RIDEOUT: The Other Side of Hard

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From a Prison Cell to Nike Brand Director | Jordan Rogers

September 11, 2026

Jordan Rogers was using heroin at 15. By the time he landed in county jail, he weighed 116 pounds. His parents had spent his college fund on rehab, and he was facing the possibility of 20 years in prison. I know what it’s like to organize your entire life around getting high. There was a lot in this conversation that hit home for me.  We get into his 396 days locked up, what finally changed when he stopped trying to outsmart every rule, and what happened when he read his mother’s accoun...

From Compulsive Gambler to a $465 Million Exit | Rich Galgano

September 09, 2026

Rich Galgano came back from Vegas so broke that a friend had to pay to get his car out of the airport parking lot. He swore he was done gambling. Then he got home, found $500, and went straight back to another casino. I know what it’s like to promise yourself you’re finished and then do the same shit again.  This week, I sat down with Rich to talk about the gambling addiction that was taking over his life, the three-day bender that finally made him ask for help, and walking into Gambler...

19 Million Followers, Losing Everything, and Starting Over in Nashville | Tayler Holder

September 04, 2026

Tayler Holder has 19 million followers on TikTok, millions more across social media, and a story that goes way beyond being an internet star. Tayler grew up in tiny Alvarado, Texas, racing dirt bikes and chasing adrenaline from the time he was a kid.  He left traditional high school after ninth grade to train and race motocross, then eventually shifted his focus to Vine, Musical.ly, and social media. He moved to Los Angeles determined to figure it out, literally hanging around the apa...