流沙网缘

I bought my first Moleskine by sheer coincidence while shopping for craft supplies that a design course had required; I had avoided buying a notebook for the first two years at university by resourcefully (for which some might argue was born out of necessity from the lazy frugality of your average college kid) removing stacks of printer paper from the student center under a well-rehearsed, convincing ruse that I was somehow heroically fixing a “paper jam”.

By my third year I was making enough money from being a resident advisor and scrapping by with a delightful hodgepodge of research jobs that I could finally renounce my thieving ways and afford some decent stationeries, one of which was a proper notebook on which I could keep notes. I’m going to be taking actual notes in an actual notebook like a Shakespearean boss, I thought as I browsed the notebook section in the art supplies store. I picked the most conventional looking one from the pile: a large Moleskine Classic Notebook with a hard cover and plain, white pages. I knew not what a Moleskine was then or of its more hipster connotations (I swear) or why it cost an arm and leg for one, but I was pleased to have something I could, at long last, take notes on that’s not single sheet and A4-sized.

Naturally, those notes turned out to be nothing but the wild swirling caricatures of a sleep-deprived procrastinator nodding off every few minutes as the professor droned on. But over time that first Moleskine served as an outlet for my creative self, a blank canvas I painted with my thoughts and ideas and dreams. It captured the moments of blinding clarity and paroxysms of fleeting epiphany that so often defined checkpoints of my personal growth. More importantly, the notebook embodied me at my best and dutifully provided a record from which I could reflect and study.

I filled up that very same Moleskine at the end of last year, around the time when I decided to join the startup as she made the transition to the Bay Area after being accepted into Y Combinator. The fortuitous signs of a full notebook greeting a new opportunity in a new year got the best of my superstitious tendencies, so I ordered a brand-spanking new one off Amazon. In the five or so weeks since Y Combinator commenced in full swing, I haven’t written anything in the Moleskine. In fact, it’s still sitting on my shelf, wrapped in its original packaging.

Earlier this week we met with our advisor and YC partner Aaron over what seemed to be a divergence in the direction of the company and the underlying disagreement on how to best solve problems. In the hour we talked, what surfaced instead was an irreconcilable working relationship rooted in fundamental differences in personalities and misaligned expectations of roles and responsibilities. There were no hard feelings, just hard lessons learned.

Maybe I signed up for the wrong thing or for the wrong reason, as well-intentioned as I was from the start. Maybe it was more about Y Combinator, the subject of numerous pages in my Moleskine, and that was wrong. Maybe in the wake of a failed startup I deluded myself into thinking great teams are predicated on great friendships, a truism that no longer holds absolute truth.

It was also the acceptance that the startup would never be something I could call my own, not just in stake but in equal say, that cemented my decision to walk away. A sense of ownership can be a powerful motivator for a startup; in this case the lack thereof tore it apart. But if you asked me for the one reason why it didn’t work out, the truth is that it just wasn’t fun anymore, and when you’re grinding away on an early stage venture with no pay, the enjoyment you derive from working with your partners is all you have.

Egos clashed and convictions shaken, we came to the consesnsus that it’d be best if I part ways with the startup. To some extent I was relieved, freed from an incompatible environment that brought no party joy, and it hardly mattered that, to those like me who held the institution on a pedestal, this is Y Combinator we’re talking about. Aaron put it this way, “Stop thinking about YC. YC is an artificial construct, a forcing function that augments a startup’s chances to succeed. But if you can’t work together, then none of it matters. If someone tells me I can do YC but I’ll have to wear hot pants the whole time, I wouldn’t do it.” And I wholeheartedly agree with him: life’s too short to wear hot pants.

It’s been a few days since my departure, and I’m as uncertain as ever regarding my next steps, largely given that I’m still digesting what I’ve learned from this experience, and partly because I’ve grown jaded and disillusioned with Silicon Valley at large. What’s certain is that I won’t be touching startups for a very long time, and I might even stay away from Hacker News for a while. If anything, when the time comes and that startup itch manifests itself again, I’ve taken to heart that it will be of my own creation, with a team I can entrust equal ownership, and on my own terms, Y Combinator or not.

Taking the new Moleskine from the shelf and removing it from its plastic wrap, I turned to the first blank page and picked up my pen.

Here we go again.