Early in the day on Wednesday, February 5th, I got the news that Bill Simmons sold his podcast network, The Ringer, for an undisclosed amount. Now, if you have followed his work and podcast network as closely as I have, you’d know it’s valuable and that Bill Simmons wouldn’t DARE sell it for peanuts. So, I’m going to make the jump and assume he cashed in for a pretty penny.

For me, this means more than just a transaction between a well known media personality and big streaming company. Maybe I’m looking at it through the lens of a fan of Bill Simmons and his journey to this point, but forgive me as I explain my perspective.

Bill Simmons is a former media analyst/personality of the giant sports media network that is ESPN. If you know anything about ESPN, you may have heard the restrictions that swarms around its on air personalities. Bills Simmons was one who, no matter the written or unwritten rules, expressed himself consistently to a point where he found himself in trouble. This led to his departure from the network. However, Simmons did not give up but instead bet on himself and went all in on his own sports network, The Ringer.

Now, those who followed or watched Bill Simmons on TV on this was a knowledgeable guy who knew his sports. Departing from ESPN was not enough to keep us away from him. We tuned in. And with that support and the confidence in himself, Bill Simmons continued to put in the work and deliver us the sports news, stories, commentary, and entertainment we deserved.

Getting directly to the point, to me, this transaction is not just about Bill Simmons cashing in. It’s a great example of what happens when you go all in on yourself when others see little value in you. ESPN let Simmons go for expressing himself. Instead of folding or just going to work for another company, Simmons invested in himself and it has paid off. Spotify gains rich content, and Simmons gets a big W. How about that for a feel good story.

The lesson I learned from this, and hope that you do as well, it’s too bet on yourself no matter what! Even when others give up on you, what you think and do for yourself matters!

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