Just a bit over a week ago, reddit announced that they'd finally found a CEO. Now, this wasn't a matter of swapping the old guy out with the new guy — up until Condé Nast spun reddit off into its own thing back in September, the CEO position wasn't one that existed to fill. They picked Yishan Wong, a former Director of Engineering at Facebook (and, perhaps more importantly, a long time redditor) to fill the newly created role.

I've had the opportunity to chat with Yishan about his new gig over the past few days, spread out over a couple dozen e-mails. The full interview follows below.

Well, it would appear that our metric of "finest" here seems to include something like "number of cat pictures." :-)

I'm actually incredibly humbled and relieved that the community reaction was as positive as it was. I would not say that I was terrified, but because I've been a redditor for a long time myself, I was very familiar with how skeptical the community would be of any new CEO (indeed, I would have been myself), so I would say that I was nervous leading up to the announcement.

Now that the announcement is done, I'm able to focus my attention on learning all the subtleties and nuances of the community, as well as the more obscure aspects of how the product functions. I think it's important to know all of those details to be able to make wise decisions. So I am excited; there is a lot of interesting stuff I get to learn now about a site that I've enjoyed for years as a user.

The CEO role is different at just about every company, but I imagine it's particularly strange at reddit. While reddit has had its founders and other key employees, of course, it's technically existed without a formal "CEO" position since it was founded almost seven years ago. What does being CEO at reddit actually entail?

It's definitely unique.

In my case, even during the job search phase, one of the questions I asked them was, "Why does reddit need a CEO? It seems to be running just fine - I'm using the site right now."

It turns out that the answer lies in the fact that for the past few years, reddit has been a wholly-owned subsidiary of Conde Nast, and when you're in that situation, a lot of the mundane corporate functions are taken care of by service organizations in your corporate parent.

Things like finance (including both budgeting and investor relations), legal, HR, desktop IT, are all either done via these organizations or don't exist in the same way. The thing is that those functions were provided to reddit in a style that was very much geared towards the magazine industry, and not a technology startup. For instance, even a simple thing like getting reimbursed for buying the team pizza (a very common thing when it comes to tech startups) was difficult to do because the finance portal wasn't set up for it - they would literally have a checkbox for "flying models to a photo shoot" but not "buying pizza for the team working late." So in making reddit a truly independent entity, there existed a need for someone who could put together those functions in a lean and tech-aware way.

They also felt there was a need for a technology+community product vision and overall strategy-setting. With reddit having recently come out of a period of resource starvation, the team has spent a lot of the last year catching up on technical and community debt - you'll notice the site is pretty stable these days and the engineers are working on more tools for users and mods - but they wanted someone who could look forward into the future and help set forward-looking direction, after we got caught up on things. As a former engineer, I always feel a little funny about this, because it's hard to bring in an outside guy who can "come up with a strategy" (no matter how familiar with reddit I might personally be as a user). I am not a Steve Jobs-type of product guy, I am more about facilitating discourse between key people to distill what's needed - but luckily it looks like that's more of reddit's style anyways; there is no "make a beautiful phone and cram it down everyone's throat" equivalent here.

As you mention, the community's reception of you was mostly positive — but not completely. While many welcomed you with open arms, some users (jokingly) made a "Yishan Sucks" sub-reddit. Another user drudged up some comments you'd made on Google+ months before, using them to portray you as a bit of a jerk. Did this catch you off guard at all?

Hahahaha, awesome. :-)

[As you note], the Yishan Sucks blog is a joke (easy link for readers: http://www.reddit.com/r/yishansucks). It was made by a reddit user whose novelty account is "RedditCEO" and he's had that novelty account for a year already (i.e. even before the independence and CEO search were announced). So basically he's having a field day with this, and I think it's pretty hilarious. The only issue I take with that subreddit is that I mentions that I used to work at McDonalds, which is untrue. I worked at Burger King. It was during my junior/senior years of high school.

As for the Google+ post, I probably was a bit of a jerk. The story behind that is a little weird, and kind of ironic: if you are a Facebook employee, FB doesn't work very well for you because you are densely connected to all your coworkers. As a result, on your birthday you are inundated with so many birthday well-wishes such that your Wall and Inbox are rendered pretty much inoperable for a day. Normal people (non-FB employees) enjoy the birthday well-wishing, but that's because they get a sane number of wishes, but as an employee, the flood is so bad that some engineers I know would turn off their Wall when their birthday rolled around.

Then, with G+, there was this weird thing where if you were an early user and even slightly well-known, they put you on this "people you should follow" list on G+ and you'd get hundreds, thousands of random followers. Combine this with the fact that only a very small number of my friends were on G+, and this resulted in this weird situation where you could either post things publicly (and get tons of strangers commenting, usually unaware of any context or backstory, such that the comment thread would end up being incoherent) or you'd try to post to just your friends (and because so few of them were on it, you'd get very few replies).

So I made that post originally to point out both the ridiculousness of FB and the ridiculousness of G+, and then when the random guy replied with a "happy birthday," I tried to emphasize the point with my reply of "Who/what?" Now, perhaps even more ridiculously, I look forward to next year on my birthday when I will get thousands of troll birthday wishes from redditors.

All of that said, I don't really mind. Those aren't very terrible things - one is a joke and the other is irony piled on top of irony. I had actually anticipated that negative reactions would stem primarily from "zomg he worked at Facebook, will he make reddit like Facebook?" but apparently people have been entirely reasonable about understanding the difference between people who've worked at Facebook and Facebook's policies. I guess this is unsurprising, since reddit is mostly about making jokes and ironic humor. Incidentally, the guy who made the original post sent me a message saying (paraphrased), "Oops, I seem to have riled up a mob against you! Sorry, didn't mean to do that!" I wrote him a reply explaining all this, which he found pretty amusing.

As a long time redditor, have you learned anything that surprised you in your first week behind the curtain? I think the thing that's been most surprising to me is that a lot of how reddit looks like from the outside is actually what's going on in the inside. It's very transparent. The code is open source, and the team often talks to the community and tells them what they're doing and what's going on. So as a result if you are on the outside and you pay even a decent amount of attention, you can tell how things work and what is going on. So I was surprised to find that all the things I'd learned from years of just using the product and vaguely paying attention to the team's blog posts was almost entirely the complete picture of how the company worked. This is very rare for companies.

Also, I was surprised to find that hueypriest [reddit's General Manager, Erik Martin] does not actually look like this.

It's hard to mention your name without someone saying "Oh! That guy from Quora!" with nearly 1500 answers under your belt. With that said, it seems your activity on Quora has tapered over the past few months, with your last contribution going up a few days before you were announced as the new CEO. [Note: Yishan since has returned to participating on Quora.] Is Quora something you're expecting to have to phase out as you transition into this new role, or have you just been busy?

There are kind of two answers to this question.

One is that most people who have jobs don't end up being able to post on Quora very much. If you look at people like Michael Wolfe and Keith Rabois, both were very prolific contributors for a long time when they were between jobs or in transitionary periods, and once they got back to work, their contributions tapered off. I'd definitely say that the busy-ness of the last two weeks has prevented me from spending any time on Quora (I not only have not had any time for Quora, I've gotten behind on a lot of other personal communications as well), and that's likely to continue except for during long vacations (when I'd also rather spend time with my family). It's already happened in the past - I'll work on a project for a couple weeks and ignore Quora entirely, but nobody really noticed then because it's hard to notice the absence of something.

The other is that, obviously, now that I'm an executive at a non-obscure company, I can no longer write flamboyantly incendiary responses to certain questions, especially ones pertaining directly to the industry or other companies, because someone somewhere will re-interpret it as "reddit CEO says X sucks" or something and it will affect reddit. So obviously I will have to tone it down there. But I presume I'll still post every so often, it's one of my favorite sites.

Reddit's former Chief Architect, Jeremy Edberg, recently said that one the most important things for the reddit team to keep in mind in hiring a CEO was that "the value of the site comes from the community, and [that] they are just shepherds of that community." Care to share your thoughts?

Yeah, that is the way I thought of it when I was a user. I'm not sure I would use the word shepherd, because that sort of implies that the reddit community is a bunch of mindless and stupid sheep. Maybe "beekeeper" is more appropriate (especially as it's also often referred to as the "hivemind"), since it can occasionally become an angry swarm and it's all you can do to create a useful environment and hope the community self-organizes and produces something good out of it.

Incidentally, during the early phases of the job search (when I was just having exploratory discussions with the recruiter), I read that answer (he posted it on Quora, no less) and the qualifications he listed read like a description of my resume. So that gave me the confidence to proceed with being a serious candidate. That said, I'd sure like to also talk to some early Google employees who have experience building ad systems too. ;-)

In talking about the interview process, reddit co-founder Alexis Ohanian mentioned that he asked all the candidates a certain question: "Why did digg fail?" You apparently had the right answer. So in your words, why'd Digg fail? What keeps reddit from falling to the same fate?

A lot of people asked this question as soon as Alexis posted that. I anticipate that it will come up in the IAMA that I'll be doing in a couple weeks, so how about I leave this one unanswered so that I don't spoil it for the redditors then? :-)

Bah! Fine, here's another question you probably can't answer. :) Where would you pin the odds of Reddit acquiring the much lauded, user-made Reddit Enhancement Suite plug-in? If Steve Sobel or Daniel Allen [the guys behind the project] came looking for a job, would they be good to go?

That's a fairly specific question, and it would take a lot of looking at reddit's product needs, the community's needs, and RES itself to be able to answer it, so I can't give a definitive answer right now - acquisitions are more complicated than most people think, so you can't just be like "Oh yeah, we're gonna buy so-and-so."

For now I can only say that I really like using RES, and it's one of the most common suggestions I got after the announcement about the job went public.

What's the biggest challenge facing Reddit in the near future?

This is something I'm still working to gain a thorough understanding on in my position as CEO, so instead I'll answer that from my perspective as a user.

I don't think reddit is facing any enormous existential threats at the moment. In the past, there were times when it was very fragile, when it toiled in the shadow of a much larger competitor, but it's proven itself to be a fairly viable entity and potent force on the web now, with a robust community behind it and several promising avenues for revenue. So I would say that at this point, there are a couple obvious major hurdles to surmount:

1. Continue to provide the community with better tools to self-moderate and organize. While I think that from some angles, the reddit community is seen to be very chaotic and unpredictable, there is actually a remarkable amount of emergent organization and civility that's emerged primarily via convention and culture. Clay Shirky (I think it was him) once said that online communities face two types of problems - technological ones and social ones - and you can't solve social problems using technology (i.e. features). reddit's community has been self-organizing in the way that real offline civilizations are, and I feel like the role of reddit-the-company is to provide the right framework of tools that fits within this self-organizing phenomenon but knows its own limits.

2. Revenue model. reddit actually has a number of potential revenue models, all in varying states of maturity. While our new structure allows us the ability to take investment, it's not clear that would be the optimal path for reddit, because venture funding can come with certain expectations that can skew your priorities. I would be most comfortable if reddit were financially self-sustaining because it would give the company the flexibility it needs to make long-term investments in its platform and community products. So closing that gap seems like a worthy goal, and eminently doable.

Can you think of anything in reddit's recent history that you'd have done differently?

No, to be quite honest, one of the things that helped convince me to take the job is that I felt the judgment of the team was very sound, and seemed to be a pretty good cultural and philosophical fit for me. They have had to make a number of big calls recently on high-profile issues and I think in each case they navigated some very tricky terrain and did it quite well. Having been at Facebook and seen what I've seen, I would say this is very rare for such a small startup and really speaks to the conscientiousness and maturity of the team.

Thanks Yishan!