Dating a founder

If you had told me in high school that I would ever dare try to give dating advice to anybody, I not only would have laughed you out of the room, but would have grown terrified at the prospect I might, in the future, become so very out of touch with my limitations as to attempt something so utterly outside my area of expertise.

Today, I’m somehow in a healthy relationship of almost nine years, one which has grown stronger during a year that was both immensely difficult personally and one of the most chaotic and stressful years for society on record. And for the most part, I’m not entirely sure that I’m any more knowledgeable than that high school kid was. Ask most of my friends, and they’ll agree that I basically stumbled into an amazing person who for some reason fell in love with me (a feeling I readily reciprocate despite high-school Mike’s claims that admitting to love was weak or foolish something.)

Okay, that was a bit of hyperbole, but probably not as much as you expect. I mean, I certainly do my best to be caring, and appreciative, and supportive, but it’s not like I have any special insight into how to do those things compared to the average person. I’m not a master at reading a room or gauging facial expressions, though I’m trying to improve. I don’t have the natural gift for automatic empathy other members of my family possess. I certainly can’t mind read or predict the whims of my partner, and I haven’t uncovered any secret code words of methods. We just…work, despite any of that.

So if I don’t have any special insight, what the heck am I doing writing a blog post about relationships, other than confusing the high-school version of me? Well, for starters, it’s Valentine’s Day, and as much as I am deeply uninterested in the holiday itself, it still serves as a prompt to think about one’s relationship. But I also realized that even though I don’t necessarily have any brilliant wisdom about relationships in general, I do have some context many others don’t – which is what it’s like to foster a relationship while trying to found a startup. I can’t necessarily tell you the password for balancing ambitious goals in both your personal and professional life, but I can at least outline some of the discoveries we’ve had and tactics we’ve used, in case those help others get an image of what it’s really like to do the work and keep both sides of your life going strong.

Remembering humility

Founders are, by definition, an arrogant breed. We have to be, to dare to believe we can succeed where others have failed and spot opportunities others have been blind to. That doesn’t mean all founders are stubborn oafs, of course – I at least try to make sure my self-confidence is well-calibrated! But at certain points when you’re building your startup, you’ll encounter decisions where there are two, or five, or a thousand equally viable options for moving forward. And you will decide to go with your way, not because you can prove it’s better, but because it’s yours. (There are good strategic reasons to do this other than arrogance – after all, you need to build a company which the leaders understand and know how to engage with, and you are one of those leaders, so it helps for the company to have a shape that makes sense to you personally even if it doesn’t to others.)

In a relationship, though, this tendency could easily get you into trouble. You and your partner will clash on a variety of intractable issues – including incredibly personal emotional decisions, and incredibly stupid debates like which drawer the silverware belongs in. If your partner, like you, has a founder’s arrogance, you’ll find yourselves debating these issues to no end. If they are less stubborn then you, you’ll find yourself, without meaning to, overrunning them and breaking the evenness of your partnership.

So what’s the solution? I don’t know – each couple is different. But in my case, my partner and I rely on the traditional-yet-rare technique of actually having a direct and open discussion. Ultimately, those conversations led us to a place where we were able to develop a nuanced understanding of what decisions actually matter to each other, and a way of describing things that effectively communicates to the other when we’re just noticing an amusing difference where the outcome really doesn’t matter (affectionately termed a “forks” situation after the silverware thing) and when we actually want to fight for our way being better.

Shut up and listen

As a founder, your job is to solve problems. You’ll often find yourself making executive decisions, whether because you truly believe you’re the only one with the context and expertise to move forward, or simply due to a need for speed. And you’ll necessarily become accustomed to announcing what the company will be doing, rather than merely sharing your individual perspective.

In contrast, a committed relationship is about supporting your partner – and they define what that means. If they want you to solve a problem for them, do it – but if they don’t, then you need to show them the respect of following their lead. They might just want to know someone appreciates their pain; or to use you as a rubber duck to sort out their own thoughts; or a myriad of other things. I’m sure other people have more nuanced ways of navigating this, but for me, I’ve found a simple strategy works best – when my partner is describing something they are struggling with, I don’t try to jump in with proposals or declarations. I just open with a simple question: “how can I be of help to you?”

Define your ambitions jointly

When you’re in a committed relationship, you stop optimizing only for what you want, and instead start needing to think about how you as a pair can reach whatever goals you have in mind. But that can’t be a unilateral decision – you obviously need to include your partner in the discussion. These talks might focus on purely personal ambitions – whether to have a child, say – but they’ll also commonly focus on work. Many founders grow exhausted by work and want their personal life to provide them an escape; as a result, they’ll rarely share context about their company with their partner. Others are the opposite – so deeply obsessed they can’t turn it off no matter what, and so unable to help but pull their partner into the context around the startup. (Personally I’ll swap between the two depending on the week.) Either of these can be good or bad, so long as you and your partner are actually in sync on what you both want. But the bottom line is that if you are in a relationship, work/life balance is a team sport, and you need to ensure both of you are feeling like you’re able to work together to get where you need to go.

(By the way, this applies to actually founding a company in the first place as well – if you’re already in a relationship beforehand, make sure you have a frank discussion of how a startup fits into both of your futures. It will be the third member of your relationship for quite some time.)

Find someone you respect

I’d have thought this would be obvious, but I’ve seen relationships that go other directions. And sometimes, they even work out – the range of variation of people is vast, and I certainly can’t judge anyone without understanding them. But at least when it comes to founders like myself, the reality is that you’re pouring everything you have, all of your energy…into your company. So if you want to make sure your relationship will endure, the most important thing is that you should find someone you want to not only spend time with, but genuinely hear ideas from. When you’re exhausted and tired and struggling to solve a problem, to retreat is to exclude your partner and deny that you’re part of a team. But to force yourself to do something that wears you out more would also be a problem. The only solution is to find the sort of person who helps you recharge energy when you are down, who you can’t help but seek out when you’re struggling. Someone you’ll gravitate to, and, in an ideal world, someone who doesn’t take your bullsh*t (we’ve all got something) and will pull you back if you start to drift out of orbit.

I’m extremely grateful to have a partner like that in my life. Building a successful company or a successful relationship are both huge projects – and to reverse the standard advice, just as you wouldn’t pick a cofounder lightly, neither should you pick a romantic partner who isn’t suited for you. But when you find the right one, they will become an essential part of your team working towards success – whatever that may mean for you.

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