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May 16, 2006

Last week, I returned to the Time 100 dinner at Lincoln Center in New York City thanks to the generosity of Jim Kelly and the folks at Time. The dinner puts words to shame; the only one with a fighting chance is: surreal.

The evening begins with a red carpet that whisks you off Columbus Circle into Lincoln Center and up an elevator to the palatial jazz room overlooking the city. Crowds line the carpet and scan ravenously for prey they recognize. And were it any other day, I’d have been right there alongside them, trying to bottle a genuine droplet of Jon Stewart sweat, asking Oprah to sign my chest or Condoleezza to sign my declaration of war.

When my turn came, the shouts were deafening: “Will! WILL!” Initially I assumed they were asking me for something—”WILL you marry me?” WILL you have my child?”—but in hindsight they were probably shouting at Will Smith, who was behind me, or perhaps “WILL you get out of the way so we can see Will Smith�” Of course, I didn’t have the benefit of hindsight. That’s the first rule of red carpet walking: always look straight ahead. Keep your cool, and pretend that you actually belong one step ahead of the guy you idolized on television every school day for six years.

I’ve spent the last two trying to make sense of the whirlwind absurdity that has become my life. Dinner with the Fresh Prince on Monday, coding object serialization on Tuesday, venture capital strategizing on Wednesday, Belgian interview on Thursday—dorm meeting on Friday. It has been exhilarating, intoxicating, exhausting and overwhelming. Most of all, it has been undeserved.

But things are what they are, and when life gives a stage, it also gives a choice: ride the red carpet, savor the wine and strike a pose. Or take the stage and make the biggest damn impact you can until the curtain falls. And that’s why I’m taking time off from Stanford, and that’s what this startup is about. I don’t know whether it will succeed or fail, but I will know that when the fates called my name, at least I stood up.

Twenty-four hours before leading Will Smith into a black tie dinner hosted by Paul Simon, toasted by Katie Couric and roasted by Stephen Colbert, with filet mignon and a glass of J-Lo, I straggled into the Men’s Wearhouse on 46th to upgrade my tomato-stained jeans to my 48-hour tuxedo rental. And when she gave it to me, the lady cocked her head, smiled wistfully and unwittingly nailed the last 552 days of incongruous lunacy far better than I ever could.

“Prom?”