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The Freetrail Podcast with Dylan Bowman

Jerry Colonna | The Crucible of Leadership

The Freetrail Podcast with Dylan Bowman

Dylan Bowman

Ultrarunning, Training, Wellness, Endurance, Health, Running, Commentary, Trailrunning, Sports, Run

5773 Ratings

🗓️ 10 February 2021

⏱️ 62 minutes

🧾️ Download transcript

Summary

Jerry Colonna is the co-founder and CEO of Reboot, an executive coaching and leadership development firm based in Boulder, CO. Jerry is also the author of Reboot: Leadership and the Art of Growing Up. Jerry's style is a mix between therapist and consultant, helping his clients to gain a better understanding of themselves through what he calls radical self-inquiry. Jerry and I became acquainted during the lowest moment of my life and his work has had a tremendous impact on my professional and athletic career. His message has as much relevance to athletes as it does to entrepreneurs and founders. This was a special one.
 
 
 
 
 
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Transcript

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0:00.0

Hey, everybody. How is it going? I hope you're doing awesome. Welcome to Pillars. Of course, I'm Dylan Bowman. And this week,

0:23.0

it is my honor and privilege to welcome Jerry Colonna to the podcast. And while he might be an

0:29.9

unfamiliar name to some of you, maybe most of you, Jerry is a big deal. He is one of the most sought-after voices in the world of executive

0:41.0

coaching and leadership development. He is the co-founder and CEO of Reboot, which is his coaching

0:49.0

firm based in Boulder, Colorado, but with presence in New York City and San Francisco as well.

0:55.3

And he is also the author of a book called Reboot, Leadership and the Art of Growing Up that

1:01.7

we talk about a lot in this podcast. And if you're an avid podcast listener, you might remember

1:07.3

Jerry as the coach to the founders of Gimlet Media, the podcasting empire that

1:13.9

sold to Spotify just a couple of years ago. But while his practice is focused mostly on

1:21.2

entrepreneurs and executives, I think you'll find that Jerry's approach and his message is just as relevant to us athletes.

1:31.7

And since we didn't have enough time to really go into how Jerry and I became acquainted

1:37.5

during our conversation just because we had limited time,

1:40.9

I wanted to provide a little background on how Jerry's work had a huge impact on

1:46.7

me personally, professionally and athletically. I generally don't like podcasts with long introductions,

1:53.3

but I think it's important for context in this episode to provide that here on the front end.

1:59.5

And as I've spoken about many times in this podcast and

2:04.0

other places, 2019 was a terrible year for me. And when I was in the middle of my depression and

2:12.2

injury spiral in the summer of that year, my good friend and a former guest of this podcast, Brett Jackson,

2:19.7

came to Aspen on a little business trip where I was living at the time.

2:24.1

And after he was done with his meetings before he went back down to the front range,

2:28.9

we went for a little hike together one afternoon, and we had a really great deep discussion about life and struggle

2:37.6

and the painful moment that I was navigating at the time.

...

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