Athlete To Business: Make A Smooth Transition In Half The Time!

In Business & Entrepreneurship
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I’ve spoken to many audiences about making the transition from professional athletes to the business world. Most athletes, in the prime of their playing careers, don’t wanna hear about that shit. They just want to play the game and advance in the sport. 

Fair enough. 

When I worked with the NBA’s G-League, I asked Stacy, a former WNBA and overseas player who ran the league’s post-career preparation program, if the players were usually excited to hear from people like me. 

“(Laughs). No. They just wanna hoop.”

It’s an important topic though, one that’s very much needed. Pro sports careers are short. Most athletes are done in sports during their twenties; if you’re really good and lucky, you play into your thirties. 

Then you have 50 years remaining to live, and…

1) You probably don’t have enough money to roll around in it every day for the rest of your life like Scrooge McDuck. 

2) The further away you are from your sports glory, the less your sports glory matters. If you retired from baseball when you were 35 and now you’re 62, I don’t really care what you did in baseball. 

3) Nobody cares about a “former” professional athlete in general. You used to play? Cool story, bro. Who are you now

My secret is that I kind of cheated to know what I know about the transition to business and entrepreneurship. 

First of all, I went to college at an NCAA Division 3 school. There was no guarantee that I’d even have a professional sports career. So it was smart of me to have my eyes on other opportunities, just in case my pro sports ambitions didn’t happen. For most D3 athletes, they don’t. 

Second, I read Rich Dad, Poor Dad in college. That was my first lesson on entrepreneurship. I knew that’s where I belonged. 

Third, the internet started happening right as I was looking for said opportunities and possibilities. I started selling stuff on eBay in 2002. That’s when I was first introduced to copywriting, to get people to click on my listings (the headlines of my articles and subject lines of my emails are “copy”). 

Learned about selling myself on MySpace (for reference — Instagram, Facebook, Snap and Tik Tok are MySpace’s illegitimate children). 

Fourth, what we now call “social media” came out as soon as I left college. I started blogging first, then YouTubing. Started a website ( Then I created and sold my own products. 

All this time, I’m playing basketball overseas. But I knew that basketball ends eventually. And, here’s more random luck: NOBODY knows me from playing basketball overseas. Millions know me from publishing YouTube videos. 

Maybe, had I played for the Knicks or Lakers, I wouldn’t have gone so hard with the online stuff; being on ESPN would’ve served my ego enough. The energy was on the internet; so I put energy back into it. 

So, in a roundabout way, the stuff that didn’t work for me, worked for me. Had I been more successful at basketball, I may not have built a brand. 

What I’ll take full credit for: merging all of it together into one unifying theme that we now call “Work On Your Game.” 


As athletes, we all have to, at some point, transition from thinking of ourselves as athletes to thinking of ourselves as something else. The challenge: Usually, that “something else” is FAR less sexy than our athlete personas. 

That why I made episode #284: Mastering The Athlete-To-Business Transition. 

Listen here: