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Dennis Crowley and the cycle of second-guessing

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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, Dennis 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.

23 Responses to “Dennis Crowley and the cycle of second-guessing”

  1. pemullen

    Nice post but has little to do with Foursquare, still today one of my favorite and most used mobile apps. Instead it was about the slog of true entrepreneurship and separating pretenders from the real deal. Dennis is clearly among the real deal crowd. I just hope Foursquare somehow stays true to its roots as it tries to find a viable business model. I still use as a digital diary/archive, friend tracker and to track mileage for tax filing.

  2. Cindy Gallop

    ‘Building things that are different, inventing the future and creating a real business is a long and often very lonely slog.’ The team here at couldn’t agree more. Plus, every obstacle a tech entrepreneur with a startup encounters – have a startup aiming to change the world through sex, and you can triple them. Posts like this keep us going.

    Thanks from the lightning bottlers.

  3. Arnold Waldstein

    Thanks for this Om!

    After two decades in start ups, early stage and turnaround, and a bunch of years in consulting to them, I recently started two more and am bootstrapping them.

    Hard work it so is. I do love it. I do love the win. But I don’t glamorize it. Never!

    Have a great weekend!

  4. treetopflyer

    True and genuine entrepreneurs have very little sense of personal “loss aversion.” They are comfortable living with their Spaldings in the vice grip. How many of these fake messiahs have had to watch the repo man haul away the family minivan because they’ve bet it all on a desire and passion to create something from nothing? A true entrepreneur might feel a moment of grief in this scenario, but quickly brushes it off…gives the wife a kiss and let’s her know everything will be ok…and then gets back to moving those boulders. You’ve got to believe it to achieve it.

  5. Nick Rovisa

    You make a very good point early on about enjoying the service and not being afraid to say it. This is what the analysts and opinion-makers need to understand about foursquare – us loyal users really love the product and aren’t afraid to say so. We will stand by @dens and the company for as long as we can because he’s a positive figure in an otherwise mostly cutthroat industry.

    And I know that sort of loyalty doesn’t necessarily impact the bottom line (which is all that seems to matter today), but there aren’t many other services that can tout the sort of community support that foursquare has.

  6. LiangChao

    Dear Malik,
    As an incubator of China, it’s lucky for me to read the encouraging article.
    But i have a question , what exactly make you believe that foursquare is the way of future?
    Would you mind me sending me the answer by email ? You know , Chinese Firewall makes it hard to visit this page.
    My email address is [email protected]
    thanks for your time.

  7. Catheryne Nicholson

    It gave me solace to read this today. Thank-you. As a woman co-founder with two young kids in tow, the silent crying can be deafening. The good thing is the day does end and a new one always begins with a fresh start.

  8. Comment Guy

    “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.”

    Well said Om. One of the best articles I’ve read.

  9. John Dineen

    Great post / read. Its actually so encouraging to read that even for really high profile founders like @dens the grind is just the same as it is for the rest of us. A few weeks back, I had the pleasure of sitting though his interview at SXSW and, along with everyone else, was in awe of the data visualisations that came from foursquare checkins. Fast forward a couple of days and he is knee deep in a spat on Twitter with a VC on the long term viability of @foursquare. Its a roller coaster – that’s for sure!

  10. Albert Lai

    One of the best posts I’ve seen from you yet Om. I wish I could say I’m as awesome and bold as those you’ve listed, but after a half dozen startups now over the past 15 years … much of what you’ve said certainly resonates with me.

  11. Great post, Om! Fending off doubt and criticism and rejection comprises 50% of most entrepreneurial endeavors. Success tends to look obvious in hindsight, but most of the time it was fought for with countless struggles and challenges (and often keep coming despite public praise and glory)

  12. Jeb Ory

    Thank you, Om. The life of a founder is long, hard, and not glamorous. And frequently results in failure. Kudos to you, and people like Sheryl Sandberg and Brad Feld, among many others, in opening the kimono a bit and telling truth to fad.