Last week I went to Seattle for the holiday party at the Allen Institute for AI Incubator. They had a talent show, so I took the chance to sow chaos among a crowd of maybe 70 AI entrepreneurs and investors. I made them chant, “Do a kickflip, do a kickflip”, while I risked life and limb. Fortunately, I landed the kickflip. Unfortunately (and rightfully) I lost the talent show to the Yoodli team who did an amazing Bollywood skit.
After the talent show, I found myself in a series of conversations about surfing. One of the managing directors was like, there’s probably some good entrepreneurial lessons in surfing. And I was like, yeah about that…I’ve been sitting on a blog post about it for several weeks. So here goes.
Go big, but maybe be prepared for it
I started surfing in high school and got pretty obsessed. I was at the beach almost every day for a few years. And the thing about south Florida is that the waves are, let’s just say…mostly crappy. So you learn to surf anything. Anything from breaking fins on the sand in one foot shorebreak to massive choppy hurricane surf. But the dream was always to surf big, pristine waves in exotic places like Indonesia and Hawaii.
One day in my mid-20s, Kim surprised me with my first big surf trip to the North Shore of Oahu. For the uninitiated, this is the mecca of surfing. And it was mid-December, when the surf can get scary big.
We arrived to the North Shore and got to our hostel late, where we met two Australian guys drinking in the common area. I went to asleep immediately. But just a few hours later, I woke up to the thunderous sound of waves breaking across the street. I felt like the ground was shaking and honestly was a little intimidated. But the Aussies had stayed up all night drinking and were heading out to surf at 5am. I remember thinking, these guys are totally nuts.
So we decided ok, let’s just go see what the surf looks like at Waimea Bay - a famous big wave surf spot and a tourist attraction. After watching the surf at Waimea for about ten minutes, I thought to myself yeah I could probably do that. So I paddled out on a 7 foot shortboard (to me that was really big). When I got close to the lineup, there were lifeguards on jetskis and it seemed like they were looking at me kind of funny. Then I noticed literally everyone is on a ~10 foot gun - boards made for big wave surfing.
When the first set wave came in, it was probably 25 feet. I remember paddling over the top, nearly vertical as it was about to break and thinking is this how I die. Well, I didn’t die and paddled to shore, past the back-breaking shorebreak of Waimea. When I got to the beach I thought, well that was stupid.
Slightly less terrifying
The next day, we went to Sunset Beach. It was the day before the Vans Triple Crown, the biggest tournament in pro surfing. As I was paddling out I recognized a couple famous pro surfers getting ready for the competition the next day. Fairly intimidating, but I figured I know what I’m doing and am in good paddle shape. So this time I decided I’m taking a wave no matter what.
Waves were probably double overhead, which is pretty big but manageable. So I paddled for a wave, dropped in, did a turn, and I’m stoked. But then I realized, wait I’m stuck on the inside during a massive set of waves, paddling over razor sharp reef. I was just getting tossed around trying to not get hammered into the reef - which I did and got a nasty reef rash on my back.
So I figure, one wave, I’m good. I start paddling in, trying to get away from the impact zone. But the thing is, I don’t know anything about Sunset Beach and that there’s basically a river that I have to fight to get back in. After about ten minutes, I realize I’m not going anywhere. It took me 45 minutes of straight paddling to make it back to the beach, where I fell down in exhaustion. Later, I learned that the lifeguard asked Kim whether he should come save me.
You’d think that would be enough for. Just enjoy the time in Hawaii now, right? NO! The next day we went to a different spot and I had one of the best surf sessions of my life.
Definitely less terrifying, but a broken neck
Last story, I promise. Fast forward a dozen years. It’s 2020, during the peak of the pandemic. I’m working at Illumina and getting ready to present this big project in front of a global audience. The presentation was mid-morning and the night before, I look at the surf forecast. It’s small, but I decide I just need to blow off some steam before my presentation. So I wake up around 5:30am and grab by kids’ soft-top Costco Wavestorm without a leash. I’m clearly not taking it seriously.
I’m in the water at 6am, basically by myself at my local beach break. I take my first wave and it’s teeny-tiny. When I get to the end of the wave, I surface dive off my board and don’t realize I’m only in about 2 feet of water. My head hits the reef. I stand up and I’m dazed. Then I notice a weird pin prick in the tips of both thumbs.
I was always good at neuroanatomy so I immediately realize this is spinal cord damage, probably around C3-C4. I’ve got a broken neck. Somehow I stumbled back to my car, went into shock, got misdiagnosed by overworked doctors during the height of the pandemic, and laid in bed for two months staring at the ceiling. No idea whether I’d be able to hold my kids again, let alone surf.
Long story long……I feel lucky to be alive after a fairly miraculous healing. Three months to the day after the injury, I took my kids to the same surf spot and pushed them into waves. Four months later, I was surfing again regularly.
Some lessons I’ve learned from surfing
I tell these stories not to brag (they’re honestly a bit embarrassing), but to illustrate a few things I’ve been thinking about.
Lesson 1 - go big. You’re going to expend just as much effort catching a small crappy wave as you are a beautiful overhead wave. And while there’s risk in both, the risk isn’t necessarily proportional to ambition. I’ve never broken my neck in big surf haha. Same thing with a business. You might as well do something big that you’re stoked about. It drives you to paddle harder when you’re inspired and you know there’s a mammoth coming at you.
Lesson 2 - know your limits. You can’t go hard all the time. Slow down and check the conditions. Don’t just jump into the water right away during a massive swell. January this year, there was a 20 foot swell that hit San Diego. You better believe I was careful. It took me 4 hours to figure out where I was going to surf that day. In startups, it helps to have learned tough lessons in the past and select the problems you’re going to work on using personal experience and many many customer conversations.
Lesson 3 - make dynamic decisions. Nothing is set in stone. Build frameworks in your head from years of accumulated experience and use that to make the best decision in the moment. Sometimes I’m gunning for a wave and it feels right so I dig deep. Other times, I notice last second that it’s going to close out so I back out. In startups, decisions come at you quick and if you don’t move quick, you’re dead in the water. Trust in your accumulated wisdom and aim for 80/20 (80% of the time I’m right, all the time). But spend the needed time on critical decisions that can’t be reversed.
Lesson 4 - don’t give up. Sometimes you get caught on the inside and feel like you’re in a washing machine. Other times you drop into a wave, slip, and embarrass yourself in front of friends. Every once in a while, you get hurt. But as much as anything, surfing is about pushing yourself past your comfort level and doing things that scare you. To me, life is about facing your fears and learning from your mistakes.
Well, I could probably go on an on about this. Maybe another time. Happy holidays to everyone! See you in the new year.