Skip to content

The Dreamer’s Disease

by Anthony Bontrager on January 15, 2016

“Wake up kids. We’ve got the dreamer’s disease.”

 – You get what you give, New Radicals



Ahhh… the Dreamer’s Disease.

Almost narcotic-like when you catch it, and while nearly impossible to kick, it isn’t necessarily a bad thing. This “disease” if you will, has given rise to titans such as Microsoft, Apple, Facebook, Google and Uber, along with a host of smaller (but no less important) companies including Zirx, Skift, Elemental Technologies and MediaREDEF.

Having the fortitude to manage the Dreamer’s Disease, however, is what separates winners from those that… well… don’t win.

Case in point. FourSquare recently announced a new and significant round of funding, but one that entailed a much lower valuation than their previous rounds and resulted in its co-founder and CEO Dennis Crowley stepping down from his role.

If you’ve lived under a rock for the past 7 years and don’t know the history of FourSquare, it debuted in 2009 and became one of the most popular tools among early mobile users who would “check in” when visiting a place (i.e. restaurants, shops, cities, airports, etc.) in order to share their location with other people. While Foursquare seemed perfectly positioned to benefit from all the key trends (social, location-based and mobile), the habit of checking into places lost its novelty with consumers, as many of those features were built into other social apps – primarily Facebook.


Rather than throwing in the towel, Dennis and his team reimagined FourSquare, spinning out the core “check in” product into a new platform called Swarm and subsequently launching FourSquare 8.0, which focused on local search and recommendations along with a host of other complimentary features. Given the huge amount of data that FourSquare had amassed since it’s launch, it stood in a very good position coming out of this pivot.

Today FourSquare is, to quote investor Fred Wilson of Union Square Ventures, “surviving and thriving.” While no one ever wants to do a down round, the fact that FourSquare was able to raise $45 million is a testament to Dennis’s tenacity and unwillingness to simply give up on his vision of building the perfect service to connect people to places through their friends.

I’ve met Dennis once or twice – which is to say I don’t truly know him – but I’ve followed FourSquare since its early days and have always been a fan. In my mind, Dennis has managed the “dreamer’s disease” and FourSquare is able to continue on with its mission as a result.

For others out there running their own venture, or getting ready to start one, Dennis serves as an excellent example of never giving up and fighting every day as if it will be the last.

In 2016, as the Series A crunch gets tighter and venture capitalists put their portfolio companies on a forced march to profitability and start sending around slide decks admonishing them to “cut the burn”, this mentality will be more important than ever.

From → -

Comments are closed.


Subscribe via Email to get the latest posts


Subscribe via Email to get the latest posts