Dennis Crowley and the cycle of second-guessing

23 thoughts on “Dennis Crowley and the cycle of second-guessing”

  1. 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.

  2. 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)

  3. 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.

  4. 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!

  5. “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.

  6. 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.

  7. 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 directive.lc@gmail.com
    thanks for your time.

  8. 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.

  9. 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.

  10. 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!

  11. ‘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 https://makelovenotporn.tv/ 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.

  12. 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.

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