Get A Shift On: Career Change and Business Stories

How Lifestyle Marketing and a Love of Adventure Shaped Oli Russell-Cowan’s Uncharted Career


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In this episode, I sit down with Oli Russell-Cowan, a global brand strategist, founder of Unchartered Territory, and someone I’ve known since our school days. We rewind the clock to our boarding school years and explore how Oli's love for skateboarding, surfing, and taking the unconventional route shaped his career.

Oli opens up about his journey from chasing waves to shaping culturally relevant brands, including time at Liquid Death and building global events platform Rad Season. He talks candidly about launching his own agency, the risks of entrepreneurship, and why understanding people matters more than any marketing funnel.

We dig into team dynamics, how to stay grounded in a world of AI and rapid change, and what it really takes to turn passion into a career without losing your grip on reality (or the market).

If you're navigating a career change, building something from scratch, or just wondering how to make a living doing what you love , you will enjoy this episode.


Follow Oli here:LinkedIn profile

Plus here is Unchartered Territory links:

Website

LinkedIn

Instagram

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⁠⁠David's LinkedIn⁠⁠

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Free Personal Exit Plan / Work With Me

Want to know if you are ready for a career change? Answer these 10 questions and find out!Chapters

00:00 Revisiting Old Friendships

02:25 Career Journey and Life Changes

04:56 The Birth of Rad Season

07:23 The Impact of Liquid Death

09:55 Embracing Rebellion in Marketing

12:21 Lessons from Liquid Death

14:41 Navigating Bad Days

17:03 The Importance of Team Dynamics

19:37 Starting Uncharted Territory

22:16 Lifestyle Marketing Explained

24:40 The Role of AI in Business

27:25 Future Plans for Uncharted Territory




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Get A Shift On: Career Change and Business StoriesBy David Birchmore