From Free, To Paid

In Work On Your Game [The Book]
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I’ve always loved performing.

My earliest performances were playing Giles in a second grade play called The Salt In The Sea, and Brutus in Julius Caesar a year later.

Then it was basketball. I wasn’t gonna just retire from performing after ball; I chose public speaking. Maybe I’ll start doing stand up comedy on the side since I could perform even more often with that.

The thing about speaking is, unless you’re putting your own events together or you’re at a volunteer group such as Toastmasters, to get your chances on stage, you have to sell yourself and be chosen.

Someone has to see you, your resume and your proposed material, as worth the time of whomever will be in the audience.

Well, that’s how it starts, at least.

A wise person once told me that there’s only one way to know that you’re good as a professional speaker — and it’s not how many people line up to shake your hand when you step off stage, or how many 5-star ratings you receive via audience “smile sheets.”

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It’s when, after you give a speech, other people from that audience reach out to hire you to give another speech because they liked you so much.

The first time I ever spoke in public as a chosen presenter was in 2015, at a social media-focused event held at Lynn University in Boca Raton, FL. There were four of us speaking that day; I’m not being presumptuous when I say I was the best of the four.

The Boca Chamber of Commerce (someone from there had been in the room at Lynn — actually, it may have been the Boca CoC who put on the event in the first place) called on me to present to their membership twice after that. I accepted once; I turned them down the second time because they didn’t want to compensate more me for the skill that I’d already twice proven.

I applied to present at a marketing conference once and was happy to receive an email informing me that I had been chosen. Problem was, they were not paying their presenters; all they could offer was reimbursement for my flight costs.

I wasn’t very known (read: more incoming than outgoing calls) yet at that point. So I accepted — and killed it on stage. The organizers of the same event called me six months later; the reviews of my presentation had gotten their attention. They asked me to give the opening keynote at the same event the next year.

They paid that time.

I had called a Chicago-based association about speaking at their national conference. No one had called me back after several follow ups, so I considered it a dead lead. But a woman from the association called me months later out of the blue.

She had taken a look at my materials, and asked me if I could do a workshop on personal leadership and professional development at the Seattle conference. They, too, couldn’t pay me — but they’d cover flight and hotel.

I accepted. And killed that one, too.

About 40 minutes into my 2-hour workshop, I had everyone take a 10-minute break. One man in the room who’s been sitting in the back came up to me during the break.

Unbeknownst to me, this man was president at the state level (in the state of Maryland) of this national association. His state Association had a conference coming up, and I’d be the perfect presenter for them. How much did I charge?

They paid.

Someone whom I’d never met called me just before New Years. The person they worked for had seen me at my second appearance at that aforementioned marketing conference, and wanted me to give that same presentation at his event. How much did I charge?

That’s happening this year.


When I started posting workouts daily to YouTube, I had so much content that it was hard for players to make sense of it all. It was all free, and it was all there, but no one knew where or how to begin. Someone asked me if I could write down what I did so other players could follow it.

I said I could — but the time investment required for me to organize my training into a consumable format meant they’d have to pay for the resulting product.

That 1-question Q&A made me an entrepreneur.

I told you about my first exposure camp experience. They don’t pay players to come to those camps — the players pay for the privilege to attend. All with the hope that such an investment will pay off in future opportunities.

I paid for several exposure camps. Some returned my investment many times over; they made up for the several that only cost me money and returned nothing but an experience.


I didn’t write Work On Your Game to make money from the sales of the book.

If you want to make money from a book, you damn sure shouldn’t do a deal with a traditional publisher; any cut they get is money that isn’t going in your pocket. Directly speaking, my self-published books will generate more revenue than this one will.

But the strategy is the same as what I did with speaking, pro basketball, what I did on YouTube, what I do in every interview — even what I do with these emails.

  1. Get my game (expertise, speeches, skills, ideas) together.
  2. Find an audience who will listen to and watch what I have to offer.
  3. Prove that I’m good, even if it costs me money to prove it to you (maintaining an email list, for example, is not free).
  4. My game proven, I get paid on the back end for the front end investment.

Does it always work? No — but the better I am, the more likely it does.

As you can see, having game is about more than skills and performing — it’s the strategy behind your actions. I’ll be sharing how I strategized to build my own brand and business in my new book Work On Your Game: Using The Pro Athlete Mindset To Dominate In Sports, Business and Life coming February 22.

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