Tomfoolery, A Mobile-First, Consumer-Driven Enterprise App Lab From Ex-AOL And Yahoo Execs, Picks Up $1.7M From Andreessen Horowitz, Jerry Yang And More

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Tomfoolery — a startup founded by ex-Yahoos and AOLers that plans to make mobile-first enterprise apps inspired by the best apps in the consumer market — is opening for business and has is announcing the first round of funding behind it: a seed stage of $1.7 million from Andreessen Horowitz, David Tisch, and a number of Yahoo and AOL veterans including Jerry Yang at AME Cloud Ventures, Brad Garlinghouse of YouSendIt, Ash Patel at Morado Ventures and Sam Pullara at Sutter Hill Ventures, among others.

The funding will be used to build out Tomfoolery’s team — currently six people based in Silicon Valley — as well as develop apps. The first of these has yet to be revealed publicly, but it very much plays on the idea of consumer aesthetics and functionality with work productivity in mind (I’ve seen a preview) — slick interfaces and images, and an API to link out to other services, but also security and the concept of work networks central to the core functionality.

That first app will be coming out in Q2 of this year, according to Sol Lipman, Tomfoolery’s co-founder and chief product officer (and he’s also the former VP of mobile for AOL, which owns TechCrunch).

Tomfoolery is riding two different trends in tech. The first of these is the ongoing growth in “cool” enterprise services that are putting more innovation into a traditionally conservative and staid field dominated by large systems integrators like IBM and Big Tech companies like Microsoft and HP.

“Cool” enterprise startups include larger businesses like Box and Zendesk, but also newer players like 15Five.

The second trend is the rise in “consumerization” in IT. This is often described in terms of hardware and the rise of devices like the iPhone in the workplace. But consumerization has also happened at the software level, where people want to have the same kind of functionality in their work apps as they do in their leisure apps.

Both of these areas are hot for investment, with some of the biggest VCs in the tech industry getting behind enterprise startups and eloquently explaining why this is so important. Lipman says that Tomfoolery’s own seed round was oversubscribed and it had to turn a number of interested parties away for now.

Tomfoolery’s approach to cool, consumerized enterprise apps comes from a decidedly consumer perspective: Lipman’s past ventures have included Rally Up, a messaging network that was acquired by AOL in 2010, and before that 12Seconds — a mobile video service that integrated with Twitter, a little like Vine and probably a little too ahead of its time.

Meanwhile, Tomfoolery’s CEO and other co-founder, Kakul Srivastava, CEO, is the former GM of Flickr and VP at Yahoo!, who was leading the Flickr during its biggest phase of growth, from 37,000 users to over 50 million by the time she departed.

Others in the management team include Simon Batistoni, formerly engineering lead, social at Tiny Speck Inc, head of back-end engineering, Flickr, and senior search engineer, Yahoo!; and Ethan Nagel, senior technical director, Mobile First at AOL, who had joined, like Lipman, after AOL bought Rally Up.

In other words, not too much enterprise experience between any of them — except for the kind that we all have first hand as users of sometimes-defeating software and apps that have been presented to us by IT departments.

While perhaps 10 years ago it may have been inconceivable that people with no enterprise experience would be able to build services for enterprise users, the trends in today’s market seem to indicate the opposite, with even services like Path, without encouraging it, picking up enterprise users on its network.

There are definite tech trends that are at play here, but Lipman says there is another important element behind why they decided to create Tomfoolery. “A lot of people spend more time working than doing anything else,” he told me, “So it’s important to keep that in mind, and make some of that time fun.”

He also thinks that while there have been some services that are making it much easier to for people to get work done — Box’s cloud storage services being one example — this has not necessarily translated into similar usability in apps.

“Enterprise apps have no soul,” he said. “We believe that it’s about time someone built apps for the enterprise that are consumer grade. It’s obvious that the mobile disruption makes the consumer the decision maker in the workplace. They have different needs/desires than the IT manager. They are going to want what Tomfoolery is going to build.”

The emphasis on mobile in that equation is an interesting one: it presupposes that the way that mobile has become a central, and often default, communications medium for consumers is being played out in equal measure in the workplace.

Those of us who sometimes feel chained to our laptops/keyboards/desks might argue otherwise, and so while Tomfoolery is keen to emphasize “mobile first,” it doesn’t rule out that there may be a web or “desktop second” in there somewhere along the line, too.

With the first product yet to be released, Lipman would not talk too much about business models, but he raised several possibilities of how revenue might work: there could be licenses based on user numbers, or another might be for extra functionality within the services — either in terms of extra security, extra storage, or links out to other networks either in your business or those of others that you work with. The big question there will be whether, in the rush to make stodgy enterprise apps more consumer-like, monetization may prove to be similarly elusive/problematic as it is for many mass-market social apps.