startups will ruin your life in the best way

big companies scare me. i've been coming to this realization over the past couple of months, but it only distilled itself to me so concisely in conversation recently, while recounting battle scars with a friend and ex-colleague over sunlight and weekend morning coffee. we had spent a year building a brand new team together. at the end of the year, he decided to stay on, and i decided to pursue a new adventure.

i spent two and a half years of my early career at a big company which taught me a lot about the way that big companies are run. i learned a little about machine learning. i also learned extensively about navigating corporate politics, negotiating with so-called leaders, how to run an RFP, vendor relationships, colleague motivations, how not to manage projects, how not to run corporate communications, how not to organize teams, the importance of optics, corporate mediocrity, and the inevitable dysfunction that happens when non-technical project managers with shiny new "AI MBAs" are given decision-making power over engineering projects.

it was an environment which fostered and rewarded crushing mediocrity, and it was crushing me, so i left.

the skills i picked up during that time have become surprisingly useful in other settings. i find myself unsurprised by the dysfunctional dynamics and seemingly-absurd decision making processes at other large, bureaucratic places in a way that sometimes puzzles my peers who have mostly spent their time in startups or research labs.

but this experience left me with a fear of working at big companies. technology or otherwise, in all large teams there is an inescapable gravitation toward the mean; an overwhelming inertia to compromise and settle. it's the thought of settling which scares me the most. since then, i've contracted at other big companies, and i've found there is a consistent theme: no, we can't do that, you'll have to settle for this. i'm done with settling.

i knew from the very first moment i heard about the acquisition that i wasn't going to stay to be part of it, but at the time i couldn't tell you why. last autumn, when everyone asked incredulously why i was leaving when we were on the cusp of an exit, i told them that i had been recruited by founders who were extraordinary in a way that i knew i would regret it for the rest of my life if i did not work with them. this is true, but it wasn't everything.

i think i finally understand that i could never be part of the acquisition because it meant returning to be part of a big company—one where the CEO is an abstract, famous entity; where the decision makers were part of legal and corporate development teams with the goal to acquire talent; with theoretical teammates who i would never meet, with motivations i would never understand.

after spending time in tiny teams with direct access to founders, with all this autonomy, and a clear understanding of the entire company roadmap at any given point in time, i found myself unable to return to being another among thousands of engineers; to be part of a place where decisions about the office were made by HR teams who didn't understand anything about the culture, where priorities were handed down by product managers who had never written any code in their entire lives, where team org charts were changed quarterly and the way you found out was an email in your inbox titled "Team Update".

startups are life-ruining. they will change you forever in the sense that you will become accustomed to autonomy, to the thrill of creating things, to ownership, to teammates who become your closest friends, to having your opinion deeply matter to leadership, to contributing to work which is immensely, immediately impactful. and from then on, it is suddenly impossible to know anything else.

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