Burning Man Is Getting Older, More Expensive… and Losing Money
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 g...
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Sailing Doodles Podcast
Bobby and Laura are sailing around the world with two full size labradoodles and document their adventures as they go! In the podcast series they will get more in depth on topics related to...
Episodes
20 of 151 episodes
He Climbed Everest, Sailed Around the World & Conquered the Northwest Passage
In this episode, I sit down with Gabriel, whose list of adventures is almost hard to believe. Most recently, he completed the legendary Nort...
RV Life vs Boat Life — Which Is Actually Better?
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...
There Are No New Frontiers Left
For most of human history, people who felt trapped by their circumstances could leave everything behind and head toward a new frontier. They...
Will Nika Be Coming Back?
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...
My New Yacht Has Some Problems—Here’s the Full Story
Owning a brand-new hybrid-electric yacht has been exciting—but it has also come with a much steeper learning curve than expected. In this po...
What Kind of Boat Should I Buy Next?
I’m back with the second half of my patron Q&A, and this time we’re talking about what kind of boat I should buy for my next adventure. Woul...
I Was Wrong... Here's the Better Plan
A few weeks ago I shared an idea that I thought could completely change the way people experience luxury sailing. Then I asked for your feed...
Why Does My Crew Keep Leaving?
In this patron Q&A podcast, I answer some of the most common—and most interesting—questions viewers have been asking. I talk about what happ...
I'm Buying YOU a Yacht?
What if there was a better way to own a luxury yacht? I've been working on a business idea that I honestly can't decide is brilliant... or c...
Getting a Motor Yacht Instead?
In this episode, I talk through a big realization about the future of Sailing Doodles: because of location, weather, and cruising seasons, I...
Stop Waiting Until You’re Ready
Most people have a dream. Maybe it’s sailing around the world, building a cabin in the mountains, starting a farm, opening a business, movin...
The Questions I’ve Been Avoiding… Health, Olivia & What Happens Next
In this episode, I’m answering your questions from Patreon, YouTube members, and the Sailing Doodles app. We start with the big one: my rece...
Is This the End of Sailing Doodles As I Know It?
After a big health scare, I’ve had to ask myself some hard questions about the future of Sailing Doodles. I just bought my dream yacht, but...
My Health Scare: Cancer Fears, Blood Clots, and What Happens Next
In this episode, I talk about the medical issue that suddenly interrupted my life and my plans for Sailing Doodles. It started with abdomina...
I Really Don’t Want To Do This
After years of delays, setbacks, and finally taking delivery of my new Island Spirit 525e… I’ve run into another problem. Because of Thailan...
The Truth About My New Electric Catamaran
After years of planning, delays, factory visits, and a whole lot of frustration, my new Island Spirit 525e electric catamaran is finally in...
Dating in Paradise Is Harder Than You Think
Dating while sailing around tropical islands sounds like it should be easy… but the reality is a lot more complicated. When you live on a bo...
Is Electric Sailing Finally Safe? Lithium, Lightning & My 210 kWh Catamaran
Electric boats are no longer some far-off future idea — they’re here, and my new Island Spirit 525e is a perfect example. With a 210 kWh bat...
The Bahamas Raised Fees Too Far… Now They’re Reversing Course
The Bahamas pushed cruising fees too far in 2025, and the boating industry says the fallout was immediate: fewer boats, weaker marina occupa...