Ricky Van Veen
Josh Abramson and Ricky Van Veen were 18-year-old college freshmen in 1999 when they started bumping into dot-com entrepreneurs while DJing at various parties and Bar Mitzvahs.
"We got a taste of that world, so we did what came naturally," says Van Veen, now 29. They started posting jokes, photos and links—all of the sophomoric variety—on a site they named CollegeHumor.com. "When we weren't really doing our homework, we were doing this," says Van Veen. "And that was a lot of the time." Slacking off started to pay off, first in a big audience, then in cash. Barry Diller's IAC bought 51 percent of CollegeHumor in 2006.
Since then, the site has shifted from being mostly an aggregator to a hub for popular video content. And Van Veen has done the surprising thing—stick around after being acquired by a media conglomerate. "If it had been someone other than Barry Diller, I probably would have left," he says. "But I like working for him. If he thinks we have a good idea, he says, 'Go do it.'"
iPad, Kindle or Book?: iPad
First thing you do every day?: Check my e-mail on the iPad next to my bed
Digital media's biggest challenge: Creating a differentiated product that people will pay for
Personal hero: Larry David
What are you going to be for Halloween? Either a name dropper (a costume made up of "Hello My Name Is" stickers that fall off throughout the night) or Hall & Oates (both at once)
When he was 23, Ben Lerer noticed something odd about city guides like Citysearch and Zagat: "My mom and I were supposed to read the same stuff."
He and college buddy Adam Rich went to work fixing that with Thrillist, a curated city guide with the frat-boy sensibility of Maxim.
Thrillist was born as a new-school digital publishing venture that used the decidedly old-school approach of an e-mail newsletter. The thinking was that e-mail is ubiquitous, and a subscriber is much more valuable than a random passerby on the Web.
There was a handy model for success: DailyCandy, which had blazed the trail with a successful e-mail-driven curated guide for urban woman. "If someone welcomes us into their inbox, it's a meaningful connection," Lerer says.
Rich and Lerer, the son of Huffington Post co-founder Kenneth Lerer, took a round of financial backing from Bob Pittman's Pilot Group, also backers of DailyCandy. The 70-person, New York-based Thrillist now publishes versions in 19 cities and has 2.2 million subscribers. Its advertiser base includes marquee brands like Absolut, Tommy Hilfiger and Cadillac.
Thrillist commands CPMs over $20 and is on course to generate $10 million in revenue in 2010. Earlier this year, it made its first acquisition, scooping up flash sales site JackThreads. Thrillist also diversified its distribution with an iPhone app and pending Web site relaunch.
Lerer says there isn't enough money being spent in the digital space and that "there's still so much money being spent on print and TV and radio...these deteriorating mediums." —Brian Morrissey
Biggest mistake: We'd get bogged down and didn't move as quickly by being perfectionists.
Personal hero: My father
First job: In college I teamed up with a friend at a competing fraternity to organize parties. I ended up making all my spending money.
Co-founder, Invite Media
Like many college sophomores, once Nat Turner got most of his required courses out of the way, he started to think seriously about his future. For most sophomores, that typically means picking a major. But for Turner, that meant seeking venture capital funding.
Turner had just completed an internship at the rich media firm VideoEgg. Instead of hoping to land a job there down the road, he came away determined to launch his own company in the video ad space. "I had all sorts of ideas," says Turner, now 24. "I'm very entrepreneurial. It never really seemed weird to me."
Turner landed an angel investor and set to work. Over the next year, as he and partner Zachary Weinberg continued to tinker with their Web video platform idea, they met with multiple advisors in the industry who opened their eyes to the myriad challenges in the display business -- including the need for better technology to manage inventory purchased on ad exchanges.
"They kept saying, 'Every ad agency needs this,'" Turner says.
After two years of around-the-clock labor, Invite Media was born. The demand side platform is used by every major agency holding company. This past June Google bought the company for $70 million. That summer internship seems to have paid off. —Mike Shields
Blackberry, iPhone or Droid?: Blackberry
First thing you do every day?: Check my Blackberry
Last book you read: Zen and the Art of Motorcycle Maintenance
Last movie you saw: The Social Network
Hero: Richard Branson