Heather Jackson: Gravel & Ultra Trail Running Pro - Positive Risks, Growth & the Power of Starting Something New

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Heather Jackson has won six full Ironman triathlons, 16 Ironman 70.3 races, the Escape from Alcatraz triathlon and she also won the Wildflower triathlon four times. She played D1 hockey at Princeton where she was a two-time captain and was on the US National team for cycling track racing. In 2023, she left triathlon to be a pro gravel racer AND a pro ultra trail runner. In her first season she won the Belgian Waffle Ride San Diego and the Javelina 100 foot race.

I mean, damn. 

Image credit: Howie Stern Photo

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Heather has an awesome YouTube channel and if you’re a fan, you know she has done a lot of media and podcast appearances. In this interview, we get into new material and talk about Heather’s mind game, why she continues to take positive risks and try new things and much more.

Find Heather on YouTube and Instagram @hjacksonracing, find those links below. A big thank you to Michael Marckx and Heather’s husband Wattie for helping make this interview happen and to Heather for everything she graciously shares in this conversation.


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We are in year six of Choose the Hard Way and it’s going to be a big one with some amazing guests and the chance for us to spend some time together as a community at a few gatherings and live events.

To make it all happen I’m open to mission-aligned sponsors I’d be proud to share with my audience directly supporting the show this season. If you or someone you know have a company that wants to reach the high-achieving, high-influence, highly networked people who listen to this show and do amazing things, then send a DM to @hardwaypod or email us at choosethehardway@gmail.com.

I’m also ready to retire the Giant TCX cyclocross bike I’ve been using to race gravel since 2015 and I’m ready for a new ride. If you’re in the industry and work for a company that makes an amazing bike you’d like me to race and talk about this year, holler at me and let’s make it happen.

Finally, I’m going to have big news to share some time in the next few episodes about the business I started that I’ve quietly been working on for the past 18 months. We are getting ready to publicly release our product and I want to give you all the opportunity to be among the first to get to try it.

Go to choosethehardway.com to sign up for the newsletter and if there’s someone you think would make a great guest, DM @hardwaypod.

Choose The Hard Way is a Big Truck Production. Anthony Palmer at Palm Tree Pod Co is the producer and editor and Emily Miles is head of digital and marketing. Jeffrey Nebolini is the world-renowned designer behind our brand identity and the Choose the Hard Way logo. The content for this show is created by @vontz.

Heather Jackson Website | Instagram | YouTube

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