Michael Capiraso

Michael Capiraso is an executive with more than two decades of experience leading large teams in the sports, entertainment, and consumer products industries. He currently serves as an advisor and board member for JoggingBuddy, a social app that helps runners compete and collaborate in dozens of countries.

Most recently, Capiraso was president and CEO of New York Road Runners, the parent organization of the New York City Marathon. His tenure saw a doubling of organizational revenue and a dramatic expansion of community programming, including the organization’s popular year-round Open Run series, the youth-focused running programs and events, as well as the NYRR Run Center. Through partnerships with New Balance and the Trust for Public Land, Capiraso’s team helped give away thousands of shoes to needy kids and built several playgrounds in underserved communities.

Previously, Capiraso led large teams at Calvin Klein, WPP Prism, Cole Haan, the National Football League, and Major League Baseball. He lives in the New York City area and has run 28 consecutive NYC marathons.

What does your typical day look like and how do you make it productive?

I get up early. Usually I go running, or do some other fitness activity. That helps get my body and mind going, clears my head, and sets the stage for a productive day. I have some of my best ideas on my morning run.

Then I have breakfast and start on the day’s agenda. Often, it’s a combination of meetings, site visits, and self-directed work.

How do you bring ideas to life?

Physical activity is really helpful to generate and clarify ideas. I do a lot of socializing of ideas where I talk through ideas with people and get feedback.

If there’s an idea I’m really excited about, I may take it and run with it rather than waiting for extensive feedback. But I really do value others’ input.

What’s one trend that excites you?

Digital connection. It’s not just social media anymore — it’s digital exercise and activity apps and so much more. You can connect with people who share your interests, on your terms, no matter where they are in the world.

What is one habit of yours that makes you more productive as an entrepreneur?

I’m relentless. I stay motivated, inspire others to follow me, and stick with something until it gets done.

I also love to listen and ask questions. Early in a potential project, this helps me understand whether an idea really is worth pursuing, and how best to pursue it.

What advice would you give your younger self?

Take more risks. I mostly took the safe path earlier in life, and while it worked out fine for me, I now see the merits in taking more chances. It’s really important to listen to your gut.

Tell us something that’s true that almost nobody agrees with you on.

That I can change my mind. It’s important to be relentless and take ownership of your projects, but you also need to see things from a different point of view and know when to make changes. You have to have a growth mindset.

As an entrepreneur, what is the one thing you do over and over and recommend everyone else do?

I’ve exercised my entire adult life. It’s so important, whether walking, running, or a directed workout. Your overall health improves when you physically engage your body, and it helps gather your thoughts too. But how you choose to exercise is up to you.

What is one strategy that has helped you grow your business?

Socializing has been really helpful to my career. Not just networking for the sake of it, but really getting out there and gathering information from people in social settings. This has been a great help for my strategic thinking and for some of the biggest wins of my career as well.

What is one failure you had as an entrepreneur, and how did you overcome it?

I once took an opportunity — which shall remain nameless — that I initially felt excited about but quickly realized wasn’t for me.

It was a disappointment because I believe you should be passionate about your career choices. But the experience turned out to be a blessing because it helped me redirect my focus back toward the opportunities I was more passionate about — sports, entertainment, consumer brands. It’s important for me to be connected to people and this mistake showed me how to do that.

What is the best $100 you recently spent? What and why?

I recently purchased the Calm app. It has really helped me to be more mindful and put me in a better headspace overall to help with my mental health.

What is one piece of software or a web service that helps you be productive?

I have to plug the Calm app again. It’s now a really important part of my health and creative process.

What is the one book that you recommend our community should read and why?

“Tools of Titans,” by Tim Ferriss. It’s a great read that shows you how really successful leaders view the world and lets you in on their biggest successes (and failures). I’d recommend it to anyone who aspires to leadership.

What is your favorite quote?

“It is never wrong to do the right thing.” Mark Twain

Key Learnings:

• Physical activity is really helpful to generate and clarify ideas.
• Digital connection is not just social media. It’s digital exercise and activity apps and so much more. You can connect with people who share your interests, on your terms, no matter where they are in the world.
• It’s important to be relentless and take ownership of your projects, but you also need to see things from a different point of view and know when to make changes. You have to have a growth mindset.