Why do So Many Entrepreneurs Take up Endurance Sports?

This past weekend I packed up my bicycle and flew to Terracina, Italy.

It’s a beach town just over 100km (62 miles) outside of Rome. Here’s what it looks like:


Not bad!

When I got there, I rode my bike around and drank all the coffee.


But I wasn’t there to see the sights (although, it’s amazing how much you can see of a place on a bike).

I was there to race. And, since I was all alone and not many people in Terracina speak English, I had a lot of time to think.

One thing I kept coming back to: why do so many entrepreneurs gravitate towards endurance sports? (And insane endurance challenges like the India Pacific Wheel Race, or Ironman Triathalons).

Perhaps I was questioning what the heck I was doing there.

On paper my purpose was clear: finish GFNY Italia — a 125KM bike race — as fast as I possibly could.

It was only a few years ago that I thought endurance sports, and goals like that, seemed pretty boring. I’ve been guilty of rolling my eyes a few times when yet another colleague would announce, “I’m going to run a marathon!”

But now I’m one of them.

I wanted a personal challenge. I wanted to see (and feel) my maximum potential. And, aside from a few changes I would make in retrospect, I did that.

I would have been pretty disappointed if I hadn’t. Because for 12 weeks, just about everyday, I’ve been training for this event. That’s 3 months of eating different foods, juggling work and travel schedules, new bikes, new clothes, travel arrangements, and daily instructions and feedback from my coach. I even organized a training camp in Thailand to do base training.


And, unlike skill-based sports, a lot of that fitness I’ve gained will be fleeting. Many say you can only be your fastest for a month or two out of the year (in training jargon, “peaking”). Spend a few weeks off of your bike, and the results of your hard work will start to fade away, requiring weeks of structured training to regain fitness.

So, why do so many motivated entrepreneurs take up endurance sports? Here are some things that I’ve learned about endurance sports over the past few years that might qualify.


The one I now appreciate the most is this:

As someone in middle-age, you can dedicate a significant amount of time to training and competing without suffering serious injuries.

My average training weeks were well over 10 hours, and that doesn’t include ancillary activities like eating, stretching, prepping my bikes etc.

A few years back, I got back into working out and playing basketball three times a week. But I found that it was tough to stay on the court consistently. A constant string of injuries kept me questioning my sport of choice.

If I keep cycling (and I have no idea that I will!), I will by most people’s estimates be significantly better in 10 years than I am today. For those of us over 30, how many sports can you say that of?

And that amount of time and dedication can create narratives in an athlete’s life that I think appeal to those who are goal-oriented. If you define your priority race in June, for example, you can start to work backwards. What do you need to be doing in April to reach your goals?


Other benefits of endurance sports:

  • Well defined amateur competition infrastructure.
  • And that competition infrastructure ‘travels well’. It’s easy to combine travel and competition.
  • On that note, getting to see Terracina, Italy from the perspective of a bike was fantastic.
  • You can compete with others of differing skill levels without ruining the competition (so participating in endurance sports with friends or partners of differing fitness isn’t an inconvenience, whereas in team sports that wouldn’t be so much fun).
  • Skill isn’t nearly as important as work ethic. Endurance sports are all about, well, endurance, and therefore favor those with (in this order) 1) good work ethics and 2) good genetics. Skill doesn’t really come into it as much. This makes endurance sports pretty inclusive and tailored for those who’ve spent years developing their work-ethic (sounds like an entrepreneur).
  • “Chasing flow.” This is  an undeniable feeling that Patrick Brady described so eloquently in our interview with him. His claim is that a bicycle is one of the most healthy and sustainable ways to reach an engaged “flow state.” That’s one way to describe it. I have a hard time describing what it felt like to give it my all in the Italian mountains with others who had prepared similarly – but I know that I’m willing to put in another 12 weeks to have it back again.

All that and there’s still part of me that thinks all this training is nuts. It might not even be healthy. But I have another race in June and, as it stands, I’ll start back tomorrow.

Are you an endurance athlete? Would love to hear what attracts you to your sport.

If you’re curious about endurance sports, here are some good places to start:



PS, One of my favorite writers Cal Newport is on the podcast this week! Be sure to check out that episode.

PPS, for fellow cyclists here’s the ride profile.

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