Michael Capiraso — JoggingBuddy Advisor

Michael Capiraso
8 min readJan 22, 2021


Michael Capiraso is a visionary, transformational leader whose results-driven focus and holistic team-building have delivered sustainable growth across sports, entertainment, and consumer goods brands. A dynamic and strategic executive, Michael led large-scale operational and brand building efforts at the NFL, Major League Baseball, Calvin Klein, Cole Haan, and WPP before ascending to his role as President & CEO of New York Road Runners (NYRR), organizers of the TCS NYC Marathon.

Throughout his career, Michael has delivered impressive results through organic growth, acquisition and innovative marketing and technology, enhancing culture with forward-thinking programs and driving results via highly collaborative and diverse leadership teams.

During Michael’s tenure at NYRR, the organization’s annual revenue nearly doubled to over $100,000,000; the number of participants in NYRR events, youth and community programming doubled to approximately 700,000; Michael was integral in establishing multi-year partnerships with TCS and New Balance; he developed the partnership with Trust for Public Land in NYC building playgrounds in schools in underserved communities; he opened the NYRR’s Run Center; he planned and implemented NYRR’s profitable virtual racing platform; and he played a vital role in the renovations of the office and warehouse to upgrade NYRR’s facilities to the state they are in today.

As President & CEO as well as Board member, he built a high-performing team and drove the professionalization of NYRR staff and operations resulting in the expansion and diversification of revenue streams. He initiated a comprehensive strategy and planning division and delivered expense reductions and company-wide efficiencies to offset significant infrastructure expensive increases. Under Michael’s leadership, NYRR solidified its position as the world’s largest Marathon and America’s premier participatory sports organization, with the highest revenue, membership and industry accolades. Michael established a mission-driven vision for the organization, focused on serving the running community. Michael embodies that mission himself, participating in 28 consecutive New York City Marathons while raising more than $100,000 for NYRR’s Team for Kids.

Before joining NYRR, Michael led marketing, strategy, digital, creative and brand development efforts for Cole Haan as the company’s Chief Marketing Officer. Michael and his team developed a five-year multi-channel growth plan to double revenue that built upon synergies with Cole Haan’s parent company Nike and a robust crowdsourced community engagement effort, including the brand’s first-ever social media marketing campaign.

Prior to the Cole Haan, Michael was the North American CEO of WPP’s Prism, a strategic marketing agency (clients included AT&T, Coca Cola and the PGA), Vice President of Marketing and Executive Creative Director of the National Football League (under both Commissioners Tagliabue and Goodell). He was responsible for the NFL’s 360-degree brand strategy and creative efforts while overseeing a comprehensive rebranding, driving $330 million in sponsor activation revenue for Super Bowl XL.

He also held leadership positions at Major League Baseball, and Calvin Klein, where he worked directly with Mr. Klein on groundbreaking advertising campaigns and product launches.

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

A typical day is often getting up early. When the weather is good or sometimes even when it’s not, I go running in the morning. I find that going for a run is one of the things that gets my mind going, and helps me to be more productive throughout the day. Running clears my head in some ways, but also generates a lot of great ideas and creativity. A healthy breakfast is also important. And then it’s off to whatever the day brings or is needed, whether it’s meetings, whether it’s meeting someone else for a run, whether it was attending a school visit, or meeting with a partner. But I usually start the day with a good, healthy bit of exercise and a good meal.

How do you bring ideas to life?

.Exercising or really any type of physical activity helps me come up with new ideas, bringing them to light depends on the idea. I do a lot of socializing. I like to talk to people about ideas. I like to get some feedback. Talking gives me an opportunity to think through the ideas, and see what others think of them. And if there’s something I’m really excited about, I’ll try to just move it forward quickly by gently nudging things along. But really it depends on the idea. Socializing and talking ideas through with others is definitely always an important part of the process.

What’s one trend that excites you?

The way that we are all connected digitally continues to excite me. I know that makes most people think of social media, but there’s so many digital platforms, like exercise and other activity apps to connect people. I love how you could be connected with people all over the world, who have common interests and are sharing related content. So I’m very excited about digital platforms and their potential for the future, and how they have already have brought communities together.

I think of the world as a global community now, and you could be as connected to someone in Austin, Texas, or Italy or India, as you are in New York City.

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

I would say being relentless. Whenever you want to get something done or get that urge to move an idea forward, you have to kind of be relentless.

That means staying highly motivated, and driven to stick with a project and commit the necessary level of effort to try to move those ideas forward.

But one of the other things that actually makes me productive is that I love to listen.

Asking questions is really important. Try to be as analytic as possible, especially in the beginning when you’re just starting to put your ideas together. Asking questions and listening really makes me productive because it helps me get input and early feedback on those ideas. So in addition to being relentless and really driving forward, sometimes the most important thing you can do is just ask questions and listen.

What advice would you give your younger self?

I would tell my younger self to take more chances, to be more of a risk taker. I think one of the things that we do as we’re growing up is sometimes we have a tendency to take the safe path. But now, further along in my career, I think that risk taking has it’s merits.

Being an analytic has value, and I like to have information and data, but your gut instinct sometimes is the thing that really can take you to the next level. So don’t be afraid to take chances when those opportunities arise.

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

Oh, gosh, that’s a tough one. That I can that I can change my mind.

As I’ve said before one of the most important aspects of bringing new ideas to life is being relentless, but I also talked about listening, and I think that one of the things that I really pride myself on is trying to be open minded, have a growth mindset. That means being able to change my mind or to see things from a different point of view. Having a growth mindset can be key to the success of any given idea.

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

One of the things I think I’ve done for the longest time is a form of exercise. I think exercise, regardless of what it is, whether it’s walking or running, or taking a class is so important. Physically getting your body engaged in movement is so vital, because I think the movement helps overall with your mind, your mental health, and gathering your thoughts. So I would say exercise of some form, movement is really critically important for people. However it comes to you depends on the person, but it’s an important part of being successful every day.

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

Socializing has been a good strategic thing for me. Socializing ideas and initiatives, getting information. I’m someone who loves to gather information. I feel like I have great capacity to be able to take in lots of bits of information, opinions and thoughts and they help me to make good decisions. Information gathering has really been helpful in strategic thinking, and has really helped me move my career forward.

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

Without naming the position, I once took an opportunity that I wasn’t as excited about as I initially felt I would be. I’m someone who believes a lot in being very passionate about the career choices you’re making. And, the way that I overcame it was to kind of redirect my career back towards sports, entertainment and consumer brands because that was more in line with what I love to do. Being connected to people is an important part of my daily work life. So I think I took a wrong turn at one point and managed to turn it around and get back on track by refocusing on my career goals.

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

I recently purchased the Calm app, to help with meditation & mindfulness, and I thought that that was money well spent. I really believe that all of us need to make sure that we’re taking time to set aside to give thought to mindfulness. So I will say that that was a good investment.

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

Going back to the last question, I would have to say the Calm app. Meditation has become an important part of my process, and clearing your mind is invaluable when it comes to developing new ideas, and bringing those ideas to life.

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

Tools of Titans by Tim Ferriss is a great read because it’s a compilation of ideas from some of the best of the best. The book covers a lot of people who’ve had success and failure in their careers, and it asks them a question or poses to them a situation, and it presents the perfect opportunity for them to provide insights and feedback. So what you get in this one book that makes it so interesting is the different perspectives of thought leaders. You combine people who have had a lot of success launching their ideas and startups. But then you also get the perspectives of people who had challenges. And you get snippets from all of them in one book.

What is your favorite quote?

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

Key Learnings:

  • Don’t underestimate the effect physical activity can have on a healthy brain. Being physically healthy always helps with your mental capabilities.
  • Socializing is one of the best ways to connect with other people, and really test your ideas before executing on any plan.
  • Be moveable. If you can’t change your mind about something, you can’t adapt and overcome the challenges that are going to inevitably come your way.

Originally published at https://ideamensch.com on January 22, 2021.



Michael Capiraso

Michael Capariso is a visionary leader who serves on the board of JoggingBuddy and has shaped the business and brand strategies of the NFL, MLB, NYRR and more.