In Startups and in Love, You Know When It’s Working

There’s always been an immediate intensity to my romantic relationships. It’s never been love at first sight—I believe “actual” love, whatever that even is, has to be built over time. Instead it’s something more like the possibility of love, the instant belief that a person is someone I could fall in love with, maybe, if everything goes right. With everyone I’ve ever been in love with, the actual love has taken months or even years to develop. But every time, I’ve known from the moment we met that the potential was there.

Someone who knows me well recently pointed out that the way my friendships have developed is nothing like this. I didn’t feel anything like “friendship at first sight” with the vast majority of the people I’m closest to. Instead we were forced together by coincidence or shared decisions and found ourselves developing friendships over time, by brute force, either discovering commonalities we hadn’t previously seen or building some that hadn’t previously existed. And I’ve never once thought that those friendships were any less real, any less valid, for having lacked that initial glimmer.

After this was pointed out to me, I started to wonder whether I’d been approaching dating the right way. I started trying more intentionally to avoid snap judgments, to not turn down a second or third date with someone based on the absence of a loosely-defined feeling that may wasn’t even a reliable indicator in the first place. But then, of course, dating is inherently about meeting a wide range of people and then narrowing in, and you have to have some kind of criteria to decide who you want to keep seeing. It’s not like I can just date everyone indefinitely and see what kinds of bonds have formed a decade later.

On top of all that, I hadn’t felt that possibility-of-love feeling with someone new in a long time. And I’d been starting to doubt whether it was even real. Had I really felt that strongly about my past loves so early on, really felt such certainty about people when I’d barely known them? Or do I just tell myself I did, letting everything that came after color the memories of everything that came before. Was I chasing the memory of a feeling that had never even existed in the first place?


But then, of course, I felt that feeling again. I met someone new, no one specially, really, except right away it was there: that feeling of possibility. It wasn’t love, wasn’t even a crush, just a voice that said: there’s something here. And I thought to myself: of course. Of course it was real.

Things didn’t end up working out with that person. After all, feelings—no matter how strong—are never guarantees. But our brief moment together left me with something lasting: a reminder that when you feel that real connection with someone, you know. For all the times I’ve gone back and forth with myself over whether or not I should keep seeing someone, for all the people I’ve dated where I just felt like something was missing even though I couldn’t put my finger on what it was, the truth is, when it’s there, it’s obvious. If you really have to ask yourself if something is working, you already know the answer.


I’ve been thinking about all this lately because, as regular readers of this newsletter know, I now work for a startup that’s all of a sudden taking off. Our revenue looks like one of those up-and-to-the-right graphs people are always lusting over, we just completed a significant fundraise, and most importantly, our customers really love what we’re building. (Just search “@beondeck best decision” on Twitter if you want some third-party evidence.) I’m not taking anything for granted—in Startup World, as in life, fortunes can rise and fall in less time than it takes to watch the WeWork documentary. But for now, in this moment at least, what we’re doing is working.

And in much the same way a new relationship casts one’s ex in a different light, On Deck’s success has led me to cast a critical gaze back at my last startup. The thing about Castle was that although we failed in the end, for most of the company’s life, things weren’t ever obviously not working. We had a product people wanted, though our ability to actually deliver on its promise was middling; we were growing, albeit not as fast as we would have liked; and our investors were happy with us, though of course they could have always been happier. Sure, new problems were developing faster than we could fix the old ones, but it always felt like we were just one small adjustment away from really getting things going.

And throughout it all, the core thesis of our business never stopped seeming plausible. (Perhaps that’s why there are now tons | of | VC-backed | startups following the trail we blazed.) Right up until the very end, whenever we’d stop and ask ourselves if this was really working, we could always make a convincing case that it was.

But being at On Deck has made me see that, in retrospect, Castle was never really working. When it’s working, you don’t have to ask yourself if it’s working—the signs are everywhere, the answer obvious. It’s like the difference between running a marathon and pushing a boulder up a hill—both are exhausting, but at least with the former, you know you’re getting somewhere. If I ever start another company, I will have learned to take anything other than overwhelming evidence that things are going well as a sign that they’re not.

In startups, and in love, and in a million other places—you know when it’s working.


Yours in wondering why more startup advice isn’t like this, while also suspecting that maybe this piece is the answer to that question,

Max