“I travel the world teaching billionaires to surf.” —Tim Sherer
By Chris Dixon
On an overcast day about 20 years ago, a 27-year-old surfer from Long Beach named Tim Sherer was practicing his ski jumps at Mount Baldy, when an overly ambitious attempt sent him full speed into a tree. He was knocked unconscious, swallowing his tongue and completely blocking his airway. His best friend, Tim Inskeep, tried CPR and even the Heimlich maneuver, but nothing worked. Despairing, and with Sherer’s skin turning a ghastly purple, Inskeep looked up, said a prayer and brought all his weight down on his friend’s chest. Sherer’s airway cleared with a loud “pop” and he was suddenly thrust back into the land of the living.
Sherer had spent the previous several years earning a late business degree and taking a few years off to crew on sailboats from the Caribbean clear to Greece and hitching across Europe. Up to that day at Mount Baldy, he had reckoned he was near that point in life when he should settle down and get a “real” job. “The existential moment didn’t happen until the day after the accident,” he says. “I was driving my VW bus out of my neighborhood and waiting for the light to turn green, and I just realized, I just had a major accident that should have killed me. I could go ahead and get a nine-to-five job, and eventually retire, and then what? Go surfing around the world? My number could come up at any moment. I’d heard that all my life but to really realize it experientially—that changed me. I just felt like, the world is my oyster, I should be diving for pearls.”
Sherer dropped everything, and, relying on his sailing ability for work and with little more than a change of clothes and a surfboard, set off for New Zealand, India, Thailand, and Burma. He spent a winter on the North Shore of Oahu, hustled photos of tourists holding parrots on Waikiki, and then migrated to Maui. There, he bought an old Ford Econoline that would double as his home. He woke up most winter mornings on the bluff at Honolua Bay and eventually took an offer to teach surfing at the Lahaina breakwall. He not only found that he enjoyed the wide-eyed shock as his students stood for the first time, but he had a knack as a teacher. “In my mind, I had already arrived,” he says. “If I could give people that much happiness, I could pretty much be happy with my contribution to the world.”
Two years later, largely on the urging of past students, he moved out of the van and founded Goofy Foot Surf School. He’s taught Emilio Estevez and Everclear to surf, and has traveled the world on the dime of Jimmy Buffett and more recently, a pack of dot-com billionaires on a big private jet—once flying to the southern hemisphere just to watch a solar eclipse. He says it’s the time with Buffett though, that has been most revelatory and left him occasionally feeling “like a gypsy in the palace.”
“The kind of people Jimmy surrounds himself with,” he says. “They’re not only great at what they do, they also have amazing attitudes, a great work ethic, and get along so well. I realized he probably pays them fairly well too—otherwise, why would they get up at 3 a.m.? Having those kinds of people allows him to maintain his role as the creative force; he doesn’t have to get mired in all the details of his tours or business. The other thing is, I see his approach to life as he expresses it through surfing. He got back into surfing at 55, and over 10 years I’ve watched him get so much better. He’s on it every day—no matter what the conditions. He’s always said, ‘If it stops being fun, I’ll just quit,’ and I think that’s the key. I was already content and happy with my life, like him. All this other stuff, it’s just been extra credit.”