After Blippy, Pud Contemplates His Next Move

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.”

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17 Comments

  • [...] tells PeHub, which first reported the news, that Blippy is “doing better than most people could [...]

  • [...] tells PeHub, which first reported the news, that Blippy is “doing better than most people could [...]

  • Wow, that piece is completely unbearable. Not the writing mind you, but the subject. Hard to imagine you were able to keep your lunch down while listening to this guy. Experimentation and iteration are all fine & well, but this guy is too casual and cool for reality. Good for him that he’s made a buck or two, but good luck to those LPs funding the investors that send capital his way.

  • thanks for reading, boring east coast guy.

    i can see why you’d find kaplan insufferable. for what it’s worth, he’s actually a really pleasant and, i gather, brilliant, guy; he’s just too prone to chasing ideas to run an organization (for long).

    it’s something he readily confesses. he told me that “much like an artist is painting a picture and they might not be good at management or finance, but it’s their f*cking picture? that’s kind of how i am.”

  • Insufferable or not he does not seem to make money off his ventures.

  • How can a guy who is not “corporate” and not a management type run 20 to 30 different companies?

    I get the concept of being an idea person, or an entrepenuer – but ti seems like this guy is all over the map. I think it’d be a nightmare to work for him because there’s no stability or dependability (at least – that’s how it looks to me).

    Kind of makes me think of “Jack of all trades – master of none”.

  • Bipolarity and blue frame glasses is no way to go through life, son.

  • [...] whose departure from Blippy was first reported by peHUB, says he stepped away from a full-time position with the startup several months [...]

  • [...] whose departure from Blippy was first reported by peHUB, says he stepped away from a full-time position with the startup several months [...]

  • [...] whose departure from Blippy was first reported by peHUB, says he stepped away from a full-time position with the startup several months [...]

  • [...] whose departure from Blippy was first reported by peHUB, says he stepped away from a full-time position with the startup several months [...]

  • POP A CAT
    PITTER PAT?

  • He makes much less money than he would like you to think. You should check your facts, Connie, before merely accepting what Philip tells you. The figures about users and money in this article are numbers he spits out insecurely. They are exaggerations like Al Gore’s, and are not real. Nice guy, but he is no “artist” and no successful entrepreneur.

  • a n a l ?

  • [...] peHUB » After Blippy, Pud Contemplates His Next Move Description : Private Equity Hub (peHub) is an interactive forum for the private equity community, which includes venture capitalists, buyouts professionals, attorneys, bankers, entrepreneurs, MBA candidates studying PE, and assorted hangers-on. http://www.pehub.com/100438/af .. [...]

  • [...] peHUB » After Blippy, Pud Contemplates His Next Move Description : Private Equity Hub (peHub) is an interactive forum for the private equity community, which includes venture capitalists, buyouts professionals, attorneys, bankers, entrepreneurs, MBA candidates studying PE, and assorted hangers-on. http://www.pehub.com/100438/af .. [...]

  • [...] whose departure from Blippy was first reported by peHUB, says he stepped away from a full-time position with the startup several months [...]

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