How My Startup Broke Me

two people workingMy story starts in college. It starts with labels and expectations. I was a teenage computer science major who had just been awarded a prestigious internship at the university’s web department. They were in charge of maintaining everything from the public website to proprietary web-applications used by tens of thousands of students and faculty. Nearly every intern who passed through the program went on to work at companies like Yahoo or Google, and if they didn’t they started their own. Receiving that internship was my ticket to great things and I was just getting started.

I quickly made friends with my manager, who took an interest in me because of my constant need to be building something. I always had a second workspace setup and when things slowed down I’d spend my spare time tinkering with my own creations while other interns browsed Facebook. It was around this time that he asked me to start pitching our department my ideas, so once a week he’d call everyone to attention and give me the floor. I have to admit, this was a tremendous boost to my ego as he never did this with anyone else. I started to feel more like a supervisor than an intern and I was awarded more hours and responsibilities.

About half-way through my internship, I built my first company. It was one of the first truly hosted VoIP service providers. Unlike other offerings at the time, you could sign-up and provision your phones directly from the web-portal rather than needing to call a sales agent. Although we largely remained a local service-provider, our user base swelled to several thousand end-points. Eventually, this attracted the attention of a large managed service provider who acquired my infrastructure and client base. This led to new nicknames around the department like “Jobs” and “Zuck.” I was told I was destined for great things, that they couldn’t wait to see my name on the thirty under thirty and that I’d be a millionaire in my twenties.

Five Years Later

I built and sold two more applications, but I always sold too early. I never received an offer above five figures, but I always accepted because I was typically bored by that point. Right after I sold the third one, I was approached by a very successful local entrepreneur. Apparently, he was impressed with my work and wanted to know if I’d consider teaming up with him for my next venture. This was uncharted territory for me; although I was always building something, I did it alone. I didn’t like the idea of managing a business partnership on top of an application. Business partners liked meetings and in my mind, meetings were the enemy of productivity.

Against my better judgment, I decided to say yes. Wow, was this different. I was instantly swarmed with paperwork; operating agreements, partnership agreements, equity distribution agreements, investment guidelines, vesting agreements and on and on. I hadn’t even started building the application yet and he was already pitching investors. Once the first investment was secured, the real nightmare began. My business partner had a habit of disappearing for weeks on end only to magically reappear at our next investor meeting. Once we’d secured more money he’d drop out of touch again, which left me to effectively have to manage a massive project all by myself. If he did show up, I’d have to spend hours trying to explain to him everything he’d missed rather than actually working on the project.

The dark days as I like to call them, consisted of me often working eighteen to twenty hours a day. I dreamt of nothing but code and organizing layers in photoshop. We were a few weeks away from making it. As useless as my business partner was, he was really good at pitching our product. He had just secured over half-a-million dollars for us in Series A and all we had to do now was cross some T’s and dot some I’s. At least that’s what he thought.

As the deadline approached, my mood deteriorated until I was a shell of my former self. I started to hate getting up in the morning, everything began to feel like it took tens times the effort. I started snapping at people and having panic attacks on the way to board meetings. Why was this happening? I had a nice house, an expensive car, a six-figure salary, a beautiful girlfriend and I was the CEO of my own fucking company, all by the time I was twenty-five. Wasn’t this everything I always wanted? Wasn’t this everything that was expected of me? It seemed with every step forward I got further and further from happiness; I got miserable. What was wrong with me?

As the meeting drew closer, I started avoiding everyone. I knew that if I signed that agreement, I was going to be locked into doing this for the foreseeable future. My ever-unavailable business partner suddenly started calling me dozens of times a day and I sent every single one of them to voicemail. Sometimes I’d leave my house and just walk aimlessly around my neighborhood for hours at a time, trying to figure out what I wanted. I knew that I didn’t want things to stay the way they were, but I also couldn’t see an alternative — anything else just seemed like taking a step backward.

Watching It Burn

The day before the meeting, I awoke with remarkable clarity. I sat down on my computer and started drawing up an exit agreement while simultaneously transferring ownership of important assets to my business partner. With every stroke of the keyboard and every mouse click, I felt a growing sense of freedom and a surprising lightness in my thoughts. This wasn’t the grim decision I was expecting it to be, but rather it was utterly liberating. A huge smile consumed my face as I clicked send. I knew that I was about to lose everything and I didn’t care.

The meeting was a somber affair, at least for them. I on the other hand, bounced into the room like a kid on the last day of school before summer vacation. The amount they offered for my majority share of equity was a joke. I haggled a bit and walked away with less than half of my yearly salary, but I took it and smiled. My business partner didn’t smile, in fact, he was fuming. When we left the meeting he berated me in front of a crowded restaurant, calling me “lazy” and threatening to sue me for everything I had. I bit my lip to restrain jubilant laughter from bursting forth as he turned beet red. He spat a few choice expletives at me as he turned and stormed down the street.

When I arrived at my car, I patted it gently on the spoiler and laughed uncontrollably: I’d be selling it shortly. I hopped in, lit a cigarette and blasted Cee Lo’s “Fuck You” with the windows down all the way home. For the first time in years, I had absolutely no idea what I was going to be doing tomorrow and I liked it. I could take it back to the basics, I could create for the simple thrill of creating. I was well aware that this was only the spark that would start the inferno, and I was about to watch my entire world burn down around me. Good, I was actually looking forward to it with gleeful anticipation.

The next week was a complete blur. I wasn’t naive enough to believe that suddenly everything would be kittens and moonbeams. I knew that there would be a somewhat massive adjustment period before everything fell into place, before I could figure out exactly what my next move was. I had to sell my house and I had to sell my car. I had to hire a lawyer when my business partner followed through on his threat; thankfully the case was dismissed. My girlfriend of seven years left me, apparently she really didn’t like my life plan anymore. I think she was happier when it was more of my money and less of myself. I couldn’t blame her though, she had wanted it as badly as I had, it wasn’t her fault I’d changed the playbook at the eleventh hour. The funny thing is, the more I let go, the freer I felt. With each thing that was taken from me, I gained back more of what I’d lost.

Where Am I Now?

It took me some time to piece everything together, to dissect my experience and extract something useful from it. I did a lot of reading, a lot of walking and a whole lot of soul-searching. I came to love a quote from the philosopher Martin Heidegger who said:

“Anyone can achieve their fullest potential, who we are might be predetermined, but the path we follow is always of our own choosing. We should never allow our fears or the expectations of others to set the frontiers of our destiny. Your destiny can’t be changed but, it can be challenged. Every man is born as many men and dies as a single one.”

Even if I tried I couldn’t have written my own experience as eloquently as he did. My whole life I had allowed my fears and the expectations of others to set the frontiers of my own destiny. I never took time to actually ask myself:

“Is this really what I want?”

Nor did I realize how much those expectations of others had caused me so much unhappiness. When ideas of grandiosity and entitlement are spoken to you constantly, each failure feels like it weighs a thousand pounds. Why wasn’t I living up to what people thought I would become? Did I actually want to become that or did I want to be something else altogether? Fear kept me from letting go, fear of losing all of these things I thought mattered so much. It’s only now that I realize how little those things actually matter to me. I spend my days now reading, writing, meditating, walking, volunteering and using my skills to help non-profits and social entrepreneurial programs. I make about a third of what I used to and I’ve never been happier; it was the price for buying back my life. I think I just realized life is too short to waste and that:

“Every man is born as many men and dies a single one.”

Conor O’Shea is a wandering writer, developer, and humanitarian. He’s currently working on a graphic novel entitled “Cocaine, Connie, and Conversation” which is scheduled for release in the fall of 2015. You can find more of his writing here on Medium. He is on Twitter @conoro11.


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