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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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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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

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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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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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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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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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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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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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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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