7 Ways Building a Startup is Like Running an Ironman

I wrote, ‘Building a Startup is Like Running an Ironman,’ in 2014 when it was originally published in AlleyWatch and the Dave Partners site. Now I’m training for my third Ironman triathlon and I can’t help but reflect on the life and leadership lessons that the rigor and discipline of athletic competition can teach us.

Champions from all walks of life make their home in NYC. Ex-pats formerly from the East Coast now living in the Bay area are flocking back home to NYC where exciting new startup opportunities exist like never before. More than 8 million passionate New Yorkers, many of them knowledge workers, are, in their own way, building NYC into a thriving metropolis of digital innovation.

The Ironman US Championship race is being held in the greatest city in the universe this year, and it sold out in less than 11 minutes!

With the inaugural NYC Ironman drawing nearer, I had a thought and drew some parallels between competing in an Ironman and building a startup:

Decide and Commit First, Then Figure Out the Plan

You may not have a bicycle, you may not know any VC investors; maybe the last time you swam was to a tiki bar. Maybe you thought it was necessary to be sponsored by an incubator or have an MBA — this is not true. Here IS the truth: 100% of everything you will ever need in life to be successful is already inside you. Decide what you want in life. Make the emotional commitment with a burning desire to achieve its fulfillment, and then figure out a massive action plan to achieve it!

Beliefs & Success are Directly Correlated

Henry Ford said, “If you think you can or think you cannot, you are correct.” There is scientific evidence that the ‘central governor’ in your brain is wired to protect itself by preemptively shutting down your muscles before any part of your body reaches total failure. In other words, your brain quits before your muscles actually fail. The good news is that as humans we have ultimate control over our thoughts, and we can override this brain function. There’s an entire field of study around neuro-associative conditioning that suggests the brain, when programmed adeptly, can turn normal humans into ultra-endurance athletes and entrepreneurs. Further, the human capacity for astonishing acts has been documented by ordinary people doing extraordinary things. Like the mother who is forced to lift a car to save her baby, the iron will and determination necessary for grand accomplishments can also begin with a simple momentary suspension of disbelief. Exercise your “must-do” muscles and they will get stronger every day!


The great achievements of humanity have often started with one person’s desire to serve the greater good, to serve something bigger than one’s self. Maybe it’s your spouse, maybe it’s your kids. Perhaps it’s your community or all of the people in the world who have yet to benefit from your startup’s promise. Whatever the purpose, keep it close to you and top of mind. Most importantly, hold yourself accountable to the actualization of the good you will bring to the people who need you most!

You Need a Team and a Coach

All of the great athletes, professionals and top performers work with a coach. Especially in business when venturing to disrupt existing industries or markets, it’s essential to execute a strong game plan and get the best out of your team. Building trust, overcoming adversity, sparking the necessary emotional commitment, designing & executing the right game plan and driving results can all be done more effectively when your team performs together at a high level. As a high-performance entrepreneur or leader, you’ll want a strong executive coach, bike mechanic and support crew to point out the blind spots and help you stay on plan. The first 75 people, like the first 75 miles, are the most difficult. A strong team and a courageous coach will help you build the best foundation for the long haul.

Failure, Learning, Discovery & Determination

Endeavors like competing in an Ironman or building your own startup will knock you down and sometimes hard. There will be obstacles and there will be naysayers. There will be people who are so afraid of failure that they will try to discourage you from even getting started. There will be people who might fear your success for the desperation they would feel being left behind. You will try new exercises. You will create new programs. You will stumble and fall. Some of your failures will be public and you will be humbled. And after the chaos, in the quiet moment of your next decision, you will glean a new learning. You’ll get back up and have discovered how to do that thing differently, better. You will attack with more vigor. You’ll repeat the same exercise and this time with more certainty, with more courage. And the hardship you overcame is now a barrier for someone else. Your determination will make you better, faster, stronger. You will choose to be defined not by how you stumbled, but rather by how you got back up!

Goal Setting, Discipline, Performance Metrics & Achievement

Peter Drucker said “what gets measured gets managed.” We need goals in life, big and small, to move forward. Measuring & training in specific heart rate zones is the fastest way to athletically increase your VO2 max and lactate threshold. Both in business and athletics, being data-driven in your goals and execution is the best way to measure your progress and increase performance. The most successful entrepreneurs and athletes are masterful at setting and achieving performance metrics.

Gratitude, Fulfillment & Smiling

Gratitude in our hearts to enjoy the journey, the scenery, the workings & wonderment of the universe makes it all worthwhile. Get to know fellow entrepreneurs, learn together, encourage each other. On the eve of Ironman Canada, Sister Madonna Buder offered some great advice: “Pain is inevitable, suffering is an option. Whenever you hit an emotional low point make sure you smile. The harder you hit a low point, the harder you should smile.” At mile 15 of the IM Canada marathon, I discovered the human physiological effect of smiling that Sister Madonna spoke about just days earlier when my runner’s knee re-emerged after years of silence. It only takes 17 muscles in the face to smile vs 43 to frown or have agony on your face. Further, the muscles in the face are connected to the brain in a way that affects endorphins and serotonin — the natural pain killers and feel good hormones. Externally, smiles are contagious and people want to support you more. Spectating crowds would literally single me out from the mass of runners to cheer me on because I was smiling!

As the countdown to my next Ironman approaches, I find myself humbled by the stories of ‘triumph over adversity’ from fellow Ironman triathletes and their determination to ensure that their light shines bright. We’re all connected on this planet by the human experience, and the hardships we all face play some part in that experience. As we are building a third startup and competing in a second Ironman tomorrow, we too have known adversity. I find myself contemplating one final thought: we’re on this good earth for only just a brief moment to love, to create value, to learn, and to share. Shouldn’t we be doing everything possible to max out our human experience and, by doing so, inspire others to do the same? Isn’t this the absolute greatest time to be alive? Nothing is gained by playing small.

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