RIDEOUT: The Other Side of Hard

Former NFL wide receiver Eric Decker had everything most people chase—success, fame, a Super Bowl appearance, and a picture-perfect life on the outside. But when football ended, so did the structure, identity, and validation he had relied on his entire life. In this conversation, Eric opens up about what really happens after the dream is over—struggling with confidence, anxiety, and purpose, and c...

Kaitlyn Bristowe went from a small town in Canada to the center of reality TV—and paid the price for it. She opens up about chasing a dance career, hitting rock bottom after a breakup, and rebuilding her life from nothing. Then came The Bachelor and The Bachelorette—and with it, fame, manipulation behind the scenes, and a level of public backlash that nearly broke her. She talks about being slut-s...

Phillip Frankland Lee went from washing dishes to building one of the most unique restaurant empires in the world. But it didn’t happen clean. He was betrayed by a business partner who disappeared, leaving him with debt and lawsuits. He got hit with a $15M legal battle from private equity. His restaurants were shut down overnight during COVID. And instead of folding, he doubled down. In this episo...

Sam Parr built one of the most influential media companies of the last decade, but the path there was anything but clean. Before selling The Hustle to HubSpot, Sam was getting arrested, struggling with alcohol abuse, and bouncing between odd jobs- from running a hot dog stand in Nashville to chasing a job at Airbnb that fell apart after a lie caught up to him. This conversation traces the full arc...

Oz Pearlman is one of the most recognized mentalists in the world—but behind the “mind-reading” is something much deeper. In this episode, we go beyond the tricks. We talk about marathon psychology, the obsession it takes to shave minutes off your time, and the mindset required to win—whether it’s on the course, on stage, or in life. Oz opens up about his upbringing, hustling through college, and...

Steve Weatherford: From Super Bowl Champion to Rock Bottom, Addiction, and Redemption Ken sits down with Super Bowl–champion punter Steve Weatherford for a conversation about identity, rejection, addiction, and what happens when success doesn’t fix anything. Steve shares his journey from a driven, insecure kid chasing approval through sports to becoming one of the best in the world—earning a schol...

Tyler Ramsey is a mixed media artist whose work lives somewhere between chaos and clarity—but his story is even more extreme than his art. Before the galleries, collaborations, and global recognition, Tyler was deep in addiction—alcohol, pills, and a lifestyle that nearly destroyed everything. While producing reality TV shows like Survivor and Fear Factor, his life spiraled into a breaking point t...

Bobby Rich went from East London kid to Team GB judoka, winning national titles and chasing the Olympics—only to fall short at the final hurdle. What followed wasn’t a comeback story. It was a complete reinvention. In this episode, Bobby breaks down the brutal transition from dominating as a junior to getting humbled by grown men, the mental toll of missing Beijing 2008, and the decision to walk a...

Tyler Gaffney did everything right. Stanford. NFL. Two Super Bowl rings. The blueprint most people chase. But behind the surface was a different story — injuries, uncertainty, getting cut, starting over, and losing the identity he built his entire life around. We talk about growing up in a tough part of San Diego, the power of environment, and how one decision can change your trajectory. Tyler bre...

Andrew Yang joins me for a conversation about politics, AI, entrepreneurship, and why he believed he had to run for president. We talk about what pushed him from the private sector into national politics, what he learned from meeting former presidents, and why he came away convinced that the people leading the country are not superhuman. Andrew opens up about the reality of running a presidential...

This week I sat down with my editor Mishka for a raw conversation about the release of my memoir, Everything You Want Is on the Other Side of Hard. I open up about the childhood abuse and chaos that shaped me, the years I lost to addiction, and the long road back through sobriety, endurance sports, and rebuilding my life. We talk about opioid addiction, withdrawals, Subutex dependence, and the mom...

In this bonus episode I sit down with Eli Wehbe for a raw conversation about status, addiction, reinvention, and the cost of living for validation. Eli talks about growing up inp Moreno Valley, breaking into Hollywood nightlife, going from door guy to partner at Warwick, and building relationships with celebrities at the height of LA club culture. He also opens up about the partying, the public fa...

Daniel Dart is the founder of Time Again, but before music, before venture capital, before MIT, he was homeless, gang-affiliated, and sentenced to decades in prison on kidnapping and carjacking-related charges. After fighting his case on appeal and earning a reduced sentence, Daniel rebuilt from nothing — working housekeeping jobs, getting sober, and deliberately surrounding himself with “winners....

John “Johnny Bart” Bartolomeo served nearly 27 years of a 35-year federal sentence after tracking down and killing a rival gang member — a decision that would define the next 10,000 days of his life. In this raw and unfiltered conversation, Johnny walks through his upbringing in East Boston, joining the Hells Angels, the violence that led to his arrest, and the reality of serving decades inside so...

Nick Bare has built his life in public. He announces the goal before he’s ready. He signs up for the race that might break him. He puts the business on the line and accepts the pressure that comes with it. This episode isn’t about highlight reels. It’s about what happens when discipline meets doubt. Nick talks about building BPN from a college apartment while serving as an Army infantry officer, s...

Dan LaMorte is a New York City stand-up comedian and ultra runner who has lived more lives by 31 than most people do in a lifetime. He started comedy at 19 after a career-ending college baseball injury. By 23, he was one of the youngest comics ever passed at the Comedy Cellar — and weighed 354 pounds. In this conversation, Dan opens up about growing up on the spectrum, battling addiction, blowing...

Truett Hanes is the kind of athlete who makes people uncomfortable, not because he’s loud, but because he’s willing to commit in public. He says the goal out loud. He posts the work. He shows the misses. And he keeps moving anyway. This episode isn’t about a highlight reel. It’s about the part most people avoid: what happens when you swing big and come up short, in front of everyone. Truett talks...

Zac Clark’s childhood was stable. Good parents. Sports. School. No obvious “reason” for what came next — which is exactly why his story matters. In his mid-20s, Zac had brain surgery. The surgery worked. But he left the hospital with a raging opioid addiction — and it escalated fast. Pills turned into powder. Powder turned into a needle. And eventually, a missing person report, an arrest, and one...

Walker Hayes wasn’t an “overnight success.” He was a songwriter for two decades. A dad of six. Clocking in at Costco at 4AM. Drinking. Burning out. Still writing anyway. In this episode, Walker talks about what it really looked like before “Fancy Like” — the years where bagels felt like a luxury, security felt like a trap, and quitting felt like the responsible move. Then we go to the hardest day...

This week I sit down with Dr. Kristen Holmes — scientist, former elite athlete, coach, and the Global Head of Human Performance at WHOOP. Kristen built her life around performance early. Sports became structure. Discipline became safety. Achievement became identity. But long before the titles and credentials, she was learning how to survive instability, neglect, and trauma — and carrying that nerv...

Bill Shufelt, CEO and co-founder of Athletic Brewing Company, shares the remarkable journey from high-intensity finance to building the world’s leading non-alcoholic beer brand. In this conversation, Ken Rideout and Bill go deep on the real story behind Athletic: Bill’s personal struggle with alcohol, the moment sobriety changed everything, and the “missionary vs. mercenary” mindset that kept him...

Ran Carthon has lived football from every angle — from undrafted NFL running back fighting to stay on rosters, to working his way through scouting and personnel, to eventually becoming General Manager of the Tennessee Titans. In this conversation, Ken Rideout goes beyond wins and losses to explore the human side of the NFL: pressure, family sacrifice, leadership, and what it really takes to earn t...

John Joseph grew up in extreme violence, neglect, and instability. Raised by a violent, alcoholic father, he spent years in abusive foster homes, experienced homelessness on the streets of New York City as a teenager, battled addiction, and cycled through incarceration and institutional lock-ups at a young age. By every conventional measure, his life was headed toward an early end. This episode tr...

This week I sit down with Ian Bick — entrepreneur, storyteller, and podcast host, where he tells real stories of incarceration, redemption, and what change actually costs. Ian became a nightclub owner as a teenager. Fast money. Bigger pressure. Debt. Gambling. Then the bottom fell out — and at 21, he was convicted of federal wire fraud and sent into the federal system. He walks us through what peo...

Mike Lee lived the kind of life that doesn’t end clean. Heroin. Bank robberies. Prison. Overdoses. A revolving door that kept spinning until it didn’t. In this episode, Mike breaks down the real mechanics of addiction — the daily grind of staying high, staying ahead, and eventually getting cornered. He talks about methadone, getting followed, getting grabbed, and finally deciding to make a change....