Jason Shen co-founded Ridejoy, was a Presidential Innovation Fellow at the Smithsonian, is a NCAA National Champion gymnast and is the author of Winning Isn’t Normal. In this interview we talk about Ridejoy’s failure, why you should start blogging, and how to travel the world solo.

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Jason Shen, welcome to the show. If you would, introduce yourself.

The most notable thing I’ve done is start a company called Ridejoy, a long-distance ridesharing marketplace. We were funded by Y-Combinator in the summer of 2011, and we’ve helped tens of thousands of people share trips all across the U.S. and Canada.

I studied Biology at Stanford, where I was also on the gymnastics team. We had the good fortune of wining a NCAA National Championship while I was there.

What else? I write a blog called The Art of Ass-Kicking. It is all about conquering fear, building strength and making things happen.

You’ve also recently written a book.

That’s right. I published a book called Winning Isn’t Normal, which is a collection of my best blog posts over the years. It is organized into three fields: mind, body and work.

Let’s start by talking about Ridejoy, a ridesharing program. What made you want to start Ridejoy?

Before I started Ridejoy, I was living in San Francisco. I was working at a startup called iSocket, which is an ad-tech company. I was living with two other guys Kalvin Wang and Randy Pang. I knew Kalvin from college.

Kalvin and I started a non-profit in college called Gumball Capital while we were at Stanford. That is when I realized I wanted to get involved in entrepreneurship.

Kevin Jason Randy on the Roof

The Ridejoy founders have a discussion on the rooftop. Jason Shen (left), Kalvin Wang (right) Randy Pang, (bottom).

I always loved technology. I remember building sites in GeoCities, and messing around in Photoshop as a kid, but when I took my computer science classes in high school and college I never did well. Programming wasn’t my strong point. My involvement in Gumball Capital showed me that there were ways to get involved in entrepreneurship other than programming.

Fast forward to San Francisco, I was working at a startup, and wasn’t terribly happy. I wanted to figure out what was next.

Kalvin had just left a job at a startup. Randy was our third roommate, and an engineer from Berkley. We kind of looked at each other one day, and said “Wouldn’t it be awesome if we could start something together?”

We were friends, and had different skill sets. We thought that if we put them together, we could do something cool.

After you guys decided to start a company, what were the early days like? For the entrepreneurs out there watching, what was the first step?

You know what? We got really, really lucky.

We had been reading Paul Graham’s essays forever. We knew that if we were going to start something, we wanted to get into Y-Combinator.

So, we applied with an idea we had called Re-love It, which was about rediscovering content that you had already liked or shared on social networks. After six months or so we’d bring that content back to you.

When we applied to YC we didn’t have much of a product—this is not the recommended approach for applying to Y-Combinator. They said, “We like you guys, but don’t like this idea. Come interview with us, and be prepared to talk about new ideas.” For the next week we were scrambling to come up with new concepts.

We decided to pitch an idea around printing photo books of your best content—kind of like an auto-generated yearbook that came from Facebook.

They didn’t want to receive a check or a PayPal payment. They just wanted cash, and that was a problem.

The interview went OK. They called us back and said said that we had been accepted into YC. We found out later that they had written in their interview notes, “Super-enthusiastic founders. Fun for the new idea.”

We thought that meant they were interested in the idea we pitched them. It actually meant fun for the new idea we are going to come up with in Y-Combinator after they ditch this idea.

That was like finding out we were part of a prophecy. It was crazy.

We spent the next three weeks siting around our apartment, googling crap, trying out random apps. We were looking into ports that plugged into your car and told you information—perhaps, we could build an app store for cars?

Finally, we started looking into long-distance ridesharing. We were looking at Craig’s List. It was incredibly disorganized, yet there were 100 to 150 new posts each day.

That is what we call a proxy for demand—we don’t know that people need your service, but you can see there is an obvious need. That is when we decided to put a stake in the ground, and start working on ridesharing.

So, your question was about the next step? Now that you have this idea, what do you do?

One of the first things we did was talk to the people who share rides. We had all taken long trips for friends, but we hadn’t done this anonymous long-distance thing. What are the dynamics? How do people feel about riding with strangers?

I decided to cold call about 50 people who had posted their phone number on the ridesharing section of Craig’s List. Most of them were open to talking. I’d ask them how did they learn about ridesharing? What was their experience like? Do they pay? I had this whole spreadsheet of the people, and what they said. It helped create the groundwork for what we were doing.

Meanwhile we decided to find a way to jumpstart this marketplace. We needed drivers and passengers starting at the same place, and going to the same place on the same day. There are a lot of different variables to match up.

If you are a genius engineer, but nobody understands you, will that genius ever be realized?

Imagine that you are selling an Xbox on eBay. If it doesn’t sell, you still have the Xbox. That isn’t the case with ridesharing, because it evaporates. Once the diver leaves, it’s gone.

Kalvin had gone to Burning Man the year before. Burning Man is a festival in the deserts of Nevada. 50,000 people come to the desert for a week—there is art, music and dancing.

Burning Man has a specific date and a specific destination, so all we needed to do was match where people were starting.

We built a website called burningmanrides.com, and promoted it to festival attendees. This happened in parallel with the customer development work I was doing.

So Burning Man Rides was like your MVP to test the waters. What were the results?

We got lucky again.

We made a site that felt like it was for burners, by burners. We got picked up by the Burning Man Facebook group, which had close to 250,000 followers. That alone got us about 2,000 likes, and a ton of shares—people just started signing up.

We launched Burning Man Rides on August 1, which is fairly late considering Burning Man is August 20. In the following weeks we got more than 1,600 signups, 1,200 rides were posted, and there was a huge amount of messaging happening on the site—this was all through Facebook Connect.

So, you guys figured you had a proven concept?


You go through this 10-week program, they bring in speakers, give you money, help prepare you—at the end of the day you have to present to hundreds of the best investors in Silicon Valley. You have to have that chart that goes up and to the right.

We were fortunate to have a growing number of ridesharers on our site, and to have that chart, and to have a story.

AirBnB was the breakout success in 2011. They were finally seeing big success. We made a lot of comparisons to AirBnB and eBay—these were all marketplaces that you wouldn’t think should exist. There is a lot of trust involved, and previous attempts had been unsuccessful.

I think that story registered really well with investors.

At that point you guys had to be thinking about monetization, or were you?

I think monetization is the ultimate move for a marketplace. We thought about it early. The majority of ridesharing transactions happen with cash, which is why we wanted to implement a payment system.

It was going to take us a couple months to build. One of our mentors at YC suggested that we release a basic version with just messaging, and figure out payments later. He told us to focus on making mistakes, and getting growth. Payments were going to slow our time to market. We took his advice and launched an application with just messaging, no payments.

In retrospect we should have pushed harder for growth. I’m not sure it would have changed the game, but growth mattered more.

Ridejoy failed. When did you first realize that it wasn’t going to work?

It came in a couple of stages.

We were funded in October, November of 2011. We raised 1.3 million, which was exciting. I’ve never seen a bank account that had that many zero’s in it.

It is also incredibly intimidating, because there are a group of people that are giving you money to turn into even more money.

We started hiring people—a community manager to improve our community. We felt that having a strong community would make people more comfortable sharing rides. We hired a designer and an iOS engineer. We started designing an iPhone app, and poured our product hopes and dreams into it. The website was great and all, but the app was going to be the core experience.

Around this time, we were growing about 25 to 30 percent each month, and getting about 300 ride posts each day.

August rolls around, and we release our iPhone app, and suddenly there is a brief spike in activity. However, the iPhone app doesn’t seem to be bringing in new users. It wasn’t something that people were going out there to find despite all the great press.

We had also implemented payments at this point. We had given riders the option of accepting credit cards or cash, but drivers were only taking cash. They didn’t want to receive a check or a PayPal payment. They just wanted cash, and that was a problem.

We like you guys, but don’t like this idea. Come interview with us, and be prepared to talk about new ideas.

We started thinking about what we needed to do to raise another round. We had about $700,000 in the bank, which would last us 13 months. We needed to raise a series A, and that takes about six months, which means we need to start pitching in seven months.

What are we going to look like in seven months? We started talking to investors about our chances of getting funded. Answers were in the range of absolutely not to the bottom end of maybe.

A couple weeks after we released the iPhone app we got a cease and desist letter from Craig’s List. We were scrapping listings from their site and putting them on ours, and encouraging people to post on there from a third-party app. You aren’t supposed to do any of those things.

Some friends of ours also got a cease and desist letter from Craig’s List. They spent $10,000 on legal fees and still had to stop what they were doing. We figured we had better do the same. Moving off of Craig’s List cost us 50 percent of our new user growth.

That was when we knew we needed to pivot.

I want to move on to writing, your book and your blog, but I have one more question. If you start another company, what will you do differently?

There are a lot of things I will do differently, and it’s not because they would have been successful with RideJoy.

I’m a different person than I am before I started RideJoy. I’ve got different skills, resources and am under a different set of circumstances.

With my next company, I want to prototype the initial version myself, and make it good enough to close initial customers.

I’d like to make it something that people can purchase—not because I’ve given up on consumer, but because I think those types of products benefit from thought leadership, and good writing.

I would also wait sometime before looking for a co-founder. I’d want to validate an idea, have some initial customers and a prototype before asking any co-founders to join.

That is a great segue. What are the keys to writing great content?

I’ve been writing on my blog since 2010. It started, because a co-worker that blogged, encouraged me to start.

Who am I? I’m no expert. I always felt bloggers would write things like “This is what Apple will do next,” or “Here’s why Microsoft should do this.” How do they know?

He encouraged me to write about what I was learning. So, that’s what I did.

I did my first post with a friend, Derek Flanzraich, about how to get a startup job out of college. The post did incredibly well. We posted in on Hacker News, and it climbed the charts. It was addicting to see people come to the site.

I think it did well, because it was useful. People were interested in how to break into startups, and wanted to hear from two college grads that had done it.

Creating great content is, in a lot of ways, like creating great products. You have to understand who your audience or user base is. You have to make something that is targeted towards them.

Our post wasn’t just about breaking into startups. It was about breaking into startups as a college grad.

I’ve given this talk about how to create compelling content for the web. Great content is useful, unique, enjoyable and compels people to share.

We just discussed useful. Unique is something that you can’t get elsewhere. If you can get it elsewhere, it is a commodity or a duplicate. If it isn’t enjoyable, people won’t care. Compelled to share—give people a reason to share it. Write things that others think, but don’t know how to express. Write things that are useful to people’s friends.

Those are some of the elements of great content.

Presidential Innovation Fellows

Presidential Innovation Fellows Jason Shen, Vidya Spandana, Diego Mayer-Cantu in the Eisenhower Executive Office Building, one of the two buildings where White House staff work.

That’s interesting. I’ve always thought that people read either to learn, or to be entertained. Those go hand-in-hand with useful and enjoyable, but I like unique.

For those that have been pondering starting a blog, why should they?

I talk about this in a podcast I started with Sarah Allen called the Tectonic Podcast.

Sarah is a serial entrepreneur and a software engineer. We worked together at the Smithsonian while I was a Presidential Innovation Fellow. We were going separate ways, and wanted to find a way to keep working together, so we decided to start a podcast.

Our second podcast was on the value of blogging. Sarah has maintained a blog since 2002, and has seen the landscape change.

She says that communication is important even if you are the most technical engineer. You need to be able to communicate. If you are a genius engineer, but nobody understands you, will that genius ever be realized? Communication is key in allowing your intellectual potential to be reached.

Blogging teaches you that it is difficult to get your thoughts into words. Something that sounds so great in your head often doesn’t sound right when you put it on paper.

There are more convincing reasons to start a blog.

In retrospect we should have pushed harder for growth. I’m not sure it would have changed the game, but growth mattered more.

Chris Yeh, who is the VP of marketing at PBwiki. He’s an investor and a blogger, and says that blogging is like assembling a little army of soldiers that go out and fight for you. They never rest. They never sleep. They are constantly sharing your ideas with the world.

My blog has become a huge part of my professional assets. The reason someone might hire you, or do a deal with you could be a number of things—your knowledge, skills, connections. My blog has become one of the things that I bring to the table.

It’s like a giant dog that I bring around with me. It’s hungry all the time. I have to feed it. At the same time, it is useful. I use the blog to promote the work that I’m doing. People know me, because of my blog.

A blog has allowed me to be much more successful than I would have otherwise been. It is a channel to connect to other people.

Recently, I read a book called Designing Products for the Web by Randy Hunt, who is the director of product development at Etsy. I’m considering applying for a job there.

There was only one review on Amazon, so I went and wrote one.

I emailed Randy and told him that the book was great, and that I left him a review. I asked him if he’d like to do an interview on my blog, and mentioned that it would be a good channel to get word of his book out there. He agreed, and we’re going to be doing an interview.

Now, I’m going to be talking to the guy who runs product development, at a company where I’m interested in working on the product team. Who knows if anything will happen, but certainly I’m in a much better position than someone applying to the job out of nowhere.

I’ve been writing for several years, and am in the process of rebuilding my personal site. I look back on my old writing, and I’m embarrassed by the quality of it. Do you feel that way about your old work?

When I was putting together Winning Isn’t Normal, I was going back in the archives with a friend and looking articles that had been popular early on in my career. She’d point out how all the words and phrases that just sounded goofy. A lot of it felt awkward, even childish.

For many years I refused to keep a journal. I’d go back and read my old writing, and think “I hate the person that is writing this.”

So yes, I think it is normal to be embarrassed.

Do you have a routine that you follow? I know some people write a specific amount of words each morning.

Not really. I’ve been moving around a lot. I just traveled to Peru.

I don’t have a routine, but I get antsy if I don’t write for a while. I was going to say workout, because that is also true.

It’s a good sign, because that means it is a habit.

Tell me about your trip to Peru.

I was talking to my friend Mark Bao, who was the CTO of OnSwipe. He is going back to college after dropping out and working on startups for a while.

He had been backpacking abroad for a year, and that was something I never did. I didn’t have a post-college trip. I was always studying or working. He told me that it was something I had to experience. I kept asking why? Why should I travel solo?

He convinced me that I would learn more about myself. It would give me something that would enhance my life.

Jason Shen Machu Picchu

Jason Shen sits on a ledge overlooking Machu Picchu while on his trip to Peru.

I booked this 12-day trip to Lima in Peru. I don’t speak a lot of Spanish. It would be my first solo trip, and my longest trip in a while. Peru is a large country, and people kept saying “You have to go to Machu Picchu.” So I flew to another city and visited it.

It was the first time I felt a lot of anxiety in a while. As an entrepreneur, I do things that seem risky to most people, but really I have the control and ability to accomplish other tasks—all that changes when you go to another country. I didn’t speak the language, and I didn’t know if the things I’m good at would be helpful. As we mentioned before, if you can’t communicate with someone, it doesn’t matter how smart you are.

You had to be aware of your surroundings. You had to be more present, because you couldn’t count on others to be there for you.

Beyond what I learned about coping and survival, was about my own preferences. When you aren’t with someone else, everything is up to you. Do you want to stay in the hostile, go downtown, go surfing? It is up to you to decide. It is up to you to know what you like.

I think it is important to know what you like and what you want. Even if you are unable to do it all the time, you should know. It is almost like a test—if I think I go out and do this today, I’ll enjoy it. And sometimes you don’t enjoy it, but you learn.

Do you plan on taking more trips by yourself?

I’d like to. It would be worth doing more trips in the future.

Let’s go back to your writing. What prompted you to write a book?

A friend said that I should provide some exclusive content when others sign up for my newsletter. He suggested that I also offer a drip email campaign containing my five best posts. It was a good idea.

I started looking at what posts I wanted to add to the list, and it kept growing. I couldn’t send people my 30 best articles. It would take two months to read.

That’s when I started thinking about putting it together and publishing it. Some of my articles are long. As a result Winning Isn’t Normal has about 50,000 words.

I always wanted to write books. In the future, I hope to write a book that is published by an actual publisher. I know the amount of money you get is less, and there is a bunch of other work, but I think there is still value in doing so.

I figured self-publishing would be a good bridge. It would allow me to explore marketing a book with my own energy and terms.

Like my blog, this is a great asset to have in my career. My dad badgered me to make a print edition, which takes more work. Digital editions are easy, most of the formatting handles itself, but with a print edition you have to look at margins and a bunch of other things.

I finally got around to formatting the print edition this winter. It is a little self-serving, but it makes a good gift. It makes an impact to be able to tell someone “I wanted you to have this book that I wrote.”

What is one piece of advice you’d give to entrepreneurs watching?

We tend to believe that others act and think in ways that are similar to ourselves.

Even when we recognize that they are different, we are bad at anticipating how people react to a given product or message. It is up to us to try and understand what matters to them, and not make the assumption that they are like us.

When we understand that, that is when we can be more persuasive.

That is great. Jason Shen, where can people follow you?

You can checkout the The Art of Ass-Kicking at jasonshen.com. I’m on Twitter @JasonShen. You can find me as Jason Shen, just about everywhere online. The podcast is tectonicpodcast.com.

Winning Isn’t Normal is on Amazon and available for Kindle. If you don’t have a Kindle, you probably have an iPhone or Android. If you don’t have a smartphone you can read it online at read.amazon.com. Basically there is no reason not to read it. I don’t accept “I don’t have a Kindle as an excuse.”

Posted by:Sam Solomon

I'm a designer, writer and tinkerer. I currently lead workflow and design systems at Salesloft.

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