Cyclist ‘Phil the Thrill’ Finds His Hill

Retired pro cyclist Phil Gaimon sets out to tackle Trancas Canyon Road in an effort to set a new Everesting record—an endurance race involving a cyclist climbing the same hill dozens of times in a row until they have climbed the equivalent of Mount Everest.

Retired professional cyclist Phil Gaimon, 35, was spotted a few weeks ago hurtling down the steep part of Trancas Canyon Road at 60 miles per hour. Once he reached the bottom of the hill and turned around, he rode back up the torturous incline to the top. Then kept repeating. After a months-long search, Gaimon chose this specific hill for his second official Everesting attempt.

The hill is a brute. Malibu residents can be seen daily huffing and puffing their way up and then down as part of their exercise routines. Most could not imagine riding up and down it on a bike 67 times without stopping, yet that’s what Gaimon needs to do in order to regain the world record for Everesting.

Sports writers have described the Everesting challenge as everything from “truly masochistic” to “fiendish.” Everesting is when cyclists ascend and descend a chosen hill enough times to cumulatively climb 29,029 feet—the elevation of Mount Everest. The competition has become incredibly popular during COVID-19, largely because it’s a worldwide competition that can be done solo. Cyclists from all nations have continued to break each other’s records over the past year.

Gaimon himself held the world record for Everesting for all of four days earlier last year. The hill on which he made his stand was on Mountain Gate Drive in Beverly Hills, which he Everested in 7 hours and 52 minutes, beating the previous record by over 37 minutes, on May 11, 2020. Unfortunately, he was then bested by pro mountain biker Keegan Swenson shortly after and vowed to take back the title. 

Since then, American cyclist Sean Gardner, 26, set the current Everesting world record on Oct. 5, 2020, with an official time of 6:59:38—the first cyclist to Everest in less than seven hours.

“My goal is to break the Everesting world record again,” Gaimon said. “Finding the right hill is critical.” The world record was being broken so frequently that he decided to hold off his next attempt for a few months to see if the winning times would plateau. He continued to train, which meant endurance rides and hill repeats, mostly around Malibu.

He looked for a hill that was “super steep and like straight up and down hill, with no mailboxes and no traffic.” He looked at thousands of possible hills all over the area and nothing quite worked. One day he was riding in Malibu, remembered Trancas Canyon Road where he’d ridden in the past and checked it out again.

“It’s super close to what I was looking for, and right in my backyard in Malibu,” Gaimon said. “There’s a park at the bottom with 15-20 houses on the whole street, and it’s steep enough.” 

He likes the fact that the steepness allows for speeds of up to 60 miles per hour down hill. The only drawback is that the hill, at 440 feet, wasn’t quite long enough to be ideal—with 67 trips up and down, he would also have to turn around 67 times, which loses time. 

Gaimon had a professional analysis done of the hill, and found it was mostly a 20 percent grade—which is incredibly steep. By contrast, the maximum grade for most federally funded highways is six percent.

“It was too painful to ride, and then not hard enough across a flat portion, and then way too painful again,” Gaimon joked. He tested it out by doing numerous laps up and down, then had some mechanical adjustments made to his bike related to the hill’s steepness.  

Gaimon made his first actual Everesting attempt on Trancas Canyon Road on Jan. 14. He showed up with a small entourage of spotters and videographers to make sure everything stayed safe, and attracted a few curious local onlookers. Unfortunately, four-and-a-half hours into the ride, he called it off because the air temperature soared and it got too hot. He also realized they miscalculated the turnaround point. He said he’ll definitely try again, but doesn’t have an exact date. 

Gaimon was a pro cyclist for 10 years until beginning his YouTube show in 2016, “Worst Retirement Ever,” now with nearly 100,000 subscribers. Some of the most recent episodes feature Trancas Canyon. He’s also known for the two-day “Phil’s Cookie Fondo” annual cycling fundraising event benefitting Chef’s Cycle and No Kid Hungry. It features three cycling courses through the Santa Monica Mountains that Phil designed himself—the 46-mile Sugar Cookie ride, the 87-mile Chocolate Chip ride and the 118-mile Double Fudge.