This interview is with Jason Shen, co-founder of Ridejoy, a Y Combinator-backed community-driven marketplace for sharing rides. (Download the audio recording of this interview.)

Q. Tell us about your background.

A. Sure thing. I’m 26 years old. I was born in China, moved to the United States when I was three, and grew up in Boston, Massachusetts. I came to college at Stanford and got a bachelor’s in biology with an honors thesis in ethics and society, which meant I took a lot of philosophy classes. I stuck around, did a master’s in biology.

During college at Stanford, I was deeply involved in the gymnastics team and I was captain of the 2009 NCAA championship-winning gymnastics team, which was a real pleasure.

After college, my first job was being the chief operating officer of the Stanford Daily, which was basically running a lot of the business operations for this non-profit but very business-oriented company.

I then took a job at a startup called isocket where I was a customer scout, which meant I was doing a lot of sales, marketing, along with some customer support. And then after that, I started a Y Combinator-backed company with my friends and roommates, Kalvin and Randy, called Ridejoy. We help people share rides across the U.S. and Canada.

One other thing to mention is that, while I was at Stanford, I started a non-profit that focused on supporting microfinance loans to entrepreneurs in the developing world with Kalvin, who eventually became a co-founder of Ridejoy with me.

Q. Tell us how your career has taken you to your current role. 

A. Sure. I would say it comes back to my interest in technology. In middle school and high school, I really liked seeing all the different kinds of technologies out there, playing with things like Photoshop, learning HTML, messing around, making GeoCities pages, little things like that, nothing too serious. But I always found playing with computers pretty cool.

I did well in science-based classes in high school. I took a couple AP courses and so when I got to Stanford, I had a general interest in science. In my first year, I explored different classes but realized that something more science-oriented was going to be best for me.

I majored in biology because it had a broad range of different sciences — physics, chemistry, as well as biology and there were these problem sets, so that was a practical consideration.

I loved all the energy that was happening in Silicon Valley — seeing Google, Apple, seeing all these different startups coming up, but I didn’t know how I would be able to play a role in these companies because I wasn’t a programmer.

I had taken some programming classes in high school and then a little bit in college as well, but I was really struggling with the amount of time it took and the mental processes that were required that, for whatever reason, weren’t something I felt particularly where I could excel. So I was thinking, “If I’m not a programmer, how can I get involved in a tech company?”

Before starting a non-profit, there was one other thing that really turned me on to the idea of entrepreneurship, and that was I had this idea — I wanted to create a book that collected Stanford students’ thoughts, and it was originally between the end of my freshman year to the end of my sophomore year.

I called it “The Stanford Spirit,” and I created this form where people could write in. It was basically three prompts: “I remember…”; “I live for…”; and “I would like to….”

And you’d fill in your responses. I posted advertising everywhere. I convinced the bookstore to give me free gift cards that I could use as a reward for people to post.

I tried to recruit a co-founder whose column in the Stanford Daily I’d read and who seemed interesting, and we worked together. There were a lot of ups and downs, but ultimately, I was able to get an ISBN number, get these books printed, and sold 50 copies to the bookstore over the course of one year.

At the end of the year, I was like, “Holy shit. This is something that a year ago, I just had in my head. It was just a thought and now there are physical versions of this, a real book that I sold to somebody who wrote me a check for this thing that I just thought of.” That was amazing to me on a lot of levels. And so, that was one breakthrough, but it was a very personal endeavor.

Then later, starting Gumball Capital with Kalvin Wang and another friend was more of a group effort and so, that seemed like, “Wow. When a couple people come together with a shared vision, the results can be even more tremendous.” We toured college campuses across the country. We were able to raise close to 900 microfinance loans.

That was an accomplishment on an even greater scale than I could have imagined doing something on my own. Working with a group, clearly, there’s this additional level of power that comes with it.

At the end of college, I realized I didn’t want to do research. I didn’t want to be a doctor. I’d explored those areas, done shadowing, done research but I realized it wasn’t for me.

I took the Stanford Daily job because there was this business element of it which I really liked. You were in charge of the P&L statements. You were managing other adults who had been working at the Daily part-time for a decade and also in charge of generating revenue through ad sales and things like that.

It was also a non-profit as its model, which I was familiar with, and it had a mission to be the paper of record for the Stanford community, which the company took seriously. So that was a great role.

I learned a huge amount about what it’s like to really run a business, the mechanics of a business. And that led to me to realizing that I really could contribute to a startup in a business role, that there were business opportunities available, that I was developing real skills that could contribute to a startup.

So from there, I started applying to startups. But I wasn’t quite getting the attraction I wanted. I was doing some creative things. I applied to AirBnB with this slide show. I had an interview with them, but ultimately they didn’t give me an offer.

The breakthrough, to be honest, was when someone I knew was trying to leave the startup world and enter the non-profit world, and I was trying to basically do the opposite. He’d been talking to me, asking to meet up, and I was brushing him off. I didn’t want to talk to him. And finally, I sat down with him and I was like, “Wow. This is great.”

I gave him some names of people I thought he could talk to and he gave me the names of some people he thought I should talk to, including a recruiter, who ultimately helped me identify this role at isocket. That is usually not common. A recruiter usually doesn’t usually recruit for business positions. They usually recruit for engineers. So it’s an uncommon stroke of luck that this happened, but there it was, and it was good.

So I jumped into this role at isocket. I think the co-founder and CEO really liked me because he was also an athlete and he also hurt himself very seriously during athletics, and I’d blown out my knee while doing gymnastics. That’s why I stayed a fifth year at Stanford. And also, I had this advertising experience, and I understood where the future of advertising was going. I think I really understood his vision better than nearly anyone else at the company, from a business perspective.

So I worked there for nine or ten months. I gained a lot of tactical skills in dealing with customers, closing customers over the phone, doing support for them, working with engineers when there are bugs and things that need to be fixed, and also just seeing generally how to pitch.

John Ramey, the CEO and founder of isocket, is a really incredible salesman, and I mean that in the best way possible. So I learned a tremendous amount there. At the same time, I was still really excited about the idea of doing a startup for myself. So an opportunity came together when me, Kalvin and Randy were roommates.

Kalvin was, at the time, working at a startup called One Block Off the Grid, which was like a Groupon for solar panel installations. They bundle a lot of people together and get them a discount. Randy was an engineer at Scribd, which is a YC company. We were all friends.

We started talking about, “What if we did something together? What if we applied to Y Combinator? What could we do?” It’s something that starts off really easy: “We’ll just fill out the application. Let’s see what happens.” Those commitments roll and roll and roll, and eventually we came up with some ideas that we really liked; we got an interview.

As you know from the Vanity Fair article, we pitched a different idea at the interview and then they accepted us, even though they weren’t sure about either of these ideas, but they figured we’d come up with a new idea, which we did, and that was Ridejoy. I’ve been doing Ridejoy for over a year now, and it’s been a really incredible experience.

Q. For those unaware of the Vanity Fair article, what exactly is that article?

A. There was a journalist named Randall Stross who gained permission from Paul Graham to be basically embedded inside a YC batch, which happened to be Summer 2011, which is when Ridejoy was incubated.

So he sat in on interviews, meetings. He sat in when the partners were just talking by themselves. He interviewed lots of YC founders. He was at the dinners, and he would sometimes sit one-on-one with us and talk to us about our companies.

Through that, he wrote a book called “The Launch Pad: Inside Y Combinator, Silicon Valley’s Most Exclusive School for Startups.” It’s a pretty hyperbolic name, but the actual content is extremely accurate. It’s very cut-and-dry; it’s not a breathless commentary.`

Vanity Fair published an excerpt of the book which included our journey from our backgrounds, to the pitch, to incubating ideas, to prototype day, and then finally demo day, where we show off what we’ve done over the past three months.

Q. Tell us about your blog, “The Art of Ass-Kicking.” How did it get started and what do you write about?

A. That’s a really great segue because the blog started in Fall 2010. So it’s been about two years now. I had been interested in blogging and I had started a WordPress blog in college; I wrote some posts here and there, sporadically, and then it died off.

At one point, I had a Tumblr blog, where I was using it the way a lot of people do, just saving links, saving pictures, saving quotes, not really writing a lot of posts but more on curating content.

I finally gave blogging another shot because of my coworker, Ryan Hupfer, at isocket. He had a blog called “Hup and Steph,” which was him and his girlfriend, then later, his wife, where they just documented their personal lives — trips they’ve taken, things they’re doing.

And here and there, he’d throw in a more content-oriented post, like he had this shoulder surgery and he had looked online for all kinds of information about this type of surgery. He couldn’t find anything, so finally, he wrote an article about what it’s like to get the surgery, what you should expect, recovery, all these things.

And he says, to this day, people e-mail him saying, “I found your blog post about the shoulder surgery. Thank you for writing that. I have this coming up, and I’m really nervous about it. Your post really helped me feel better. You gave good content; you gave good info.”

He’s like, “Look, if you write this post and one person’s life is changed in this way, it’s worth it, right?” Because that was one of the things I’d kept saying to him. I’m said, “Nobody reads my blog posts. So what’s the point? This feels like a waste of time.”

And he was like, “Yeah, if one person reads it, it’s worth it.” And I was like, “You know what? You’re right. I should just write to share some of my own experiences. If anyone finds it valuable, that would be great.” It’s a good chance to practice writing. It’s a good chance to internalize some of those lessons I am learning now at the startup.

And I had also previously wanted to blog a little bit while I was at the Stanford Daily because I’d been learning a lot about the future of journalism. But at that time, the editor-in-chief was like, “Ah, it’s kind of weird for you to be blogging because you’re not on the editorial team.” So I had this pent-up itch to do that. And so this was a great chance to do that.

When I started off, it was just jasonshen.com. It wasn’t called “The Art of Ass-Kicking” right away. I just started writing blog posts about things I was learning at the startup.

The breakthrough moment was when I teamed up with a friend, Derek Flanzraich, who was someone — also a recent grad — who had a couple interesting blog posts himself about how TV was going to get disrupted, and how this basically got him a job at a TV startup, because everyone was reading his TV blog post.

And I was like, “Hey, I’m writing a blog post about how recent grads can get jobs at startups, especially now in times of change. Do you want to look over my draft?” And he looked it over, added a ton of other comments, and I was like, “Okay, I guess we can co-write this article.” And so we did.

We wrote this article called “How to Get a Killer Job at a Tech Startup as a Recent Grad,” and we posted it on Hacker News, which is the community tech watering hole run by Y Combinator, and it did really well. It hit the front page. It had 35 up-votes, and so that meant that around three- to four-thousand people had visited that Reddit page in one day.

Previously, my blog was getting maybe 15 visits a day — very, very minimal. Some days, nobody would come. And that was mind-blowing to me. I was like, “Holy crap. I could write this post and all these people read it.” Sure, most of them just skimmed it or just left. But still, at least a few hundred people read the whole thing. That’s kind of amazing, and that was really motivating to me.

People wrote good comments, saying that this was helpful to them. And so, it really motivated me to continue writing and to continue providing value to readers and hoping to get those bumps where a lot of people check out the posts.

I’ve been doing that for about two years now, and my traffic is still pretty spiky, but it built my personal brand as someone in the startup space. It helped me improve my own ability to communicate. It helped me form numerous connections that offer that serendipity that normally would not happen. If someone stumbles upon your post, sends you an email, you guys meet up for coffee, all kinds of really interesting things happen from that.

Now, it’s starting to become a distribution platform for me. If there’s something that I want to get out there, that I want to talk about, that I want people to see, I can write it on my blog. I’ve created this mailing list. People get it delivered straight into their inbox. If I share it online, a lot of people can pick it up.

Then the last thing, the value it provides me is that it’s like a sandbox. If there is some new service that’s supposed to double conversion rates, I can just install the code on my blog and see what happens.

I’ve been able to test a lot of things, like learning more about e-mail marketing, or learning about how to tie in my Wufoo form into MailChimp, and doing all these things is just a low-risk way to learn stuff. If it breaks, it breaks. Fine. No one’s going to yell at me. It’s my site. Sure, I’m not happy that it goes down, but it’s not the end of the world. So, yeah, the blog has been really valuable in a lot of different ways.

Q. Tell us step-by-step about your application to Y Combinator — what lessons did you learn about applying?

A. Me, Kalvin, and Randy have all been great fans and admirers of Paul Graham. He has written a number of very influential essays on his website that we’ve all been reading through college. I remember looking back and seeing them in my sophomore year. I e-mailed one of those essays to my girlfriend. I’m like, “This is so great. You’ve got to check this out.”

So we’ve been aware of him and what they’ve been doing for some time. I think we all thought about doing something there, but that desire hadn’t crystallized, maybe in part because we didn’t know who we were going to start with. Maybe we weren’t 100 percent sure about an idea that was really going to nail it.

It probably was triggered because, in January 2011, Kalvin was finishing his time at One Block Off the Grid. He’d been there since college basically — two-and-a-half years. That’s a pretty long time in a startup world. He was getting ready to actually travel the world, travel the U.S. and go abroad and things like that.

A couple days before he left, he sent an e-mail to me and Randy. We joke about this, but once in a while Kalvin will send these life-changing e-mails. He was like, “Hey, what do you guys think about the three of us doing a Y Combinator application?”

And I was like, “You know, I hadn’t really thought about that. But when you mention it, I’m very interested. Let’s talk about this.” I think Randy was probably the most “content” to stay at his job; he felt like he was learning a lot. And he really enjoyed his co-workers, enjoyed everything about working at Scribd, so he said, “I can see myself leaving sometime, but not so soon.”

We spent a lot of time talking about it, and I think we were still not quite there. And it was the day before Kalvin was going to leave and we were talking and talking, and he had to go home. We drove home to his house in Saratoga together from San Francisco.

This sounds so silly but we slept over at his house. We were talking and talking and finally, we were like, “Let’s just try it.” So that was step one — commitment that we were going to try and do this.

So for the next couple weeks and months, we would Skype with Kalvin almost every other night. Me and Randy and Kalvin would get on Skype together and we would just talk about ideas and think of things that would be interesting to do. We had this long list of ideas and interests. We would look at other people’s ideas, too — for example, there’s this website called Springwise, where you can see different startup business ideas.

We finally came to one we really liked: we all really find some value and nostalgia in “memories.” For instance, Randy takes a lot of photographs from his travels. Kalvin will dig up old e-mails from time to time that he really likes and he kept a live journal in the past that has some great stuff in it. And then I have a journal that I keep that records what I’ve been doing last year, the year before, the year before that. So in ten years, I can see what I was doing every single day.

We crystallized this idea and then we worked on this application to describe it, to sell ourselves. We got a lot of feedback on the application. We sent it to a lot of friends. We’d send it partly to entrepreneurial friends to give us feedback and then we’d send it to friends who are good writers and we’d have them just critique the writing and say, “Is it clear? Does it make sense?”

So by the time we had submitted the application, we had had several rounds of feedback from multiple people, and we integrated that feedback together. We got invited to an interview. But when they invited us, we were told they weren’t so sure about our idea. They didn’t know what was the attraction.

So they wanted us to think of another idea and this was a week before the interview. We were like, “Holy crap. We spent months on this idea and now you want us to come up with another idea in a week?” So we spent a long time talking through new ideas.

I think one interpretation of Ridejoy came up, but then it got shelved because at that time, we were thinking about it in a different way. Finally, the night before the interview, we come to this idea about “Let’s print photo books that are personalized. It’s like only a slight shift from the memory space.”

So we interviewed with this idea about photo books. They were a little skeptical, but then Paul Graham was like, “This could be the Altair Basic.” Which is his big metaphor for the fact that Microsoft created an Altair Basic compiler, which at that time wasn’t very impressive because not many people used Altair Basic, I guess. But that compiler can be used for a number of other languages which did make it useful. And then it was only a few steps to something really powerful.

So the fact that the program recognized that there’s a seed to something there was good. But otherwise, there was a kind of negative feel to the atmosphere. There were moments in the interview where there were long periods of silence, and all the interview prep we had read was like, “Be prepared for rapid-fire questions. You’re not going to be able to answer all the questions.” We were like, “They’re not asking any questions. I don’t know if this is good.”

We did the interview. We went home to Kalvin’s house and just sat around waiting because they call you that day to tell you whether or not you’re going to get in. We were just hanging out and it was getting later and then Kalvin’s on the phone with somebody and he was like, “Uh-huh.” And we were like, “Who’s he talking to?” And then he’s like “I’m going to put you on speaker phone.”

And then he puts it on speaker phone. He puts it on this table near where Randy and I were sitting at, and it was Paul. And he’s like, “Hey guys, we’d like to invest in you, blah, blah, blah,” and he lays out these terms. And he’s like “So what do you think? Do you want to do it? You don’t have to say so now. You can call back.” And we were like, “….Mmmmmm…yep yep. We want to do it.”

So that was the process.

Q. How is YC structured? What is the value of doing it?

A. Y Combinator is a seed fund. They call it an accelerator. And the idea is that these three months in the program is a time where you can really just hunker down, make a lot of progress, and do a lot so that, at the end, you have an opportunity to present in front of around two or three hundred investors at what’s called “Demo Day.”

There are weekly dinners on Tuesday nights at their office in Mountain View where you get to eat with your other “batchmates,” chat, mingle, socialize, learn from each other, and you listen to a speaker, usually a well-known entrepreneur, or venture capitalist talk about their experiences. And it’s very honest, very candid. People share things. It’s all off the record. So they share things they normally wouldn’t share in a more public forum.

You have office hours where you meet with the YC partners like Paul Graham or Paul Buchheit, who invented Gmail, or Garry Tan, the founder of Posterous, and talk about your business, talk about your challenges. Otherwise, we were working a lot. So that was the format.

Y Combinator makes a small investment in your company. You also get a follow-on. There’s an equity investment of between $15,000 – $25,000, depending on how many founders you have. I don’t know exactly the numbers but then there’s this follow-on investment that’s $150,000 convertible note, which aren’t directly equity investments but can be converted to equity at a later round.

So with that, you basically have $170,000 you can use toward working on your company, which is a tremendous start. And you get access to these entrepreneurs and investors in YC who have seen so much.

I think the most under-appreciated thing from an external perspective is your batchmates. It’s like grad school except that people do some really cool stuff rather than just going to college. They are really smart. They’re really capable and they will take your e-mails and respond to you. They’ll tell you stuff that you don’t hear from other people. They’ll make introductions that are really valuable that cost them some political or social capital to do it, and that’s a tremendous asset to have.

All of a sudden, 150 people are ready to do that for you, and you’re ready to do that for them. That’s a huge amount of value. So that’s the program.

Q. So you got into Y Combinator, and then you changed your idea. How did you change from the photo book idea to Ridejoy?

A. It was really just the fact that we were forced to come up with a new idea in the course of a week. We realized we were better off focusing on something that was all digital rather than being a physical goods company, i.e., printing.

So we returned to the ride-sharing idea and thought through it some more, thought through some opportunities and strategies that would make it more effective. And we realized  we had some of those. We went forward with it. But we also examined numerous other ideas and thought about them and did some small experiments, but the ride-sharing one ended up being the best.

Q. What is your current role at Ridejoy now? What do you do day-to-day?

A. It has evolved tremendously over time — from the three of us in our apartment working all the time, to having an office and having employees. After YC, we went to fund raise. Kalvin and I spent a lot of time talking to investors. Then we were hiring our community manager; before that, I was doing all the e-mails, supporting all the live chat.

Once our community manager, Margot, who is incredible, came on board, we trained her to do a lot of those things. So there was a training process and then we spent time trying to go after events. So I was going out there on the phone, calling people, trying to get their events to use Ridejoy as a ride-sharing platform.

Then we were working on an iPhone app, and then we were doing press for the iPhone app, and talking to journalists about the product, things like that.

It’s just evolved tremendously over time. Day to day, it can look the same but month to month, it can be very different.

Q. Where do you see yourself in the future, and how do you think what you’re doing today will help you toward that goal?

A. I think I’m always going to be wanting to build things and make things and create organizations that do good for people. So on a larger scale, it’s really going to be the same. What that looks like on a smaller scale is, it depends.

I really believe in what we’re doing at Ridejoy. I think it has a lot of potential, and we’re doing the best we can to capitalize on that opportunity.

Startups are always risky and there’s no guarantee this is going to work out and be the next Facebook, although we would love it to be, and we are doing everything we can to be the best we can be. It’s really hard to say where things will be, but if I’m not working at Ridejoy, I’d be working on another kind of project or opportunity.

One thing I really like about Ridejoy is that it’s really opening up options for people. It’s allowing them to get to places they otherwise couldn’t. It’s helping them form connections and friendships with people they otherwise wouldn’t have been in contact with, and I really love that.

I hope that whatever I’m working on, the product or service provides that similar kind of value to people because that really is me. It fulfills me.

Q. If you could talk to your younger self, what would you say? 

A. There are a couple things. The first is, figure out how you learn best and try to gain skills that are useful. I found that I’ve learned best through doing projects, so I had to do projects that require me to obtain certain skills that are necessary to make the project work.

I didn’t set out like, “Ah, you need to be good at sales.” But from that book to doing Gumball, it required me to go out there and talk to people, convince them to do something or to join our group or to…whatever. And you get better and better with things like that over time, and it’s a very useful skill that can be spread across different things.

I’d say, don’t be afraid to jump around a little bit, because especially if you are doing something creative, if you see yourself in a creative role, those experiences, those lessons and that diversity will benefit you in the long run.

I think the last thing is when you see an opportunity, go after it. You can’t manufacture opportunities; you can’t manufacture good luck. I can’t tell people, “You want to start a startup? Just start a non-profit while you’re in college with a guy who’s a CS grad from Stanford and then have as your other roommate this other guy, who’s an amazing engineer who happens to work at a startup.” That’s not going to be useful.

But what maybe is more useful is: You don’t know when the opportunity is going to come, but keep your eyes peeled. Continue to make yourself into someone who is smart, well-connected, influential, has skills, is capable of doing a lot of different things. Recognize where you can add a lot of value, where there are people who can help you augment your skills, and where you share values and vision with them. And when an opportunity arises to work with them, jump at it.

So just be prepared, and keep your eyes peeled.

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