, and the rest. People started finding me through the free value I was giving out, and asking if I had higher-level or personalized materials for sale. And that is literally how I started my business.
What separates me from others in my space is that I do not sugarcoat my points, I get straight to the point, and I do not address topics with kid gloves, so to speak.
I come from the professional sports world, where we get told things straight, with no chaser. Professional athletes are in the top 1% of what we do because we are required to perform at a high-level every single time out; if you don’t, you will not have a job.
When you are going against the top 1% of your profession every day, you can’t afford to have messages sugarcoated for you. You need to know the truth, the whole truth, and nothing but the truth — and then you need to do something about it. That is what I do for professionals in the business world.
I not only have the insight and understanding to see it, I also have the communication skills to share and teach it.
Any insights you can share with us about how you built up your social media presence?
I built my presence on social media, mostly because I was not trying to just do social media for the purpose of chasing a dollar.
I built my presence because I was giving people valuable, useful material that led them to knowing, liking and trusting me. Then they spread the word about me to their friends, and it went on from there.
Many people get into social media these days just because they feel it’s a necessary evil to get to the money; I got onto social media because I wanted to give people the insight and information that no one had given to me.
The advice I would give to anyone using social media today to build a brand in business is to focus on giving people value, and make sure that your free material is higher quality than your competitors’ paid material. to this day, the stuff that I put out for free is better than what a lot of people offer for sale.
How about pivoting – can you share the story of a time you’ve had to pivot?
Every professional athlete will have to, at some point, pivot from being a pro athlete to being something else.
The good news for me was that I came from a very humble background in sports as a Division III athlete. So, there was no guarantee that I would ever have become a professional in the first place. Because of this, I already had my mind on what I would be doing after sports, because my after-sport life may have started sooner rather than later.
To that end, I had my mind on entrepreneurship before my career even began. So, when I found myself in-between jobs as an athlete, it wasn’t hard for me, mentally, to start looking into ways of taking control over my income and career opportunities. The good news was that the Internet was starting to become what we now know it as at the same time that this happened.
I started creating and selling my own products right in the middle of my professional athlete career, so when I decided to stop playing professional sports, I already had momentum, products, an idea, and a brand already in place. I didn’t wake up the day after my career was over starting at zero. I already knew exactly what I was doing and how I would be doing it.
So my less-than-stellar athletic background paced the way for an smoother start in pivoting to business.
Contact Info:
- Website: WorkOnYourGame.com
- Instagram: http://Instagram.com/DreBaldwin
- Facebook: http://Facebook.com/WorkOnYourGame
- Linkedin: http://LinkedIn.com/in/DreAllDay
- Twitter: http://Twitter.com/DreAllDay
- Youtube: http://YouTube.com/Dreupt
- Other: http://clubhouse.com/@drebaldwin

