Jason Caldwell On Rowing Oceans, High-Performance Team Building, Experiential Leadership & Chasing The Impossible

Nov 15, 2021

Jason Caldwell, an extraordinary adventure athlete with 11 world records, discusses resilience and teamwork in high-stakes environments. He shares gripping stories from his ocean rowing adventures, emphasizing how confronting challenges fosters growth. Caldwell explores the delicate balance between leadership and vulnerability in team dynamics. He reflects on the importance of embracing failure, the strategies for coping with seasickness, and personal transformations that come through collaborative efforts. The conversation inspires listeners to chase audacious goals and cultivate deep connections.

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ADVICE

Act Now

View life as finite and fleeting to spur immediate action.
Prioritize how you spend your time, as weeks turn into years quickly.

INSIGHT

Interdependence in Rowing

Rowing requires interdependence, with no single star player.
Individualism is sacrificed for collective success in rowing.

ANECDOTE

First Atlantic Row Challenges

During Jason Caldwell's first Atlantic row, one teammate, Nick, became severely seasick.
Another teammate, Greg, chose to leave during Nick's evacuation despite being healthy, highlighting the mental challenge.

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Adventure begins when things start to go wrong. So stop looking for the shortcut. Embrace the difficult journey ahead.

Few embody this ethos better than today’s guest Jason Caldwell.

An extraordinary adventure athlete and beautiful beast of a human, Jason holds 11 world records set across 5 continents and 3 oceans, including a 320-mile unassisted traverse of the Namib desert (the longest desert trek across Namibia), captaining the fastest team to row across the Atlantic Ocean unsupported, and most recently, victory in the Great Pacific Race as captain of the fastest team to ever row from San Francisco to Hawaii, a feat Jason and his 3 teammates accomplished in just 30 days 7 hours, smashing the previous world record by an astonishing 9 days.

In addition, Jason is the CEO of Latitude 35, an experiential leadership and high-performance team building consulting company. He’s a widely sought-after public speaker on the Fortune 500 circuit and has taught at some of the country’s leading business schools, including Wharton, Columbia, Berkeley & West Point.

This is a conversation about what is required to tackle and accomplish audacious goals.

It’s about cultivating resilience, perseverance, and risk-taking. It’s about honing the willingness to fail, leveraging drive, and celebrating humility.

It’s also about ‘healthy quits’—the importance of knowing how, when and why sometimes it’s crucial to just call it a day.

But more than anything, this conversation is about the critical nature of team building. It’s about leadership through experience. Why success is never a solo affair. And how to get the best out those in your orbit.

If you’re into wild stories of adventure this one’s for you. But you don’t have to be the slightest bit athletic to gain significant value out of what Jason shares today.

To read more click here. You can also watch listen to our exchange on YouTube.

My hope is that this conversation inspires you to reevaluate your limits, find power in your community and invest more in adventure.

Needless to say, Jason has lived a wild life. This conversation nearly passed 2.5 hours—and I feel like we only scratched the surface.

Peace + Plants,

Rich