Pulitzer Prize-winning Bill Finnegan profiles tycoon-friendly Kai Lenny for the New Yorker, “(His) most elaborate billionaire bromance has been with Mark Zuckerberg. They went foiling together on Kauai, and the paparazzi caught Zuckerberg looking extra silly.”

And, among other revelations, Kai says, "The big-wave tour sucks" and "I want to surf like Ethan Ewing."

Seven years ago, Bill Finnegan’s Pulitzer Prize-winning memoir Barbarian Days threw me under the bus of a two-day obsessive read. 

I’d dived into Finnegan’s work in the New Yorker before, including an excerpt from the book about his time as a kid in Hawaii (read here) and figured the memoir would be gently entertaining but not especially adventurous.

I imagined a writer with a loosely knotted bow-tie and a drooping moustache. A delicate New York gentleman, a flabby enthusiast.

I’d only penetrated three chapters into the book when we suddenly camping on Maui waiting for Honolua Bay to break and, shortly after, camping on the empty beach at Tavarua for a week and surfing a new discovery called Restaurants.

Finnegan entered my heart a little later when, via email, I asked how surfing could be reported better.

“What I do read is way too advertiser-friendly. BeachGrit seems to be an exception… Surfing is an unusual journalism niche because the interests of the surf industry, which very largely finances the surf media, are fundamentally at odds with the interests of most surfers… They want to ‘grow’ the sport. We’d like it to shrink, reducing crowds.”

The relationship soured, I believe, when Longtom wrote a stinging critique of his essay on Slater’s Lemoore pool, also for the New Yorker. 

Did you not ask about the business plan Bill? It really comes across like you were too busy admiring Kelly the “beautiful boy” whose looks have not deserted him.

Sorry Bill, your book was fab but the essay blew goats. Too much Slater Kool-Aid, not enough fact checking. 

Anyway, in the latest issue of the New Yorker Finnegan examines the life of Kai Lenny, the daring twenty-nine-year-old multi-discipline surfer from Maui.

We learn that his wife Molly is the sister of Dusty Payne, who was dismissive of the relationship with the SUP-riding Lenny, that he believes the big-wave tour is a joke, takes vitamins via an intravenous drip, he’d like to surf like Australian Ethan Ewing and he counts the world’s richest men as pals. 

Kai is discreet about his thing with tycoons. They want to be around him, tech titans especially. Sergey Brin, one of the founders of Google, wants to come out on Kai’s support boat at Mavericks? Sure. “He’s supercool,” Kai says. In 2019, he spent some time on Richard Branson’s private island in the Caribbean, where he taught Sir Richard to kitefoil—we know that mostly because Branson posted video on Facebook of the two of them. But Kai’s most elaborate billionaire bromance has been with Mark Zuckerberg. They went foiling together on Kauai, and the paparazzi caught Zuckerberg looking extra silly. Zuckerberg later described Kai as “magical,” and then introduced his big metaverse gaming play with, among other things, a cringe­worthy virtual-reality skit about foiling with Kai. Even so, Kai has nothing uncharitable to say about him.

Read, or listen, here.