This interview is with David Wertime, founder of Tea Leaf Nation, a social media news site covering Chinese current events. (Download the audio recording of this interview.)

Q. Tell us about your background. 

A. Sure. I’m 32, I have an English degree from Yale, a law degree from Harvard, and I was a Peace Corps volunteer for a couple years, as well as spending four years as a corporate lawyer, first at Cravath Swaine & Moore and later at Milbank Tweed in Hong Kong. I recently left Milbank to work on my own startup.

Q.  Tell us how your career path has taken you to where you are today. 

A. I think, looking back, we try to make a coherent narrative out of our career decisions, and sometimes that’s imposing a structure that didn’t really exist at the time. In my case, I think that’s probably a fair description. I made decisions that seemed right for me at the time, but looking back, there are probably a few things that run through as common threads, and a number of things that frankly don’t.

After college, my first full-time job was as a Peace Corps volunteer, from 2001 to 2003. The reason for that was I was really young, and I thought that would be the time to do something really risky and interesting. At the same time, I had the safety of the Peace Corps organizational superstructure that made sure I wasn’t just wandering around China, which is where I served, but rather there was a preset structure when I got there. So I was partly attracted by that combination of structure and risk. I had thought for a long time about being a Peace Corps volunteer; I was attracted by the idea of service and by the idea of representing my country, and doing something that was valuable. Also, the Peace Corps was something that people had heard of, so it was easier for me to explain upon my return what I had been doing in rural China.

I actually left China early, along with all the other Peace Corps volunteers in China at the time, before our stint was up, because of the SARS outbreak, which I think was in April 2003. After that, I went home, took the LSAT, and then ended up going back to China for six months and was studying at a school near where I had served while I was applying to law school.

My logic then was a bit different than when I had applied to the Peace Corps a couple years back. I was looking for structure and didn’t have a clear direction, so I thought law school would help provide that direction, even though I wasn’t particularly keen at that time on the idea of being a lawyer.

After I was accepted into law school, I decided it was an opportunity I didn’t want to pass up, so I decided to go. After law school, I went for what is in some ways the default option, I think, of working at a corporate law firm. You’re courted quite heavily, and you have good opportunities, at least back then when the economy was much different. Again, I used the logic of: I have an opportunity I shouldn’t pass up, because it’s a very good opportunity. That’s why I took the job at Cravath Swaine & Moore.

I also did think that learning about how finance worked was important. Even if I didn’t want to be a lifetime practitioner, I thought that being able to speak that language was powerful, and that instinct turned out to be right.

But moving to Hong Kong, after I worked at Cravath, to work at Milbank was me starting to move a bit in the direction of what I most wanted to do. By that time, I had several occasions to go to China and spend a good amount of time there. I thought it was a very interesting place, and I wanted to get more exposure there.

Finally, the most recent career decision I made was to leave the law and start up my own organization. At the time I left the law, I actually didn’t know precisely what I was going to do. One law firm partner told me at my departure party, in front of everyone, that I was crazy to be jumping out of a plane without a parachute. But by that time, I felt financially that I could get away with it. And I had already thought through all the worst possible outcomes, including that one — i.e., what if every single person tells you you’re absolutely nuts and this is the worst decision you’ve ever made, what will you do? But many people were also quite supportive, which was pleasantly surprising.

But the reason I made that decision was because I felt, financially, I could weather it for sometime, not forever, and also that I had something I wanted to share. A feeling that the things that made me unique, the things I was most skilled at and most proud of, were things I was busy suppressing or ignoring while I was working at a law firm, rather than the things I was relying upon and being called upon to use on a daily basis. So for me, I felt I wasn’t very well-matched, at least for the particular experience I had at that time.

And so I thought with the same logic behind my original decision to join the Peace Corps: you’re young, you have a chance to do something meaningful, if a bit risky, and you can provide a bit of structure — in this case, provide it myself — to hold the risk in and keep it from seeming too overwhelming. And so I took that leap. And that’s where I am now.

Q. What specific steps did you take to transition from a big corporate law firm to starting your own company? 

A. Actually, most of the hurdles were psychological. Many of the steps I took were just getting past certain issues and doubts that I had, or minimizing them enough so I felt comfortable with my decision as a whole.

The big concrete steps were twofold. One step was to save as much as I could, and position myself so that, if I wasn’t able to earn money off the startup right away, which many people aren’t, I’d be able to survive it. And even if I had to find another paying job, if I wasn’t able to turn my startup into a paying job, I’d also have enough time to do that before running out of money. So I think part of it was just watching my spending, watching my lifestyle, and that’s a step I continue to take. I was able to project out what I was going to spend and be responsible about it. Frugality is greatly underrated as a source of freedom. So that was a huge step. The more money I saved — everyone knows corporate attorneys are paid pretty well — the freer I felt.

The other step I’d already taken, which took me a while to realize it, was that I had already gotten a law degree and four years of experience. So for me, I felt that if push came to shove, whether for family or personal or career reasons, if I needed to get a stable paying job, I could do that. So knowing that I already had that law degree, I thought, well, I got that because it was something that would make me more flexible and free and happier, right? It isn’t something that should decide the next 50 years of your life, if you don’t want it to.

Those were the two really big steps. The rest was just engaging with my doubts and trying to harmonize my intellectual outlook with my psychological outlook. I mean, it’s one thing to create a column of pros and cons and say, “Okay, all these cons are imaginary, or these are just fears or are improbable.” But it’s another thing to bring yourself to emotionally believe what you’ve set out intellectually to do, and to have the strength to do it.

And frankly, even when I was absolutely sure — when I said, okay, this is when I am going to leave and this is what I’m going to do — even then, at the very end, I blinked. The night before, I thought, what am I doing? I walked around downtown Hong Kong until three in the morning — I was pretty much the only one out there — just thinking quite deeply about why I was going to do what I was going to do. And then the next morning, I called my older brother and my younger brother, just to have them remind me I wasn’t nuts. So it really does sometimes take a village to convince somebody to do what they might already know they want to do, but they’re scared to do.

There are still times when someone will say to me, “What are you doing? Why are you doing that?” They’ll be very doubtful, and I have to be strong enough to face that. Everyone who starts their own organization has to be strong enough to face that, because until you’ve built something, what you have is nothing. You have to be comfortable with that and rely upon your own confidence and skill, rather than a name or an explanation that will please people.

However, it’s very important to note that, although there’s this idea that as an entrepreneur you’re out facing this cold hard world, the fact is, so many people have been incredibly supportive, not just of me but of Tea Leaf Nation, the website I started. People have reached out and offered to do things just out of the goodness of their heart and out of their belief in what we’re trying to accomplish. And I worry sometimes that when we discuss the need to steel yourself against the doubts, we’re casting it as one person adrift in a sea of doubt. But that’s really not true. We’re held up by so many other people.

Q. Tell us about the experience of building Tea Leaf Nation. What do you do on a daily basis? 

A. Sure, so just by way of background, Tea Leaf Nation is a website that synthesizes and aggregates chatter on China’s social media to give people a picture of what people in China actually think. It’s not a perfect picture, but it may be one of the best pictures we have, since there aren’t free elections in China, or a plethora of reliable opinion polls the way there are in the United States. And I think social media is a really valuable resource. So that’s what we do.

Day-to-day, I’m still a big part of content production. That means literally writing stories, many of which come out of my looking at countless Chinese language tweets on China’s social media, which is a skill I did not have when I left the law firm Milbank Tweed. So it’s something very new to me — both the journalistic enterprise, which has always excited me but wasn’t something I’d ever done seriously, and also learning to feel the pulse of foreign language social media, and it’s an immense challenge.

So I do that on a day-to-day basis, as well as reaching out to people, editing stories, and doing all the little things that usually get done for you at a big established company.

Q. How did you acquire the skills to read and interpret large volumes of tweets in Chinese social media? 

A. First, there is a dearth of people who sit and read and think about Chinese social media for much of their day. So it’s easy to jump a bit ahead of the curve simply because of the uniqueness of what we’re trying to do. In addition, you have a political environment in China that’s not particularly conducive to producing these kind of summaries of what social media means for China’s politics. And so the people who would naturally be most suited to do this, which is Chinese internet users, are not out there doing this, at least not en masse. Obviously, they’d be better at it than I am.

In our case, even though I speak and read Chinese at a high level, I’m lucky my two co-founders were born in China and speak and read Chinese at a fluent level. When things started, they were doing a lot more of the heavy lifting, but in a few months, with day-to-day perseverance, I was pleasantly surprised to find I was able to pick this up. I certainly have a lot more to learn, but generally I feel pretty comfortable now wading through the firehose of daily tweets.

Q. How did you meet your co-founders?  

A. Right, well they’re two friends from law school. We did some extracurricular activities together in law school and knew each other as friends already. They are corporate lawyers in Hong Kong, and we reconnected when I moved to Hong Kong with Milbank.

Actually, as I mentioned earlier, I didn’t know exactly what I was going to do when I left my law firm job. The idea for Tea Leaf Nation came to us when they were visiting the United States in Washington, D.C., and we met up and ended up taking a long walk around the National Mall, and just talking about some stuff that was important to us.

We realized we agreed on some key principles and there was this really interesting phenomenon of hundreds of millions of people using these websites called “Weibo” that had not existed just two or three years before. To me, that was an astonishing development and one I had not been tracking closely. But the more we talked, the more I realized that this might be a real opportunity for us, not just from a business perspective, but to do the things we all believed in.

So I have two co-founders who are employed as lawyers full-time and helping with this when they can. We’re very lucky because we have a friendship that predates the founding of our enterprise by years, and we have also broadly established that we agree on a lot of important questions on what we’re trying to accomplish and what our values are. What that means is we sing in the same key, and there is a consistency of tone and presentation and content on our site, even when we are not directly coordinating. And that is very, very helpful.

Because inevitably there are times in any startup where there are doubts, and it helps so much to be working with people where you aren’t looking into this abyss and thinking, “Well, who is this person, really? And why are they really doing this and what are they all about?” You don’t have to ask those questions. In my case, these were two people I already thought of as really wonderful, brilliant, trustworthy, excellent people. I was just glad to be their friend. And it made it a real treat, actually, to do the startup just from a social perspective, as well as an intellectual perspective.

Q. What do you find most exciting about your current role and what would you most like to change? 

A. What I find most exciting is the underlying subject matter of what I’m doing. It’s nice when we’re recognized; obviously that’s a requirement for us to continue to exist. It’s nice when I know people are reading us and talking about us and praising us. And we really cherish and value every single reader and advocate that we have.

But what most excites me is when I feel like I am connecting with the people who are writing what I’m reading, even though I don’t know them. There is a lot of humanity online, in any country, if you know where to look for it. The things people say, when they write about their families, when they write about their hopes and fears, when they get angry, or sad, or despondent, when you read what someone writes in the morning and you read what they write before they go to sleep, sometimes people are writing about things that are very sensitive often at the risk of getting in trouble, and often people are very funny and sardonic and sarcastic — just to be able to feel like I’m connecting with all these people in some way to help bring their stories to other readers, that’s when I’m most deeply excited. When I think, “This story I’m writing is important and valuable, and I’m helping to shine a light on a place that people otherwise might not see the same way” — that for me is the most exciting part. It really hits what we’re trying to do.

In terms of what I wish I could change, I feel like we’re on a good upward trajectory, but if I could wave a magic wand, I would speed it up. Nothing can ever happen fast enough, especially when you started this organization that’s five months old, that many people still haven’t heard of, and isn’t make money yet. I would of course like to be a big media organization tomorrow, and if I can’t do that I’d like to be halfway there. I’m excited about the way we’re going, but that’s what I would change. It just gets to be a question of time: I can spend a certain amount of time on this, but can I spend 10 years and not pay the bills? No. So the question of time and am I running out of time has to be on a lot of startup founder’s minds.

Q. What do you envision for Tea Leaf Nation going forward and where do you see yourself in the future?

A. I think it’s hard to predict what your career will look like in ten years or even five years. I don’t think I could have predicted ten years ago that I’d be doing what I’m doing now.

But I’ve gotten a better sense in my young career about what I enjoy doing. I enjoy helping people connect; I enjoy writing and thinking about what’s going on in the world. And as long as I can continue to be faithful to those interests and do something I think is good for the world, I’ll be happy.

In terms of what I hope the site will become, I want more readers, more recognition, and more content. I think we’re on the right path, and there’s a few different ways it could go, but most important to me is to be able to continue to represent and create something I can be proud of.

Q. What advice do you have for people who are interested in starting their own company? 

A. For anyone thinking about doing something independent, you’re going to have a ledger, and on one side is going to be the risks and cons, and on the other side is going to be the benefits and pros.

You’re probably not going to be wrong about what’s on that list. But the trick is knowing how to weigh them, because what you are gaining potentially in the future is never going to be as concrete as what you’re giving up now. So when you’re looking to make a risky transition, it requires a lot of internal mental preparation for what you’re going to do.

For me personally, I had the same list of pros and cons about why I should stay in a safer professional environment versus why I should leave. And that list didn’t really change. But eventually I came to realize that I wasn’t assigning the positives as much weight as I should have been.

So I would definitely encourage people to consider that what you are gaining is potentially really huge if you’re really going after what you want, but there’s always the possibility that, because it’s so far in the future, you’re not going to be giving it the weight you should be giving it. And I would urge people who are thinking about making this kind of transition to use their imaginations and trust their instincts.

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