Sailing Doodles Podcast

30:35

Why I’m Selling My 56-Foot Sailboat

Sailing Doodles Podcast ·

2026/10/04

It probably looks like my 56-foot CT56 is falling apart, but there’s more to the story. After sitting on the hard unattended for over a year, I’m compressing a year’s worth of maintenance into just a few weeks. In this episode, I break down what’s gone wrong, what I’ve fixed, what still needs to be done, and why I’ve decided it’s time to sell Nauti Dogs. I’m ready for something different — a smaller motor yacht for cruising Florida, the Bahamas, and maybe the Great Loop. The listing for sale

en

17:57

Aerosmith Never Knew Their Private Jet Had a Serious...

Sailing Doodles Podcast ·

2026/09/29

Before Sailing Doodles, I spent years flying Gulfstream private jets around the world, and for about six to eight months I was one of the primary copilots flying Aerosmith on tour. Most nights we'd watch the show, leave halfway through to get the jet ready, then fly the band to their next city as soon as they came off stage. But one night, flying Aerosmith home to Boston, I noticed something strange in the cockpit. One of our fuel temperature gauges was climbing rapidly—and eventually pegged at

en

36:26

What's Really Happening with my Electric Catamaran?

Sailing Doodles Podcast ·

2026/09/29

In this episode I’m answering your questions about what’s happening with my electric catamaran, whether I’m keeping it, selling it, or moving back to diesel.

en

14:02

I Flew Snoop Dogg… Then Customs Brought the Drug Dogs

Sailing Doodles Podcast ·

2026/09/21

Back in 2004, I was a young Gulfstream III copilot flying celebrities around the world—and one of our regular passengers was Snoop Dogg. On one particular trip, our company was bringing Snoop and his entourage home from Brazil. I joined the trip in Brownsville, Texas, where the airplane had to clear U.S. Customs and Immigration before continuing on to California. Customs knew who was coming, and they were ready. Officers met the airplane with a drug dog and thoroughly searched the jet. They even

en

44:06

Superyacht Ownership Explained by an Actual Owner

Sailing Doodles Podcast ·

2026/09/15

What is it actually like to own a superyacht? I sit down with my friend Bob, who has owned yachts ranging from 65 feet all the way up to 165 feet, to get an inside look at the reality of superyacht ownership. We talk about what these boats really cost to buy and operate, hiring and managing crew, maintenance, scheduling, fuel, marinas, itineraries, and all the logistics that come with owning a yacht of this size. If you’ve ever dreamed about owning a superyacht—or just wondered how the

en

23:08

Burning Man Is Getting Older, More Expensive… and...

Sailing Doodles Podcast ·

2026/09/03

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 average Burner is getting older, fewer people in their 20s are attending, and the cost of participating continues to climb

en

89:44

He Climbed Everest, Sailed Around the World &...

Sailing Doodles Podcast ·

2026/08/25

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 Everest, completed the Seven Summits, and swam the English Channel. We spend nearly an hour and a half talking about what it

en

27:02

RV Life vs Boat Life — Which Is Actually Better?

Sailing Doodles Podcast ·

2026/08/19

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 each lifestyle amazing — and frustrating. RV life is definitely easier in a lot of ways, but does boat life offer

en

19:34

There Are No New Frontiers Left

Sailing Doodles Podcast ·

2026/08/02

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 today than it was for previous generations, why fewer people are willing to risk everything, and whether the world has

en

35:31

Will Nika Be Coming Back?

Sailing Doodles Podcast ·

2026/08/01

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 explain what happened from my perspective. I also give an update on my health, future cruising plans, the Great Loop, the

en

19:14

My New Yacht Has Some Problems—Here’s the Full Story

Sailing Doodles Podcast ·

2026/07/27

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 podcast, I give an honest update on my first few weeks aboard the Island Spirit 525e. I walk through the technical issues we’ve experienced so far, including repeated generator faults, problems within the drive-battery system, charging limitations, and some of the other complications that have interrupted our cruising through Thailand. I explain what happened,

en

20:28

What Kind of Boat Should I Buy Next?

Sailing Doodles Podcast ·

2026/07/21

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. Would a diesel Sea Ray-style express cruiser work for Florida, the Keys, the Bahamas, and potentially farther into the Caribbean? Or would I be better off with a trawler, a traditional motor yacht, or something designed for longer-range cruising? I discuss the features, size, speed, dinghy setup, and practical limitations I would consider before buying. I also

en

25:30

I Was Wrong... Here's the Better Plan

Sailing Doodles Podcast ·

2026/07/17

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 feedback. Hundreds of comments later—and one incredibly detailed blog from a viewer—I realized I had made some major mistakes. In this episode I explain what I got wrong, why the original model probably wouldn't work, and the new direction I'm considering. We dive into whole-boat memberships vs. cabin memberships, pricing, charter economics, premium weeks,

en

38:12

The Captain Threatened to Jump Overboard Mid-Ocean

Sailing Doodles Podcast ·

2026/07/15

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 happened with recent crew members, how I find people to join the boat, the couple who were supposed to launch a Sailing Doodles spin-off channel, whether I’m in a relationship, my changing thoughts about Thailand, plans for the new catamaran, the Mediterranean, the flotilla, and whether I’m seriously considering buying a motor yacht and doing the Great Loop. I

en

21:28

I'm Buying YOU a Yacht?

Sailing Doodles Podcast ·

2026/07/13

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 completely crazy. Imagine having access to a $1.4 million sailing catamaran that cruises the Mediterranean, Caribbean, Thailand and beyond, without having to buy the whole boat yourself. In this episode I walk through the concept, the numbers, the challenges, and the biggest objections I've already heard. Most importantly, I want YOUR feedback. Would you join

en

21:39

Getting a Motor Yacht Instead?

Sailing Doodles Podcast ·

2026/07/08

In this episode, I talk through a big realization about the future of Sailing Doodles: because of location, weather, and cruising seasons, I may only be able to film on my new catamaran about four months a year. That creates a real problem. If I want to keep making consistent boat content, I may need a second boat. So I’m thinking about buying a smaller motor yacht to keep in Florida and use for cruising the Bahamas, and maybe even doing parts of the Great Loop. I go through the different types of

en

19:56

Stop Waiting Until You’re Ready

Sailing Doodles Podcast ·

2026/06/24

Most people have a dream. Maybe it’s sailing around the world, building a cabin in the mountains, starting a farm, opening a business, moving overseas, or just walking away from a life that looks successful on paper but doesn’t actually make you happy. But most people never do it. Not because the dream is impossible, but because they keep waiting until they’re ready. In this episode, I talk about why I believe you have to set a date, prepare as best you can, and then go. My dream was sailing

en

32:03

The Questions I’ve Been Avoiding… Health, Olivia &...

Sailing Doodles Podcast ·

2026/06/22

In this episode, I’m answering your questions from Patreon, YouTube members, and the Sailing Doodles app. We start with the big one: my recent health scare, the blood clots and thrombosis, whether it could be connected to my past stroke, how medical care has been overseas, and what recovery might look like from here. Then we get into the questions everyone always wants answered: What’s going on with Olivia? Is she coming back to the boat? What happened with the Brazilian girl? Will Chloe or

en

17:10

Is This the End of Sailing Doodles As I Know It?

Sailing Doodles Podcast ·

2026/06/19

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 now I’m dealing with blood clots and thrombosis in major abdominal veins, and I still don’t have all the answers about what caused it or what the long-term prognosis looks like. For a while, there was even concern it could be cancer, which thankfully seems to have been ruled out. In this episode, I talk honestly about what this could mean for my future:

en

19:55

My Health Scare: Cancer Fears, Blood Clots, and What...

Sailing Doodles Podcast ·

2026/06/16

In this episode, I talk about the medical issue that suddenly interrupted my life and my plans for Sailing Doodles. It started with abdominal pain that I thought might be something minor, but after hospital visits, scans, and more tests, doctors found inflammation around my pancreas and blood clots in the portal vein. For a short time, there was a real fear that it could be pancreatic cancer, which was obviously terrifying. Right now, I’m still waiting on a proper diagnosis. It could be something

en

All Episodes

Similar Podcasts

وجوه من الـظل

Medi1 Podcast

The Morning Hustle Podcast

Urban One Podcast Network

Parallax Views w/ J.G. Michael

J.G.

Chicks in the Office

Barstool Sports

Um Espião no Kremlin

Observador