Hear stories of balloon jumps, zoo dives, flipping out of planes & the personal growth and life lessons behind it all. In the final part of the conversation, Taylor Wallace shares how a spontaneous first jump in Brazil led to a passion for skydiving that has taken her across the world, from beach jumps outside Rio to balloon jumps over Cappadocia and massive skydiving festivals in the United States. She explains the discipline, humility, and constant learning required to stay safe in a high-risk sport, and reflects on how skydiving mirrors entrepreneurship and travel—requiring courage, adaptability, and trust in yourself when things don’t go as planned. The episode closes with Taylor reflecting on how global travel and adventure have shaped her resilience, perspective, and desire to keep pushing beyond her comfort zone.
Episode #377: Skydiving Around the World: Taylor Wallace on Risk, Fear & Finding Freedom in the Sky
Episode Summary
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About the Guest

Taylor Wallace
Taylor Wallace is a longtime digital nomad, remote entrepreneur, non-profit leader and skydiver who has traveled to over 80 countries. Over the last decade, Taylor has lived and worked across North America, Latin America, and Southeast Asia while leading strategic partnerships in venture capital, emerging tech, and social innovation. She advocates for “The Fit Founder” lifestyle, blending entrepreneurship with intentional living, and her work has been featured in Entrepreneur Magazine.
What You'll Learn
- How facing fear through experiences like skydiving can build confidence, humility, and sharper decision-making under pressure.
- What it takes to safely progress in a high-risk sport—and how discipline and preparation translate directly to life and business.
- How pushing beyond your comfort zone through travel and adventure can accelerate personal growth and reshape how you handle uncertainty.
Links From the Episode
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CONTACT AND FOLLOW TAYLOR
#1 BOOK THAT TAYLOR RECOMMENDS
#1 PERSON WITH WHOM TAYLOR WANTS TO HAVE DINNER
TOP 3 TRAVEL DESTINATIONS
TOP 3 BUCKET LIST DESTINATIONS
BUCKET LIST SKYDIVING PLACE
- Palm Jumeirah (Dubai)
SKYDIVNING CENTER MENTIONED IN THIS EPISODE
SKYDIVING EVENT MENTIONED IN THIS EPISODE
OTHER PLACES MENTIONED IN THIS EPISODE
Time Stamped Show Notes
**Click the time stamp to jump directly to that point in the episode.
[1:56] Taylor’s First Time Skydiving
[11:00] Skydiving Training, Licensure and Progression
[17:08] Skydiving Safety
[27:51] Skydiving from WW2 Era Planes in Baja Brazil
[28:58] First Hot Air Balloon Jump in Cappadocia, Turkey
[32:52] Doing Flips out of the Plane
[34:27] First Costume “Zoo Dive” in Chicago
[36:59] What travel means to Taylor
[40:50] The Lightning Round
[46:45] Follow and Connect with Taylor