[continued from chapter 1] …so we had a concept for a ‘build your own craigslist’ that was going to take over the world. After talking through the concept in detail with a few trusted friends and advisors, there was only one thing left to do: build something.

September 1 rolled around and the news broke that TechStars was coming to NYC.  ”eh? eh?” Benny prodded.

We decided to apply to both TechStars and Y Combinator. We were able to score an interview with Y Combinator and threw together a rough Friendslist prototype to demonstrate messaging and basic functionality.  Then we did a ridiculous thing…

We flew across the entire country for a 10 minute meeting.

The barrage of questions began as soon as we sat down. “So you’re building a build your own marketplace.  Who is this for?” asked Paul Graham. Benny explained that it’s designed for connectors.  ”What makes you think anyone will want to use this?” shot back Paul.

Our YC alum friends had given us lots of advice and warnings: “Just hold on as best you can.  Stop the train from getting entirely derailed.”

It was an impossible task. In a room with six people (Paul Graham, Jessica Livingston, Paul Buchheit, Robert Morris, Trevor Blackwell, and Harjeet Taggar), there seemed to be at least ten lines of thought. Our pitch quickly got derailed around email. “Why can’t you just use an email mailing list to do this?” Benny replied “well you can’t browse it in an easy way”  ”Of course you can.”

Finally Paul Graham, who seemed utterly confused asked bluntly “Where did this idea come from!?”  I offered my personal  anecdote:  “A LOT of people come to me looking for stuff — jobs, apartments, etc.  I wanted a place to put this.  I started Wegslist.”

Paul finally got it!  ”Ohhhhh, you’re one of these connectors.”  And then the meeting slipped back into confusion and objections. Paul Buchheit didn’t understand why it’s better than email.  Trevor didn’t understand why it’s better than a Google group.  Harj was concerned about how we would get liquidity in the marketplace.

Paul pushed us to consider whether a the Hacker News community (or a Porsche website) could use this to power a classifieds site.  We gave in a bit and said “We’re not committed to centering this around a person, but it’s going to be our first approach.  I think there are a few different ways this can go: 1) It becomes a craigslist competitor at scale 2) it becomes best of class platform (like stackoverflow) that you license to people or companies 3) We pick a vertical and kill it — jobs, apts, or roommmates

Finally Paul asked “Benny, you work at Gilt Groupe.  Why not do something in the daily deal space?” “That space doesn’t interest me that much.”

Paul followed up: “What’s your guys’ expertise?” Me: “Mobile. [long pause] I’m not going to sit here and tell you there’s some trajectory between exit strategy and this project. But this is something we’re passionate about and want to try.”

The group gathered around our laptop to look at the rough Friendslist prototype “That guy look like he’s about to be attacked by a mob surrounding him.” “That’s a really scary logo!” “You guys aren’t graphic designers, but that’s exactly the right messaging.”  The timer went off and the 10 minutes was up.  We filed out of the room speechless.

Benny was the first to break the silence.
“I thought that went pretty well.”

“Are you kidding? We just got crucified”

[continue to the next chapter]

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• FriendsList is dead (but we’re very much alive!)
• Idea, team, or network?
• DoubleDub: A Dream Come True
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• Location, Location, Location: The Hyperlocal ‘Moment’ of Awe