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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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  1. 78

    From a Prison Cell to Nike Brand Director | Jordan Rogers

    Jordan Rogers was using heroin at 15. By the time he landed in county jail, he weighed 116 pounds. His parents had spent his college fund on rehab, and he was facing the possibility of 20 years in prison. I know what it’s like to organize your entire life around getting high. There was a lot in this conversation that hit home for me.  We get into his 396 days locked up, what finally changed when he stopped trying to outsmart every rule, and what happened when he read his mother’s account of everything his addiction had put her through. Getting sober wasn’t the finish line. He became a personal trainer, earned his degree at SMU, and spent four and a half years chasing a job at Nike. He went from working in a factory store to becoming a brand director, working with some of the biggest names in sports.  Then he made another hard decision: leaving the job he’d spent years trying to get. We talk about choosing his family, building his own business, and why neither of us wants to give up the freedom of working for ourselves. Jordan didn’t get to undo his past. He had to get honest about it and decide what he was going to do next. That’s what this conversation is about.  Follow Jordan on Instagram: @jordanrogers.  Please subscribe, leave a comment, and share this episode with someone who needs to hear it.  Thank you to our sponsors Our Title Sponsor ROKA: www.roka.com/ Code “RIDEOUT” AMP Fitness: amp.ai/rideout   Ken’s book now available here: https://www.theothersideofhard.com/ Chapters (00:00) Meet Jordan Rogers (00:48) Mindset Over Hype (02:22) Radical Accountability (06:35) Prison Programs Debate (08:37) Guard Life Inside (11:08) Growing Up in Dallas (11:43) Sponsor Break Roka (13:21) Sports Dreams Collapse (16:49) Heroin at Fifteen (21:50) Addiction War Stories (24:57) Parents Intervene (28:36) Hustle to Healing (33:46) First Arrest at Fourteen (37:38) Coke Bust Setup (39:46) Busted Before 19 (40:48) Tiny Bag Big Charge (42:24) Deferred Probation Trap (43:47) Relapse And Highway Chase (45:08) Beating Drug Tests Fails (48:06) County Detox Reality (52:00) Vivitrol And Suboxone (56:56) Kicked Out Sober (01:00:31) Jail Cell Surrender (01:05:21) SAFP Last Chance (01:08:37) Release And Recovery Start (01:09:11) Chasing The Nike Dream (01:10:57) Ekin Role Explained (01:15:12) Hustling To Stand Out (01:18:15) Nike Campus Gearhead (01:18:25) NIL Changed Everything (01:18:54) Outworking the MBA Crowd (01:19:29) Nike Alpha Competitions (01:20:11) Climbing Nike Football (01:21:36) Sneaker Perks and Collections (01:24:21) Golf Gear and Clubs (01:27:31) Moving for Family (01:31:00) Leaving Nike Leap (01:33:33) NIL Consulting Pivot (01:36:37) Unemployable Freedom (01:51:13) Skin in the Game (01:53:54) Wrap Up and Subscribe Learn more about your ad choices. Visit megaphone.fm/adchoices

  2. 77

    From Compulsive Gambler to a $465 Million Exit | Rich Galgano

    Rich Galgano came back from Vegas so broke that a friend had to pay to get his car out of the airport parking lot. He swore he was done gambling. Then he got home, found $500, and went straight back to another casino. I know what it’s like to promise yourself you’re finished and then do the same shit again.  This week, I sat down with Rich to talk about the gambling addiction that was taking over his life, the three-day bender that finally made him ask for help, and walking into Gamblers Anonymous at 23. He told me he hasn’t gambled in nearly 33 years. But getting out of the casino was just the beginning.  Rich and his business partner started Windy City Wire with a $100,000 bank line and a business plan they worked out at Subway. Almost immediately, they were fighting a lawsuit that threatened to shut them down. The story of how he found the right lawyer and fought back is fucking unbelievable. He went on to build a company that sold to Diploma PLC in a $465 million deal in 2020.  We get into recovery, knowing your worth, choosing the right partners, buying back your own business, and why money doesn’t fix what’s going on in your head. Rich also shares the heart problems that forced him to take his health seriously and what he’s building now with Scylos and Reload. This guy can tell a story. Hope you guys enjoy this one.  Follow Rich: @richgalganoHis book: Down to the Wire: The Outlandish Tale of How I Quit Gambling to Win Big. Thanks to ROKA for supporting the show. Please take a minute to subscribe and leave a comment. It makes a huge difference. More about the show at theothersideofhard.com. Thank you to our sponsors Our Title Sponsor ROKA: www.roka.com/ Code “RIDEOUT” Ken’s book now available here: https://www.theothersideofhard.com/ Chapters (00:00) Meet Rich Galgano (00:40) Sponsor Shoutout Roka (01:08) Growing Up in Bolingbrook (02:01) Old School Childhood Lessons (04:23) Sports Setback Sparks Drive (06:51) Early Gambling and Work Ethic (08:27) College Poker and Party Fight (13:08) Riverboat Casinos Take Over (15:01) Blackjack Wins and Two Lives (16:45) Wire and Cable Sales Origins (21:57) Cold Calling and Big Margins (25:05) Chapter 11 Chaos and Mentors (29:53) Benders and Rock Bottom Signs (30:59) Broke at O'Hare (31:30) Back to the Casino (32:51) Three-Day Betting Spiral (34:30) Calling 1-800-GAMBLER (35:47) First GA Meeting Reality (39:14) 33 Years Clean (40:50) Clarity and Career Ambition (45:47) Starting the Wire Business (48:53) TRO Lawsuit Shock (52:39) GA Connection Finds Real Lawyer (59:16) Dan Purdum Courtroom Turnaround (01:02:22) Depositions and Fighting Back (01:03:14) Leaking Price Fixing (01:04:31) Winkle Breaks Under Deposition (01:06:40) Settlement Without Paying (01:08:44) Business Explodes After Lawsuit (01:09:25) Why Take Investors (01:10:16) Marriage and Staying Grounded (01:12:49) Money Doesn’t Fix You (01:13:42) Raising Money in LA (01:19:46) Taking Chips Off Table (01:20:40) Dodging a Bad LBO (01:23:15) The $6.5M Wire Moment (01:25:08) Private Equity Exit Pressure (01:28:48) The Great Buyback (01:33:04) Selling for $465M (01:35:34) Why Sell to Strategic (01:36:53) Family Office Focus (01:37:09) Cylos Endpoint Vision (01:38:06) Embezzlement and Rebuild (01:38:44) Stateless OS Explained (01:40:48) Go To Market Fundraising (01:41:30) Son Runs Investments (01:42:47) Venture Lessons and Diligence (01:47:53) Health Scare Wake Up (01:53:24) Longevity and Biohacking (01:58:05) Reload Recovery Tool (02:06:00) HYROX and Family Drive (02:09:17) Book Plug and Wrap Learn more about your ad choices. Visit megaphone.fm/adchoices

  3. 76

    19 Million Followers, Losing Everything, and Starting Over in Nashville | Tayler Holder

    Tayler Holder has 19 million followers on TikTok, millions more across social media, and a story that goes way beyond being an internet star. Tayler grew up in tiny Alvarado, Texas, racing dirt bikes and chasing adrenaline from the time he was a kid.  He left traditional high school after ninth grade to train and race motocross, then eventually shifted his focus to Vine, Musical.ly, and social media. He moved to Los Angeles determined to figure it out, literally hanging around the apartment complex where the biggest creators lived until he started meeting them. That hustle eventually led to Magcon, massive social growth, TikTok, the Hype House era, and ultimately building his own creator house called The Compound. We also get into Tayler’s love of fighting. He trained with Ryan Garcia, sparred Canelo Alvarez, fought Gib in front of a massive crowd in Miami, and later took a fight on four days’ notice for $50,000 and won by second-round knockout. Then everything changed. Tayler talks about the public accusations made against him, which he denies, losing brand deals, spending huge amounts of money on attorneys and crisis PR, financial collapse, and reaching such a dark place that he attempted to take his own life. He also tells the story of a former business manager who he says used his American Express account without permission and failed to file his taxes. Eventually, Tayler left Los Angeles for Nashville, wrote “Drive” with Shay Mooney, bought a farm, started pursuing country music independently, and began trying to build a completely different life. We talk about fame, validation, money, fighting, mental health, faith, music, and what happens when everything you thought mattered disappears. Thank you to our sponsors Our Title Sponsor ROKA: www.roka.com/ Code “RIDEOUT” Wild Roman: wildroman.com/rideout Code “RIDEOUT15” Ken’s book now available here: https://www.theothersideofhard.com/ Chapters (00:00) Meet Tayler Holder (00:31) Followers and Brand Deals (01:05) ROKA Gift and Sponsor Shoutout (01:54) Small Town Texas Roots (02:17) Rodeo Life and Adrenaline Kid (03:30) Vine Beginnings and Early Content (04:46) Dropping Out for Motocross (09:21) Brutal Pit Bike Crash Story (14:55) Sponsor : ROKA (16:35) LA Hustle to Boxing Camps (28:55) Sparring Canelo Up Close (29:27) Canelo Shoulder Attack Lesson (29:53) First Fight Nerves (30:19) Backstage With Jake And Tyron (31:51) Sponsor: Timeline (33:23) Vine To TikTok Explosion (36:06) Monetizing Followers And Brands (36:58) Hype House Drama To The Compound (48:42) Accusations Rock Bottom And Faith (58:59) Money and Validation (59:45) Hometown Crabs and Haters (01:00:35) Accusations and Financial Freefall (01:01:10) Business Manager Betrayal (01:04:16) LA Teen Years and Learning Music (01:06:48) Friendship Ends Over Politics (01:08:18) Nashville Move and New Start (01:09:55) Farm Life and E-Bike Chaos (01:17:21) Indie Music and Mental Health Learn more about your ad choices. Visit megaphone.fm/adchoices

  4. 75

    The Rise, Fall, and Reinvention of an Olympic Champion | Missy Franklin

    Missy Franklin is one of the greatest swimmers of all time. She made her first Olympic Trials at 13 years old, and four years later she went to London and absolutely dominated—four gold medals, a bronze, and a world record in the 200 backstroke. But what I loved about this conversation is that we spent just as much time talking about what happened when things stopped going perfectly. Four years after London, Missy went into the Rio Olympics carrying enormous expectations, injuries, sponsor pressure, and the weight of trying to recreate the greatest week of her life. She didn't make a single individual final and describes those eight days as some of the hardest of her life. After bilateral shoulder surgeries and fighting for 18 months to get back, she eventually had to retire at only 23 years old. We talked about all of it—the insane suffering swimmers put themselves through, making the Olympics as a teenager, what it actually feels like to win a gold medal, breaking a world record, turning down life-changing money to swim at Cal, failing publicly in Rio, and learning that sometimes the way you lose says more about you than the way you win. Missy is also in a completely different chapter now. She's a mom of two, she's training for HYROX, she's somehow learning to love running, her husband Hayes is racing professionally in triathlon, and they're building Gold, a goal-setting platform for athletes. I really loved this conversation. Missy is exactly who you hope she is—positive, competitive, thoughtful, and completely honest about both the incredible highs and really difficult lows that came with her career. Hope you guys enjoy this one. Follow Missy: @missyfranklin88 Please subscribe to The Other Side of Hard, leave a comment, and let me know what you think of the episode. Learn more about the show, my upcoming book, and everything we're doing at theothersideofhard.com. Thank you to our sponsors Our Title Sponsor ROKA: www.roka.com/ Code “RIDEOUT” Wild Roman: wildroman.com/rideout Code “RIDEOUT15” Ken’s book now available here: https://www.theothersideofhard.com/ Chapters (00:00) Meet Missy Franklin (00:18) Why Swimming Hurts (00:52) Swimming vs Running (02:45) Husband Triathlon Journey (05:55) Missy Finds Hyrox (06:37) Sponsor Gifts Moment (07:24) Growing Up in Colorado (09:31) Teen Olympic Trials (12:56) Sponsor: Roka (14:36) Support System and School (19:42) London Olympics Breakthrough (31:54) Record Heat Magic (32:14) Celebrity Shoutouts (32:32) Gold Medal Reality (34:11) Parent Reactions (34:45) Sponsor: Wild Roman (35:46) Motherhood Moments (37:19) Learning To Fail (39:40) Staying Amateur (41:54) NCAA Glory Days (43:34) Pro Pressure Spiral (45:27) Rio Trials Heartbreak (50:36) Retirement And Next Learn more about your ad choices. Visit megaphone.fm/adchoices

  5. 74

    International Fugitive to UFC Top 10 | Ian Heinisch

    Former UFC fighter Ian Heinisch sits down with Ken Rideout for one of the wildest stories ever told on The Other Side of Hard. Ian grew up in Colorado as an elite wrestler with the talent to compete at the highest levels, but drugs, alcohol, arrests, and self-destruction quickly began overtaking his life. After leaving school and spiraling further, he moved illegally to Canada, worked door-to-door sales, was arrested and eventually deported. Back in Denver, Ian began trafficking ecstasy before being caught in a sting operation. Facing serious charges, he fled the United States for Europe. What followed was extraordinary. Ian eventually landed in Tenerife, where he says he became an international cocaine mule, traveling through Colombia, Venezuela and Aruba and swallowing packages of cocaine to transport them back to Spain. He was eventually caught, sentenced to prison, and spent roughly two and a half years incarcerated in Spain before being returned to the United States. His trip home included Rikers Island and an 11-day prisoner transport back to Colorado. Once free, Ian committed himself to mixed martial arts. He rapidly climbed through the sport, reached the UFC and broke into the top 10 — while privately battling another devastating addiction to opioids. Ian opens up about finding sobriety through his Christian faith, his rise through the UFC, serious health problems, concussion-like symptoms that ultimately forced him away from fighting, and the difficult process of rebuilding his identity once again. Today, Ian is an entrepreneur, works in crypto, and serves as president of Bare Knuckle Ice Wars. This is a conversation about addiction, prison, survival, fighting, faith, purpose, and the possibility of completely changing the direction of your life. Thank you to our sponsors Our Title Sponsor ROKA: www.roka.com/ Code “RIDEOUT” AMP Fitness: amp.ai/rideout  Ken’s book now available here: https://www.theothersideofhard.com/ Chapters (00:00) Meet Ian Heinisch (00:43) Wrestling Roots and Drive (02:51) Addiction Takes Hold (07:47) Rehab Ranch and Expulsion (23:27) Canada Hustle and Chaos (30:49) Border Hustle Into Canada (32:28) Holding Cell Withdrawal Chaos (37:16) Courtroom Slip And Deportation (47:33) Denver Ecstasy Operation Sting (55:37) Europe Run To Coke Mule Trips (01:03:53) Cali Jungle Connections (01:05:41) Parties Culture Shock (01:08:15) Swallowing Balloons (01:12:38) Airport Bust Tenerife (01:19:15) Prison To Rikers (01:35:05) Rikers Survival Night (01:38:16) Marshals Transfer Nightmare (01:40:33) MMA Rise and Oxy Spiral (01:43:48) Faith Turnaround and UFC Run (01:50:24) Health Crash New Purpose Learn more about your ad choices. Visit megaphone.fm/adchoices

  6. 73

    Brutal Hits, Broken Bodies & the Business of Football | Bernard Pollard

    Bernard Pollard earned a reputation as one of the NFL’s most feared hitters — and became known throughout New England as the “Patriot Killer.” In this episode, Bernard sits down with Ken Rideout to talk about the mentality behind his violent style of play, growing up angry in Fort Wayne, Indiana, using football as an outlet, choosing Purdue, and making the jump from a three-call high school defense to the complexity of major college football. Bernard takes Ken inside his NFL career: representing himself, getting drafted by Kansas City, refusing to pay a $45,000 rookie bar tab, the hit that tore Tom Brady’s ACL, being cut after Scott Pioli arrived from New England, battling with John Harbaugh in Baltimore, winning a Super Bowl with six broken ribs, and experiencing firsthand how ruthless the NFL business can be. He also opens up about the dysfunctional culture he encountered in Tennessee, the decision to turn down another opportunity with Oakland and retire, and why walking away ultimately helped him become a better husband and father. Today, Bernard says football was his talent — but teaching, training and developing players is his gift. He shares how Jalen Ramsey became one of his first major training clients and why coaching athletes gave him a new purpose after football. This is Bernard Pollard beyond the hits. Thank you to our sponsors Our Title Sponsor ROKA: www.roka.com/ Code “RIDEOUT” Wild Roman: wildroman.com/rideout Code “RIDEOUT15” Ken’s book now available here: https://www.theothersideofhard.com/ Chapters 00:00 Meet Bernard Pollard 00:34 Embracing the Villain 01:30 Born to Hit 02:32 NFL Safety Rules Debate 04:54 Helmet Pads and Optics 06:24 Fort Wayne Roots 11:31 Anger as Fuel 21:28 Purdue and Going Pro 32:32 Sideline Coaching Tension 33:47 Teachers Versus Coaches 36:00 Protecting Jalen’s Development 37:03 Blackballed From Coaching 38:24 Gruden Example and Ad Break 40:11 Deion Sanders Training Summer 44:34 Declaring and Tiller Fallout 54:46 Draft Day and NFL Reality 01:00:48 NFL Culture Shock 01:01:15 Player Development Mentor 01:01:53 Megan’s Big Sacrifice 01:02:59 Training Camp Reality 01:04:59 Rookie Bar Bill Standoff 01:07:59 First Money Lessons 01:12:27 Brady Hit Fallout 01:17:28 Baltimore to Super Bowl 01:28:14 Owning the Bad Game 01:28:39 Cut Loose in Baltimore 01:30:33 Exit Physical Sabotage 01:33:08 Landing With the Titans 01:34:30 Titans Culture Shock 01:39:45 Walking Away From Money 01:42:14 Retirement and New Purpose 01:50:04 Family Growth and Farewell Learn more about your ad choices. Visit megaphone.fm/adchoices

  7. 72

    The Cop Who Went to Prison for 19 Years | Kent McGowen

    Kent McGowen spent years enforcing the law. Then he spent nearly two decades behind bars. Kent is a former Houston police officer and Harris County deputy who was convicted of murder after fatally shooting Susan White while serving a felony retaliation warrant in 1992. Kent has maintained for more than three decades that the shooting was justified and that he was wrongfully prosecuted. He takes Ken through the entire case: the informant and stolen-gun investigation that started it, White’s threats, the warrant, the forced entry, the moment he says White pointed a .32-caliber pistol at him, and the three shots that changed his life forever. Kent also details his allegations of misconduct by prosecutors and investigators, his first conviction being overturned on appeal, the disastrous second trial that sent him to prison, and what he witnessed during 19 years inside the Texas prison system. He ultimately walks Ken through the letters that finally brought outside attention to his case, the people in law enforcement who came to his aid, his 2021 release, and the fight he says is still far from over. Thank you to our sponsors Our Title Sponsor ROKA: www.roka.com/ Code “RIDEOUT” AMP Fitness: amp.ai/rideout  Ken’s book now available here: https://www.theothersideofhard.com/ Chapters (00:00) Meet Kent McGowen (00:42) Early Policing Days (04:46) Texas Law Enforcement Breakdown (06:43) Informant and Gun Crew (10:27) Sponsor Break Roka (12:08) Buy Bust Gone Sideways (16:41) Susan White Arrives (25:32) Threats and Retaliation Case (29:59) Phone Records No Link (30:38) Midnight DA Intake (33:17) Warrant Delay Whiteout (35:12) Sergeant Orders Warrant Run (39:11) Calling Suspect First (40:48) Door Knock Escalation (43:59) Legal Theory Unlawful Warrant (47:34) Forced Entry And Shooting (55:19) Aftermath And Scene Chaos (58:39) Deputy Matt And Prior Contact (01:02:50) Captain Harper Statement Shift (01:03:43) Fax Cover Sheet Fallout (01:04:40) Grand Jury Pressure Tactics (01:10:27) Sealed Indictment Arrest (01:12:43) Denholm and the Corrupt Clique (01:20:45) Prosecutor Harassment Campaign (01:26:21) Conviction and Appellate Bond (01:30:32) Appeals Victory and State Pushback (01:33:52) Appeals Win Streak (01:35:33) DA Targets His Wife (01:37:53) Airport Intimidation (01:41:01) Hiring Cogdell (01:43:56) Lawyer Chaos Spiral (01:45:51) Trial Strategy Disaster (01:50:29) Eleventh Hour Warning (01:56:25) Coked Up Closing (01:58:00) Guilty and Bond Revoked (02:00:34) Processed Into Prison (02:03:17) Safekeeping Shock (02:04:40) Intake and Sociology Interviews (02:05:20) Case File Shock and Hidden Discovery (02:06:57) Zimmerman Takes the Case (02:08:31) How Prosecutors Rig Cases (02:09:53) First Units and Bench Warrant Detour (02:11:11) Goree Unit and Karla Faye Tucker Cell (02:14:13) Jury Confusion and No Protective Custody (02:16:48) Price Daniel Unit and Dangerous Cellmates (02:19:50) Juan Flores Heart Attack Crisis (02:28:59) Retaliation Transfer and Solitary (02:30:07) Pack Unit Life and Surviving on Anger (02:32:15) Visits, Parole Setback, and Journaling (02:34:05) Parole Setoff Trap (02:34:51) Corruption And Beatings (02:37:57) Parole Shakedown Revival (02:41:17) Letters That Got Help (02:46:21) Immediate Release Decision (02:50:12) Walking Out After Loss (02:56:07) Life On Intensive Parole (03:01:10) Aftermath And New Cases (03:03:17) Fundraising And Wrap Up (03:04:54) Host Outro And Subscribe Learn more about your ad choices. Visit megaphone.fm/adchoices

  8. 71

    The Wall Street Executive Who Had Everything—Except Peace | James “Jet” Davies

    James “Jet” Davies spent more than two decades inside high finance, eventually becoming CEO of Deutsche Bank’s broker-dealer for the Americas. But behind the titles, money, and success was a life that was beginning to unravel. James joins Ken to trace the entire path—from growing up in London and attending an elite all-boys school, where he experienced emotional and sexual abuse, to studying law at Bristol after being rejected by Oxford, entering one of London’s top law firms, and eventually making the leap to Deutsche Bank. He takes Ken inside the brutal culture of London trading floors, the explosion of derivatives, the 2008 financial crisis, and the strange reality of climbing higher while questioning whether any of it was making him happier. Then, in 2019, James crashed. He opens up about self-harm, therapy, his marriage reaching a breaking point, and the process of separating his identity from money and status. When Deutsche Bank ultimately chose not to extend his contract in 2024, the career he had spent nearly 25 years building was suddenly over. Instead of going back, James and his partners bought an 85-acre campus in the Berkshires and transformed it into The Time—a retreat space built around nature, connection, and creating the kind of reset James once desperately needed himself. It’s a conversation about ambition, trauma, money, rejection, burnout, and what happens when achieving everything you thought you wanted still isn’t enough.  Thank you to our sponsors Our Title Sponsor ROKA: www.roka.com/ Code “RIDEOUT” Wild Roman: wildroman.com/rideout Code “RIDEOUT15” Ken’s book now available here: https://www.theothersideofhard.com/ Chapters (00:00) Meet James Jet Davies (00:30) Strava Rivalry Origins (01:39) Marathon Times Talk (02:14) London Roots and Schooling (03:09) Inside Elite Boys School (06:02) Abuse and Trauma Unpacked (07:52) Therapy and Healing Stages (10:10) How Predators Gain Access (12:28) Roka Eyewear Sponsor (14:08) Warning Signs at Boarding (15:42) Strict Discipline and Bullying (17:04) Single Gender School Effects (18:59) American Schools and Parenting (22:21) Secondary School Shift (27:49) Competition Winners and Losers (28:56) Sports and the Jet Nickname (30:06) Parents Expectations and Success (31:21) Finding Your Own Path (32:35) Loving Work Now (33:09) Parents Pushing Kids Away (34:17) Trauma Surgeon Passion (35:57) Skincare Ad Break (36:58) Oxford Rejection Story (39:57) Brutal Oxford Interviews (43:34) Setbacks Build Resilience (45:37) Bristol And Posh Crowd (46:08) Law Firm Pipeline (47:45) Derivatives And Leverage (49:35) Market Manipulation Rant (52:37) Deutsche Bank Jump (57:54) Legal Dept Vs Traders (59:02) Breaking Into Trading Desk (01:00:16) UK Trading Floor Vicious (01:00:53) Trading Floor Hazing (01:02:51) London Finance Wild West (01:04:50) Back to Legal and Redemption (01:06:43) Structured Finance Explained (01:07:45) Crisis Unwinding and Promotions (01:10:46) Post Crisis Pay and Talent Shift (01:14:09) New York Move and Culture Shock (01:17:13) American Optimism vs UK Cynicism (01:23:46) 2019 Leadership Pressure Cooker (01:26:43) Mental Health Crash in Finance (01:29:53) Self Harm Confession (01:31:23) Therapist And SSRIs (01:32:50) Couples Session Breakthrough (01:33:55) COVID Reset And Career Shift (01:36:51) Leaving Deutsche Bank (01:40:31) Buying Berkshire Retreat Campus (01:45:04) Running Thyme Retreats (01:46:26) Hospitality Lessons And Rules (01:49:13) Upcoming Running Retreat Promo (01:53:48) Life After Finance Mindset (01:58:30) Wrap Up And Subscribe Learn more about your ad choices. Visit megaphone.fm/adchoices

  9. 70

    From Small-Town Kid to Everest, Equinox & IRONMAN CEO | Scott DeRue

    Scott DeRue has spent his life creating experiences that push people beyond what they thought was possible. Ken sits down with his longtime friend and current CEO of The IRONMAN Group to talk about growing up in small-town North Carolina, being told during his first performance review that he “wasn’t smart enough,” walking away from a lucrative consulting career in search of purpose, becoming a University of Michigan professor and eventually the youngest dean of a top business school, and leaving the security of academia to help lead Equinox through the COVID crisis.  Scott also shares how mountaineering became one of the defining forces in his life, what it took to climb Everest and complete the Seven Summits, the terrifying risks of the Khumbu Icefall and descent from Everest, and why getting to the summit is only half the job.  Now leading The IRONMAN Group, Scott explains why he believes the company is ultimately in the “dream fulfillment business,” what he learned from rebuilding Equinox, why athlete feedback matters, and the decision to bring the men’s and women’s IRONMAN World Championship back together in Kona.  Ken and Scott also revisit the 2023 Gobi March in Mongolia—the race where they first met and Ken somehow went from having never run an ultramarathon or camped to winning the entire thing. Thank you to our sponsors Our Title Sponsor ROKA: www.roka.com/ Code “RIDEOUT” AMP Fitness: amp.ai/rideout  Ken’s book now available here: https://www.theothersideofhard.com/ Chapters (00:00) Scott DeRue Intro (00:32) Gobi March Bond (01:46) Small Town Roots (02:02) Schoolwork And Drive (05:08) Sports And Pole Vault (06:05) UNC And Water Skiing (09:08) From Bio To Business (09:46) Boston Consulting Start (11:16) Sponsor Break Roka (12:56) Brutal Review Lesson (18:41) Quarter Life Crossroads (21:02) PhD Path To Michigan (25:58) Rapid Rise To Dean (28:34) Transformational Teaching (30:43) Money Vs Purpose (32:41) Restroom Empire Moment (34:43) Loving the Work (35:04) From Professor to Dean (37:26) Youngest Dean Pressure (38:52) Mission Driven Leadership (40:28) Sponsor Break Amp (41:04) Mountaineering Origin Story (46:16) Seven Summits Quest (50:02) Everest Risks and Resilience (52:18) Khumbu Icefall Focus (55:46) Summit and Descent Dangers (01:03:35) Equinox During Covid (01:08:51) Rebuilding and Ironman Pull (01:10:13) Ironman Obsession (01:10:43) Taking the CEO Call (01:11:50) Ironman Beyond Triathlon (01:12:51) Lifestyle and Identity (01:15:03) Feedback and Responsibility (01:15:33) Kona War Stories (01:18:00) Dream Fulfillment Mission (01:20:38) Kona Together Again (01:22:10) Designing Wave Starts (01:24:44) Midnight Finish Magic (01:29:43) Will He Race One (01:30:20) Gobi March Memories (01:34:04) Wild Characters and Lessons (01:39:27) Gratitude and Wrap Up (01:40:23) Subscribe and Sponsors Learn more about your ad choices. Visit megaphone.fm/adchoices

  10. 69

    Jail, Navy SEALs, Fentanyl & the French Foreign Legion | Taylor Cavanaugh

    Taylor Cavanaugh’s life has been a cycle of achievement, self-destruction, and rebuilding. Before becoming a Navy SEAL, Taylor had already been expelled from school, arrested repeatedly, survived a violent car crash, and served time in county jail. After multiple branches of the military turned him away, the Navy finally gave him a shot. Taylor made it through BUD/S and Hell Week and eventually served with SEAL Team 7 as a communications specialist, JTAC, and sniper. His deployments took him to Yemen and Iraq, where he called airstrikes, worked alongside local forces, and operated under rocket and mortar fire. But outside the teams, the same patterns that had followed him since his teenage years never fully disappeared. An aggravated assault case nearly sent him to prison. Another alcohol-fueled incident and a positive steroid test eventually ended his SEAL career. Civilian success followed, but so did Adderall, Xanax, opiates, and eventually fentanyl. Taylor went from working in real estate development and venture capital to withdrawing alone in Hawaii, living out of his truck, nearly broke and contemplating suicide. Instead of ending his life, he bought a one-way ticket to France. Taylor walked through the gates of the French Foreign Legion, surrendered his passport, was given a new identity, and started again at the bottom. He spent years running, cleaning toilets, training in the French Alps, deploying to Estonia and conducting jungle operations against illegal gold mining operations in French Guiana. Today, Taylor has turned the discipline that helped rebuild his own life into a coaching business focused on consistency, personal responsibility, and controlling the controllables. This is Taylor Cavanaugh’s story. Follow Taylor: @tcavofficial Thank you to our sponsors Our Title Sponsor ROKA: www.roka.com/ Code “RIDEOUT” Wild Roman: wildroman.com/rideout Code “RIDEOUT15” Ken’s book now available here: https://www.theothersideofhard.com/ Chapters (00:00) Meet Taylor Cavanaugh (00:20) Gloucester Rough Edges (01:27) Marine Base Upbringing (01:48) Pilots And Air Ops (04:53) JTAC Danger Close (07:38) High School Hustle (09:26) College Chaos And Crash (11:49) Rain Means Change (14:09) County Jail Reality (17:06) Sponsor Break Roka (19:43) Denied Then Navy Shot (22:56) BUDS Cold And Hell Week (29:26) Darkest Conditioning Runs (30:26) Running Form and Gait (31:54) Marathon Mindset Curse (33:03) Gobi Desert Stage Race (34:57) Skincare Ad Break (36:29) Joining SEAL Team 7 (37:19) Peer Evals and Rankings (38:18) Comms and JTAC Track (41:10) Sniper School and Stalking (45:10) Low Vis Intel Ops (46:54) Yemen Deployment Tension (48:56) Iraq Rockets and Base Build (52:32) Assault Charge Fallout (55:19) Court Deal in Boise (57:21) Paying Restitution Hard (57:48) Jail Then Back To Training (58:39) Probation In SEAL Life (01:00:13) Jimmy Buffett Golf Cart Bust (01:02:03) Steroid Test Career Fallout (01:06:22) Leaving Teams For Construction (01:07:27) Adderall Xanax Spiral (01:09:28) Opiates Return Then Fentanyl (01:12:32) High Functioning VC Hustle (01:16:07) Hawaii Withdrawal And Acid Ride (01:19:07) Homeless Suicidal Turning Point (01:23:03) One Way Ticket To Legion (01:24:43) Paris Hostels And Legion Gate (01:26:38) Passport Taken New Identity (01:27:23) Gate Shock Pullups Test (01:29:11) Barracks Vibes Recruit Types (01:30:34) Kenyan Runner Visa Hack (01:33:37) Gestapo Interviews Selection (01:36:32) Starting Over Cleaning Toilets (01:38:04) French Guiana Jungle Ops (01:40:39) Ukraine War Estonia Deployment (01:44:48) Barracks Fights Discipline (01:49:36) Legion Running Culture (01:52:34) Amazon Survival Gold Mines (01:55:19) Gold Flakes Oil Bugs (01:56:11) Amazon Jungle Hellscape (01:57:11) Thriving in Humidity (02:00:13) Running Shoes and Boots (02:01:57) Social Media Sparks Exit (02:12:32) Discipline and Agency (02:18:00) Coaching and Consistency (02:23:33) Closing Thanks and Plugs Learn more about your ad choices. Visit megaphone.fm/adchoices

  11. 68

    Four Brain Surgeries, Total Deafness, and Refusing to Break | McKinnon Galloway

    McKinnon Galloway was diagnosed with NF2 at 16 after a routine MRI for a volleyball concussion revealed two brain tumors. What followed was years of chemotherapy, a phase-one clinical trial, four brain surgeries, radiation, facial paralysis, a cerebral stroke, and the complete loss of her hearing. Her third brain surgery became life-threatening when doctors discovered that her tumor had developed an extensive blood supply. McKinnon nearly bled out, woke up fully deaf, and learned that complications had prevented surgeons from placing the auditory brain implant she expected to receive. Months later, another surgery left her struggling to walk and unable to move one side of her face. McKinnon also opens up about her father’s alcoholism and suicide, the strength she inherited from her mother, the realities of navigating healthcare and insurance, and the daily isolation that can come with deafness. Rather than disappearing into everything she lost, McKinnon built a platform that bridges the deaf and hearing worlds. Now followed by more than one million people across social media, she advocates for better deaf technology, clearer patient communication, and a more personal approach to medicine through her mission of “Humanizing Healthcare.” Follow McKinnon on Instagram: @mckinnongalloway Thank you to our sponsors Our Title Sponsor ROKA: www.roka.com/ Code “RIDEOUT” AMP Fitness: amp.ai/rideout  Ken’s book now available here: https://www.theothersideofhard.com/ Chapters (00:00) Meet McKinnon (00:48) Living With NF2 (02:26) Growing Up Charlotte (04:20) Diagnosis At Sixteen (05:44) First Brain Surgery (08:16) Recovery And Questions (10:30) Roka Eyewear Sponsor (12:15) Costa Rica Sea Turtles (13:42) College And Family Strain (15:34) Trials Second Surgery (18:14) Losing Hearing Completely (20:55) Third Surgery Near Death (25:09) Deafness And Implants (27:08) Post Op Complications (30:56) Surgery Complications (32:54) Sponsor Break Amp (33:39) Mom Teaches Independence (35:37) Dad Addiction Spiral (40:55) Losing Her Father (45:03) Faith Trip Bethlehem (47:46) Radiation And Recovery (53:29) MRI Scare And Boston (57:20) Living With NF2 (59:51) Marriage And Work Talk (01:00:50) Insurance Costs Reality (01:02:44) Ambulance Bill Fight (01:03:48) Fees Everywhere Now (01:05:14) Tipping Gone Wild (01:06:18) Driving While Deaf (01:07:43) Handicap Parking Clash (01:10:01) Hardest Part Socializing (01:11:48) Hope for Nerve Repair (01:13:20) Deaf Tech Advocacy (01:14:00) Social Media Origin Story (01:17:06) Handling Online Trolls (01:19:49) Perks of Being Deaf (01:24:14) Humanizing Healthcare Mission (01:26:49) Authentic Content Approach (01:28:53) Brand Deals and Contact (01:29:53) Daily Work and Pivots (01:31:02) Wrap Up and Subscribe Learn more about your ad choices. Visit megaphone.fm/adchoices

  12. 67

    A School Shooting, a Shipwreck, and the Long Run to Sobriety | Mishka Shubaly

    Mishka Shubaly has lived several lives: gifted student, touring musician, Columbia-trained writer, addict, shipwreck survivor, ultrarunner, Yale professor, and the editor who helped Ken Rideout turn his life into a book. Mishka joins Ken for a deeply personal conversation about growing up with a distant father, leaving home for college at 15, surviving a deadly school shooting, and watching his family lose everything shortly afterward. He recounts years of destructive drinking and drug use, getting shipwrecked in the Bahamas, walking for miles without food or navigation, and drinking his own urine shortly before being rescued. They also discuss the realization that finally pushed Mishka toward sobriety, the furious first run that changed his life, becoming an ultramarathoner, nearly joining a reality dating show, and how a cold email led Jeff Bezos to write the foreword to his book. Ken and Mishka reflect on addiction, anxiety, ambition, friendship, marriage, and the difficult process of believing that the life you have built might finally be enough. Thank you to our sponsors Our Title Sponsor ROKA: www.roka.com/ Code “RIDEOUT” Wild Roman: wildroman.com/rideout Code “RIDEOUT15” Ken’s book now available here: https://www.theothersideofhard.com/ Chapters (00:00) Mishka Joins the Show (00:44) Writing the Book Together (02:09) Authenticity Over Advice (03:57) Running Shoe Rabbit Hole (08:31) Frugal Life and Family Roots (12:48) Sponsor Break Roka Eyewear (14:24) Kids and Wastefulness (17:46) Sober Anxiety and Control (21:57) Ibogaine and Rewiring the Brain (23:29) Mishka’s Upbringing and Rocket Scientist Dad (27:34) Family Struggles and Parenting Reflections (32:42) Sponsor Break Wild Roman Skincare (33:46) Divorce Year and Dad Moves Away (34:39) Early College Leap (35:35) Fights and Trouble (36:02) Campus Shooting Trauma (38:29) Divorce and Downward Spiral (44:35) Addiction and New Perspective (48:50) Success and Enough (51:39) Family Pressure and Anxiety (57:36) From Acting to Writing (59:09) Dad Fallout and No Kids (01:03:46) New York and Columbia MFA (01:06:34) Playing It Cool (01:07:12) Celebrity Sauna Stories (01:09:31) Columbia Encouragement (01:11:40) Ivy League Aid Debate (01:13:33) Loans And Burnout (01:15:12) Music Life And Hoarding (01:18:39) Shipwreck Setup (01:22:06) Running Aground (01:25:30) Survival Walk Breakdown (01:30:44) Rescue And Aftermath (01:33:39) SEAL Prep Coincidence (01:35:46) Dating Show Tease (01:36:05) Reality Show Doubts (01:37:58) Dark Side of Reality TV (01:40:13) Lawyer Negotiation Tactics (01:42:20) Dodging the Dating Show (01:44:36) Sobriety Turning Point (01:48:49) First Furious Run (01:52:55) Ultra Lessons and New Highs (01:54:39) Kenya Stage Race Adventure (01:57:09) Love as the New Anchor (01:58:54) Withdrawal and Anxiety Hell (02:01:49) What’s Next Creatively (02:04:15) Bezos Foreword Story (02:06:44) Final Thanks and Subscribe Learn more about your ad choices. Visit megaphone.fm/adchoices

  13. 66

    One Life, Two Hearts: Surviving Cancer, Loss and Heart Failure | Dr. Dawn Mussallem

    Dr. Dawn Mussallem was a young medical student when she collapsed and doctors discovered a 15-centimeter tumor wrapped around her heart. She was diagnosed with stage IV diffuse large B-cell lymphoma and told she had only months to live. She endured chemotherapy, a bone marrow transplant and radiation while continuing medical school, eventually graduating first in her class. But surviving cancer came at another cost: the treatment severely damaged her heart. Dawn developed advanced heart failure, received a pacemaker and defibrillator, lost her husband to sudden cardiac death and spent years fighting to stay alive for her daughter. In 2021, with her organs beginning to fail, she accepted a donor heart from a woman who had used intravenous drugs and carried hepatitis C. That transplant gave Dawn a second life. Now an integrative oncologist, endurance athlete and Chief Medical Officer at Fountain Life, Dawn joins Ken Rideout to share what she learned through cancer, grief, heart failure and transplantation. They also discuss the fundamentals of longevity that matter most, including fiber, complex carbohydrates, strength training, VO2 max, heart-disease screening, organ donation and the role of nutrition in cancer survivorship. This is a story about accepting what you cannot control, refusing to surrender your purpose and making every day of a borrowed life count. Thank you to our sponsors Our Title Sponsor ROKA: www.roka.com/ Code “RIDEOUT” AMP Fitness: amp.ai/rideout  Ken’s book now available here: https://www.theothersideofhard.com/ Chapters (00:00) Meet Dr Dawn (01:11) Ohio Roots and Early Running (02:35) Raising Healthy Kids (06:05) Athletics and Strength Training (09:15) College Fitness and Ms Fitness (10:41) Sponsor Break Roka Eyewear (12:22) Carbs Fiber and Performance (19:26) Path to Medicine and Mayo (23:21) Cancer Diagnosis and Survival (31:18) Chemo And Transplant (32:08) Hospital Bike Breakthrough (33:14) Exercise As Medicine (34:18) Transplant Process Explained (35:17) Isolation And Infection Control (36:26) Radiation And Tumor Limits (37:29) Heart Failure After Cancer (38:39) Fertility And IVF Struggles (41:07) Surprise Pregnancy Discovery (43:40) Postpartum Heart Failure Reveal (46:25) Diagnosis And Mayo Recovery (48:57) Devices And HRV Talk (50:36) Fountain Life Heart Data (53:44) Lifestyle And VO2 Priority (57:31) Precision Genomics Testing (01:01:32) Next Gen Lipid Drugs (01:02:16) Metabolic And Inflammation Tests (01:04:37) Loss And Resilience (01:07:21) Diet For Heart Reversal (01:10:35) Near Death And Transplant Listing (01:15:51) Donor Heart Dilemma (01:19:55) Transplant Recovery And Gratitude (01:23:35) Integrative Oncology Explained (01:26:05) Insurance And Breast Cancer Care (01:28:04) Hormone Blockers And Symptom Relief (01:32:09) Closing And Subscribe Learn more about your ad choices. Visit megaphone.fm/adchoices

  14. 65

    Rejected TV Pitch to the World’s Wildest Animal Encounters | Mark Vins

    Mark Vins is the co-founder and host of Brave Wilderness, one of the biggest wildlife channels on YouTube. Mark joins Ken to explain how a rejected television concept became a global media brand, why a video featuring the “cow killer” velvet ant gained hundreds of thousands of subscribers in a single day, and what it actually feels like to be stung by a murder hornet, bitten by a giant centipede, and envenomated by some of the world’s most painful creatures. He shares the safety protocols behind the videos, the risks of anaphylaxis, the physical toll of spending nearly 300 days a year traveling, and the lessons Brave Wilderness learned after entering the Hollywood and television system. Mark also takes Ken behind the scenes of filming mountain gorillas alongside armed rangers in the Democratic Republic of the Congo and making his first feature documentary, Reef to Ridge, in the Galápagos. The film follows the ecosystem from the ocean floor to the summit of Wolf Volcano, where fewer than 300 rare pink iguanas remain. This is the story of turning childhood exploration into a global wildlife platform—and using viral entertainment to bring millions of people closer to the natural world. Thank you to our sponsors Our Title Sponsor ROKA: www.roka.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 Mark Vins (00:46) What Is Brave Wilderness (01:44) Ohio Roots And Tennis (03:09) Film School And Early Hustle (05:20) From TV Rejection To YouTube (09:07) Sting Videos Go Viral (12:03) Sponsor Break Roka(13:43) Cow Killer Explained (16:34) Filming The Sting Safely (19:30) Anaphylaxis And EpiPens (26:46) Travel Life And Costa Rica (29:13) Poison Frogs And Toxins (32:59) Snakebites And Deadliest Snakes (37:12) Terrifying Cave Diving (38:13) Focus Supplement Ad (38:59) Hollywood Agency Lessons(45:47) Venom Basics Explained (47:04) Murder Hornet Nightmare (52:56) Centipede Bloodbath (56:42) Scorpions Fish and Fireworms (01:04:36) Gorillas and Ranger Risks (01:13:44) Rangers Fitness Talk (01:13:50) Favorite Trips Japan (01:14:42) Galapagos Feature Reveal (01:16:29) Wolf Volcano Expedition (01:17:51) Sharks And Finning (01:21:33) Dehydration Survival Stories (01:24:02) Pink Iguana Deep Dive (01:25:25) Volcano Tourism Risks (01:28:30) Peruvian Amazon Off Grid (01:30:49) Sandflies And Leishmaniasis (01:33:45) Global Wildlife Hotspots (01:35:27) Predators And Mountain Lions (01:42:04) Future Films And Running (01:45:13) Bee Swarms And Safety (01:48:05) Final Thanks And Subscribe Learn more about your ad choices. Visit megaphone.fm/adchoices

  15. 64

    The Brutal Road to a Tour de France Top 10 | Andrew Talansky

    Andrew Talansky didn’t get on a road bike until he was 17. Seven years later, he finished 10th overall in the Tour de France. Andrew joins Ken Rideout to tell the story of his unlikely rise from getting dropped on Miami group rides to competing against the best cyclists in the world. He shares how a running injury led him to cycling, why he left college to chase the sport, and how a brutal experience living and racing in Italy nearly ended his career before it truly began. Andrew also takes Ken inside the realities of professional cycling: training with Levi Leipheimer, exchanging words with Lance Armstrong during his breakout ride at the Tour of the Gila, receiving offers from the world’s top teams, and entering the sport as it tried to rebuild trust after the doping era. He explains why even elite amateur cyclists cannot comprehend the level of the Tour de France, what it feels like to descend at highway speeds in a crowded peloton, how riders recover and survive for three straight weeks, and why Alpe d’Huez became his favorite climb while Mont Ventoux became his hardest. Andrew also reflects on winning the Critérium du Dauphiné, walking away from professional cycling while still in his prime, the burnout and missing support that influenced his retirement, and how those experiences now shape his work helping athletes and organizations build healthier high-performance environments. Thank you to our sponsors Our Title Sponsor ROKA: www.roka.com/ Code “RIDEOUT” Timeline: timeline.com/rideout Code “RIDEOUT” Ken’s book now available here: https://www.theothersideofhard.com/ Chapters (00:00) Meet Andrew Talansky (00:13) Miami Cycling Roots (02:01) From Running To Bikes (03:45) Gear And Community Support (06:29) Tour Dreams And Fast Progress (08:57) The Real Pro Gap (13:38) Tour Chaos And Crashes (15:52) Risky Descents And Training (20:26) Winning Juniors And Nationals (23:35) Europe Reality Check (26:34) Cal Giant Breakthrough (33:37) Lance Moment At Gila (36:16) WorldTour Offers Roll In (36:32) National Champ Group Ride (37:41) Body Types and Weight (38:08) Doping and Eating Culture (39:47) Blood Doping Reality (41:10) Why Doping Felt Normal (42:52) Racing Clean After Lance (45:10) Joining Slipstream in Italy (46:52) Neo Pro Lessons and TT Talent (48:11) First Pro Race Breakthrough (49:40) First Grand Tour Vuelta (50:35) Olympic Deal Rumors (53:09) First WorldTour Win (56:27) First Tour de France Spotlight (59:55) Equipment and Team Specs (01:02:38) Tour Results and Final Day Rules (01:04:39) Peloton Sportsmanship and Cars (01:08:03) Alpe d’Huez Memories (01:09:06) Crowds Gone Too Far (01:12:43) Team Radio Tactics (01:14:26) Domestiques And Bottles (01:15:14) Hardest Climb Ventoux (01:16:01) Post Stage Recovery Routine (01:19:01) Tour Hotels And Logistics (01:22:10) Malibu Riding Stories (01:27:22) Burnout And Retirement (01:29:46) Dauphine Win Chaos (01:32:04) Cobbles And Roubaix Fear (01:34:40) Triathlon Reality Check (01:37:46) Performance Coaching Today (01:39:40) Wrap Up And Subscribe Learn more about your ad choices. Visit megaphone.fm/adchoices

  16. 63

    From Bartender to Elite MMA Coach | Eric Nicksick

    Eric Nicksick never planned on becoming one of the most respected coaches in MMA. He grew up in Las Vegas surrounded by football coaches, learning how to study film, lead a team, master the fundamentals, and separate himself through what Randy Couture later called “things that take no talent”: being early, being prepared, and doing the work. After football, Eric walked into Xtreme Couture before the gym had officially opened. He trained with world-class fighters, became its first paying member, and kept showing up. When Randy Couture asked him to run a single grappling class, Eric said yes. That class grew into a coaching career. Today, Eric has coached UFC champions Francis Ngannou and Sean Strickland and helped build one of MMA’s most respected teams. In this conversation, Eric shares how he learned striking from Ray Sefo, strategy from Randy Couture, and cornering through years of saying yes to every opportunity. He opens up about the danger fighters face, why young athletes need a life beyond competition, how he handles Sean Strickland’s intensity, and the trust he built with Francis Ngannou while helping him confront the wrestling and fear left behind by his first fight with Stipe Miocic. Eric also explains how his friendship with Boston Celtics head coach Joe Mazzulla has changed the way both men think about leadership, preparation, and coaching at the highest level.  Thank you to our sponsors Our Title Sponsor ROKA: www.roka.com/ Code “RIDEOUT” Wild Roman: wildroman.com/rideout Code “RIDEOUT15” Ken’s book now available here: https://www.theothersideofhard.com/ Chapters (00:00) Warm Welcome and Hats (01:24) Origin Story Setup (01:52) Football Roots in Vegas (03:02) College Ball and Talent Gaps (05:45) Film Study and Fundamentals (10:30) Leadership and Humility (11:42) Roka Eyewear Ad Break (13:22) First Steps in Combat Sports (15:30) Extreme Couture First Day (18:44) Accidental Coach to Gym Manager (23:28) Learning Striking from Ray Sefo (26:38) Cage Geography Traps (27:45) Tape Study Coaching Edge (28:27) Imposter Syndrome Path (30:18) Learning to Corner (32:06) Saying Yes for Reps (33:41) Big Stage Gratitude (36:19) Skincare Ad Break (37:19) Bad Knockouts Aftermath (38:38) Backup Plans Identity (45:10) Coaching Sean Strickland (49:58) Locker Room Boundaries (50:32) Sparring Intensity Control (52:33) Gym Visitor Etiquette (54:25) Bar Guy Reality Check (56:04) Gym Trash Talk Payback (57:45) Francis Origin Story (59:53) Fear After Stipe Loss (01:02:26) Building Wrestling Confidence (01:06:08) Wild Sparring Partners (01:07:38) Trust and Family Bond (01:11:00) Culture and Gratitude Lessons (01:13:56) Travel and Perspective (01:15:47) Coaching With Joe Mazzulla (01:20:28) Wrap Up and Subscribe Learn more about your ad choices. Visit megaphone.fm/adchoices

  17. 62

    From $1 Paychecks to World Champion | Regis Prograis

    Two-time world champion Regis "Rougarou" Prograis built his career the hard way. He started boxing late, lost everything when Hurricane Katrina destroyed his family's home, sold tickets to fund his early professional career, and eventually fought his way to the top of the sport, becoming a two-time world champion. But behind the belts was a very different story. Regis opens up about paying opponents just to get fights, rebuilding his life after Katrina, career-threatening injuries, management battles, devastating losses, and why he knew his career was coming to an end long before he officially retired. Most importantly, he shares something few elite fighters ever admit: before his final fight against Conor Benn, he didn't want to step into the ring. He was scared, mentally exhausted, and hoping something would happen so he wouldn't have to fight. Instead, he walked anyway. In this conversation, Regis explains why facing that fear ultimately gave him the peace to leave boxing on his own terms. Thank you to our sponsors Our Title Sponsor ROKA: www.roka.com/ Code “RIDEOUT” AMP Fitness: amp.ai/rideout  Ken’s book now available here: https://www.theothersideofhard.com/ Chapters (00:00) Regis Joins the Show (00:24) Retirement and New Combat Plans (01:17) Leaving Boxing on His Terms (02:30) Business Moves After Fighting (04:06) New Orleans Roots and Early Sports (04:53) From Karate to Boxing (08:02) Red Dog Yard Gym Lessons (12:50) Sponsor Break Roka Eyewear (14:30) Katrina and Losing Everything (17:48) Starting Over in Houston (21:11) Savannah Gym and Elite Talent (27:50) Amateur Grind and Confidence (30:40) Sponsor Break Amp Training (31:16) Paying for Tournaments and Jobs (32:41) Family Background and Basketball Love (33:18) Meeting Allen Iverson (34:59) NBA Giants Up Close (35:39) Turning Pro And Paying Opponents (36:50) Ticket Sales Dollar Checks (39:11) Signing With Lou DiBella (40:26) ShoBox Knockout Run (41:54) Eye Injury And Going Broke (47:09) Big Win Joel Diaz Payday (49:22) New Management Wahlberg Berg (53:09) Indongo Statement Win (54:58) World Super Series Explained (57:09) Josh Taylor Fight Setup (58:23) UK Media Mind Games (01:00:49) Fight Night Crowd Influence (01:03:04) Judges And Close Calls (01:04:24) Taylor Confidence And Respect (01:08:07) Life After The Loss (01:11:08) Pandemic And Boxing Purgatory (01:14:40) Back To Champion Status (01:15:41) Movies With Peter (01:21:15) Manager Drama And Lawsuit (01:25:27) Matchroom And Style Adjustments (01:26:33) Haney Loss And Camp Distractions (01:33:33) Aftermath And Catterall Setup (01:35:49) Dropped and Injured (01:36:19) Respect for Catterall (01:36:49) Why Fight in UK (01:37:21) Manager Drama and Bad Deal (01:38:37) Injuries and Decline Signs (01:39:53) Vegas Reset and No Contracts (01:40:51) Conor Benn Netflix Stage (01:41:57) Camp Burnout and Doubt (01:44:07) Fight Day Fear to Switch On (01:49:18) Lessons from the Loss (01:54:34) Peace After Retirement (01:57:29) New Ventures and Businesses (01:58:57) Kids Summer and Fatherhood (01:59:40) Rougarou Mask Memories (02:01:39) Raising Kids Without Pressure (02:03:38) Old School Training Gear (02:04:30) Farewell and Subscribe Learn more about your ad choices. Visit megaphone.fm/adchoices

  18. 61

    He Started Running in College—Then Made Five Olympic Teams | Abdi Abdirahman

    Abdi Abdirahman arrived in the United States as a refugee from Somalia in 1990. He spoke no English, settled with his family in Tucson, Arizona, and went through high school without ever competing as a runner. He did not discover the sport until his sophomore year at Pima Community College. Abdi showed up to his first practice wearing jeans and boots. Despite having no formal training, he finished second on the team. One week later, he ran 15:05 and won the 5,000 meters in his first track meet. That unexpected beginning launched one of the most remarkable careers in American distance running. Abdi became a four-time U.S. champion in the 10,000 meters and represented the United States at five Olympic Games across more than two decades. At 43, he finished third at the 2020 U.S. Olympic Marathon Trials and qualified for his fifth Olympic team. He also became the oldest male runner to reach the podium at the New York City Marathon. In this conversation, Abdi shares the story of leaving Somalia during civil war, adjusting to life in America, accidentally discovering his talent, racing legends like Meb Keflezighi and Haile Gebrselassie, and building a professional career that lasted far longer than almost anyone expected. He also opens up about the business behind professional running, the evolution of marathon training and super shoes, making money through prize purses and appearance fees, and why experience becomes so important over 26.2 miles. Today, Abdi divides his time between Tucson and Ethiopia, where he helps coach and mentor the next generation of elite runners. This is a conversation about talent, longevity, humility, and continuing to show up long after other people think your opportunity has passed. Thank you to our sponsors Our Title Sponsor ROKA: www.roka.com/ Code “RIDEOUT” Timeline: timeline.com/rideout Code “RIDEOUT” Ken’s book now available here: https://www.theothersideofhard.com/ Chapters (00:00) Welcome Abdi (01:07) Somalia to Tucson (02:15) Starting Running Late (04:01) Jeans and Boots Debut (06:16) Scholarship to Arizona (08:26) Somalia Childhood (10:17) Sponsor Break (11:55) NCAA to Pro Life (13:11) Olympics and Selection (16:39) Masters Mindset (20:08) Shoe Deals and Money (23:58) Ethiopia and Altitude (27:12) Career Highlights (30:11) Training and Workouts (35:40) Boston 2018 Survival (36:52) Mitochondria Ad Read (37:19) Mitochondria Support Plug (38:25) Cold Rainy Race Start (39:49) Favorite Races Debate (40:44) Marathon Pacing Lessons (45:35) Fueling And Gel Evolution (47:30) Ultras And Recovery Runs (51:03) Biggest Wins And Coaches (54:44) Ethiopia Camp And Rivalries (59:10) Shoe Deals And Super Shoes (01:09:38) Community Book And Farewell Learn more about your ad choices. Visit megaphone.fm/adchoices

  19. 60

    From Army Airborne to Addiction Recovery | Evan Slaughter

    Evan Slaughter grew up in Birmingham, Alabama in a conservative household before addiction changed the course of his life. After battling an early OxyContin addiction and completing rehab, he joined the U.S. Army, earned an Airborne contract, deployed to Afghanistan, and was injured in an IED blast. The pain medication prescribed after that injury pulled him back into addiction. What followed were years of PTSD, arrests, multiple rehabs, and trying to rebuild a life that kept slipping away. Everything changed in 2021. Today, Evan is better known as Fit2Serve, creating comedy videos seen by millions while using humor, honesty, and his own story to help others find hope. His viral skits may make people laugh, but the road that led there was anything but funny. In this conversation, Evan shares his father's addiction, his own battle with OxyContin, Army Airborne school, Afghanistan, PTSD, Veterans Court, recovery, psychedelics, purpose, and why "Fit to Serve" no longer means physical fitness—it means being equipped to serve others. Thank you to our sponsors Our Title Sponsor ROKA: www.roka.com/ Code “RIDEOUT” Wild Roman: wildroman.com/rideout Code “RIDEOUT15” Ken’s book now available here: https://www.theothersideofhard.com/ Chapters (00:00) Meet Evan Slaughter (00:40) Growing Up Alabama (01:12) Church Life and Family Upheaval (01:50) Dad’s Addiction and Recovery (05:56) Finding Comedy Early (06:37) Stand-Up Dreams and Fear (12:38) Alpha Dad Skits and Garage Gym (14:30) Sponsor Break Roka (16:11) School Sports and College Detour (19:02) Lifting and Bench Press Talk (31:11) Sponsor Break Wild Roman (32:34) Dropping Out and Training Career (34:17) OxyContin Addiction and Rehab (37:01) Rehab to Enlistment (38:17) Choosing Army Infantry (39:40) Earning 18X Contract (41:41) Airborne School Basics (44:03) First Jump Nerves (46:56) Hard Landings and Mishaps (49:18) Afghanistan IED Blast (53:48) Pain Pills Spiral (56:38) PTSD and Coming Home (58:34) Pharmacy Sting Arrest (01:01:56) Veterans Court and Rehab (01:04:44) TikTok Breakthrough (01:09:03) Staying Sober and Creating (01:10:28) Influencer Advice and Work (01:12:36) Real Jobs Before Social (01:13:53) Time Value Mindset (01:15:28) Psychedelics For Recovery (01:20:28) DMT Lessons And Integration (01:24:10) Money Doesn't Fix Pain (01:26:51) Motorcycle And Simple Joys (01:30:53) Pickleball And Community (01:34:17) Fit To Serve Meaning (01:38:08) Nashville Move And Friends (01:39:00) Brand Deals Strategy (01:44:24) Wrap Up And Where To Find (01:46:16) Podcast Outro And Sponsors Learn more about your ad choices. Visit megaphone.fm/adchoices

  20. 59

    He Barely Played in College. Then Played 14 NFL Seasons. | Matt Cassel

    Matt Cassel's football story shouldn't have happened. He spent his college career at USC backing up two Heisman Trophy winners, Carson Palmer and Matt Leinart, throwing just a handful of passes while wondering if he'd ever get a real opportunity. Most players would have transferred. Matt stayed ready. That decision changed his life. After being drafted by the New England Patriots, he learned behind Tom Brady until Brady suffered a season-ending injury in Week 1 of 2008. Overnight, Cassel went from anonymous backup to starting quarterback of one of the most scrutinized teams in sports. He led New England to an 11-5 season, earned a franchise tag, signed a $63 million contract, and went on to play 14 seasons in the NFL. In this conversation, Matt shares what he learned from Tom Brady and Bill Belichick, the pressure of replacing the greatest quarterback of all time, overcoming years without playing, navigating trades, injuries, personal loss, and why being ready before your opportunity arrives changed everything. Thank you to our sponsors Our Title Sponsor ROKA: www.roka.com/ Code “RIDEOUT” AMP Fitness: amp.ai/rideout  Ken’s book now available here: https://www.theothersideofhard.com/ Chapters 00:00) Meet Matt Cassel (00:22) Dad Life and Flag Football (02:00) Leaving LA for Nashville (04:01) Growing Up and Playing Both Ways (05:01) Quarterback Jumps in Speed (07:40) NFL Film Study and Prep (08:32) Sponsor Break Roka (10:45) USC Teammates and Practice Wars (12:59) Tom Brady as Mentor (14:03) Stuck Behind Heisman Winners (16:46) Tight End Detour and Baseball Reset (18:24) Owen Hanson and Prison Reality (20:58) Pro Day and Wonderlic Chaos (24:33) Reading Defenses Like Chess (26:27) Randy Moss Freak Talent (27:49) Standing Tall in the Pocket (31:59) Formation Tricks and Counters (34:25) Sponsor Break Amp Training (35:28) Pro Day Lights Out to Draft Buzz (37:55) Selling the Backup Story (39:16) Finding an Agent (42:08) NFL Workouts Breakdown (43:55) Belichick Draft Call (46:23) Draft Day Celebration (49:48) Rookie Arrival in Foxborough (53:21) Patriots Culture Shock (56:22) Rookie Pay and Perks (59:51) Family and Dad’s Struggles (01:02:08) Dad’s Death During Season (01:05:59) Rookie Hazing and Dinner (01:11:53) Learning from Brady (01:13:07) Brady Work Ethic (01:13:56) Quarterback Perfection (01:15:44) Brady Injury Moment (01:17:10) Thrown Into Action (01:18:40) Bomb To Moss (01:19:52) Overnight Spotlight (01:22:29) Media And Sponsors (01:25:31) First Start Vs Jets (01:27:23) Brady Off Field Kindness (01:30:08) Franchise Tag Shock (01:33:30) Trade And Big Deal (01:36:00) New Life In KC (01:38:22) Coordinator Quits Chaos (01:43:38) Pressure And Mindset (01:47:05) Chiefs Turnaround (01:49:02) Appendix Emergency (01:51:21) Playing Post Surgery (01:52:34) Bernard Pollard Stories (01:55:26) Minnesota And London Start (01:58:01) Bridgewater Mentorship (01:59:29) Foot Injury Nightmare (02:04:36) Traded To Dallas Chaos (02:07:50) Cowboys Culture Shock (02:09:15) Facilities And Gear (02:13:12) Game Balls And Deflategate (02:20:28) Life After Football (02:23:24) Final Thanks And Outro Learn more about your ad choices. Visit megaphone.fm/adchoices

  21. 58

    The Olympian Who Nearly Died Making Weight | Danny O'Connor

    Danny O'Connor looked like he had everything. A state wrestling champion. An Olympian. One of the top professional boxers in America with a world title shot finally within reach. Behind the scenes, almost nobody knew he had been battling an eating disorder for years. What began as extreme weight cutting in high school wrestling evolved into a life-threatening cycle of starvation, binge eating, dehydration, and dangerous weight cuts that nearly cost him everything. Before the biggest fight of his career, Danny collapsed while trying to make weight, was rushed to the ICU, and watched his dream of becoming world champion disappear. In this conversation, Danny opens up about growing up in Massachusetts, dropping out of school, turning his life around through boxing, making the U.S. Olympic team, the hidden reality of weight-class sports, and the long road to recovering from an eating disorder that almost killed him. This is a conversation about obsession, identity, recovery, and learning that the toughest opponent isn't always standing across the ring. Thank you to our sponsors Our Title Sponsor ROKA: www.roka.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 Danny O'Connor (00:43) Growing Up in Sports (01:43) Wrestling Found His Calling (04:14) Weight Cutting Obsession (06:14) Laxatives and Hidden Suffering (08:47) Grades Collapse and Dropping Out (10:54) Arrests and Losing Control (21:40) Court Wake Up Call (23:53) Boxing Saves His Life (27:15) Golden Gloves to Olympic Dream (29:59) Defensive Style and Sparring (33:06) Olympic Trials Outsider (34:01) Sponsor Break Athletic Nicotine (34:45) Trials Heartbreak (35:36) Beating Future Gold (37:11) Beijing Team Breakdown (38:33) Turning Pro Decision (39:48) Weight Cutting vs Disorder (43:20) Gym Hops and Undefeated Run (44:29) First Loss and Texas Move (48:31) Binge Eating Reality (53:20) Daily Yo-Yo Chaos (56:11) Missing Weight Fallout (01:03:41) WBC Shot in Fresno (01:05:43) Urges and Survival Hacks (01:09:07) Binge Spiral at Home (01:10:02) Stepping Away for Help (01:12:02) Learning Recovery Tools (01:14:16) Relapse in Training Camp (01:16:23) Weigh In Day Collapse (01:21:37) Aftermath and Perspective Shift (01:26:28) Specialized Treatment Begins (01:30:31) Freedom and Maintenance (01:35:50) Advice and Raising Awareness (01:39:04) Book Plug and Closing (01:41:12) Podcast Outro and Sponsors Learn more about your ad choices. Visit megaphone.fm/adchoices

  22. 57

    Boston, Addiction, The Town, 12 Years Sober | George Carroll “Slaine”

    He taught himself to rap at nine years old, co-founded the rap supergroup La Coka Nostra, got discovered by Ben Affleck for Gone Baby Gone, and went on to act in The Town, Killing Them Softly, and Joker. What almost nobody saw was what was happening behind the scenes. For 23 years Slaine battled alcohol and addiction, through cocaine, OxyContin, and heroin, while chasing two careers most people told him were impossible. It cost him his marriage, his home, and nearly his life, until the only thing that finally outweighed the addiction was the fear of losing his son. In this conversation, Slaine opens up about growing up in the chaos of Boston, the drug culture that swallowed his generation, the record deal he was smart enough to turn down, auditioning drunk for Ben Affleck, hitting rock bottom as a father, the phone call outside a bar that saved his life, getting sober on March 3, 2014, and building Charles River Recovery, a treatment center that has helped more than 7,500 people. This is a conversation about identity, addiction, redemption, and giving it away to keep it. Thank you to our sponsors Our Title Sponsor ROKA: www.roka.com Code “RIDEOUT” Wild Roman: wildroman.com/rideout Code “RIDEOUT15” Ken’s book now available here: https://www.theothersideofhard.com/ Chapters (00:00) Meet Slaine (02:00) Boston Neighborhood Chaos (04:10) Childhood Trauma Unpacked (05:00) Fatherhood And Hindsight (08:23) First Drink Relief (09:42) Cocaine The Cheat Code (11:48) Eyewear Ad Break (13:20) Crabs In A Bucket (16:40) OxyContin Epidemic Boston (18:50) Film School Outsider (20:00) Boston Hardens You (24:50) ADHD As A Superpower (28:00) NYC Underground Comeup (31:31) Skincare Ad Break (34:48) The Deal He Refused (39:00) Squatting In A Warehouse (41:30) La Coka Nostra Born (44:00) 13,000 CDs Sold (46:00) Herald Story Affleck Calls (48:00) Drunk Audition For Affleck (51:56) Cleaned Up For Set (53:40) Prime Rib And A Warehouse (56:15) Boston Film Tax Credit (58:00) Vision Board Comes Alive (01:01:00) It All Hits At Once (01:15:45) Losing Everything (01:20:52) Failing As A Father (01:24:10) The Day It Stuck (01:26:57) The News That Should Have Broken Him (01:28:04) The Call Outside The Bar (01:30:00) Learning Humility (01:33:00) Uncle George (01:34:40) The One Belief (01:42:53) Building Charles River Recovery (01:48:20) Don’t Fit In A Box (01:51:15) How To Get Help (01:52:47) Farewell And Subscribe Learn more about your ad choices. Visit megaphone.fm/adchoices

  23. 56

    He Fought for a World Title with Lyme Disease | Mike Lee

    He graduated from Notre Dame, signed with Top Rank, fought at Madison Square Garden and Cowboys Stadium, starred in national Subway commercials, and earned a shot at a world title. What almost nobody saw was what was happening behind the scenes. For years Mike battled chronic pain, autoimmune disease, misdiagnoses, and Lyme disease while trying to keep his career alive. He fought through broken ribs, endless medications, and training camps where his body was telling him to stop long before his mind would listen. In this conversation, Mike opens up about growing up in Chicago, the pressure to make his father proud, becoming one of boxing's top contenders, the relief that came after his only professional loss, finding purpose beyond the ring, and why he now believes health is the greatest fight of all. This is a conversation about identity, resilience, and knowing when enough is enough. Thank you to our sponsors Wild Roman: wildroman.com/rideout Code “RIDEOUT15” Timeline: timeline.com/rideout Code “RIDEOUT” Ken’s book now available here: https://www.theothersideofhard.com/ Chapters (00:00) Meet Mike Lee (00:24) Subway Sponsorship Story (02:05) Chicago Roots Boxing Start (03:43) Notre Dame Bengal Bouts (04:35) Golden Gloves Breakthrough (06:18) Dad Pressure Motivation (08:18) Broken Rib Hospital Night (10:13) Caleb Plant Fight Setup (11:28) Weight Cut Autoimmune Struggles (14:27) Fight Stoppage Relief (17:29) Skincare Ad Break (18:53) Career Perspective Big Moments (20:49) Cowboys Stadium Jerry Jones (24:11) Why Fighting Captivates (25:07) Turning Pro With Top Rank (26:56) Early Pro Opponents (27:32) Target on My Back (27:59) Grooming vs Real Threats (29:46) UFC Losses vs Boxing (31:16) Money and Corruption (32:27) Why Losses Matter (34:57) Top Rank Lion’s Den (36:25) Spence Crawford Aftermath (38:48) Gym Culture and Identity (45:50) Reading Fighters on the Bag (47:11) Mitochondria Ad Break (49:58) Fatigue and Quiet Quitting (54:46) Life After the Spotlight (57:47) Lyme Misdiagnosis Journey (59:25) Hospital Rock Bottom (59:56) Functional Medicine Pivot (01:00:37) Comeback Fight Hollow Win (01:01:36) Opioids to Cannabinoids (01:02:29) Soul CBD vs THC Brand (01:03:35) Hemp Ban and Lobbying (01:08:15) Alcohol vs Cannabis Shift (01:13:36) Edibles Safety and Dosing (01:17:34) Pivoting Beyond Hemp (01:19:50) Kids Online and AI Future (01:28:40) Farewell and Subscribe Learn more about your ad choices. Visit megaphone.fm/adchoices

  24. 55

    The Crack Addict Who Became a Med Student | David Millar

    David Millar grew up at the Jersey Shore surrounded by addiction, promising himself he would never become like the people he watched struggle around him. Instead, by age 20, he was deep into alcohol, cocaine, and crack addiction. He dropped out of college, cycled through psych wards, detox centers, and rehabs, slept in the woods, stole to survive, and believed drugs would define the rest of his life. Then everything changed. David got sober, rebuilt his life one day at a time, rediscovered running, returned to school, and eventually earned acceptance into medical school despite being told his past would hold him back. Today, he is seven years sober, an ultrarunner, medical student, coach, and one of the most powerful voices in recovery. In this conversation, David shares the reality of addiction, life inside psych wards, sleeping in the woods, the treatment program that saved him, why running became his medicine, and how he transformed an addictive personality into a force for growth. This is a conversation about addiction, recovery, discipline, and what becomes possible when you refuse to quit. Thank you to our sponsors Athletic Nicotine: https://athleticnicotine.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 David Millar (00:47) Running Discipline Talk (02:27) Roka Eyewear Sponsor (03:56) Beach Town Upbringing (05:23) First Drink Turning Point (08:52) Fentanyl Reality Check (11:22) Running and Recovery (12:08) College Dropout Spiral (13:32) Cross Country Comeback (15:17) Athletic Nicotine Sponsor (15:52) Cocaine at Sixteen (20:42) Work Ethic Over Talent (24:31) Nursing School Collapse (26:57) Homeless in the Woods (28:51) Stealing To Survive (29:26) Florida Detox Escape (30:59) Detox System Gaming (31:40) Sponsor Break NAD Plus (32:46) First Psych Ward Hold (35:50) Locked Ward Reality (37:48) Coke To Crack Shift (40:00) Stimulants And Meth Talk (41:01) Recovery Spark At 20 (43:39) LA Boot Camp Sober Living (46:55) Accountability Culture (51:32) Early Sobriety Pain (54:18) Sobriety Mindset Shift (55:21) Addictive Drive Reframed (57:01) Back to School Sober (01:00:01) Pre Med Leap and MCAT (01:01:12) Hiding Recovery to Get In (01:03:07) Sober Edge in Med School (01:05:06) Rotations and Daily Grind (01:06:34) Training While Studying (01:08:28) Choosing a Specialty (01:09:26) Alcohol Guidelines Critique (01:11:25) Treat Addiction Not Symptoms (01:13:58) Subutex and Vivitrol Path (01:17:32) GLP Drugs and Cravings (01:18:59) Fitness and Running as Medicine (01:22:46) Closing Thanks and Where to Find Him (01:24:08) Subscribe Sponsors and Book Learn more about your ad choices. Visit megaphone.fm/adchoices

  25. 54

    From Tour Wins to Barely Holding a Club | Scott Stallings

    Scott Stallings is one of the fittest players to ever walk the PGA Tour. He grew up between Worcester, Massachusetts and Oak Ridge, Tennessee, walked on at Tennessee Tech after the program he dreamed of passed on him, and turned himself into a three-time PGA Tour winner over a fourteen-year career. Then, at the 2024 Players Championship, one swing into the lip of a fairway bunker tore his shoulder and the nerve out of his elbow. Three surgeries in fourteen months followed. During a comeback round at eleven under, the nerve tore loose again and his hand went white on the green. Three different doctors gave him the same answer: the golf he knew how to play was over. In this conversation, Scott opens up about losing the identity he had built his life around, running the Boston Marathon to survive the rehab, getting humbled in occupational therapy, and a surgeon asking whether he wanted to hold his daughter’s hand walking down the aisle. We also talk about choosing his family over one more swing, hosting Knoxville’s Korn Ferry Tour event, training for 29029, playing alongside Tiger Woods, and what the other side of hard looks like when the thing that defined you is gone. One of the most honest conversations we’ve had. Thank you to our sponsors Rho Nutrition: https://rhonutrition.com/ Code “RIDEOUT” Ken’s book now available here: https://www.theothersideofhard.com/ Chapters (00:00) Meet Scott Stallings (00:14) Roots and Accents (01:34) Golf Beginnings (02:02) Tiger Spark Moment (03:20) Why Golf Connects (03:58) Speedgolf Explained (06:08) Growing the Game (08:22) Late Bloomer Path (11:36) Tour Card Reality (13:52) Life on the Road (14:31) Never Off a Heater (19:43) Heater Ends Fast (20:38) Sponsor Break NAD (21:48) Money and Mindset (25:44) Winning Changes Everything (29:43) Imposter Syndrome Drive (32:11) Runner Mindset Parallels (35:46) Competitive Lens (36:34) Easy Days Discipline (37:06) Golf Injury Breakdown (38:36) Three Surgeries Rehab (40:39) Running Boston Goal (43:29) Boston Marathon Joy (47:45) Big Marathon Logistics (49:55) Return to Golf Plan (55:09) Elbow Setback Scare (58:49) Doctors End Career (01:02:53) Nerve Surgery Recovery (01:05:29) Identity Family Shift (01:06:54) Career Highlights Tiger (01:11:31) Majors Versus Regular (01:12:51) Major Prep Logistics (01:13:50) Slow Practice Rounds (01:15:44) Golf Course Fights (01:17:48) Fighting Levels and Jiu Jitsu (01:20:42) Weather Mental Edge (01:22:37) Memorial and Tiger Story (01:23:52) Tiger Crowd Etiquette (01:28:02) Tiger Trash Talk 67 (01:31:32) LIV and Golf Future (01:33:41) Walking Miles and Ultras (01:35:33) 29029 Training Tips (01:40:17) Sponsors and Next Steps (01:42:54) Closing and Subscribe Learn more about your ad choices. Visit megaphone.fm/adchoices

  26. 53

    He Played for the Celtics on OxyContin | Chris Herren

    Chris Herren grew up in Fall River, Massachusetts, a basketball city where making it meant everything. He earned a scholarship to Boston College, starred at Fresno State, and did what every kid in his hometown only dreamed of. He pulled on a Boston Celtics jersey. What almost no one knew was that he did it as an addict. Cocaine in college gave way to OxyContin and then heroin in the NBA. Chris played some of the biggest games of his life high, chasing his next fix between practices, until addiction cost him his career, his health, and nearly his family. In 2008, after years of running, Chris got sober, and he has stayed sober every day since. He founded The Herren Project and Herren Wellness, and now travels the country telling the truth about addiction to anyone who will listen. In this conversation, Chris opens up about growing up in Fall River, the secret he carried through the NBA, the night it all came apart, the moment his wife told him the truth, and what it means that his kids have never seen him high. This is a conversation about addiction, honesty, family, and the daily work of staying clean. Thank you to our sponsors Timeline: timeline.com/rideout Code “RIDEOUT” Ken’s book now available here: https://www.theothersideofhard.com/ Chapters (00:00) Meet Chris Herren (01:06) Fall River Roots (03:35) Basketball Junkie Book (08:58) How Addiction Began (13:04) BC to Fresno State (19:01) NBA Draft Journey (25:22) Welcome to the NBA (29:57) Trade to Celtics Dread (34:55) Shipping the stash (35:42) FedEx obsession in Dallas (36:38) Money gone and secrets (38:58) Dealer in Celtics uniform (42:33) Cut and Europe calls (43:28) Bologna withdrawal and heroin (54:38) Turkey hustle for dope (56:26) China forced sobriety relapse (01:02:42) Iran risks and taxi drops (01:06:49) Train crash to street life (01:08:49) Rock Bottom Checklist (01:10:21) Relief After Losing Everything (01:10:41) Overdoses Before Narcan (01:13:24) Nurse Intervention to Treatment (01:13:59) Daytop Program and Relapse (01:19:30) Recovery Structure That Worked (01:22:24) Rebuilding Through Coaching (01:24:10) Speaking and Service Mission (01:26:25) Holistic Rehab Model (01:28:28) Funding Scholarships and Donors (01:31:56) Family Healing and Milestones (01:34:30) Parenting and Sports Boundaries (01:43:23) Closing Thanks and Subscribe Learn more about your ad choices. Visit megaphone.fm/adchoices

  27. 52

    Hunting 80,000 Deer to Save Hawaii | Jake Muise

    Jake Muise grew up in rural Canada hunting, fishing, and living off the land. A Division I volleyball scholarship brought him to Hawaii, but a dorm room mix-up changed the course of his life forever. After being welcomed into a local Molokai family, Jake developed a deep connection to Hawaiian culture and became fascinated by Hawaii's invasive axis deer problem. What began as an obsession eventually became Maui Nui Venison, one of the most innovative food and conservation companies in the world. Today, Maui Nui operates a USDA-certified wild harvest system unlike anything else in existence, balancing deer populations while providing some of the most nutrient-dense red meat available. In this conversation, Jake shares the story behind Maui Nui, how he helped remove illegally introduced deer from Hawaii's Big Island, the challenges of building a first-of-its-kind USDA-approved harvesting system, and the leadership principles that power one of the most disciplined teams you'll ever encounter. This is a conversation about obsession, conservation, entrepreneurship, culture, leadership, and doing meaningful work that lasts. Thank you to our sponsors Helix Sleep: http://helixsleep.com/rideout  Ken’s book now available here: https://www.theothersideofhard.com/ Chapters (00:00) Welcome to Kona (00:20) Ironman Kona Stories (02:06) Jake’s Roots in Canada (02:58) Volleyball to Hawaii (06:12) Dorm Mixup and Local Life (09:44) Molokai Culture Explained (11:34) Meeting His Future Wife (15:03) Leading Maui Nui’s Team (20:15) Sponsor Break Helix Sleep (21:19) Origins of Maui Nui (23:19) Drought Sparks the Mission (25:53) Axis Deer Institute Hustle (26:54) Illegal Deer on Big Island (29:46) Infrared Night Hunting Tech (32:30) USDA Approval Challenge (39:16) Practicing Before Inspection (40:24) The USDA Ride Along (42:20) Remortgage to Scale (43:42) Pitching Passion Investors (46:53) Balancing Deer Populations (50:28) USDA Rules and Marksmanship (55:45) Inside the Night Harvest (58:35) Holo Ai Community Giveaway (01:04:59) Humble Hungry Smart Hiring (01:14:02) Gamified Discipline Experiments (01:20:59) Graduation and Farewell (01:22:52) Podcast Wrap and Subscribe Learn more about your ad choices. Visit megaphone.fm/adchoices

  28. 51

    Dyslexia. Racism. The NFL. | Chris Spencer

    Chris Spencer grew up in rural Mississippi working cotton fields, facing racism firsthand, and struggling with dyslexia throughout school. Football became the one place where everything made sense. That path eventually took him from being one of the top recruits in the country to Ole Miss, where he played alongside Eli Manning, before becoming the 26th overall pick in the NFL Draft and spending a decade in the league. But this conversation goes far beyond football. Chris shares the lessons he learned from his family, the story behind a recruiter offering $100,000 cash that his mother refused, how dyslexia became his greatest advantage, and the challenges of building an identity after the NFL. Today, Chris is the founder of TeamQ, an AI-driven platform helping organizations identify and develop the intangibles that drive performance. This is a powerful conversation about resilience, self-awareness, and turning adversity into opportunity. Thank you to our sponsors Wild Roman: wildroman.com/rideout Code “RIDEOUT15” Athletic Nicotine: https://athleticnicotine.com/rideout Code "RIDEOUT" Ken’s book now available here: https://www.theothersideofhard.com/ Chapters (00:00) Meet Chris Spencer (00:52) Mississippi Roots (02:50) Racism and Resilience (06:13) Mom’s Guiding Principles (08:08) Football Finds Him (11:29) First Pads Reality Check (14:49) Size, Diet, and Position (17:13) From Fun to Future (20:29) Dyslexia as Superpower (25:15) Training and Powerlifting (29:54) Recruiting Goes National (31:09) Football Privilege Fame (32:15) Recruiting Home Visits (32:43) Cash Offer Rejected (35:37) Choosing Ole Miss (38:22) Team Culture Fit (41:30) Freshman Weight Room (46:10) Speed Technique Reality (47:30) Prop 48 Redshirt (49:13) Becoming Eli Center (53:12) NFL Draft Projection (58:15) IMG Combine Prep (59:24) Seattle Scheme Clues (01:00:06) Draft Night Surprise (01:03:35) Rookie Deal Holdout (01:07:29) First NFL Snaps (01:09:53) Money and Family First (01:13:05) Super Bowl Rookie Year (01:15:28) Beast Mode Arrives (01:18:23) Lockout and Leaving Seattle (01:21:23) Choosing the Bears (01:22:28) Giants Deal Falls Apart (01:23:36) Chicago Coach Conflict (01:24:50) Thrown Into Guard Midgame (01:27:28) Proving Toughness Through Injuries (01:31:47) Choosing Nashville and Settling Down (01:32:49) COVID House Sale and New Friendship (01:36:05) Building TeamQ After Football (01:40:13) How TeamQ Measures Intangibles (01:44:41) Onsite Therapy and Microtraumas (01:50:18) Where to Find TeamQ (01:51:54) Subscribe and Sponsor Shoutouts Learn more about your ad choices. Visit megaphone.fm/adchoices

  29. 50

    The Walk-On Who Refused to Leave | Todd Anderson

    Todd Anderson wasn't supposed to play at Michigan State. He came from a tiny town in Michigan. No Division I offers. No scholarship. No clear path forward. Then a chance opportunity earned him a walk-on spot at Michigan State. What followed was years of injuries, setbacks, position changes, and moments where quitting felt like the logical choice. Eventually, Todd became a key contributor on a Michigan State team that won the Big Ten and beat Georgia in the Capital One Bowl. He earned an NFL opportunity with the Rams before a suspension tied to a stimulant in an energy supplement ended his path. But football wasn't the end of the story. Today, Todd is the founder of Dream Recovery, one of the fastest-growing sleep brands in the country, helping athletes and everyday people improve performance through better sleep. We talk about football, failure, identity, resilience, entrepreneurship, sleep, and why some of life's biggest setbacks end up creating entirely new paths. Thank you to our sponsors Helix Sleep: http://helixsleep.com/rideout  Wild Roman: wildroman.com/rideout Code “RIDEOUT15” Ken’s book now available here: https://www.theothersideofhard.com/ Chapters (00:00) Meet Todd Anderson (00:21) Dream Recovery Takes Off (01:51) Small Town Roots (03:11) Multi Sport Standout (04:43) Michigan State Walk On Break (10:37) Reality Check In Camp (13:38) Injuries And Comeback (17:37) Fullback Breakthrough Season (21:18) Pro Day And NFL Shot (23:43) Rams Camp And Drug Test Scare (25:25) Energy Shot Fallout (25:56) Drug Test Mixup (26:44) Diluted Sample Drama (27:16) Practice Squad Reality (28:14) Four Game Suspension (28:35) Walking Away From NFL (29:06) Heart Not In It (30:46) Retirement And Identity (32:30) Fathers Day Ad Break (33:45) College Touchdown Memory (34:53) Proud Dad Stories (35:54) Learning Toughness (37:23) Wrestling Respect (38:25) Dad Health Scare (39:55) Katie Comeback Ends (40:40) Pulmonary Embolism Ordeal (41:23) Misdiagnosis And Recovery (43:00) Rams Rookie Camp (44:17) College Football Culture (44:49) Gerard Butler Hype (45:28) Uniforms And Recruiting (47:25) Michigan State Gear Haul (48:45) NFL Gear And Nike Switch (50:09) Camp Mental Grind (50:52) Football Scheme Complexity (51:35) Quarterback Pocket Pressure (52:41) From Training to Sleep (54:31) Why Sleep Comes First (56:21) Dream Product Lineup (57:26) Mouth Breathing and Teeth (59:59) Nasal Strips and Afrin Loop (01:01:57) Silk Pillowcase Science (01:03:09) Building Dream Recovery (01:06:28) Sleep Tech and Alcohol (01:08:15) Baby News and Teslas (01:13:06) Chicago Marathon Mindset (01:14:45) Wrap Up and Subscribe Learn more about your ad choices. Visit megaphone.fm/adchoices

  30. 49

    The Voice of the UFC | Jon Anik

    Jon Anik is the voice of the UFC. Before calling the biggest fights in the world, he was a young broadcaster at ESPN trying to find his place in sports media. Then Dana White offered him a chance to help build the UFC during one of the most important growth periods in the company's history. In this conversation, Jon shares the journey from ESPN to the UFC, what it was like earning Dana White's trust, working alongside Joe Rogan and Daniel Cormier, dealing with public criticism, and the preparation required to perform at the highest level for more than a decade. We also discuss the upcoming UFC event at the White House, the legendary Sphere event in Las Vegas, sports betting, Boston sports, and why repetition and discipline matter more than talent. This is a fascinating look behind the curtain of the UFC from the man who has called it all. Thank you to our sponsors Rho Nutrition: https://rhonutrition.com/ Code "RIDEOUT" Ken’s book now available here: https://www.theothersideofhard.com/ Chapters (00:00) Meeting Jon Anik (00:26) Fame and Work Ethic (02:24) Working With Dana (04:30) Dana’s Generosity Stories (06:49) Broadcast Feedback Loop (10:28) Crafting Signature Calls (12:40) Prep and Memorization (14:01) Early Career Origins (18:31) ESPN to UFC Breakthrough (21:30) Leaving ESPN for UFC (24:52) White House Event Hype (28:28) Sphere and Live Venues (29:45) Music Tangent and Rogan (31:03) Rogan’s Generosity (32:45) Broadcast Chemistry (33:38) Handling Online Hate (36:06) Asking for Favors (38:52) Boston vs New York Fandom (43:17) Red Sox Reality Check (44:33) Twin Brother’s Career (46:10) Alt Combat Sports Rules (48:46) Gina vs Ronda Rewind (52:33) Women’s MMA Evolution (55:25) Betting and Politics (01:00:16) Broadcast Booth Dynamics (01:02:41) Wrap Up and Subscribe Learn more about your ad choices. Visit megaphone.fm/adchoices

  31. 48

    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

  32. 47

    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

  33. 46

    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

  34. 45

    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

  35. 44

    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

  36. 43

    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

  37. 42

    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

  38. 41

    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

  39. 40

    From Navy SEAL to Breaking Point to Building Lives | Johnny Wilson

    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

  40. 39

    War Took His Legs. Not His Life. | Jason Smith

    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

  41. 38

    From Olympic Pressure to Peace and Purpose | Katie Hoff

    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

  42. 37

    Broken, Beat and a World Title | “Irish” Micky Ward

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

  43. 36

    Living on the Edge Without Losing Each Other | Laird Hamilton & Gabby Reece

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

  44. 35

    From NFL Star to Starting Over | Eric Decker

    Former NFL wide receiver Eric Decker had everything most people chase—success, fame, a Super Bowl appearance, and a picture-perfect life on the outside. But when football ended, so did the structure, identity, and validation he had relied on his entire life. In this conversation, Eric opens up about what really happens after the dream is over—struggling with confidence, anxiety, and purpose, and confronting the deeper issues rooted in childhood, family, and self-worth. He shares the turning point that forced him to face it all: therapy, vulnerability, and doing the inner work most men avoid. We also go deep on fatherhood, pressure, and how to show up better for your kids… plus the journey from small-town Minnesota to the NFL, draft-day uncertainty, a devastating Lisfranc injury, and playing in a Super Bowl. This is a conversation about identity, masculinity, and what it actually takes to rebuild your life when the thing you thought defined you is gone. 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) Eric Decker Joins (00:11) Vulnerability After Sports (02:55) Onsite Therapy Weekend (07:43) Men Asking For Help (12:25) Small Town Sports Roots (18:16) Family Divorce And Dad Pressure (20:25) Parenting Youth Sports (29:27) College Scholarship Moment (31:54) Grinding Through Minnesota (33:08) Receiver Skills And Intangibles (35:24) Finding Soft Spots (35:51) Two Sport Pivot (37:47) College Breakout Years (39:46) Choosing Football Over Baseball (41:09) Lisfranc Injury Fallout (44:43) Draft Day Rollercoaster (50:02) Rookie Camp Reality Check (55:08) Special Teams Baptism (01:02:35) Peyton Era And Super Bowl (01:05:19) Super Bowl Week Chaos (01:07:01) Kids And Memorabilia (01:08:38) Meeting Jess After Rookie Year (01:09:02) Lockout Year Adventures (01:09:35) Meeting Jess Long Distance (01:10:51) Early Career Growing Pains (01:12:20) Why Nashville Works (01:13:46) Authenticity And Real Friends (01:14:52) Retirement Identity Crisis (01:16:26) Jess Pushes For Help (01:18:33) Reality Show Origins (01:25:37) Special Forces In Morocco (01:32:17) Pickleball And New Ventures (01:34:57) Friendship And Closing Advice Learn more about your ad choices. Visit megaphone.fm/adchoices

  45. 34

    Hate, Heartbreak, and a Comeback Win | Kaitlyn Bristowe

    Kaitlyn Bristowe went from a small town in Canada to the center of reality TV—and paid the price for it. She opens up about chasing a dance career, hitting rock bottom after a breakup, and rebuilding her life from nothing. Then came The Bachelor and The Bachelorette—and with it, fame, manipulation behind the scenes, and a level of public backlash that nearly broke her. She talks about being slut-shamed on national TV, dealing with threats, and navigating the pressure of building a career in a space that didn’t exist yet. But she didn’t stop there. From Broadway to building a business, writing music, and ultimately winning Dancing With the Stars, Kaitlyn shares how she turned chaos into momentum—and why doing the inner work mattered just as much as the external success. This is a conversation about identity, resilience, and staying true to yourself when the world is trying to define you. 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 Welcome and Reality Stigma 00:49 Instagram Early Days 02:07 Brand Deals and Trust 03:11 Influencer Culture Shift 05:22 Small Town Roots 06:37 Dance Dream to Vancouver 07:20 College Blueprint Debate 10:16 Hockey Life and Rock Bottom 12:50 Signed Up for The Bachelor 13:30 Adversity and Mental Health 15:31 Bachelor Night One Chaos 18:13 Bali Blindside Elimination 21:26 Becoming The Bachelorette 22:13 Negotiating the Contract 25:14 Bachelorette Behind the Scenes 26:31 Sex Talk and Producer Manipulation 30:24 Backlash and Mean Tweets 31:25 Trolls And Triggers 32:42 Reality TV Relationship Fallout 34:16 Post Show Career Whiplash 34:54 Broadway Dream And Burnout 37:11 Paparazzi And Being Recognized 37:50 Sponsor Break Athletic Brewing 38:43 Broadway Nerves And Mom Moment 39:57 DWTS Drama And Contract Twist 42:39 Winning DWTS Through Injury 47:55 Freestyle Finale And Nev Beef 49:46 Staying True And Inner Child Work 56:28 Hoffman Process And Self Dates 01:00:07 Psychedelics And Ego Death Story 01:02:25 Closing Thoughts And Subscribe Learn more about your ad choices. Visit megaphone.fm/adchoices

  46. 33

    From Dish Pit to 30 Restaurants | Phillip Frankland Lee

    Phillip Frankland Lee went from washing dishes to building one of the most unique restaurant empires in the world. But it didn’t happen clean. He was betrayed by a business partner who disappeared, leaving him with debt and lawsuits. He got hit with a $15M legal battle from private equity. His restaurants were shut down overnight during COVID. And instead of folding, he doubled down. In this episode, Phillip breaks down how he turned Sushi by Scratch into a full sensory “show,” why he believes great food should hit even if you’re not a foodie, and how relentless work ethic—from punk rock touring to Michelin kitchens—shaped everything he built. This is a story about obsession, resilience, and refusing to lose—no matter how many times the game resets. 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) Meet the Sushi Showman (00:31) Concert vs Show Dining (02:27) Speakeasy Vibe Origins (05:25) Ten Seats Omakase Flow (06:55) Sushi Obsession at 13 (11:01) Family Drive and Discipline (14:54) From Bands to Dish Pit (18:49) Quitting Culinary School (21:34) Kitchen Culture and Leadership (26:58) First Sous Chef Reality (31:28) Michelin Standards at Hatfield's (35:43) Chicago Three Star Leap (37:42) Chef Ride Stories (39:18) Chicago Kitchen Lessons (40:49) LA Proposal Reset (41:02) Tasting Menu Delivery (43:10) Scratch Bar Deal (46:18) Critics And Standards (47:53) Coffee Shop Fallout (49:50) Apartment Pop Up (51:31) Beverly Hills Move (52:51) Jonathan Gold Boost (55:36) Health Scare Pivot (58:05) Food Network Wins (59:02) Top Chef Controversy (01:06:17) Partner Betrayal (01:10:48) New Backer Rebuild (01:14:46) Pandemic Survival Mode (01:17:10) Austin Pop Up Breakthrough (01:17:34) Rogan Sells Out February (01:19:23) Austin Popup Becomes Permanent (01:20:23) Private Equity Deal Trap (01:22:20) Hit With $15M Lawsuit (01:28:03) Opening 30 Restaurants to Survive (01:30:06) Four Acre Michelin Dream (01:36:14) Hunting and Whole Animal Cooking (01:46:35) Nashville Burger Launch (01:49:43) Mindset Gratitude and Follow Through (01:53:22) Closing Thanks and Subscribe Learn more about your ad choices. Visit megaphone.fm/adchoices

  47. 32

    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

  48. 31

    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

  49. 30

    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

  50. 29

    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

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ABOUT THIS SHOW

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.

HOSTED BY

Ken Rideout

Frequently Asked Questions

How many episodes does RIDEOUT: The Other Side of Hard have?

RIDEOUT: The Other Side of Hard currently has 50 episodes available on PodParley. New episodes are automatically indexed when they're published to the podcast feed.

What is RIDEOUT: The Other Side of Hard about?

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.

How often does RIDEOUT: The Other Side of Hard release new episodes?

RIDEOUT: The Other Side of Hard has 50 episodes. Check the episode list to see recent publication dates and frequency.

Where can I listen to RIDEOUT: The Other Side of Hard?

You can listen to RIDEOUT: The Other Side of Hard on PodParley by clicking any episode. We provide an embedded audio player for direct listening, and you can also subscribe via your preferred podcast app using the RSS feed.

Who hosts RIDEOUT: The Other Side of Hard?

RIDEOUT: The Other Side of Hard is created and hosted by Ken Rideout.
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