A Foursquare Graduation: Jeremy Arnon's Interview with Tristan Walker

My brother, Jeremy Arnon (@jeremyarnon), recently interviewed Tristan Walker, who serves as VP of Business Development at the uber-popular startup Foursquare. Below is Jeremy's interview.

Business school is a grind, especially at a top-tier school such as Stanford. When I first met Tristan, I was shocked to learn that he is still a full-time student. Graduating from business school this May, he's been pulling double duty during his final two semesters, all the while locking down partnerships with notable brands such as Pepsi, Bravo and MTV.

Out of sheer interest to learn just what he was thinking in taking on such a heavy load, I decided to sit down with Tristan to ask why he decided to make the rest of us feel like lazy bums for working just one demanding job! Not that Foursquare needs any more free press, but here's my conversation with him:

Jeremy Arnon (@jeremyarnon): Tristan, the story here is two-fold. One, that you have been able to work a demanding full-time job while also going to business school full-time at Stanford University and somehow pull it off. And two, that you've been able to navigate your way into this and other opportunities with no significant connections to speak of, a testament to perseverance and a lesson to students to say don't sit back and wait for things to come to you, go out and make them happen on your own.

To provide some context, let's talk about how you positioned yourself in your first year to make this opportunity possible. Most business school students are lucky if they get a shot to work for a cool start-up once during their school years. You've had a chance to do it twice, starting with your internship at Twitter and now at Foursquare. Can you describe what your Twitter experience was like and how that came about?

Tristan Walker (@tristanwalker): Around Christmas 2008, I was sitting at home and decided I wanted to learn about all this tech stuff. So I said I'm going to sign up for a Twitter account today, I'm going to check out about 10 blogs and start reading them everyday. I wanted to be immersed in the Valley and teach myself as much as I could.

So I signed up that day and immediately got enamored with the Twitter service. I just thought that they were doing something very, very important. You think of all the great companies and a lot of them are really defined with one word. Facebook you think identity, Google information, and I felt that Twitter had an opportunity to really own communication and I really wanted to be a part of that.

So I got back to school and met up with my alumni mentor and told him that I had something going on for the summer but I really wanted to do something entrepreneurial, to which he was very supportive. So that night I got home and e-mailed some top Twitter executives just to try, I figured I wouldn't get a reply but wanted to see if anything would come of it.

@jeremyarnon: Now, is this just a cold e-mail or did you have an existing connection?

@tristanwalker: No. In fact, it took a lot more time to finally make contact with them. After that initial e-mail, I reached out to about 20 different VC's that I thought might have an in with the company. Number 21 happened to be David Hornik who is now a great friend and mentor of mine. He asked if I had any ideas and whether I'd be willing to work for free. I said yes to both, explained my ideas, and he decided to make an introduction for me.

A couple days later, I got an e-mail back from Twitter saying they were interested in meeting. I proposed three ideas, two of which they were thinking about but didn't have the resources or bandwidth for. I was willing to do it for free so they let me do it. I worked with their Product Manager and four months later we had what turned out to be Twitter 101 for Business. I helped develop a bunch of the case studies on the site that are meant to help businesses learn what other businesses are doing to leverage the platform in interesting ways.

@jeremyarnon: Very cool. I like that you weren't afraid to reach out without any existing connections. So, I assume with the Twitter connections you rolled that into meeting the folks at Foursquare?

@tristanwalker: No, last summer ('09) I had an opportunity to intern for a large consumer retailer, a position I had lined up at the beginning of school. It actually taught me a lot about how retailers do business and has provided a lot of insight that is very useful for me today. I wanted to do something sort of at the intersection between the way that companies are leveraging social media with platforms like Twitter and the way that brick and mortar companies work. I had no idea what that would be, whether it's payments or some kind of social commerce, I just knew I wanted to play in that space.

And then I saw a headline about Foursquare back last July and immediately it hit me right away. This was the first time ever that people would be able to measure live foot traffic into their venues and I knew how valuable that information could be for merchants, retailers, etc. I am fascinated by payments and I realize that where you can extract the most value is at the point of sale. So I wanted to align myself to get as close to the point of sale as possible and I felt that Foursquare had the opportunity to do that before anyone else could.

So, I e-mailed Dennis (Crowley). I e-mailed him about ten times before he responded. He finally got back to me, said he was happy to chat and asked if I was ever going to be in NY. Of course I said yes, went and bought my ticket that night, flew out to NY and we hit it off. Pushed some of my ideas, he dug it, and a month later I was helping to run Business Development for the company.

@jeremyarnon: So when you started with them you had two semesters left?

@tristanwalker: I had a full year of school left, three quarters (we're on a quarter system).

@jeremyarnon: So, the first question is, why did you decide that you wanted to do something full-time even as a full-time student?

@tristanwalker: I guess because I had the opportunity to. You know, I felt it would be hard but it was something I would be totally passionate about. It really goes back to setting your priorities. The business school has really prepared me for an opportunity like this. I said, here's my lone opportunity, let me leverage it before someone else does. So I wanted to grasp that and not let it go.

Like Twitter, I was just so inspired by what these guys were doing. It was just Dennis and Naveen at the time, they had just hired Harry, and I was already an admirer of what Dennis did with Dodgeball and the product there.

Certainly, this has all come with a sacrifice. There are three things you can do at business school: social, academic and professional, and you can only do two well at one time. I've certainly sacrificed one of those and have been really focused on professional and academic.

@jeremyarnon: Was there ever a time when you thought about taking a leave of absence from school?

@tristanwalker: Well, you know, that always goes through people's heads. But, I didn't have to. I was able to handle all the work. So I said, if I can handle all of this, let me continue it. Let me be a story for folks to say, hey, you can do the school thing and the startup thing at the same time. It's not ideal, definitely comes at a large sacrifice, but for me it was doable.

So, certainly, I'd lying if it didn't cross my mind, but, you know. I wasn't getting to let that happen because I was so close. Plus, I have a wife and I owe it to her to finish these things having brought her across the country (for school) and I wasn't going to let that happen. And I was also pretty upfront with Dennis. I said, I have school, but I'm going to bust my ass and I'll be full-time and you'll have nothing to worry about it. And I think he trusted me from there.

@jeremyarnon: When do you graduate?

@tristanwalker: Hopefully June (with laughter).

@jeremyarnon: Most people will say about business school that the academic piece is important but the actual grades aren't that important. Have you seen your performance dip in any area as a result of taking on so much?

@tristanwalker: My performance has been fine. Yeah, that's something I certainly feared but it's been OK. We'll see what happens this quarter (with laughter). But I should be OK.

@jeremyarnon: Before business school you were telling me that you worked in finance and that you had a certain claim to fame as being the first in the world to do something. You want to elaborate?

@tristanwalker: Claim to fame or claim to infamy (laughing). Yeah, I was the first person in the world to buy oil at over $100 a barrel. I was a crude oil trader on Wall Street, wasn't very good. I was watching the prices one day and there was an offer at around $100.12. So, I figured what would happen if I bought this $100 oil. So I decided to buy one crude oil contract at $100.12. About 30 seconds later, I'm looking at the CNBC screens and they go, somebody just $100 oil. So, my claim to fame was buying that oil. Apologies to the world.

@jeremyarnon: I'm gonna send you my heating bill from that summer. So, one more question. I know that you're a big Twitter user, you've got a ridiculous number of followers at over 300K, but I've gotta ask you, what's the deal with your use of the word "rad"?

@tristanwalker: (Laughter) I got that from Dennis. The guy has put so many words into my head it's pretty ridiculous.

Jeremy Arnon is a mobile advertising executive based out of New York City. He can be reached on Twitter at @jeremyarnon