The Bobby White Podcast

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 simply run out of places where your past does not define your future.

I also share a story from my own family history about an ancestor who, according to the story passed down through my family, was the thirteenth son of an English lord. With little chance of inheriting anything, he left England for the New World to build a life of his own.

We discuss the influence of the frontier on American ambition and entrepreneurship, the uncomfortable truth that these lands were never actually empty, and whether technology, space, artificial intelligence, international living, and online businesses have become the new frontiers.

Maybe there are no truly undiscovered places left. But perhaps the biggest frontier has always been the decision to walk away from the life you were given and attempt to create a different one.

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

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 Great Lakes, Maverick, and several other questions submitted by viewers.

There are a few major questions about Maverick and my discussions with Island Spirit that I’m not ready to answer publicly yet. I did answer them fully in the uncut patron version of this podcast.

Become a patron to watch the complete, unedited episode and hear the parts that were removed from the public version.

The full 40-minute documentary about the Cape Hatteras incident is also available as a pay-per-view video on my website.

Watch the Scary moment my boat almost caught fire and sunk:

https://sailingdoodles.com/fire-at-sea/

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

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, what the technicians and builder have done to investigate the problems, and why the generator and battery systems are so important on a yacht designed around electric propulsion.

This isn’t meant to attack anyone or declare the entire concept a failure. New boats often have issues, and this yacht uses relatively new and complex technology. I simply want to be transparent with the audience about the good, the bad, and the decisions still ahead.

Do we continue improving the hybrid system, make major changes, or consider a more conventional setup? At this point, I’m keeping an open mind.

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

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 answer questions about whether I would collaborate with high-performance powerboat channels, meeting up with other content creators while traveling, and how Cougar and Merlin react to the constant stream of new people joining the boat.

Thanks to everyone who submitted questions. Let me know what boat you think would make the best next chapter for Sailing Doodles.

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

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, refundable deposits, and how this idea might actually become a real business.

I still don't know if this will ever happen, but it's already a much better idea because of your feedback.

As always, I'd love to hear what you think. Would you join something like this? What would you change?

Here is Sam's Blog post: https://sveoti.net/an-open-letter-to-bob-white-sailing-doodles-buying-a-yacht-for-you/

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

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 also tell a disturbing offshore story about a friend who hired a delivery captain to sail his yacht from the Mediterranean to the Caribbean. In the middle of the Atlantic, the captain suffered a serious mental-health crisis and threatened to jump overboard. My friend had to change course and divert the yacht to the Azores so the captain could safely get ashore and receive help.

It raises an important question: what do you do when someone panics, becomes unstable, or simply cannot handle being at sea—with nowhere nearby to get off the boat?

Thanks to all the patrons and viewers who submitted questions.

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

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 something like this? What would make you say yes... and what would make you run away?

Leave your thoughts in the comments. Your feedback may completely change this idea.

Fill out the survey if you want to go in on this with me!

https://docs.google.com/forms/d/e/1FAIpQLSf5cP4pI-etL7w761rhN6DqTA81sLEbRsI0KTpkF3Jhf31-kg/viewform?usp=dialog

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 #SailingDoodle

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 boats I’m considering, what makes sense for the channel, what fits the budget, diesel vs gas, speed vs efficiency, and whether a motor yacht could be the right move for the next chapter.

Is this a smart backup plan, or am I just trying to talk myself into buying another boat?

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

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