
Advertise on podcast: RIDEOUT: The Other Side of Hard
Rating
5from
This podcast has
80 episodes
Language
EnglishPublisher
Ken RideoutExplicit
No
Date created
2025/11/11
Latest episode
2026/10/02
Average duration
114 min.
Release period
4 days
Description
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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255 Pounds at 33. Eight Miles a Day at 64. | BeBe Winans
2026/10/02
BeBe Winans grew up a block from Smokey Robinson in Detroit, shoveling his snow for $25 when everyone else paid $2. Stevie Wonder's house was behind theirs. He was the seventh of ten Winans kids, and when his four older brothers got signed by Quincy Jones, BeBe drove the van.
Right out of high school he and his sister CeCe auditioned for a Christian TV network in Charlotte. She got the job. He didn't. Their dad wouldn't let her go alone, so BeBe went as her chaperone, planning to work at a grocery store. Then Jim Bakker walked into a rehearsal and told the two of them to sing "Up Where We Belong" as a duet. That is how BeBe & CeCe Winans started. Capitol Records followed, then gold, then platinum, then six Grammys. Whitney Houston sang backup on their first tour and made their outfits herself while Clive Davis lost his mind.
What almost nobody saw was the hotel mirror in California at 33. BeBe was 255 pounds and couldn't get through two minutes on a treadmill. His trainer told him it took 33 years to get there, so give yourself more than three days. He got to 180 and never went back. He is 64 now, and I see him running past my house in Brentwood in the rain and on the ice, every day but Sunday. That is how we met.
This week I sat down with my neighbor to get the whole story. The fourth-grade poem that made him a writer. Michael Jordan at a Detroit baggage claim telling him to put his head down and listen. Stevie Wonder calling him an incredible writer from the side of the stage. Dolly Parton at the register of the country store down the road. And the tour with CeCe next April, their first in 25 years.
One of the kindest people I know, and one hell of a storyteller. Hope you guys enjoy this one.
Follow BeBe: @bebewinans
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 BeBe Winans
(00:40) The Guy Who Runs Every Day
(01:18) Jelly Roll Knows Him
(02:21) Growing Up in Motown
(02:41) Shoveling Smokey Robinson's Snow
(03:58) Ten Kids and a Piano
(05:16) The Winans and Quincy Jones
(06:24) A Poem Called The Wind
(07:28) A Catalog of 3000 Songs
(08:36) Never Sing Your Own Demo
(09:16) Sponsor Break ROKA
(11:01) Meeting Whitney Houston
(12:10) The Bodyguard Soundtrack
(12:30) What the Music Means to People
(13:10) Gladys Knight at the Ryman
(15:17) Trading Names in a Blizzard
(15:47) No Excuses in the Rain
(16:10) Nothing Flexes Like Being in Shape
(17:13) Rejected at the Charlotte Audition
(18:15) Chaperoning CeCe at PTL
(18:41) Jim Bakker Makes Them a Duet
(19:54) Signing With Capitol Records
(20:52) Gold Then Platinum
(21:43) Keeping the Solo Rights
(23:10) The Mirror in California
(24:19) Two Minutes on a Treadmill
(24:54) From 255 to 180
(25:45) A Banana in Every State
(26:21) Not Donny and Marie
(26:44) When One Winans Wins
(27:39) Mom's 90th Birthday
(28:52) Dad Hollering From the Front Row
(29:12) Telling Mom She Can Retire
(29:51) Ken Embarrasses His Daughter
(31:33) Dad's Last Words
(33:06) Sing for 12 Like It's 120,000
(35:37) Greek Theater and Carnegie Hall
(36:04) Guards on a Train in Russia
(38:44) First Tour With CeCe in 25 Years
(39:21) Driving the Van for His Brothers
(40:40) Whitney Houston Sang Backup
(41:39) Whitney Runs the Tour Bus
(44:46) The Lady Who Didn't Know Whitney
(45:45) Stevie Wonder Sings Happy Birthday
(47:05) Prince in the Next Seat
(48:48) Michael Jordan at Baggage Claim
(50:48) Dolly Parton at the Country Store
(54:43) Ken's Mountain Lion
(55:38) Cougars in Vancouver
(57:16) Running With Rhinos in Kenya
(57:35) Two Kids Who Don't Sing
(58:55) Niece Deborah Joy on Greenleaf
(59:20) Fifteen Cities in 2027
(01:00:28) Building the Show
(01:02:25) Don't Get Addicted to the Applause
(01:02:38) A Musical Bound for Broadway
(01:03:17) The Business of a Tour
(01:05:43) Pull Up Your Brave Pants
(01:06:03) Private Shows and Oprah
(01:07:24) Eight and a Half Miles Every Day
(01:08:15) Lifting Right After the Run
(01:09:43) See You in New York
(01:10:06) Host Outro and Subscribe
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One Instagram Post Ended His 12-Year MLB Career | Anthony Bass
2026/09/30
Anthony Bass was a Division II kid from Trenton, Michigan who threw 88 to 92 like every other college pitcher. Then in the summer of 2007 he watched a rookie his own size named Tim Lincecum throw 98 for the Giants, copied his delivery in the bullpen the next day, and never threw a fastball under 94 in his next outing. Twelve scout envelopes followed. So did a fifth-round pick by the Padres, a $166,000 signing bonus, and 12 seasons in the big leagues with seven teams.
What almost nobody saw was how it ended. On an off day in Toronto in May 2023, Anthony reposted a video calling on Christians to boycott Target and Bud Light. His agent called while he was out fishing. He took it down. His wife Sydney told him not to hide who he is, so he put it back up. The next time he ran out of the bullpen at home, his own fans booed him through the entire inning. Eleven days after the post the Blue Jays designated him for assignment, the GM called it a baseball decision, and no other team would touch him. He was 35.
This week I sat down with my friend Anthony to get the whole ride. 100 swings off a tee in a freezing garage. The fake call-up, then the real one: a start in Colorado and a win in his debut before they sent him back to Double-A that same night. $900 a month in the minors to $40,000 a month in the show. A perfect game into the sixth in San Francisco. A season in Japan where a 21-year-old teammate named Shohei Ohtani threw 100 on opening day and Anthony landed a remote-control helicopter on his head in the clubhouse. And the 2022 playoff inning where he never recorded an out.
We also get into the part that never makes the highlights. The scripted apology. The resentment when he came home. What he would do differently. And why coaching kids is the next chapter.
This guy can tell a story. Hope you guys enjoy this one.
Follow Anthony: @anthonyebass
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"
AMP Fitness: amp.ai/rideout
OMRE: omre.co Code "RIDEOUT"
Ken's book now available here: https://www.theothersideofhard.com/
Chapters
(00:00) Sponsor Break OMRE
(00:46) Meet Anthony Bass
(03:57) Growing Up in Trenton Michigan
(04:30) 100 Swings in a Frozen Garage
(05:22) A Railroad Dad Who Played Catch
(06:58) Copying Tim Lincecum
(10:00) Suddenly Throwing 94
(10:38) Twelve Envelopes at Scout Day
(12:38) Sponsor Break ROKA
(14:17) Drafted by the Padres
(14:56) Eugene Fort Wayne Lake Elsinore
(16:52) Who Gets Weeded Out
(19:45) Ken Raids the Bruins Equipment Room
(22:21) The Fake Call Up
(23:23) Starting in Colorado Tomorrow
(24:20) Calling Mom and the College Catcher
(25:40) Eight Hour Bus Rides
(26:43) Swinging Late at 98
(28:40) A Room of His Own at the Ritz
(30:05) Meeting Bud Black
(30:40) Bass on the Back of the Jersey
(33:13) First Batter Carlos Gonzalez
(35:30) Winning His Debut in the Rain
(36:00) Sent Back Down That Night
(36:27) Heath Bell's Three Week Prediction
(37:07) Sponsor Break AMP
(38:16) Living Out of a Suitcase
(39:40) From 900 a Month to the League Minimum
(41:15) The 200,000 Pay Stub
(44:00) Inconsistent in the Rotation
(44:52) A Perfect Game Into the Sixth
(46:40) The Triple A Grind
(48:05) Traded to Houston
(48:34) Hurt and Becoming a Journeyman
(50:40) The Fear of Never Coming Back
(51:46) Three Hours in a Japanese Grocery Store
(52:23) A Teammate Named Shohei Ohtani
(52:51) 100 MPH on Opening Day
(55:00) Ohtani Hiding in Airports
(56:00) Winning the Japan Series
(57:41) Landing a Helicopter on Ohtani
(59:08) Dodgers Money and the Salary Cap
(01:01:36) Turning Down 1.5 Million to Come Home
(01:03:25) The Cubs and Hand Foot and Mouth
(01:04:40) Closing Games in Louisville
(01:05:21) The Mariners Come Calling
(01:07:20) Claimed by Toronto
(01:07:50) Closing in the COVID Season
(01:08:27) A Career Year in Miami
(01:09:23) The Playoff Inning Without an Out
(01:10:22) Sponsor Break OMRE
(01:12:40) The Post
(01:14:20) Sydney Says Don't Take It Down
(01:15:29) Called Into the GM's Office
(01:16:20) A 37 Second Scripted Apology
(01:17:45) Booed for an Entire Inning
(01:19:04) Released as a Baseball Decision
(01:20:27) The Dodgers and Diamondbacks Pass
(01:21:40) The Next Chapter Is Coaching
(01:22:00) Ken's Recurring Bruins Dream
(01:23:12) Fenway and a First Pitch Dream
(01:27:54) Middle Tennessee Talent
(01:30:33) Training for HYROX Nashville
(01:30:50) Ken's Wall Ball Disaster
(01:34:40) Confront What Scares You
(01:36:09) Four Kids Under Ten
(01:38:13) Host Outro and Subscribe
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It's Just Walking. 1 in 3 Don't Finish. | Marc Hodulich
2026/09/25
Marc Hodulich was a high school sophomore when he ran five months on a broken foot. The scan turned into a bone graft from his shin, two pins across his foot and three orthopedic surgeons before one of them would say he might run again. The pins are still in there 30 years later.
He went on to run track at Auburn in the SEC, and then he built the hardest event most people will ever finish. Marc is the co-founder and CEO of 29029. Hike up a mountain, ride the gondola down, repeat until you have climbed 29,029 feet, the height of Everest, inside 36 hours. It is not a race. No clock, no trophy, no paid sponsors. It is walking. And since the first event in 2017, only 68 percent of the people who start have finished. A marathon is 98.
This week I sat down with Marc, one of my closest friends, to get the whole story. Birmingham. Selling payroll door to door in Manhattan while working two other jobs. Six years in management consulting until a partner told him he did not want to go deep on anything. The Wall Street Decathlon he started on the side that raised millions for pediatric cancer research at Memorial Sloan Kettering. Meeting Jesse Itzler at their kids' flag football practice. Why 29029 has never taken a paid sponsor. The 80-year-old who called the event "frustratingly doable." And the summer he, Jesse and Colin O'Brady did 29,029 feet three ways, on the bike, in the water and on the mountain.
We also get into the part that never makes the highlights. The day I quit at Kona. What I went through in Mexico. Why Marc deleted email off his phone. And what he means by fulfillment over achievement.
Follow Marc: @marchodulich
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"
OMRE: omre.co Code "KEN"
Ken's book now available here: https://www.theothersideofhard.com/
Chapters
(00:00) Meet Marc Hodulich
(00:48) Growing Up in Birmingham
(02:08) The High School Miler
(03:02) Running Track at Auburn
(06:22) The Book Scholarship
(06:53) Five Months on a Broken Foot
(09:27) Raising Chase and Dylan
(11:38) Sponsor Break ROKA
(13:18) Preparing for an Empty House
(15:19) Selling Payroll Door to Door
(16:46) Six Years in Consulting
(17:50) A Partner Calls His Bluff
(18:26) The Wall Street Decathlon
(19:44) Scared to Quit
(21:11) Who's the Better Athlete
(23:28) Bought Out by His Partner
(24:26) Why 29029 Has No Paid Sponsors
(25:46) The Origins of 29029
(26:14) Running to Flag Football Practice
(27:19) Owning Everest in 36 Hours
(28:42) An On Ramp to Trail Running
(30:54) Earned Luxury at the Ritz
(31:59) Sponsor Break OMRE
(33:37) Early Mistakes at the First Event
(34:29) Hard Things Change People
(36:00) A 68 Percent Finish Rate
(36:45) Quit Feeling Sorry for Yourself
(38:19) The Average Participant Is 50
(39:36) The Day Ken Quit at Kona
(40:42) Training for Bad Conditions
(42:48) Fulfillment Before the Finish Line
(44:07) Teepees at Snowbasin
(45:14) It's All Free
(46:05) Ken and Rob Show Up Cocky
(46:58) Frustratingly Doable at 80
(47:56) No Awards for Finishing First
(49:01) Lapping the Field at Whistler
(50:22) Negotiating With Yourself
(52:48) Honest Conversations on the Mountain
(53:27) The Idea Behind TRAIL
(55:01) Leadville and Telluride
(57:14) Ken vs Tyler at TRAIL
(59:12) The Triple, 29029 Three Ways
(01:00:43) A 5.5 Mile Swim
(01:01:32) Buying a Bike for the Climb
(01:04:10) The Hardest Part Was Staying Present
(01:04:48) A Text From Chase
(01:06:18) Cramping on Lap Five
(01:07:02) Whitecaps on the Lake
(01:09:19) The Safety Kayak Wake Up Call
(01:11:38) Ken's Topanga Canyon Crash
(01:13:34) Sitting in It for a While
(01:14:44) Joy in Other People Winning
(01:15:43) Ray Hicks and the Big Cup
(01:16:47) Knowing What You Don't Want
(01:17:24) When Racing Becomes Performative
(01:18:40) Five Days Off in Mexico
(01:19:05) Uncomfortable Plant Therapy
(01:24:05) 5 MeO DMT and Ego Death
(01:26:18) Grateful for What Matters
(01:28:01) Deleting Email Off His Phone
(01:31:09) The Runner's High Afterwards
(01:31:46) 29029 Goes to Verbier
(01:33:26) Fulfillment Not Achievement
(01:34:06) Host Outro and Subscribe
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The Blast that Saved his Life | Mike Sarraille
2026/09/23
Mike Sarraille was three feet away when Michael Monsoor jumped on a grenade on a rooftop in Ramadi and smothered the blast. Mike and another SEAL took the shrapnel Monsoor’s body couldn’t block. Monsoor didn’t survive. He was posthumously awarded the Medal of Honor.
That day is the middle of the story, not the end of it. Mike dropped out of the University of Colorado to enlist as a Recon Marine. Boot camp, scout sniper school, a Force Recon guarantee, an officer package to Texas A&M. 9/11 hit three weeks after he finished OCS. He laterally transferred to the Navy, made it through BUD/S, and landed on SEAL Team 3 in time for the 2006 Battle of Ramadi. After Monsoor was killed, Mike switched his own name tag onto a departing platoon roster to force his way back into the fight, then survived the Battle of Sadr City against Iranian-backed militia. He was later selected for DEVGRU, did an exchange tour as a troop commander at Delta, and was on the ground in Afghanistan the night Adam Brown, of the book Fearless, was killed.
This week I sat down with Mike to talk about all of it: Ramadi, DEVGRU, the NCIS investigation that followed his own attempt to get his teammates recognized for valor, and what he’s building now as Chief Talent Officer of Overwatch Mission Critical, one of the largest labor providers to the data center industry. He’s also ranked the #3 leadership speaker in the world, behind only Simon Sinek, and his new book, Teams, comes out in January.
Follow Mike on Instagram: @mr.sarraille.
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”
Ken’s book now available here: https://www.theothersideofhard.com/
Chapters
(00:00) Meet Mike Sarraille
(02:04) Admiring Dr. Jonny Kim
(03:06) Raising Kids Who Compete
(05:35) Speaking to the Boston Bruins
(07:01) Growing Up in the Bay Area
(09:00) Dropping Out of Colorado
(09:29) Meeting a Force Recon Marine
(11:29) Force Recon, Delta and the Tier One Units
(14:42) Marine Corps Boot Camp
(16:59) Sponsor Break ROKA
(17:15) The Melting Pot of Boot Camp
(19:12) The Recon Guarantee and Entrance Test
(24:19) Scout Sniper School and the Stalking Phase
(26:26) Texas A&M and the Officer Package
(28:16) 9/11 Changes the Plan
(29:34) Telling the Marine Corps He’s Leaving
(30:22) The Lateral Transfer to the Navy
(31:11) Mini BUDs and 100 Officers Competing
(33:02) Hell Week and a Friend’s Son at BUD/S Now
(36:29) Officers and Enlisted on the Same Crew
(37:38) Diving School and Almost Drowning
(40:07) Checking In and First Deployment to Ramadi
(43:38) The 2006 Battle of Ramadi and the Band of Brothers
(45:54) Sniper Overwatch for the Army
(48:17) The Last Mission Before Rotating Home
(49:39) 115 Degrees on the Rooftop
(53:31) Playing Through Injury
(58:15) The Grenade Hits the Roof
(59:39) Michael Monsoor Jumps on the Grenade
(01:04:13) Crawling for the Radio Under Fire
(01:06:41) Loaded Into the Bradley
(01:08:15) Saying Goodbye to Mikey
(01:09:45) Meeting Mikey’s Mother
(01:11:13) The Extent of His Injuries
(01:15:52) Switching Name Tags to Redeploy
(01:16:45) The Battle of Sadr City
(01:18:58) Applying for DEVGRU Selection
(01:20:58) The Psychology of DEVGRU Screening
(01:24:21) The Speed of DEVGRU CQB
(01:25:45) The Night Adam Brown Was Killed
(01:29:45) Carrying Adam’s Body Down the Mountain
(01:31:00) Why the Mission Comes Before Family
(01:32:19) Delta Versus DEVGRU
(01:33:36) Divorce and a Tour at Texas
(01:37:29) Retiring Without a Ceremony
(01:38:51) Becoming a Fox News Contributor
(01:45:30) Founding Talent War Group
(01:47:15) Selling the Company to Overwatch
(01:48:44) What Overwatch Mission Critical Does
(01:51:22) China and Data Center Misinformation
(01:54:15) The Truth About Water and Power
(01:59:41) The Cibolo Town Hall Bloodbath
(02:02:34) The Case for Small Modular Reactors
(02:03:25) How Triple Seven Started
(02:08:34) Should We Be in Iran
(02:14:45) The Maduro Raid in Venezuela
(02:16:14) Reacting to the Delta Force Raid
(02:18:27) Drone Warfare and Unit Economics
(02:22:56) Blue Collar Millionaires and Forge Now
(02:28:57) The Eddie Gallagher Case
(02:32:19) Investigated by NCIS
(02:39:14) Announcing His New Book Teams
(02:47:37) Host Outro and Subscribe
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The Doctor Who Got Sick 22 Times Before Anyone Asked Why | Dr. Clay Moss
2026/09/18
Clay Moss looked like the healthiest guy at Ole Miss. He trained six days a week and got strep throat every other month for four straight years. Twenty-two documented cases. Every visit ended the same way: a steroid shot, a round of antibiotics, see you next time. Nobody asked how he was sleeping, what he was eating, or how much caffeine he was running on.
He got his tonsils out after graduation. Six weeks later he had the worst strep of his life.
Then medical school in Jackson, Mississippi, the only MD program in the state. He watched classmates go from all-nighters to Adderall to Xanax to sleep aids to antidepressants, and by fourth year he was sitting in the lecture hall where it all started, listening to fifteen of them compare prescriptions. When a doctor offered him Xanax for the panic attacks he had been having since sophomore year of college, he said no and started with sleep, food, meditation, and blood work instead.
This week I sat down with Dr. Clay Moss, a Gulf Breeze kid who used to peek through the fence at the Andrews Institute on the walk home from middle school. We get into the 12.5-hour surgery that ended his surgeon dream four hours in, opening his Match Day letter on stage, why your doctor only gets 5 to 12 minutes with you, and what happened to him after the COVID booster that he didn’t feel he could say out loud in med school.
We also get into the stuff you can use tomorrow. Why he picks the barbell over the treadmill, why a broken hip after 65 is so dangerous, hormone therapy for women, sun versus sunscreen, tap water, low-dose lithium, and what four sauna sessions a week does for you.
Clay has ten months of residency left and 800,000 people following his work. Then he opens the practice 18-year-old Clay needed. Hope you guys enjoy this one.
Follow Clay: @drclaymoss
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”
AMP Fitness: amp.ai/rideout
Ken’s book now available here: https://www.theothersideofhard.com/
Chapters
(00:00) Meet Dr. Clay Moss
(00:15) Growing Up in Gulf Breeze
(01:15) Dad’s Houseboat in Pensacola
(02:23) Peeking Through the Andrews Fence
(04:19) ROKA Sunglasses for Clay
(05:49) The Only MD School in Mississippi
(06:27) Trauma Surgery Rotation
(08:32) The Teacher Who Said Never
(09:13) Ken Meets the Panhandle
(11:13) Sponsor Break ROKA
(13:27) Sixty Percent Out of State
(15:22) Chasing Good Mentors
(16:17) No Such Thing as Optional Practice
(18:34) Rushing Sigma Chi
(19:56) Psychological Hazing
(23:00) Nike Sponsors Sorority Rush
(24:26) The Face of Functional Medicine
(26:43) Five to Twelve Minutes Per Patient
(27:32) Paying for Your Own Doctor
(28:36) Fighting Insurance Denials
(30:52) Twenty Two Cases of Strep
(32:17) Nobody Asked About Sleep
(33:14) The Practice 18 Year Old Clay Needed
(35:23) Pay Me Now or Pay Me Later
(36:58) Cash Pay Doctors Are Not Selfish
(38:33) Sponsor Break AMP
(39:29) Florida State Took 190 of 10000
(40:27) Meditation and Lifting in Jackson
(40:47) All Nighters to Adderall
(41:38) Fifteen Classmates on Antidepressants
(44:42) Jelly Roll on Haters
(45:50) Cold Calling the DMs
(47:21) The Early Huberman Comparison
(49:43) Drinking From a Firehose
(51:09) The Twelve and a Half Hour Surgery
(52:15) Finding Physical Medicine and Rehab
(53:47) Match Day on Stage
(55:58) Ten Months Left
(56:58) A Fifty Patient Practice
(58:55) Five Grand a Month for Insurance
(01:00:46) Questioning Everything After Covid
(01:02:22) The ER Visits He Could Not Talk About
(01:03:26) First Panic Attack in Tallahassee
(01:04:40) Turning Down the Xanax
(01:05:43) Propranolol as a Safety Net
(01:07:30) Cardio Versus Strength
(01:08:56) Muscle as a Glucose Sponge
(01:10:22) Ken’s VO2 Max at 55
(01:12:05) Breaking a Hip After 65
(01:13:45) Women Need the Barbell Most
(01:15:24) Why HRT Got Demonized
(01:17:53) Absolute Versus Relative Risk
(01:20:31) Regrowing an Optic Nerve
(01:22:49) Know Why You Take It
(01:25:31) Sun Versus Sunscreen
(01:28:48) Low Dose Lithium
(01:31:08) Never Drink Tap Water
(01:33:19) Sauna Four Times a Week
(01:37:55) Not Running for Anyone Else
(01:39:55) The REP Fitness Garage Gym
(01:43:37) Ken’s Trip to Mexico
(01:45:31) Ken’s DMT Experience
(01:49:50) A Grandfather’s Secret
(01:53:25) Tune Out the Negativity
(01:53:51) Host Outro and Subscribe
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Too Small for the NFL. Then He Broke a Chiefs Record. | Dexter McCluster
2026/09/16
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
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From a Prison Cell to Nike Brand Director | Jordan Rogers
2026/09/11
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
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From Compulsive Gambler to a $465 Million Exit | Rich Galgano
2026/09/09
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 f*****g 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
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19 Million Followers, Losing Everything, and Starting Over in Nashville | Tayler Holder
2026/09/04
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
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The Rise, Fall, and Reinvention of an Olympic Champion | Missy Franklin
2026/09/02
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
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International Fugitive to UFC Top 10 | Ian Heinisch
2026/08/28
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
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Brutal Hits, Broken Bodies & the Business of Football | Bernard Pollard
2026/08/26
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
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The Cop Who Went to Prison for 19 Years | Kent McGowen
2026/08/21
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
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The Wall Street Executive Who Had Everything—Except Peace | James “Jet” Davies
2026/08/19
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
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From Small-Town Kid to Everest, Equinox & IRONMAN CEO | Scott DeRue
2026/08/14
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
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Podcast reviews
Read RIDEOUT: The Other Side of Hard podcast reviews
RoycePhillips1 2026/09/25
Must-listen shows!
I have listened to hundreds of podcasts throughout the years, typically on long runs and long car rides. I absolutely love this podcast and really bel...
Trace1502 2026/09/17
Two great men!
I loved the episode with Dexter
samgrenus 2026/09/06
Perfect for long runs!
I just found this podcast a few weeks ago and absolutely LOVE the diversity of guests. It feels like a true conversation and not an interview. Perfect...
william of occam 2026/08/21
Love it
Came for the Mickey Ward interview then discovered a great show! Ken is a great interviewer and keeps getting better - I think he’s a very good listen...
Ipad user 767676 2026/08/06
54 y/o executive athlete: On my required listening list.
Ken makes himself vulnerable to his audience and his guests, and in doing so he lights a path to a healthy, productive, and genuinely fun mindset — on...
Simulink2 2026/06/28
Inspirational and Raw
I learned so much from this podcast. It was reassuring to realize I’m not the only “psycho sports Dad” out there and that I probably need to chill out...
racingintothefuture 2026/06/05
Go Green
Great interview! Great show
mattymogs 2026/05/14
Love the pod
Must listen every time the pod drops - keep it up!
brokenrunnr 2026/02/07
🙌
The podcast I’ve been waiting for since Ken joined Nick Bare on the Bare Performance Podcast a few years back. Keep up the great work, Ken!
The Grand Porcini 2026/01/01
Realest Podcast I Follow!
I’ve known Ken for 15 years and unlike other podcasts, there’s NO BS to be found here. What I like the most is how he lets his guests be the star of t...
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