Gareth Kelly

Bobby White from Dallas, Texas, had it all — good-looking in his late thirties, with, as he put it, “the kind of job you never give up,” as a corporate pilot flying the rich and famous around the world. Then one day his life changed forever.

White suffered a stroke. In an instant, his career was gone, along with his ability to read and write. It took months to heal, during which time he made a decision that would change his life’s trajectory in a way he could never imagine.

He sold everything he owned, bought a C&C 37-foot sailboat, and — along with his two labradoodles, Maverick and Goose — set sail from Texas to the Caribbean.

With enough money to sustain him for about a year — or so he thought — White decided to document his adventure on YouTube. He called his channel Sailing Doodles.

“I thought I had enough money to last me a year in the Caribbean, but it was gone in six months,” White said recently. “But just as I ran out of money, the [Sailing Doodles] channel had gotten enough [financial backing from] followers that I was making just enough to cover expenses.”

Today Sailing Doodles has almost 60,000 subscribers and all the channel’s videos combined just hit 10 million views. At this level, White is generating approximately $4,000 a month from his videos, and that continues to grow. The majority of this income comes from regular subscribers on a crowdfunded platform called Patreon. These fans also get early and exclusive access to content. Approximately 25 percent comes from ads appearing on his YouTube videos, with the rest a combination of donations and various sponsorships.

White and his newest crewmate, Laura, recently stopped at the Santa Barbara harbor for a few nights on their way down the West Coast and Mexico before ultimately heading across the Pacific.

“I was recently in Thailand on vacation,” said White. “I met a guy who had a 50-foot Beneteau sailboat in Vancouver he needed to get from there to [Thailand] in about a year. I was boat-less at the time and thought this was a perfect opportunity for me to keep my adventure going.”

“Being YouTube famous,” he said, isn’t as easy as it looks and requires much more work than people realize. White estimates he spends more than 40 hours a week planning video content, filming, and editing before uploading the finished pieces to his YouTube channel.

“It’s a lot of work, but I love it. I get to sail around the world and meet people who watch our videos,” he said. “We get recognized in stores and on the docks; it’s really cool.” White doesn’t seem to miss his old career much — it looks to me as if he still has it all.

Follow Bobby here.


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