ReadWriteBuilders is a series of interviews with developers, designers and other architects of the programmable future.

Alexis Ohanian took on the challenge of building the “front page of the Internet” by co-founding the social platform Reddit in 2005. Reddit has blossomed into one of the most popular social sites on the web, boasting over 80 million unique visitors a month.

Ohanian went on to help launch the travel site Hipmunk and the social enterprise site Breadpig. He is an outspoken advocate for an open Internet, and last year blacked out Reddit’s front page in protest against Hollywood-backed bills that would have allowed the U.S. government to unilaterally blacklist alleged pirate sites from the Internet. (Congress abandoned the legislation following widespread Internet protests.)

He’s best known for Reddit, a site famous for launching viral articles, images and videos on the strength of “upvotes” from its huge user base. The site’s “Ask Me Anything” sessions, known colloquially as AMAs, have brought celebrities, politicians, scientists and CEOs to answer questions posed by Reddit users. Participants have included Bill Gates, Madonna, Stephen Colbert, Psy, Rachel Maddow and President Obama.

Ohanian’s new book, Without Their Permission, details how he became an entrepreneur, a story that he hopes will resonate with young people who are thinking of starting their own businesses. “I want to knock entrepreneurship off its pedestal,” he says. “I’m taking the book tour directly to millenials, the people that are forced to create their own careers.”

I sat down with Ohanian to talk about some of the challenges he’s faced along the way and some of his most exciting accomplishments. (Adopting a cat, he said, is one of them.)

The Hard Way

ReadWrite: What inspired you to start Reddit?

Alex Ohanian: Well, failure. When I was a junior at the University of Virginia I was on track to be a lawyer, and I was obsessing over my GPA and all that stuff. And then I went to a Waffle House. I walked out of an LSAT prep course and into a Waffle House and realized I wanted to not be a lawyer, and that I’d better come up with something else.

I started talking to my friend Steve [Huffman] about ideas he had for technology that I thought we could turn into a business. And one in particular that I really liked was ordering food from your mobile phone so you wouldn’t have to wait in line. That was the one I got really hung up on, I really liked that one. I told him we could make a business out of it. We started here in Charlottesville, and spent about a year building it, and then we got a chance to interview at Y Combinator.

There were a bunch of fortuitous things that happened along the way—you’ll just have to read my book to find out about them. [Winks]

We interviewed at Y Combinator for the first round of YC ever. That night they rejected us.

So the next morning we were hung over on the train ride back to Virginia and Paul [Graham] calls my cellphone and says, “Listen. We like you guys but not your idea. So change your idea and we’ll let you in.”

After a year of building this company, we were ready to quit it. We went back to Boston and met with Paul for an hour to see what we could work on. It was 2005, so there were no smartphones, there was no App Store, so there was nowhere for this app idea that we had. He said, “Just make something on the Web, because you can build there and solve a problem you guys have.” Steve was using Slashdot all the time, and I was just using a few websites. Neither one of us felt like we had the solution to what was going on in the world.

To Paul’s credit, he coined it. He’s like, “You guys need to make the front page of the Internet. And we’re like, “Well that’s ambitious, but okay.”

The only thing we’d finished when we had started Y Combinator was the mascot, and I was convinced I wanted to call it Reddit. Steve and Paul needed a little more convincing.

We got building, and I would mock stuff up in PaintShop Pro 5. I actually saved some of the mockups; it’s pretty embarrassing. We would sort of fight over features that would actually make it to the live site. Three weeks later we launched and put it online. We started getting our first users, like bugging our friends to use the site. And it just went from there.

RW: Speaking of mascots, my editor wanted to know: Why are your mascots so cute?

AO: I don’t know, I like cute things. I don’t think I would consider myself a designer; I think I’m maybe a mascot designer. I’m pretty proud of that. All of these are consumer-facing businesses. The thinking is: We are simple people, we have lots of distractions.

I hope the people with the Reddit alien tattoos never regret them. I’ve met quite a few of those people and it’s really awesome. I haven’t seen any Hipmunk or Breadpig tattoos yet.

It helps because it personifies the brand and sort of personifies the company. With Hipmunk, I think it was even more valuable because it’s an anti-social product. With Hipmunk, you’re sitting there booking a flight, which really sucks, looking for a hotel, which really sucks, so it’s not social at all. Having a mascot was a way for people to say “Oh look it’s cute and happy and trying to fly!” It provides a little bit of mirth to an otherwise bland experience.

The Secret Of My Success

RW: So, apart from the adorable mascot, what do you think drove the success of Reddit?

AO: I don’t know. There were a lot of things. I mean, obviously luck played a role in it. Also, Steve and I hadn’t heard of Digg until after we launched.

I emailed Steve and Paul with the subject line: “Meet the Enemy” and the body was “digg.com.” I had obviously not done a very good job with the competitive analysis, and we had this competitor that had been out for seven months, had raised funding, had a tech celebrity founder.

But it was so helpful because there were half-dozen Digg clones basically just copying Digg, and they had all died because they weren’t doing anything innovative, they were just straight up copying. Because we were ignorant, we built a very different platform.

We built a platform for online communities. User-created subreddits was the growth strategy, and by month two we had decided that was how we were going to grow. We actually thought for a while Digg was going to copy user-created subreddits. If they had, they might still be around, because they had a much larger audience for the first five years. They were the darlings of the tech press. We were never covered in TechCrunch until the day we got acquired.

It always pains me when founders are always trying so hard to get TechCrunch launches, as if that will make or break your company.

We just started building it and thought, this is the way things should work. The way the front page worked, the way the commenting and voting system all worked, that was different from anything else online in the way we brought it all together. Ultimately, these created subreddits.

We have a subreddit right now that talks entirely about Mexican politics. I have no idea what they’re talking about, and even if I was better at Spanish I still wouldn’t know because it’s so cultural and so local. Just like the Brony communities have their own jokes and references. Every one of these subreddits has its own community. There is no way we would have grown to 70 million unique visitors if we were trying to be one front page for everyone.

I mentioned luck was the very first thing, and that undoubtedly plays a role too. As much as I want to give the mascots all the credit.

RW: Had you done a better competitive analysis and found Digg, would you have still moved forward?

AO: That’s a good question. I don’t know. Well, we probably would have, only because we had an advisor like Paul at Y Combinator. His response to the email was, “Don’t worry. Competitors will always defeat themselves before they defeat you, or you’ll defeat yourself before they do.”

I’m sure that’s what he would have said had we learned about them sooner. But don’t get me wrong, as a 22-year-old fresh out of college it was frustrating. It took a lot to keep myself from caring.

That’s exactly the kind of thing that I worry turns some founders away, and that’s why I can’t help but bring up how important it is to just not care about your competitors. Incumbents are rarely a threat. It’s always going to be some upstart that’s drinking your milkshake. It’s not going to be someone who’s already in the market.

For Love Or Money

RW:What’s been your biggest accomplishment?

AO: I don’t know. I adopted a cat. I was going to name her Upvote, but that was downvoted by my girlfriend.

I really try not to celebrate this stuff very long. It took six months for us to get our first press. Bizarrely, it was from the Guardian. A British newspaper was the first major publication, including tech blogs, to ever write about Reddit. From that point on, I always sent it home to my parents because I didn’t really want to think about it. I try not to dwell on any of this stuff.

Alexander Graham Bell can’t walk around—well he’s dead, but—he couldn’t walk around thinking, “Oh man, every single life-changing phone call, I saved every one of those lives!” Any Twitter founder would be an idiot for claiming credit for the Arab Spring. People are the ones who have been always doing these amazing things, but haven’t necessarily had a platform that scaled them to the rest of the world like there is now. Reddit is one of those mechanisms on that platform.

I want to keep striving for something that I can be more proud of in the future. Maybe one day that will be having awesome kids, but there’s obviously another part of that equation I still need to figure out. I’m trying to teach my cat how to sit, which will be amazing if I can pull it off.

RW:What do you have to say about the community coming together as a social group and organizing either to find criminals, like after the Boston Bombing, or to raise money or even pizza for causes?

AO: At the end of the day, people are the ones responsible for the great stuff, and all the not-so-great stuff.

The vast majority of the time it’s benign or good. It’s either just a random cat photo, or it’s a really amazing thing like sending pizza to a bunch of kids recovering from chemotherapy. For all of history and all of humanity’s future, there will be well-intentioned people that when they are told by an authority like the FBI that they are looking for leads, there will be people who are going to try and help.

Casualties Of War

This is one instance that I would argue most of the actors were well intentioned. When asked by the FBI to assist, they did so in a way that was ultimately really off. It’s something we’re still trying to figure out. The New York Times Magazine did a really thorough breakdown of the actual timeline of everything that happened over that period. A couple of journalists tweeted out corroborating tweets that were taken at a whole new different level of legitimacy.

What set things off was a random person on Twitter that created a fake account with a pseudonym tweeted out, “I just heard on the Boston Police scanner that this person is a suspect.” And that random tweet from some random person whose account has since been deleted was what really set things off.

So it’s really tough because I don’t care what the social media platform is, whether it’s Reddit, Twitter or Facebook, you are ultimately going to have people who use this soapbox inappropriately, whether it’s intentional or not. I’m happy that Reddit has formally made a policy of not doing this.

It was really interesting, there was this satirical one that went up that wasn’t actually identifying people. Basically, it was a social commentary on what happened after the Navy Yard shooting. What was so disappointing for me was that all of the media outlets that covered it covered it as actually legitimate, just so they could wag their finger and be like, “Look at that! They’re at it again!”

If they had just taken a minute to actually read what was on there, they would have noticed it was satire. I think we all have to be careful, but especially people who are professionals, you’re not making a very good case when you’re not even taking the time to find out it’s not true, because you’re so excited to get 100,000 page views out of this post wagging your finger.

We are in a new territory that we have never experienced before. But there is a vast amount of evidence out there that the majority of things people use social media for is either benign or good. There’s an onus on us to be good stewards of this, but there’s only so much that all we can do. You can’t blame the USPS for junk mail.

Spin City

RW: How do you feel when you see news organizations citing sources on Reddit?

AO: I’m mostly happy because they’re actually citing it. Because for years, so many newsrooms blatantly ripped their content off it, I’m just happy they’re citing it. Instead they would just harvest it and not actually link back or give any attribution.

There are instances when the Reddit platform becomes a source of primary information. Every day there’s another celebrity. Like, Madonna comes on for an amazing AMA, and Snoop Lion shows up. Of course I get my Google News alert the next day, and there are a dozen blogs that have pulled “The Top 5 Things From Madonna’s AMA.” It’s wild. I’m the dude that spent six months just trying to get anyone to care about Reddit, and now I just get excited when anyone attributes Reddit. But there is still a ways to go.

Reddit is a truly global platform. 70 million people is great, but I want the Mexican politics subreddit to be the place for people to go to find out about Mexican politics. I want the Mexican politics satire subreddit to be the Mexican Daily Show equivalent. Just the fact there is a subreddit where people are just debating, and discussing and laughing about Mexican politics all in one place right now is just cool.

That’s the kind of thing you can only hope for when it’s you and your buddy Steve in an apartment in Bedford, Mass., staring at each other every morning listening to Gwen Stafani’s Holla Back girl, which we did. We only hoped that one day the platform would have arrived and gotten to that point.

RW:Who is the most interesting person you’ve had for an AMA?

Snoop Lion’s was amazing. I was pleasantly surprised by Ethan Hawke’s. The President of the United States is pretty freaking cool. The one who we’re trying to get now is Putin. I would have loved Edward Snowden, I was really disappointed he wouldn’t do it.

Back To The Future

RW:So, you founded a couple of companies online, and it’s been a few years between them. Do you think it’s harder or easier to start an online company, especially a social site, in today’s world?

AO: It’s definitely harder. Particularly user-generated content or a social media site. Just because the market is already so saturated with things vying for our attention, that just didn’t exist back then.

Right now you’re already competing for people’s attention with Facebook, Twitter, Tumblr Reddit, Pinterest, Instagram, Vine, Snapchat, Frontback (I guess is the new thing), there’s a lot.

And there’s always going to be another breakout every year that’s the new thing, and we’ll say “Oh, how did we live without this?”. But that is a hard route to take because you have to make such a compelling case to have done something so new because a lot of it has to come down to this timing, and a kind of serendipity.

RW:What is your favorite part about being an entrepreneur?

AO: The best part is the flexible schedule. It’s such a cliché, that feeling that you’ve never worked a day in your life. Don’t get me wrong, I get up some mornings and I’m exhausted. But the flexibility and the freedom of it, I can never go back.

RW: And the worst part?

AO: Is there a worst part? The curse part of it. I have a lot of trouble with the boundaries between working and not working. But it’s something I always work on. In the beginning, when you’re worried about having money in the bank, the weight of it emotionally is really draining. You wake up in the morning and think your company is going to take over the world or go out of business. That’s the thing that most entrepreneurs have to deal with. And I’m lucky because of the success that I’ve had. It provides a certain amount of safety and comfort.

The reason I’m doing 150 stops on my book tour is because college students and recent graduates have the most freedom because they have the least to lose. And most of them don’t have dependents; most of them have this one opportunity in their lives when they have the least amount of external pressure and responsibility.

We were lucky when we started as founders and graduated, we never knew what it was like to have vacation time or a good salary. We never knew what that was like so we never knew what we were missing. As long as we had beer and pizza, we could start a company.

RW:A little different than being a lawyer, I imagine.

AO: Oh, yeah.

Reddit stickers image via Flickr user Eva Blue. Mascots image via AlexisOhanian.com