Pitching Sequoia? Here's the big question you'll need to answer

By Jason Calacanis , written on February 20, 2013

From The News Desk

For the past six years we've held rehearsals for the LAUNCH Festival at Sequoia Capital's offices on Sand Hill Road. Startups from around the country and the world fly in for at least two mandatory rehearsals for the event -- sometimes even three or four rehearsals.

At these rehearsals, Tyler Crowley, my "pitch doctor," and I score the startups based on what we've learned bearing witness from helping launch products like Dropbox, Yammer, FitBit, Mint, Powerset, Red Beacon, Space Monkey, Alltuition (now Brilliant), and Room77. We've coached over 400 startups for our events since 2007. On average, we’ve rehearsed with each company twice, so we're getting close to 1,000 individual rehearsals.

Not only do I lean on my friends from Sequoia to give me their biggest conference room for five or six days a year (ouch!), we raid their commissary like barbarians returning from war.

Most importantly, we drag their partners in to hear these pitches under triple-secret FDA (frienDA). Yep, we get the best venture capitalists in the world to give up full days of their lives to give free advice. We instruct the partners to be brutally honest and hold back nothing, as we want to lance, dress and heal any boils long before it's time to get on stage.

What's the No. 1 question they ask?

What's the theme that I hear over and over again from the smartest minds in venture capital -- the team that literally had more startups IPO this year than most firms have in a lifetime?

"Why now?"

When Sequoia's partners ask startups this simple question, you see gears and wheels turning furiously behind the eye of these promising founders being sent into the arena. They start reflecting on perhaps one of the most important questions in the age of the insta-startup: What has changed that makes this the perfect time for this startup to exist?

Every great startup has a "Why now?" when you think about.

YouTube's “why now?” -- bandwidth costs plummeted, video cameras started recording to digital files, and these new smartphones were coming online with -- wait for it -- built-in cameras AND an Internet connection.

Uber's “Why now?” -- smartphone ubiquity, GPS accuracy, and mobile app reliability. (The first generation of "apps" on platforms like Blackberry and Palm were just not stable and fast enough to do what Uber does).

Twitter's “Why now?” -- everyone had read a blog at MoveableType, Wordpress, or Blogger, and they wanted to get involved in self publishing -- but writing a blog post was too much of a commitment. Writing a headline to a blog (140 characters)? Easy. Twitter couldn't have existed without the blog boom that occurred in the year before it.

Dropbox's “Why now?” -- cheap, on-demand storage and the faster, cheaper, and more reliable broadband in homes and offices.

As for Facebook's "Why now?" I'm actually not sure, since the product was essentially a ten-times faster and better executed iteration of Friendster and MySpace. Perhaps the "Why now?" is that MySpace and Friendster were built on unscalable technologies, and Facebook was "built to scale" -- i.e., stay fast during the flood of virality.

I'm not certain every startup needs to have a killer "Why now?" but it seems like most do.

[Image courtesy of ryanmilani on Flickr]