RIDEOUT: The Other Side of Hard

James “Jet” Davies spent more than two decades inside high finance, eventually becoming CEO of Deutsche Bank’s broker-dealer for the Americas. But behind the titles, money, and success was a life that was beginning to unravel.

James joins Ken to trace the entire path—from growing up in London and attending an elite all-boys school, where he experienced emotional and sexual abuse, to studying law at Bristol after being rejected by Oxford, entering one of London’s top law firms, and eventually making the leap to Deutsche Bank.

He takes Ken inside the brutal culture of London trading floors, the explosion of derivatives, the 2008 financial crisis, and the strange reality of climbing higher while questioning whether any of it was making him happier.

Then, in 2019, James crashed. He opens up about self-harm, therapy, his marriage reaching a breaking point, and the process of separating his identity from money and status. When Deutsche Bank ultimately chose not to extend his contract in 2024, the career he had spent nearly 25 years building was suddenly over.

Instead of going back, James and his partners bought an 85-acre campus in the Berkshires and transformed it into The Time—a retreat space built around nature, connection, and creating the kind of reset James once desperately needed himself.

It’s a conversation about ambition, trauma, money, rejection, burnout, and what happens when achieving everything you thought you wanted still isn’t enough.

Thank you to our sponsors

Our Title Sponsor ROKA: www.roka.com/ Code “RIDEOUT”

Wild Roman: wildroman.com/rideout Code “RIDEOUT15”

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

Chapters

(00:00) Meet James Jet Davies

(00:30) Strava Rivalry Origins

(01:39) Marathon Times Talk

(02:14) London Roots and Schooling

(03:09) Inside Elite Boys School

(06:02) Abuse and Trauma Unpacked

(07:52) Therapy and Healing Stages

(10:10) How Predators Gain Access

(12:28) Roka Eyewear Sponsor

(14:08) Warning Signs at Boarding

(15:42) Strict Discipline and Bullying

(17:04) Single Gender School Effects

(18:59) American Schools and Parenting

(22:21) Secondary School Shift

(27:49) Competition Winners and Losers

(28:56) Sports and the Jet Nickname

(30:06) Parents Expectations and Success

(31:21) Finding Your Own Path

(32:35) Loving Work Now

(33:09) Parents Pushing Kids Away

(34:17) Trauma Surgeon Passion

(35:57) Skincare Ad Break

(36:58) Oxford Rejection Story

(39:57) Brutal Oxford Interviews

(43:34) Setbacks Build Resilience

(45:37) Bristol And Posh Crowd

(46:08) Law Firm Pipeline

(47:45) Derivatives And Leverage

(49:35) Market Manipulation Rant

(52:37) Deutsche Bank Jump

(57:54) Legal Dept Vs Traders

(59:02) Breaking Into Trading Desk

(01:00:16) UK Trading Floor Vicious

(01:00:53) Trading Floor Hazing

(01:02:51) London Finance Wild West

(01:04:50) Back to Legal and Redemption

(01:06:43) Structured Finance Explained

(01:07:45) Crisis Unwinding and Promotions

(01:10:46) Post Crisis Pay and Talent Shift

(01:14:09) New York Move and Culture Shock

(01:17:13) American Optimism vs UK Cynicism

(01:23:46) 2019 Leadership Pressure Cooker

(01:26:43) Mental Health Crash in Finance

(01:29:53) Self Harm Confession

(01:31:23) Therapist And SSRIs

(01:32:50) Couples Session Breakthrough

(01:33:55) COVID Reset And Career Shift

(01:36:51) Leaving Deutsche Bank

(01:40:31) Buying Berkshire Retreat Campus

(01:45:04) Running Thyme Retreats

(01:46:26) Hospitality Lessons And Rules

(01:49:13) Upcoming Running Retreat Promo

(01:53:48) Life After Finance Mindset

(01:58:30) Wrap Up And Subscribe

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

Scott DeRue has spent his life creating experiences that push people beyond what they thought was possible.

Ken sits down with his longtime friend and current CEO of The IRONMAN Group to talk about growing up in small-town North Carolina, being told during his first performance review that he “wasn’t smart enough,” walking away from a lucrative consulting career in search of purpose, becoming a University of Michigan professor and eventually the youngest dean of a top business school, and leaving the security of academia to help lead Equinox through the COVID crisis.

Scott also shares how mountaineering became one of the defining forces in his life, what it took to climb Everest and complete the Seven Summits, the terrifying risks of the Khumbu Icefall and descent from Everest, and why getting to the summit is only half the job.

Now leading The IRONMAN Group, Scott explains why he believes the company is ultimately in the “dream fulfillment business,” what he learned from rebuilding Equinox, why athlete feedback matters, and the decision to bring the men’s and women’s IRONMAN World Championship back together in Kona.

Ken and Scott also revisit the 2023 Gobi March in Mongolia—the race where they first met and Ken somehow went from having never run an ultramarathon or camped to winning the entire thing.

Thank you to our sponsors

Our Title Sponsor ROKA: www.roka.com/ Code “RIDEOUT”

AMP Fitness: amp.ai/rideout

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

Chapters

(00:00) Scott DeRue Intro

(00:32) Gobi March Bond

(01:46) Small Town Roots

(02:02) Schoolwork And Drive

(05:08) Sports And Pole Vault

(06:05) UNC And Water Skiing

(09:08) From Bio To Business

(09:46) Boston Consulting Start

(11:16) Sponsor Break Roka

(12:56) Brutal Review Lesson

(18:41) Quarter Life Crossroads

(21:02) PhD Path To Michigan

(25:58) Rapid Rise To Dean

(28:34) Transformational Teaching

(30:43) Money Vs Purpose

(32:41) Restroom Empire Moment

(34:43) Loving the Work

(35:04) From Professor to Dean

(37:26) Youngest Dean Pressure

(38:52) Mission Driven Leadership

(40:28) Sponsor Break Amp

(41:04) Mountaineering Origin Story

(46:16) Seven Summits Quest

(50:02) Everest Risks and Resilience

(52:18) Khumbu Icefall Focus

(55:46) Summit and Descent Dangers

(01:03:35) Equinox During Covid

(01:08:51) Rebuilding and Ironman Pull

(01:10:13) Ironman Obsession

(01:10:43) Taking the CEO Call

(01:11:50) Ironman Beyond Triathlon

(01:12:51) Lifestyle and Identity

(01:15:03) Feedback and Responsibility

(01:15:33) Kona War Stories

(01:18:00) Dream Fulfillment Mission

(01:20:38) Kona Together Again

(01:22:10) Designing Wave Starts

(01:24:44) Midnight Finish Magic

(01:29:43) Will He Race One

(01:30:20) Gobi March Memories

(01:34:04) Wild Characters and Lessons

(01:39:27) Gratitude and Wrap Up

(01:40:23) Subscribe and Sponsors
Learn more about your ad choices. Visit megaphone.fm/adchoices

Taylor Cavanaugh’s life has been a cycle of achievement, self-destruction, and rebuilding.

Before becoming a Navy SEAL, Taylor had already been expelled from school, arrested repeatedly, survived a violent car crash, and served time in county jail. After multiple branches of the military turned him away, the Navy finally gave him a shot.

Taylor made it through BUD/S and Hell Week and eventually served with SEAL Team 7 as a communications specialist, JTAC, and sniper. His deployments took him to Yemen and Iraq, where he called airstrikes, worked alongside local forces, and operated under rocket and mortar fire.

But outside the teams, the same patterns that had followed him since his teenage years never fully disappeared. An aggravated assault case nearly sent him to prison. Another alcohol-fueled incident and a positive steroid test eventually ended his SEAL career.

Civilian success followed, but so did Adderall, Xanax, opiates, and eventually fentanyl. Taylor went from working in real estate development and venture capital to withdrawing alone in Hawaii, living out of his truck, nearly broke and contemplating suicide.

Instead of ending his life, he bought a one-way ticket to France.

Taylor walked through the gates of the French Foreign Legion, surrendered his passport, was given a new identity, and started again at the bottom. He spent years running, cleaning toilets, training in the French Alps, deploying to Estonia and conducting jungle operations against illegal gold mining operations in French Guiana.

Today, Taylor has turned the discipline that helped rebuild his own life into a coaching business focused on consistency, personal responsibility, and controlling the controllables.

This is Taylor Cavanaugh’s story. Follow Taylor: @tcavofficial

Thank you to our sponsors

Our Title Sponsor ROKA: www.roka.com/ Code “RIDEOUT”

Wild Roman: wildroman.com/rideout Code “RIDEOUT15”

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

Chapters

(00:00) Meet Taylor Cavanaugh

(00:20) Gloucester Rough Edges

(01:27) Marine Base Upbringing

(01:48) Pilots And Air Ops

(04:53) JTAC Danger Close

(07:38) High School Hustle

(09:26) College Chaos And Crash

(11:49) Rain Means Change

(14:09) County Jail Reality

(17:06) Sponsor Break Roka

(19:43) Denied Then Navy Shot

(22:56) BUDS Cold And Hell Week

(29:26) Darkest Conditioning Runs

(30:26) Running Form and Gait

(31:54) Marathon Mindset Curse

(33:03) Gobi Desert Stage Race

(34:57) Skincare Ad Break

(36:29) Joining SEAL Team 7

(37:19) Peer Evals and Rankings

(38:18) Comms and JTAC Track

(41:10) Sniper School and Stalking

(45:10) Low Vis Intel Ops

(46:54) Yemen Deployment Tension

(48:56) Iraq Rockets and Base Build

(52:32) Assault Charge Fallout

(55:19) Court Deal in Boise

(57:21) Paying Restitution Hard

(57:48) Jail Then Back To Training

(58:39) Probation In SEAL Life

(01:00:13) Jimmy Buffett Golf Cart Bust

(01:02:03) Steroid Test Career Fallout

(01:06:22) Leaving Teams For Construction

(01:07:27) Adderall Xanax Spiral

(01:09:28) Opiates Return Then Fentanyl

(01:12:32) High Functioning VC Hustle

(01:16:07) Hawaii Withdrawal And Acid Ride

(01:19:07) Homeless Suicidal Turning Point

(01:23:03) One Way Ticket To Legion

(01:24:43) Paris Hostels And Legion Gate

(01:26:38) Passport Taken New Identity

(01:27:23) Gate Shock Pullups Test

(01:29:11) Barracks Vibes Recruit Types

(01:30:34) Kenyan Runner Visa Hack

(01:33:37) Gestapo Interviews Selection

(01:36:32) Starting Over Cleaning Toilets

(01:38:04) French Guiana Jungle Ops

(01:40:39) Ukraine War Estonia Deployment

(01:44:48) Barracks Fights Discipline

(01:49:36) Legion Running Culture

(01:52:34) Amazon Survival Gold Mines

(01:55:19) Gold Flakes Oil Bugs

(01:56:11) Amazon Jungle Hellscape

(01:57:11) Thriving in Humidity

(02:00:13) Running Shoes and Boots

(02:01:57) Social Media Sparks Exit

(02:12:32) Discipline and Agency

(02:18:00) Coaching and Consistency

(02:23:33) Closing Thanks and Plugs
Learn more about your ad choices. Visit megaphone.fm/adchoices

McKinnon Galloway was diagnosed with NF2 at 16 after a routine MRI for a volleyball concussion revealed two brain tumors. What followed was years of chemotherapy, a phase-one clinical trial, four brain surgeries, radiation, facial paralysis, a cerebral stroke, and the complete loss of her hearing.

Her third brain surgery became life-threatening when doctors discovered that her tumor had developed an extensive blood supply. McKinnon nearly bled out, woke up fully deaf, and learned that complications had prevented surgeons from placing the auditory brain implant she expected to receive. Months later, another surgery left her struggling to walk and unable to move one side of her face.

McKinnon also opens up about her father’s alcoholism and suicide, the strength she inherited from her mother, the realities of navigating healthcare and insurance, and the daily isolation that can come with deafness.

Rather than disappearing into everything she lost, McKinnon built a platform that bridges the deaf and hearing worlds. Now followed by more than one million people across social media, she advocates for better deaf technology, clearer patient communication, and a more personal approach to medicine through her mission of “Humanizing Healthcare.”

Follow McKinnon on Instagram: @mckinnongalloway

Thank you to our sponsors

Our Title Sponsor ROKA: www.roka.com/ Code “RIDEOUT”

AMP Fitness: amp.ai/rideout

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

Chapters

(00:00) Meet McKinnon

(00:48) Living With NF2

(02:26) Growing Up Charlotte

(04:20) Diagnosis At Sixteen

(05:44) First Brain Surgery

(08:16) Recovery And Questions

(10:30) Roka Eyewear Sponsor

(12:15) Costa Rica Sea Turtles

(13:42) College And Family Strain

(15:34) Trials Second Surgery

(18:14) Losing Hearing Completely

(20:55) Third Surgery Near Death

(25:09) Deafness And Implants

(27:08) Post Op Complications

(30:56) Surgery Complications

(32:54) Sponsor Break Amp

(33:39) Mom Teaches Independence

(35:37) Dad Addiction Spiral

(40:55) Losing Her Father

(45:03) Faith Trip Bethlehem

(47:46) Radiation And Recovery

(53:29) MRI Scare And Boston

(57:20) Living With NF2

(59:51) Marriage And Work Talk

(01:00:50) Insurance Costs Reality

(01:02:44) Ambulance Bill Fight

(01:03:48) Fees Everywhere Now

(01:05:14) Tipping Gone Wild

(01:06:18) Driving While Deaf

(01:07:43) Handicap Parking Clash

(01:10:01) Hardest Part Socializing

(01:11:48) Hope for Nerve Repair

(01:13:20) Deaf Tech Advocacy

(01:14:00) Social Media Origin Story

(01:17:06) Handling Online Trolls

(01:19:49) Perks of Being Deaf

(01:24:14) Humanizing Healthcare Mission

(01:26:49) Authentic Content Approach

(01:28:53) Brand Deals and Contact

(01:29:53) Daily Work and Pivots

(01:31:02) Wrap Up and Subscribe

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

Mishka Shubaly has lived several lives: gifted student, touring musician, Columbia-trained writer, addict, shipwreck survivor, ultrarunner, Yale professor, and the editor who helped Ken Rideout turn his life into a book.

Mishka joins Ken for a deeply personal conversation about growing up with a distant father, leaving home for college at 15, surviving a deadly school shooting, and watching his family lose everything shortly afterward. He recounts years of destructive drinking and drug use, getting shipwrecked in the Bahamas, walking for miles without food or navigation, and drinking his own urine shortly before being rescued.

They also discuss the realization that finally pushed Mishka toward sobriety, the furious first run that changed his life, becoming an ultramarathoner, nearly joining a reality dating show, and how a cold email led Jeff Bezos to write the foreword to his book. Ken and Mishka reflect on addiction, anxiety, ambition, friendship, marriage, and the difficult process of believing that the life you have built might finally be enough.

Thank you to our sponsors

Our Title Sponsor ROKA: www.roka.com/ Code “RIDEOUT”

Wild Roman: wildroman.com/rideout Code “RIDEOUT15”

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

Chapters

(00:00) Mishka Joins the Show

(00:44) Writing the Book Together

(02:09) Authenticity Over Advice

(03:57) Running Shoe Rabbit Hole

(08:31) Frugal Life and Family Roots

(12:48) Sponsor Break Roka Eyewear

(14:24) Kids and Wastefulness

(17:46) Sober Anxiety and Control

(21:57) Ibogaine and Rewiring the Brain

(23:29) Mishka’s Upbringing and Rocket Scientist Dad

(27:34) Family Struggles and Parenting Reflections

(32:42) Sponsor Break Wild Roman Skincare

(33:46) Divorce Year and Dad Moves Away

(34:39) Early College Leap

(35:35) Fights and Trouble

(36:02) Campus Shooting Trauma

(38:29) Divorce and Downward Spiral

(44:35) Addiction and New Perspective

(48:50) Success and Enough

(51:39) Family Pressure and Anxiety

(57:36) From Acting to Writing

(59:09) Dad Fallout and No Kids

(01:03:46) New York and Columbia MFA

(01:06:34) Playing It Cool

(01:07:12) Celebrity Sauna Stories

(01:09:31) Columbia Encouragement

(01:11:40) Ivy League Aid Debate

(01:13:33) Loans And Burnout

(01:15:12) Music Life And Hoarding

(01:18:39) Shipwreck Setup

(01:22:06) Running Aground

(01:25:30) Survival Walk Breakdown

(01:30:44) Rescue And Aftermath

(01:33:39) SEAL Prep Coincidence

(01:35:46) Dating Show Tease

(01:36:05) Reality Show Doubts

(01:37:58) Dark Side of Reality TV

(01:40:13) Lawyer Negotiation Tactics

(01:42:20) Dodging the Dating Show

(01:44:36) Sobriety Turning Point

(01:48:49) First Furious Run

(01:52:55) Ultra Lessons and New Highs

(01:54:39) Kenya Stage Race Adventure

(01:57:09) Love as the New Anchor

(01:58:54) Withdrawal and Anxiety Hell

(02:01:49) What’s Next Creatively

(02:04:15) Bezos Foreword Story

(02:06:44) Final Thanks and Subscribe
Learn more about your ad choices. Visit megaphone.fm/adchoices