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Why leaving your startup is totally like breaking up with your girlfriend

Why leaving your startup is totally like breaking up with your girlfriend

"I've had enough."

"I should have left years ago." 

"You can't give me what I want." 

These were all things I've either said or felt as I exited my startup. For three years I tried to make it work with the startup I helped launch but in the end it wasn't working and like most long-term relationships it ended in an ugly breakup. And lawyers. 

Leaving a startup is nothing like quitting a job. At a job, you only see your coworkers during working hours and maybe the occasional happy hour. For startups, at least for me, the relationship between cofounders is very intimate, like uncomfortably intimate. We all quit our real-life jobs and lived in a cramped apartment eating every meal together while we went through a three-month accelerator. I knew my cofounders sleeping habits and which ones snored. 

And for three years we tried to bootstrap it. We got a little funding, we had progress here and there but looking back I should have left a long time ago. Now that I have some distance between me and my startup, I can see it was very much like an ugly breakup with a significant other.

When we broke up, like in most relationship, I said hateful things I didn’t mean and did things I normally don’t do. 

Facebook stalking your startup

You totally Facebook stalk your startup.

Just like checking up on an ex to see who she's dating, I have to admit from time to time (sometimes more frequently) Facebook stalking to see what my ex-startup is up to. It's been radio silent since leaving and since I no longer have access to my work email, the only way to keep tabs is to check its Facebook updates. Has its status changed? Is it courting another founder? You try to see if something new has developed (like new funding) or if things are pretty much the same since you left. 

You have dreams about them

Twice I've dreamt that I was back working at my startup. It's weird because as much as you might hate your cofounders now you remember that it wasn't all bad. There was some good there. But after waking up and shaking it off, you realize leaving was the best decision. Still, a part of you misses it. 

You dread seeing your ex in public

After working side by side for three years you all know the same people. You run in the same social and professional circles so it's only a matter of time before you run into your ex. I still don't honestly know how I'm going to react when I run into my cofounders in public. Do I act cordial and just say hello? Ignore them? Flip them off from across the room? Stand on the nearest table and tell the entire room how unfair they were and how much they screwed me over? I'm hoping I can contain myself. Depends if there's a an bar at the event or not. 

Splitting up your stuff

Like most breakups there's things to split up that were accumulated during the relationship like record collections, work laptops, intellectual property and non-compete clauses. Note to future entrepreneurs: read your contract before you sign it. And to be free and clear of everything you're willing to sell your stock for practically nothing to be able to move on and start a new relationship - one with a 401K and health insurance. 

You realize it wasn't fair

  Despite everyone putting in the same hours and effort you realized not everyone was equal partnerships in the relationship, literally. It's really hard to get more of a percentage of your company once the ink has dried on the contract you barely read. Why did I go through three years of financial insecurity, stress and frustration for single-digit equity? It's hard to stay with someone or something when you're a minority stockholder and your cofounder owns 60 percent of the relationship.  

One day you wake up and realize you don't believe in the relationship anymore

For three years you convinced yourself it was going to work out, despite all the evidence pointing the the contrary. You believed in your startup. You believed you had a sustainable business model. You believed you had an exit plan. Then one day you wake up and realize you have been lying to yourself. Disrupting that market and getting to cash flow positive were just pipe dreams.

You totally don't mean it

When you break up with someone, you tell them good luck you hope they find happiness but in reality you hope they're miserable and you want to get into a healthy relationship before they do.

You told your cofounders good luck but you don't really mean it. You don't really wish them luck and success. Because if they actually did figure things out and became the next unicorn you'd have to stay away from tall buildings and bridges. You have agreed not to bash them publicly. You want to say it's because you're a more mature person but really it's because you're contractually obligated not to slander the company. 

The biggest investment you can make in your startup is your time. The worst thing you can do is not realize you are slowly failing. It's honestly like a relationship. If it's not working, it's not working. Don't give an ex or a startup the best years of your life. 

An ode to the mix CD

An ode to the mix CD

Journalism - I wish I knew how to quit you