Yahoo Is Buying Tomfoolery, An Enterprise App Studio Led By Ex-Yahoos And AOLers

Yahoo’s acquisition spree continues apace, with the next deal likely to cover a few different bases for the company: mobile, enterprise and bringing ex-Yahoo talent back into the fold. We have heard that Yahoo is in advanced talks to acquire Tomfoolery, an enterprise app studio co-founded by two ex-Yahoos and two ex-AOLers. One person close to the situation says the deal could be done as soon as this week. The WSJ is also reporting a possible acquisition and puts the price at $16 million.

Tomfoolery — which opened for business last year with seed funding of $1.7 million from a group of big-name investors (it included Andreessen Horowitz, David Tisch, and a number of Yahoo and AOL veterans including Jerry Yang, Brad Garlinghouse, Ash Patel and Sam Pullara) — has been built around the concept of developing apps for enterprise users built on consumer principles.

The idea is that, in a world full of dry and often tedious enterprise software, adding consumer elements makes the apps more engaging and easier to use, and employees more productive. Tomfoolery’s slogan is ‘Work Awesome’.

The company’s first product was an app called Anchor, a real-time conversation platform. Users of the app can create groups for different threads, for example what to eat for lunch but also progress on a particular project. With a camera button alongside the main text input window, the idea is to be able to upload pictures as easily as you would in a consumer product to help make your points. Anchor also integrated with other popular apps such as Box, Dropbox and Evernote to help make it part of other workflows.

But Anchor was intended, really, to be just that: an anchor. Tomfoolery’s bigger business plan was to produce a number of apps that would work together (think Facebook with separate Messenger, Poke, Camera, Pages Manager and Instagram apps). From what we understand, that’s what it had been doing before Yahoo came knocking. One area I’d heard was in progress was a messaging app.

It’s not clear whether Yahoo would want Tomfoolery to continue along this particular enterprise/consumer trajectory, whether it has another mobile project in mind, whether this would be a talent acquisition that could see the team redeployed in a number of areas, or something else entirely.

All scenarios make some sense.

Last year, Yahoo made a couple of acquisitions that are now part of its Small Business group — Lexity (founded by ex-Yahoo Amit Kumar, who now runs the the Small Business group) and Rondee, a conference calling startup. Adding a team of people that has built a startup around apps for small workgroups would be a logical move to expand that business.

At the same time, Yahoo has its eye on making engaging mobile apps for more than just business users. Of the two dozen or so acquisitions that Yahoo has made since Mayer took over, a large portion have been in the area of mobile. But although Yahoo has been making some decent inroads in updating its mobile apps after years of near-neglect, the company has yet to really hone in on a perennial, breakthrough app — ending 2013, for example, without a single app in Apple’s Top 100.

It wouldn’t be the first time that Tomfoolery co-founder and product head Sol Lipman, who once sold a startup to AOL, would have been scooped up to boost a mobile team. In other words, Tomfoolery’s talent and ideas could just as easily be redeployed into that group.

It’s unclear how much traction Tomfoolery has had with Anchor, or whether it was in the process of raising another round of funding. Indeed, what is more obvious is that the group has a lot of talent in it that extends beyond mobile.

Co-founder/CEO Kakul Srivastava is the former GM of Flickr, who led it during its biggest phase of growth, from 37,000 users to over 50 million by the time she departed. She also played a big role in products like Yahoo Mail in her time at the company. (Like many others, she left and worked with Stewart Butterfield at Tiny Speck before moving on to co-founding Tomfoolery.)

Other co-founders like Simon Batistoni, VP of platform, had a big role to play in how Flickr build out its monetization platform and community aspects of the service (before he also left for Tiny Speck). And the final co-founder, Ethan Nagel, is described as an “architect hacker” who has worked both in enterprise but also mobile.

We are reaching out to both companies for comment and will update as we learn more.