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The Rich Roll Podcast

Ken Rideout On Why Everything You Want Is On The Other Side Of Hard

The Rich Roll Podcast

Rich Roll

Education, Society & Culture, Self-improvement, Health & Fitness

4.713.3K Ratings

🗓️ 9 March 2026

⏱️ 114 minutes

🧾️ Download transcript

Summary

Ken Rideout is a masters world champion marathon runner, recovering opioid addict, and the author of the new memoir, “Everything You Want Is on the Other Side of Hard.” This conversation explores the childhood trauma Ken spent decades outpacing, the addiction that nearly destroyed him, his wife Shelby's cancer battle, and the paradox that the very things that propelled him to extraordinary heights became Achilles heels. We discuss his relentless mindset, the role of pain and suffering in igniting willingness, and why the real obstacle was never the competition. Along the way, we arrive at a truth familiar to every addict: self-awareness will avail you nothing. It's what you do with it that matters. Ken is a real one. Enjoy! Show notes + MORE Watch on YouTube Newsletter Sign-Up Today's Sponsors: BetterHelp: Get 10% OFF the first month👉🏼https://www.betterhelp.com/richroll  Rivian: Electric vehicles that keep the world adventurous forever👉🏼https://www.rivian.com  WHOOP: The all-new WHOOP 5.0 is here! Get your first month FREE👉🏼https://www.join.whoop.com/Roll  Momentous: High-caliber human performance products for sleep, focus, longevity, and more. For listeners of the show, Momentous is offering up to 35% off your first order👉🏼https://www.livemomentous.com/richroll Check out all of the amazing discounts from our Sponsors👉🏼https://www.richroll.com/sponsors Find out more about Voicing Change Media at https://www.voicingchange.media and follow us @voicingchange

Transcript

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0:00.0

Extreme discipline has given me the life I wanted, but my kids are like my dad is crazy because I'm

0:06.6

constantly on them. Can't be easy to be your kid. No, it's not. And what they see is intensity and

0:13.0

aggressiveness. And I don't want to put this burden on them. We have Ken Rideout, one of the world's

0:19.4

preeminent Masters athletes.

0:21.4

A former prison guard Wall Street trader.

0:23.6

He has overcome addiction.

0:25.6

He's been put in that fight or flight situation, and he's always picked fight.

0:30.5

There's an element of me that's tortured, and my protective mechanism is to have a hard exterior.

0:37.9

All of the hard charging, driving, and trying to win and be the best is just an extension

0:42.9

of wanting validation.

0:45.1

There's something missing in my life that I have to do, which is...

0:49.9

Ken, right out, you made it here.

0:51.4

You're back in the studio.

0:52.8

Round three.

0:56.6

This is going to be a targeted conversation.

1:02.6

We're here to celebrate Ken's brand new book called The Other Side of Hard.

1:05.4

You did an incredible job on this book.

1:30.3

It's memoir, essentially, but it's also interlaced with all of these kind of, you know, like life learnings and wisdom about like how to approach obstacles and how to get unstuck and we're going to parse all of that. But before we even go into it, I want to kind of land on the obsession piece right now. Because so much of the book is about your obsession, your obsession with becoming someone in the world,

1:34.6

becoming this master's world champion, winning races.

1:38.3

Initially it was finance, you know, and this is a moving target for you,

1:43.8

but underneath it all,

1:46.1

there's always this, like, layer of obsession that's driving everything. So talk a little bit about,

...

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