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On the show
From 14 epsHosts
Recent guests
Recent episodes
Stop Waiting Until You’re Ready
Jun 24, 2026
19m 56s
The Questions I’ve Been Avoiding… Health, Olivia & What Happens Next
Jun 22, 2026
32m 03s
Is This the End of Sailing Doodles As I Know It?
Jun 19, 2026
17m 10s
My Health Scare: Cancer Fears, Blood Clots, and What Happens Next
Jun 16, 2026
19m 55s
I Really Don’t Want To Do This
May 28, 2026
17m 08s
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| Date | Episode | Topics | Guests | Brands | Places | Keywords | Sponsor | Length | |
|---|---|---|---|---|---|---|---|---|---|
| 6/24/26 | ![]() 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, 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 around the world on a yacht, but this isn’t just about sailing. It’s about risk, freedom, time, work, and the trap of waiting for the perfect moment. I also talk about leaving a good career, the idea of “no risk, no reward,” why doing nothing is also a risk, and why chasing the dream might not work out exactly how you planned — but that doesn’t mean it wasn’t worth doing. You can always get another job. You can’t always get another life. Download the Sailing Doodles Crew App on iOS and come join the Crew! https://apps.apple.com/us/app/sailing-doodles-crew/id6760212361 or join our Patreon http://www.patreon.com/sailingdoodles or become a channel member https://www.youtube.com/channel/UCkDwexrF43p_1QurfKFBCBA/join Donate Via Paypal to help http://www.paypal.me/sailingdoodles Our partners: Want more info in the Island Spirit 525e? Be sure to say you saw it on Sailing Doodles. https://inspiredyachting.com/sailing-doodles-and-inspired-yachting-island-spirit-525e-referral/ Precision Sails: https://www.precisionsailloft.com/request-for-quote/?utm_medium=affiliates&utm_source=sailing-doodles Highfield Boats: https://www.highfieldboats.com/ #Sailing #YachtLife #Thailand #Malaysia #Catamaran #SailingDoodles | 19m 56s | ||||||
| 6/22/26 | ![]() 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 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 Sailing Miss Lone Star return? I also talk about the dogs, the future of the new Island Spirit 525e, what the delivery crew thought of the boat, the electrical and solar questions, the damaged old hull, possible cruising plans, the Med, the Pacific, RV travel, Burning Man, and what’s next for Sailing Doodles. Thanks for all the questions, support, and well wishes. It has been a strange and stressful chapter, but I’m doing my best to stay positive and figure out the path forward. Download the Sailing Doodles Crew App on iOS and come join the Crew! https://apps.apple.com/us/app/sailing-doodles-crew/id6760212361 or join our Patreon http://www.patreon.com/sailingdoodles or become a channel member https://www.youtube.com/channel/UCkDwexrF43p_1QurfKFBCBA/join Donate Via Paypal to help http://www.paypal.me/sailingdoodles Our partners: Want more info in the Island Spirit 525e? Be sure to say you saw it on Sailing Doodles. https://inspiredyachting.com/sailing-doodles-and-inspired-yachting-island-spirit-525e-referral/ Precision Sails: https://www.precisionsailloft.com/request-for-quote/?utm_medium=affiliates&utm_source=sailing-doodles Highfield Boats: https://www.highfieldboats.com/ #Sailing #YachtLife #Thailand #Malaysia #Catamaran #SailingDoodles | 32m 03s | ||||||
| 6/19/26 | ![]() 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 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: whether I can keep sailing long term, what happens to the new yacht if my health changes, whether I’d sell the boat, hire crew, slow down, or pivot the channel completely. I also talk about what retirement might actually look like, whether I regret buying the boat right before this happened, and what happens to the dogs, the crew, the travel plans, and Sailing Doodles as a whole. This one is personal. I don’t have all the answers yet, but this scare has definitely changed how I think about life, health, travel, and the future of the channel. Thanks for watching and for all the support. Download the Sailing Doodles Crew App on iOS and come join the Crew! https://apps.apple.com/us/app/sailing-doodles-crew/id6760212361 or join our Patreon http://www.patreon.com/sailingdoodles or become a channel member https://www.youtube.com/channel/UCkDwexrF43p_1QurfKFBCBA/join Donate Via Paypal to help http://www.paypal.me/sailingdoodles Our partners: Want more info in the Island Spirit 525e? Be sure to say you saw it on Sailing Doodles. https://inspiredyachting.com/sailing-doodles-and-inspired-yachting-island-spirit-525e-referral/ Precision Sails: https://www.precisionsailloft.com/request-for-quote/?utm_medium=affiliates&utm_source=sailing-doodles Highfield Boats: https://www.highfieldboats.com/ #Sailing #YachtLife #Thailand #Malaysia #Catamaran #SailingDoodles | 17m 10s | ||||||
| 6/16/26 | ![]() 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 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 autoimmune, it could be related to pancreatitis, or it could be something else entirely. I’m on blood thinners, getting more testing done, and trying to understand what this means for my future. I also talk about what this could mean for Sailing Doodles, cruising plans, the new boat, and how something like this makes you rethink everything pretty quickly. This is a more personal episode, but I wanted to be honest about where things stand and what I’m dealing with. Download the Sailing Doodles Crew App on iOS and come join the Crew! https://apps.apple.com/us/app/sailing-doodles-crew/id6760212361 or join our Patreon http://www.patreon.com/sailingdoodles or become a channel member https://www.youtube.com/channel/UCkDwexrF43p_1QurfKFBCBA/join Donate Via Paypal to help http://www.paypal.me/sailingdoodles Our partners: Want more info in the Island Spirit 525e? Be sure to say you saw it on Sailing Doodles. https://inspiredyachting.com/sailing-doodles-and-inspired-yachting-island-spirit-525e-referral/ Precision Sails: https://www.precisionsailloft.com/request-for-quote/?utm_medium=affiliates&utm_source=sailing-doodles Highfield Boats: https://www.highfieldboats.com/ #Sailing #YachtLife #Thailand #Malaysia #Catamaran #SailingDoodles | 19m 55s | ||||||
| 5/28/26 | ![]() I Really Don’t Want To Do This✨ | yacht ownershipcustoms regulations+3 | — | Island Spirit 525eSailing Doodles+4 | ThailandMalaysia | yachtsailing+7 | — | 17m 08s | |
| 5/25/26 | ![]() The Truth About My New Electric Catamaran✨ | electric catamaranboat launch+3 | — | Island Spirit 525eSailing Doodles | — | electric catamaranIsland Spirit 525e+5 | Precision Sails | 32m 45s | |
| 5/7/26 | ![]() Is Electric Sailing Finally Safe? Lithium, Lightning & My 210 kWh Catamaran✨ | Electric sailingLithium battery safety+4 | — | Island Spirit 525eCMCE Sertec+1 | — | electric boatslithium batteries+7 | — | 40m 02s | |
| 5/7/26 | ![]() Dating in Paradise Is Harder Than You Think✨ | datingsailing+4 | — | Sailing Doodles Crew AppYouTube | tropical islands | datingsailing+5 | — | 34m 51s | |
| 4/13/26 | ![]() The Bahamas Raised Fees Too Far… Now They’re Reversing Course✨ | cruising feesBahamas+3 | — | boating industry | The Bahamas | Bahamascruising fees+3 | — | 15m 17s | |
| 4/8/26 | ![]() Chloe Opens Up… And Drops Some Big News✨ | personal backgroundcrew dynamics+3 | Chloe | Patreon | — | ChloeSailing Doodles+3 | — | 29m 50s | |
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| 3/21/26 | ![]() Big Updates… New Boat, Chloe, & What’s Next✨ | new boatsailing plans+3 | — | Island Spirit 525e | MaldivesAustralia+1 | sailingcatamaran+3 | — | 47m 55s | |
| 3/14/26 | ![]() This Scares Me… AI Might Replace Creators Sooner Than We Think✨ | AI technologycontent creation+3 | — | — | — | AIcontent creators+4 | — | 21m 33s | |
| 3/11/26 | ![]() How I Moved My Dogs From the U.S. to Thailand (The Real Process) | w/ AE Pets International✨ | pet relocationinternational shipping+5 | James | AE Pets InternationalAE Pets | United StatesThailand | pet shippinginternational pet transport+5 | — | 33m 03s | |
| 2/21/26 | ![]() Why I Bought an Electric Catamaran (And What Could Go Wrong)✨ | electric propulsioncatamaran+4 | — | electric catamaranFountaine Pajot | — | electric catamaranFountaine Pajot+5 | — | 29m 55s | |
| 2/15/26 | ![]() The Pilot Behind Flying Doodles: Emma✨ | aviationcareer journey+3 | Emma | Flying DoodlesSailing Doodles Podcast | — | aviationFlying Doodles+3 | — | 36m 13s | |
| 2/12/26 | ![]() Who’s REALLY Coming to Thailand With Me?✨ | Thailandsailing+4 | — | boatCamping World | Thailand | Thailandsailing+6 | — | 34m 00s | |
| 2/1/26 | ![]() The New Boat Is Almost Done… I’m Flying to Thailand✨ | boat buildingtravel+3 | — | Island Spirit 525e | Thailand | boatThailand+5 | — | 15m 47s | |
| 1/26/26 | ![]() Why Most Sailing YouTube Channels Fail After 2 Years (And Why It’s Harder Now)✨ | sailingYouTube channels+4 | — | — | — | sailing YouTubechannel failure+5 | — | 23m 30s | |
| 1/19/26 | ![]() Who’s Going to Thailand With Me? (New Boat, New Crew, Big Changes) | In this podcast, I answer one of the biggest questions I’ve been getting lately: who’s coming with me to Thailand on the new boat? We talk about the new boat timeline, potential crew lineup, and what this next chapter of Sailing Doodles is really going to look—both on and off camera. I also address questions about Chloe, future appearances, and how I handle bringing new people into the videos while balancing privacy, reality, and the internet’s opinions. We also dive into: Who may be joining the boat in February How crew decisions actually get made Viewer questions about drones, sailing, and life on the water What changes (and what stays the same) with the new boat Big changes ahead—this episode gives you the real story. | 24m 21s | ||||||
| 1/11/26 | ![]() RV Nightmare UPDATE: How Camping World Stepped Up & Made It Right | A month or so ago, I shared a podcast about the nightmare I was dealing with on my RV — and at the time, I hadn’t even gotten to the worst part yet: needing a full engine overhaul. In this episode, I give a full update on everything that happened afterward, how the situation evolved, and how Camping World ultimately stepped up and made things right. It was a long, stressful process, but in the end they took care of the problem, made me whole, and even got me into a newer and better RV. I believe in being fair and transparent — good or bad — and this episode is about how things actually turned out and why I’m satisfied with the resolution. If you’re an RV owner, considering buying one, or just curious how these situations really get handled behind the scenes, this update is worth listening to. | 12m 53s | ||||||
| 12/24/25 | ![]() My Thoughts on the Greg Biffle Crash | In this episode, I share my personal thoughts on the tragic aviation accident involving Greg Biffle and his family. I had the opportunity to meet Greg and his wife Kristina about a year and a half ago at Spanish Cay Yacht Club, and they were incredibly kind, welcoming people. This is not an episode about speculation or assigning blame, but rather about acknowledging the human loss, explaining what is currently known, and offering perspective on how unforgiving aviation emergencies can be—especially shortly after takeoff and in marginal weather conditions. Investigations by the Federal Aviation Administration and the National Transportation Safety Board are ongoing, and it will be many months before definitive answers are available. My thoughts and condolences are with everyone affected by this heartbreaking tragedy. | 18m 43s | ||||||
| 12/23/25 | ![]() Relationships, Insurance & the New Boat - Ask Me Anything | You asked some tough questions, so it’s time to answer them. In this Q&A episode I cover everything from crew changes and relationships, to insurance and the new boat, along with sailing myths, health insurance while cruising, provisioning mistakes, and what’s coming next for Sailing Doodles and the spin-off channel. Nothing scripted, nothing off limits, just honest answers to the questions you’ve been sending in. Thanks to all the patrons and supporters who keep this channel going and help shape these conversations. Enter the contest here: https://raffall.com/398138/enter-raffle-to-win-sailing-doodles-sailboat-hosted-by-sailing-doodles Want more info in the Island Spirit 525e? Be sure to say you saw it on Sailing Doodles. https://inspiredyachting.com/sailing-doodles-and-inspired-yachting-island-spirit-525e-referral/ | 39m 07s | ||||||
| 12/7/25 | ![]() Everything You Think About Sailing Is Wrong | Ever wondered what sailing is really like? After years living aboard, crossing oceans, rescuing boats, breaking boats, and teaching new crews how to sail, I’ve heard every sailing myth in the book… and today we’re busting the big ones. In this episode, we break down the 12 most common (and most misleading!) sailing myths that stop people from getting on the water — including the truth about boat costs, storms, sharks, catamaran safety, anchoring, YouTube crew life, and whether you actually need experience before buying a boat. Whether you’re dreaming of cruising, already sailing, or just love the lifestyle, this podcast will give you a real-world look at what sailing is actually like… the good, the bad, and the hilarious. To apply: Send a short introduction video uploaded to YouTube (public or unlisted) and email me the link. Tell me who you are, why you want to join, and what makes you the perfect fit. cruise@sailingdoodles.com Patreon members will get to watch the submissions and help me decide who joins the crew. If you want to be part of the process, join here: https://www.patreon.com/sailingdoodles Enter the contest here: https://raffall.com/398138/enter-raffle-to-win-sailing-doodles-sailboat-hosted-by-sailing-doodles Want more info in the Island Spirit 525e? Be sure to say you saw it on Sailing Doodles. https://inspiredyachting.com/sailing-doodles-and-inspired-yachting-island-spirit-525e-referral/ | 23m 15s | ||||||
| 12/1/25 | ![]() The Insurance Saga Is Finally Over… Here’s What I Can Say | After many delays, stress, paperwork, and uncertainty… the insurance saga is finally over. As most of you know, the delivery crew had a major mechanical failure last year that led to my boat being totaled. Since then, I’ve been working through the long insurance process behind the scenes. I can’t share specific numbers, terms, or private details because of my NDA — but I can walk you through what the experience was like, what I learned, and how this affects the future of Sailing Doodles. In this episode I cover: What I can legally say about the resolution What this means for the new boat build And what’s next for the channel Thank you to everyone who supported me during this ordeal — the comments, messages, and patience meant more than you know. Time to move forward and get back to sailing! To apply: Send a short introduction video uploaded to YouTube (public or unlisted) and email me the link. Tell me who you are, why you want to join, and what makes you the perfect fit. cruise@sailingdoodles.com Patreon members will get to watch the submissions and help me decide who joins the crew. If you want to be part of the process, join here: https://www.patreon.com/sailingdoodles Enter the contest here: https://raffall.com/398138/enter-raffle-to-win-sailing-doodles-sailboat-hosted-by-sailing-doodles Want more info in the Island Spirit 525e? Be sure to say you saw it on Sailing Doodles. https://inspiredyachting.com/sailing-doodles-and-inspired-yachting-island-spirit-525e-referral/ | 34m 31s | ||||||
| 11/28/25 | ![]() Sailors Invented Half Our Language?! | Ever wonder where everyday expressions like “three sheets to the wind,” “overboard,” “the bitter end,” or even “windfall” actually came from? Turns out, tons of common words in English were invented by sailors, pirates, and old-school sea captains, and today we still use them without even thinking about it. In this episode of the Sailing Doodles Podcast, I break down over 80 everyday words and sayings that all started on ships — from naval terms, pirate slang, emergency commands, rigging language, and old maritime traditions. Some of these are obvious… but most of them will absolutely blow your mind! If you enjoy sailing, history, language, or just fun trivia, this is a super entertaining deep dive into how much of modern English came from life at sea. Fair winds and following seas — and thanks for listening! If you want to be part of the process, join here: https://www.patreon.com/sailingdoodles | 35m 20s | ||||||
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