Tim Hwang: Part Huckster Part Activist On The Internet

Image: Eric Millette for Forbes

His specialty? Concocting far-out ideas, bringing them down to earth and making them work

Tim Hwang was gaming the system as far back as high school, which was only 11 years ago. As a sophomore at the posh Newark Academy in New Jersey he started a group called the Strategic Gaming Forum Syndicate. Fancy name, but “it was just a nerdy, board-gaming club”, says Hwang. To raise money Hwang held bake sales, buying packaged Entenmann’s cookies and cakes and selling them as homemade “at a ridiculous markup”. The kids didn’t mind. Hwang had earned their respect earlier selling them George Orwell parody T-shirts of a smiling Tim in braces with the words Big Tim Is Watching You. “My parents were concerned, but they played along,” says Hwang. “They resigned themselves to doing 100 iron-ons all weekend with me. I made a profit on that one, too.”

Thin and excitable, with spiky black hair and black glasses, the 28-year-old Hwang represents a new kind of web entrepreneur who is equal parts huckster and activist. Rather than seek riches, Hwang seeks legitimacy for digital concepts such as crowdfunding (done), social bots that interact with humans on Twitter (done) and software to automate rote but expensive human functions such as the law (not done yet).

He has yet to hold a full-time job for longer than two years, but Hwang gets more done in a week than most people do in a month. “I have a list of ideas in two columns— Someday and Maybe—that I’ve been keeping since college,” says Hwang. “It’s now 200 items long.” During his junior year at Harvard Hwang started working at the college’s Berkman Center for Internet & Society but grew frustrated with academics who merely theorised about internet culture. Hwang decided to bring internet culture to the campus. In 2008, during his senior year, he created a rudimentary web page for an event he dubbed ROFLcon (ROFL = Rolling On the Floor Laughing) and started inviting ‘memes’ to attend. The first year brought 600 people.

It’s now a biennial event attended by 900 people to meet luminaries such as internet law expert Jonathan Zittrain, 4Chan’s Christopher Poole and the ‘Double Rainbow’ viral video guy. But Hwang lost interest once things went pro. The conference is currently on hiatus.

Hwang stayed on at the Berkman Center after graduation. He and his friends would sit around and complain about the lack of cool things to do in Boston. So Hwang launched the Awesome Foundation. They each threw in $100 to make a $1,000 grant for the creation of something “awesome”. The first grant went to a Rhode Island School of Design professor who applied to make a 33-foot-long hammock that sat in Boston’s Rose Fitzgerald Kennedy Greenway.

Crowdfunding over the web was a new concept at the time (Kickstarter launched in April 2009), and the idea, once online, became a meme of its own. The Awesome Foundation—Hwang loves overblown titles—now has 94 chapters in 19 countries and has given out more than $1 million in grants to more than 1,000 projects, putting Hwang on lists, alongside Bono and Bill Gates, of the world’s most innovative philanthropists. “He uses the power of faceless organisations to disguise the fact that it’s just him working on it,” says Christina Xu, Hwang’s partner on ROFLcon and the Awesome Foundation, where her title is Chancellor at the Institute on Higher Awesome Studies.

Internet marketing outfit The Barbarian Group recognised Hwang’s branding savvy and hired him. But mapping the social influence of cereal maker Kashi didn’t hold Hwang’s attention for long. So he secretly applied to and got accepted at the University of California, Berkeley law school. For six months he held down the marketing job from California without his bosses knowing he was in law school. “I did a lot of studying on airplanes flying to clients’ offices,” he says.

Meanwhile, he kept churning out more internet projects and groups: He named himself chief scientist for the Pacific Social Architecting Corp, which creates ‘social bots’—swarms of automated, credible identities on social media platforms that interact with unsuspecting humans. Pacific Social has spun out a startup that charges hedge funds and retailers up to “six figures” to use its human-imitating bots to conduct market research on Twitter among people who don’t realise they’re being polled (or that it’s being done by algorithms). Pacific Social’s research was cited in an NSA PowerPoint leaked by Edward Snowden.

Last summer Hwang tried again to go mainstream, joining prestigious law firm Davis Polk after graduation. Little did they know that he had written software to handle simple tasks he’d been assigned. He stayed at Davis Polk for only seven months, all the time he needed to lay the groundwork for his own firm, Robot, Robot & Hwang. It’s a joke name, and the firm isn’t real, but Hwang has assembled programmers who will release a free software package to automate the document review and IPO-form-filling work. “I was in it to kill it. I want to replace lawyers with code,” says Hwang.

Hwang’s latest full-time job, as of March, is head of special initiatives at Imgur, an image-sharing and meme-generation site that recently scooped up $40 million in venture funding from Andreessen Horowitz. Responsible for promoting offline networking among Imgur’s thriving 130-million-member online community, Hwang recently spent a week visiting summer camps to find one for a company-hosted meet-up. Imgur CEO Alan Schaaf knows about Hwang’s many hats and doesn’t mind them. “He concocts these far out ideas and then brings them down to earth and actually does them. We’re lucky to have him,” says Schaaf.

How does he manage to get it all done? Hwang as a teenager had to make the transition from an unstructured Montessori to a regimented prep school. So he started planning his days carefully, something he still does, meticulously blocking out each hour of each day. When I met with him one Sunday afternoon in his San Francisco apartment, I was crunched between Brunch and Netrunner Card Game.