The only thing you got in this world is what you can sell.
—Arthur Miller, Death of a Salesman
AUGUST 26, 2010
Whether justly or no, there are specific events in life during which our characters are weighed and assayed: an all-important entrance exam, the audition in front of the big-shot director, a hard-to-get job interview. Sometimes, we don’t even know the moment is one of those fulcrums on which life hinges: a first date with our future mate, the moments before a debilitating accident.
Y Combinator Demo Day is just such a pivotal event.
You cast your little white ball on the roulette wheel of life, and it comes up either a winner or a loser—and so do you. The best you can hope for, if you’re an underdog outsider like me (and if you’re not, you’ll take it merely as your entitled due), is a place at the biggest roulette table you can find. Well, that much we had achieved, but where our little white ball would stop, we had no idea.
The rules of the Demo Day game were these: Each of the thirty-odd companies in the YC batch had two and a half minutes to present or demo its product and aspiring business to the massed crowd of Silicon Valley venture capital elite. Since Y Combinator’s space was so tiny, the presentations would go in three salvos, each in decreasing order of importance of the attendees (i.e., Sequoia would appear in the first salvo, Comcast Ventures in the last).* The companies would present in a preassigned but random order, the entire demo marathon lasting some two hours, with two breaks in between sessions.
As a sort of practice run and teaser reel, there were two rehearsals of the Demo Day pitches: one to everyone else in the batch, and one to YC alumni, playing stand-ins for the VCs. Many of the alums were investors in their own right, so it was only a partial practice. This would help hammer out the significant bumps in every demo, and alleviate some of the severe stage fright of many YC founders (including this one). Brave in technology and innovation, but perhaps a bit more gun-shy in the more human arts of marketing and self-promotion, YC founders needed a shakedown pass or two before the real moneymen were in the room.
The name “Demo Day” is something of a misnomer; it’s rare to have an actual demo of a product at the event. Given the tight time constraints, it would be almost impossible to walk a potential user (consumer, advertiser, whatever) through any sort of realistic product exposition. Even if you were able to pull it off, most investors were at least as interested in the business side as the tech side, so unless the tech was miraculous, demos were a waste of time.
So the first rehearsal in front of our cohort kicked off.
I had practiced the pitch to the point that I’d be repeating the script in my dreams for years, so go-time was itself uneventful. The AdGrok pitch was simple: Google AdWords represented an immense river of money, much of which was completely undammed or untouched by anybody, as it flowed in its majestic course from the world to Google. We were going to get our hands on a part of it. Even if our take was a small fraction, it would be enough to satisfy the dreams of startup avarice.
By way of entertainment or perhaps to signal quality, the YC management held an anonymous vote among the founders for the best pitch following our rehearsal. AdGrok came in second place, close behind Rapportive, whose polished Prototype Day pitch had so dismayed me. Rather different outcome from me tripping over the cable like Charlie Chaplin, while showing off a nonexistent product, wasn’t it?
In the summer of 1996, I ran with the bulls in Pamplona.
Hemingway oversold the whole thing. For starters, there’s no “running of the bulls.” There’s a citywide festival called San Fermín (after the patron saint of Pamplona), which involves a series of bullfights as an incidental part of the general merriment. In order to transport the fighting bulls from the corral on the edge of town to the bullring, the ever-impractical Spanish decided to simply run them through town. Also in typical Spanish fashion, the local mozos decided to run in front of the galloping bulls to prove their manhood. Fast-forward a few hundred years, and it’s now the Mardi Gras of decadent European youth.
The geometry of the thing works like this: stout wooden barricades, rising higher than you are tall, line the streets of the route. Come eight o’clock that morning, the local police officers clear the route of drunks and tourists, by whack of a baton if necessary. They leave one route of ingress open, close to city hall, for all the potential runners. Then they close the barricades. Anyone left inside is there at the risk of his or her life. For the next ten minutes, nobody will attempt to save you, and in that stretch of rough, cobblestoned street, there is neither God nor law.
I stood there during those ten unforgiving minutes before the release of the bulls. The sensation was one of prickly intensity: life slowed down in that grainy, black-and-white way in which your brain mimics the JFK assassination reels when you’re doing something seriously dicey. Grown men stood with gray, downcast faces, pondering their mortality, perhaps for the first time. Some looked excited for the fray. Others just busied themselves with last-minute prep like stretching that was probably more mental than physical. Soon enough, we heard the hooves clacking on cobblestones and started running for our lives.
You’ll accuse me of embellishment, but waiting outside the Y Combinator space on Demo Day felt the same way. It was an unseasonably hot day, almost 100 degrees Fahrenheit, and YC had set up a makeshift tent to shield us from the sun.
At the run-through we’d made the minor mistake of tipping our hand, and had donned our custom-made ADGROK shirts. By the time the real Demo Day rolled around, every startup had put in rush orders and appeared in logo-branded T-shirts. Since each company chose one background color for its swag, the anxious mob was now composed of two- and three-person cliques, all with color-coded tees: a herd of microgangs composed of unhealthy-looking geeks. People languished about, waiting their demo turn, either alert and reciting their pitch lines, reclining and toying with laptops or phones, or passed out on the floor, anticipating the inevitable.
After waiting our turn, I stood in the “next up” booth, getting wired to a mike by Y Combinator’s CFO, an unflappably chipper Brit named Kirsty. The polite applause for the previous pitch dying down, I took the stage. Cued by whoever was running the laptop, I lit into it like I had just mainlined a handful of cocaine. Screenshots flew by, logos of all the current customers, growth rates, $70 billion market, Google is just the first step—there was even an appropriate amount of laughter at the one half-naked woman we’d snuck in (a lingerie company was using AdGrok to sell fancy bras). It all went as practiced, even better. If the VCs were falling asleep before AdGrok, they sure were awake after. Two and a half minutes later, it was done.
Then, we waited.
These tightly choreographed demos were interspersed with bladder-saving intermissions, during which the startup teams were unleashed on the flower of Silicon Valley capital to pitch their wares. All in all, there were about 150 founders, and at least that many investors in each Demo Day bracket, so during every intermission and for hours after, the space was absolutely nut-to-butt packed.
The mob was a roiling sea of twentysomething geeks in logoed T-shirts and jeans, and rich white guys (and they were almost all rich white guys) in button-down shirts and slacks. All were mingling and talking in and listening in all directions at once, and you literally had to elbow your way past massed twosomes, threesomes, and moresomes as you circulated around. It was a mosh pit of greed and glib persuasion, ambition trading itself for money trading itself (hopefully) for more money in the future. The boys also joined the fray, collecting business cards and names with both hands. It was the most thrilling and terrifying few hours of my life, and the coming weeks and months would be filled with echoes of that chaotic traffic.