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    Education

    RIDEOUT: The Other Side of Hard

    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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    Latest Episodes:
    OxyContin, Graffiti, and a Second Chance | J-Mac May 20, 2026
    Show notes

    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


    From Siberian Orphanage to Paralympic Legend | Jessica Long May 15, 2026
    Show notes

    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


    The Enforcer Who Had to Rebuild. | Chris “Knuckles” Nilan May 13, 2026
    Show notes

    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


    From the Raiders to Reinventing Himself | Miles Burris May 08, 2026
    Show notes

    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


    Built to Destroy. Forced to Rebuild. | Mark Kerr May 06, 2026
    Show notes

    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


    From Navy SEAL to Breaking Point to Building Lives | Johnny Wilson May 01, 2026
    Show notes

    Johnny Wilson’s life doesn’t follow a straight line—it crashes, burns, and rebuilds.

    From getting kicked out of the Naval Academy to fighting his way into the Navy SEALs…From combat deployments in Iraq to the trading floor at Goldman Sachs…From suicidal thoughts and a fractured life to finding healing in the darkest places…

    This is a story about what happens after the mission ends.

    Johnny opens up about war, trauma, identity loss, addiction, and the moment everything broke. And more importantly—how he found a way back.

    Now, through INVI MindHealth, he’s helping others do the same—using data, community, and new approaches to mental health to save lives.

    This one is raw, honest, and necessary.


    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 Johnny Wilson

    (00:51) Military Kid Upbringing

    (02:08) Fatherhood and Toughness

    (04:01) High School Football Days

    (06:22) Kids Today and Drinking

    (08:17) Non Alcoholic Beer Boom

    (10:13) Sponsor Ketone IQ

    (11:02) Naval Academy Culture Shock

    (12:52) Hazing and Leadership

    (14:37) Kicked Out and Rebuilding

    (23:33) Bootcamp and Ratings

    (28:28) Birthday Weekend Disaster

    (37:44) Bridge Bust and Near Jump

    (38:19) Cop Recognizes Them

    (38:51) Fence Hop Fallout

    (40:06) Faith and Second Chances

    (41:14) NAD Plus Sponsor Break

    (42:19) BUDS Cold Grind

    (43:53) Sand Runs and Boot Pace

    (47:29) Obstacle Course Wipeouts

    (50:14) Team Four and Deployment

    (51:11) New Guy Hazing Culture

    (52:17) Tridents and Birdcage

    (53:31) Mindset on Killing

    (56:13) Marriage and Home Front

    (01:02:01) Arrival in Baghdad

    (01:03:37) Turnover Ops and Mike Day

    (01:07:40) Sadr City and IED Chess

    (01:09:39) Drone Tech Evolution

    (01:11:30) Corruption and Integrity Talk

    (01:15:16) First Incoming Fire

    (01:16:18) Tunnel Vision Under Fire

    (01:16:52) Calm Leadership Moment

    (01:17:35) Debriefs and Evolving Tactics

    (01:19:17) Deployment Life Off Duty

    (01:20:17) Degrees During Deployments

    (01:22:08) Marriage Strain and Growth

    (01:26:26) Landing at Goldman Sachs

    (01:27:33) Corporate Culture Shock

    (01:31:32) Quitting and Returning to Teams

    (01:33:49) Back In and Global Deployments

    (01:37:38) Transition to Capital Group

    (01:41:01) Farm Life and Hunting Stories

    (01:48:53) Early Signs and Ibogaine Lead

    (01:52:12) Psychedelic Research Spark

    (01:53:40) Hitting Rock Bottom

    (01:54:35) Ibogaine Clinic Prep

    (01:56:01) Visions Then Darkness

    (01:59:40) Trauma Purge And Integration

    (02:01:49) DMT Death And Family

    (02:04:22) Therapy Not Recreation

    (02:07:10) Ending Cravings With Ibogaine

    (02:10:09) Building NV Mind Health

    (02:12:25) Wearables And Swim Buddy

    (02:17:50) ARPA-H Trials And Partnerships

    (02:23:00) Vulnerability And Community

    (02:28:31) Resources And Wrap Up

    (02:29:22) Subscribe And Sponsors

    Learn more about your ad choices. Visit megaphone.fm/adchoices


    War Took His Legs. Not His Life. | Jason Smith Apr 29, 2026
    Show notes

    Jason Smith is a retired U.S. Army infantry sergeant who lost both legs after stepping on an IED in Afghanistan in 2012.

    What followed wasn’t just survival—it was a complete rebuild.

    From months of rehab in Texas to refusing prosthetics, to eventually relearning how to walk, Jason had to let go of who he was to become someone new. Along the way, he faced PTSD, setbacks, and moments that nearly broke him—but kept choosing forward.

    Today, he’s a father of two, lives on a farm, and serves veterans through Catch A Lift Fund—helping others rebuild through fitness, community, and purpose. He’s also a USPA National Bench Press Champion, competing and winning against able-bodied athletes.

    This is a story about identity, resilience, and what happens after everything is taken from you.

    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) Meet Jason Smith

    (00:20) Growing Up and Enlisting

    (01:29) Boot Camp Reality Check

    (02:39) Stationed in South Korea

    (05:48) Fort Lewis and Deployment Prep

    (07:08) Training for Combat

    (11:15) First Missions and Fear

    (15:47) First Contact and Loss

    (20:14) Pinned Down and Enemy Tactics

    (23:44) The IED Blast

    (29:04) Evac to Kandahar and Germany

    (32:25) Texas Rehab and Prosthetics

    (38:26) Learning to Walk Again

    (39:22) High Tech Prosthetics Costs

    (40:53) Finding Strength and Farm Life

    (45:08) Rehab Mindset and Identity

    (46:08) Robbed Hit and Near Drowning

    (50:53) Marriage Kids and Homeschooling

    (55:09) Catch A Lift Mission

    (57:42) Warrior Games to Invictus Wins

    (01:00:10) USPA Nationals and Bench Rules

    (01:03:35) Purpose Advice and Farewell

    Learn more about your ad choices. Visit megaphone.fm/adchoices


    From Olympic Pressure to Peace and Purpose | Katie Hoff Apr 24, 2026
    Show notes

    Katie Hoff was one of the best swimmers in the world before most kids could drive. She made the Olympic team at 15, won multiple medals, and carried the pressure of being called the next great American swimmer.

    But behind the results was a different story.

    The weight of expectations. The identity tied to performance. And the realization that even success at the highest level didn’t bring what she thought it would.

    After missing teams, battling depression, and a pulmonary embolism that ended her career, Katie was forced to rebuild from the ground up.

    What followed wasn’t another comeback in the pool — it was something deeper.

    In this conversation, Katie opens up about IVF, Olympic pressure, identity, and how the Hoffman Process helped her find real peace. Now she’s building a new chapter through her podcast, her work, and starting a family.

    This is about what happens after the dream — and how to build something better.

    Thank you to our sponsors

    Ketone-IQ: ⁠ketone.com/rideout Code “RIDEOUT”

    Helix Sleep: http://helixsleep.com/rideout for 20% off

    Athletic Brewing: https://athleticbrewing.com/ Code "RIDEOUT"

    Ken’s book now available here: https://www.theothersideofhard.com/

    Chapters

    (00:00) Meet Katie Hoff

    (00:31) Pregnancy Excitement

    (02:04) Fertility Journey Begins

    (05:37) IVF Success Story

    (07:18) Training While Pregnant

    (08:59) Parenting Talk and Favorites

    (10:52) Sponsor Break Ketone IQ

    (11:41) Early Life and Swimming Start

    (14:46) North Baltimore Breakthrough

    (17:50) Olympic Trials Triumph

    (24:51) Team USA Camp Culture Shock

    (29:59) Sponsor Break Athletic Brewing

    (30:57) Athens 2004 Setback

    (32:52) Bouncing Back and Redemption

    (38:32) Turning Pro and Sponsors

    (43:00) Homeschool And Training

    (43:59) Beijing Pressure Cooker

    (46:07) Medals And Media Heat

    (49:23) Coach Split And Identity

    (56:40) 2012 Trials Turning Point

    (58:52) Pulmonary Embolism Scare

    (01:03:31) Retirement And Depression

    (01:04:40) Hoffman Process Breakthrough

    (01:10:57) Unfiltered Waters Mission

    (01:17:14) Baby Plans And Wrap Up

    Learn more about your ad choices. Visit megaphone.fm/adchoices


    Broken, Beat and a World Title | “Irish” Micky Ward Apr 22, 2026
    Show notes

    I’ve known Micky Ward for a long time. Before the fights people saw. Before the movie.

    This is a guy who was working as a corrections officer while trying to make it in boxing. Getting written off. Used as an opponent. Walking away from the sport… and coming back anyway.

    We talk about the part people don’t understand — the fear.

    He’ll tell you straight up, everyone’s scared. Anyone who says they’re not is lying.

    The difference is he learned how to control it and still go forward.

    We get into Round 9 of the first Gatti fight — what it actually felt like to be in there, hurt, exhausted, and still making the decision to fight.

    We talk about his family, what the movie got right and wrong, and what it takes to keep going when everything in you is telling you to stop.

    This one is about endurance. Not talent.

    Just deciding you’re not done.

    Thank you to our sponsors

    • Ketone-IQ: ⁠ketone.com/rideout Code “RIDEOUT”
    • Athletic Nicotine: athleticnicotine.com/rideout Code "RIDEOUT"

    Ken’s book now available here: https://www.theothersideofhard.com/

    Chapters

    (00:00) Lowell and Jailhouse Days
    (02:51) Early Boxing Roots
    (03:30) Dickie as Trainer
    (06:15) Turning Pro and Setbacks
    (07:58) Fear and Fight Night Nerves
    (09:54) Dickie vs Sugar Ray
    (12:59) Gym Fighters and Sparring
    (17:12) Title Shot vs Shea Neary
    (20:42) Sanchez Comeback KO
    (25:42) Family Life and Sisters
    (27:46) Making The Fighter Movie
    (34:52) Movie Ending Explained
    (35:05) Story Sources Documentary
    (35:44) Family Reactions Premiere
    (38:26) Nephew Sean And Fame
    (40:14) Race Sports And Prison
    (42:33) Toughest Opponents Lessons
    (45:40) Title Stripped And Setbacks
    (48:24) Gatti Call And Mindset
    (51:09) Fight Breakdown Ninth Round
    (57:28) Trilogy Injuries And Surgery
    (01:01:13) Friendship After Trilogy
    (01:02:10) Life After Boxing Wrap
    (01:04:17) Podcast Outro And Plugs


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    Living on the Edge Without Losing Each Other | Laird Hamilton & Gabby Reece Apr 17, 2026
    Show notes

    I went out to Malibu to sit down with Laird Hamilton and Gabby Reece.

    Everyone knows Laird for big-wave surfing and doing things most people wouldn’t even attempt. But what stood out to me wasn’t the waves—it was how he thinks about fear.

    He doesn’t avoid it. He uses it.

    And then there’s Gabby. She’s watching the person she loves go put himself in real danger, and instead of trying to control it, she’s built a level of trust that most people just don’t have.

    We also got into their marriage.

    They almost got divorced early on. Not in theory—actually close. And what changed everything was learning how to deal with problems immediately. No letting things build. No saying nothing and pretending it’s fine.

    Say it. Fix it. Move on.

    It sounds simple, but most people don’t do it.

    We talked about discipline, addiction, reputation, and why people look at someone’s life and call it “lucky” without having any idea what it took to get there.

    This isn’t a surfing conversation.

    It’s about fear, ownership, and doing the work—whether that’s in your life, your career, or your relationship.

    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) Welcome To Malibu

    (00:35) Daily Training Routines

    (01:54) Competition And Pickleball

    (03:15) Facing Big Wave Fear

    (08:00) Trusted Surf Safety Team

    (09:43) Why Gabby Quit Surfing

    (13:54) How They Met And Worked

    (15:37) Man Skills And Alone

    (17:40) Marriage Rules And Conflict

    (27:00) Parenting And Values

    (30:22) Island Upbringing Stories

    (36:29) Laird Youth Sports And Work

    (38:34) Finding Your Tribe

    (40:20) Open Gate Hospitality

    (42:01) Unexpected Famous Encounters

    (44:29) Therapy And Self Care

    (46:30) Luck Is Law

    (49:54) Journey Over Destination

    (53:51) Reputation Long Game

    (56:00) Daily Marriage Practice

    (01:00:08) Vintage Car Story

    (01:02:25) Hamilton House Vision

    (01:07:10) Time Over Money

    (01:09:01) Portal Responsibility Wrap

    (01:14:32) Podcast Outro And Plugs

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