Mr. Webb

The Undercover Ad Man

Of all the “if you build it, they will come,” social media platforms like Facebook and Twitter, Tumblr seemed the most advertising-averse. Floppy-haired founder David Karp memorably betrayed a visceral distaste for the stuff. It “really turns our stomachs,” he said in 2010, following that up with a vow not to become “wildly profitable” by slapping an AdSense ad on the otherwise elegant dashboard of all 80 million Tumblr blogs. But it seems as though the microblogging site’s methodical approach toward making money has paid off—thanks in part to guidance from Rick Webb, a 20-year veteran of the ad industry and co-founder of digital consultancy Barbarian Group, who was attracted to Tumblr for its aversion to the “crap” ads that permeate the web.

Tumblr, founded in 2007, released its first paid products (Radar and Spotlight) earlier this year, which offered, “exactly what people wanted, the ability to amplify the message to a larger audience—but they hadn’t built a business around it,” he said.

Not long after Mr. Webb’s arrival, Mr. Karp was showing up on Advertising Week panels next to reps from Pepsi, convincingly crowing about the “brave new world” his platform offered for “native” ads—Silicon Alley’s new favorite synergy. (Unlike intrusive interstitials or annoying banners, native ads help brands capture users’ attention by forcing them to act like any other publisher and create content worthy of getting passed around.) “All we do is ask for your birthday,” said Mr. Webb. “We don’t sell ads against you getting a divorce or getting engaged; we’re trying to do it without selling the soul.”

And unlike the fall 2011 Fashion Week flameout, in which brands eager to advertise on Tumblr were turned off by the dearth of ways to measure the effectiveness of their efforts, Tumblr now has analytics options. One is an in-house service that shows off the impact brands can get from ad-spend metrics—like how long your post lives before it stops getting reblogged, which the company is eager to show off. Union Metrics, which offers a similar service for Twitter, has also licensed Tumblr’s firehose of data. Its service, which is currently in beta, helps brands capitalize on where conversations are happening with their product and influence pick-up.

During Mr. Webb’s short tenure, Tumblr hired its first global head of sales, poaching Groupon’s senior vice president of sales Lee Brown. Listed beneath the site’s many job openings for engineers, you now see postings seeking “evangelists” in ad-friendly categories like consumer electronics and home decor. “We’ve had people come up to us like, ‘Don’t ever put ads on the platform!’ Well, we must be doing it right, because we already do,” he said.

As for Mr. Karp’s infamous queasiness, Mr. Webb said that, as a product guy, “David was speaking as individual who uses the internet and watches TV. Every once in a while, one of the TV ads surprises and delights you. How often does that happen on the internet?” Part of the reason, he went on to explain, is that the $50 billion in brand advertising on TV “is not moving over” to the internet, where it’s still direct advertising. But in a way, Tumblr’s insistence that advertisers go native and use the same tools as users—eschewing invasive behavioral advertising or geotargeting—has helped attract big clients like Adidas. Consumer packaged goods and automobile companies are also coming onboard, making Tumblr suddenly feel up to the size of its $800 valuation.

Right now, noted Mr. Webb, it’s “only really appropriate for big brand advertisers looking for a large demographic. Can we ever just buy America? Can we ever just buy Brazil? That is probably a thing they would like to do.”

Next: Deborah Estrin, CornellNYC Tech: the Entrepreneurial Egghead

Back to the beginning.

Mr. Windolf (twitter.com)

It's billed as an iPad magazine, but Punch--which we first reported on last week--is less a magazine than it is a clever collection of culturally relevant apps and games. Revolving around pop culture topics that range from the highbrow ("Hedge Fund or Organic Farm?") to the low ("Closet Case," where you can dress up a paper doll version of Rick Santorum), Punch is a re-imagining of the iPad format, delivered to us by a cabal of Manhattan media folks, including Daily Candy founder Dany Levy and former Radar editor Maer Roshan.

Now, Punch has announced that it has tapped Jim Windolf to serve as the mag's first Editor in Chief. Mr. Windolf has a long-established media career--he'll be leaving his position as a contributing editor at Vanity Fair, where he's served for over a decade, to join the Punch team. (Spoiler: he also worked at the Observer for nine years before joining Vanity Fair.)

"I feel good about it," Mr. Windolf told Betabeat by phone. "I wanted to learn something new and didn’t want to get stuck on Print Island in case that’s going to be overwhelmed by digital media. When David Bennahum showed me the prototype they had of Punch it blew me away. It gave me a lot of ideas, and it looks like fun."

It will be interesting to see how Mr. Windolf will fare with the transition from the world of print, which he's worked in for over 20 years, to an entirely digital publication. But considering his breadth of experience, and the enthusiasm he has for the new medium, we'd say Punch is lucky to have him join the team.

To learn more about Punch, check out this video the team created to explain it, which made us actually l-o-l.

This will go great with our Sonar

The newest version of Apple's mobile operating system rolled out today, and foursquare is leveraging the new technology to launch Radar, the first passive feature the company has ever released.

"Up till now, you had to open the app to learn what was going on around you. A lot of times you had to check in before you saw what friends were in your area," said Alex Rainert, foursquare's head of product. "Now we can deliver users information that is contextual and relevant without them having to do anything at all."

So for example if a foursquare user is in a new part of their city and walks close to a restaurant on their "To Do" list, the phone can ping them with an alert. During a night on the town, the Radar feature can sense when a group of friends has checked in close to a user and give them a heads up.

"This is the next stage in the evolution of foursquare," said Rainert. "The hardware and software have finally caught up to our vision of making it easy and fun for users to get more out of the world around them."

Along with foursquare's new List feature, this goes a long way towards making the service a powerful tool for travelers who want help exploring a new locale. And for heavy users who don't mind a few push notifications, this turns the app into a powerful, passive sensor for the nightlife around them.

Now if only we could get iOS5 to download...