The Foursquare you don't know: It hasn't all been Gap ads and nosebleed valuations for Dennis Crowley

By Sarah Lacy , written on October 12, 2012

From The News Desk

Holding up entrepreneurs as heroes is important. Without this hero-worship, people might not take the leap of taking on the near impossible job of creating something out of nothing looking. But that pendulum can swing too far. A lot of publications make it look too easy -- ignoring a company until its "made it" and then writing it up as an overnight success. Worse still is media that celebrates people who are mere fame seekers as "entrepreneurs".

That's one reason I found last nights PandoMonthly with Dennis Crowley so refreshing. In an over two hour conversation, Crowley busted pretty much every preconceived notion you could have about Foursquare.

An easy road? He was turned down by close to 40 investors when raising Foursquare's Series A round of funding. Media darling? For a brief period, yes. But most of Crowley's career has been spent with everyone telling him his idea was stupid and no one wanted it.

All about badges and checkins? That may be the biggest misconception of all.

Last night we wrote about some of the big takeaways from the conversation -- most notably how Foursquare plans to make money. But my favorite bits were the honest glimpses of the struggle. This is the Foursquare you don't see in the Gap ads and the fawning fanboy coverage.

We're going to post the full video from the talk towards the end of the day but here are my two favorite moments from the evening that show the struggle of building Foursquare. If you're thinking of building a company, watch these short clips as a reminder of what you are getting into. If you're in the process of building a company and having a rough day, watch them to remember you're not alone.

First, here's Crowley on the moment Facebook released Places, and he worried his company could be toast. What he did next:

And second, Crowley on the thing he believes that almost no one else in the world believes:

[Image courtesy leWEB12]