• He Won the Super Bowl… Then Lost Himself | Steve Weatherford
    Mar 27 2026
    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 scholarship to Illinois, grinding through the NFL as an undrafted player, getting cut multiple times, and eventually winning a Super Bowl with the New York Giants. But even at the top, with money, recognition, and a $13M contract, he found himself empty and searching for more. He opens up about the parts of his life most people never see: childhood trauma, ADHD and rejection, sexual abuse, and the early roots of addiction. That pain followed him into adulthood—fueling porn addiction, painkiller use, infidelity, and a double life that nearly cost him everything, including his marriage and his life. Steve recounts the brutal reality of getting cut in the NFL, losing his identity, and hitting rock bottom—culminating in isolation, depression, and suicidal thoughts. What followed was a long, uncomfortable process of confronting his past, rebuilding his identity, and redefining what success actually means. This is a conversation about chasing validation, the dark side of achievement, and the realization that winning doesn’t always feel like winning. It’s also about rebuilding—faith, family, fatherhood, and learning to live with purpose instead of proving something. Thank you to our sponsors Ketone-IQ: ⁠ketone.com/rideout Code “RIDEOUT” Rho: https://rhonutrition.com Code "RIDEOUT" Athletic Nicotine: https://www.athleticnicotine.com/ Code "RIDEOUT" Ken’s book now available here: https://www.theothersideofhard.com/ Chapters (00:00) Welcome and Book Launch (00:53) Success Pressure and Presence (02:48) Worthiness and Relationships (06:32) Origin Story Louisiana (07:18) Track Club and Drive (11:43) Soccer to Football Kicker (15:10) Butt Cheek Field Goal Tale (18:34) Never Quit and Gratification (22:06) Illinois and Decathlon Path (28:18) NFL Break In Saints Camp (32:32) Getting Cut Identity Crash (37:02) Street Preacher Turning Point (40:48) Waiver Wire Whiplash (42:22) Rejection and Galatians (43:53) Late Bloomers Mindset (46:27) Trauma and Testimony (50:52) Fatherhood and Identity (53:36) Addiction Roots and ADHD (01:00:18) Power Team Salvation (01:08:44) Grooming and Aftermath (01:17:15) Super Bowl Emptiness (01:26:37) Retirement and Rock Bottom (01:32:13) Back to Church (01:33:49) Pastor Calls Him Out (01:35:51) Last Resort Faith (01:36:12) Desert Mens Retreat (01:39:14) Lightning Bolt Encounter (01:42:40) Releasing Trauma to God (01:44:53) Confession and Coaching (01:47:29) Door Slam Move Texas (01:51:19) Called to Lead Men (01:53:26) Launching Pad Grows (02:00:52) Ken Faith Journey (02:11:39) Grind Versus Grace (02:16:53) Salvation Prayer (02:20:18) Conclusion Learn more about your ad choices. Visit megaphone.fm/adchoices
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    2 hrs and 21 mins
  • Drugs, Destruction, and a Second Life Through Art | Tyler Ramsey
    Mar 25 2026
    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 that led to a jungle disappearance, jail in Africa, and ultimately rehab. What followed wasn’t overnight change. It was years of relapse, rebuilding, and finally a complete reset—faith, service, and nearly five years of sobriety. Today, Tyler is not only a working artist with global collaborations (TOMS, Aviator Nation, Ferrari), but also someone dedicated to recovery, honesty, and purpose through his “Punk Rock Sober” mission. This is a conversation about addiction, identity, creativity, faith, and what it actually takes to rebuild your life from nothing. Thank you to our sponsors Ketone-IQ: ⁠ketone.com/rideout Code “RIDEOUT” Rho: https://rhonutrition.com Code "RIDEOUT" Athletic Brewing: https://athleticbrewing.com Code "RIDEOUT" Ken’s book now available here: https://www.theothersideofhard.com/ Chapters (00:00) Ken’s love of Art (00:33) Spotting Iconic Artists (01:39) Inside This Art Space (04:20) Gallery Snobbery Explained (05:50) Meet Tyler Ramsey (06:53) Growing Up and Family Trauma (11:09) From Screenwriting to Reality TV (13:52) Diddy Set Stories (19:04) Survivor and Fear Factor Era (20:19) Casting Secrets for Reality TV (22:02) Addiction and Drug of Choice (26:42) Survivor Africa Bender (30:38) Runaway Jungle Disaster (34:13) Jail Rescue and Rehab (37:57) Rehab Wake Up Calls (39:15) Cushy vs Bootcamp Rehab (40:25) Faith Journey Begins (43:17) Church and Family Pull (45:53) King David and Forgiveness (50:12) Burning Man Riffs (53:28) Dream Center Rock Bottom (58:24) Five Years Sober (01:00:40) Retreats and Psychedelics (01:06:56) Banksy Mystery Talk (01:10:28) Art Theft and Heat Quote (01:13:22) Wes Watson Debate (01:16:01) Muscle Man Persona (01:16:31) Stuff Versus Fulfillment (01:18:58) Art Over Labels (01:21:42) Favorite Artists Talk (01:26:06) Neon Art Process (01:30:07) Toms Shoes Collab (01:32:46) Aviator Nation Stories (01:39:41) Recovery And Service (01:44:10) Support Creators (01:49:26) Closing Remarks Learn more about your ad choices. Visit megaphone.fm/adchoices
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    1 hr and 51 mins
  • Missing the Olympics to Training the Cultural Icons | Bobby Rich
    Mar 20 2026
    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 away at his peak. He shares why he took an MMA fight on five weeks’ notice, what fighting fear actually feels like, and how mindset—not talent—separates those who last. From training with Roger Gracie to coaching David Haye, working on Guy Ritchie film sets, and building a 15-year partnership with David Beckham, Bobby rebuilt his life brick by brick—without shortcuts. This is a conversation about pressure, identity, discipline, and what happens when the dream doesn’t go your way—and you have to build something better. Thank you to our sponsors Ketone-IQ: ⁠ketone.com/rideout Code “RIDEOUT” Rho: https://rhonutrition.com Code "RIDEOUT" Ken’s book now available here: https://www.theothersideofhard.com/ Chapters (00:00) Welcome and Background (00:21) Kids Competing and Losing (01:13) First Steps in Judo (03:11) Why Judo Over Striking (05:40) Team GB and Senior Reality Check (08:35) Cross Training with Gracie (11:30) Coaches and Mindset Shift (14:05) Turning Point and Big Wins (16:49) Olympic Qualifying Explained (19:21) Missing Beijing and Next Moves (21:02) MMA Fight Challenge (28:44) Fight Nerves and Lessons (30:06) Harnessing Nerves (30:36) Locker Room Pressure (31:49) Confidence Tricks (32:46) When Perfect Backfires (36:11) Sacrifice Behind Success (38:02) Turning Down the Noise (39:56) Marathon Mind Games (42:35) Sponsor Break (43:32) East London Roots (44:13) Third Space and Boxing (48:54) Meeting Guy Ritchie (55:42) Training Stars and Beckham (01:00:54) Elite Speed Genetics (01:01:21) Coaching High Performers (01:02:00) IM8 Partnership Origin (01:05:23) Dr Dawn Spotlight (01:10:27) Health Responsibility Mindset (01:12:25) Parenting and Leading (01:14:21) Wife Training and Pregnancy (01:19:15) Onus Agency and Gym Design (01:21:36) Career Edge and Work Ethic (01:27:29) Closing Remarks Learn more about your ad choices. Visit megaphone.fm/adchoices
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    1 hr and 29 mins
  • Brick by Brick to the NFL and Back Again | Tyler Gaffney
    Mar 18 2026
    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 breaks down the reality of the NFL — the thin margin between making it and losing it — and what it feels like when the game is taken away from you. This is a conversation about discipline, setbacks, family, and what it actually takes to rebuild your life when the thing you worked for disappears. Thank you to our sponsors Ketone-IQ: ⁠ketone.com/rideout Code “RIDEOUT” Rho: https://rhonutrition.com Code "RIDEOUT" Ken’s book now available here: https://www.theothersideofhard.com/ Chapters (00:00) Super Bowl Rings Moment (01:32) Brick by Brick Mindset (02:22) Happiness and Trauma Scale (03:57) San Diego Roots and Family (07:14) School Switch and Friend Groups (11:17) Freshman Football Toughness (14:53) Recruiting Letters and Grind (19:05) Suspended and Chip on Shoulder (25:23) Stanford Camp and D1 Reality (29:03) Harbaugh Era and Organization (33:01) USC Upset Touchdown Story (36:42) Baseball Draft and Leaving Stanford (39:00) Minor League Reality Check (41:06) Returning for Fifth Year (42:33) Winning the Starting Job (43:17) Rose Bowl Side Story (43:48) NFL Dreams and Agents (45:02) Agent Money and Business (48:40) Draft Day Rollercoaster (53:17) Panthers Pick and Opportunity (54:44) NFL Speed and Hazing (58:09) First Play Knee Disaster (01:01:45) Patriots Waiver Surprise (01:06:31) Patriots Culture and Brady (01:15:05) Hernandez Shadow and Comeback (01:16:46) Injuries and Roster Grind (01:21:02) Jaguars Detour and Rings (01:22:15) Reading Offensive Tells (01:23:55) Execution Over Surprise (01:24:38) Patriots Do Your Job (01:25:14) Super Bowl LI Inactive View (01:28:59) Halftime Calm Comeback (01:30:07) Luck Thin Margins (01:32:35) Cut After The Ring (01:33:27) Tryouts Contracts Reality (01:37:32) Meniscus Injury Breaking Point (01:39:58) Minor League Baseball Grind (01:41:47) Identity After Sports (01:43:07) Building A New Career (01:45:58) COVID NFL Return Twist (01:48:39) Knowing When To Quit (01:50:40) Nashville Family Life (01:51:49) Wife Media And Values (01:55:03) Marketing Consulting Mission (01:59:14) Final Thanks Learn more about your ad choices. Visit megaphone.fm/adchoices
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    2 hrs and 1 min
  • AI, Politics, and a Shot at the White House | Andrew Yang
    Mar 13 2026
    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 campaign, from building a team and raising roughly $40 million to making seven debate stages and breaking through with independent media. We also get into the deeper issues driving his campaign: collapsing trust in government, the two-party trap, insider corruption, and the very real threat AI poses to millions of jobs. Andrew explains why he’s been sounding the alarm on automation for years and why he believes the country still has not caught up to what’s coming. From there, we shift into Noble Mobile and the simple idea behind it: most Americans are getting crushed on wireless bills and barely question it. Andrew breaks down how Noble works, why phone service has become an overpriced commodity, and how reducing costs and screen time can both improve people’s lives. This is a conversation about ambition, common sense, broken systems, and trying to build something better instead of just complaining about what’s broken. Thank you to our sponsors Ketone-IQ: ⁠ketone.com/rideout Code “RIDEOUT” Rho: https://rhonutrition.com Code "RIDEOUT" Athletic Brewing: https://athleticbrewing.com Code "RIDEOUT" Ken’s book now available here: https://www.theothersideofhard.com/ Chapters (00:00) Welcome and Book (00:35) Why Run for President (01:02) Meeting Presidents Up Close (05:31) Fame and Being Recognized (06:56) Growing Up With Racism (08:47) Kids Today and Toughness (11:58) Government Accountability Problem (13:40) Congress Approval vs Reelection (15:57) AI Automation and Freedom Dividend (17:44) Two Party Trap and Independents (21:55) Builders for Leadership Mark Cuban (23:21) Noble Mobile Cuts Your Bill (28:32) Phone Addiction and Family Rules (33:00) Why Wireless Is a Commodity (34:25) Tech Change Nostalgia (35:55) Parents Immigration Story (36:15) Immigrant Parents Leap (37:12) American Dream Debate (38:12) Indie Media Breakthrough (39:03) Creator Economy Examples (40:17) Work Guidance And Taxes (42:30) How To Run For President (44:22) Money Consultants And PACs (46:18) Debate Stage Reality (50:43) Union Power And Politics (54:44) Noble Mobile Origin Story (57:24) Cutting Bills And Compounding (01:04:40) Parenting Screens And Safety (01:09:33) Wrap Up Book And Subscribe Learn more about your ad choices. Visit megaphone.fm/adchoices
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    1 hr and 13 mins
  • The Other Side of Hard | Ken Rideout
    Mar 11 2026
    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 moment Vivitrol finally helped me break the cycle. We also dive into the deeper parts of my story — the mentors who changed my life, the pressure of success in finance, marriage and fatherhood, adopting my daughter from Ethiopia, and Shelby’s battle with breast cancer. This episode isn’t a victory lap. It’s an honest look at trauma, fear, discipline, and the work it takes to keep moving forward. Because the truth is simple: Everything You Want is on the Other Side of Hard. Get the book here: https://www.theothersideofhard.com/ Thank you to our sponsors Ketone-IQ: ⁠ketone.com/rideout Code “RIDEOUT” Rho: https://rhonutrition.com Code "RIDEOUT" Athletic Brewing: https://athleticbrewing.com Code "RIDEOUT" Chapters (00:00) Book Launch Jitters (02:08) Family Fallout Update (03:32) Brothers And Chaos (07:29) Parenting And Ambition (12:36) Angels And Fear Lessons (15:08) College Fights And Coke (19:11) Dream Dies New Direction (21:48) NYC Hustle And Vertical Club (26:41) Opioids And The Last Time Loop (28:03) Withdrawal And Getting Sober (35:59) London Glamour Mom Money (36:56) Loans And Survival Mode (37:35) Writing About Mom (38:44) Toning Down The Book (39:45) London Drugs And Leadership (42:25) Porsche Paranoia (43:11) Shelby Style Stories (45:24) Tom Browne Fashion Era (48:50) Friendship Across Differences (50:07) Subutex Vicious Cycle (53:33) Vivitrol Way Out (55:23) Finance Crash And Bonuses (59:43) Job Loss And Reinvention (01:05:58) Adoption And Getting Clean (01:08:52) Running Through Emotions (01:11:36) Crisis Mode First Responder (01:14:38) Bike Crash Aftermath (01:15:51) Boxing As Life Metaphor (01:20:19) Owning Failure And Quitting (01:23:44) No Finish Line Mindset (01:27:15) Shelby Cancer Update (01:28:28) Win Or Die Trying (01:33:00) Escape From New York (01:35:44) Transracial Adoption Talk (01:41:01) Community In Nashville (01:46:08) Race Strategy Not Cheating (01:50:24) Neve at Start Line (01:53:52) Calf Injury Breakthrough (01:56:59) Masters Title Surprise (01:58:17) Onsite Therapy Reset (02:01:59) Roommates and Brotherhood (02:06:06) Rich Roll Connection (02:10:30) Gobi Prep and Gear (02:11:50) London Championship Twist (02:19:57) Running Beyond Identity (02:22:21) Life Lessons and Farewell Learn more about your ad choices. Visit megaphone.fm/adchoices
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    2 hrs and 29 mins
  • Cocaine, Cancel Culture, and 300 Miles in the Desert | Eli Wehbe
    Mar 6 2026
    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 fallout that blew up his life, and the decision to disappear from social media and rebuild from scratch. What started as a reset turned into a full obsession: marathons, trail racing, 100-milers, Moab 240, and now a real shot at podiuming Arizona Monster 300. Ken and Eli get into sleep deprivation, fueling, sponsorships, social media, and the mindset it takes to compete in races most people can’t even imagine finishing. This is a conversation about image versus reality, losing the identity you built, and finding something real on the other side of pain. Thank you to our sponsors Ketone-IQ: ⁠ketone.com/rideout Code “RIDEOUT” Rho: https://rhonutrition.com Code "RIDEOUT" Athletic Nicotine: https://athleticnicotine.com/rideout Code "RIDEOUT" Chapters (00:00) Meet Eli (01:24) From Moreno Valley to LA (02:24) Breaking Into Nightlife (03:19) Building a Celebrity Rolodex (04:48) Playhouse and the Golden Era (05:41) Mike Posner and Reinvention (07:41) Coke and Party Culture (10:36) Overdose Lawsuit Fallout (12:20) Cancel Culture and Going Dark (14:31) Running as a Reset (17:04) GHB Explained and Narrative Spin (20:36) Cops, Phone Search, and Lessons (25:25) Case Outcome and Drug Dangers (27:31) First Trail Run Disaster (29:49) Water Bubbler Close Call (31:15) Mountain Lion Encounter (32:47) From 50K to 300 Miles (35:57) Sleep Strategy Midrace (38:11) Winning Mindset No Balance (39:56) Injury DNF Redemption (40:50) Stage Racing With Packs (43:49) Podium Goals And Coaching (45:12) Fueling Ketones Aid Stations (48:34) Shoes Sponsors Speed Project (51:49) Recovery Age And New Book (53:43) Book Copy Surprise (54:58) Online Persona vs Reality (56:02) Relentless Outreach Mindset (56:37) Andy Frisella Connection (58:29) Cam Haynes and Goggins Reel (01:02:59) Moab Finish Line Moment (01:04:17) Validation and Winning Mindset (01:08:31) Race Calendar and Leadville Plans (01:10:00) Altitude Pain and 100 Mile Lessons (01:13:48) Sponsors and Runner Branding (01:16:31) Wrap Up and Where to Follow Learn more about your ad choices. Visit megaphone.fm/adchoices
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    1 hr and 20 mins
  • From Prison Yard to Venture Fund | Daniel Dart
    Mar 4 2026
    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.” That path led him into international development, work connected to the World Bank and the Bezos Family Foundation, two master’s degrees at the London School of Economics (without traditional prerequisites), and an MBA at MIT. Today he runs Rock Yard Ventures, invests in critical and foundational industries, and is pursuing a California governor’s pardon. This is a conversation about prison politics, systemic failure, stigma, merit, second chances, and what it actually takes to rebuild a life from the ground up. Thank you to our sponsors Ketone-IQ: ⁠ketone.com/rideout Code “RIDEOUT” Athletic Brewing: https://athleticbrewing.com Code "RIDEOUT" Athletic Nicotine: https://athleticnicotine.com/rideout Code "RIDEOUT" Chapters (00:00) Meet Daniel Dart (01:37) From Homelessness to Drive (02:50) Family Chaos and Placements (04:10) System Failures and Resentment (05:52) Life on the Streets (11:01) Gangs and Prison Reality (14:18) Finding Music and Purpose (17:45) Violence Risk and Prison Code (24:23) Charges Plea and Appeals (31:14) First Day Prison and Transfers (33:10) White Gangs Breakdown (33:20) Arizona Hunger Strike (34:37) Shackled Prison Transport (35:36) Cops as Gangs (36:11) Fighting the Appeal (39:51) Judge Offers Two Options (42:48) Release and Low Yard Life (47:29) Guard Stories and Violence (52:49) Sponsor Break Athletic Nicotine (53:44) Rebuilding After Prison (56:33) From Music to Policy (58:15) World Bank Mentors and LSE (59:08) Bezos Foundation Break (01:02:48) Two Masters at LSE (01:03:37) Saudi Merit Over Stigma (01:07:02) Stigma Hits Banking (01:08:24) Banking Stigma Fallout (01:09:33) From LSE to MIT MBA (01:12:57) Allies Who Changed Everything (01:15:02) Building Prison Reentry Program (01:17:27) Launching Rock Yard Fund (01:19:58) Imposter Syndrome to Conviction (01:22:58) Fundraising and Lead Investor Mindset (01:27:15) Missionary Founders and Long Game (01:28:53) Fund Strategy and Sticky Industries (01:38:04) Pardon Update and Final Wrap Learn more about your ad choices. Visit megaphone.fm/adchoices
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    1 hr and 40 mins