Community Builder, Ted Rheingold

Cyd is ecstatic over her new boyfriend, whom she just met offline. “His name is Otis and he’s sooo handsome and sweet!” she tells her cyber diary. Of course one has to question the judgment of anyone whose favorite hobbies include playing with new trash bags.

Cyd, you see, is a pug, and thanks to founder Ted Rheingold C’92, she and her owner have the opportunity to make plenty of new friends.

Rheingold’s three-year-old company (that’s 21 in dog years) is expected to net $2.5 million in 2007 due to the enthusiastic patronage of pet lovers. (Cat owners can curl up at the company’s feline-focused site, Together, the two sites attract three-quarters of a million visitors each month. With opportunities to corral virtual pals for your dog or cat, they resemble an animal version of the social-networking site MySpace.)

Rheingold, who morphed into a web designer after a stint in international development, started to notice all the people popping out cell phones to show off pictures of their dogs and cats several years ago. He also observed how his wife, frustrated over apartment pet restrictions, tried to get her fix of furry faces from the Internet. “I thought it was funny no one had made a good webpage for dogs, and it just kept feeling like the right idea,” he says.

So what possesses a person to chronicle their pet’s every skunk sighting, vet visit, and birthday party—or to spend actual money on virtual presents for other people’s animal companions? Rheingold points to people’s busy, often disconnected lives. “People love their animals so much and they don’t get to spend as much time with their dogs as they want. Even though the dog doesn’t really understand it, I think it helps the human to know they’re doing something for their dog” by dedicating a space to them, he says. “To have someone come to your webpage and in the voice of their own dog to say, ‘Oh my, what a beautiful dog. You must be very lucky,’ to read a message like that is like opening up a surprise gift in the mail.”

And it’s not just about cyber meetings. Dogster and Catster users take their shared interests offline as well. Rheingold described a recent “meet-up” on the South Carolina coast of 100 members and dozens of West Highland Terriers.

One thing that differentiates the site from others that haven’t become profitable is that making money has been a focus from day one, he says. Much of Dogster’s profits come from the extra services sold on the site, such as enhanced pet pages and virtual currency to spend on “treats” for favorite dogs or cats.

Dogster wouldn’t have been possible 10 years, or even five years, ago, notes Rheingold. “In 2003 most people didn’t have a digital camera and in 2004 it was the Christmas of the digital camera.”

Like Larry Smith, he sees in post-“gold rush” businesses such as his own a recommitment to the original premise of the Internet and the potential for sharing information like never before. “That’s starting to get watered down in a pond of some not-so-good projects, but I think there’s still a lot of really great things being done,” Rheingold says. “I think every week we’re going to see web applications that are going to make a room full of people go, ‘Wow, why didn’t we think of that?’”

Today Rheingold and his wife live in pet-friendly digs with Moxie, a Chihuahua-terrier-dachshund mix they adopted from the San Francisco SPCA. In Dogster spirit they post her pictures and videos on the site ( As of late July, she had 98 pals. “She’s pretty popular but we kind of keep it on the down low,” Rheingold jokes. “I’d like to be able to respond to every friend and message and email that comes in.”


Web Cultivator, Josh Kopelman

If you’ve got a start-up company, Josh Kopelman W’93 is one of the folks you want to sit next to on the airplane—or, in Web 2.0 fashion, meet through the professional networking site Linked In. As managing director of First Round Capital, Kopelman has invested in a number of companies that have become Web 2.0 buzzwords, such as the social bookmarks manager, the website discovery service StumbleUpon, and the collaborative-website hosting service Wikia. “But I really don’t say I’m going to look for the best Web 2.0 companies, I just want to look for the best companies,” he explains. He also doesn’t find the term very useful. “I’m a believer that Web 2.0 has become so distorted that it basically means any Internet business that got started after 2003.”

If politely brisk in a phone interview, the busy Kopelman is more expansive on his blog, whose title (“Redeye VC”) plays off his “coastally challenged” status as a Philadelphia-based venture capitalist. “Eighty percent of my portfolio is in California, so I get to travel a lot,” he says. Philadelphia makes sense for him because “it’s a great quality of life and my family is very happy here.”

Kopelman was a Wharton undergrad when he founded an online reference and research service called Infonautics, which was bought by Prodigy. For him there was nothing particularly scary about starting a business as a student. “You can’t really mortgage your dorm room and you don’t necessarily have the same obligations you have later in life. My true cost was giving up on-campus recruiting,” he says.

As it turned out, that wasn’t such a hardship.

In 1999 Kopelman founded the discount marketplace, which was sold to eBay a year later—for $350 million, according to Wikipedia. On the heels of that success, he helped found an anti-spam hardware company called TurnTide, which later sold to Symantec. “I’m not a statistician, but I realized the odds of my fourth company being anything other than a spectacular failure were against me,” Kopelman says. “So I decided I’d rather try my hand as a venture capitalist.”

His favorite part of that job is “meeting with entrepreneurs and hearing their ideas and their pitches.” The hardest part? “Saying no to 99 percent of them.”

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