Startups and Breakups
Breaking up a romantic relationship is not unlike tanking a company
There’s a lot of bad news in a startup’s life. For the founders, however, bad news is just a data point. VP Engineering candidate that we’ve been courting for a month decides last minute to pick an offer elsewhere? It’s alright, we’ll keep looking. Doesn’t look like we’re going to be able to raise more investment at the moment? There’s always plan B.
It’s a part of the job to stay sanguine and constructive. But every once in a while, things accumulate and a piece of news tips you over the edge into emotional frenzy. As a rule, this will be something unrelated to the company itself — just something that hits an already overstrung emotional cord.
Yesterday I got tipped over the edge and found myself sitting motionless on a lawn in the Presidio for over an hour. There even may have been a tear or two. A tough piece of news opened up a Pandora’s box of emotions related to the girl I once adamantly believed I was going to marry. It precipitated a lot of reflecting. I thought about why the relationship had to end so bitterly, how naive and immature I’d been in my expectations.
While I was at it, my thoughts shifted away from my personal shortcomings, and over to my ability to successfully run a startup. Fueled by Brett Martin’s recent amazing post-mortem of his company Sonar, I wondered: can we pull this off, or will I also be writing a post-mortem one day? Am I being naive in thinking we can succeed at the challenge we’re taking on with our product?
Perhaps I am. Hell, we’re trying to change how people use email. I imagine that if we fail, it will feel just as crummy as heartbreak. When you do a startup, you make yourself vulnerable, make sacrifices, put everything into it. If after all that you can’t make it work, that is a painful realization. And it is a natural instinct to avoid what caused you pain in the past.
By this logic, if this startup doesn’t make it, I will play it a little safer next time. Maybe take on just a small niche market. Do something with a straight-forward monetization strategy. And the next time I like a girl, I will be much more hesitant to let myself fall for her to such an extent that six months after the breakup it will still hurt a little every morning.
No, no, no.
That’s a scarier thought than failing hard over and over again. The lessons learned from failures shouldn’t be to play it closer to the vest the next time.
Being in a relationship and doing a startup have one thing in common: they take an immense amount of emotional investment and personal sacrifice. There is no way to face all the naysayers who “can’t see the product taking off,” if you don’t have an unwavering vision of your product making millions of users happier. And there is no way to make it through petty fights or months of long-distance, if in the back of your head you are not daydreaming at least a little bit about wedding bells.
If you fail, go all out the next time you try. That’s the only way. I promise I’ll make sure the next company is an even crazier challenge. And the next time I fall in love, I’ll make sure there is fireworks.
