(Phil and Cameron at Whiskey Tango Fondo, Phil's gravel cycling event)
For this edition of Weiss Wednesday, we caught up with longtime friend and Weiss client Phil Gaimon.
Phil spent his twenties as a professional cyclist before turning retirement into an unexpected second career. Today, he’s an author, YouTube creator, charity event organizer, and the man behind Worst Retirement Ever, where he continues to train, chase records, and find new ways to push himself on the bike.
We sat down with Phil to talk about turning 40, what cycling has taught him about patience and mastery, his relationship with Weiss, and the deeply personal story behind his newest watch.
Welcome to Weiss Wednesday with Phil Gaimon.
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For anyone who may not know your story, how would you describe what you do today and the path that brought you here?
In my 20s I was a professional cyclist. I always enjoyed storytelling from blogging to social media, eventually writing 3 books, and I was an outspoken anti-doping advocate, as the generation before mine had really done a lot of damage to the sport. All of that helped me build a fun audience and fan-base that was out of proportion to my raw race results. When I retired from racing at 30 years old, I started organizing charity cycling events, and a YouTube show called "Worst Retirement Ever," where I'm retired but I still train and set goals and punish myself up mountains. This was as the whole influencer economy began, so sponsors that I'd worked with as a racer came in to support it, and I'm on my 10th year now, where my retirement career has turned out much better than my racing career ever could have.
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tart of Mauna Kea, Waikoloa Beach, Phil's about to ruin his 40th Birthday (in Phil's own words)
You're 40! Has that milestone changed the way you think about time, ambition, or what you want to focus on next?
I turned 40 in January, "celebrating" by setting a new record on Mauna Kea in Hawaii, which is considered the hardest climb in the world for cycling (it took me almost 5 hours). As an athlete you always know when your prime years will be and I'm certainly not as strong or robust as I was at 25, but I think the real endurance isn't just being able to ride hard day in, day out when you're young and it's easy--it's being able to perform and train and work hard at 40, 50, and hopefully 90. I'll be realistic about goal-setting (I'll never touch my times from 15 years ago), but I want to be healthy and fit and perform my best the whole way through. I'm not content to peak at 28 and let myself go...I'm in for the long haul, whatever that looks like.
(Phil in July, ready for the Tour de Big Bear)
Cycling is a sport where every second can matter, but it also requires years of patience and consistency. How has that shaped your relationship with time?
I think what I learned best from cycling is patience. Training is a cycle where you built up, perform, and rest. After the rest period you start over and it's like you've never ridden a bike before so you have to trust the process: each week adding hours, adding intensity, knowing that in 6-8 weeks you'll be able to perform again. Put together years of that and you'll be a master. Now when I see someone at the top of their craft, like a Michelin chef or Cameron Weiss, it's a different thing but I know that the dedication and the humble work and the tedious solo hours are the same. My experience in cycling has allowed me to notice and appreciate excellence in general, which ultimately comes down to hours and years.
(Weiss Watch is the official timer of Whiskey Tango Fondo)
What drew you to Weiss originally, and what has your experience been wearing your current watch?
A few years into my retirement, I fell into a beef with a retired racer from the doper generation named Fabian Cancellara. He's Swiss and had a luxury watch sponsor, so I went hunting for an American watch to symbolize my rivalry and found Weiss. The first thing I noticed wearing the automatic Field Watch was that I could check the time without looking at my phone and seeing 1000 notifications, which was a game changer for my life overall.
I was never a watch guy but when you look through the window and see the inner workings and whatever's going on in there with those tiny parts, it's really incredible how perfect and precise it is, and you can see the expertise and hours of Cameron squinting through a jewelers loop with a pair of tweezers. The quality of the product and the overall atmosphere in the watch industry has a lot of parallels to cycling, where you can pay much more for a European brand, and they justify the price to extent, but for the purpose of the customer, the difference is really just marketing/brand/sponsorships, so you're paying for association with an actor or athlete or celebrity or status symbol, which is fine if that's what you want but it's not for me. Getting to meet Cameron and know the Weiss family, it feels like it has personality and soul to it. I'd also rather have a piece of furniture made by someone with a wood shop who gives a shit, versus a factory and a designer showroom and a supply chain, etc.
(Phil and wife Emily at their home in Los Angeles, with their dogs Creature and Timon)
You mentioned that your new watch feels especially connected to your dad. Can you tell us about him and why this particular watch feels like such a fitting tribute?
My dad was a computer science professor at Georgia Tech, very focused on his work and he's probably where I got my eyeroll for luxury brands and status symbols. Dad wore the same blue Levi's and brown leather Birkenstocks his whole life which I loved, but when he died he didn't really have anything physical for me to remember him by. When I saw the Titanium Weiss field watch with the denim-colored dial and brown leather strap, I knew it was the perfect item for me to wear on special occasions, that dad would have liked himself.
Short bio: Karsten Schwan was born in Germany, came to the US on a Fulbright Scholarship and earned a PhD in Computer Science from Carnegie Mellon. He taught at Georgia Tech for 25 years, and passed away of cancer at 63.
(14,000 ft high on Mauna Kea, Hawaii)
When you think about the objects you choose to keep and wear for years, what makes something meaningful enough to become part of your life?
I traveled so much and was so focused on racing, I beat up everything I touched in my 20s (I probably crashed 30 bikes) and sold whatever survived. When I retired, there were a few pairs of shoes, suitcases, and clothing items that survived the beatings and that was the first time it occurred to me to appreciate them. I'm still a t-shirt, casual kind of guy, but now I can sort of see what quality looks like, and my retired lifestyle enables me to take better care of my stuff. I'll have this watch for the rest of my life.
