RIDEOUT: The Other Side of Hard

Kaitlyn Bristowe went from a small town in Canada to the center of reality TV—and paid the price for it.

She opens up about chasing a dance career, hitting rock bottom after a breakup, and rebuilding her life from nothing. Then came The Bachelor and The Bachelorette—and with it, fame, manipulation behind the scenes, and a level of public backlash that nearly broke her.

She talks about being slut-shamed on national TV, dealing with threats, and navigating the pressure of building a career in a space that didn’t exist yet.

But she didn’t stop there.

From Broadway to building a business, writing music, and ultimately winning Dancing With the Stars, Kaitlyn shares how she turned chaos into momentum—and why doing the inner work mattered just as much as the external success.

This is a conversation about identity, resilience, and staying true to yourself when the world is trying to define you.

Thank you to our sponsors

Ketone-IQ: ⁠ketone.com/rideout Code “RIDEOUT”

Helix Sleep: http://helixsleep.com/rideout for 20% off

Athletic Brewing: https://athleticbrewing.com/ Code "RIDEOUT"

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

Chapters

00:00 Welcome and Reality Stigma

00:49 Instagram Early Days

02:07 Brand Deals and Trust

03:11 Influencer Culture Shift

05:22 Small Town Roots

06:37 Dance Dream to Vancouver

07:20 College Blueprint Debate

10:16 Hockey Life and Rock Bottom

12:50 Signed Up for The Bachelor

13:30 Adversity and Mental Health

15:31 Bachelor Night One Chaos

18:13 Bali Blindside Elimination

21:26 Becoming The Bachelorette

22:13 Negotiating the Contract

25:14 Bachelorette Behind the Scenes

26:31 Sex Talk and Producer Manipulation

30:24 Backlash and Mean Tweets

31:25 Trolls And Triggers

32:42 Reality TV Relationship Fallout

34:16 Post Show Career Whiplash

34:54 Broadway Dream And Burnout

37:11 Paparazzi And Being Recognized

37:50 Sponsor Break Athletic Brewing

38:43 Broadway Nerves And Mom Moment

39:57 DWTS Drama And Contract Twist

42:39 Winning DWTS Through Injury

47:55 Freestyle Finale And Nev Beef

49:46 Staying True And Inner Child Work

56:28 Hoffman Process And Self Dates

01:00:07 Psychedelics And Ego Death Story

01:02:25 Closing Thoughts And Subscribe
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Phillip Frankland Lee went from washing dishes to building one of the most unique restaurant empires in the world. But it didn’t happen clean.

He was betrayed by a business partner who disappeared, leaving him with debt and lawsuits. He got hit with a $15M legal battle from private equity. His restaurants were shut down overnight during COVID.

And instead of folding, he doubled down.

In this episode, Phillip breaks down how he turned Sushi by Scratch into a full sensory “show,” why he believes great food should hit even if you’re not a foodie, and how relentless work ethic—from punk rock touring to Michelin kitchens—shaped everything he built.

This is a story about obsession, resilience, and refusing to lose—no matter how many times the game resets.

Thank you to our sponsors

Ketone-IQ: ⁠ketone.com/rideout Code “RIDEOUT”

Athletic Nicotine: athleticnicotine.com/rideout Code "RIDEOUT"

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

Chapters

(00:00) Meet the Sushi Showman

(00:31) Concert vs Show Dining

(02:27) Speakeasy Vibe Origins

(05:25) Ten Seats Omakase Flow

(06:55) Sushi Obsession at 13

(11:01) Family Drive and Discipline

(14:54) From Bands to Dish Pit

(18:49) Quitting Culinary School

(21:34) Kitchen Culture and Leadership

(26:58) First Sous Chef Reality

(31:28) Michelin Standards at Hatfield's

(35:43) Chicago Three Star Leap

(37:42) Chef Ride Stories

(39:18) Chicago Kitchen Lessons

(40:49) LA Proposal Reset

(41:02) Tasting Menu Delivery

(43:10) Scratch Bar Deal

(46:18) Critics And Standards

(47:53) Coffee Shop Fallout

(49:50) Apartment Pop Up

(51:31) Beverly Hills Move

(52:51) Jonathan Gold Boost

(55:36) Health Scare Pivot

(58:05) Food Network Wins

(59:02) Top Chef Controversy

(01:06:17) Partner Betrayal

(01:10:48) New Backer Rebuild

(01:14:46) Pandemic Survival Mode

(01:17:10) Austin Pop Up Breakthrough

(01:17:34) Rogan Sells Out February

(01:19:23) Austin Popup Becomes Permanent

(01:20:23) Private Equity Deal Trap

(01:22:20) Hit With $15M Lawsuit

(01:28:03) Opening 30 Restaurants to Survive

(01:30:06) Four Acre Michelin Dream

(01:36:14) Hunting and Whole Animal Cooking

(01:46:35) Nashville Burger Launch

(01:49:43) Mindset Gratitude and Follow Through

(01:53:22) Closing Thanks and Subscribe
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Sam Parr built one of the most influential media companies of the last decade, but the path there was anything but clean.

Before selling The Hustle to HubSpot, Sam was getting arrested, struggling with alcohol abuse, and bouncing between odd jobs- from running a hot dog stand in Nashville to chasing a job at Airbnb that fell apart after a lie caught up to him.

This conversation traces the full arc.

From Division I track athlete to dropout. From drunk and directionless to building a media empire. From rock bottom to getting sober through a San Francisco clinic that changed his life.

We get into:


The real math behind building and selling The Hustle


Why owning an email list beats chasing algorithms


The psychology of fear, networking, and taking swings


How Hampton became a $15K/year network for elite founders


What addiction actually looked like — and how he got out

This is a story about obsession, proximity, risk, and rebuilding — not just once, but multiple times.

Thank you to our sponsors

Ketone-IQ: ⁠ketone.com/rideout Code “RIDEOUT”

Timeline: timeline.com/rideout Code "RIDEOUT"

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

Chapters

(00:00) Money Talk Icebreaker

(01:54) Nerding Out and Self Belief

(04:06) Track Star Origins

(04:53) Pickers and Hot Dog Hustle

(06:33) Airbnb Lie and Rock Bottom

(08:20) Bunk to HustleCon Breakthrough

(09:46) Anti MBA Networking Playbook

(12:54) Passion and Being Yourself

(15:05) From Events to The Hustle

(16:04) Newsletter Math and Scaling

(19:08) Exit Numbers and Luck

(20:13) Owning the Inbox Insight

(23:32) Fear and Fighting Mindset

(27:38) Boxing Gym Lessons

(30:36) Mitochondria Aging Boost

(31:30) Selling The Hustle

(32:05) HubSpot Media Model

(34:14) Meeting His Wife

(37:40) Immigrants And Politics

(43:37) Patriotism And Denim

(45:01) Building Hampton Network

(49:42) Pricing And Peer Value

(51:48) Getting Sober Story

(54:37) Failures And Parenting Scare

(58:25) Maced While Handcuffed

(59:05) Son’s Concussion Scare

(01:00:37) Bike Crashes and Morphine

(01:04:39) Seal Stories and Real Toughness

(01:08:01) Regret Not Enlisting

(01:09:18) Entrepreneur Advice and Proximity

(01:10:41) Networking Without Networking

(01:11:48) Cold Email Done Right

(01:15:47) Haters and Mean Comments

(01:20:02) Writing and Selling the Memoir

(01:25:57) Bro Talk and Wrap Up

(01:28:21) Subscribe and Book Links
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Oz Pearlman is one of the most recognized mentalists in the world—but behind the “mind-reading” is something much deeper.

In this episode, we go beyond the tricks. We talk about marathon psychology, the obsession it takes to shave minutes off your time, and the mindset required to win—whether it’s on the course, on stage, or in life.

Oz opens up about his upbringing, hustling through college, and building a career from nothing—performing magic in restaurants, learning human psychology, and turning rejection into opportunity. He breaks down how he reads people, builds relationships, and creates moments that feel impossible.

We also dive into connecting with people the right way, why most people approach it wrong, and how giving value first changes everything.

This is a conversation about discipline, obsession, and mastering your craft—whatever it is.

Thank you to our sponsors

Ketone-IQ: ⁠ketone.com/rideout Code “RIDEOUT”

Rho: https://rhonutrition.com Code "RIDEOUT"

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

Chapters

(00:00) Meet Oz Pearlman

(00:36) Marathon PR Mindset

(03:02) Winning Races Psychology

(05:42) Training Slumps Comebacks

(08:22) Why Running Feels Good

(11:36) Origins Midwest Roots

(12:33) School Skips Siblings

(15:57) Parenting Chaos

(19:06) Abuse Discipline Debate

(24:51) Engineering Divorce Magic

(26:57) Hustling Paying Tuition

(28:32) Money Class Upbringing

(29:13) Compare and Despair

(29:58) Work Ethic and Values

(31:58) Blaine and Street Magic

(33:12) Restaurant Magic Lessons

(36:00) Learning Tricks and Gimmicks

(38:35) Impromptu Superman Mindset

(41:30) Mentors and Time Value

(43:55) Marathon Mind Games

(47:44) College Hustle and Numbers

(50:08) Penguin Magic Breakthrough

(52:37) Repackaging Mentalism

(55:02) Critics and Ethics

(57:43) High Stakes Debuts

(58:44) Magic Is the Point

(59:27) Selling a Success Guide

(01:01:21) Handling Haters

(01:02:33) When Tricks Fail

(01:04:12) Notes and Repeat Clients

(01:06:34) Building Real Networks

(01:11:33) Lead With Give

(01:17:27) Earning Attention

(01:18:56) Big Break and White House

(01:24:54) Closing and Subscribe
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Steve Weatherford: From Super Bowl Champion to Rock Bottom, Addiction, and Redemption

Ken sits down with Super Bowl–champion punter Steve Weatherford for a conversation about identity, rejection, addiction, and what happens when success doesn’t fix anything.

Steve shares his journey from a driven, insecure kid chasing approval through sports to becoming one of the best in the world—earning a scholarship to Illinois, grinding through the NFL as an undrafted player, getting cut multiple times, and eventually winning a Super Bowl with the New York Giants. But even at the top, with money, recognition, and a $13M contract, he found himself empty and searching for more.

He opens up about the parts of his life most people never see: childhood trauma, ADHD and rejection, sexual abuse, and the early roots of addiction. That pain followed him into adulthood—fueling porn addiction, painkiller use, infidelity, and a double life that nearly cost him everything, including his marriage and his life.

Steve recounts the brutal reality of getting cut in the NFL, losing his identity, and hitting rock bottom—culminating in isolation, depression, and suicidal thoughts. What followed was a long, uncomfortable process of confronting his past, rebuilding his identity, and redefining what success actually means.

This is a conversation about chasing validation, the dark side of achievement, and the realization that winning doesn’t always feel like winning. It’s also about rebuilding—faith, family, fatherhood, and learning to live with purpose instead of proving something.

Thank you to our sponsors

Ketone-IQ: ⁠ketone.com/rideout Code “RIDEOUT”

Rho: https://rhonutrition.com Code "RIDEOUT"

Athletic Nicotine: https://www.athleticnicotine.com/ Code "RIDEOUT"

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

Chapters

(00:00) Welcome and Book Launch

(00:53) Success Pressure and Presence

(02:48) Worthiness and Relationships

(06:32) Origin Story Louisiana

(07:18) Track Club and Drive

(11:43) Soccer to Football Kicker

(15:10) Butt Cheek Field Goal Tale

(18:34) Never Quit and Gratification

(22:06) Illinois and Decathlon Path

(28:18) NFL Break In Saints Camp

(32:32) Getting Cut Identity Crash

(37:02) Street Preacher Turning Point

(40:48) Waiver Wire Whiplash

(42:22) Rejection and Galatians

(43:53) Late Bloomers Mindset

(46:27) Trauma and Testimony

(50:52) Fatherhood and Identity

(53:36) Addiction Roots and ADHD

(01:00:18) Power Team Salvation

(01:08:44) Grooming and Aftermath

(01:17:15) Super Bowl Emptiness

(01:26:37) Retirement and Rock Bottom

(01:32:13) Back to Church

(01:33:49) Pastor Calls Him Out

(01:35:51) Last Resort Faith

(01:36:12) Desert Mens Retreat

(01:39:14) Lightning Bolt Encounter

(01:42:40) Releasing Trauma to God

(01:44:53) Confession and Coaching

(01:47:29) Door Slam Move Texas

(01:51:19) Called to Lead Men

(01:53:26) Launching Pad Grows

(02:00:52) Ken Faith Journey

(02:11:39) Grind Versus Grace

(02:16:53) Salvation Prayer

(02:20:18) Conclusion
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