Sailing Doodles Podcast

In this special episode, I’m sharing my full life story — from my childhood sailing a Sunfish on my grandparents’ lake, to my aviation career flying Gulfstreams for celebrities, to the stroke that ended my flying days, and how that ultimately led to creating Sailing Doodles. It’s been a wild ride: flying rockstars around the world, living in Nigeria and Dubai, surviving a medical crisis, and then finally selling everything to chase the dream of sailing full time. I’ll take you through the twists, setbacks, and adventures that brought me here today. If you’ve ever wondered how Sailing Doodles started — this is the story behind it all.

For years I assumed I had another 5–10 years as a content creator before technology really started disrupting things. After seeing how fast AI video is advancing… I’m not so sure anymore. AI can now generate voices, scripts, music, and even realistic video scenes. I recently watched several AI-generated reels and videos that honestly fooled me at first. And the scary part is this technology is improving incredibly fast. In this episode I talk about: • AI-generated videos that fooled me • How fast AI video is improving • Why creators might actually lose this battle • How AI could flood YouTube with unlimited content • Whether real creators will still be able to make a living Even if people prefer real creators, the amount of AI content coming could make it almost impossible to compete. But there may still be one thing AI can’t replicate… real life experiences. So is this the end of creators, or just the next evolution of content creation?

Ever wondered how hard it is to move pets internationally? visit AE Pets https://www.aepetsgo.com In this episode of The Sailing Doodles Podcast, I break down exactly what it took to move my two dogs from the United States all the way to Thailand. There are a lot more steps involved than most people realize — health certificates, government approvals, airline regulations, quarantine rules, and more. To help explain the process, I sit down with James from AE Pets International, the company that handled the logistics of transporting my dogs. We talk about how international pet shipping works, what pet owners need to know before moving abroad, and how professionals coordinate everything from paperwork to flights to make sure pets arrive safely. If you’re planning to travel or relocate overseas with your pets, this episode will give you a behind-the-scenes look at the process and how to make it much easier. Topics we cover: • The paperwork required to ship pets internationally • Health certificates and vaccination requirements • Airline cargo vs passenger transport • What happens when pets land in a new country • Common mistakes pet owners make • How pet shipping companies simplify the process Whether you're moving abroad, sailing around the world, or just curious about how pets travel internationally, this episode will walk you through everything. become a patron! https://www.patreon.com/sailingdoodles

In this episode of The Sailing Doodles Podcast, I dive into one of the biggest decisions I’ve ever made… going all-electric with the new catamaran. Why did I choose an electric propulsion system? How does it compare to boats like Fountaine Pajot’s electric cats? What are the real risks — lightning, reliability, long-term maintenance? And what spares and tools will I be carrying to prepare for worst-case scenarios? Then we pivot into your most asked personal questions… – Will there be rotating crew in Thailand? – What’s happening with Flying Doodles and Emma? – Can I get my pilot’s license back? – Does Chloe ever get tired of keeping her real name private? – And yes… how dating works when you’re constantly moving. We also talk YouTube growth “experts,” long-term life plans, the Bronco, and my favorite episode I’ve ever created. Big changes ahead. Let’s get into it.

In this episode of The Sailing Doodles Podcast, I sit down with Emma — the host of Flying Doodles — to talk about her aviation journey, career path, and what really goes on behind the scenes of the channel. From her flight training and early experiences in the cockpit to where she sees her aviation career heading next, Emma shares stories you haven’t heard before. We also talk about the future of Flying Doodles, upcoming projects, and what excites her most about aviation right now. If you’ve been watching Flying Doodles and wondering who Emma really is and how she got here — this is the episode for you. Make sure you check out @flyingdoodles here: https://www.youtube.com/c/FlyingDoodles/ Let us know in the comments: What should we film next on Flying Doodles? #FlyingDoodles #AviationPodcast #PilotLife #SailingDoodles

In this Ask Me Anything episode, I answer the question everyone keeps asking… Who is actually coming with me to Thailand to pick up the new boat? There’s been a lot of speculation about crew, plans, and what’s happening next — so I finally address it. I also talk about: Whether Chloe is joining me Lauryn? Thailand flotilla details What I actually have planned once I get there The current status of the boat raffle RV updates and the Camping World situation Craziest sailing mistakes I’ve ever seen And how to get hired on a sailboat Big year ahead. New boat. New adventures. Possibly new crew. Let’s get into it.

This one feels surreal to say out loud — the new boat is getting very close to completion. In this update, I share where the build is at, what’s left to finish, and why this moment feels different than anything before. After months (and years) of planning, I’ll be flying to Thailand next month to finally step onboard and start the next chapter. I know a lot of you have been following this journey from the beginning, and I can honestly say… I’m just as excited (and nervous) as you are. Thanks for sticking with me — things are about to get really interesting. 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/

Sailing YouTube looks easier than ever — bigger audiences, better cameras, more success stories. But the reality? It’s harder now than when I started, and most sailing channels don’t even make it past year two. In this episode, I break down why channels really fail — not because they can’t sail, but because they run out of money, burn out, struggle with people, or misunderstand how YouTube actually works today. I talk honestly about how long it took me to break even, living on beans and rice, dealing with burnout that never really goes away, why subscribers matter less than they used to, and why AI might be the biggest challenge creators face next. This isn’t meant to discourage anyone — it’s meant to prepare you. If you’re thinking about starting a sailing channel, or you’ve wondered why so many disappear, this episode is for you.

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.

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.

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.

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/

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/

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/

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

What upgrades are actually worth the money on an older sailboat… and which ones you should avoid? In this episode of The Sailing Doodles Podcast, I break down the most valuable upgrades I’ve done across all the boats I’ve owned — from my classic CT-56 to the newer catamarans and charter boats we’ve sailed. I cover which improvements truly make your boat safer, easier to sail, and more enjoyable… and which “fancy” upgrades usually end up being a waste of money. If you’re shopping for an older cruising boat or planning a refit, this episode will save you thousands. Topics Covered Why buying a boat already upgraded is often cheaper Rigging, sails, and critical safety upgrades Ground tackle & anchoring systems worth investing in Autopilots, instruments & navigation upgrades Electrical systems, lithium, solar & charging Refrigeration: why it’s usually a later priority Comfort upgrades: electric winches, watermakers & more What to skip… and what will absolutely transform your cruising About the Channel I’m Bobby from Sailing Doodles. I sail, travel, and document the adventure while running my YouTube channels from around the world — from the Caribbean and the Bahamas to the Mediterranean and beyond. If you enjoy the episode, hit subscribe and check out the sailing raffles, flotillas, and behind-the-scenes content! 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/ 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

The fans didn’t hold back on this one… In this Q&A episode, I answer YOUR questions about the new catamaran, future sailing plans, past crew, and even a few spicy ones about “hot babes” and babies on board We talk about: • Updates on the new Island Spirit 525e catamaran (Hull #5) • Future cruising plans in Thailand and the Mediterranean • Crew, relationships, and how the channel has evolved • Life as a full-time liveaboard and YouTuber • Gear, filming setups, and how the dogs handle land life Thanks to everyone who submitted questions — I read as many as I could! Watch next: [link to related podcast or vlog] Join the Sailing Doodles community: Patreon / Podia links Follow along on Instagram: @SailingDoodles #SailingDoodles #Podcast #QandA #SailingLife #BoatLife 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/ 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

I just bought a brand-new RV… and it didn’t even make it off the lot before breaking down. Within minutes, the engine started smoking and I quickly realized the EGR cooler had failed, dumping coolant straight into the exhaust. In this episode of The Sailing Doodles Podcast, I talk about what happened, how I diagnosed the issue, and what comes next. The dealer says they’ll cover the repair — but we’ll see what really happens. I’ll share what I’ve learned from years of owning boats, planes, and RVs about mechanical failures, warranty claims, and how to handle breakdowns the smart way. Topics: How to spot EGR cooler failure symptoms What happens when coolant enters the exhaust Towing and dealer negotiations Lessons learned when buying new rigs Listen on YouTube, Spotify, or anywhere you get your podcasts. #RVBrokeDown #RVPurchase #EGRcooler #SailingDoodlesPodcast 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/ 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

In this episode, I dive into how sailors and cruisers deal with one of the biggest threats on the ocean — hurricanes. Fifty years ago, crossing an ocean meant hoping you didn’t run into a storm. There was no internet, no satellite tracking, and little warning. Today, we carry a weather computer in our pocket, with live hurricane data, Starlink connectivity, and routing tools that can literally save lives. We’ll talk about: How hurricane forecasting has changed in just a few decades The role of Starlink and modern weather apps at sea What the “hurricane box” is — and why insurance won’t cover you inside it How cruisers migrate north and south each year to stay safe Where sailors ride out storms (the famous “hurricane holes”) The truth about insurance loopholes and “named storm” clauses Real stories, lessons learned, and what it’s like to live with hurricane season as a full-time cruiser If you’ve ever wondered how modern sailors dodge hurricanes — or how it was done before the digital age — this episode will blow your mind. Leave a comment: Where do you go during hurricane season? Subscribe for more real-life sailing stories, tech talk, and behind-the-scenes of the cruising lifestyle. #SailingDoodles #HurricaneSeason #SailingPodcast #CruisingLife #StarlinkAtSea #SailingTips

A Queensland superyacht agent was offered $300,000 for a “simple” job — help two divers enter Australia. Days later, one diver was dead, another had vanished, and 100 kilos of cocaine were floating in Newcastle Harbor. In this episode, Captain Bobby White of The Sailing Doodles Podcast breaks down the true story of James Blake Blee — how financial desperation led to a deadly smuggling plot, what “parasite smuggling” really is, and why this growing underwater drug tactic is spreading around the world. All details sourced from court reports, News.com.au, ABC Australia, and VICE News investigations. 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/ 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