Prologue:

The Garden of Forking

Paths
Had I had been present at the creation, I would have given
some useful hints for the better ordering of the universe.
attributed to Alfonso X, the Wise, of Castile

FRIDAY, APRIL 13, 2012

The area housing the Facebook high command was a completely

unexceptional cluster of desks, remarkable only for the pile of
sporting equipment kept by Sam Lessin, one of Zucks lieutenants. Similar clusterings, arranged like hedgerows, extended as far
as you could see into either leg of the large L formed by Building
16 on Facebooks campus. The dcor was standard-issue Silicon
Valley tech: industrial shag carpet, exposed ceilings revealing
ventilation ducts and fire-retardant-covered steel beams, and the
odd piece of home-brewed installation art: an imposing Lego
wall featuring the blocky murals left by employees, another wall

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papered with the vaguely Orwellian posters the in-house printshop churned out.
At the exact vertex of Building 16 was the Aquarium, Facebooks glass-walled throne room, where Zuck held court all day. It
jutted into the main courtyard, allowing passing Facebookers to
snatch a glance of their famed leader while strolling to lunch. Its
windows were reputedly bulletproof. Just outside the Aquariums
entrance was a makeshift foyer with couches and some trendy
coffee-table book or another, which the ever-present scrum of
waiting FB courtiers ignored as they made last-minute tweaks to
presentations or demos. An adjoining minikitchen, like so many
that littered the campus, stocked plenty of lemon-lime Gatorade,
Zucks official beverage.
Inside Facebooks campus, geography was destiny, and your
physical proximity to Zuck was a clear indicator of your importance. Along the periphery of the L ran the exclusive conference rooms of Facebooks five business-unit leaders. Zucks
desk neighbors at that point were Sheryl Sandberg, the star chief
operating officer (COO) of Facebook; Andrew Boz Bosworth,
the engineering director who had created News Feed; and Mike
Schroepfer, Facebooks chief technical officer (CTO). None of
them were at their desks as I strode in from the courtyard that
afternoon.
Unlike much of the user-facing side of Facebook, the Ads team
was held at arms length, as if it was a pair of sweaty underwear,
in the next building over. That would eventually change, and
Ads team members would occupy some prime real estate in and
around Zucks and Sheryls desks. That was still a long way off,
though, and every senior management meeting I was pulled into
involved crossing the courtyard at ground level.
The centerpiece of this Facebook Champs-lyses were the letters h-a-c-k, actually inlaid in the concrete slab that formed the
courtyard and easily a good one hundred feet long. Angled to be

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PROLOGUE: THE GARDEN OF FORKING PATHS

readable on the Google Maps satellite image of campus, it appeared as the supreme Facebookian commandment.
My mission today was a meeting with Zuck, scheduled in
Sheryls conference room, which was named, for reasons I never
discovered, Only Good News. Skirting the pile of athletic
equipment around the executive-desk cluster, I walked into the
glass cube of the conference room, which featured a long, white
table flanked by a score of pricey Aeron chairs, a flat-panel screen
on one wall, and a whiteboard on the other. Most of the meeting
attendants, except the two most important ones, were already
seated.
Gokul Rajaram, the product management head of Ads and my
boss, was slouched in his usual twitching, anxious knot; he took
a nanoseconds break from his ever-present phone as his eyes rose
to mine. Next to Gokul sat Brian Boland, a buzz-cut-and-balding
guy you imagined had wrestled in college, and whom cozy, corporate life had made thick with age. Boland ran product marketing
for the Ads team, the group that wove the thick packing layer
of polished bullshit that any Ads product was wrapped in before
being given to the sales team, who would then push it on advertisers.
Sitting at a remove and staring into his phone was Greg Badros,
a former Googler who ran both Search and Ads, but seemed more
absence than presence in either. Mark Rabkin, the engineering
manager in Ads, and an early hire on the Facebook Ads team,
was closest to me in rank and attitude. A close collaborator since
my first days at Facebook, he resembled a less satanic version of
Vladimir Putin. Elliot Schrage was in his usual perch, close and
to the right of the tables end. Schrage held an elevated-sounding
and vague title but was Sheryls consigliere in all matters. In his
fifties, wearing a button-down shirt and business casual slacks,
he seemed out of place among the fleece-and-jeans-wearing tech
ies; he could have been mistaken for a senior lawyer in a stodgy

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East Coast law firmwhich is what he had been before joining

Google and the Sherylsphere.
I took a seat toward the opposite end of the Sheryl intimates,
and flipped open my Facebook-issue MacBook Pro to nervously
remind myself of the meetings script. The agenda was pitching
Zuck on the three new ads-targeting ideas I had dreamed up,
and which constituted a big monetization bet the company was
(hopefully) soon to make.
Camille Hart, Sheryls all-powerful executive administrative
assistant, or admin, milled about and tapped away on her laptop,
wrangling meeting participants.
Wheres Fischer? asked Sheryl as she blew in through the
door and took her seat at the end of the table.
No meeting could start without the minyan of Elliot Schrage
and David Fischer, the entourage she had poached out of Google.
Camille bolted out to find him.
Most everyone stayed silent, pecking at smartphones or laptops.
Boland and Sheryl quietly conferred on the state of the slides we
were presenting. Wed already prepitched her our products, tweaking the message to maximally appeal to Zuck. Any Zuck meeting
around Ads required a bit of prechewing and spoon-feeding. The
reason was simple: Ads were not something he cared about at the
time, and I imagine he saw these meetings more as duty-bound
drudgery than anything else. In one year in Facebook Ads, I had
seen the famously micromanage-y founder and CEO in the Ads
area precisely once: when he was walking around the building in
a circle to get in his ten thousand daily steps. This stood in sharp
contrast to the gossipy stories I had heard from product managers
on the user-facing side of Facebook about the withering spotlight
one lived in when working a product Zuck cared about.
In our premeeting meeting, Sheryl had let slip various hints
about the best way to present our plans. She clearly knew her boss
inside and out. Here was a woman who excelled in the role of
gatekeeper and shepherd to difficult and powerful men, whether

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that role was chief of staff for the prickly US treasury secretary
Larry Summers, or COO of and for Zuck. Between her ability to
navigate and manage the mercurial and fractious political landscape of a complex organization like Facebook, and her ability to
shape messages for Zuck, she was both de facto and de jure the
person who ran Facebook Ads. As the debate about the future
of Facebook monetization grew more polarized and heated, these
meetings would resemble the Supreme Court of Sheryl, the one
place where conflicting views could be aired with some hope of
resolution.
In came Fischer: slim, dapper, and the best-coiffed man at
Facebook. Originally one of Sheryls reports at the Treasury Department, he had begun his career as a journalist at U.S. News
& World Report, and then, as with many senior Facebook people,
joined Google. As Facebooks vice president of sales and operations, he ran the entire sales team for Sheryl, and in my time at
the company I rarely heard him utter anything other than corporate platitudes and MBA-speak (Stanford Graduate School of
Business 02, bien sr).
Greetings all around as Fischer took a seat to Sheryls left near
the head of the table, opposite Schrage. Executive admins duty
done, a satisfied Camille disappeared to wherever she lived at FB.
Noiselessly, Zuck padded into the conference room, staring at
his smartphone, and sat down in the empty seat to Schrages right.
Now the meeting could really begin.
Sheryl kicked things off. Mark, as you know weve been considering some new initiatives in Ads.
Way to understate things, Sheryl.
The company had announced its intention to go public months
ago, and the IPO was imminent. Precisely when the company was
opening itself to investor scrutiny, its revenue growth was slowing, and revenue itself was plateauing. The narratives the company had woven about the new magic of social-media marketing
were in deep reruns with advertisers, many of whom were begin-

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ning to openly question the fortunes they had spent on Facebook

thus far, often with little to show for it. A colossal yearlong bet
the company had made on a product called Open Graph, and its
accompanying monetization spin-off, Sponsored Stories, had been
an absolute failure in the market. The companys senior leadership
had called on the Ads team to dream up something fast to revive
the lagging fortunes of the enterprise. This being Facebook, the
initiatives originated not at the senior levels of the company but
rather at the lower: random engineers who had conceived of a bit
of cleverness, glib product managers (that would be your humble
correspondent) who had managed to seduce a few p eople to their
vision.
On the agenda this afternoon were three proposed products,
each very different from the other. The first involved using Facebooks Like buttonssocial plugins in Facebookeseas all-
seeing eyes that would hoover up users browsing behavior for fun
and profit.
A bit of background for the nontechie: When you load a page
in your browser, everything you see (and most of the things you
dont) is not from the company whose .com address youve entered. The way the modern Web works, different elements come
from different places. Every element you load, whether you like
it or not, touches your browser, and is allowed to read data in the
form of whats known as cookies.
The popularity of Facebooks Like and Share buttons meant
Facebook was on something like half the Web in a mature market
like the United States. As you browse the Web far and wide, from
shoe shopping on zappos.com to news reading on nytimes.com,
Facebook sees you everywhere, as if it had a closed-circuit TV on
all city streets. Facebooks terms of service had so far prohibited
the use of the resulting data for commercial purposes, but this
bold proposal suggested lifting that self-imposed restriction. As
ominous and powerful as that may sound, it was not guaranteed
to succeed, as the actual value of that data was unknown.

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I knew a thing or two about the value of Facebook data. A year

before, I had been hired as Facebooks first product manager for
ads targeting, charged with converting Facebooks user data into
money by whatever legal means available. This task had proved
considerably more difficult than it sounds. For months, the targeting team and I had been testing and ingesting every piece of Facebook user dataposts, check-ins, shared links, friends, Likesto
see if it would improve the targeting and delivery of Facebook
ads. Almost without exception, none of it increased monetization
to a substantial degree. The miserable conclusion was that Facebook, though assumed to be a rich repository of user data, did not
in fact have much commercially useful data at all. Social plugin
data, despite its ominous and all-pervasive nature, might fall into
that same depressing category.
The second and third proposals were more radical from a business, if not a legal, perspective and reflected this grim realization.
The plan was to join the Facebook Ads experience to data generated completely outside Facebook. Thus far, all ads on Facebook
used FB-only data, but this proposal would involve tapping into
external data like browsing history, online shopping, and offline
purchases in physical shops. Historically, Facebook had been a
walled garden, in which advertisers could not use their data on
Facebook or use Facebook data elsewhere. From the data perspective, it was as if Facebook was absent from the Internet ecosystem,
off on some island under its own complete control. Via two different technical mechanismsone roughly in keeping with the
existing Ads system, another vastly more sophisticatedwe were
proposing to bridge that divide at last. Both proposals, at an abstract level, were equivalent; at the implementation and business
level, however, they were vastly different, and required completely
different approaches to the advertising market.
Zuck and Sheryl hated projecting PowerPoint decks, so somebody had printed out the slides I had prepared and stapled them
into neat packets. Boland had summarized debates and meetings

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going back months in easy-to-parse bullet points on the first page.

Thats all anyone ever saw. My detailed technical schematics, with
walk-throughs of data flows and outside integration points, were,
as I suspected, completely ignored. Sheryl wouldnt have cared
about the technical detail, and Zuck wouldnt have had the patience to go through it anyhow. As I observed more than once at
Facebook, and as I imagine is the case in all organizations from
business to government, high-level decisions that affected thousands of people and billions in revenue would be made on gut
feel, the residue of whatever historical politics were in play, and
the ability to cater persuasive messages to people either busy, impatient, or uninterested (or all three).
Boland did his breezy best walking through the summary
slide, leaving out the endless debates concerning privacy and legal
regulation that had eaten up countless hours of everyones time.
If ads already made Zuck drowse, then privacy trade-offs would
have sent him keeling over off his Aeron chair. Whatever Zuck
approved, wed engineer the legal workings.
So do we think using the plugin data will make us more
money? Zuck asked.
Boland and Gokul turned to me, the usual cue for the lowest-
ranked but most-informed guy in the roomthat is, the actual
product managerto pipe up and say something.*

* Facebook, given its size, was a relatively flat organization. There were still roughly three
types of hierarchical characters in FB Ads at the time. First, the senior management level,
whose members spent their lives in a blizzard of meetings interspersed with email breaks,
and who formed a middle-management cadre between Zuck/Sheryl and everyone else.
This was Gokul, Boland, Badros, and most everyone else in that room. Then there were
the product and engineering teams, whose members usually spent their time on the engineering floor, hacking people and product. Thats me and everyone else who actually
built anything. And then, last, the sales and operations p eople, of which there was a small
army, who occupied the unfrequented buildings on campus and the equally unfrequented
international offices. The lowest level, despite often being the face of Facebook to the world
and bedecking themselves with fancy titles like head of Facebook EMEA, had no real
impact on what product got built, and were there mostly for show.

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My brain reacted like an old truck in winter, failing to start

and cranking away futilely.
Well, that depends ... I mean, there are lots of things that
affect monetization. We havent really done the controlled A/B
studies, as its legally touchy, but it is possible that its unique data
in some way. Of course, theres also the issue of whether the Like
button is even where we want it to be datawise, as
Why dont you just answer the question? blurted Zuck, cutting me off.
Panic breeds focus.
I dont think it would move the needle much, given recent
experience, I replied flatly.
Silence, as we all waited for what Zuck would say.
You can do this, but dont use the Like button, he said finally.
The statement percolated through the room.
So yes to retargeting, but no to using social plugins, reiterated Sheryl, more question to Zuck than assertion.*
Yes.
And thats all he ever said about the matter.
What was still undecided was which of the two proposals Facebook would pursue. A year from this meeting and in this same
conference room, with more or less the same cast assembled, wed
finally decide that question. It would take Facebook an exasperating year to even decide to decide. The resulting decision, when
it finally came, would see me ejected from Facebook, and change
how Facebook made money for years to come.

* Retargeting is ads-speak for the practice of showing a user ads based on what he or
she has browsed on the Web. At its simplest, its the creepy tactic of showing you an ad
for a product you just eyed on Amazon or other online commerce site. At the time of the
meeting described here, the targeting was more sophisticated than merely showing you a
version of a product youve already seen, but the term was really code for predicating your
experience on site A with things youve done on sites B, C, and D (and perhaps even done
offline, in physical stores).

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But right then, on that Friday afternoon, I was giddy inside.

The last two months of scheming had worked out. We could build
this magic targeting device I had proposed that would combine
the two great Internet data streams, Facebook and the outside
world, and change everything.
I took one look at Gokul, who half nodded. Sheryl turned to
the next item on the meeting agenda. This was her weekly meeting between her, the Ads team, and Zuck. Product reviews were
packed into fifteen-minute slots. Other product managers had
filed into the room during the brief discussion, and were waiting
their turns. As discreetly as possible, I vacated the spring-loaded
Aeron chair and slid out the door. I had my marching orders.

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