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.

RIDEOUT: The Other Side of Hard is a education podcast hosted by Ken Rideout, with 74 episodes on record and a Required Pod Score of 80. PitchCentric scores this show on Booking Probability, Listen Score, and live audience signals refreshed every 24 hours.

Ken Rideout hosts RIDEOUT: The Other Side of Hard, a education show with 74 episodes published.

Our AI reads these to draft pitches. Use them as grounding for a pitch that cites a real guest and a specific topic.

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  Episode #74

  Too Small for the NFL. Then He Broke a Chiefs Record. | Dexter McCluster

  Sep 16, 20261h 36m

  Dexter McCluster is five-foot-eight and 165 pounds. Bobby Bowden told him he could play defensive back. Urban Meyer told him he could return kicks. He turned both of them down because he knew who he was, and he needed the ball in his hands. He went to Ole Miss instead and became the first player in SEC history to rush for 1,000 yards and catch for 500 in the same season. He ran for 282 yards on Lane Kiffin's Tennessee with the coach who recruited him standing on the other sideline, won back-to-back Cotton Bowl MVPs, and got drafted 36th overall by the Chiefs. In his first NFL game, on Monday Night Football, in the rain, he returned a punt 94 yards for a touchdown. This week I sat down with Dexter to talk about all of it. Becoming a father at 17 and telling his parents within half an hour. Waiting for the draft call on a couch with a Nokia phone and camera crews watching. Buying his mom the house he promised her as a kid. Making the Pro Bowl and then being told he wasn't really a running back or a receiver. We also get into the part that never makes the highlights. Getting named a captain in Tennessee and then getting cut before the season, the year Derrick Henry showed up. Crying the whole drive home. Three retirements. The months he spent on his patio from six in the morning to six at night, drinking more than he should have, until his wife told him, "Don't forget who you are." Today Dexter trains athletes, coaches running backs at Father Ryan, and just had his sixth kid, his first boy. We weigh exactly the same. Only one of us has a Chiefs record. Hope you guys enjoy this one. Follow Dexter: @dextermccluster and @mcclusterfit 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 Dexter McCluster (00:34) You Can't Fake Running Back (02:09) Rookie Blitz Pickup Test (03:19) Growing Up in Largo (04:35) High Jumping at Five Eight (05:31) Dad's No Summer Job Rule (07:20) Six Kids and a Baby Boy (08:06) Mister 2000 Senior Season (09:18) Too Small for Florida State (09:47) A Father at Seventeen (10:59) Orgeron in the Living Room (12:24) Slot Receiver Not Running Back (12:45) Sponsor Break ROKA (14:29) Winning the Starting Job (15:40) Combine Weigh In Nightmare (18:14) Losing His Daughter's Mother (19:46) Culture Shock at Ole Miss (22:34) Patrick Willis and Baby Hester (24:45) Orgeron's Brutal Camp (26:26) First Game Trick Play Touchdown (29:28) Gear Cleats and No Swag (33:10) NIL Money and the Stipend (36:38) Broadcast Journalism Degree (37:28) Begging Houston Nutt for the Ball (38:48) Five Minutes Against South Carolina (39:43) First in SEC History (40:05) Back to Back Cotton Bowl MVP (41:00) 282 Yards on Tennessee (42:56) Orgeron's Message Through Dad (43:36) Scouts Start Sniffing (45:41) Study Tables and Football Classes (47:23) Choosing an Agent (49:34) Combine Prep in McKinney (51:03) Finishing the Degree Twenty Years Later (52:10) Draft Day on the Couch (54:18) The Call From Clark Hunt (56:28) Dad's Number 22 (57:04) First Signing Bonus (58:06) Buying Mom a House (01:01:55) Last Old School Training Camp (01:02:44) Monday Night Football Debut (01:05:10) Just Catch the Ball (01:06:10) 94 Yards Chiefs Record (01:06:44) Cassel Pollard and Small Worlds (01:07:32) Andy Reid and the Pro Bowl (01:08:55) Just a Punt Returner (01:09:12) Twelve Million to Tennessee (01:11:03) Everybody Comes Out of the Woodwork (01:13:36) Derrick Henry Wants 22 (01:15:00) The Grim Reaper (01:15:51) Captain Then Cut (01:17:00) You Will See Me Again (01:17:34) Crying All the Way Home (01:18:00) Ken's Berlin Humiliation (01:19:16) Three Weeks Without a Team (01:20:12) San Diego and Atlanta Call (01:21:49) Fractured Arm and Wanting Home (01:23:11) First Retirement (01:24:04) Toronto Argonauts Detour (01:27:38) Depression on the Patio (01:29:00) Don't Forget Who You Are (01:29:20) McCluster Fit Is Born (01:29:56) One Last Season in Worcester (01:31:46) Father Ryan and Family Now (01:32:19) Neighbors and the Tailgate (01:34:01) Where to Find Dexter (01:34:39) Host Outro and Subscribe Learn more about your ad choices. Visit megaphone.fm/adchoices

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  Episode #73

  From a Prison Cell to Nike Brand Director | Jordan Rogers

  Sep 11, 20261h 55m

  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

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  Episode #72

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

  Sep 9, 20262h 11m

  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

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  Episode #71

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

  Sep 4, 20261h 28m

  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

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  Episode #70

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

  Sep 2, 20261h 9m

  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

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