Podcast Summary: The Herd with Colin Cowherd (3 & Out)

Episode Title: Ken Rideout's Story, Will Lamar Crash Out, Could McDonald Call Offensive Plays
Date: February 11, 2026
Host: John Middlekauff (on Colin Cowherd's network)
Guest: Ken Rideout (elite age-group marathoner, former finance exec, recovering addict)

Episode Overview

This episode of 3 & Out—hosted by John Middlekauff, featured on The Herd with Colin Cowherd—presents a wide-ranging and deeply personal interview with Ken Rideout, an ultra marathon champion, former finance professional, and recovering addict. Ken shares his remarkable life journey: from a tough upbringing in blue-collar Boston, to a high-powered (and drug-fueled) finance career, through addiction and recovery, and ultimately to world-class success in endurance running.
Following the interview, John answers listener mailbag questions on NFL topics including the futures of Lamar Jackson and Jalen Hurts, NFL coaching hierarchies, and more.

Interview with Ken Rideout (00:05–45:23)

Ken Rideout: From Hardscrabble Boston to Marathon Champion

Early Life & Boston Roots

• Tough Environment:
  Grew up in Somerville, MA ("very much a blue collar, like, hardscrabble town" [04:14]). Family members cycled in and out of prison.

• First Job:
  Began as a prison guard right after high school—the same facility where family members had served time.

  "When I got out of high school, my first job was as a guard in prison outside of Boston. My stepfather had already been an inmate there, and my younger brother would eventually be a prisoner there multiple times." [04:15]

• Sports Foundation:
  Played ice hockey and football in college, boxed at the New York Athletic Club.

Breaking Into Finance

• Striking Luck, Living Fast:
  Landed a junior finance role after impressing a commodity trader at a gym, despite a "hazing" culture similar to sports locker rooms.

  • Fights back against hazing (literally), is fired, but quickly lands a higher-paying job after news spreads of his tough-guy reputation.

    "[On hazing] One day I just had had enough of it and I slapped a guy across his face...When some of the senior traders at Enron heard that story, they called me up...By Monday I had a job making twice what I was making" [05:14]

• Success & Downfall:
  Rapid promotion, big money, eventual move to London—while his opioid addiction deepened after surgery ("for the next 10 years I was basically high on opioids 24/7" [05:53]).

The Drug Culture on Wall Street (17:25–19:30)

• Hidden Addiction:
  Ken hid his addiction from almost everyone, maintaining a high level of performance and fitness externally.
  • Retail finance depicted in Wolf of Wall Street is accurate, but as an institutional trader, he says “everyone was an absolute maniac, especially in London.”
    • "I never told anyone I was doing drugs, so in my mind, people probably just thought that I was a little crazy and aggressive. But...I was just happy as can be." [17:30]
  • Describes chaos, drug use, and lack of inhibition among colleagues.
    • "There were people going to the bathroom, come out, cocaine all over their nose..." [17:30]

Hitting Rock Bottom & Recovery (23:23–28:11)

• Turning Point:
  Marriage and adoption plans force a crisis; Ken attempts outpatient detox, experiences severe withdrawal while hiding it from his wife.

  • "I woke up to go to the bathroom one night, blacked out in the bathroom, fell down, smashed my head, woke up. My wife is like, what the f. What is going on?...I'm either gonna tell her the truth or jump off that balcony." [25:00]
  • He chooses honesty—calls himself "a junkie" for the first time, with his wife responding supportively.

• Path to Running:
  Began daily 10-mile runs—part penance, part withdrawal management. Running becomes a driver for his sobriety.

  "That's when I started this tradition of running 10 miles every day. It was part penance...in part, I want to expedite this process of getting the drugs out of my system." [28:16]

Running & Redemption: From Ironmans to Ultramarathons (29:40–41:43)

• Athletic Ascent:
  Starts with triathlons (three Ironman Hawaii finishes), transitions to competitive marathoning and ultra events.

  • Quickly excelled after moving to LA and training in the mountains (often alongside Reggie Miller, who became a friend and supporter; [09:23–09:54]).
  • At 50, wins Myrtle Beach Marathon, then four of the six World Marathon Majors (Boston, New York, Chicago, Tokyo).

    "The day before I turned 50, I won the Myrtle Beach Marathon...In 23 was the world championships for age group. So I beat everyone in the world over 50." [08:57]

• The Gobi March—Mongolia Ultra:
  Last-minute entry; Ken carries all supplies, confronts near disaster (broken pack, exhaustion, first-aid drama), but rallies to a decisive victory—his first-ever ultra event.

  "That race has been called the toughest race in the world...the equivalent of a marathon every day for five days with a 50 miler mixed in." [38:43]

Running Routine & Mindset (32:49–35:09)

• Consistent Discipline:

  • Runs 10 miles every day without exception, regardless of location or weather.

    "Every single run I've done since 2013 is there...I've averaged, like 4,000 miles a year for the past five years, which is 10.6 miles a day every single day." [32:54]

  • Extreme conditions (snowstorms, heat, traveling): "Every day. Tornado, hurricane, snowstorm. Every single day." [33:23]

  • Prefers cold over heat for running: "The heat is miles harder than the cold within reason..." [34:33]

• Community:
  Now well-known in his Nashville neighborhood, coaching and inspiring young athletes.

  "Now...every morning when I run, it's literally like I feel like the local celebrity. Every single car, as they're driving the kids to school...Coach Ken, Coach Ken. It's the happiest time of my life now." [42:47–43:22]

Lessons, Mindset, and Message

• Facing Fears:
  Ken emphasizes everyone feels fear, citing his own experiences in boxing, running, and life.

  "If I've done anything well, it's learned to do things scared." [11:09–11:36]

• Resilience & Grit:
  "I've got no special skill sets. I have no natural talent. But I do have incredible willpower and grit, and that's really all you need." [42:12]

• Book Promo:
  The Other Side of Hard (available March 10th), for anyone considering life changes, sobriety, or simply seeking a path to self-improvement.

Notable Quotes & Moments

• On Boston's Toughness:
  "You just learn to get a thick skin quick because if you don't, you won't survive." [12:11]

• On Finance Culture:
  "You get the guys that are like overweight doing coke and then you get the like hardcore like fitness finance bros" [18:43]

• On Recovery’s Turning Point:
  "I'm either gonna tell her the truth or jump off that balcony. And I just, I just, like, came clean with everything. I'm like, I'm a junkie. I'm whacked out. I'm in withdrawals, and it was horrible." [25:00]

• On Discipline:
  "I've run everywhere in the world...run in some cold places...well below zero. Just have gear." [33:09–34:18]

• On Inspiration:
  "If you put the addiction to the right place, you really can get going in the right direction, whether that's working out or...healthy lifestyle." [41:43]

Mailbag & NFL Discussion (46:24–71:19)

Highlights by Topic

The 2008 Steelers Defense

• Underrated historically; compared to 2000s Ravens and Legion of Boom. Names roster, notes general excellence and intensity. [46:24]

Inside Football Operations

• Describes “Big Dom” (Eagles) and informal staff roles ("Elite information accumulator"; similar to Ernie Adams for Belichick—doesn’t fit typical role definitions).
• NFL staff structures involve many assistants, not all performing critical tasks, some duplicative ("How are we not better in those units?" [70:27]).

Lamar Jackson's Future

• Fan question discusses whether Lamar Jackson will decline like Russell Wilson.

• John argues Lamar is a superior passer and playmaker, but sustained success depends on maintaining health and adapting play style for fewer hits as he ages.

  "I think Lamar, I think these next couple years are pretty critical. Like, he's not going to be running around at 36 like he's able to do now in theory." [49:08]

Jalen Hurts vs. Sam Darnold

• Debates Hurts’ status: if he’s unwilling to run, offensive performance drops ("if Jalen does not want to run anymore, I'm out on him as a player" [60:22]).

• Darnold is now viewed as a "solid player"; Jalen labeled a "game manager" if he does not regain his dual-threat abilities.

Could Mike Macdonald Call Offensive Plays?

• Listener asks if defensive-minded coach Mike Macdonald (current Ravens DC) could call offense in the NFL.
• John flatly dismisses the possibility (too much to handle, expertise is highly specialized on each side).

High School vs. NFL-Coached 8th Graders

• Hypothetical: Would NFL coaching staff + 8th graders beat high school varsity?
  • John says size and maturity gap is too large—even brilliant scheming can’t overcome physical development in football.

Miscellaneous NFL Talk

• Rams' Puka Nacua, Stefanski’s offensive struggles, Super Bowl-winning coaches ranked by quality, Eagles vs. Seahawks matchup, importance of coaching infrastructure, and more.

Timestamps for Key Segments

• Ken Rideout Interview Begins: 03:08
• Childhood & Boston: 04:13–13:13
• Prison guard stories: 13:13–14:33
• Boston mob culture/violence: 14:33–16:40
• Addiction & Finance: 17:25–23:29
• Rock Bottom & Recovery: 23:23–28:11
• Running/Marathons: 28:11–35:09
• Gobi Desert Ultra: 35:09–41:43
• Life lessons, book pitch: 41:43–43:22
• Community/Coaching: 42:47–43:22
• Mailbag (NFL topics) begins: 46:24
• 2008 Steelers defense: 46:24
• NFL staffing & “Big Dom”: 47:54
• Lamar Jackson future: 49:08
• Mike Macdonald play calling: 56:48
• Jalen Hurts / Darnold debate: 58:36
• Other NFL mailbag: 64:00–71:19

Memorable Moments & Quotes

• On fear and toughness: "Everyone's scared, dude. You just have to learn how to do this shit while you're scared." [11:09]
• On honesty and recovery: "I'm looking at her and I'm looking at the balcony, and I'm like, I'm either gonna tell her the truth or jump off that balcony." [25:00]
• On running discipline: "Every day. Tornado, hurricane, snowstorm. Every single day." [33:23]
• On turning addiction into achievement: "If you put the addiction to the right place, you really can get going in the right direction." [41:43]
• On opportunity in America: "We live in the greatest country on Earth. You can do anything you want here." [42:12]

Episode Tone & Takeaways

The conversation is raw, authentic, and motivational. Ken Rideout doesn’t shy away from sharing his darkest moments—delivering his story with biting, unvarnished honesty and blue-collar humor. John Middlekauff is candid, sympathetic, and pragmatic, guiding the conversation to highlight universal lessons on resilience, personal growth, and the power of relentless daily discipline.

The mailbag delivers John’s signature NFL analysis: opinionated, thorough, with plenty of inside perspective from his days working in the league.

Essential Message:
Anyone can radically change their life through grit, candor, and relentless effort—Ken’s story proves that overcoming even decade-long struggles with addiction is possible, and that daily discipline (whether in running, work, or recovery) can open up opportunities you never imagined.