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  • Writer's pictureJimmy Rex

What do we do with somebody who has paid their debt to society?


It’s a fascinating question. Take, for example, my latest podcast guest, Billy McFarland. Most of you know him from the infamous documentary about the event he tried to throw the Fyre Festival.


He lied to raise over $26 million for the event, did not really know what he was doing, and eventually had to cancel the event. Thousands of people lost money they had paid, hoping to attend the weekend of a lifetime.


If you haven’t seen the documentary, you really should. It might be my favorite documentary on Netflix.  You can also check out the podcast on The Jimmy Rex Show.


As I sat down with Billy, we talked about what went wrong. He also talked about his time in prison. He just got out and served a little over four years. But my question today is this, “what do we do with somebody after they’ve paid their debt to society and served their time?”


It’s clear that Billy knows how to market and do a lot of things right. It’s also clear that you’re going to have a hard time trusting this guy ever again.  Most of us know somebody in our own lives that’s gone to jail or prison and since been released. I’ve interviewed several of these people on my podcast to try to learn from their mistakes.


One of the most humbling experiences I’ve ever had was going to Pelican Bay prison and spending time with the inmates mentoring them with a group of entrepreneurs.  “How many of us have committed a felony?” That question was asked to us entrepreneurs when we were there visiting.


We were doing an exercise where you step up to the line if whatever they say relates to you. Only one entrepreneur stepped to the line when asked that question. Upset, the lady leading the exercise asked it again, and she said,  “ I didn’t ask if you got caught for a felony, I asked if you ever committed one.”


She went onto explain that if you’ve ever been in a fight, you’ve committed a felony. Pretty much every one of us entrepreneurs stepped up to the line.


The exercise was meant to get us all thinking, “Are we really that much different than those behind bars?” I won’t go into my own opinion about private prisons in the United States. I think it’s a tragedy what we’ve done to people by locking them up.


For now,



I guess the question I want to ask is, how should we treat people like Billy once they get out? Obviously with skepticism. But also, how do we help them come back from their mistakes?

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