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This guest post is written by Kevin Krauth, CEO & Co-Founder of Orderly Health (Boulder ’16). 

Recently, the founders of all the Techstars companies currently in program were invited to participate in a personal growth and emotional self-exploration session with Jerry Colonna. In a previous Techstars alumni panel, one of the founders dubbed Jerry Colonna as “the human onion, because he makes everyone cry.”

By his own admission, one of Jerry’s claims to fame is that he made Jason Calicanis – entrepreneuer, angel investor, and notorious hardass – cry. Needless to say, I was intrigued…

The classroom side of the the room (the same space where yesterday I broke a couch in front of Brad Feld) was configured into a semi-circle of chairs situated around a makeshift stage created from lines of tape on the carpet. When I arrived, I couldn’t help but notice boxes of tissues strategically distributed around the room. Now I was nervous. 

As someone who cries at movies like Miracle and The Patriot (warning, if you are a cryer, you might not want to click on those links… you’ve been warned), I’m just not sure I’m mentally prepared to turn into a sobbing, snotty mess in front of a bunch of other startup founders. I scooted a box of tissues closer. 

For three hours, Jerry walked us through a series of slides that were coupled with a few exercises, constantly checking in to ask how we were doing.

At one of those interludes, he noticed one of the founders looking a little distraught. He put the agenda on hold to investigate. The rest of the room observed silently as Jerry dove deeper into what was going on with this founder.

In a gesture that was more sincerity than showmanship, Jerry approached the founder and knelt down, just a couple inches from him. 

Jerry: “Can I ask what’s going on?”

Founder: “I’m four years into my ‘overnight success,’ and — I’m tired.”

My understanding of the day, my situation, and perhaps even myself changed over the course of those two sentences. With his simple admission, this founder summed up some of the most misunderstood aspects of starting a company. 

Namely, it’s really, really hard.

People often think that startups are all about ping-pong and kegerators, free coffee and snacks. That they are just some adult playground where we do trust falls and draw pictures on whiteboards until investors throw money at us. 

You’ve probably heard the adage that over 90% of companies fail, but that masks the humanity behind the stories. For every one of those startups that fail, there is someone who started that company from scratch, recruited others to join them, and asked them to pour their lives into their vision. And who also spent countless hours and expended blood, sweat, and tears to try to make it work. 

That same person now has to break the news to the team. He has to tell employees that trusted him with their livelihood that they no longer have a job. He has to explain to investors that the money they gave him is gone.

He has to explain to his family and loved ones that the thing he has been working on so hard for the last however long no longer exists. He tried. He failed. He has to start over. The worst part? That failure could take years. 

The founder from the conversation above is far from failing. In fact, his might be the company best positioned for success of all the Techstars’ companies in this class. But it’s taken years of carrying the burden of the fears I’ve outlined above, and in that moment, you could see the weight of that burden in full force. 

I only just managed to choke back my own tears in reflecting on what he was going through, but then again, I’m pretty early in this journey. I’ve still got three more years before I’m at the same point in my quest for an “overnight success” of my own.

I just hope I have the strength to make it that far.

 

Reprinted with permission from thisis.orderlyhealth.com


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Kevin Krauth Kevin Krauth
(@KevinKrauth) Co-Founder/CEO of Orderly Health. Product guy. Explorer. Hustler. Teach me something! @kevinkrauth



  • It can be incredibly lonely… but life is made infinitely easier with great partners and friends. Make sure you have some going in. Love the transparency… this shit is real.

  • Thanks for sharing this post. I’ve had the honor of working with Jerry one on one a couple of times as well as in a group at the first CEO bootcamp and he is incredible. I don’t think I’ve ever spent more than 2 hours with him and not been crying my eyes out.

  • Russ Wilcox

    The best thing you can do as a stressed-out Founder CEO who is reading this article is to join a CEO group. Meet quarterly with others facing similar issues, and share the journey together. It helps a lot.

  • Well you guys have Jerry and we live in one of the most supportive startup communities in the world. I think more posts like this will always be appreciated by those who are struggling down this often lonely and unforgiving road.