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These are the researches of Herodotus of Halicarnassus, which he publishes, in the hope of thereby preserving from decay the remembrance of what men have done, and of preventing the great and wonderful actions of the Greeks and the Barbarians from losing their due meed of glory; and withal to put on record what were the grounds of their feuds.

– Herodotus, Histories


What would it be like to really and truly lose all memory?

In 1985, noted British musicologist and conductor Clive Wearing found out. As a result of a brain infection, his hippocampus was wiped out, removing all ability to form new memories. He lived in a nightmarish stasis of immediacy, sort of the yoga hippie’s version of being ‘present’, but on psychedelic steroids. His notebooks featured entries like:


8:31 AM: Now I am really, completely awake.

9:06 AM: Now I am perfectly, overwhelmingly awake.

9:34 AM: Now I am superlatively, actually awake.


His long-suffering wife wrote a poignant memoir about the experience that was perfectly titled, and captured the analogous amnesia inside Silicon Valley: Forever Today.

That phrase–forever today–captures perfectly the willful amnesia of Silicon Valley, a child-like forgetfulness where there’s always a new shiny startup or technology, and every sunrise is still greeted with the same uncynical wonder and excitement.

Now I am superlatively, actually awake. Why care about history amidst the blissful disregard?

Because history is the debt the present owes the future as it slowly fades into the past. In Silicon Valley, that debt is never paid. The United States is an inherently ahistorical nation, living perpetually in the eternal present. Californians, those most American of Americans, even more so. History is an afterthought. Posterity even more so.

Which is tragic.

Silicon Valley today is the modern-day incarnation of Florence during the Medicis or London during the Elizabethan age. It’s the scene of the biggest wealth creation since the Renaissance or the Industrial Revolution, and yet downtown Palo Alto looks some slapdash tourist village constructed for English lager louts on the Costa del Sol. We build the cathedrals and pyramids of our day solely in business models and computer code, and as anyone who has managed a codebase knows, everything will soon be either forgotten or rewritten. We live in an age whose chief achievements will never appear in a museum, grace a skyline, decorate a bookshelf, or form part of some emanation of collective memory. As Zuckerberg preached to his disciples in Facebook’s Little Red Book (it was literally little and red): “The Internet is not a friendly place….[you] don’t even get the luxury of leaving ruins.”

Or history books, for that matter.

But why such preening historical self-regard? Because life, in the living of it, is an incoherent swirl of chance and necessity, passion and luck, all doused with a fair bit suffering and toil. Silicon Valley startup life, even more so. Rendering that life into history ennobles what would otherwise be a sordid pursuit of fame and power, and crystallizes forever, like some prehistoric insect in amber, the intrigues and exertions of an entire world of builders and schemers. Per the apocryphal Chinese curse, we live in interesting times, and damn near nobody other than ourselves will ever know about it (probably).

Surely this history has been written before?

It sort of has, and I mention some precedents below. Still, there has not been a credible insider account of the tech startup game in at least fifteen years. Forget TechCrunch and Hacker News and even the tech section of The Wall Street Journal; the mainstream doesn’t know much of anything about tech world. The Social Network was a cliché, inaccurate film that failed to capture the far more interesting reality.

Ask yourself this:

Just how did we get to a world where more people on a daily basis use a thing called Facebook than have sex?

How did my co-founders and I manage to take a company from a $19,000 investor check and incorporation papers, and nary a clue about how to build a company, to a ten million dollar sale in about ten months?

Have we all gone collectively mad?

Only comparing this age to all others, in the pristine vision of hindsight, can we answer that.

In an ecosystem where people sell the future for a living and no one even remotely thinks of a time when the present will be past, someone might ask, just what the hell was all startup noise in the early decade(s) of the 21st century?

Lastly, writing serves the most personal and selfish of motives. The cynical truism is actually false. It’s not the victors who write history; it’s the writers of history who are the victors. And history is always kind to its authors.

Who the fuck am I?

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 so incompetent and vile I’ll save the historical distaste for later. 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 ad exchange 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 search 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 about what happens if you fuck with the Israelites.

But our blog was hugely popular. Which led to a meeting with Twitter Corporate Development. Which lead to meetings with other companies, and further drama. Which lead to a cluster fuck of a deal. Which lead 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.

Honored predecessors

While I have (perhaps even convincingly) run a business, raised capital, and sold air with the best of them, I never did break myself of the habits of my writer’s career. And so at conference tables, board meetings, and industry gatherings, while others were scribbling to-do lists on their legal pads, I found myself recording observations and jotting down telltale lines of dialogue on mine.

– Michael Wolff, Burn Rate

There are a couple of precedents.

Startup by Jerry Kaplan is a phenomenally well-written account of a hardware startup in the late 80s and mid 90s. It’s an absolutely gripping read about raising money from the largest investors in the land, harum-scarum product development, a failed war against Microsoft, and finally an ignominious exit as a forgotten part of AT&T. Unfortunately, not only is the technology somewhat dated (remember ‘pen computing’?), the whole power dynamic between founders, employees, venture capitalists, and incumbent competitors has totally changed. As such, it’s a wonderful snapshot in time of Silicon Valley then, but not now.

There is also Burn Rate by Michael Wolff (quoted above).While also a thrilling read, this one is even more dated and remote. The drama in question concerned the very earliest days of search (remember InfoSeek?), when bolted-on content was thought to be the key to monetization (this is all pre-Google). The stage is mostly the New York media scene, filled with Luddite publishers and shark-like financiers, and not at all the bubbly Valley we know now.

Other than that, all we have are the usual cookie-cutter, rah-rah, capitalism-as-self-actualization blog posts on Hacker News that the wantrepreneurs jerk off to. They’re about as insightful and self-reflexive as the greedy, preening autism-spectrum pricks who run the startups in question.

Speaking of pricks.

Book of the face

Every great man nowadays has his disciples, and it is always Judas who writes the biography.

– Oscar Wilde, The Critic As Artist

Facebook is the jizz in this literary money shot, and I’m well aware of that fact. But in many ways it’s not even remotely the most interesting part of the construct. For starters, I was a very late employee indeed, a bit player in the overall drama, so I don’t have some lurid anecdote about getting harassed and/or sodomized by Zuck (although I do have one about drenching his desk while brewing illegal beer).

Like the discussions of arcane 15th century Florentine politics in Machiavelli’s The Prince, the goal is not to relive or refight some ancient political conflict, or much less settle scores. The point is to extract from the particular case the general rule, such that a careful observer can apply it elsewhere. It just so happens that my big-company testbed was the service you’ve got your wedding photos on.

In some ways, the bigger story is around that little company you’ve never heard of, that I and two others founded, and somehow got (barely) off the ground, and the ecosystem that partially supported it, partially murdered it.

So, sorry. Sam Biddle at Valleywag,you might have to get your kicks elsewhere. Despite all that, will this bring me to the attention of Facebook Legal? (Hey, Colin!) Probably so.  I’ve been sued by large companies before. The big company bully always ends up regretting the tangle more than I ever did or will. Also, this.

That said, I have no intention of revealing anything truly confidential, although some things may well be unflattering or inconvenient for Facebook. Sorry to disappoint. God knows I certainly could, having been involved in most initial Facebook discussions around advertising data, privacy, targeting, as well as the recent forays into offline data matching, Facebook Exchange, retargeting, etc. Deep down inside, despite my distaste for Facebook’s current product direction (not to mention certain Facebook employees), I still want to see them succeed.

The conjurer’s booth

He who lives to see two or three generations is like a man who sits some time in the conjurer’s booth at a fair, and witnesses the performance twice or thrice in succession. The tricks were meant to be seen only once; and when they are no longer a novelty and cease to deceive, their effect is gone.

-Arthur Schopenhauer, On the Suffering of the World

Lastly, the most important reason for this book: you, the reader.

Every startup entrepreneur faces the immense disadvantage of playing a crooked, complex game for the first time, against a world composed mostly of masters. Arrayed against you is an army of wily, self-interested venture capitalists who know term sheets better than their wife’s ass. Or seductive sales execs who could make pedophilia and genocide enforceable via a legal contract. Or petulant co-founders with hidden agendas and momentarily suppressed grievances. Or ungrateful employees who are exploiting your startup until they can start their own. Or thick-headed journalists with urgent deadlines who just want you for a misleading quote. You get trounced again and again, and the only hope is that you learn something of the game before expiring. This is your principal challenge as a first-time entrepreneur: to learn the game faster than you burn cash and relationships.

And so to prevent you going like lambs to the slaughter as we did, I present you this humble volume. Per Schopenhauer and his conjurer’s booth, if you don’t personally see the show several times, you can at least read an expository description of it.

I started this chapter with a quote from one of the fathers of history, so I’ll conclude with a quote from another. Flavius Josephus in his Jewish War also chronicled an interesting piece of history, and like me, was a bit of a turncoat[1].

Its literary merits must be left to the judgment of its readers; as to its truth, I should not hesitate to make the confident assertion that, from the first word to the last, I have aimed at nothing else.

Here’s to Truth. Here’s to History.

  1. ^Flavius Josephus, despite his Romanized name, was a Jew who first fought against Roman rule in the First Jewish-Roman War (66–73 CE). He narrowly escaped a Roman massacre in a bit of mathematical cleverness that became a classic computer science problem (the so-called Josephus problem). Later, he defected to the Roman side and took Roman citizenship; he advised the Romans during the Siege of Jerusalem, which ended in the destruction of the Second Temple. The remains of the temple he helped destroy constitute the venerated Western Wall in Jerusalem, and the date of its destruction is still celebrated as the most tragic day in the Jewish calendar: Tisha B’av. The Arch of Titus, the Roman memorial marking the sack of Jerusalem, still stands in the Roman forum, and features a triumphant procession carrying off the temple’s golden menorah as a spoil of war. Not bad for a scribbler and turncoat, eh?^