Why do So Many Entrepreneurs Take up Endurance Sports?

Why do So Many Entrepreneurs Take up Endurance Sports? post image

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.

Like the TMBA? The best way to stay up to date is to subscribe.


Published on 03.21.17
  • I think the challenge-yourself-to-the-max mindset is also here in endurance sports. I’m still at the stage of learning to challenge and take on risks in business since I have been a non risk-taker all my life. But as for sports I just cannot push myself forward, let alone endurance sports, perhaps the stimulus for doing more sports is missing?

  • Stefan Dreyer

    Thanks for this article. Fully agree to your thoughts. For me one of the best takeaways of endurance sports is that I get most of my really good ideas while on the bike or similar. Even decided to quit my corporate job whilst swim training some years ago. :) I guess the consistent breathing necessary for aerobic exercise puts one into a meditative like state which in turn leads to a relaxed brain, ergo ideas. See you on Strava, Dan!

  • what’s so risky?

  • that’s interesting! I don’t think I’ve gotten one good idea out there! :D that would take me a whole other post to describe and would probably put everyone to sleep. it’s cool that it works for you though! Strava it is :)

  • Joel Runyon

    I’ll add a couple of my personal reasons:

    1) Getting out on a run for a long period of time clears my head. I solve and forget more business problems on a run than I will in a day of work. It’s meditation without being lulled into sleep by sitting in one place. When my body is moving, my brain is freed up from worrying about everything and can actually chill out.

    2) I find in business, there are a lot of things that are *outside* my control. You can work your way around them and figure out the problems, but with endurance sports, you control *almost everything* related to training. If you show up, you get results. Period. You can compete against others, but you’re always competing against yourself and can measurably see if you’re getting better or worse & what specifically happened to cause it.

    3) When I do a hard workout early in the day, it has a way of dealing with the stress that makes everything after it seem easy in comparison. I’m a more effective person & businessman when I’m working out consistently.

  • great points Joel, I hadn’t thought of #2 but that resonates with me. It’s got that quality of tinkering / workshopping / building where you end up with what you can shape from the raw material. It’s been awesome to follow your endurance efforts over the past few years (https://www.strava.com/athletes/3761441)

  • As an entrepreneur who’s training for an Ironman right now but not sure I’m ready to embrace “the lifestyle” of constant rigor and energy depletion required to go into it long term, I’ll say that for me it’s an unmistakable life accomplishment akin to climbing Everest that represents an insane effort that almost no one else in the world is willing to do. It’s a victory that I’ll have until the day I die. So that accomplishment and insanity is like catnip to a challenge-enabled person. Afterward, I’ll probably move on and try another hard thing.

    The second thing I’ve only discovered after beginning this journey and that’s community. The people who do this are generally in a similar phase of capability (at least monied and free enough to invest in the sport and travel) but also incredibly diverse otherwise. I’ve already gained friends around the world and met people who I can learn from just by training or racing together. If there’s any glue that keeps me going, that’ll be it.

  • 100% on both points, I’ve been training alone recently (fixing that in short order!) and have been realizing how much it’s been about community for me. On the first point, yep long weeks can really really run you down. I’ll probably limit my peak events to 1 or 2 going forward in order to save some energy for other stuff! :D

  • Entrepreneur life look fancy to world but in serious terms it is full of work and headache. Cycling and other sporting activities are good but to make your life leisure you need such kind of device which will make your life easy and at the same time give you tech feel . To know more about such products visit kancha.in

Next post: