The Man Known as Pud

In the past 15 years or so, Philip Kaplan has launched—and, in some cases, killed—dozens of companies, from a hot sauce company, to a very short-lived private label porn business, to FuckedCompany.com, which Kaplan launched on a whim during Memorial Day weekend in 2000.

Though never much of a money maker, the site became a famous chronicler of the dot-com implosion and had between 4 million and 5 million monthly unique visitors at its peak. By way of comparison, the blog TechCrunch receives between 1 million and 2 million unique visitors a month, according to the site analytics service Compete.

Kaplan, now 35, seemingly can’t help himself from trying to see what sticks. While he’s interested in making money, he’s much more interested in pursuing new ideas that spring to mind.

“For better or worse, I’m unusual in that I don’t ever care that much about equity,” he says. “I very rarely will fight over a percent or two in a company.”

Indeed, when Kaplan says that “the most interesting stuff is what I’m working on, rather than stuff I’ve done,” one senses he means it. Consider the ad sales and services network AdBrite, which Kaplan launched as a self-serve ad platform for brands looking to advertise on FuckedCompany.com. The company became one of the Web’s largest ad networks, but Kaplan volunteers that he created “a lot of chaos,” while at the helm, including “launching 10 businesses” within the company while trying to steer its growth.

“I definitely had a focus problem within AdBrite,” Kaplan recently told VCJ over a lunch of shrimp burritos in Noe Valley neighborhood of San Francisco, not far from his home. “We’d be building this stuff to make it super easy, then somebody would call and want to do this weird thing, or I’d say, ‘You know what would be cool? Where you could advertise on still images. You’d just put a bit of code on your site that would convert all of your images to Flash, and it’d be like those ads that pop up on YouTube videos, a little overlay like that.”

In retrospect, Kaplan says that much of what the team wound up engineering “probably would have been cool for a different company, but I was [always] like, no, no, we should totally do that, so we built a new thing.”

AdBrite has raised $35 million in funding over the years from Sequoia Capital and Artis Capital Management. Kaplan left the company in 2008 and remains its biggest individual shareholder.

Kaplan also recently moved on from Blippy, a controversial social network centered on purchase information that Kaplan helped co-found last year. The company raised nearly $13 million from a long line of name-brand investors, most of who joined before the company launched, with the expectation that it would cultivate a goldmine of buying data.

“I mainly worked on Blippy for about a year, but I purposely didn’t have a title,” Kaplan says. “I just wanted to float around the office and help where needed.” He calls himself Blippy’s biggest angel investor.

Kaplan insists that Blippy is “doing really well,” but it’s questionable whether he will notice if it eventually takes off. Kaplan has never been prone to staying put for long.

He admits to having trouble focusing for too long on any one thing. “My wife says I’m like a kitten with a ball of yarn,” he shrugs.

Growing up in Bethesda, Md., he says he was “force fed” Ritalin and bounced from job to job. First came the bagel bakery, then the custom stereo job store. Soon it was onto the lumberyard, Radio Shack, a musician supply store called Music Emporium and an internship in publicity at the music label Roadrunner Records.

“I basically called the kids who ran death-and-guts ‘zines, and asked them to interview our bands,” he says.

But Kaplan, a computer nerd from an early age, was also busy running an online bulletin board with hundreds of members. In a 2001 profile of Kaplan in Inc. magazine, his dad recalled that Kaplan’s bedroom door was “across from ours, and all night long we would hear people dialing up through the modem.”

“We had Internet and email early,” recalls Kaplan, who says his dad brought home some of the earliest personal computers, and that he and his brothers quickly moved beyond the spreadsheet program VisiCalc to their own software coding. “We never played catch or anything,” Kaplan says, laughing. “We were basically all inside, programming.”

Life isn’t terribly different today for Kaplan.

Kaplan is right now running a mind-boggling 20 to 30 businesses out of his home. One of them is the free email newsletter service Tiny Letter, which Kaplan calls “one of my favorite things I’ve ever done.”

Kaplan also recently resuscitated MoBog, a predecessor to the popular photo sharing iPhone app Instagram that he founded in 2003, but killed soon after. “It had a Chatroulette problem, if you know what I mean,” he says, referring to Chatroulette, a social networking site that used Webcams to randomly connect strangers worldwide.

Kaplan has also been getting “super into apps” lately and has already developed several, including one called “Punch Your Friends,” an app that invites users to take pictures of friends, then “virtually” punch them by tapping the screen. “I’m just getting my hands dirty,” he says.

Don’t be surprised if one of Kaplan’s many ideas attracts venture funding again.

Kaplan maintains strong ties to many of his VC friends, and in his view, the going will be good for some time to come.

“Are we in a bubble? Maybe a mini-bubble.” But Kaplan doesn’t think it will necessarily end in tears any time soon. “A company that raises $20 million isn’t going to go away for a long time unless they give the money back. So maybe in 2013, [valuations and rounds will] start coming back to earth. But everyday, there are millions more dollars in VC that are on the way out.”

“A lot of what I do is sort of put things out there and see if they take off,” Kaplan says. “[Beyond the companies I’m running] are another 50 that I’ve shut down. Sometimes, if something makes $50,000 a year, that’s cool. It just does its thing and makes people happy. But if a company starts to go crazy again like FuckedCompany or AdBrite, I’d probably move everything off the table.”

Philip Kaplan at a Glance

Born:

Bethesda, Md.

Age: 35

Education: Syracuse University, B.S., Information Management and Technology

Career: Among many other things, founder and CEO, FuckedCompany.com; co-founder and CEO, AdBrite; entrepreneur-in-residence, Charles River Ventures; co-founder, Blippy

Did you know: Kaplan loves heavy metal drumming and plays in a band called Coverflow, a cover band of VCs and entrepreneurs who have only been playing together in Silicon Valley for about a year. The rest of the band includes Raj Kapoor (vocals) from Mayfield Fund; Tim Chang (bass) from Norwest Ventures; Prashant Fuloria (guitar) and Ethan Beard (guitar) from Facebook; and Daniel Kraft (keyboard) from RegenMed Systems.

Co-founder

Blippy

Location:

San Francisco

Founded: 2009

Mission: A service for users amenable to sharing their credit card transactions, then reviewing the purchases they’ve made.

Total raised: $12.9M

Investors: August Capital, Sequoia Capital, Charles River Ventures, SV Angel and numerous individuals including Evan Williams and James Hong

AdBrite

Location:

San Francisco

Founded: 2002, f.k.a. Marketbanker.com

Mission: An automated online advertising company

Total raised: $35M

Investors: Sequoia Capital and Artis Capital Management

Angel Investor

BranchOut

Location:

San Francisco

Founded: 2010

Mission: A Facebook application that helps sort and search where friends, and friends of friends, have worked.

Total raised: $6M

Investors: Accel Partners, Norwest Venture Partners, Floodgate and numerous angel investors, including Shawn Fanning and James Currier

Beautylish

Location:

San Francisco

Founded: 2010

Mission: A social network for beauty products and brands

Total raised: $1M

Investors: SV Angel, Naval Ravikant, Max Levchin, Steve Chen and numerous other angels