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The Freetrail Podcast with Dylan Bowman

Brett Jackson | Struggling Well in Business, Sport & Life

The Freetrail Podcast with Dylan Bowman

Dylan Bowman

Running, Sports

4.8866 Ratings

🗓️ 8 May 2020

⏱️ 68 minutes

🧾️ Download transcript

Summary

Brett Jackson in a co-founder and managing partner at V1VC in Boulder, CO. Brett and I grew up together and have been close friends for many years. Though our personal pursuits are very different in appearance, they're very similar in practice. In this conversation we discuss the parallels between sport and business and how we can better struggle towards our goals. 
 
Topics of conversation: Brett's non-traditional career path, navigating highs and lows of sport/business, imposter syndrome, depression, self doubt, big wins and much more.
 
Follow Brett on Twitter
 
Reboot -- Jerry Colonna 
 
Dylan on the Reboot Podcast

Transcript

Click on a timestamp to play from that location

0:00.0

Hello, everyone and welcome back. It is an honor to have you here for what is, I think, up to this point, my favorite

0:23.0

episode of the podcast. It could be that I just have a lot of personal affection for this guy,

0:29.0

or it could be that we had a really great conversation. I will let you all be the judge of that.

0:36.3

But one major bonus is that there is zero corona

0:39.3

related conversation in this entire episode. The reason for that is because we recorded this back

0:45.6

in September of last year, well before any of us knew what a coronavirus was. We held off on

0:53.2

publishing for reasons that are unimportant, but I'm really glad

0:56.6

to bring it to you now as a reprieve from our current reality. But my guest today is one of my

1:03.3

best buds from childhood, an individual by the name of Brett Jackson. Brett is now a venture capitalist

1:09.8

based out of Boulder, Colorado,

1:12.6

but he's just been an immensely talented and successful businessman.

1:17.6

Going back to when we were in high school,

1:19.6

and he was involved with a footwear company that many of you will be familiar with,

1:24.6

called Crocs.

1:26.6

And Brett's career path has been totally non-traditional,

1:31.4

going back to when he dropped out of college, and has been carving his own path in a really

1:38.7

unique way and in a way that I think is different from a lot of people who have found themselves in a similar

1:47.2

career and a similar stature in their industry.

1:50.6

And it's always been something that I've really admired about him.

1:53.9

And I've always felt that we've been kindred spirits, not only in our friendship as kids,

1:59.4

but as we've grown into adulthood and pursued our own

2:04.1

different paths in very different fields, but with a lot of similar demands and a lot of similar

...

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