Sailing Doodles Podcast

I’m recording this episode from the roof of my RV in the middle of Black Rock City at Burning Man 2026. Burning Man has grown from a small gathering on a San Francisco beach into a temporary city of more than 70,000 people in the Nevada desert. But after decades of explosive growth, something is changing. Tickets that once sold out almost instantly are now easier to get. The ave...

In this episode, I sit down with Gabriel, whose list of adventures is almost hard to believe. Most recently, he completed the legendary Northwest Passage aboard a 48-foot steel-hull trawler, navigating some of the most remote and challenging waters on Earth. But that’s only one chapter of his story. He has also circumnavigated the globe on a 48-foot sailboat, climbed Mount Evere...

I’ve spent years living and traveling on boats, but lately I’ve been back on the road in the RV — and it got me thinking: which lifestyle is actually better? In this podcast, I compare RV life vs boat life from someone who has lived both. We talk about the cost, maintenance, freedom, comfort, travel, adventure, social life, living with dogs, and all the little things that make e...

For most of human history, people who felt trapped by their circumstances could leave everything behind and head toward a new frontier. They could escape their social class, family reputation, past failures, or limited opportunities and try to build something entirely new. But do those kinds of fresh starts still exist? In this episode, I explore why starting over may be harder ...

In this Ask Me Anything podcast, I answer some of the questions patrons and viewers have been asking most. I start with Nika—whether she’ll be joining me again, how we got along, and what might be next. I also share the scariest experience I’ve ever had at sea: the night my old boat nearly caught fire and sank near Cape Hatteras. I included clips from the original video and expl...