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Episode · Dec 3, 2025 · 1 hr 48 min

Pills, Pain & Fatherhood

with Ken Rideout

Ken Rideout is a former pharmaceutical sales rep and Wall Street trader who discusses his ongoing recovery from opioid addiction and the role of endurance sports in his life.

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“The only thing that can give you peace is your own mind.”
Ken Rideout

Summary

Ken begins with the Gobi March, a self-supported six-day race across 155 miles of Mongolia that he entered with four weeks to prepare. He had never run with a pack or camped, started too fast, and lost ground to experienced racers. After repairing a broken pack and adjusting his pace, he caught up, helped a rival through the desert and won the final stage. The race gives them a way to discuss competition, recovery and why he keeps choosing difficult goals.

He then traces his addiction from Somerville through pharmaceutical sales and Wall Street, where income and status did not stop him from using opioids. He says he moved to London hoping to outrun addiction, but the drugs followed him. His adopted daughter from Ethiopia became a turning point: he wanted to be sober for his family, went through outpatient detox and began using running as both punishment and structure. With Mishka Shubaly, he talks about raising four children with Shelby, learning from endurance sports, and finding that lasting peace comes from his own mind, not money or race results.

Show notes

This time I’m the guest. My friend, co-conspirator, and writer Mishka Shubaly turns the mic on me.

We go deep into my past—from the years I spent hiding an opioid addiction and living a double life in pharmaceutical sales and later on Wall Street, to the moment I finally chose my family over my vices.

Mishka traces the full arc of my story: the lies I told myself, the fear of getting comfortable, and the role endurance sports played in rebuilding my identity through hard work. We talk about honesty, identity, and how running became the tool I used to leave my old self behind.

This episode is a raw, honest look at addiction, accountability, endurance, and the ongoing work of becoming the person you’re trying to be.

Ken Rideout Website: theothersideofhard.com YouTube: @ken_rideout Instagram: @ken_rideout X: x.com/KenRideout_

Read the transcript

Transcript

Made from YouTube's automatic captions and lightly corrected, so a few words and names may be off. Click a time to play the video from there.

Mishka Shubaly

You ready, bro?

Ken Rideout

I'm ready.

Mishka Shubaly

Dude, it's so funny hanging [clears throat] out with you in person because we've been talking like three times a week for the last year and I feel like like I'm meeting the Easter Bunny. It's you're actually a real guy. the um it it you know there's so and there's so many good interesting ways into your story, but I feel and I do want to get to your sort of origin myth, but I feel like the best place to kick it off. The one story that sort of encapsulates all the crazy unbelievable things about you is the Gobi March.

I mean, that sounds like it was just a crucible of suffering where it tested you at every turn.

Ken Rideout

Yeah, I feel like the Gobi Desert, the Gobi March in the Gobi Desert in Mongolia was like a [gasps] I don't know if a culmination of my life is the right description, but it's definitely reflects on all areas of my life from like being beaten down, feeling disheartened, feeling top of the world, and everything in between. But, uh, even from the moment I signed up for that race, I was like in a moment of, I don't know, bravado.

I was like, "Dude, I'll kill everyone at that race." And I and I reached out to the race director. I had talked to a friend of mine called Scott Daroo who was the um CEO at Equinox and he told me he was doing this race and I don't even know why. It just I just blurted out like, "Dude, I'll kill everybody at that race." You know, it's kind of like [ __ ] talking, but at the same time, I was like, I bet I could win that.

I don't know why. I didn't know anything about it. You know, I had never run with a backpack. I had never gone camping. I'm I mean, you know me, I'm like I am not a camping guy. I am a big [ __ ] in a lot of ways. Uh but I grew up roughing it. I don't want to rough it anymore. I want to stay at the Four Seasons. I don't want to be sleeping in a tent. But if you tell me that there's a trophy for the person at the end who can suffer the most, I'll sleep on a bed of [ __ ] nails.

And when he told me I could do the when when when I told him that, he said, "Go ahead and try and get in. It's in 4 weeks." And um I reached out to the race director and they were like, "Yeah, happy to have you."

Key takeaways

  • A race result fades quickly, but preparation and difficult work can give structure to daily life.
  • Changing a destructive pattern may mean changing the behavior underneath it instead of trying to escape to a new place.
  • A parent can support each child's interests without asking that child to repeat the parent's life.
  • Honesty about addiction and setbacks can make recovery stories more useful to other people.
  • Money can widen your choices without giving you peace or changing who you are.
  • In an endurance race, helping a competitor can matter more than protecting a lead.

Nowhere to Hide

A weekly letter from Ken Rideout about doing the uncomfortable part, and the reasons we use to avoid it.

It starts with 3 Days, 3 Hard Things: one short story from Ken and one hard thing to do, every day for three days. Then one letter a week.