Sailing Doodles, Living the YouTube Dream at Sea [Ep. 79]

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Bobby White was a successful commercial pilot until having a stroke at the age of 38. He couldn’t fly, his real estate career didn’t take, so… he sold everything, bought a boat, and started posting his adventures to YouTube as “Sailing Doodles.” A few years later he’s getting 25 million views a month.

It might look like a permanent vacation, but it’s really not. Bobby’s constantly working between sailing, boat maintenance, and YouTube, especially because he didn’t come into it all with formal training. His first journey from Texas to the Caribbean set in motion what would eventually become a well-scheduled, efficient media machine.

And then… there’s the disaster. Rough seas and a series of problems combined to force a Coast Guard call and $100,000 of damage to his boat — but Bobby’s incredible community rallied around him to help with a very unique pay-per-view fundraising effort.

Bobby’s our first travel YouTuber, and the logistics of all that entails are pretty interesting. And yes, everyone around him thought he was crazy. Patrons jump in to ask about the tech process, how Bobby mails SD cards to his mom, how his dogs adapted to sailing life, and his secret love of Yacht Rock.

Thanks to Bobby for grabbing a hotel to do this show and to everyone who showed up to listen to this extremely unique episode of TCU. As always, a special thanks to the Patrons who make this show happen every week!

Sailing Doodles: https://www.youtube.com/c/Sailingdoodles/featured

🎥 CREDITS:

Hosts: Kevin Lieber and Matt Tabor

Produced and Edited by Ben Webster → https://twitter.com/benwebsterTCU 

Theme by Mega Drive → http://megadrivemusic.com 

Opening Animation: Kidmograph

City Animation: Eric Langlay

“The Create Unknown” is produced by Unknown Media.

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