The story of Reddit is the stuff of movies–or books, at least: college buddies create a social news site that becomes the insanely popular “front page of the Internet,” selling it to Condé Nast and becoming millionaires within 18 months of graduation day. And one of those college buddies, Alexis Ohanian, has written it. Visiting the Walker on January 9 on a tour for Without Their Permission: How the 21st Century Will Be Made, Not Managed, Ohanian gave a rousing TED-style talk on creative entrepreneurship, his work as an investor and developer of new technology projects, and the power of the Internet. But beforehand, as he signed copies of the book, he took time for a deeper discussion of Reddit, the promises of new technology for nonprofits and activists, and the cultural force the site he created with Steve Huffman in 2005 has become.

For those not familiar, Reddit is an online platform for communities. Any of its millions of users can submit links, ideas, videos, photos, or GIFs to any of a massive number of subreddits–themed subdirectories created by users and dedicated to an array of topics, from guns to politics, feminism to the slow-food movement, pornography to cats to religion. Users then can comment and upvote or downvote submissions, with the most-upvoted items making it to Reddit’s front page. On its surface, Reddit looks like a glorified online forum: its design, largely unchanged since Huffman and Ohanian launched the site, feels like a half-step up from Wikipedia and Craigslist. But the genius of it, Ohanian argues, is that participants in the community shape it: they create the subreddits, design motifs to skin their subreddits, contribute new features or fixes for bugs, and serve as community moderators. It’s been a popular formula: last month, redditors in 196 countries participated in more than 7,200 subreddits, viewing some 5.3 billion pages and casting more than 22 million votes. The site saw more than 100 million unique visitors in December 2013 alone.

With numbers like those, it’s no surprise the site has become something of a cultural powerhouse. It’s hatched countless web memes–including Ridiculously Photogenic Guy and Grumpy Cat. It’s influenced life outside the site, from a successful campaign to raise awareness of Greenpeace’s project tracking humpback whales to its vocal opposition to measures like the PROTECT IP Act (PIPA) and the Stop Internet Piracy Act (SOPA) to, more controversially, efforts by users to identify the Boston Marathon bombers–research that proved to be dangerously incorrect. And its Ask Me Anything (AMA) feature has attracted figures in sports, politics, science, and movies–including President Barack Obama and Stephen Colbert, “engineers and scientists on the Mars Curiosity Rover Mission,” and a presidential candidate in Iran’s presidential elections–for open Q&A sessions. That’s where our discussion began.

Paul Schmelzer: In the years since Reddit launched, it’s become a routine stop for more Internet-savvy celebrities and politicians, who often do AMAs. I understand Ann Coulter even did one (although it now appears she’s deleted all of her comments). How’d that go?

Alexis Ohanian: It was a trainwreck.

Schmelzer: What makes for a good one, and why was Coulter’s so bad?

Ohanian: Candor and humanity. That’s not to say she’s not human. There was an AMA a week or so ago by a colonel under Petraeus during the surge, Col. Peter Mansoor (Ret.), and he had just published a book. He did an amazing AMA. The reason it was so great was he didn’t dodge any questions. He answered hard questions in an honest way. People who probably disagreed with him had to respect him for answering so honestly. He’s now a professor of history at Ohio State, and he was asked a question about the Battle of Hoth, in Star Wars and how the Empire should have handled the rebellion. He answered it with aplomb.

If you can think about it more like a conversation with strangers over drinks and less like it’s a PR stop like the Today Show, you will succeed. Where Ann Coulter and others–including Woody Harrelson, he’s another infamous one–failed miserably is that they basically treated it, at least in Woody Harrelson’s case, like a PR stop. So every question was answered by somehow pitching his movie. So it’d be like, “When did you start veganism?” or “Why?” And he’d be like, “Oh, back in 2004, be sure to see Rampart this Friday in theaters nationwide.” It ended up becoming a meme.

Schmelzer: Some of the founding principles of Reddit are radically democratic: a platform that’s free where anyone’s ideas can get more visibility. When you started it, did it cross your mind that you might also democratize the way that we interface with people like celebrities and politicians?

Ohanian: We didn’t think that far, but yes. When I was in college I spent a semester abroad in London. There I got into a routine where every Sunday I’d go to Speakers’ Corner in Hyde Park. I loved it. This was in ’03, during the run-up to the Iraq War. Everybody was there speaking out, from Nation of Islam to people speaking on gay rights to people who were just straight-up crazy, just yelling. And the time, you had Iraqis who had relocated, who were arguing for and against the war. It was such an interesting place, and it really affected me. I thought, this is free speech at work. When I got back home I started a web forum using some phpBB software, an open-source software used to run forums. It had, at most, an audience of maybe 1,000 users. This was not my software–I just took off-the-shelf software–but I was really enamored with it and I know the lessons there helped shape Reddit as Steve and I started thinking about it years later.

Schmelzer: Through the years, Reddit and you, personally, have been involved with using that platform to raise awareness about activist issues, and it makes me wonder how you see open technology as key to social change movements. I’m thinking, for instance, about issues you and Reddit have taken on, from opposition to SOPA, the Stop Online Piracy Act, to the environment (in the form of “Mister Splashy Pants,” a successful campaign to name a whale that’s part of a Greenpeace whale-tracking project).

Ohanian: Oh yes. Greenpeace’s famous little whale-naming campaign. So what has social media done? It’s allowed anyone to have a megaphone. It’s also given historically disenfranchised groups an ability to scale ideas that they previously wouldn’t have been able to without getting in the news. When that activist information was controlled by a handful of media organizations, obviously it was up to them as gatekeepers to decide what was covered and what wasn’t. In the broadest strokes, social media has allowed that. Splashy is one example.

The next big thing probably has to involve money. So Kickstarter has helped facilitate funding of creative projects. And there are new ways to think about how we invest our dollars in things like activism that have changed. Take for instance nonprofits like Donors Choose and Kiva–or newer ones that have just sprung up, like Watsi, which allows for direct payments for surgeries in the developing worlds. If there’s a nonprofit that needs $1,000 to perform a surgery, you know that every penny of your dollar that you give to that girl you’re seeing right there is actually helping her, specifically. It’s a model that’s been around forever, but that records every single financial transaction of the nonprofit. Now you have total transparency of where they spend every single dollar. (Literally: Watsi has a public Google Doc recording every single financial transaction they make.) This change allows someone who’s giving $10 to feel like they’re giving $10,000 because they’re feeling a direct impact.

That’s the shift so many nonprofits are still mired in, because they don’t have technology in their DNA or they’ve been around forever or they’ve got overhead up the wazoo. There’s going to be a massive sea change because newer nonprofits that have the Internet in their DNA are using that technology to bring transparency and accountability. It’s going to be a no-brainer: Do I want to give $10 to the Red Cross, where I know a significant portion of that goes to overhead and advertising, or do I want to give to a project where every penny is going where I think it is? It’s going to be nearly impossible for some organizations to compete in a world where we have instantaneous access to so many things. I mean, if I wanted, I could see a selfie of what Kim Kardashian is wearing right now. The fact that that exists is terrifying, but it shows us that if we have access to that kind of absurdity, why don’t we have more access to things that matter, like where a donation goes or what our politicians are doing?

Schmelzer: You’ll be speaking tonight in an arts center, a place dedicated to artists who are exploring new territories, about entrepreneurship. How do you look to the arts for inspiration? What is the parallel between what entrepreneurs are doing and what artists are doing?

Ohanian: I don’t like thinking about entrepreneurs as special people. Think of all the people who would recoil from calling themselves an artist: “Oh, I’m not an artist, I’m not artistic, I’m not creative.” Similarly, people say, “Oh, I’m not entrepreneurial.” OK, fine, maybe you don’t want to start your own company, maybe you don’t want to live a life as a sculptor, but you are capable of doing this stuff, of being entrepreneurial, of being artistic.

I think the biggest parallel is one that I’ve paraphrased from Adventure Time: sucking is the first step to being sort of good at something. It’s the same. No one starts out an amazing artist just as they don’t start out an amazing entrepreneur. They suck a lot, and they fuck up a lot. It’s having the—not even the courage—but having the motivation. That’s the reason we’re hitting 77 universities on this book tour, because that’s something that I don’t think comes up very often in many curricula—because sucking is not acceptable, right? Because when you fail, you don’t pass the class.

What’s so great about the Internet is that it’s the world’s largest stage and library in one. What the fuck do you want to learn? Do you want to learn Final Cut? Do you want to learn how to knit? It’s there! You can do it and you can share the thing that you’ve created, and the first time you have a random stranger telling you, “Hey, you know what? That’s actually kind of cool, what you made there!”–the first time they buy something off your Etsy store, it’s so empowering. It’s like a drug.

Schmelzer: The idea of failure is so popular right now. Every tech conference out there seems to have a panel where people talk about all their missteps, debacles, and–

Ohanian: Epic failures.

Schmelzer: —epic failures. Everybody’s being really honest and open about it. So: did you fail a lot?

Ohanian: In my talk, I show a slide of the first version of Reddit to show just how janky it looked. That’s a kind of failure. But, actually, our first failure was before we even started Reddit. We had another company called My Mobile Menu, which we worked on for a year. We shit-canned it because when we applied to Y Combinator, which was interested in maybe investing in us, they were like, “No. What are you doing, you idiots? It’s too early for mobile. You can’t build an app on a smartphone right now because the smartest phones are Trios and BlackBerrys. So we’re not going to give you any funding.” And that sucked. So we went out and got drunk. The next morning, when we were hungover, they called us back. Paul [Graham, Y Combinator cofounder], to his credit, called and said, “We still don’t like your idea, but we like you guys. Your idea is hosed; it’s not going to work, but if you come up with something else that’s in a browser, not a mobile device, we’ll let you in and we’ll let you guys figure it out.” That’s where we came up with Reddit. Steve and I talked to Paul for an hour and it came out of that. Our first epic failure was wasting a year of our lives on a company that we shit-canned because it was probably five years too early.

Then, along the way with Reddit, we had so many product launches and feature launches that were just absolutely unused, like the “Save” button or the “Hide” button. The thing we got right: within a month we knew if Reddit was going to succeed it was going to have to be as a platform for communities. At that point, Facebook was still only in colleges, Twitter didn’t exist, and Digg was our biggest competitor.

Schmelzer: I used Digg for awhile but lost interest when they redesigned a few years ago–

Ohanian: Yeah, they totally killed themselves with that. I think at some point Digg realized, “We’re going to hit a ceiling on how successful we can be because we’re just one community.” Steve and I worried that they would copy us and our core functionality, which is: we’re a platform for communities. We assumed Digg would realize they’re fucked unless they allowed anyone to create their own Digg, and they never did. We realized right away that the key to Reddit’s success was in making a platform for multiple communities. You want to start a My Little Pony community? Great! If you hated the existing My Little Pony community, you could create My Little Pony 2 and then people would flock to it. Digg apparently never caught on to that.

Instead they had investors who put in a lot of money and expected big things, and all of a sudden they weren’t growing as fast and Reddit was catching up. So they made a bold change to basically remove any of the user functionality–any user-generated content–from the site. Instead users would subscribe to the RSS feeds of publications. So it’s basically like a shittier Twitter at that point. And that just toasted it.

Schmelzer: I’ve been a Reddit member for seven years now, and–

Ohanian: Woah! Thank you.

Schmelzer: –one thing that hasn’t changed is that I can still be anonymous or have a pseudonymous handle. There’s long been a debate online–throughout the blogosphere and among news sites–about how to build accountability in commenting by requiring users use their real names. It’s interesting to me that you guys have allowed anonymity and you don’t verify users. What do you think anonymity contributes to the discussion or the sense of community on Reddit?

Ohanian: Right. It’s funny how this is thought of in 21st-century technology context when pseudonymity and anonymity have been around since the beginning. Thomas Paine dies unless he can publish Common Sense anonymously in the United States. That’s treasonous, so he publishes anonymously, and it not only helps us with the revolution but lets genius ideas flourish. The Brontë sisters, of course, needed pseudonyms in order to publish in a time in England when women couldn’t publish. It’s really just standing on the shoulders of giants; pseudonymity and anonymity have always had a place in communication platforms. Whether it was the printing press or whatever.

The other sad reality you can see on Facebook: people are sitting behind a keyboard, and even if their photo and their real name are on their Facebook account, and their uncle and their mom and their kids are looking at everything they post, some people will still be awful. It sucks. I think as long as it’s someone not doing something face-to-face, it’s going to be there. It’s the curse of the gift. I mean, the gift of it is that someone can’t talk about being gay in a community where they can’t let their parents know—they need a safe space where they can use a pseudonym or anonymity to have conversations and that’s the gift of it. This has been ongoing, and I don’t think it will ever change.