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I was a Berkeley PhD student in physics when the first dot-com bubble grew to bursting and popped around 2001. Between the month-long backpacking trips and the telenovela-esque romances, I switched thesis topic three times, and felt my twenty-something vitality slipping away in academic wankery. Inspired by Michael Lewis’ Liar’s Poker and the prior example of many a failed physicist, I looked for a Wall Street gig as a way out. Very improbably, I landed a job on the trading desk of Goldman Sachs, earning twice what my tenured professor made, pricing and modeling credit derivatives at ground-zero of the credit bubble. I may have owned one pair of lace-up shoes at the time, but I got used to speaking in quantities of hundreds of millions of dollars, and thinking a million was a ‘buck’, i.e., a rounding error for most purposes. I was very far away indeed from Berkeley.

Right around 2008, when Lehman Brothers and Bear Stearns blew up, I knew the financial jig would be up for a while (and possibly forever), unlike most of my colleagues, who seemed to think orgies of rapacious greed lasted forever. The only piece of the US economy that would be spared the apocalypse was clear in my mind: the Bay Area tech of my languid grad school days, and all that VC money that (hopefully) hadn’t touched the mortgage bubble.

Two weeks later, I started as employee number seventy-something at a venture-backed advertising startup. Bookended as it was by experiences at Facebook and Goldman, my time there was instructive in its awfulness and how not to run a company. But there was one piece of upside: I learned how online advertising worked, specifically its new, lightning-fast, real-time variants. As a ‘research scientist’ I tortured every piece of data until it confessed, and used it to predict user behavior, value of media purchased, and optimal bids in the largest ad auctions in the world. Dull stuff you might say, but it’s what pays for the Internet, and it would set me light-years ahead of anyone inside Facebook Ads, when the time came.

But we’re jumping ahead.

Along with the two best engineers at Shitty Unnamed Company, I applied and was accepted to Y Combinator, the Valley’s leading startup incubator. We pitched some wild, ridiculous idea around local businesses that was doomed from the start, which eventually morphed into a novel tool for managing Google ads campaigns for small businesses. The tool was beautiful, innovative, and didn’t make us a dime. More bad news: We got vindictively and frivolously sued by Shitty Company and fought an existential legal battle we narrowly won by being lying, ruthless little shits. We couldn’t raise money. We had co-founder and morale issues. Every ill that plagues early-stage startups visited us in turn, like some admonitory biblical tale.

But our blog was hugely popular. Which led to a meeting with Twitter Corporate Development. Which led to meetings with other companies, and further drama. Which led to a cluster fuck of a deal. Which led to my becoming the first ads targeting product manager on the Facebook Ads team, when it was maybe thirty or so engineers and a handful of product managers.

I spent two years at Facebook. I spent my first year struggling to turn Facebook data into money (and not very successfully at that, but more on that anon). My last year was mostly involved in Facebook Exchange, an idea that I pitched, designed, shepherded, launched, and eventually fought to protect from the forces of general big-company mediocrity that were then first encroaching on the Facebook Ads product team and have now taken over.

And now? I spend my days bobbing around on a small sailboat and writing this. I’ve imagined worse outcomes.

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