The Entrepreneurs Dilemma

Over the course of the past 2/3/4 years, whatever you want to call the path I’ve taken to starting Patch, I’ve gone through seismic changes as a person. Many things have been different: Girlfriends, best friends, roommates, houses, workout routines, city lived in, and a whole bunch else I’m sure that I’m forgetting right now.

However, one thing that has remained constant is a quote I’ve believed in (and likely mis-quoted a million times). “Career, family, social life: choose two”. I believe Randi Zuckerberg re-calibrated this for modern times throwing in sleep and fitness and giving you 3 options. Whatever the case, it brings me to a point. If you are going to build something meaningful, you are also going to have to be prepared to lose things meaningful as well.

This hit me oh so many times over the course of the past year. In order to do greater things, grow, and keep what’s important in your life, you are going to piss people off or ostracize yourself.

When it really hit me was two situations, both involving weddings of fraternity brothers (one who I considered my closest friend while in college). I was not invited to either. And, while I can be a tough mother fucker for the most part, I’d be lying if I said this didn’t hurt.

Reacting emotionally to these situations, my ego obviously got involved first. Thoughts along the lines of “what the fuck is wrong with them?”, “are they just jealous?”, “do they hate me for moving past them?”, all got in the way. And I’m sure there are some of these feelings that permeate. However, after less emotion entering into the equation, I realized that it was me who caused this, not them, and at the core, that’s completely ok.

When you think of all of the things you have to leave behind and prioritize in order to start a company (successful one), it would look like a trail of tears. I know so few founders in SF who are old cronies with their high school or college friends anymore. Maybe some here or there, but there is certainly a disconnect.

For all intents and purposes, our closest friends have to be other founders, or people in the ecosystem who understand what it is we go through. Because, when you say you are going to be somewhere, go for a drink, or be at a wedding, and subsequently have to cancel those plans because you are the CEO+CMO+VP of Sales+CFO, Janitor, Mover etc…, and your investors don’t care about your plans, who else is actually going to understand? Who else is going to understand when they haven’t heard from you for 6 months, 2 years or more and realize it had nothing to do with how you felt about them? The answer is, no one but other founders. When you say you are so tired you don’t know what day today is… the only ones who will get you are other founders. So, when an old friend asks you “how is everything going?”, how are you even able to answer without lying to them and yourself?

Entrepreneurship (the version of it we live in SF) is isolating and lonely at so many times. And in my opinion, it’s unavoidable, but rewarding in a way that I cannot describe. You must be prepared to lose things that are important to you in the pursuit of it.

Did Luke love his friends on Tatooine he had to leave when jumping on board a ship with Obi Wan? You’re god damn right he did. You think they hated him a bit when he left them and never came back even though he was saving the world (don’t worry, I don’t think I’m saving the world)? You’re god damn right they did. When he became Luke Skywalker, Jedi Master, throughout the galaxy, do you think they talked about him at their dinner parties, talking about how they used to shoot Womp Rats with Luke and how that’s how he got started on his way? Oh fuck yeah.

Just remember, all gain comes with some loss, and all loss comes with some gain. True story.