How My Cycling Obsession Makes Me A Better Entrepreneur

PayPal cofounder Max Levchin talks about how he makes time for an intense hobby with a super-busy schedule. (Hint: He wakes up really early.)

How My Cycling Obsession Makes Me A Better Entrepreneur
[Photo:josealbafotos via Pixabay]

To say that Max Levchin has a busy schedule would be an understatement. Best known for being a cofounder and former CTO of PayPal, he went on to become a board member and investor in Yelp and Evernote after PayPal’s sale to eBay in 2002. (PayPal and eBay eventually split in 2014.)


In 2012, he cofounded Affirm, the consumer finance company where he holds the title of CEO today. He also sits on the board of Glow, a fertility tracking app that he founded out of of his own data-driven investment lab, HFV Labs.

Related: Unfinished Business–Max Levchin’s Quest To Build The Next PayPal 

But despite Levchin’s intense schedule, there is one activity that he religiously does every single day–riding his bike. Fast Company recently caught up with Levchin to find out more about how his cycling obsession makes him a better entrepreneur, and why he finds it easier to train hard when he has a lot on his plate.

Morning Routine

I always get up between 4:30 a.m. and 5:30 a.m., depending on when I actually get to bed, and how much time I have before my first meeting. I typically work for an hour after I wake up, deal with whatever has happened overnight, and figure out what’s happening that week.

Within an hour, I’m on the bike. Depending on the weather, time of year, sunrise time, I go outside–across the Golden Gate Bridge, and past the hills of the Marin Headlands. But if it’s too cold or too rainy, I have a bike trainer set up and I can hop on it indoors–same bike, same geometry, same everything. 


I do this every single day. On very rare exceptions, if I have a really late night and require more sleep, I might change my schedule and work out in the afternoon.  

Max Levchin [Photo: courtesy of Max Levchin]

Cycling And Entrepreneurship

There’s a lot of reasons why I love road cycling. On the physical side, it’s one of the few sports where the learning curve is inverted. A lot of times you pick up a sport and it’s just a struggle. You have to persevere to eventually become good enough. With cycling it’s the other way around. You start and you improve so rapidly.

There’s also a lot of parallels between cycling and entrepreneurship. It’s an endurance sport, you pretty much have to condition yourself to put up with a certain amount of pain with the knowledge that you can quit, if you’re too cold or too hungry or whatever. The only way you finish the ride is if you decide that it doesn’t really matter that it hurts, you just have to get through it.

This whole notion of riding through the pain has great parallels with entrepreneurship where there’s always a low point. If you weren’t really committed, you would quit. But if there is a commitment to the cause, an idea that drives you, that propels you to continue.

A Forced Break

When I’m on my bike, it’s a fairly long period of time where I’m forced not to think about work. In my case, that’s actually a hard thing to do. Even if I have some kind of work crisis, I just get on my bike first thing in the morning, and for at least 90 minutes, I don’t spend much time thinking, which is good, because by the time I get to the office, I have a fresh point of view.

[Photo: courtesy of Max Levchin]

Rigid Schedule and Compartmentalization

I tend to be more organized the busier I am, and I think that’s true for a lot of other people. I think if you have lots of freedom to say, “Well, I’ll work out hard tomorrow, today’s going to be an easy day,” you actually spend a lot of days not working out very hard at all.

I have a lot of friends who’ll say, I’m going to skip the gym today because I trained hard yesterday, and then they end up skipping it for two days. I think it’s a lot easier to maintain a consistently intense schedule, as opposed to occasionally do bursty workouts that might or might not happen the next day.

I don’t find it that difficult to balance my cycling and my work, because the more intense my work gets, the more regimented everything becomes for me. When the intensity of my work is very high, I know I can’t spend more than x hours or x minutes on a specific task, or something else will fall behind.

Similarly, I have no room to decide whether I need an extra 15 minutes of sleep and hit the snooze button. If I’m not up at the right time, I will miss a few minutes on my bike. Some people have trouble following rigid schedules, but I don’t.

Cycling As A Networking Activity

I think that going for a group ride creates a great sense of camaraderie and brings a whole new level of intensity in relationships. I think this is true for any sport–you get a quick picture of what happens to this person when they’re put under pressure. You get a truer version of someone when they’re on a bike next to you, and that creates authenticity. It’s a very powerful thing when you’re trying to get to know someone.



About the author

Anisa is a freelance writer and editor who covers the intersection of work and life, personal development, money, and entrepreneurship. Previously, she was the assistant editor for Fast Company's Work Life section and the co-host of Secrets Of The Most Productive people podcast.