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RIDEOUT: The Other Side of Hard

RIDEOUT: The Other Side of Hard

By: Ken Rideout
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 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.© 2025 Ken Rideout Personal Development Personal Success Social Sciences
Episodes
  • From Prison Yard to Venture Fund | Daniel Dart

    From Prison Yard to Venture Fund | Daniel Dart
    Mar 4 2026
    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 Learn more about your ad choices. Visit megaphone.fm/adchoices
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    1 hr and 40 mins
  • From 35 Years to Freedom | Johnny Bartolomeo

    From 35 Years to Freedom | Johnny Bartolomeo
    Feb 27 2026
    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 Learn more about your ad choices. Visit megaphone.fm/adchoices
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    1 hr and 51 mins
  • Dirty Feet and a Battered Back | Nick Bare

    Dirty Feet and a Battered Back | Nick Bare
    Feb 25 2026
    Nick Bare has built his life in public. He announces the goal before he’s ready. He signs up for the race that might break him. He puts the business on the line and accepts the pressure that comes with it. This episode isn’t about highlight reels. It’s about what happens when discipline meets doubt. Nick talks about building BPN from a college apartment while serving as an Army infantry officer, surviving Ranger School, nearly running out of cash in the early years, stepping down as CEO from burnout, and eventually coming back to lead with more clarity and humility. We get into Leadville breaking him, the marathon that felt effortless, and why he believes most people sabotage themselves by “majoring in the minors.” But the real shift came when achievement stopped delivering peace — and faith reframed how he sees success, marriage, fatherhood, and leadership. At its core, this conversation is about overcoming ego, pressure, and the constant pull of “what’s next.” It’s about becoming the kind of person who doesn’t negotiate when things get hard. 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” Athletic Brewing: https://athleticbrewing.com Code "RIDEOUT" Rho Nutrition: https://rhonutrition.com Code "RIDEOUT" Chapters (00:00) Hybrid Athlete Praise (00:58) Curiosity Driven Training (02:33) Accountability Pressure (04:49) Discipline Over Motivation (09:34) Responsibilities Over Routine (12:20) BPN Origins and Drive (13:18) Childhood and Work Ethic (15:47) Anorexia and Recovery (20:36) College Hustle Supplements (23:53) Army Service and YouTube (26:23) Bootstrapping and Passion (31:33) Ranger School Reality (34:50) South Korea Business Scale (39:50) Cashflow and Creativity (43:40) Customer Impact and Mission (46:00) Hometown Mockery Story (47:26) Doubt and Mission (48:58) Mindset Before the Race (52:33) Ego Anxiety and Control (58:06) Major in the Majors (01:01:28) Obsessing Over Prep (01:05:32) Hardest Challenges Ranked (01:08:43) Marathon Magic Moments (01:11:50) Faith Transformation Story (01:22:35) BPN CEO Lessons (01:30:30) BPN Starter Supplements (01:33:43) Wrap Up and Subscribe Learn more about your ad choices. Visit megaphone.fm/adchoices
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    1 hr and 35 mins
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