Jenna Lee Dillon spent her growing up years in Southwest Colorado - in the small town of Mancos - on the way from Durango to Mesa Verde National Park. Her father was in the real estate business - some construction but especially buy, fix, and flip - a decade before it was cool. After high school, she wanted someplace bigger and warmer, which landed her at Arizona State University.

Just out of school, Jenna Lee landed a job in marketing - a remote job for a California agency - and she soon evidenced her gutsy personality by starting her own freelance agency on the side, and exploring the most interesting places to live. With stops in Austin, Chicago, Portland, Dublin and Fort Collins before finding her current home in Arvada, Jenna Lee lived the digital nomad lifestyle a decade before it was cool! She’s a 6X Founder, and is turning one of her ventures - Screen Freed Revolution - into a non-profit in 2026.

In this conversation we explore financial best practices and emotions, the urge to start new things and to run Spartan Races, and discuss why Jenna Lee and her family should move back up to Fort Collins. There’s lots of smart business content, many fun and inspiring stories, and plenty of laughs, so please join me in enjoying my conversation with Jenna Lee Dillon.

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Music By: A Brother's Fountain