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Coffee with Dennis Crowley: 3 Lessons Every Startup Should Learn

There is a reason for influencers names to be staples of our daily vocabularies, whether it’s their genius, their extraordinary experiences or their ability to inspire. Although the Kardashians may not qualify under any of those categories, individuals like Steve Jobs, Thomas Edison and Dennis Crowley most certainly do. From their stories, their experiences and their ideologies we stand to learn so much valuable and applicable information in many spheres of our lives, particularly those of us trying to build something.

Very fortunately, my tech team and I were able to sit down with Dennis Crowley during a recent trip to NYC.

Planning the Trip

I’d been planning to go to the City as soon as the semester was over, knowing that there are many valuable startup resources available, as well as  enthusiastic and knowledgable individuals who could impart some knowledge on my team and give us guidance in building our project. In November I started lobbying various members of the iSchool to give me any sort of contact at the foursquare headquarters, hoping to be able to sit down with some of their developers and maybe in the process be able to say a quick hello and ask a few questions of their co-founder, Dennis Crowley. After going through all the appropriate channels, we were understandably turned down given the hectic time of our arrival (a week before Christmas) and the huge time crunch the office was under. Nevertheless, we had a number of other interesting and valuable meetings lined up and were headed to NYC.

Tweeting @dens

On the way down we decided to send a tweet to Dennis.  It was a shot in the dark, but we figured we had nothing to lose. Here’s how those tweets played out:

We were ecstatic.

Coffee with Crowley

The next day we arrived at the predetermined coffee shop to meet with Dennis. It’s funny how when you have read countless articles and heard someone’s name mentioned in the news so many times, you assume they are going to be larger than life in person as well. Dennis is a very down-to-earth, humble, candid, and extraordinarily bright person who has a way of communicating that makes you feel like he could be an old college buddy. During our talk with him (or should I say our game of 1000+ questions) we were fortunate enough to hear his story, from Dodgeball to foursquare, the current state of foursquare affairs, and a peak into his vision for foursquare’s future. We told jokes, talked coding languages, discussed privacy and transparency issues, chatted about market competition, and shared hysterical Syracuse University stories.  Here are the three most important things Dennis taught us:

Lessons Every Startup Should Learn

1.Transparency Matters

As we put more and more information about ourselves, our families, and our friends on the internet and trust social platforms with intensely personal data, transparency matters. Twitter and foursquare have 100% transparent APIs, which does two things: 1) it builds a relationship of trust between the users and the company and, 2) it opens the door for people to build some awesomely brilliant products on your platform.

2. If the technology to build your product in your vision isn’t there yet, build it as close as you can so you are ready when it is.

Technology moves fast, but not always as fast as our imaginations. One of the things Dennis emphasized in our discussion was, cater to your vision, the technology will be there someday, and when it is, you will be ready for it. This was very much a part of the evolution of his idea from Dodgeball to foursquare and on to foursquare’s Radar feature.

3. Build first, politics later.

Roll your sleeves up, get messy in code or whatever you are building. Find like-minded people and build together. Worry about the incorporation, the equity, the market and whatever else may be involved in the ‘business’ end later. The building is the most important part.

So there you have it. Have an idea? Get building, dive right in and stay true to your vision because the journey is just as exciting as the result.

I’d like to say a very special thank you to Dennis Crowley for taking time out of his Sunday to sit down with us and for allowing us to be the sponges that we were and absorb as much as we could.

Have a question or comment for Isaac?  Share below or tweet Isaac at @ibudmen.

Isaac Budmen

Comfortable foot attire enthusiast -- more to read at TeamBudmen.com

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  • A classic story of upstate New York HUSTLE taking place in the greatest city on earth. Having met Dennis in person very briefly myself, I can vouch for that too – not even a HINT of deucheness at all, the guy is simply as genuine and real and as you said ‘down to earth’ as anyone I’ve met who’s had the notoriety and success that Dennis has. 

    I’ve heard many people in NYC say that Dennis’ personality personifies the foursquare brand, and Chrysanthe their community manager says he’s the best community manager on their team. Really sick you guys got to meet him. 

    Glad to meet with yall btw. Good luck on your journey. Definitely get school graduated and alla that, build up ‘dem tech skills, don’t stop the around the clock grind, etc. Holla anytime. – John X 

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  • Anonymous

    Awesome story Isaac. I like how you’re all about the “do”. It really can’t be overemphasized enough.