As a little boy, Philip Kaplan, the serial entrepreneur long known as Pud, was “force fed” Ritalin. Kaplan says this with a laugh, but even today, the 35-year-old 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.
Kaplan’s attraction to the next shiny new thing has led him to start dozens of companies in his lifetime, including F*ckedCompany, which famously chronicled dot.com busts and saw 5 million monthly unique visitors at its peak a decade ago; AdBrite, the advertising sales and services network; and Blippy, a controversial social network that asks users to share their credit card and online purchases.
But Kaplan’s corporate creativity has also taken a toll. He left AdBrite in 2008 after “launching 10 businesses” within the company. “There were 125 employees at the time. No one knew who was doing what. I realized I was creating a lot of chaos.” (Kaplan remains the single biggest individual shareholder of AdBrite, which has raised $35 million, largely from Sequoia Capital.)
Over a lunch of shrimp burritos in San Francisco’s Noe Valley neighborhood yesterday, Kaplan revealed for the first time that he has also left Blippy, which last year raised nearly $13 million from investors, most of whom piled into the company before it even launched.
“I mainly worked on Blippy for about a year, but I purposely didn’t have a title,” Kaplan told me. Pushing his blue plastic glasses frames up the bridge of his nose, he said that he’d always “just wanted to float around the office and help where needed, but now I’m less active, though I’m in the office from time to time and I’m still Blippy’s biggest angel investor.”
Kaplan maintains that Blippy is “doing really well,” having moved away from simply recording what people purchase to inviting them to review the products they acquire. “It’s doing better than most people could do. But it hasn’t, like, exploded into something huge yet.”
It’s hard to say whether Kaplan will notice if Blippy ever takes off. Though he says he’s happy to be free of any corporate responsibilities – “it’s only the second time since I was 13 that I don’t have a job” – Kaplan confesses that he’s running a mind-boggling 20 to 30 businesses right now. One of them is the free email newsletter service TinyLetter, which Kaplan calls “one of my favorite things I’ve ever done.” In fact, he thought the company could potentially “take off really big. But it turns out that not many people need to do newsletters.”
Kaplan also recently resuscitated MoBog, a predecessor to 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 the social networking site that randomly connected strangers from around the world via their Webcams — many of them looking to expose more than their personalities.)
Meanwhile, Kaplan has been developing “little silly” iPhone applications that “are me, making art, just to put it out there and learn how the whole process works.” He speaks excitedly about one in-process application that centers on social networking and that “could, in theory, get big. But who knows.”
“A lot of what I do is sort of put things out there and see if they take off,” said Kaplan as he headed out of the taqueria to program some more from his home.
“[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 [were] to go crazy like F*ckedCompany or AdBrite, I’d probably move everything off the table.”