I would rather be master and commander of my Boston Whaler than be saluting a 5th grader even if I got to be on the best boat ever invented. Despite all the other reasons this is bad, that kid must have turned into a nightmare as an adult.
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Things definitely worked out for Oliver. He arrived in HI a few days ago and managed to amass over a million followers on social media along the way. Whatever his motivations were, he can now continue this lifestyle for a while longer.
I will say, he did a bang up job getting publicity for this trip before he left. I saw many news articles and podcasts about him before I knew who he was. He did a live interview mid ocean with Anderson Cooper. Some random company air dropped him some supplies. It was a rather entertaining story to follow and I wish him the best.
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On the fence here. This “sailing financed by clicks” lifestyle has produced some bad outcomes. Some “sailors” have proceeded to do really stupid things because it would get more clicks. One crew of idiots sailed TOWARDS a hurricane from a safe anchorage, got to the island that was in the path, and waited for their channel to get a million more followers. What ended up happening was the boat was sunk and the already overburdened locals had to provide food and shelter to the crew.
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Reminiscent of Robin Graham and the Dove. 16 year old set out to sail around the world in a 24 foot sailboat. Dismasted twice while sailing but I am using the term freely, “miraculously” survived. National Geographic “followed” him and a book was written “The Dove”. No clicks or social media. Brave or foolhardy, it’s your call.
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I remember reading the Nat Geos as they came out. Too bad about his cat…
Jousha Slocum did a good job of it but even with all his knowledge & experience the sea killed him anyways. Maybe we’re all throwing the dice?
I’m all for the young man. Office life sucks. He was miserable and in poor health and decided to enjoy his life. I feel if his social media experiment didn’t take off, he would have kept up as long as his funds would have allowed before heading back into the drudge of being another cog in the wheel.
Things did work out for him and now he can continue his dream.
Live life man.
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Interview by Jerome Rand (incredibly accomplished solo sailor and author of the book ‘Sailing into the Oblivion’) with Oliver from earlier this week.
You ever notice how everyone thinks that to get in a small sail boat with almost no knowledge of the sea and head out into the ocean is a romantic notion but backpacking across the Sahara seems foolish even though the Sahara is much smaller than any ocean?
The truth about small boat sailing is that you spend 90% of your time sitting on your ass at the tiller. Which makes it a lateral move for office workers. 
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Makes sense. A lot less effort than trudging across a desert which requires actual work. 
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Several years ago I read an old book of diary entries of a retired mailman whose retirement dream was to sail his 23’ sailboat down the Mississippi, to the GoM, then to Mexico or into the Caribbean. A great, funny book of misadventures. He even caught himself on fire & nearly blew his boat up with gasoline & the static from his nylon rainsuit. He made it to the Gulf but the journal entries & book ended there. The book ended with an afterwards from someone else saying he died in Galveston Bay. Either blown overboard in a squall or drowned trying to manually set an anchor? It doesn’t take crossing the ocean for dreamchasers to get killed on small boats.
I really must be doing something wrong, my voyages all involved a lot more than sitting. I need a “how to sit on your ass and still get where you are going” handbook.
Depends where you’re going and your weather window. I’ve done plenty of offshore sails that consisted of darting the sails, not touching them for a few days, and reading through a few books.