By: Hillel Fuld 

I recently tweeted this question. Out of the tens of responses I got to the question “What services do you use daily” almost half of them included Foursquare, along with Gmail, Facebook, and Twitter. If you are not familiar with Foursquare, it is the undisputed king of location-based services. The concept is simple. You “check in” to locations and let your friends across the Web know where you are.

Now, here is the thing with Foursquare. Over the years, there have been many apps/services that I, and many others swore “I would never use that. Why would I use that? Why would I feel a need to share my location at every given moment”? Now, two years later, I use Foursquare every single day. I cannot put my finger on it, but something about location mixed with gamification and the cool thing to do has me checking in to work and other places every day. I am not alone and Foursquare has well over 10 million users. Think about that number. It is truly remarkable.

Foursquare, in my opinion, should be a model that inspires entrepreneurs across the globe. The reason I say this is because the service has overcome all the challenges startups face from the initial pitch, which I am sure was not a trivial thing in Foursquare’s case, to traction to mass market, monetization, and eventually making it to the top and killing off all competition of any kind. If Foursquare can do it, anyone can.

I have been trying to interview Dennis Crowley, Co Founder of Foursquare, for over a year, but as you will see from his answers (especially the first one), the man has zero extra time. Thanks to my persistence (ie nudging the crap out of him), I finally woke up to Dennis’s answers in my inbox. You can also read more about Dennis here and see how he lives his life here.

As you will see, Dennis did not just answer the questions to get the interview over with, he clearly dedicated time and thought to what he was saying and for that, I thank him.

The man is a true tech legend and I cannot thank him enough for this opportunity. Entrupeneuers, pay close attention to Dennis’s answers below:

1: Please tell us a little bit about yourself, your background and how you got to where you are today, professionally and personally.

Long story short:  from Medway, MA, went to Syracuse for undergrad (Communications major), moved to NYC, my first gig was as a research firm called Jupiter Research, started tinkering w/ code & building cityguide stuff while at Jupiter, dodgeball 1.0 (cityguide) was eventually born from nights and weekends of teaching myself how to code ASP out of a book, used dodgeball to parlay myself into a gig at Vindigo (Palm Pilot cityguide), got laid off in dot-com crash.

Went back to hacking on dodgeball and dodgeball 2.0 (friend finder) was born, 9/11 happened, moved out of the city, took a job as a snowboard instructor (Attitash, NH), applied to grad schools, moved back to NYC in the fall, started at NYU / ITP, met Alex, worked together on a bunch of projects (one of which became our thesis: dodgeball 3.0), graduated, gave ourselves 6 months to make something happen with dodgeball.

12 months later we were acquired by Google (where I met Harry), spent 2 years at The Goog before going to work at a buddy’s games-that-touch-the-real-world startup called area/code (where I met Naveen, he shared office space), left area/code after about a year and went traveling for a bit (Thailand, Scandinavia), got bit with the “croudsourced city guide” bug, came back to NYC and teamed up w/ Naveen to start hacking on projects to “make cities easier to use”, Google announced they were shutting down dodgeball (Jan 09), Naveen and I picked the SXSW festival in Austin to launch something new, we hustled, launched it… and here we are 2.5 years later.

2: A crowd sourced question for you (from @hamutalm of @dapsem): “As I see it, 4SQ is paving the way to a whole new world of biz models, ours included. did you envision that? Where do you see it going?”

 We didn’t really anticipate any of this. foursquare started as a replacement for dodgeball…  something for our few hundred friends to use after Google was going to shut down the service.  I remember when we were try to raise our first round of funding, someone asked me when we thought we’d hit 1,000,000 users and I remember thinking, “1 million users?  that’s crazytalk”.

Fast forward to 10m+ users later… because we’ve been thinking about this space for, what?, almost 10 years, we have a very strong and clear sense of what we want to do / the problems we want to solve / what the product should look like 12 or 18 or 24 months from now.  We never expected any of this to happen, but now that we’re in the middle of it, we know exactly where to go.

Without tipping our hat too much, what you see in foursquare now is just the beginning.  We’re building things that encourage people to go out and explore, that help connect people to places (and places to people).  I’m writing this from the Global Hackathon we’re hosting in NYC and I’m surrounded by 100 developers building on top of our API – they’re creating everything from tools for merchants, to real-time neighborhood heat maps, to networked jukeboxes where the person with the most checkins has more say over the playlist. It’s really incredible to watch.

3: There are certain words we hear over and over again among new startup founders, one being “We are the Foursquare of…” How do you explain this virality?

A few weeks ago, Caterina Fake (Flickr co-founder) wrote a great post on how she’s been by inspired “the stuff that people make”.  I’m the same way — video games, baseball cards, websites, startups, grad school projects, etc. have all inspired the things you see in foursquare:

http://dpstyles.tumblr.com/post/9754026763/people-ask-me-who-inspires-me-this-often-stumps

… anyway, the “foursquare of XYZ” stuff is just that, people being inspired by us in the same way we’ve been inspired by others.  It’s a great feeling to build something that inspires other people to get out there and build too.

As for the virality of it all?  Not really sure how to explain it except for we love what we’re doing, we love what we’re building.  And I think people can see that in our products and our team.

4: Let’s talk about mobile app discovery. With 500,000 approved iOS apps, how do you recommend a developer stand out?

Build something awesome.  Sounds hokey, but if you sit around and think “hmm… what can i build that will just kill it in the app store” you prob won’t get far.  But if you start from “hey, i think i can make my life a little better / easier / more interesting if i can build this thing that does XYZ” then there’s a good chance that the thing you want to use so bad that you’re willing to build it yourself will also be interesting to other people.

5: What are three trends we will see grow in the mobile ecosystem throughout 2012-2015?

How about just the big one:  mass understanding of the idea of “phone as networked sensors” – something you carry in your pocket that let’s you know about all the interesting things going on nearby.  I think the idea of “hey, let me take the phone out of my pocket at ask it a question” is going to be augmented / replaced with the idea of “my phone knows what’s going on around me and buzzes to let me know about the best stuff w/out me even having to ask”

6: About app monetization, clearly 4SQ is unique on this front, but what model do you believe is most effective for an independent developer: Paid download, in app advertising, in-app purchases, or something else?

Eh, it depends on what you’re trying to do.  If you’re making something social that requires virality and millions of *everyday users*, its prob not the best idea to charge people a buck a download.  But if you’re making a service that *businesses* can’t live without, it probably makes sense to charge them a few bucks a month to use it.

Clive Thompson wrote a great piece in the latest issue of Wired that flirted with a lot of these issues:

http://www.wired.com/magazine/2011/08/st_thompson_onlineads/

Definitely worth a read.

7: So it seems your competitors Gowalla and even Facebook have admitted defeat, is there really no room in the checkin space for more than one player? Why did they quit?

I generally think there seems to be one dominant player for each “big idea” on the web.  Google owns search + maps + email.  Facebook owns “sharing with friends” (especially photos).  Twitter is shaping up to own real-time news discovery, stream of consciousness updates from friends / celebrities.  And foursquare is carving out the relationship between people and places – “what does it mean for me to be at this latitude/longitude right now / in the future / in the past”

This all starts w/ the checkin – but as I can see right now from everything being built at the NYC Hackathon – bleeds into all the *data that comes from* the checkin…. who’s where now, who’s been where, who knows what about Paris, who knows the most about coffee shops of downtown NYC, what’s the one thing I shouldn’t miss while I’m in Brattleboro, VT.  We’re getting very good at answering these types of questions.  And that’s going to be the thing we do better than anyone else.

8: Foursquare is available across multiple platforms, what are your conclusions about the different mobile OSs in terms of development, discovery, and overall user experience? Please include iOS, Android, BlackBerry, Nokia, and Windows Phone 7 if possible…

Well, we only maintain the iOS, Android and BB versions of the app in house.  The other versions (Nokia, Win7, WebOS) are built on our API by either our partners or the developer community.  App development is tricky and we have a great team of developers contentiously working to make our products great. 

A majority of our users are on iPhone though Android is catching up quickly.  Meanwhile BlackBerry is a huge platform for us outside the US (esp in Southeast Asia).

9: What are three of the most important tips you could give to a beginning entrepreneur in the tech space?

a.  Don’t let people tell you your ideas are stupid or don’t work.  Find a way to build a prototype and find out for yourself.   In the process, you’ll probably find a way to make your ideas work.

b. Don’t sit on good ideas because you don’t know how to code or don’t have a technical co-founder.  Either go find one or pick up a book.  I didn’t study programming or engineering.  I write really ugly, sloppy code, but you know what, its good enough for prototypes and it’s good enough to get the point across.   Something that works is better than nothing that works.

c.  Don’t sit on your prototypes, launch them.  The only reason foursquare launched is because we picked SXSW as a due-date (just like you’d have a due date for a term paper in college).  We could have worked on it for another 6 months and we still wouldn’t have felt it was “ready” for launch.  Letting your rough work go and getting it out there for people to play with is sometimes the hardest part, and it’ll be easier to do if you set your sights on a deadline.

10: Another crowd sourced one for you. (From Jon Burg of Digitas):”Please share some insight into your user lifecylce. What percentage of your users stick with your service, why do some leave and what is Foursquare doing abt it?

Well we have more than 10m users, we’re seeing well over 3m checkins per day and the average user is checking in 2-3x a day.  There’s now more than a billion checkins in our database (!!) that are being used to power our “Explore” recommendation engine.  That’s a big deal.  🙂

I think one of the most interesting trends we’re seeing is usage of foursquare by people who don’t check in…  these are folks who are using the app just to check the tips at the places they go, figure out where to go using the Explore tab or take a look at what their friends are up to.

We’ve been starting to shift our thinking about checkins to the way that Twitter thinks about tweets.  Originally Twitter’s most important metric was the number of people who were actively tweeting — these days they’re more focused on the number of people who are *consuming those tweets*.

Same applies to foursquare checkins:  3m+ checkins per day is an impressive number, but every day those 3 million checkins are being consumed by more and more people… people who are using our apps to find their way around new cities and familiar neighborhoods.  The number of checkins per day is always going to grow, but the number of people who are *benefitting* from all this checkin data (searching, “explore”, tips, etc) is starting to increase at very rapid pace.

Anyway, hope all this is helpful to your readers!

Dennis, thanks again for this, I think I speak on behalf of my readers when I say that your answers definitely shed some light on a lot of important topics. Appreciate your time and all I can say is, keep on rocking!