An empty pageant; a stage play; flocks of sheep, herds of cattle; a bone flung among a pack of dogs; a crumb tossed into a pond of fish; ants, loaded and laboring; mice, scared and scampering; puppets, jerking on their strings; that is life.
In the midst of it all you must take your stand, good-temperedly and without disdain, yet always aware that a man’s worth is no greater than the worth of his ambitions.
—Marcus Aurelius, Meditations
FEBRUARY 2010
It’s not the rats who first abandon a sinking ship. It’s the crew members who know how to swim.
By January 2010 it was abundantly clear that Adchemy was a complete failure, a hecatomb of human effort sacrificed at the false altar of Murthy’s ego. Real-life experience is instructive, but the tuition is high.
The first sign of trouble was an externally visible one, a symptom that any suitably experienced startup practitioner could have detected: nobody from the early days of the company was still around other than Murthy. Every other single cofounder or early employee had left. As Vonnegut wrote in Bluebeard, never trust the survivor of a massacre until you know what he did to survive. And indeed in this case, Murthy wasn’t a mere survivor, but rather an author of said massacre.
Like Stalin’s USSR doctoring photos featuring former party favorites, removing the now-purged victims from its history, a startup will disappear the former founders and employees from its “Team” page online. The official history of the startup, at least as told by itself, will only ever mention the current leadership, and reweave some narrative about how the current team is the God-ordained combination of human talents that will take the startup to the stratosphere. This is utter tripe, but it’s the party line you’ll be told. Discreet inquiries on CrunchBase or LinkedIn, or emails to professional connections, tell the real tale.* Don’t work for the survivors or architects of massacres. You’ll live just long enough to regret it.
Here’s a second sign: the startup makes money, lots of it. You heard right. This was another illustrative Adchemy problem, though a relatively rare one. Adchemy made software that automated and optimized the laborious task of running ad campaigns. In Silicon Valley, there’s a piece of tech-speak called “dogfooding,” which basically means using your own product.† The idea in this case was to have a marketing team actually running marketing campaigns, and then selling the prospective customers in a legal but slightly sketchy underbelly of the online world called the “lead generation” industry. Adchemy sold nothing itself, only the lists of people it had found via ads to those who actually sold something, like a mortgage refinancing or a criminology degree. It’s serious business, though, and Adchemy made something like $6 million per month selling mortgage leads to Quicken, and online education leads to the University of Phoenix (I want to take a shower just reading those names). In the same way that a trust fund just makes a drug addict’s spiral more long lasting and painful, a cash-generating business that doesn’t improve the product postpones the inevitable by floating the charade, all the while actually making failure more likely. This strategy can work as far as keeping a company afloat while it’s working out the kinks in its core program, but it’s tricky, and it requires absolute management discipline to not lose focus on the product the company was created to perfect. Murthy was like the one heroin-addicted lab rat who could never stop hitting the lever for more.
Third, Adchemy had no clients for the actual product. An absolutely clear sign of flailing failure is when a company’s quarterly report features a new set of corporate logos, each a breathlessly awaited beta customer who’s just going to blow the doors off usage or revenue in the future.* That’s fine for one quarterly report, but after a year’s worth of an ever-changing list of beta customers, with none morphing into full-on clients with contracts and recurring revenue, you’re chasing a mirage. All you’re seeing is a logo version of the sales team’s leads list as they churn through potential clients.
The last symptom of terminal illness, counterintuitively enough, is loyal employees.
Despite the mismanagement, many of Adchemy’s two hundred or so employees felt a strong sense of loyalty to both Murthy and the company. Many of these were very skilled professionals who could have been employed elsewhere, who nonetheless put up not only with the poor management of the company but also with outright mistreatment. Murthy’s tantrums were legendary, and he often insulted employees and in some instances fired them without cause. He once broke my finger when he flung a baseball at me with no warning (I was standing in front of floor-to-ceiling glass, and was forced to catch a fastball), and then mocked me for it publicly for months, merely for the sake of fun.* And yet many of his employees spoke well of the company and even exercised their options to buy company stock, causing them to lose large portions of their life savings when the company folded.† Even after quitting or being fired, former employees would host Adchemy alum happy hours and get back together, like some reunion tour. Here’s the lesson: when the company’s employee retention strategy is cultivating Stockholm syndrome, you’re in the wrong company.
Saint Augustine thought the best way to heavenly salvation was to know the route to hell, but avoid it. Consider the various paths to hell I’ve taken for you, dear reader, and do otherwise.
If everyone believes in delusions such as democracy or religion, they sort of become true—certainly more true than when a delusion is nothing but a presumptuous neuronal spark in someone’s mind. If you consider yourself a Gates or a Musk but aren’t seen as one, then you enter the realm of felt injustice. You assign yourself a certain value, but society ranks you at another. That difference between society’s perception and your own is the gap of injustice you feel. Multiply that gap times your ego, and you get the total balance of rage you’re to expend in your startup quest.
In just such a rage-filled state I began working on our Y Combinator application.
Two other Adchemists and I had clicked socially, and for months were constantly chatting about startup ideas. One you’ve already met: Matthew McEachen, a.k.a. MRM, with whom I’d built the real-time bidding engine. He was the company’s longest-serving and most productive engineer, and we had collaborated, he as lead engineer and I as research scientist, on a number of projects. The second was Argyris Zymnis, a recent graduate from a famous artificial intelligence lab at Stanford. He was one of the rising stars at Adchemy, due to both his high-level machine-learning brains and his coding skill.
Aside from our lunchtime conversations and odd Sunday phone call, though, we hadn’t formulated any clear business idea. Procrastinating on a Monday, I decided to read an essay by Paul Graham. PG, as he’s known to the cognoscenti, founded an online store builder called Viaweb in the early days of the Web, which got bought in the $40 million range in 1997, and eventually became Yahoo Shopping. In his postacquisition freedom, he created one of the more incredible institutions in Silicon Valley: Y Combinator.*
Twice a year, every year, Y Combinator accepts a few dozen startup hopefuls into what can only be described as a startup boot camp.† They are given a tiny amount of money and the goal of shipping a product by the end of three months. Some come in with nothing but a few hacked-up lines of code and an idea; some have entire going concerns that have already raised money.‡ Three months later, they all pitch at Demo Day, a major event on the Bay Area’s venture capital calendar.§
PG is the leading apostle, to not say messiah, of the startup gospel, and other than maybe Marc Andreeson, possesses the only prose style among techies that doesn’t trigger a literary gag reflex. His lucid essays dispense with any ego and pretense, and read like a how-to manual for the tech endeavor. Reflecting his background in philosophy and formal logic, his tightly argued disquisitions often read almost syllogistically, like a Socratic dialogue, as he dissects funding rounds, hiring, cash flow, and product development.
Having forgotten the URL to his essay library, I entered “ycombinator.com” into my browser. The minimalist website carried a picture of a geek in a weird orange-walled room, some links to press coverage, and one link that was tantalizingly titled “Apply to get funded. Deadline March 3, 2010.”
Isn’t that something?
Thought #1: We should apply.
Thought #2: It’s March 1.
That very afternoon, I pulled the classic move you too should use to seduce a potential cofounder into leaving his or her steady-paycheck job. I gave Argyris a physical copy of “How to Start a Startup,” a blog post by Paul Graham, which is the crack-like gateway drug to the startup addiction.
We spent the next two days clandestinely hammering out our pitch in the office, or playing hooky and working at a nearby Peet’s Coffee. I did most of the actual writing.
What is writing?
It’s me, the author, taking the state inside my mind and, via the gift of language, grafting it onto yours. But man invented language in order to better deceive, not inform. That state I’m transmitting is often a false one, but you judge it not by the depth of its emotion in my mind, but by the beauty and pungency of the thought in yours. Thus the best deceivers are called articulate, as they make listeners and readers fall in love with the thoughts projected into their heads. It’s the essential step in getting men to write you large checks, women to take off their clothes, and the crowd to read and repeat what you’ve thought. All with mere words: memes of meaning strung together according to grammar and good taste. Astonishing when you think about it.
The boys started hacking on a basic demo we’d be able to present, assuming we managed to beat the terrible odds and get invited to pitch the YC partners.
Specialization of labor was already happening. The boys were good at making computers do hard things via code. I was good at making people do hard things via language—and good at figuring out what big bets were worth making. The boys weren’t totally convinced about this YC stuff: the money was a pittance, the equity taken large, the benefit unclear (to them). But I was as convinced as a Bible-beater is about Jesus that this would be an essential step in our future, and I would be proved more than right.
So what idea were we pitching exactly?
The short answer: it didn’t matter.
Like the canniest early-stage investors, YC cared a lot more about the team at this point than whatever improbable idea we might have. The latter was really there only to judge the former; it was valueless in itself.
Don’t believe me? Think your idea is worth something?
Go and try to sell it, and see what sort of price you’ll get for it. Ideas without implementation, or without an exceptional team to implement them, are like assholes and opinions: everyone’s got one.
Incidentally, the fastest way you can indicate your level of startup naïveté to a VC (or to anybody in tech), is either by claiming you’re in “stealth”—that is, with an idea so secretly valuable you can’t disclose it—or by forcing someone to sign a nondisclosure agreement before you even discuss it. You may as well tattoo LOSER on your forehead instead, to save everyone the trouble. To quote one Valley sage, if your idea is any good, it won’t get stolen, you’ll have to jam it down people’s throats instead.
For the record, though, here’s what we came up with:
One of the great challenges in marketing is the divide between the online and the offline worlds. What you buy via the Internet and your digital persona is completely separate from what you buy in person, and the two data streams rarely cross. Imagine if an advertiser knew you bought SUV-sized packages of diapers at your local Walmart; how would it target different Internet ads at you? Conversely, if you were searching online for a particular gadget, how do you know if it’s sitting at your local Best Buy, ready to be bought, rather than your waiting two or three days for Amazon Prime? Our idea boiled down to building an app that allowed local store owners to scan a product’s bar code, which would then instantly generate an online ad campaign that advertised the fact that the product was for sale locally.
Here’s some startup pedagogy for you:
When confronted with any startup idea, ask yourself one simple question: How many miracles have to happen for this to succeed?
If the answer is zero, you’re not looking at a startup, you’re just dealing with a regular business like a laundry or a trucking business. All you need is capital and minimal execution, and assuming a two-way market, you’ll make some profit.
To be a startup, miracles need to happen. But a precise number of miracles.
Most successful startups depend on one miracle only. For Airbnb, it was getting people to let strangers into their spare bedrooms and weekend cottages. This was a user-behavior miracle. For Google, it was creating an exponentially better search service than anything that had existed to date. This was a technical miracle. For Uber or Instacart, it was getting people to book and pay for real-world services via websites or phones. This was a consumer-workflow miracle. For Slack, it was getting people to work like they formerly chatted with their girlfriends. This is a business-workflow miracle.
For the makers of most consumer apps (e.g., Instagram), the miracle was quite simple: getting users to use your app, and then to realize the financial value of your particular twist on a human brain interacting with keyboard or touchscreen. That was Facebook’s miracle, getting every college student in America to use its platform during its early years. While there was much technical know-how required in scaling it—and had they fucked that up it would have killed them—that’s not why it succeeded. The uniqueness and complete fickleness of such a miracle are what make investing in consumer-facing apps such a lottery. It really is a user-growth roulette wheel with razor-thin odds.
The classic sign of a shitty startup idea is that it requires at least two (or more!) miracles to succeed. This was what was wrong with ours. We had a Bible’s worth of miracles to perform:
Small-business owners had to use us for all their marketing.
We had to solve the scanning-a-bar-code-with-a-phone problem.*
We had to generate a comprehensive retail product database, with relevant metadata like prices, reviews, and model numbers.
We had to programmatically generate ad campaigns based on that product database.
We had to design the world’s best small-biz marketing and campaign management workflow, one that allowed even unsavvy marketers to be successful.
That was five miracles, just for starters (not to even mention practical ones like raising money and getting along with cofounders). It was four miracles too far. Any single one of those could have encompassed an entire funded startup’s efforts, and in fact I could tag every line above with two to three startups that had attempted it. And here we were proposing taking down all five with three scared guys and no business network or money. Even in our jackass naïveté, we started realizing this soon after the YC interview, which is why we eventually did that classic startup move: a pivot.
This is absolutely canonical startupese, and worth exploring for a second. You can’t read an article in Wired or Fast Company, some fawning fiction about a startup’s inexorable and well-deserved charge to world domination, without reading this word at least once.
A “pivot” is supposed to recall a ballerina’s demi détourné, a delicate change of course as graceful as it (hopefully) seems intentional. In reality, a startup’s pivot is a panicked sprint comparable to that of a Titanic passenger who’s spotted the last open life raft. It wasn’t even a onetime thing: our final product would be informally titled “Plan J,” given the number of turns we had taken since “Plan A.” But there you have it, dear reader: we made a “pivot.” Plié!
But we’re getting ahead of ourselves. All this would become clear only after numerous strolls with Paul Graham, something we hadn’t even won the right to have yet.
Back to me skulking at Adchemy while working on a Y Combinator application. If my reading of YC’s and Paul Graham’s essays was correct, then bomb-throwing anarchist subversive mixed with cold-blooded execution mixed with irreverent whimsy, a sort of technology-enabled twelve-year-old boy, was precisely the YC entrepreneur profile. Figure out a point of overlooked business or technical leverage, interpose some piece of cleverness, and gleefully marvel at the resulting disruption (or destruction).
In that spirit did we respond to my favorite question on the YC application:*
What (non-computer) system have you ever hacked?
I conducted a man-in-the-middle attack on Craigslist’s online dating ads. I posted an ad as a woman looking for a man, and as a man looking for a woman. I’d pass email from real man to fictional woman as the replies of fictional man to the real women, and basically crossed the email streams. At one point I shifted each real person off my fictional email addresses, and to the corresponding opposite-sex real email addresses. For all I know, it resulted in a marriage, as I never saw emails after the rewiring of the email flow.
And on it went for the rest of the questions.
The sound-bite tagline for the inchoate idea was drawn from personal history: we were building the “Goldman Sachs of advertising,” a grandiloquent assertion if there was one. This formulation of “the X of Y,” where X and Y are two easily understood things, but their intersection is novel or intriguing, was also classic Y Combinator thinking. PG had actually suggested such a trope in his essay on pitching to investors. It’s now terribly cliché, but at one point, like any meme, it enjoyed a period of almost classic establishment acceptance. Even now you hear it occasionally: “the Uber of bicycles”; “the Netflix of men’s underwear”; and so on. It’s a one-line way to instantly make your weird techno-business pastiche understood, even if only partially.
The boys weren’t totally convinced, even as we hustled to get our application in on time. They wouldn’t be totally convinced until our first YC meeting, in which we were given a rousing oration by Paul Graham. Even in those tentative Adchemy days, though, I knew YC would change everything if we got in.
Plus, it was a prize, and a difficult-to-attain one at that. Whenever membership in some exclusive club is up for grabs, I viciously fight to win it, even if only to reject membership when offered. After all, echoing the eminent philosopher G. Marx: How good can a club be if it’s willing to have lowly me as a member?
If you had been standing on the corner of Broadway and MacArthur Boulevard in Oakland the night of March 7, 2010, you would have seen a curious sight. A heavily pregnant woman, bent over in pain and scarcely able to walk, was being half carried, half dragged across the street by a tall, goateed man. The woman could barely stand, and needed to pause and cling to either the man, or any fixed object, as they struggled across the last couple hundred feet. Every ten paces or so, the woman would double over and gasp in pain, bringing everything to a halt. The man was simultaneously trying to check for traffic, keep his female companion from collapsing, tow a large suitcase, and navigate the whole lurching ensemble toward the emergency room door. That goateed man, gentle reader, was me. The woman was a former City of London derivatives trader.
She was thirty-seven weeks pregnant.
We had known each other for thirty-nine weeks.
Let’s rewind before we fast-forward again.
“Life is what happens when you’re making other plans.”
If you ever run across an online dating profile with the above as a tagline, be aware you’re in for one fucking life-changing date. I had found British Trader’s profile while searching for the keyword “sailing.” Thematic searches (e.g., “physics,” “PhD,” “beer”) were my way of finding some iota of common ground with which to structure an introductory message.
At the time, online dating sites distinguished themselves mostly by the demographics of their members. Craigslist was for escorts, fat chicks in Fremont, and serial killers. OkCupid was for penniless hipster chicks who lived in shared flats in the Mission. Match.com was for professional women busy with the time-honored tradition of husband shopping. Choose your audience, and write your ad copy. Mine was heavy on the sailing and outdoor adventuring. Zero mention of diaper changes and daycare drop-offs. Truth in advertising, more or less.
She had vaguely Slavic-looking cheekbones and feline eyes. Her Match profile photo featured her at the tiller of a boat, which instantly quintupled her attractiveness. Message led to dinner date. Dinner date led to an opera outing. One early Friday evening, dressed in her corporate finest, she appeared unannounced at the boatyard. My twenty-six-foot sloop Moksha was hauled out on land, and I was busily refitting it for serious offshore sailing. Covered in dust and grease, I welcomed her to my boat. She climbed up the precarious twelve-foot ladder to Moksha’s deck, which towered over the ground due to the boat’s deep keel.
Then, a romantic reversal.
The following weekend, a tall, rangy guy put his boat next to mine in the yard. A strapping and strutting South African, he walked over and we started talking boats. We got along famously, and continued our unending string of boat talk with beer and pizza at the local red-and-white-tablecloth Italian place.
He was, as fate would have it, British Trader’s ex-boyfriend, who had recently and unceremoniously dumped her. This business was serious. As I’d eventually learn from British Trader, they had tried having a child despite never marrying. Their inability to conceive had convinced British Trader she was barren.
He and I ended our boozing and bullshitting and got back to work on our respective boats. As I was painting the bottom, I looked over and saw some hot chick talking to my new South African friend. I saw only her jeans-clad ass. Given my as-yet noncomprehensive knowledge of her anatomy, I didn’t recognize her. Of course, it was British Trader, stopping by the yard to check randomly on my progress. Given there was only one large boatyard for serious refitting in the East Bay, meeting her recent beau wasn’t a completely improbable coincidence.
Weirded out by my bonding with her ex, she decided to end the budding romance. But then a week later she changed her mind. I had brunch with her and her female confidante. On my finest social behavior, I passed muster with her friend. The next invitation was dinner at her house. When I appeared on her doorstep with a bottle of wine and a smile, she opened the door conspicuously made up, perfumed, and in a fetching dress. The moment that door swung open, I knew I had her.
The contemporary honeymoon of a several-week fuck-fest, consummated at the start of a new romantic liaison, played itself out comme il faut. No surprises really, other than British Trader’s taste for being physically dominated in bed, a bit of a surprise given her alpha-female exterior. To a woman, every girlfriend of mine has been intelligent, ambitious, and independent. Until very recently, all were vastly more successful and wealthier than me. And yet, come the pressing hour of physical need, so unfolded the countless boudoir scenes recalling Fragonard’s Le Verrou: a ravished chambermaid, half resisting and half yielding, violently seized in the arms of her predatory lover, who slams shut the bolt on the bedroom door.
The backdrop to the tryst turned relationship was a modest bungalow fixer-upper that British Trader had bought, taking advantage of a corporate relocation package. She made Bob Vila of This Old House look like a fucking pussy. She had ripped out the ornate and custom built-in shelves and display case from one room and installed them in another. The flooring was down to the planking, to be redone in fresh hardwood (by her, with a nail gun and lots of patience). The only room that was even remotely livable was the kitchen (which featured beautiful hardwood counters that were regularly oiled). Her bed consisted of a cheap foam mattress about the width of an extra-jumbo-sized menstrual pad inside a room stripped to the wall studs. The floor was dusty with drywall powder from the demolition, and postcoitally, it was all I could do to balance myself precariously on the edge of the pad and off the drywall dust. Morning showers were in the one functioning bathroom, whose empty window frames were covered in plastic. A molded plastic shower in the corner and a lonely-looking white porcelain toilet were the only signs of civilization in what appeared to be the inside of a garden shed. The scene of conception was either the aforementioned foam pad, or the hardwood kitchen counter.
Two generations ago, her branch of the family, moneyed Jews in czarist Russia, had seen the revolutionary writing on the wall and had fled to the United Kingdom. Another branch moved to China and became an established trading family in Harbin. In Britain, the family made the unlikely transition to landed gentry, and ran a farm in Bedfordshire. A great-uncle was elevated to the peerage, and a second cousin shared the Nobel Prize with Alexander Fleming for penicillin.
When she was in her teens, her father decided to move the family to the United States, where they suffered a financial reversal she was unwilling to talk about. Suddenly not among the moneyed class, she hustled herself through the redbrick boondocks of the University of Vermont. Citibank internship led to Deutsche Bank job, and after a few years she was an equity derivatives trader at Deutsche, holding her own against the toff sharks of the City of London.
She had wild green eyes, with unnatural red spots in her irises when you pulled close, reminiscent of that Afghan girl from the National Geographic cover. Her personality was flinty and rough, and as leathery as her skin. She had spent years between various jobs backpacking around the rougher parts of the world. She was an imposing, broad-shouldered presence, six feet tall in bare feet, and towering over me in heels.
Most women in the Bay Area are soft and weak, cosseted and naive despite their claims of worldliness, and generally full of shit. They have their self-regarding entitlement feminism, and ceaselessly vaunt their independence, but the reality is, come the epidemic plague or foreign invasion, they’d become precisely the sort of useless baggage you’d trade for a box of shotgun shells or a jerry can of diesel.
British Trader, on the other hand, was the sort of woman who would end up a useful ally in that postapocalypse, doing whatever work—be it carpentry, animal husbandry, or a shotgun blast to someone’s back—required doing. Long story short, you wanted to tie your genetic wagon to the bucking horse of her bloodline. Which is why I was less nervous than I should have been on a random Saturday in July, when I showed up for a brunch appointment and found her uncharacteristically moody. She complained of feeling nauseated and slightly out of it.
With perhaps too much offhandedness, while grabbing the local newspaper off her couch, I suggested, “Well, perhaps do a pregnancy test.”
Like any male who’s played it fast and loose with the safe-sex rules, I’d had my fair share of scares. I was on season four of the show whereby tear-filled woman X shows up two weeks after the shag saying she had “missed her period” (sort of in the same way I’d say I “missed my bus”). Nothing had ever come of it, and after the third showing you just wanted to say, “Look, woman, unless you’ve got a screaming infant in your arms and it looks like me, we have nothing to talk about.”
She’d have both soon enough.
“Well, I did go to the doctor,” she replied instantly.
Things took on a rather portentous air for a casual Saturday-morning brunch.
“Ah . . . and?”
“I am pregnant.”
BAM!
A human life.
Shit, I thought.
I could hear God laughing in his vaulted hangout. Life is what happens when you’re making other plans indeed.
By her account, British Trader had broken into tears on hearing the news from her doctor, whom she had gone to see on some routine visit. Yeah, that old story. One look into her hard, green eyes, and I knew this kid was seeing the light of day.
Due more to some residual Catholic guilt and Hispanic chivalry than true love for British Trader, I sublet my one-bedroom bohemian pad in the Mission, which had followed my hippie-chick household, and moved into her home turned construction site. I’d make a go of this domesticated parental life.
If you jump into the abyss, jump headlong.
Passed out on a gurney, British Trader was bleeding. I watched with increasing alarm as red streaks traced bloody spiderwebs across her thighs. The nurses milled around like bored bureaucrats at a foreign post office, and talked about paperwork and the weather.
The progress of birthing is measured in centimeters. Seven centimeters dilated: too late for anesthesia, too late for fashionable breathing exercises. It was showtime.
I invite anyone with a philosophical bent to witness a human birth and observe as unstoppable forces meet immovable objects, with neither yielding. Modern medicine does little to resolve this paradox made flesh. The only real differences between the bloody, screaming tableau before me and that of, say, my grandmother’s birth a century ago in rural northern Spain by candlelight, were the little plastic packets of mineral oil, like the salad dressing at a Denny’s, that nurses would regularly crack open and pour over the heaving, tumescent mass down south.
It was a sweaty, white-knuckle affair shattered by piercing shrieks of pain that resonated across the maternity ward, and which the heavy institutional doors the nurses slammed shut did little to stifle. I quietly entertained bouts of Mad Men–esque nostalgia for a time when men simply paced nervously and smoked in some other room while the dirty business was completed.
After two hours of battle, old flesh yielded bloodily to new, and Zoë Ayala came into the world.
As some sort of perverse parting gift, I was given the honor of cutting the umbilical cord. As thick as a man’s finger, with a yellow film over a deep purple core, it yielded to my snipping with a pair of small scissors, making a satisfying snap as I sheared the last fleshy connection between mother and child.
Zoë wailed mightily. The nurse plopped her onto a stainless steel scale, topped by two infrared heating lamps, like the french fry station at a McDonald’s. Length and weight taken, she used a thick cotton blanket like a tortilla to wrap up Zoë. She put the baby burrito in my arms.
For the first time, Zoë settled, the tight swaddling fooling her into thinking, for a few minutes, that she was back in the warm embrace of a mother’s womb. She looked unbelievably small and frail and unready for a cold, hard world.
Against all odds, YC had invited us to an interview. With a brief email, and a link to a minimalist schedule-appointment tool, the adventure was really afoot.
I had snagged us the last interview spot, on the last interview day—March 29—betting on the usual election-ballot strategy of being either first or last on any list. Thus it was late Sunday afternoon when we nervously appeared at YC HQ, an industrial space in a completely unremarkable part of Mountain View.
With zero ceremony, we were told to proceed into the interview room, where the four YC partners were arranged behind a table like a military board of inquiry. Present was, of course, Paul Graham, along with his wife, Jessica Livingston, also a partner. Jessica had conducted a comprehensive series of interviews of the world’s most successful entrepreneurs for her book Founders at Work, which was a startup anarchist’s cookbook of personal memoir and advice. I had devoured it, and so should you if you want to play in this pond.
Robert Tappan Morris (referred to as RTM by PG) was also present. He was a walking bit of computer science history, having created, in 1988, the world’s first computer virus, which he released and for which he was criminally prosecuted under the then-nascent computer-fraud law. Following his conviction, he joined PG in founding Viaweb, the company whose acquisition jackpot had funded the very venture fund we were pitching. Presently he was a professor of computer science at MIT, but he still participated in YC decisions. PG’s one-line encomium of RTM was as absolute as it was brief: “He’s never wrong.”
Trevor Blackwell was the final and fourth partner, another Viaweb cofounder. He was also the founder of Anybots, a robotics company that actually leased the building we were standing in, and in which YC would become an ever-expanding subtenant. The Anybots labs around the Y Combinator space looked like scenes from the Terminator series, and housed piles of Skynet-like robotic equipment that seemed it might come to life any moment.
“So you want to create the Goldman Sachs of advertising, eh?” PG challenged the moment we walked in.
With that abrupt start, I tried to follow our plan of my speaking for the first thirty seconds to pitch the general idea, and then to proceed to a demo of the hacked-together technology on which we’d spent several sleepless nights.
I was fifteen seconds into it when the questions started.
PG: “How do you join the online click to the physical person in the store?”
Before we could finish an answer, Trevor butted in with a question:
“What do you mean it’s too expensive to buy ads across the US?”
RTM: “How are you going to even scan the products and know what’s for sale?”
PG: “So how do you get paid again?”
And on it went. One of us would try to answer one question, but before we had even gotten started, there came another question, and someone else dove in.
The whole thing devolved into what might have been mistaken for a heated discussion on Israel-Palestine among a bunch of drunks of mixed political persuasions. And the pace never relented. There were two or three overlapping conversations going at once.
While jumping in to answer any hanging question, or to back up one of the boys on a statement, I was keeping an eye on the clock at my left. Oversized, like something you’d see at a sporting event, it counted down relentlessly from ten minutes to zero, all the time we had. Throughout all this, Jessica didn’t say a word, and merely observed us impassively from one flank.
After more wrangling, and with no demo taking place, time was up.
“We’ll talk about it and get back to you today,” pronounced PG finally.
And that was that.
In retrospect, those were the ten most important minutes in my life.
Standing outside, we marinated in the stomach-churning feeling of collective failure. Randomly, we ran into one of the founders of Mixpanel, one of the many successful startups that had graduated from YC and had gone on to great things. YC alums often come to the interviews in an attempt to calm applicants’ nerves, and to provide a better signal in the interview process. The Mixpanel founder did precisely the opposite, attacking our idea, the marketing plan, and the business model.
By the end of these two bouts of abuse, a suicide pact was but a criticism away.
“Fuck it. Let’s go for a beer,” I proposed.
“Yeah, let’s go,” echoed Argyris.
MRM, who curled into a ball when he got upset, opted to go home and be with his kids.
The beer venue was the only decent beer bar in Silicon Valley at the time, a pestilential but cozy cinder block pit that fashioned itself British, with football pennants and Premier League on the screen. The Rose & Crown was popular with the few hip Stanford grad students who hung around Palo Alto, and it fortunately tended to exclude the Abercrombie & Fitch–wearing VC larvae.
Just as a Weihenstephaner hit my hand and I searched for a bench in the narrow beer garden, the phone rang. I didn’t recognize the number.
“This is Paul Graham from YC. We’d like to fund you.”
Shock. Disbelief.
“Ah . . . well . . . so . . . one of the cofounders isn’t here. I should probably ask him first.”
WRONG ANSWER!
Like idiots, we hadn’t decided among ourselves whether we were committed. The boys, MRM especially, weren’t sold on this YC business.
“You need to ask him first?”
“Let me call you back in five minutes.”
One major unpleasantness involved in writing a memoir is the historian’s task of rereading your personal archive of texts, messages, and emails. In contemplating an earlier version of yourself, you’ll realize that young and glorious you was in fact a total and complete fuckwit. An older you, going back and whispering in your young ear, would issue not praise and encouragement, but insults and dire warnings.
I told Argyris the news and cut him off when he asked a question. I had to call MRM.
“Hello?” he answered, with what sounded like a sporting match in the background. His kids were playing soccer.
“Dude, YC wants to fund us. You in?”
It actually took some convincing. If memory serves, I even packaged it as a provisional thing we could back out of, if need be.
Calling back PG, I was horrified to get his voicemail. In as unpanicked a voice as I could manage, I left a message accepting the offer, and followed up with an email to Harjeet Taggar, a former YC founder who was helping manage the interview process.
We were in.
The languorous Sunday-afternoon crowd at Rose & Crown looked on indifferently as I called British Trader to announce the news. We’d not only managed to abandon the sinking ship of Adchemy, we’d flagged down another passing vessel in our mad swim away from that soon-to-be wreck.