Today’s guest is Xavier Helgesen, a brilliant entrepreneur, investor, and co-founder of Enduring Ventures, a modern-day Berkshire Hathaway acquiring overlooked, cash-flowing businesses with the goal of holding them forever. Recorded during Enduring Ventures' annual shareholder gathering, Ted and Xavier discuss the philosophy and mechanics of permanent capital, the hidden pitfalls of venture capital and private equity, and the surprising power of owning simple, Main Street businesses.

Xavier also shares lessons from his journey as a pioneering social entrepreneur, from building Better World Books into one of the world’s largest book resellers to founding Zola Electric, a solar energy company powering millions of lives across East Africa. They explore the complexities of balancing profit and purpose, why effective altruism falls short, and how Xavier’s experiences shaped his pivot toward strategic investing and entrepreneurship.

If you’re interested in permanent capital, thoughtful investing, and practical insights into entrepreneurship, this conversation is packed with wisdom.

Enjoy!

In this episode, I sit down with Mark Synnott—climber, writer, explorer—for a wide-ranging conversation about the Franklin Expedition and the deeper human drive to venture into the unknown. This may be the greatest survival tale never told.

We talk about Mark’s journey through the Northwest Passage in search of clues, the myth of the open polar sea, and what Inuit oral history suggest really happened to Franklin and his men.

We also get into Mark’s own expeditions—from remote climbs in Baffin to his quest to find Sandy Irvine’s body and the lost Everest camera. There’s a lot here about the psychology of adventure, the messiness of expedition dynamics, the tension between storytelling and truth, and what it means to raise a family while chasing risk.

If you’re into exploration, obsession, and the blurry line between noble ambition and madness—this one’s for you.

Ted sits down with Kris Tompkins, longtime CEO of Patagonia and one of the world’s most influential conservationists. Kris shares her journey from building Patagonia with Yvon Chouinard to her transformative conservation work, rewilding millions of acres in Chile and Argentina alongside her late husband, Doug Tompkins.

Discover her insights into the early days of Patagonia, groundbreaking conservation projects like Pumalín Douglas Tompkins National Park, and the rewilding of species in Argentina’s Iberá wetlands. Kris also reflects on her philosophy of life, conservation, and the power of teamwork in achieving lasting change.

Tune in for an inspiring conversation with a true pioneer in environmental stewardship.

In this episode, Jim McKelvey, cofounder of Block Inc, delves into the critical role timing plays in both business and life, offers an insider’s look at Federal Reserve decision-making during economic crises, and unveils his plan to accelerate life-saving treatments through more efficient clinical trials. From entrepreneurial insights on leveraging machine learning for underwriting risk to his thoughts on wealth, frugality, and personal happiness, Jim’s perspectives are refreshingly down to earth and illuminating. Perfect for entrepreneurs, healthcare professionals, and anyone eager to understand how new technologies reshape finance and medicine, this episode delivers unparalleled lessons on creativity, leadership, and disruption.