RIDEOUT: The Other Side of Hard

Ken Rideout
  • 5.0 (44)
  • 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. 4d ago

    Jump Around. Crash Hard. | Danny Boy O'Connor

    Danny Boy O'Connor helped build one of the biggest songs of the 1990s. As a founding member of House of Pain, he watched "Jump Around" become a global anthem and experienced everything that came with it: money, fame, chaos, addiction, and eventually rock bottom. In this conversation, Danny shares stories from a childhood shaped by violence, crime, and survival. We talk about the rise of House of Pain, getting kicked off the Beastie Boys tour, sudden success, reckless spending, meth addiction, relapse, and the long road to recovery. But this isn't just a story about music. It's a story about redemption. After getting sober, Danny found a new purpose preserving The Outsiders House in Tulsa, turning a forgotten movie location into a museum that now inspires people from around the world. This is a conversation about identity, recovery, second chances, and what happens when you finally find a mission bigger than yourself. Thank you to our sponsors Ketone-IQ: ⁠ketone.com/rideout Code “RIDEOUT” Rho Nutrition: https://rhonutrition.com/ Code "RIDEOUT" Ken’s book now available here: https://www.theothersideofhard.com/ Chapters (00:00) OGs Reunion Intro (00:18) Boston UFC Night (02:09) Dana White Loyalty (02:55) Boston vs New York (05:52) Discretion in Fame (07:02) Hard Childhood Origins (09:03) Moving and Culture Shock (12:56) Ketone IQ Ad Break (13:59) Outsiders and Toughness (16:38) Sobriety Reality Check (17:44) Skipping School and Sports (19:09) Music and Kiss Dreams (20:27) Latchkey and Outsiders (22:16) Leaving Home Early (23:05) Credit Card Hustles (27:34) Gang Life and Charges (29:18) Kids Today Drink Less (30:07) Teen Drinking Fades (30:43) Street Life Origins (31:34) Hip Hop Identity (33:05) Cholo Style Valley Gangs (34:12) Everlast Demo Moment (42:19) House Of Pain Forms (45:01) Label Bids Tommy Boy (47:42) Money Fame Whiplash (47:56) Mickey Rourke Boxing Bond (52:53) Fame Panic And Payola (57:25) When Jump Around Faded (57:57) Hit Song Whiplash (58:28) Twilight Zone Success (59:28) Money Fame Temptations (59:54) Second Album Pressure (01:01:17) Beastie Boys Tour Blowup (01:02:57) Weedwear Hustle Origins (01:04:20) Beastie Boys Changed Hip Hop (01:06:18) Kicked Off Tour Fallout (01:07:57) Spending Spree Reality (01:09:45) House of Pain Breakup (01:10:21) Outlaw Biker Life (01:12:32) Haze Art Stories (01:14:37) Meth Addiction Spiral (01:20:03) First Meth Hit Malibu (01:22:00) Rock Bottom And Regret (01:24:30) Finding AA Community (01:25:59) Commitment One Day (01:26:53) Thirty Day Chip Moment (01:27:55) Trusted With Service (01:28:51) Leading And Sharing (01:29:24) Success Then Drift (01:30:26) Relapse Spiral (01:32:16) Rock Bottom Wake Up (01:34:01) New Surrender New Life (01:36:19) Prison Service Lessons (01:39:25) Outsiders Epiphany (01:42:13) Delta Bravo Origins (01:43:56) Buying The House (01:46:48) Community Builds Museum (01:49:27) S E Hinton And Fans (01:53:25) Museum Today Tulsa Love (01:58:16) Closing Thanks And Plugs Learn more about your ad choices. Visit megaphone.fm/adchoices

    2 hr

  2. 6d ago

    Addicted at 15. NFL Star at 30. | Darren Waller

    Darren Waller was one of the most talented players in football.Georgia Tech standout. NFL draft pick. Pro Bowl tight end. Massive contracts. Fame. Success. But behind the scenes, he was spiraling. Addiction started at 15. Pills. Alcohol. Failed drug tests. Suspensions. A fentanyl overdose that nearly killed him. Eventually, the NFL banned him for a year. This conversation goes way deeper than football. We talk about identity, addiction, recovery, fame, relationships, loneliness, rebuilding your life from scratch, and what happens when you finally stop running from yourself. Darren opens up about rehab, working at Sprouts after losing football, fighting his way back to the NFL, signing life-changing contracts, his marriage and divorce, retiring from the game, and finding purpose through sobriety, music, and helping others recover. One of the most honest conversations we’ve had. Thank you to our sponsors Ketone-IQ: ⁠ketone.com/rideout Code “RIDEOUT” Wild Roman: wildroman.com/rideout Code “RIDEOUT15” Rho Nutrition: https://rhonutrition.com/ Code "RIDEOUT" Ken’s book now available here: https://www.theothersideofhard.com/ Chapters (00:00) Darren Waller Joins (00:29) Music Roots and Passion (01:56) Atlanta Upbringing and Academics (04:58) Georgia Tech Grind (06:25) Position Switch and NFL Dreams (08:50) High School Arrest and Fallout (13:42) Addiction Begins (15:59) Identity and Belonging (20:51) College Partying and Arrest (24:42) Scouts Notice and Draft Path (31:16) Agents Combine and 40 Time (33:15) Drafted by Ravens (33:58) Combine Lies and Red Flags (35:24) NFL Money and Pill Supply (38:36) Rookie Camp and Injury Spiral (40:05) Switch to Tight End (40:28) Failed Tests and Suspension (43:15) Touchdowns and Shoulder Tear (46:33) Banned and Fentanyl Overdose (50:32) Detox and Rehab Breakthrough (51:40) Sprouts Job and Rebuilding (54:22) Training for Comeback (57:17) Raiders Chance and Breakout (01:00:04) Sobriety and Self Belief (01:03:40) NAD Plus Sponsor Break (01:04:44) Big Contract Setup (01:05:17) First Big Extension (01:06:54) Handling Fame and Money (01:07:37) Frugal Lifestyle Choices (01:09:53) Giving Back Through Foundation (01:10:50) Love Addiction and Marriage (01:16:01) Giants Trade and Retirement (01:21:20) Year Off and Self Work (01:23:02) Unretiring With Dolphins (01:27:15) Injury Comeback and Free Agency (01:29:19) Books Music and Wrap Up Learn more about your ad choices. Visit megaphone.fm/adchoices

    1h 33m

  3. May 22

    The World’s Strongest Man | Mitchell Hooper

    Mitchell Hooper became the strongest man on Earth almost by accident. A former marathon runner, exercise physiologist, and coach… he found Strongman late, exploded onto the scene, and became World’s Strongest Man in just a few years. But this conversation goes way deeper than strength. We talk about steroids, the Enhanced Games, performance obsession, money, success, mental health, addiction, suicide attempts, psychedelics, fatherhood, and faith. Mitchell opens up about the pressure of winning, the emptiness that can come with achievement, and the internal battles most people never see behind the titles. This is one of the most honest conversations we’ve had about masculinity, suffering, and what actually gives life meaning. Thank you to our sponsors 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" Ken’s book now available here: https://www.theothersideofhard.com/ Chapters (00:00) Meet Mitchell Hooper (00:28) Hybrid Strength Challenge (01:33) Early Lifting Origins (04:09) Family And Athletic Roots (06:33) Imposter Syndrome And Winning (08:36) Success Money And Meaning (13:53) Strongman Culture And Rivalries (15:08) PED Reality In Strongman (18:01) Healthspan Hormones And Society (24:13) Starting Steroids And Gains (30:56) Marathon Days And Pacing Pain (32:52) Enhanced Games And Exercise Medicine (35:36) Cardio Versus Lifting (37:00) Avoiding The Middle Zone (38:07) Reps Sets And Intensity (39:52) Grip Strength And Carries (41:49) Progress Over Aesthetics (43:02) Body Dysmorphia Trap (44:30) Winning Feels Different (47:18) Family And Fertility (50:57) Strongman Bulking Diet (53:28) Deadlift Prep And Cues (58:55) Painkillers And Injuries (01:02:43) Discipline Builds Identity (01:06:32) Mental Health And Guilt (01:09:06) Running As Recovery (01:10:22) Fighting for Family (01:11:49) Therapy and Integration (01:13:12) Faith and Gratitude (01:15:52) Ibogaine and Addiction (01:18:27) DMT and Facing Death (01:21:36) Marriage and Showing Up (01:24:35) Addiction Story in Finance (01:26:57) ADHD Meds Reality Check (01:28:27) Enhanced Games Prep (01:29:15) Thor Rivalry and Attempts (01:32:37) Prize Money and Sponsors (01:35:48) Wife Backstage and Wrap (01:37:56) Podcast Outro and Plugs Learn more about your ad choices. Visit megaphone.fm/adchoices

    1h 39m

  4. May 20

    OxyContin, Graffiti, and a Second Chance | J-Mac

    Jason “J-Mac” McDonald grew up moving between Malden, Medford, Chelsea, East Boston, and Revere. Bullied, angry, and constantly trying to fit in, he found identity in graffiti, hip-hop, stealing, and eventually drugs. What started as tagging trains and shoplifting turned into OxyContin, heroin, violence, overdoses, and years of addiction that nearly killed him. This conversation goes deep into Boston street culture in the late 90s and early 2000s — graffiti wars, robberies, fights, train yards, addiction, and the opioid epidemic that destroyed an entire generation. But this isn’t just a story about drugs. It’s about fear.Fear of not being enough.Fear of being judged.Fear of changing. J-Mac talks openly about heroin addiction, relapse after eight years sober, losing friends to fentanyl, getting arrested while living in sober housing, and the moment that finally forced him to rebuild his life for good. Today, he’s sober, works in recovery helping addicts rebuild their lives, speaks in jails and treatment centers, and has turned his graffiti roots into a legitimate art career through murals, canvases, and custom work across New England. This is one of the rawest Boston episodes we’ve done. 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) Meet J Mac (00:28) From Graffiti to Fine Art (02:37) Boston Roots and Opioids (04:19) Fear and Moving Around (06:50) Graffiti Alter Ego (08:47) Sponsor Break (09:37) Seventh Grade Heist Story (15:10) Sneakers and Peer Pressure (17:33) Haters and Self Belief (19:22) Recovery and Connection (24:02) High School Riot and Dad (28:16) First Opiates and Creativity (30:43) Hustles and Shoplifting (33:01) Boosting and Getaways (33:54) Graffiti Life and High Spots (34:16) Sticker Swap Paint Hustle (35:46) Recovery vs Old Habits (36:07) Mitochondria Supplement Ad (37:39) Oxy Takes Over (38:49) Cross Out Wars Explained (40:17) Mall Fight and Aftermath (42:33) Identity Beyond Graffiti (43:25) Relapse and Heroin Shift (46:13) First Heroin and Needles (49:18) Overdoses and Saving Friends (53:57) Fentanyl Changes Everything (01:00:47) Choosing Recovery and Detox (01:02:59) Family Intervention and First Sobriety (01:05:57) Secret Drinking Spiral (01:07:03) Halloween Rooftop Bust (01:08:14) Barrel Hideout Arrest (01:11:21) Court Cases Wake Up (01:12:29) East Boston Rehab Reset (01:14:38) 2013 Relapse Reality (01:17:18) Greg's Death Turning Point (01:20:20) Helping Others Through Barbering (01:22:43) Building an Art Career (01:31:17) Speaking and Jail Outreach (01:36:12) Final Recovery Message Learn more about your ad choices. Visit megaphone.fm/adchoices

    1h 39m

  5. May 15

    From Siberian Orphanage to Paralympic Legend | Jessica Long

    Jessica Long is one of the greatest Paralympic athletes of all time.18 gold medals. 31 total Paralympic medals. A career that changed sports forever. But this conversation has almost nothing to do with swimming. Jessica was born in Siberia, placed in an orphanage as a baby, and had both legs amputated before she was two years old. By 12, she was winning Paralympic gold medals for Team USA. The world saw dominance, records, sponsorships, and greatness. What they didn’t see was the emotional cost underneath it all. In this episode, Jessica talks openly about adoption, identity, feeling like a burden, chasing worth through winning, and the pressure that came with becoming a global athlete as a kid. She shares the story of meeting her birth family in Russia, forgiving her mother, battling burnout, struggling with an eating disorder, post-Olympic depression, and quietly slipping into alcohol abuse after Tokyo. This is a conversation about pain, resilience, purpose, and rebuilding your life from the inside out. Now nearly 500 days sober, pregnant with twin boys, and preparing for one final Paralympic run at LA 2028, Jessica is chasing something bigger than medals. This is one of the most emotional and honest conversations we’ve had. Thank you to our sponsors Ketone-IQ: ⁠ketone.com/rideout Code “RIDEOUT” Rho Nutrition: https://rhonutrition.com/ Code "RIDEOUT" Wild Roman: wildroman.com/rideout code “RIDEOUT15” Ken’s book now available here: https://www.theothersideofhard.com/ Chapters (00:00) Meet Jessica Long (00:10) What Paralympics Means (00:42) Athens at 12 (01:35) First Gold Mindset (02:59) Adoption and Worth (06:41) Growing Up Different (10:28) Finding Swimming (13:07) Paralympic Classifications (14:26) Community at Trials (19:09) Surgeries and Trauma (22:00) Making Team USA (25:46) Winning and Coming Home (29:11) Sponsors and Dominance (30:55) Nike Deal at 14 (31:38) Winning Addiction (32:44) Beijing Bronze Shock (34:40) Retiring Then Refocusing (35:52) Colorado Training Grind (37:55) Searching Birth Mom (39:54) London Paralympics Reveal (41:29) NBC Reunion Journey (48:25) Russia Media Frenzy (51:57) Meeting and Forgiveness (56:45) Sponsor Break Wild Roman (57:55) Purpose Beyond Medals (01:01:21) Training with Bowman (01:03:21) Training Group Highs (01:04:02) Rio Burnout Spiral (01:05:47) Therapy Marriage Reset (01:08:39) Tokyo Medals Post Blues (01:11:52) Wine Slippery Slope (01:14:42) Choosing Sobriety (01:20:05) No Victim Mindset (01:23:43) Paris Pain Belief (01:26:06) Twins And LA Dream (01:33:20) Legacy And Farewell (01:34:57) Subscribe And Sponsors Learn more about your ad choices. Visit megaphone.fm/adchoices

    1h 36m

  6. May 13

    The Enforcer Who Had to Rebuild. | Chris “Knuckles” Nilan

    Chris “Knuckles” Nilan was a Boston kid who became a Montreal Canadiens legend. 688 NHL games. A Stanley Cup. More than 3,000 penalty minutes. One of the toughest enforcers hockey has ever seen. But after the cheers stopped, the real fight started. Injuries. Painkillers. OxyContin. Heroin. Fentanyl. An overdose that nearly killed him. This conversation goes way deeper than hockey. We talk about identity… toughness… shame… addiction… and what happens when the thing that helped you survive becomes the thing you have to outgrow. Now Chris is sober. He’s at peace. And he doesn’t hide anything. This one is raw. Thank you to our sponsors Ketone-IQ: ⁠ketone.com/rideout Code “RIDEOUT” Helix Sleep: http://helixsleep.com/rideout for a special Memorial Day deal with 27% off (limited time offer!) Ken’s book now available here: https://www.theothersideofhard.com/ Chapters (00:00) Boston Roots Intro (01:03) West Roxbury Upbringing (01:46) Boston Toughness Talk (03:41) Northeastern Beanpot Years (04:23) Dad Pushes Him Forward (06:09) Prep School Breakthrough (07:47) Judge Mentor Story (12:01) Sponsor Break Ketone IQ (12:50) Drafted By Canadiens (13:46) Ride With Habs Legends (18:59) AHL Camp Reality Check (22:53) First Pro Fight Contract (26:32) Called Up To NHL (32:18) First NHL Games Nerves (35:36) Becoming More Than Enforcer (36:18) Helix Sleep Sponsor Break (37:33) Contracts and Earning NHL Money (38:29) Earning Trust in Montreal (39:17) Jacques Lemaire Skill Work (42:00) Young Stars and Slafkovsky (43:55) Meeting Karen and Marriage (44:59) Whitey Bulger Warning (48:30) Hometown Villain in Boston (51:12) Bruins Fights and Lessons (54:33) Old School Hockey Culture (55:41) Injuries and Career Decline (57:02) Boston Return and All Star (59:18) Talus Break on Parquet (01:01:07) Getting Older in Fights (01:04:39) Alcohol Drugs and Opiates (01:09:18) OxyContin Spiral and Rehab (01:14:51) Shame And Accountability (01:16:42) Oxy To Heroin Spiral (01:18:02) First Heroin And IV High (01:20:02) Fentanyl Overdose Wakeup (01:22:18) Recovery Work And Community (01:23:34) Boston Bonds And Rivalries (01:27:08) Priest Scandal Confrontation (01:35:17) Rebuilding In Montreal (01:36:52) Hawaii Turning Point (01:40:29) Vivitrol And Shame Secrets (01:43:05) Anger Control And Street Sense (01:49:05) Life Today And Farewell Learn more about your ad choices. Visit megaphone.fm/adchoices

    1h 55m

  7. May 8

    From the Raiders to Reinventing Himself | Miles Burris

    Former Raiders linebacker and actor Miles Burris joins Ken for a conversation about identity, reinvention, and what happens when the dream you chased your whole life suddenly ends. Miles grew up in Granite Bay, California obsessed with football from the moment he first put on pads. After becoming a standout linebacker at San Diego State, he was drafted by his childhood team — the Oakland Raiders — and thrown into the fire immediately as an NFL starter. He talks about the reality of playing linebacker in the league, facing quarterbacks like Peyton Manning and Tom Brady, rookie camp chaos, injuries, Toradol, identity loss after football, and the pressure of trying to hold onto a career that was slipping away. But this episode isn’t just about football. After injuries ended his NFL career, Miles fell into a dark stretch trying to figure out who he was without the game. His wife pushed him into acting classes, which eventually led to roles in The Righteous Gemstones, Lucifer, Safety, and more. He opens up about the transition from athlete to actor, the uncertainty of Hollywood, moving to Nashville, and how funny neighborhood skits on social media unexpectedly opened even bigger doors. This is a conversation about effort, reinvention, masculinity, confidence, and betting on yourself when life forces you to start over. Thank you to our sponsors Ketone-IQ: ⁠ketone.com/rideout Code “RIDEOUT” Athletic Brewing: https://athleticbrewing.com/ Code "RIDEOUT" Athletic Nicotine: athleticnicotine.com/rideout Code "RIDEOUT" Ken’s book now available here: https://www.theothersideofhard.com/ Chapters (00:00) Intro and Banter (00:53) Growing Up Granite Bay (01:10) Sports and Football Focus (02:37) High School Program and Position (03:42) NFL Dream and Dad Influence (06:06) College Choice and Recruiting (07:35) SDSU Struggles and Turnaround (12:07) Effort Mindset Lesson (14:41) Agents and Draft Prep (20:38) Draft Day Raiders Call (23:32) Rookie Camp Reality Check (25:34) Thrown Into the Fire (26:40) Facing QB Chessmasters (27:50) Raiders Reality Check (28:39) Near Pick on Brady (30:25) Kids Sports and Concussion Scare (32:30) Rookie Hazing and Camp Life (33:52) Injuries End the Dream (37:20) Toradol and NFL Pain Culture (42:01) PED Talk and Testing (44:05) Rookie Money and Benefits (47:32) Identity After Football (50:20) Why Nashville Won Them Over (51:12) Cross Country Move Horror Story (52:25) Host Backstory NYC to LA (53:19) Free Work Breakthrough (54:07) Leaving LA for Nashville (54:42) Reacher Neighbor Story (57:02) Football Ends Acting Begins (58:16) First Auditions No Fear (01:01:13) Big Roles and Gemstones (01:03:09) Self Tape Era Shift (01:05:08) Social Media Career Boost (01:11:33) Brands and YouTube Money (01:14:17) Raiders Content and Brady (01:15:21) Closing Advice and Outro Learn more about your ad choices. Visit megaphone.fm/adchoices

    1h 18m

  8. May 6

    Built to Destroy. Forced to Rebuild. | Mark Kerr

    Mark Kerr was one of the most dominant fighters on the planet. NCAA champion. Undefeated in early MMA. A force so powerful they called him The Smashing Machine. But behind the wins was a different story. Addiction. Shame. An overdose that nearly killed him. A life spinning out in real time. This conversation goes way deeper than fighting. We talk about identity… what happens when success isn’t enough… and what it really takes to rebuild your life when everything falls apart. Now, decades later, Mark is sober. He’s back. And his story is being told on the biggest stage in the world. This one hits hard. 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) Meet the Smashing Machine (01:52) Movie Feels Like Therapy (03:33) Shame and Addiction Spiral (08:14) Childhood and Wrestling Roots (09:13) Iowa Move Changes Everything (13:43) Syracuse Rise and Dyslexia (15:23) Felony Charges and Fallout (17:24) Rock Tour and Drug Scene (20:50) Rebuilding and NCAA Comeback (24:12) Foxcatcher World Team Era (31:46) Kurt Angle Rivalry and Loss (33:48) First MMA Fights in Brazil (38:36) Street Fight Mindset (38:58) Early UFC Was Brutal (40:40) Bare Knuckle Damage (42:25) UFC Pay To Win (43:20) Training With Real Resistance (45:43) Pride Fame In Japan (49:15) Yakuza And Fight Culture (50:43) Opiates And Cutting Corners (56:45) Methadone Overdose Narcan (01:03:14) Rehab And Coming Clean (01:11:46) Return To Grand Prix (01:13:12) Alcohol Takes Over (01:15:43) Training as Identity (01:16:20) Drinking Ends Fighting (01:17:19) Car Sales Spiral (01:18:42) Son Sparks Sobriety (01:19:48) AA and Recovery Tools (01:20:38) Documentary and Fate (01:21:31) Hollywood Call Back (01:24:14) Rights Bought Back (01:26:28) Dwayne Signs On (01:27:01) Pandemic Delays Project (01:29:37) Vancouver Time Capsule (01:33:01) Rebuilding the House Set (01:34:48) Ex Wife and Amends (01:37:49) The Rock Character (01:40:50) Paid in Perpetuity (01:42:18) Life After the Film (01:43:58) Responsibility and Wellness (01:46:35) Momentum Through Discipline (01:49:25) Why Not You (01:53:19) Closing and Subscribe Learn more about your ad choices. Visit megaphone.fm/adchoices

    1h 56m
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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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