What You Can Learn From the Biggest Failure in Endurance Sports, with Epic Bill Bradley

Outside Podcast

Wilderness, Sports

4.3 • 2.2K Ratings

🗓️ 18 February 2026

⏱️ 47 minutes

🔗️ Recording | iTunes | RSS

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Summary

In the 1980s and 90s, Bill Bradley was a video rental mogul. At his peak, he had stores all over Santa Rosa, California, was worth millions of dollars, and was seen as an industry innovator. That's probably why he was dismissive when a little company called Netflix appeared and proceeded to lay waste to the entire video rental industry. In a whiplash-inducing turn of events, Bill lost everything—his riches, his business, his marriage, and his sense of purpose. Prior to this life explosion, Bill was a casual runner, plodding along in a few marathons and Ironmans. And when he was at his lowest, he dove head first into the world of ultra endurance sports. Since the collapse of his VHS empire in 2005, Bill has taken on the world’s toughest challenges, like the Arrowhead Ultra, the Badwater Ultra, swimming the English channel, and attempts at the world’s tallest peaks. And yes, he has set records along the way. But what is truly remarkable and what turned Bill into Epic Bill, is that he has come short far more often than he has crossed the finish line. Epic Bill believes that his failures have taught him more than any victory ever could. Because how you try at one thing is how you try at everything.

Transcript

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0:00.0	This episode of The Outside Podcast is brought to you by Rolex.
0:05.0	It's easy to feel overwhelmed by climate headlines.
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1:16.0	This is the outside podcast with Paddyo.
1:25.3	I always liked running. I started doing triathlons and marathons, but I never did a 50-mile or anything.
1:33.3	I remember I brought it up to my second wife that I was going to do a 50-mile and she says,
1:36.3	you get so depressed after you don't make an Iron Man or this or that, you shouldn't do a 50-miler.
1:43.3	And then when I went bankrupt, she kind of left.
1:45.6	So, but I was walking around downtown San Francisco and I couldn't even look. I had no confidence left, but I could only look down at the ground. That's all I was doing. God, I remember how good I felt when I finished my first Iron Man, you know? I go, I need that feeling again. again. And then my buddy said that he tells me about this 50-mile, he goes, I know you've been talking about it's tomorrow, right? That's not much notice. But on top of that, I have poison oak on my manly parts.
2:10.7	What? Yeah, like, you know, from going the bathroom in the woods. And so I go, I got poison oak on my manly part. It's probably not a good idea. And Bill, let me guess. You did it anyways. Well, okay, let me keep going. Okay. So I'm going to bed thinking I'm not going to do it. I wake up at three in the morning, like Tom Cruise in risky business. I say, sometimes you need to say, what the bleep.
2:36.0	And I went down there and I ran that 50 miles like my life depended on it.
	...

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