He Bought a $1M Sailboat Before He Knew How to Sail | Salty Podcast #104

Jack Yeager bought a million-dollar-plus sailboat before he knew how to sail—and then learned by taking her across oceans. After selling the software company he had spent eight years building, Jack chose adventure over the sensible next step. His first boat was Phase 8, a 62-foot Beneteau Oceanis Yacht. Over the next five years, he sailed the Mediterranean, crossed the Atlantic, cruised the Caribbean, transited the Panama Canal, explored the Pacific and made it all the way to Alaska. In this candid conversation, Jack tells Cap’n Tinsley about solo sailing a 62-foot yacht, docking among multimillion-dollar boats in Monaco, getting caught in dense fog near Marseille, sailing under a full moon in the Sea of Cortez and watching lightning strike the Freedom Tower above his New York marina. He also shares the wilder side of the journey: being handcuffed by Canadian customs, losing his engine after leaving Alaska, getting caught in 55-knot winds, breaking the boom and facing the moment when he thought, “This is it. I’m gonna die.” This is a story about taking chances, learning the hard way, trusting yourself and actually leaving the dock. ⚓ GUEST Jack Yeager ⛵ BOAT Phase 8 Beneteau Oceanis Yacht 62 CHAPTERS 0:00 Preview: $1M Sailboat, Handcuffs & 55 Knots 0:32 From Detroit to Farm Life & an $800 Tractor 4:37 How Sailing Quieted a Workaholic Mind 6:26 Choosing a 62-Foot Beneteau Before He Could Sail 10:40 Why He Named Her Phase 8 14:02 Mediterranean Sailing: Every Day Was Christmas 16:01 Barcelona, Marseille Fog & the South of France 21:03 Solo Sailing, Monaco & Mediterranean Mooring 29:37 Crossing the Atlantic & Cruising the Caribbean 35:00 The U.S. East Coast & Lightning Over Freedom Tower 43:00 Transiting the Panama Canal 47:13 Venice, Whales & the Sea of Cortez 49:27 COVID, Starlink & Sailing Under a Full Moon 53:29 Insurance Trouble & Montenegro 56:03 Returning to a Locked-Down America 1:01:10 Canadian Customs, a Starter Pistol & Handcuffs 1:04:29 Alaska, No Engine & a Mayday Offshore 1:06:36 55 Knots, No Engine & a Broken Boom 1:08:25 “This Is It. I’m Gonna Die.” & the Coast Guard 1:14:13 Repairs, the 110% Rule & Selling Phase 8 1:23:37 Oligarch Yachts & Why Wealthy People Stay Put 1:27:06 New Skills, Family & the Next Boat 1:32:18 Life on Water, Grief & Choosing Adventure ⛵ Salty Abandon is Cap’n Tinsley from Orange Beach, AL Oct 2020 to Present: 1998 Island Packet 320 Nov 2015 to Oct 2020: 1988 Island Packet 27 Feb 2015 to Nov 2015: 1982 Catalina 25 👕 Salty Podcast SPF Sailor Shirts: https://saltypodcast.myshopify.com 🫶 SUPPORT THE PODCAST: http://patreon.com/SaltyAbandon 💨 AIRLOCK: $30 off with code SALTY30 — https://airlockusa.com/SALTY30 🛠️ PODCAST TOOLS 🎙️ STREAMYARD: Go live like a pro with an easy, browser-based studio for podcasts, interviews and livestreams. https://streamyard.com/pal/d/5430067749060608 🎬 OPUS CLIPS: Turn long videos into short, shareable clips fast. https://tolt.link/saltypodcast ▶️ Salty Podcast YouTube Playlist: https://tinyurl.com/SaltyPodcastPlaylist #SaltyAbandon #SaltyPodcast #Sailing #IslandPacket #cruisinglife