469. How to Turn Your Darkest Failures into Unstoppable Drive with Ken Rideout

What if the same thing that nearly destroyed you is the reason you become unstoppable?

In this episode of The Game Changing Attorney Podcast, Michael Mogill sits down with Ken Rideout, world champion marathoner, former Wall Street trader, and recovering addict whose life reads like a story most people wouldn't believe. From a rough, blue-collar upbringing in Massachusetts to winning an ultramarathon across the Gobi Desert, Ken's path has been anything but linear. This conversation digs into how grit actually gets built, why money never filled the void he expected it to, and what it takes to bet on yourself when everyone around you says you can't.

Here's what you'll learn:

Why toughness isn't something you're born with, and how you can teach it to yourself

Why money won't make you happier, even after going from broke to wealthy

What it takes to turn a failure into the fire that drives everything after

Ken built his comeback one decision at a time, and this episode shows you how to do the same.

(00:00:00) Introduction (00:02:19) Why Ken wrote the memoir (00:04:33) A rough upbringing (00:07:49) Is hustle born or built? (00:09:23) The road to Wall Street (00:14:47) Money, watches, and insecurity (00:16:10) How addiction took hold (00:17:24) The constant struggle to stay sober (00:19:37) Why high achievers are wired differently (00:22:03) Finding endurance sports (00:24:24) Quitting the Ironman World Championships (00:32:10) The race across the Gobi Desert (00:39:15) How he defines success now (00:47:33) What it means to be a game changer

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Links & Resources:

Ken Rideout

Everything You Want Is on the Other Side of Hard by Ken Rideout

David Goggins

Mitchell Hooper

Darren Waller

Mat Fraser

Into Thin Air by Jon Krakauer

Elon Musk

Jeff Bezos

Mark Zuckerberg

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Learn what sustainable growth can look like for your firm at crispcoach.com.

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Past guests on The Game Changing Attorney Podcast include David Goggins, John Morgan, Alex Hormozi, Randi McGinn, Kim Scott, Chris Voss, Kevin O’Leary, Laura Wasser, John Maxwell, Mark Lanier, Robert Greene, and many more.

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