Going The Distance

“A champion is someone who gets up when he can’t.” – Jack Dempsey

Those who know me will tell you that I talk about boxing a lot.

I first stepped into a boxing gym six years ago. I wanted a fun and engaging workout, and someone I trust suggested it to me.

I got the fun and engaging part in spades. What I did not expect were lessons I apply to my professional life.

Three things are a constant in the ring: presence, stamina, and fear.

In my twenty years of operating prior to joining Collaborative Fund, I’ve experienced how presence, stamina, and fear impacted me and those around me. I also see it often when it comes to the challenges our founders face as they’re building a business.


When someone is trying to hit you – often pretty damned hard – your mind does not wander. You aren’t thinking about the emails lingering in your inbox. You are, existentially, present and focused.

For many of us, the default state at work might consist of skipping between one task and another, phone-in-hand, pecking away at it while colleagues are mid-sentence.

The really tough stuff at work, however, requires presence and focus. It may be a gnarly technical issue, a hard budgeting decision, or a difficult conversation with someone on the team. The best leaders are able to put aside distractions and focus on what matters most. This requires ruthless prioritization and self-control. A sharp focus on the most meaningful issues is the only way to drive real change.


Boxers love the jump-rope. We use it to warm up and to set the stage for what we call “active rest,” which helps build stamina. There is no resting in boxing because when you’re in the ring, and you are absolutely exhausted, unfortunately you can’t sit down and take a minute. Pacing yourself, understanding how to “rest,” and pushing through when you just want to give up – that’s what matters.

Stamina is one of the most underappreciated qualities necessary in building a business. We are constantly reading stories of unicorn rounds, monster IPOs, and we celebrate invincible-seeming founders and CEOs. The reality is that those leaders are human. They have the same anxieties and fears we have. I promise you, they went through many more “downs” than “ups” in the (much longer than you imagine) story of their success. And, there are many more failures than there are successes. What matters is lifting yourself up when you feel like you can’t. There is no better indicator of future success than resilience, determination, and stamina.


I thought I knew what it meant to be afraid. I grew up in New York City in the 1980s. It wasn’t a war zone, or a third world nation. But it was a different time and the city was not a very safe place. I was robbed growing up… twice. The memory of that experience is nothing compared to the sheer terror I felt the first time I was in the ring and someone came barreling at me. It was a blur of sweat, spit, leather, and blood. Every cell in my body seemed to scream out: “RUN!” The reaction was physical. My mind and my body worked in self-preservational ways to accelerate my heart rate, leading to rapid breathing, and an almost out-of-body experience. Over time, I taught myself to control my mind and my body. I had to get comfortable with the fear. I had to embrace it. As one of my first trainers told me, “boxing is like swimming. If you get into the pool you’re going to get wet. If you get into the ring, you’re going to get hit.”

We rarely talk about fear in the context of business. But, it’s there. The biggest mistakes I’ve made in my career stemmed from fear; fear of losing my job, fear of going against the tide, fear of conflict. Dreading a conversation with your investors? Wishing you didn’t have to fire your co-founder? Can’t sleep because you know the all-hands tomorrow is when you tell everyone the bad news? We don’t talk about it, but fear creates the loneliest and toughest times for most CEOs. When the fear comes barreling at you, and your heart is racing, and there’s no other option, you can run away and avoid things, or you can take a deep breath, relax, and embrace it.