Miles Spencer is a seasoned entrepreneur, venture capitalist, and adventurer who has spent over three decades mentoring tech founders and building companies that have generated more than 1,100 jobs.
Miles Spencer
Entrepreneur, Investor, Storyteller, and Adventurer
Miles Spencer is a seasoned entrepreneur, venture capitalist, and adventurer who has spent over three decades mentoring tech founders and building companies that have generated more than 1,100 jobs.
With three successful digital media exits under his belt, Miles is also the author of the Amazon bestseller A Line in the Sand, inspired by his 1,100-mile expedition through the deserts of the Middle East.
His unique journey blends business strategy, exploration, and storytelling, offering valuable insights into leadership, resilience, and the power of curiosity.
About this Episode
In this episode, Miles Spencer shares the remarkable experiences that have shaped his life—from building startups and investing in game-changing ideas to trekking across vast deserts in search of deeper meaning. He talks about his early beginnings in Pennsylvania and how his family legacy and deep-rooted curiosity led him to both entrepreneurial and exploratory adventures.
Miles discusses what he’s learned from mentoring startup founders, the importance of solving everyday problems, and how failures taught him more than successes ever could. He also reveals the preparation and mindset needed to take on extreme adventures like scuba diving in the Galapagos and retracing T.E. Lawrence’s historic path across the Middle East.
We dive into the creation of A Line in the Sand, the cultural and historical discoveries along the way, and the lessons that travel and curiosity can teach us about humanity. From exploring global perspectives to understanding shared values across religions and borders, Miles encourages us to remain curious, plan thoughtfully, and always be open to learning from the world around us.
Listeners will walk away inspired by his journey, reminded of the beauty of diverse cultures, and energized to chase their own Green Pill moments.
“My experience in mentoring entrepreneurs is very much like mentoring children — it’s always more powerful to have someone learn the lesson for themselves.”
Miles Spencer
” Not every startup is successful. You can do your best, but entrepreneurship is a risky game of odds — the universe decides which ones win.”
Miles Spencer
Show highlights

“The first thing I look for is an ordinary problem that everyday people are experiencing over and over again across the globe.”
Miles Spencer
“The depth and breadth of our ignorance about other religions and cultures was preventing us from understanding how much commonality we had.”
Miles Spencer
Useful Links
Website: https://milesspencer.com/
X : https://x.com/milesspencer
Linkedin:https://www.linkedin.com/in/milesspencer/
Instagram:https://www.instagram.com/milesspencer/
The Matrix Green Pill Podcast: https://thematrixgreenpill.com/
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