Dennis Crowley and the cycle of second-guessing


It was a lovely spring day in San Francisco, which is why it made sense for me to meet up with Dennis Crowley, co-founder of Foursquare to catch up on some sun and talk about the 6.0 version of his software. We sat in an atrium, watched the world go by and talked about the new release.

Crowley, who like all founders is running a million miles a minute, took a moment to bask in the glow of positive reviews for the new version of the software. Obviously, not everyone likes it, but as a long-time member of Foursquare, I like the simpler interface that marries discovery, search and check-ins for a glance-able and quick interaction.

There are doubters — actually, there are many who are convinced about the inevitable failure of Foursquare. I am not one of them. I actually like using the service. I am a believer, and I’m not afraid to say it. Because it is indeed the way of the future. Sure, DennisĀ gets spanked publicly for not doing a good job, but that doesn’t mean he is wrong about the marriage of digital and physical.


While some people may have been surprised by this new Foursquare, Crowley and his cohorts have been fairly consistent about their vision of the world and what Foursquare has to do. He and I talked about this three years ago, and it has taken them a long time to get there. There is a ways to go before Dennis can get to his “Harry Potter’s Map” dream.

The positive reviews and the buzz of the new release are going to last a few days, and then it will be back to the grind for him. The grind that consumes all founders completely. The grind that means managing a big company. The grind that means parting ways with your co-founder. The grind that means dealing with constant naysaying, haters and giants who exist to copy your ideas, poach your people and generally make you miserable.

Those of you who have started a company know what I am talking about — the constant, daily upheaval of emotions. There are days when you don’t want to get out of bed, when you whimper without tears and then shake it all off because deep down you know you would rather be doing this than something else. Founders live to capture lightning in the bottle: sometimes it works, sometimes it doesn’t, but we still keep trying. And that is the part the non-builders don’t get.

Building things that are different, inventing the future and creating a real business is a long and often very lonely slog. But you don’t hear about that. Instead what you get is a lot of babble about startups from so-called mentors, advisors and startup gurus. Peel away their sharkskin and you find they have never started a company, and they continue to live in the reflective glory of the company that once employed them. Others are the creation of social media, having struck a pose. And some are born consultants. They find willing listeners among a growing army of entrepreneurs who like enterprenuership as a lifestyle. Sorry guys, entrepreneurship isn’t a lifestyle, it is life.

This spectacle of technology has attracted fake messiahs, and every day I see this mockery of entreprenuership. I overhear it in coffee shops. I am forced to confront it on social media. And I have to remind myself of Pandora founder Tim Westergren, who sacrificed it all to see his bet finally pay off after more than a decade of struggle. I like to think of Aaron Levie, who returns my email at 3:52 a.m. — a minute after I’ve pinged him. And I think of my friend Paul Evans, who has gambled it all on his company, Shareband.

Ask Dennis what it is all about, and he will tell you: seeing someone check into a location, finding a tip and then acting on it.

That moment is what gets you ready for tomorrow — when all hell breaks loose and the second guessing starts all over again.

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