RIDEOUT: The Other Side of Hard

Ken Rideout
  • 5.0 (37)
  • 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. 2H AGO

    Drunk and Directionless to Building an Empire | Sam Parr

    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. From Division I track athlete to dropout. From drunk and directionless to building a media empire. From rock bottom to getting sober through a San Francisco clinic that changed his life. We get into: The real math behind building and selling The Hustle Why owning an email list beats chasing algorithms The psychology of fear, networking, and taking swings How Hampton became a $15K/year network for elite founders What addiction actually looked like — and how he got out This is a story about obsession, proximity, risk, and rebuilding — not just once, but multiple times. Thank you to our sponsors Ketone-IQ: ⁠ketone.com/rideout Code “RIDEOUT” Timeline: timeline.com/rideout Code "RIDEOUT" Ken’s book now available here: https://www.theothersideofhard.com/ Chapters (00:00) Money Talk Icebreaker (01:54) Nerding Out and Self Belief (04:06) Track Star Origins (04:53) Pickers and Hot Dog Hustle (06:33) Airbnb Lie and Rock Bottom (08:20) Bunk to HustleCon Breakthrough (09:46) Anti MBA Networking Playbook (12:54) Passion and Being Yourself (15:05) From Events to The Hustle (16:04) Newsletter Math and Scaling (19:08) Exit Numbers and Luck (20:13) Owning the Inbox Insight (23:32) Fear and Fighting Mindset (27:38) Boxing Gym Lessons (30:36) Mitochondria Aging Boost (31:30) Selling The Hustle (32:05) HubSpot Media Model (34:14) Meeting His Wife (37:40) Immigrants And Politics (43:37) Patriotism And Denim (45:01) Building Hampton Network (49:42) Pricing And Peer Value (51:48) Getting Sober Story (54:37) Failures And Parenting Scare (58:25) Maced While Handcuffed (59:05) Son’s Concussion Scare (01:00:37) Bike Crashes and Morphine (01:04:39) Seal Stories and Real Toughness (01:08:01) Regret Not Enlisting (01:09:18) Entrepreneur Advice and Proximity (01:10:41) Networking Without Networking (01:11:48) Cold Email Done Right (01:15:47) Haters and Mean Comments (01:20:02) Writing and Selling the Memoir (01:25:57) Bro Talk and Wrap Up (01:28:21) Subscribe and Book Links Learn more about your ad choices. Visit megaphone.fm/adchoices

    1h 30m

  2. 2D AGO

    Mind Games, Marathons, and Mastery | Oz Pearlman, Mentalist

    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 building a career from nothing—performing magic in restaurants, learning human psychology, and turning rejection into opportunity. He breaks down how he reads people, builds relationships, and creates moments that feel impossible. We also dive into connecting with people the right way, why most people approach it wrong, and how giving value first changes everything. This is a conversation about discipline, obsession, and mastering your craft—whatever it is. 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) Meet Oz Pearlman (00:36) Marathon PR Mindset (03:02) Winning Races Psychology (05:42) Training Slumps Comebacks (08:22) Why Running Feels Good (11:36) Origins Midwest Roots (12:33) School Skips Siblings (15:57) Parenting Chaos (19:06) Abuse Discipline Debate (24:51) Engineering Divorce Magic (26:57) Hustling Paying Tuition (28:32) Money Class Upbringing (29:13) Compare and Despair (29:58) Work Ethic and Values (31:58) Blaine and Street Magic (33:12) Restaurant Magic Lessons (36:00) Learning Tricks and Gimmicks (38:35) Impromptu Superman Mindset (41:30) Mentors and Time Value (43:55) Marathon Mind Games (47:44) College Hustle and Numbers (50:08) Penguin Magic Breakthrough (52:37) Repackaging Mentalism (55:02) Critics and Ethics (57:43) High Stakes Debuts (58:44) Magic Is the Point (59:27) Selling a Success Guide (01:01:21) Handling Haters (01:02:33) When Tricks Fail (01:04:12) Notes and Repeat Clients (01:06:34) Building Real Networks (01:11:33) Lead With Give (01:17:27) Earning Attention (01:18:56) Big Break and White House (01:24:54) Closing and Subscribe Learn more about your ad choices. Visit megaphone.fm/adchoices

    1h 27m

  3. MAR 27

    He Won the Super Bowl… Then Lost Himself | Steve Weatherford

    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

    2h 21m

  4. MAR 25

    Drugs, Destruction, and a Second Life Through Art | Tyler Ramsey

    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

    1h 51m

  5. MAR 20

    Missing the Olympics to Training the Cultural Icons | Bobby Rich

    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

    1h 29m

  6. MAR 18

    Brick by Brick to the NFL and Back Again | Tyler Gaffney

    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

    2h 1m

  7. MAR 13

    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

  8. MAR 11

    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
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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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