RIDEOUT: The Other Side of Hard

Andrew Yang joins me for a conversation about politics, AI, entrepreneurship, and why he believed he had to run for president.

We talk about what pushed him from the private sector into national politics, what he learned from meeting former presidents, and why he came away convinced that the people leading the country are not superhuman. Andrew opens up about the reality of running a presidential campaign, from building a team and raising roughly $40 million to making seven debate stages and breaking through with independent media.

We also get into the deeper issues driving his campaign: collapsing trust in government, the two-party trap, insider corruption, and the very real threat AI poses to millions of jobs. Andrew explains why he’s been sounding the alarm on automation for years and why he believes the country still has not caught up to what’s coming.

From there, we shift into Noble Mobile and the simple idea behind it: most Americans are getting crushed on wireless bills and barely question it. Andrew breaks down how Noble works, why phone service has become an overpriced commodity, and how reducing costs and screen time can both improve people’s lives.

This is a conversation about ambition, common sense, broken systems, and trying to build something better instead of just complaining about what’s broken.

Thank you to our sponsors

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

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

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

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

For more information about Noble Mobile, and to get started for just $10 your first month, head to https://noblemobile.com/rideout

Chapters

(00:00) Welcome and Book

(00:35) Why Run for President

(01:02) Meeting Presidents Up Close

(05:31) Fame and Being Recognized

(06:56) Growing Up With Racism

(08:47) Kids Today and Toughness

(11:58) Government Accountability Problem

(13:40) Congress Approval vs Reelection

(15:57) AI Automation and Freedom Dividend

(17:44) Two Party Trap and Independents

(21:55) Builders for Leadership Mark Cuban

(23:21) Noble Mobile Cuts Your Bill

(28:32) Phone Addiction and Family Rules

(33:00) Why Wireless Is a Commodity

(34:25) Tech Change Nostalgia

(35:55) Parents Immigration Story

(36:15) Immigrant Parents Leap

(37:12) American Dream Debate

(38:12) Indie Media Breakthrough

(39:03) Creator Economy Examples

(40:17) Work Guidance And Taxes

(42:30) How To Run For President

(44:22) Money Consultants And PACs

(46:18) Debate Stage Reality

(50:43) Union Power And Politics

(54:44) Noble Mobile Origin Story

(57:24) Cutting Bills And Compounding

(01:04:40) Parenting Screens And Safety

(01:09:33) Wrap Up Book And Subscribe
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This week I sat down with my editor Mishka for a raw conversation about the release of my memoir, Everything You Want Is on the Other Side of Hard.

I open up about the childhood abuse and chaos that shaped me, the years I lost to addiction, and the long road back through sobriety, endurance sports, and rebuilding my life. We talk about opioid addiction, withdrawals, Subutex dependence, and the moment Vivitrol finally helped me break the cycle.

We also dive into the deeper parts of my story — the mentors who changed my life, the pressure of success in finance, marriage and fatherhood, adopting my daughter from Ethiopia, and Shelby’s battle with breast cancer.

This episode isn’t a victory lap. It’s an honest look at trauma, fear, discipline, and the work it takes to keep moving forward.

Because the truth is simple: Everything You Want is on the Other Side of Hard.

Get the book here: https://www.theothersideofhard.com/

Thank you to our sponsors

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

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

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

Chapters

(00:00) Book Launch Jitters

(02:08) Family Fallout Update

(03:32) Brothers And Chaos

(07:29) Parenting And Ambition

(12:36) Angels And Fear Lessons

(15:08) College Fights And Coke

(19:11) Dream Dies New Direction

(21:48) NYC Hustle And Vertical Club

(26:41) Opioids And The Last Time Loop

(28:03) Withdrawal And Getting Sober

(35:59) London Glamour Mom Money

(36:56) Loans And Survival Mode

(37:35) Writing About Mom

(38:44) Toning Down The Book

(39:45) London Drugs And Leadership

(42:25) Porsche Paranoia

(43:11) Shelby Style Stories

(45:24) Tom Browne Fashion Era

(48:50) Friendship Across Differences

(50:07) Subutex Vicious Cycle

(53:33) Vivitrol Way Out

(55:23) Finance Crash And Bonuses

(59:43) Job Loss And Reinvention

(01:05:58) Adoption And Getting Clean

(01:08:52) Running Through Emotions

(01:11:36) Crisis Mode First Responder

(01:14:38) Bike Crash Aftermath

(01:15:51) Boxing As Life Metaphor

(01:20:19) Owning Failure And Quitting

(01:23:44) No Finish Line Mindset

(01:27:15) Shelby Cancer Update

(01:28:28) Win Or Die Trying

(01:33:00) Escape From New York

(01:35:44) Transracial Adoption Talk

(01:41:01) Community In Nashville

(01:46:08) Race Strategy Not Cheating

(01:50:24) Neve at Start Line

(01:53:52) Calf Injury Breakthrough

(01:56:59) Masters Title Surprise

(01:58:17) Onsite Therapy Reset

(02:01:59) Roommates and Brotherhood

(02:06:06) Rich Roll Connection

(02:10:30) Gobi Prep and Gear

(02:11:50) London Championship Twist

(02:19:57) Running Beyond Identity

(02:22:21) Life Lessons and Farewell
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In this bonus episode I sit down with Eli Wehbe for a raw conversation about status, addiction, reinvention, and the cost of living for validation.

Eli talks about growing up inp Moreno Valley, breaking into Hollywood nightlife, going from door guy to partner at Warwick, and building relationships with celebrities at the height of LA club culture. He also opens up about the partying, the public fallout that blew up his life, and the decision to disappear from social media and rebuild from scratch.

What started as a reset turned into a full obsession: marathons, trail racing, 100-milers, Moab 240, and now a real shot at podiuming Arizona Monster 300.

Ken and Eli get into sleep deprivation, fueling, sponsorships, social media, and the mindset it takes to compete in races most people can’t even imagine finishing.

This is a conversation about image versus reality, losing the identity you built, and finding something real on the other side of pain.

Thank you to our sponsors

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

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

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

Chapters

(00:00) Meet Eli

(01:24) From Moreno Valley to LA

(02:24) Breaking Into Nightlife

(03:19) Building a Celebrity Rolodex

(04:48) Playhouse and the Golden Era

(05:41) Mike Posner and Reinvention

(07:41) Coke and Party Culture

(10:36) Overdose Lawsuit Fallout

(12:20) Cancel Culture and Going Dark

(14:31) Running as a Reset

(17:04) GHB Explained and Narrative Spin

(20:36) Cops, Phone Search, and Lessons

(25:25) Case Outcome and Drug Dangers

(27:31) First Trail Run Disaster

(29:49) Water Bubbler Close Call

(31:15) Mountain Lion Encounter

(32:47) From 50K to 300 Miles

(35:57) Sleep Strategy Midrace

(38:11) Winning Mindset No Balance

(39:56) Injury DNF Redemption

(40:50) Stage Racing With Packs

(43:49) Podium Goals And Coaching

(45:12) Fueling Ketones Aid Stations

(48:34) Shoes Sponsors Speed Project

(51:49) Recovery Age And New Book

(53:43) Book Copy Surprise

(54:58) Online Persona vs Reality

(56:02) Relentless Outreach Mindset

(56:37) Andy Frisella Connection

(58:29) Cam Haynes and Goggins Reel

(01:02:59) Moab Finish Line Moment

(01:04:17) Validation and Winning Mindset

(01:08:31) Race Calendar and Leadville Plans

(01:10:00) Altitude Pain and 100 Mile Lessons

(01:13:48) Sponsors and Runner Branding

(01:16:31) Wrap Up and Where to Follow
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Daniel Dart is the founder of Time Again, but before music, before venture capital, before MIT, he was homeless, gang-affiliated, and sentenced to decades in prison on kidnapping and carjacking-related charges.

After fighting his case on appeal and earning a reduced sentence, Daniel rebuilt from nothing — working housekeeping jobs, getting sober, and deliberately surrounding himself with “winners.” That path led him into international development, work connected to the World Bank and the Bezos Family Foundation, two master’s degrees at the London School of Economics (without traditional prerequisites), and an MBA at MIT.

Today he runs Rock Yard Ventures, invests in critical and foundational industries, and is pursuing a California governor’s pardon.

This is a conversation about prison politics, systemic failure, stigma, merit, second chances, and what it actually takes to rebuild a life from the ground up.

Thank you to our sponsors

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

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

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

Chapters

(00:00) Meet Daniel Dart

(01:37) From Homelessness to Drive

(02:50) Family Chaos and Placements

(04:10) System Failures and Resentment

(05:52) Life on the Streets

(11:01) Gangs and Prison Reality

(14:18) Finding Music and Purpose

(17:45) Violence Risk and Prison Code

(24:23) Charges Plea and Appeals

(31:14) First Day Prison and Transfers

(33:10) White Gangs Breakdown

(33:20) Arizona Hunger Strike

(34:37) Shackled Prison Transport

(35:36) Cops as Gangs

(36:11) Fighting the Appeal

(39:51) Judge Offers Two Options

(42:48) Release and Low Yard Life

(47:29) Guard Stories and Violence

(52:49) Sponsor Break Athletic Nicotine

(53:44) Rebuilding After Prison

(56:33) From Music to Policy

(58:15) World Bank Mentors and LSE

(59:08) Bezos Foundation Break

(01:02:48) Two Masters at LSE

(01:03:37) Saudi Merit Over Stigma

(01:07:02) Stigma Hits Banking

(01:08:24) Banking Stigma Fallout

(01:09:33) From LSE to MIT MBA

(01:12:57) Allies Who Changed Everything

(01:15:02) Building Prison Reentry Program

(01:17:27) Launching Rock Yard Fund

(01:19:58) Imposter Syndrome to Conviction

(01:22:58) Fundraising and Lead Investor Mindset

(01:27:15) Missionary Founders and Long Game

(01:28:53) Fund Strategy and Sticky Industries

(01:38:04) Pardon Update and Final Wrap
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John “Johnny Bart” Bartolomeo served nearly 27 years of a 35-year federal sentence after tracking down and killing a rival gang member — a decision that would define the next 10,000 days of his life.

In this raw and unfiltered conversation, Johnny walks through his upbringing in East Boston, joining the Hells Angels, the violence that led to his arrest, and the reality of serving decades inside some of America’s toughest federal prisons. From Con Air transfers and Leavenworth politics to solitary confinement, COVID lockdowns, paranoia, marriage behind bars, and suicidal thoughts — he shares what it actually takes to survive that long.

But this isn’t just a prison story.

It’s about what happens when the rage burns out. When the ego collapses. When a man decides to change.

Today, Johnny works in recovery, advocates for second chances, and lives by a simple mantra that carried him through 10,000 days inside: “Just hold on for one more day.”

Subscribe / listen on all platforms: https://lnk.to/the-other-side-of-hard 

Thank you to our sponsors

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

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

Chapters

(00:00) Welcome and Redemption

(01:24) Surviving COVID Lockdown

(06:29) From East Boston to Hell's Angels

(10:22) How He Joined the Club

(15:54) The Killing and Manhunt

(22:43) Caught by the Feds

(25:39) The 35 Year Plea Deal

(31:51) No Bail and Pretrial Jail

(36:57) Sentencing Speech and Transfers

(41:39) Con Air to Leavenworth

(42:11) Shackles and Black Box

(43:09) Bathroom Break Reality

(44:10) Con Air Rules and Marshals

(45:07) Panic Attacks in Transit

(46:55) Oklahoma City Transfer Shock

(49:38) Leavenworth Boston Crew

(50:19) Prison Racial Politics

(55:08) Leavenworth Daily Tension

(56:21) Chow Hall Table Standoff

(01:03:23) From Leavenworth to Lows

(01:05:53) Cell Move Threat Backfires

(01:08:08) Beating the DHO Case

(01:10:06) Prison Love and Marriage

(01:14:36) Email Kiosks and Furlough Talk

(01:15:54) Inmate Van Walkout

(01:18:01) Rapport Over Rules

(01:18:31) Transfer Furlough Explained

(01:20:57) Wife Pickup And Freedom

(01:22:29) Paranoia And Prison Politics

(01:26:54) Hotel Visits And SHU

(01:30:23) First Step Act Breakthrough

(01:34:10) Drug Program And Staff Allies

(01:39:45) Release And Reentry Support

(01:42:04) 27 Straight Brand Origin

(01:43:25) Bean Shooter And Social Media

(01:45:07) Covering Club Tattoos

(01:46:05) Final Message
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