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Work On Your Game Content/Overseas Basketball/The Basketball Failings That Made Me An Entrepreneur
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The Basketball Failings That Made Me An Entrepreneur

“This stuff that I’m doing online, with my website and blog and YouTube — this is gonna be something. I don’t know exactly what it’s gonna be, but it’s something — and I think this online stuff is going to be bigger, for me, than even playing basketball.”

— Me to a friend, 2009

In 2008, I was at a crossroads.

I’d played professionally in 4 countries and had returned home from what I saw as a successful stint in Herceg Novi, Montenegro, a deal I had created and closed myself.

Early in my career at some exposure camps I attended, sometimes the event organizers put together a “player file,” a booklet with a page for each player. It listed the player’s vitals: height, weight, age, background etc. l read those files and saw that some players I was competing against already had professional resumes; they were at the camp to make an even better situation for themselves.
I watched some of them play, referencing the player files, and some of these seasoned pros were not very good.
HE played in Germany?
How did THIS GUY get a deal in Finland?
DUDE was playing overseas last year?
Those feelings led me to making a decision.

When my college career had ended ahead of schedule, making the pros would put posterity on my side compared to my college ex-teammates. With these professionals, I now had to do more than just “play overseas” one time; doing that would put me in the same basket as some of the bums I saw playing at the exposure camps. I needed to be more than a one-off pro basketball player.
I needed to build a resume.
By the summer of 2008, I was proud of myself. From nothing, I had built a resume. I was more than a one-deal wonder in the professional basketball world. I was a legitimate, bonafide professional basketball player.

I had signed with a new agency headed by a guy named Richard. Rich would be my first agent since the agent who initially got me on in Lithuania.

The first time I contacted Rich, he responded immediately. In the overseas world, agents get contacted by players all the time; many of those players aren’t pro material. In Rich’s eyes, I reasoned, I wasn’t some bum player hoping to play overseas, I was actually doing it. He could see that himself, and name-dropped several places that might be interested in a player of my caliber.

Rich had a lot of clients, 100 or so players, and 85% of them had signed contracts. Rich also had 10 other basketball agents who worked under the umbrella of his company.

I was now in my best possible position. All I’d have to do now was work on my game all summer and wait for Rich to present me 3 or 4 contract offers to choose from.
The phone never rang.
I don’t know exactly why.
Maybe it was just bad luck.
Maybe Rich never put my name in any conversations with teams.
Maybe teams looked at Rich’s client roster and no one was impressed by my body of work to that point.
Regardless of what it was, I woke up one day in September still jobless since Montenegro.
I was able to leverage connections and make a new opportunity for myself, but this experience led me to ask myself some critical questions.

What if this happens again?
What if I can’t make a next deal — and a next deal after that — what happens then?
Where will I be if the rest of my career goes like this, having no control or say over my situation and having to deal with so much uncertainty?
The answers weren’t good.

While I continued to play basketball and pursue playing opportunities for myself, I knew it was time for me to get some control over my life. Which, to me, meant becoming an owner and calling shots, instead of waiting for calls.


I didn’t start out trying to “build a brand”.
In 2005 when I published my first blog post, no one was using the phrase build a brand — at least not when referring to individuals. Back then, a blogger was an unshaven bum in a dirty shirt living in his mom’s basement who hadn’t yet grasped the reality of needing a “real job.”

When I posted my first YouTube video in 2006, YouTube was a place for videos of house cats chasing laser-pointer dots up the walls. There were no ads to profit off your videos.

I flooded YouTube with videos not to become famous, but because it was easy for me to do. Google bought the company and introduced advertising in 2009. YouTube ad revenue was pretty good from 2010-2013, except that —

YouTube was talking half the money off the top, and it wasn’t a negotiation.
More creators coming in meant more hands grabbing for the same pie.
I couldn’t be an owner by just making YouTube videos.
If YouTube changed their algorithms (which they did do several times), it would throw off whatever had been happening, views and subscriber-wise, for many creators including myself.
I understood that one email subscriber was worth at least 20 YouTube subscribers (or Instagram followers or Facebook likes).

I became an entrepreneur because I had so many videos on YouTube that basketball players needed my help making sense of where to begin and what to do with all my content. Someone asked me to organize the stuff into a program.
I did, for $4.99.
By 2012, my prediction from 2009 had come to life: DreAllDay the website and YouTube guy was bigger than Dre Baldwin the basketball player.
Which was fine by me.
On the basketball court, I was one of many players, and it was up to the judgement of some coach, agent or scout as to who was better than whom. I could be hired and fired at the discretion of another person. I had neither power nor control.
Off the court, on my website or while creating content and products, I was in charge.

I could set my own prices, choose my clients and customers, and say what I wanted without fear of retribution from a boss. I had a list — direct contact information (emails, phone numbers, addresses) of people who were interested in me and what I had to offer. Try getting that info from Instagram about your followers.

One day in maybe 2010, I was doing a photoshoot in Midtown Miami. The photographer told me that he looked at photography as a passion rather than a business, and while photography was his full time profession, he only took on projects and did shoots that excited him.
He lamented that this mentality had “kept [him] poor,” because he never took on work for the sake of the check.
Well, then, I asked him, why did he decide to do this shoot with me?
“Because,” he said, “when I looked at your website and your stuff online, I was excited by a person who took an idea out of your head, and make it into something real.”
He was right.

Read about how I leveraged that brand into a business in more ways than one in my next book Work On Your Game: Using The Pro Athlete Mindset To Dominate In Sports, Business and Life. Preorder it now and I’ve got bonuses for you.


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