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Pseudorandomness, Or How I Got Into Y Combinator and Had a Child With a Woman I Barely Knew, Almost Simultaneously

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Forms, forms, everywhere are forms

Filling out an online form can change your life.

I filled out two such forms. One was an online dating profile at Match.com around June 2009. The second was the application to Y Combinator in February 20101. Little did I know then how these two forms would guiltily conspire to change everything.

Guitar Strings in Half Moon Bay [ February 21, 2010 | 10:36 AM]2

Sunday morning phone calls often have far-reaching implications. Anything that interrupts a matinal sabbath repose is bound to stir things up.

It was Matt McEachen calling about guitar strings, and his inability to find any in the small ocean-side village he resided in. We start an idea katamari3 and roll it everywhere, picking up just about every piece of local search, social media, marketing and technology we know about. The end result is a crazy scheme to turn local shopping on its head by joining backend inventory control (think small-business Quickbooks) with front-end Web shopping databases (like Google shopping).

Our ball of ideas grows bigger than us, and rapidly gets its own momentum. Our startup baby needs a midwife. We’re filling out an application to Y Combinator the day before the deadline. My co-founders are unconvinced as to the wisdom of this. We had real jobs. The money on offer was paltry. The equity taken was large. The idea so vague and ill-formed it might just vanish like smoke in a breeze.

I’m a sucker for a fine prose style, so I print out and give a copy of this essay to both. That essay is the gateway drug of startups, it is entrepreneurship crack and meth rolled into one4. The co-founders are convinced. We submit the written portion of the application.

Love on the installment plan [ June 5, 2009 ]

Match.com conversation turns into a first date.

First date followed by a random run-in at the boatyard. Her ex-boyfriend is there too, and we make friends.

Random run-in turns into a dumping. It's too weird I know her ex-boyfriend.

Dumping turns into ambiguous opera outing with date and her friend.

Opera outing followed by brunch at her place.

Brunch leads to dinner.

Dinner leads to a pornographic scene on her kitchen counter.

Mayhem breeds more mayhem.

And now she's pregnant.

Present at the creation [ February 17, 2010 | 1145 PM ]

All that remained was a one-minute video presenting ourselves and what we wanted to do5. I was in the initial throes of a Joaquin Phoenix-esque descent into anti-social malaise, whose principal expression was the growth of a truly Fidel Castro-sized beard. The thought did occur that I might look like an uncouth barbarian. Screw it, YC would get me beard and all.

As in almost every YC activity, the challenge with the video was to distill down a lot of complex stuff to impossibly short time constraints6. By 11:50 PM I had it down to a minute and ten seconds. I go to email it to Posterous7 to discover Gmail has a 30GB email limit. More editing, at lower resolution, and by 12:30 we have a video (deadline was at midnight). A miss is as good as a mile.

ESPN, Maxim, and a No. 2 hair clipper. [March 6, 2010 | 11:34 AM ]

The Razor’s Edge in Alameda is a wormhole in spacetime to the American 1950s. Girlie mags on the racks, ESPN on the TV, and an old, crusty barber who’ll crack racist jokes or discuss auto repair with equal panache.

I tell him to do something interesting with my Yeti’s beard, and he sets to work with razor and scissor. He fancies me a thick goatee and thin moustache. I look like I just got released from either San Quentin or trucker’s school.

Si quieres hacer reír a Dios, cuéntale tus planes8 [ March 7, 2010 | 8:35 PM]

If you had been standing on the corner of Broadway and MacArthur 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, to support herself as they struggled across the last couple hundred feet. Every twenty feet 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, keep in tow a large hastily-packed 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 37 weeks pregnant.

We had known each other for 39 weeks.

James Brown and Mr. Limpy [March 21, 2010 | 4:00 PM ]

Two hours before we’re due in Mountain View, over thirty miles away, we decide to do our first end-to-end test of the system, entering a UPC code, extracting product information, and generating a product page. Our test product thus far had been Mr. Limpy, an imposingly large rubber phallus, the sort of gag gift you buy for a bachelorette party (or God knows what), and it had worked astonishingly well so far. That wouldn’t do for the Y Combinator pitch for obvious reasons.

Argyris is an indie-music junkie, and was still anchoring an evening spot at KZSU, Stanford’s student radio station. I start rifling through one of his mountains of CDs and trying them one by one. No dice. They’re all weird, niche bands even Amazon hasn’t ever heard of. I flip quickly through the entire pile, trying to find the most mainstream thing imaginable. James Brown’s ‘In the Jungle Groove’ flashes by, and I try it. Amazon recognizes it, and returns a cover photo and product description. We’re golden.

I carefully make sure no user has Mr. Limpy9 in their product database, and we pile into Argyris’ VW beetle for the drive down to Mountain View. Along the way, I pull out, what else?, the James Brown CD and we listen to ‘Sex Machine’ as we barrel along the 101. Argyris and I agree that if we get funded, we’re declaring the Godfather of Soul our official patron saint. St. James of Augusta would see our company through.

Mucosal plug10 [ March 7, 2010 | 9:30 PM ]

Amanda passed out on a gurney and began bleeding profusely. 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 milestones of birthing are measured in centimeters. Seven centimeters dilated; too late for anesthesia, too late for fashionable breathing exercises. It was show time.

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 difference between the bloody, screaming tableau before me and that of, say, my grandmother’s birth a century ago in rural northern Spain, by candlelight, in some country home, 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 south11.

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 Mad Men-esque bouts of nostalgia for an unknown time when men simply paced nervously and smoked in some other room while the dirty business was done elsewhere. 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, and a sort of pus-like 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 on 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 and wrapped 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.

Shake your moneymaker [March 21, 2010 | 3:45 PM ]

So there I was looking like Captain Morgan12 with Argyris and Matthew and the partners of YC. There was a large and official-looking clock, like something you see poolside at the Olympic swimming competition, to the left of the desk by Jessica. It read "10:00" and started counting down immediately.

Paul Graham demolished immediately whatever premise we had of a demo script by greeting us with my application sound bite: “so, you’re creating the Charles Schwab of local product marketing…” What followed was a meandering rough-and-tumble debate about local search. Trevor would chime in with a tough question, McEachen would begin to respond, but not before Paul jumped in with another, which Argyris would field. I would chip in on one of the going threads, but not before another one started. It was all over much too soon.

We came out of the demo and, to a man, thought we had completely blown it. We were heartened somewhat when Paul Graham chased us out the door to ask us a follow-up question, then immediately disheartened again when we pitched the idea to a YC alum who was milling about13. We decided to go to the Rose and Crown in Palo Alto to drown the worries.

Before we had managed to order the first round, we had a phone call from Paul Graham offering to back us, which we accepted after a bit of discussion14.

Back at home that night, after all the excitement, Zoë slept in her cocoon of blankets, and took no notice of the idea that had just been birthed alongside of her.

  1. The two applications aren’t unrelated, even in content. One of the Y Combinator questions asked you to name one non-computer system that you’d hacked in some interesting way. My answer concerned a man-in-the-middle attack I once did on Craigslist personals. I placed an ad as a woman seeking a man, and as a man seeking a woman, and then simply crossed the email streams by forwarding mail from one to the other, and vice versa. Most Craigslist personals didn’t even have photos back then, so the switch went undetected, even after the couples had met. I handed off the relationship by telling one that the other’s email address had changed, from my fake one to the real one, and likewise vice versa. For all I know, those couples are still together and having kids. They probably don’t know to this day what happened or what brought them together. []
  2. The date and time are my lame way of juxtaposing two convoluted processes which evolved on different time scales, but culminated around the same time. Another way to think about these is like the computerized timestamp that adorns the first few seconds of a cutaway scene in every Jason Borne or Tom Clancy film ever made. You know, “Cairo: 0345 GMT”, in the lower right hand corner, in green monochrome typeset, complete with beep-y computer noises. []
  3. If the concept is foreign to you, check out this. It’s basically a massive ball of disparate stuff. The Japanese invented a quirky and strangely addictive video game of the same name, in which you roll this ball all over the earth. The end result is you have this immense, lurching ball, with everything from cows to a tractor sucked into it, being rolled over hill and dale. You have to see it to understand it. Being slightly drunk helps. []
  4. For more fine startup erotica, check out Jessica Livingston’s Founders at Work. Paul Graham’s chapter is especially good. []
  5. Don’t do as we did and wing it. PG has said more than once that if there was one thing in the application he would keep at the expense of everything else, it’s the video. So get it right. []
  6. The final climactic demo is now down to two and a half minutes. 2.5 minutes! I couldn’t really explain how a salt shaker works in that time, much less how we’ve built the future of online marketing. Tough. Get used to it, entrepreneur. Everyone else is in the same jam. []
  7. Another YC quirk: any piece of YC administrative or technical machinery will use a YC company’s product, if possible. It’s a product patriotism verging on extremism. The day PG funds an airline startup, you can be sure that’s the only thing he’ll ever fly again, and he’ll expect you to do the same. I fully expect PG to use AdGrok if he ever advertises anything. []
  8. A Mexican proverb which translates as: if you want to make God laugh, tell him your plans. The Old Bugger must have had a chuckle over this one. []
  9. To be fair, I’m probably guilty of introducing Mr. Limpy into the AdGrok memepool. The idea was a sort of negative reinforcement anti-prize: if you broke the code build, or did something amusingly and uniquely stupid, you’d win the Limpy Prize for that week. Ideally, the prize would be gifted in a Godfather-esque scene, whereby the guilty hacker would suddenly find a disembodied phallus inside a drawer or under some papers on their desk, and they’d clutch at it madly while screaming at the top of their lungs. The reality of course was that we each would have earned a Limpy prize four or five times over during those early days of development. []
  10. You don’t want to know what that is. Really. []
  11. The oil was a lubricant to get the head through at the final moment, when it looked like the birth was really hitting the apex of improbability. []
  12. The ‘Captain Morgan’ was the moniker bestowed by Paul on our first official meeting, once YC started. Evidently, he expected me to keep that ridiculous piece of facial hair. The disappointment with which its disappearance was met made us all kind of think that the crazy goatee might have been why he funded us. This is the same meeting where he talked us out of the idea he we pitched at the demo. AdGrok, in current form, is actually plan ‘J’. []
  13. YC alums typically hang around on pitch day, to put aspiring YCers through their paces and give them some advice on their pitches. The idea is to quiet anxieties. This one, intentionally or no, did exactly the opposite. []
  14. Note, Paul kind of expects an answer immediately, and our hemming and hawing was in poor form. So make up your minds beforehand []