Love and Cofounders


Happy 5th! After a long weekend of inward reflection, and many cans of "America," I am officially thinking clearly again. A weekend filled with boating, stone pillars, and the raddest crews on the east coast, can make or break you. I have a lot of friends in relationships, and I couldn't help but think about the similarities between a startup founding team, and any random couple.

Now before I begin, this is not alluding to anyone in particular. There may be underlying Machiavellian morals to learn, but none-the-less I do love my friends, and their spouses. 1 is the loneliest number, but it has benefits. Being single allows freedom and rapid pivoting. Sure, when customers start to turn their attention to other players in the game, it sucks to not be able to share your pity with someone else who understands, but the strong survive in this game we play. Being a single cofounder requires grit, and delegation. Those friends who seem like they will always be single are generally one of two people: the type that get everything they want, or the type that get nothing right. Think about it.

Two, is a dangerous game. Monogamy in a relationship implies a 50/50 split of the costs and rewards of a relationship, just as in business. Yet, how many relationships have you witnessed where one person is dating up, and one person settles? Often, one founder is so desperate to find understanding, that they offer equity to the first person to "get" them, or their idea. A 50/50 split, to keep things "fair." Now in business, a 50/50 split is in my opinion, the most dangerous game one can play.

No decision is final without both sides agreeing. Like watching couples decide on dinner, it's just not as simple as it sounds. What if things get stale? What if the business takes a dip, and suddenly your partner just isn't as dedicated as they were in the beginning? Suddenly animosity is formed, and someone better comes along. Yet, you and your cofounder have been through so much (it seems) and it would be foolish to throw it away. What to do? This is the person who most understands you, and your vision, and yet this new person just seems like a better fit. A 50/50 split, almost guarantees a lot of heart-ache in the breakup process, and A LOT of money lost.

When selecting your cofounder(s), it is best to make sure that your goals are aligned, and plans are in place. Now this isn't exactly like a relationship. I'm not saying you have to come up with a plan of action for if one of you decides you don't love each other anymore, or if one of you cheats. That's just bad dinner conversation, and most certainly NOT going to get you laid that evening. But what if you could? What if you could have a prenuptial agreement to prevent the issues of a degrading startup? What if you could set benchmarks of your expectations to ensure vesting schedules are properly allocated, and that all parties remain interested, dedicated, and focused? Well- you can. In this situation, business is much easier to deal with than a relationship. In business you must always be direct. Even if you find out your love interest has a prettier friend with a better personality. You have one life to live, and you must take action. If money doesn't buy happiness, then it is up to you to minimize any hiccups to your happiness, while you chase that vision.

In business, multiple cofounders increase accountability, and productivity. Multiple personalities collude to create something bigger than them. Each founder holds the other accountable to keep the group healthy. Each founder must do their part to add value to their relationships. But just like 1, a gaggle of founders can be quite lonely as well. When you want to grow R&D, you have to convince a healthy majority to vote in your favor. When you make a mistake, you have multiple relationships on the line. This isn't intimate, it's business. Choosing cofounders and choosing lovers are not the same thing, but both can be so damn risky.

I intend to wipe this and retype, but it’s a skeleton of something better. Once, I figure out what I want, I'll clarify these opinions.

1 is the loneliest number, but at least I can decide on breakfast.


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