Starting out | Tristan Walker

Okay, so we're gonna make this very casual.

Okay.

These are our exciting group of students. They just started almost 2 weeks ago.

They're very close. This is awesome.

Yeah, this is gonna be nice and intimate.

You're welcome to be.

Okay, so Tristan, we want you to start kind of from the beginning. I think you have a very inspiring story to tell. So if you can just kind of start from square one, kind of how you got to the West Coast, and then we'll start Okay, let me make sure my phone's off, 'cause I don't want that to affect anything.

All right, so I'm from Queens, New York, born and raised. Are you from Queens, New York? Oh, that's awesome. See, that's cool. What part of Queens are you from?

Jamaica, Queens.

I was born in Jamaica, Queens. What part of Jamaica, Queens?

By Rosedale.

Oh yeah, my mom worked at Rosedale. Yeah, yeah, small world. So, you know, the story starts there. I like to say I have the whole rose that grew from concrete story, right? Projects, welfare, all that stuff. You're very nice. This is officially the most diva moment of all time. Thank you so much. So, born and raised Jamaica, Queens, again, Rosa grew up from concrete story. I had the good fortune to go to boarding school for high school on a full scholarship, and it was then that I actually got to see how the other half lived, right? I went to school with Rockefellers and Fords and all that stuff. And the most salient kind of part about that experience is that I was able to compete with them, right? And I got to see what wealth actually was. I knew I always wanted to be rich, but I really knew I wanted to be wealthy after that experience. And it was then that I realized that opportunity was opportunity. And I knew— I think I was 14 years old at the time— I said I had one goal in life, and that was to get as wealthy as possible as quickly as possible. I realized that there are 3 ways to do it. The first was to be an actor or an athlete. That didn't work out for me too well at all. The second way was to work on Wall Street. I did. I was an oil trader on Wall Street for 2 years. Hated it. Hated every bit of it. It was the worst experience of my entire life. And the day I really realized that, I said, shit, I've exhausted 2 of the 3 options here. The last one is entrepreneurship.

Mm-hmm.

I hate this place so much. Let me get as far away literally and figuratively as possible from Wall Street. I heard that there's a school called Stanford for business school. I applied. It was the only place I applied because I literally wanted to get as far away as like Atlantic Ocean, Pacific Ocean. And I got in. Like, that's legitimately the story.

Woo!

And I got in about a week after I was let go at JPMorgan in January of 2008. Now this was like a crazy time because at the end of the year you get your bonuses and all that stuff. My wife and I had just bought an apartment in Queens and we were just renovating and I lost my job. I didn't know if I was getting into business school, all that stuff. Turns out I got into business school, I got my bonus, I got 9 months of severance. I was just chilling at home until business school. So September came, actually we left in August, moved out here and then we realized that Silicon Valley existed. I didn't know about Silicon Valley at all. I just knew Stanford was an entrepreneurial place and it was far away from Wall Street. And I knew I wanted to be a part of it. And that first year of business school, I also worked full-time at Twitter when there were about 20 people at the company. In between my first and second year of business school, I joined Foursquare and then the rest is history.

Very cool.

Yeah. Sorry, I was very verbose in that description.

No, no, no. So you actually led us right to the next question, which is Foursquare. So the story about go out in partnership.

Yeah.

Businesses and you end up getting 300 in a week.

Yeah.

So please share your ways with the students because they're at the ideation phases and trying to get partnerships and really get out there and interact with the companies.

Sure. So the infamous Foursquare story. God, I've told this story about 8,000 times.

Yeah, I know. I'm sorry.

No, I'm happy to do it. Has anyone heard it? Oh, it's one person. Damn. I'm like waiting for that one room where like no one's heard it and it's like the most amazing story ever. So here we go. So it was June, July of 2009. Foursquare had just started in March of 2009. And it was just Dennis and Naveen, the founders at the time, right? And I knew I wanted to be a part of the company. So I reached out to Dennis and Naveen. I sent them 8 emails. The 8th time Dennis actually replied back and he said verbatim, he said, you know what, I just may take you up on some of this. Are you ever in New York? Dens, right? That's his shortened name. And I was in LA at the time with my wife, and I looked at my wife and I said, what should I say? Like, it took me 8 emails to get a reply from this guy. I want to make sure I don't eff it up. So 5 minutes later, I replied back. I said, actually, yeah, I was planning on being in New York tomorrow. I booked my flight that night, flew out the following morning, hung out with him for a week, and a month later I was running business development for the company, really as its like first employee. Crazy, right? And I think we had 10,000 users at the time. It's in the tens and tens and tens of millions now, right? We had zero merchants. We're in the millions now. We had zero brands. Well, at least from when I was there, we were in the tens of thousands of brands. It's probably way higher now. And that was just a story of perseverance. Like, literally, I walked up to the 5th floor in our little shoddy office. I knocked on the door. No one answered. I opened it. Dennis turned around, looked surprised, because I guess he didn't think that I was actually coming. And I did a beeline to the chair right next to him, sat down, and started working. And he said sign up 30 businesses in a week. I signed up 300, and it worked out. Literally the rest is history there.

Unbelievable. So a couple tips or pointers that you can share with why and how that worked for you?

Yeah, well, which part?

The getting 300 instead of 30.

Oh yeah, okay, yeah, yeah. Well, first of all, I knew I could get to 300. He's the person who said 30, and I said, okay, right away. So it started with that, and I knew I could do it faster than the month that he allotted for me. And then what it just boiled down to is just pure hustle, right? I knew as a user of the service the type of business offering I wanted to bring to the service, right? You know, it was a perfect moment when Dennis was like, what do you want to do with us? And the only role I could say was business development because it had the word business in it. I was going to business school, and it actually made a lot of sense. Like today, I get a lot of emails from folks who want to get advice on business development. It's like, I don't even know what business development is, right? Because I just like made up that title myself, right? It's not traditional. I almost think about that role as more of a product role than business development. And then we just kind of put business principles around that product or feature that would enhance the user experience. So the first tip is enhance the user experience first. Don't worry about the business. If you kind of get mindshare from people, you build a product that people love, the business stuff will follow. And for us, every business thing was still core to our product. We did a lot of business things that people had no idea was a business feature, but it just felt very core to the product. And as long as you're true to the user, kind of getting business partners, getting users excited about that, it's easier than people think.

Yeah.

The second thing is just focus, focus, focus. I think a lot of people when they start getting into business deals, et cetera, they want to get as many businesses on the platform as possible. Number one, we couldn't do it because we were limited in terms of bandwidth. I was the only person doing it, right?

Right.

And there was a point where I was getting 600 new emails every single day, right? Like legitimately. And I had to potentially reply to every single one. But there's no way I could work with 600 new businesses every single day and give them a high-touch experience. For the large brands, I said, all right, there are so many verticals in the world. You have auto, publishing, retail, et cetera. I was like, let me go after the number one brand within each. So on publishing, it was the New York Times. Retail, it was Starbucks. Television, we worked with Bravo Television. With CPG, we worked with Pepsi. With— God, I think we had 10 brands. And we launched them all at the same time. And this was in March of 2010, right before the next South by Southwest. And that South by Southwest was the time when we really kind of pulled away from the pack, because it was like us versus Gowalla versus every other location-based service that existed. And we went into South by Southwest with 10 of the most marquee brands, like really on the planet, who wanted to promote us. And everybody else, the great thing about it is that everyone else had to chase number 2 and 3 and 4. 4, 5, and 6. So we came out of South by Southwest completely separated from the pack and kind of ran from there. So focus and user. Very cool.

And then the persistence aspect of it, right? So you sent 8 emails before you got a response. I think that's kind of a point that everybody here doesn't really know that fine line of being a stalker versus being persistent. So if you can kind of talk to that point and kind of, you know, at what point do you think that you kind of have to give up on that and maybe move on?

Yeah, so that was my last email. I wasn't going to email him again.

You were like, 8's the cap.

Yeah, I mean, it's, you know or you know, right? You know, it's a blessing and a curse because now I get a lot of emails from folks and they always think that they have to email me 8 times before I reply back to them. It's like, really? It's like, no, it doesn't work that way. So for me, there are a couple things about Foursquare. I was willing to work with them or work for them for free even without their knowing. I was so passionate about the company that I just wanted it to succeed that I was willing to do work for them even without their realizing it, right? So I got to this point where it's like, all right, if you're not willing to give me the opportunity when you only have 10,000 users, nobody's knocking down your door to do the same thing. He's willing to work for free, has brought kind of really great ideas for you, and there's no strings attached. If you're not willing to engage me on that, Then it's probably not the right company for me to be working with anyway. And fortunately, as luck would have it, Dennis sent me that email back. And it was the best thing that ever happened in my career. But that was it, right? Like, hadn't he emailed me back, I would have just thought that and found another potential, like, very early, early, early stage company that I loved and done the same thing until I got to that point.

Awesome. Now, can you kind of bridge the gap between working for someone else and then finally Taking the run on your own company?

Yeah, no, I mean, I'm still working for people. I have a board and like investors and all that stuff. And it's not very different. The only difference is like as a CEO, I don't do much day-to-day work anymore, right? Like all of it is just like— it's true. It's just management of kind of employees, making sure that they're communicating with each other. We're at a scale now and a diversity of offering that like that's required.

Right.

I mean, we have a 6-product kit right now. We're going to have another product soon, another brand soon. But even that 6-product kit is like 50 different component parts. So you have the supply chain stuff. Then we have to build our HR infrastructure. Then we had to grow our customer base. So from a marketing brand perspective and performance marketing perspective, our customer success team has to be stacked. What kind of organization are we? Are we matrixed or are we monolithic? How does it look with one brand versus 2?

Right.

Right? And I haven't even talked about things that I need to do for work, right? Like, that's it. And the majority of the rest of the time is just recruiting, which is different from when I was kind of leading business development. It was like, that was my job, and I need to be the best person in the world at that job. Like, the best person in the world at that job. It's hard. Like, I really don't have an archetype for the best person in the world for this job. You know what I'm saying? Because no one's ever done this job before. It's a weird nuanced thing and the only kind of similarity to Foursquare there is like the whole location-based thing was relatively new, but the thing that I was doing in the context of it was just never done before. So I was able to out-execute people 30 years my senior because there was no context of how things should be done.

Right.

And it's very much the same now, right? Like nobody has any idea how it should be done, so we're really defining that for a lot of people.