RIDEOUT: The Other Side of Hard

Ken Rideout
  • 5.0 (33)
  • SELF-IMPROVEMENT
  • UPDATED WEEKLY

The Other Side of Hard, hosted by Ken Rideout — raw, gripping conversations with people who've pushed past the breaking point. Stories of resilience, redemption, and what's waiting on the other side.

  1. 21H AGO

    AI, Politics, and a Shot at the White House | Andrew Yang

    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/ For more information about Noble Mobile, and to get started for just $10 your first month, head to https://noblemobile.com/rideout 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

    1h 13m

  2. 2D AGO

    The Other Side of Hard | Ken Rideout

    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

    2h 29m

  3. MAR 6

    Cocaine, Cancel Culture, and 300 Miles in the Desert | Eli Wehbe

    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

    1h 20m

  4. MAR 4

    From Prison Yard to Venture Fund | Daniel Dart

    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

    1h 40m

  5. FEB 27

    From 35 Years to Freedom | Johnny Bartolomeo

    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 some of America’s toughest federal prisons. From Con Air transfers and Leavenworth politics to solitary confinement, COVID lockdowns, paranoia, marriage behind bars, and suicidal thoughts — he shares what it actually takes to survive that long. But this isn’t just a prison story. It’s about what happens when the rage burns out. When the ego collapses. When a man decides to change. Today, Johnny works in recovery, advocates for second chances, and lives by a simple mantra that carried him through 10,000 days inside: “Just hold on for one more day.” Subscribe / listen on all platforms: https://lnk.to/the-other-side-of-hard  Thank you to our sponsors Ketone-IQ: ⁠ketone.com/rideout Code “RIDEOUT” Rho Nutrition: https://rhonutrition.com Code "RIDEOUT" Chapters (00:00) Welcome and Redemption (01:24) Surviving COVID Lockdown (06:29) From East Boston to Hell's Angels (10:22) How He Joined the Club (15:54) The Killing and Manhunt (22:43) Caught by the Feds (25:39) The 35 Year Plea Deal (31:51) No Bail and Pretrial Jail (36:57) Sentencing Speech and Transfers (41:39) Con Air to Leavenworth (42:11) Shackles and Black Box (43:09) Bathroom Break Reality (44:10) Con Air Rules and Marshals (45:07) Panic Attacks in Transit (46:55) Oklahoma City Transfer Shock (49:38) Leavenworth Boston Crew (50:19) Prison Racial Politics (55:08) Leavenworth Daily Tension (56:21) Chow Hall Table Standoff (01:03:23) From Leavenworth to Lows (01:05:53) Cell Move Threat Backfires (01:08:08) Beating the DHO Case (01:10:06) Prison Love and Marriage (01:14:36) Email Kiosks and Furlough Talk (01:15:54) Inmate Van Walkout (01:18:01) Rapport Over Rules (01:18:31) Transfer Furlough Explained (01:20:57) Wife Pickup And Freedom (01:22:29) Paranoia And Prison Politics (01:26:54) Hotel Visits And SHU (01:30:23) First Step Act Breakthrough (01:34:10) Drug Program And Staff Allies (01:39:45) Release And Reentry Support (01:42:04) 27 Straight Brand Origin (01:43:25) Bean Shooter And Social Media (01:45:07) Covering Club Tattoos (01:46:05) Final Message Learn more about your ad choices. Visit megaphone.fm/adchoices

    1h 51m

  6. FEB 25

    Dirty Feet and a Battered Back | Nick Bare

    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, surviving Ranger School, nearly running out of cash in the early years, stepping down as CEO from burnout, and eventually coming back to lead with more clarity and humility. We get into Leadville breaking him, the marathon that felt effortless, and why he believes most people sabotage themselves by “majoring in the minors.” But the real shift came when achievement stopped delivering peace — and faith reframed how he sees success, marriage, fatherhood, and leadership. At its core, this conversation is about overcoming ego, pressure, and the constant pull of “what’s next.” It’s about becoming the kind of person who doesn’t negotiate when things get hard. Subscribe / listen on all platforms: https://lnk.to/the-other-side-of-hard  Thank you to our sponsors Ketone-IQ: ⁠ketone.com/rideout Code “RIDEOUT” Athletic Brewing: https://athleticbrewing.com Code "RIDEOUT" Rho Nutrition: https://rhonutrition.com Code "RIDEOUT" Chapters (00:00) Hybrid Athlete Praise (00:58) Curiosity Driven Training (02:33) Accountability Pressure (04:49) Discipline Over Motivation (09:34) Responsibilities Over Routine (12:20) BPN Origins and Drive (13:18) Childhood and Work Ethic (15:47) Anorexia and Recovery (20:36) College Hustle Supplements (23:53) Army Service and YouTube (26:23) Bootstrapping and Passion (31:33) Ranger School Reality (34:50) South Korea Business Scale (39:50) Cashflow and Creativity (43:40) Customer Impact and Mission (46:00) Hometown Mockery Story (47:26) Doubt and Mission (48:58) Mindset Before the Race (52:33) Ego Anxiety and Control (58:06) Major in the Majors (01:01:28) Obsessing Over Prep (01:05:32) Hardest Challenges Ranked (01:08:43) Marathon Magic Moments (01:11:50) Faith Transformation Story (01:22:35) BPN CEO Lessons (01:30:30) BPN Starter Supplements (01:33:43) Wrap Up and Subscribe Learn more about your ad choices. Visit megaphone.fm/adchoices

    1h 35m

  7. FEB 20

    From 354 Pounds to Chasing 100 Miles | Dan LaMorte

    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 out his elbow, ballooning in weight, and the moment two car crashes and a fatty liver diagnosis forced him to change everything. He shares how running replaced drugs, how obsession can be both a curse and a superpower, and what it was like to collapse at mile 60 of a 100-mile race with chest and jaw pain — later waking up in the ICU. We also talk about relapse, divorce, grief, rebuilding after public backlash, and why he’s now moving to Leadville to chase one of the hardest races in the world. This episode isn’t about perfect discipline. It’s about resilience, identity, and what happens when you refuse to quit — even when life keeps knocking you down. Subscribe / listen on all platforms: https://lnk.to/the-other-side-of-hard  Thank you to our sponsors Ketone-IQ: ⁠ketone.com/rideout Code “RIDEOUT” Rho Nutrition: https://rhonutrition.com/ Code "RIDEOUT" Athletic Brewing: ⁠https://athleticbrewing.com/ Code "RIDEOUT" Chapters (00:00) Meet Dan LaMorte: Autism, comedy, and finding community (00:44) Instagram connections and protecting your time (05:32) Jersey upbringing, baseball, and tough-love parenting (08:56) 5AM lifts, Asperger’s, and obsessive drive (13:03) College baseball, weed bust, and Tommy John surgery (18:04) Standup as survival: injury to open mics (23:28) Comedy Cellar pressure and weight gain spiral (28:13) Life at 350 pounds: shame and daily reality (31:53) Turning point: car wrecks, fatty liver, LA hikes (35:40) Running, diet shifts, and long-term health (39:43) Ultra lessons, relapse cycles, chest pain scare (41:58) When easy pace feels off: early warning signs (43:13) Mile 40 red flags: chest and jaw pain (44:06) ER diagnosis: spontaneous pneumomediastinum (45:30) ICU aftermath and rhabdo recovery (45:59) Reframing setbacks: resilience and self-talk (50:05) 100-mile obsession and using quitting as fuel (51:35) Health scares, Europe trip, drinking relapse (53:57) Back to training and favorite mountain ultras (55:21) Trail fall, broken fibula, elevator blackout (59:00) Third hospital visit and divorce tension (01:02:24) Wife leaves, grandfather dies: grief and perspective (01:05:14) Viral heckler clip, backlash, relationship strain (01:09:17) Touring dreams, sudden loss, anger and gratitude (01:12:29) Chicago to LA alone: heartbreak and overtraining (01:15:21) Final month with Grandpa: support and momentum (01:18:34) Leadville lottery, altitude prep, crew questions (01:19:52) Family cabin signs and getting into Leadville (01:20:50) Post-divorce reset: renting in Leadville (01:23:07) Fueling long ultras: gels, Tailwind, Ketone IQ (01:23:58) Comedy vs ultra culture: ego and community (01:30:10) Online hate, Strava pressure, public triggers (01:37:23) Training consistency, injury reality, show-up mindset (01:41:49) Fixing the foot: insoles, lifting, calf work (01:48:08) Mishka, memoir writing, and wrap-up Learn more about your ad choices. Visit megaphone.fm/adchoices

    1h 57m

  8. FEB 18

    From Public Failure to World Record | Truett Hanes

    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 about learning humility the hard way, taking the hit, and choosing to return to the work instead of protecting his image. We also get into the stuff that reveals who he is when nobody’s clapping: why he runs races in jeans, how he’s used that attention to support a mission bigger than himself, and how he tries to respond to hate without becoming the same thing he’s fighting. Then we zoom out. The real thread running through all of it is simple: Truett is obsessed with one question: “What am I actually capable of if I stop negotiating with myself?” That question is taking him into the deep end of marathon training, and it’s the same question that’s shaped his whole life: discipline, faith, restraint, and a willingness to be the underdog as long as it takes. Subscribe / listen on all platforms: https://lnk.to/the-other-side-of-hard  Thank you to our sponsors Ketone-IQ: ⁠https://ketone.com/rideout Code “RIDEOUT” Rho Nutrition: https://rhonutrition.com Code "RIDEOUT" Athletic Nicotine: ⁠ https://athleticnicotine.com/rideout Code "RIDEOUT" Chapters (00:00) Welcome Truett Hanes (01:36) Running in Jeans for Charity: The Miracle Foundation Story (04:18) Host Comeback: Sobriety, Triathlons & Marathon Lessons (09:08) Handling Online Hate: Turning Criticism into Fuel (12:58) Redemption: From Pull-Up Failure to World Record (16:48) Olympic Trials Mindset: Volume, Consistency & Tuning Out Noise (18:50) Truett’s Start: Forced Running, Marathon at 13 & Burnout (21:09) Parenting & Pressure: Letting Kids Choose Their Path (27:56) A Father’s Shadow: From Local Fame to Rogan (30:28) Sponsors & Sacrifice: Chasing Big Marathon Goals (34:50) The Underdog Edge: Winning Without Feeling Fulfilled (36:54) When Winning Isn’t Enough: Identity & Presence at Home (37:57) The 1:06 Half: Utah Breakthrough & First Major Win (39:33) Big Wins & Malibu Drama with an Olympic-Level Rival (42:41) Competitive Fire: Aggression, Insecurity & Race-Day Mindset (46:04) Olympic Trials Debate: Doubters, Coaching & Proving 2:29 (50:02) Training Levers: Weight, Marathons, Diet & Sleep (52:39) Data vs Instinct: When Metrics Help—or Hurt (54:17) Race Blow-Ups: Berlin Crash, CIM Stomach Issues & Fueling Lessons (59:18) Gear & Recovery: Heat, Sauna, Cold Plunge & Wearables (01:03:28) NY Masters Win, Boston Regrets & Marathon Chaos (01:05:39) Final Message: Pull-Ups, Patience & Gratitude Learn more about your ad choices. Visit megaphone.fm/adchoices

    1h 10m
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The Other Side of Hard, hosted by Ken Rideout — raw, gripping conversations with people who've pushed past the breaking point. Stories of resilience, redemption, and what's waiting on the other side.

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