1×10: Jake Szymanksi, Leave It On the Road

Welcome to 1×10, where we ask 1 inspiring human 10 questions about how they are using cycling as a force for good. Read on to meet Jake Szymanksi, cyclist, photographer, producer, and advocate extraordinaire for Leave It On the Road, a nonprofit raising funds for to fight cancer, through cycling events. And in his day job he’s a brand marketing manager at Google. Learn more about his favorite bike, his most memorable ride, and how he’s using bikes to help fight cancer and more, in his 1×10 interview.

1. How / why did you fall in love with cycling?

After riding and racing for a handful of years, I really fell in love with cycling after moving from Minneapolis, MN to Portland, OR. Living in Portland and the people there introduced me to a whole new style of riding. I discovered the depths of long, remote rides, inclement weather, and the camaraderie formed through those often adverse conditions. 

One of the close friends I made during that time was Michael Tabtabai, who originally founded Leave It On The Road [insta]. We met in 2013 as he was training for his ride across the USA. In 2015, he invited me and a couple friends to join him on an epic 8 day, 800 mile ride from Portland to San Francisco that would become the first of Leave It On The Road as people know it today. 

It was really intimidating to me at the time. I’d never done anything like that before and wasn’t sure if I could. In the middle of a climb split from the group on the fourth 100 mile day in a row, I lost myself completely to the rhythm of pedaling a steep uphill through the Redwoods, muscles aching from the previous days mileage. It was like my 10,000th hour of riding or something (not really)—I reached a crazy endorphin high like I’d never felt before. That was when I knew I really loved cycling and I’d forever be chasing that feeling.

2. Favorite Bike (that you own or covet)?

At the moment, my favorite bike to ride is my Specialized S-Works Diverge. It’s short wheelbase and low bottom bracket are the perfect blend of fast and playful. Living in San Francisco, we have access to an immense amount of exciting dirt trails around Mt. Tamalpais that are perfect for this kind of bike. 

My all-time favorite bike is my Speedvagen Rugged Road, “Prototype 2” as I like to call it. For a few years, I worked closely with Sacha White and the team at Speedvagen on various freelance projects. During that time, I also worked with them to push the Rugged Road design from their first prototype to incorporate bigger tire clearance, thru axles, flat mount disc brakes, and more. They built my bike as the second prototype, incorporating most of the design updates that would launch as the final bike for customers to buy. I love this bike. It’s custom built for my body and has done thousands of miles with me. It slices through corners like a samurai’s katana and I wouldn’t trade it for anything. 

3. What’s the most memorable ride you’ve done, and what happened?

An early ride I was invited to join in Portland really opened my eyes to the adventurous nature of cycling and I’ll never forget it. This was around the time the Rapha Continental were becoming a thing—and eventually a big inspiration for me. At that time, I knew very few people in Portland and when I got an invite to join a ride, I’d jump at the chance without knowing exactly what I was getting into. I showed up to the coffee shop and a friend Patrick (@ultratradition) who had invited me was there saying to everyone, “Guess what gang!? We’re gonna get into the shit today!” He was referring to some remote gravel roads out northwest of Portland that people were just starting to explore on bikes. 

The year was 2012 and no one really had disc brakes at that point. We were all still riding 23 or 25c rim brake road bikes. Some guys rode with frame pumps and multiple tube patches, but that was the best we had. Tubeless gravel tires and all of today’s tech didn’t exist yet.  

So, we pedaled out into the maze of logging roads outside of Portland in search of what Patrick affectionately called “The Northwest Passage” as if it was some sort of secret silk trade route. In fact, it was a breakthrough of a bridge that connected to disparate gravel roads into a full loop, about an 83 mile round trip from the city. You had to pedal uphill for what seemed like forever, passing multiple gated side roads until you identified and hopped the right side-road gate. This lead to the rocky jeep trail that is The Northwest Passage, then spilling you out onto another gravel road that pointed towards home. For me, the first time doing this blew my mind. I was way short on food and fitness, bonking a bit on the way home, but I made it. I wanted more.

We later did this route again a number of times with our less than capable bikes, each time enduring a handful of pinch flats. A small price to pay for the excitement we’d discovered! We made up other various gravel loops and named them things like “The Peacocks”, which is another story. 

This was the gate to The Northwest Passage

4. Who do you admire in the cycling world?

You’ll meet many wonderful people through cycling, but few who seem to be able to effortlessly balance peak fitness with an incredible attitude riding socially. They seemingly ride unfazed by inclement weather, fatigue, or any other cause for discomfort. They ride through all conditions with panache, interesting conversation, and admirable strength. This kind of balance and the people who embody this spirit are the people I admire in cycling.

5. Top tip for a new rider, or a cyclist about to take on a new challenge?

Riding more often is more important than riding longer. Stay dedicated and ride often, but listen to your body and rest. It’s easy to overtrain thinking you need to do more and more and more to be prepared (I’ve been there many times). Just remember that resting after riding is what makes you stronger 🙂 

Photo by Natalie Starr

6. Favorite trend or innovation in cycling?

At the moment—Cargo Bibs. Even with jerseys. Everything’s just more convenient with pockets on the sides of shorts!

7. What are you doing to use cycling as a force for good?

My friends and I use our vacation time riding bikes together to raise money for charity. We call it Leave It On The Road. We do epic rides with the goal of helping to one day end cancer. Most of us work in the creative industry and use our skills like photography, design, and writing to produce content that inspires people and works as a vehicle for keeping momentum in the fight to end cancer. All riders pay for their own flights, hotels, meals, etc. and all proceeds we raise throughout the year are donated directly to our chosen charity. We tell the story of each ride through our Instagram and sell products like stem caps, water bottles, and jerseys on our website to raise money. In 2018, we became an official 501c3 non-profit, which has been a big step for us. Since then, we’ve been focusing on funding the most cutting edge research that has the chance to be the root solution to cures for all kinds of cancer: Gene Therapy through the Alliance for Cancer Gene Therapy

Photo by Natalie Starr

8. Thinking about the work you’re doing, what do you see as the potential change for people or the planet? If you are successful, what impact will you have?

A cure, not just for cancer, but hopefully many other illnesses that can be reversed with genetic techniques. 

9. What’s your biggest challenge/obstacle to success?

Time. There are so many things happening in life that it’s always hard to dedicate as much time and effort as I’d like to planning, preparing, amplifying Leave It On The Road’s fundraising efforts. 

Photo by Natalie Starr

10. How can people help? Where can they learn more about your work?

Plan a ride and share it with us! We’re interested in helping other people organize their own fundraising rides and promoting them through Leave It On The Road. Visit www.leaveitontheroad.com to learn more, and shoot us an email if you’re interested. jake@leaveitontheroad.com 

Jake Szymanski is a cyclist, photographer, and fundraiser and advocate for cancer research through Leave It On the Road. During the day he’s a brand marketing manager for Google. When he’s not doing the aforementioned you can find him cruising the dirt around the San Francisco Bay area.

Edited by John Kim. When he’s not out for a ride, John uses his expertise in Corporate Social Responsibility to help companies do well by doing good. Find him at virtcyc@gmail.com or VirtCyc on twitter or instagram.

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