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 recently, 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.