A Startup Postmortem

And why vision is the achilles heel of any company


Today, I am announcing publicly for the first time that SkyRocket, the startup I’ve worked on since March 2013, has failed.

As you will find out if you read on, the death of SkyRocket was not as sudden as it may appear. The reality is that my company died sometime last year when I doubted myself for the first time. While I wrote about the beauty of Silicon Valley and my new life down south, my startup sat in a grave not yet marked. For about two months I was too embarrassed to admit defeat and too proud to accept my failures and move on.

In the process of starting a company I learned things about my life and the world, I worked 80 hour weeks to change, that were both painful and enlightening. This article is the first in a new series I plan to write. The theme of the series will be failure, focusing on some of the mistakes I made and how I’d advise avoiding them.


As humans, our lives are a simple game of follow the leader. During times in which we play follower, the decisions in our life are less influential than we lead ourselves into thinking. Quite often the person, or organization, that we choose to follow in the first place guides the ship leaving us to make the small choices that alter less the ends and more the means.

Recently, I was blessed with an opportunity to play the less common role of leader. I steered my own ship, and eventually convinced others to follow me. Customers, employees and mentors believed in my vision for a better world and together we slowly chipped away at a dent I promised them we could make in the universe.

In the early days of my startup, vision was trivial. It fluctuated between ambitious mission statements filled with words and phrases like “disrupt,” “forever alter” and “change,” and the simple goal of surviving one more day. For about a month vision was as important as my daily to-do list or a New Years Resolution, because failure affected no one save myself.

About a month after I decided to embark on my journey, I succeeded in selling my first 700 seats in enterprise software to a large university. Two weeks later I sold another 500. At the time I was selling 100% vision. After all, the extent of my software was a PowerPoint presentation demonstrating what SkyRocket could be. Slowly as the gravity of my company vision grew, so too did a weight on my shoulders. Tens of thousands of dollars had been bet and I was the favored horse in a race I hadn’t ever run.

By the time I hired my first three employees, the weight on my shoulders was there everyday. In every team meeting, and phone call with a customer I was reminded of the future I promised. For months I went on believing it, myself. When the checks were coming in it was easy because my vision was constantly validated by dollar signs. But one day something changed.

Money stopped coming in the door.

In addition to a lag in sales, new product challenges arose and pretty soon I began to question myself. With each pitch following that period of doubt—whether it was to a girl at a party or an interested investor—my enthusiasm and perceived confidence dwindled.

In the months that followed I experienced vision’s kryptonite in the form of self-doubt. Like Superman, I bruised easily once my incredible abilities vanished. For almost six months I had been riding on an ecstasy that woke me up at 7am everyday and kept me up until well past midnight. But in the absence of my drug—vision— I was as weak as a heroin-addict in search of his next hit.

Soon my company, customers and team became the victims of my lack of vision. And I grew fearful. Fearful that the facade I had created would disappear and fearful that those around me would notice this lack of confidence. But I’m a millennial and so in the face of failure I lifted my head higher and exaggerated daily successes more frequently.

Then I fled town.

In what would soon become the nail in my startup’s coffin, I moved to Silicon Valley and left my team and customers to dry in Vancouver. I broke a Captain’s one promise to his crew and I jumped ship. All the while my leave of absence was destroying hundreds of thousands of dollars in value.

After about a month of convincing myself that everything was ok, I received a phone call from my two remaining employees.

“We’re quitting and taking the consulting contract” was the long and short of the conversation.

Minutes after hanging up the phone, I realized that my house of cards had finally collapsed. I broke down and cried, knowing that everything I had worked so hard to build was in wreckage. The $14,000/mo consulting contract my team took with them didn’t phase me. The sudden realization that I had failed to lead or even sense an impending mutiny crushed me and left a pain deep in my heart that will remain with me until the day I die.


In reflecting on my failure as a visionary, I am reminded of a vacation I took to the mountains when I was a boy.

My brother and I had been watching a mountain biking event at Vail for a few hours when we came across a miniature course. The sign informed us that we were allowed to give it a try.

Only 8 years old at the time, I found the cliff on the course too intimidating but my brother decided to have a go. After convincing my mom he put on his helmet and started down the skinny trail. As I watched him ride, I was inspired by his ability to look ahead rather than focus on the stream 6 feet below him. For the first minute he seemed unphased by the drop but then something changed. A missed gear caused him to readjust and then look down.

Seconds later he was laying on his back, bike on top of him. Had my brother pedaled confidently and continued to look ahead he could have avoided the fall, but instead hesitation had him bloodied and bruised in the flow of a stream rather than gloating at the finish line.


This all happened, more or less, within 9 months. Compared to successful entrepreneurs my time in the leadership seat was a mere flash, but to me it feels like a lifetime. I learned a lifetime of lessons in leadership, business and happiness. I met a lifetime of incredible people. And I did what everyone should do once in their lifetime—I followed my dreams.

My bruises will heal and I’ll find a way to make my money back. I’ll learn to get back on a bike and one day I’ll jump right back in the leadership seat, bet it all and convince another group of individuals that we can make a dent in the universe.

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