Why every Founder should run an Ironman


It was dusk. I was tired. Exhausted. Ready to quit.

I saw a light far away. I kept moving and the light came closer. I got close enough to hear the cheering that resonated from the area of the light. “John, you are an Ironman!” *cheering, clapping, roaring* “Lisa, you are an Ironman.” Finishers.

I was almost there. Within 150 yards. Finally a finisher. All the brutal weekend training sessions…20 mile training runs on Saturday and 100 mile training rides on Sunday. The myriad of drinks with the appropriate protein to carbohydrate mix (really more of a mush than a drink). The absolutely soul crushing experience of training for an Ironman was about to be all worth it.

Since the sun came up on that Sunday morning in Panama City Beach, I had swum 2.4 miles in the ocean...some of it without goggles (I lost them after getting kicked in the head by another competitor), ridden 112 miles with a nasty head wind most of the way, and had run, it appeared, 26.2 miles.

I had visions of this in my head:


Then… I remembered that I had only concluded one lap of the two lap marathon. I was so tired. So sore. So done. Yet, I had 13.1 more miles to go. Back out into the dark. By myself.

This was one of the loneliest moments of my life. One of the scariest.

Being alone is what scares me the most in life. In that moment the fear washed over me just as every cell in my body screamed at me to stop. I just wanted it all to be over. But I had trained for this. I knew what to expect. So I kept pushing forward. One foot in front of the other…….

This is the same sense that I have experienced so many times being part of the founding teams of several startups in the past decade. It is an uncomfortable feeling that starts deep in your gut and ends up illicting visceral emotions. It takes you to places you have never been before and places you never want to go again. And yet you yearn for it…to see if you can. To see what would happen if you pushed just a little farther. Because it is at this moment, when all of your sensors are on high alert…that you feel the most alive. The moment in which you get a glimpse, just the briefest glimpse, of the purpose for which you were created. You were created to create.

Without a greater purpose, this is where most people stop; this is where it ends. Only the most doggedly persistent continue to the very end, to do what they were created for: Jefferson. Jobs. Churchill. Gates. Bonhoeffer. Zuckerberg.

I just wanted it all to end.

In most employee interviews I ask this question: “What scares you the most in life?” The reactions are fascinating. Up until this point, most humans speak too much; they chatter like chimps, crowding the world with verbal noise even when they have nothing to say.

But this question almost always brings pause.

A thoughtful silence enters the room. Eyes look off into the distance and the most remarkable responses flow out of mouths. It’s often at this point that I start to see what I came for…a little bit of the truth.

I ask this question because being part of a startup is incredibly scary and there is no room, or time, for posers. I want to hire someone who has looked into the dark corner and can name the monster. I want to see depth. I want to see gumption. I want to know that when it gets tough and there’s another heartless lap to go, she will go back out into the dark where it is lonely and scary. One step at a time. Until it is finished.

In Gideon Lewis-Kraus’ brilliant WIRED article One Startup’s Struggle to Survive Silicon Valley’s Gold Rush he examines the life of a startup in the Silicon Valley and puts forth an interesting observation:

This is the basic promise of accelerators (Y Combinator et al.), that success in the startup game can be not only taught but rationalized, made predictable. Starting a company was once an urge felt only by the blindly ambitious and slightly unsound, but in the Valley it’s been ostensibly transformed into a scheduled path one can simply elect and apply for, rather as one might choose law school or Wall Street. And the promise of professionalized entrepreneurship has had a particular allure in recent years, since finance has been tarnished and a career in law made increasingly uncertain. Starting a company has become the way for ambitious young people to do something that seems simultaneously careerist and heroic. This daydream of constant killing-it has made it difficult to talk about how fearful and distraught the life of the founder can be.

I recently had a conversation with an entrepreneur who had graduated from an accelerator. He had just completed dozens of meeting with VCs and was eagerly asking for advice as this was his first startup.

I asked him a simple question:

Me: “Why are you doing this?”

Him: “What do you mean, why am I doing this?”

Me: “You just described the tumultuous struggle that you recently went through. The frustration. The long days at work. The walking away from a perfectly good and well-paying corporate job. Why are you doing this?”

Him: “I just really like startups and like fixing problems.”

Me: “Purchase Start With Why, by @simonsinek right now and don’t do anything else until you figure why you are doing this.”

At RISE, my newest startup, our purpose is very simple:

To help our members be who they were created to be by giving them the most valuable commodity in the world — time, while providing a remarkable travel experience.

This is what drives us. This is why we wake up early and stay up late. This is why we take risks. If we didn’t have this purpose I would have hung it up a long time ago. This is also why I know we will continue be successful in the future. We started 2015 with six employees and zero members. We ended 2015 with hundreds of members and we gave them back almost 13,000 hours into their lives. We are all pulling the same direction with the same purpose. I have no doubt that we will give back 100,000 hours in 2016. Keeping an eye on our purpose is going to be our biggest challenge. We will meet it.

We have built the first ever Member Air Travel Information System (MATIS) that uses algorithms in our technology platform to match demand of our members with underutilized planes. It was built with one purpose in mind: to help our members efficiently fulfill their obligations as business professionals, and still be present in their personal lives with their spouses, children and friends. Their community.

Everything we do is driven towards this end.

Joshua Bell and his $3.5M violin

The startup life is much more like the story of the world famous violinist Joshua Bell who played a $3.5M violin in a subway station in Washington D.C. The story is chronicled in Pearls Before Breakfast: Can one of the nation’s great musicians cut through the fog of a D.C. rush hour?

“At a music hall, I’ll get upset if someone coughs or if someone’s cellphone goes off. But here, my expectations quickly diminished. I started to appreciate any acknowledgment, even a slight glance up. I was oddly grateful when someone threw in a dollar instead of change.” This is from a man whose talents can command $1,000 a minute.

Before he began, Bell hadn’t known what to expect. What he does know is that, for some reason, he was nervous.

“It wasn’t exactly stage fright, but there were butterflies,” he says. “I was stressing a little.”

Bell has played, literally, before crowned heads of Europe. Why the anxiety at the Washington Metro?

“When you play for ticket-holders,” Bell explains, “you are already validated. I have no sense that I need to be accepted. I’m already accepted. Here, there was this thought: What if they don’t like me? What if they resent my presence . . .”

What if they don’t like me.

As it happens, exactly one person recognized Bell, and she didn’t arrive until near the very end. For Stacy Furukawa, a demographer at the Commerce Department, there was no doubt. She doesn’t know much about classical music, but she had been in the audience three weeks earlier, at Bell’s free concert at the Library of Congress. And here he was, the international virtuoso, sawing away, begging for money. She had no idea what the heck was going on, but whatever it was, she wasn’t about to miss it.

Exactly one person recognized Bell.

In the 45 minutes Bell played, only six people stopped and stayed to listen for a while. About 20 tossed money in his case but continued to walk their normal pace. He collected $32.17 (some people gave pennies). When he finished playing and silence took over, only one person recognized Bell’s genius. No one applauded.

This story parallels the likely legacy of an entrepreneur. Your Magnum Opus may only be appreciated by the very few.

Why SharkTank Doesn’t Give You The Whole Story…

I have some friends that were recently on SharkTank. Their company is called Foot Cardigan. They killed it. They ripped off their pants (seriously, Bryan DeLuca, your legs are great). They got several offers. They were funded. All within a few minutes, including commercials, and they were on their way. I was fortunate to be at the Foot Cardigan HQ on the night their episode aired. Their sales grew exponentially. There was cheering all around with the exception of the four founders and their significant others. They were mostly silent. Some cried. All of them realized that their lives would never be the same.

What the episode didn’t show was years of working full time jobs and working on Foot Cardigan on nights and weekends. Multiple years. No salaries. Risk of not making mortgage payments, more doing without. Fights. Lots of Fights.

I know they thought of quitting. They told me. I know they wondered if it was all worth it. They told me. Instead they went back out into the dark. By themselves. They had purpose.

The truth

Aside from my marriage and my children, being part of successful startups has been one of my best experiences of my life. To create something that didn’t exist prior to you is incredibly rewarding and absolutely worth it. My only suggestion before jumping in is to go try everything else. Work a corporate job. Become a teacher. Go to medical school or join the Peace Corps. If none of those fulfill you…then start a company.

Jason Calicanas opined on his blog:

You see, what I’ve learned after 25 years of doing this startup thing is that 99% of people simply don’t have what it takes to lead a startup — and thank God. Leading a startup is a brutal pursuit. Most days are a death march in which you work horrific hours under massive duress waiting for your chance … to join the 80% of startups that die off.

What person in their right mind wants to run marathons that 80% of the time ends in them falling between miles 18 and 25? You’d have to be an unbalanced and desperate person to want to run a marathon in which the last five miles are filled with people getting tackled and sucker punched to the ground.

So, if you’re reading this, chances are, candidly, you don’t have what it takes.

As great as that Ironman competitor looks at the start of this post, my reality felt much more like the scene below. I was mentally, emotionally and physically depleted…but as the lonely, dark night finally gave way to light at the end of the course, I crossed the finish line and heard the words I’d worked so long and hard to hear…”Nick, you are an Ironman!”. Adrenaline surged through me as I thought to myself, “Man, I can’t wait to do that again.”