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The Entrepreneurial Itch

Some moments in life stick out and etch themselves into our memories more than others. Few instances are more memorable in my own past than my first trip to San Francisco. Coming from a life in the Northeast, there’s the obvious. Sunshine in the winter, awesome views from any of the numerous hills, and sweet, old school cars pumping laid-back, Cali tunes. The most memorable moment happened on my first day in the city, after being picked up by my buddy from the airport, staring out the window. I had been working as a trader in New York, already amazed he was able to leave work midday to welcome me. I’d begun learning about websites and new technology, but it didn’t hit until I looked up and recognized the giant logo on the side of the the building.

I’m not a gamer, definitely not a mobile gamer, and quite honestly I have little respect for the company. But damn, it was 2011 and Farmville was huge. I knew Zynga. And there it was. Right behind those windows,”programmers” turned ideas into apps. Somehow, even after learning from the best professors in the world, knowing that Facebook was created mere miles from where I went to school, having bought and sold US debt for numerous countries, this made the whole world feel so much more malleable. I might eat lunch across from the guy who designed that logo or the woman who programmed that app.

The rest of my trip only shocked my senses more. I’d meet people who worked on products I actually used. A guy who helped design Google Chrome and another working at Facebook. I knew there were normal people at these companies but this was reality. We’d sit there chowing down on burritos, and when they grabbed their phone I couldn’t help but wonder: what’s going on over there? An email about a new design, a new product, a bug maybe? And then I met someone that had been in YCombinator, the startup program that has helped build the likes of Airbnb, Dropbox, and Stripe. Seriously? It was like meeting someone drafted to the NFL. I’d been bit by the bug, and from that moment it felt like life wouldn’t be enough without a nice, proper scratch.

More than six years later, having moved to San Francisco (and left), worked at tech companies, applied to YCombinator (and gotten rejected), seen Google from the inside, and taken my own run at starting a company, the itch still remains. But in that time, while obviously contributing to my inability to become a “successful” entrepreneur, I’ve kept my eyes wide and been impacted by countless other experiences. I’ve learned to cook, read, write, listen, and love. I’ve made new friends and experienced the awesomeness of sharing it all with old friends and family.

Society, at least the millennial, tech, succeed-at-all-costs society that I willed myself into, prioritizes putting your head down and coding/creating/networking yourself to the top. Success can be reverse engineered and enough analysis and grit can beat the odds. There’s uncertainty in the struggle, and anyone who’s truly pushed themselves toward anything doesn’t only acknowledge, but welcomes it. The dream doesn’t come in the payoff, an IPO or exit to a bigger tech company, it’s the process of getting there. As I’ve figured that out, discovering the payoff in my own life, it’s been the process of trying new things and unfolding life to my liking that really holds the dream.

At this point, my entrepreneurial itch is taking a back seat to all the other needs. I’ve got songs to learn on guitar, dishes to cook in the kitchen, and endless tales from history and fiction to consume. In ways, it feels like a cop out, putting aside the dream I had when I first looked up at that giant logo. But at times, the anxiety of not having “made it”, not having a company to call my own, forced so much else to the side. I thought the dream was money, then a business. Now, those ideas feel far too constrained. The world’s going to affect me far more than I can expect, and rather than putting up walls and keeping my head down toward a particular output, it’s my welcoming of change, having no idea how I’ll feel tomorrow and what I may want yet welcoming every bit of it, that I dream of.


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