Meet Tomfoolery, The Company Trying To Make Work Awesome

As technology further blurs work and life, how can we make sure the software we use for work is cool but not creepy? A company called Tomfoolery is trying to find out.

“This is our office.”


Kakul Srivastava gestures to her iPhone 5 as she describes the current setup of her startup, Tomfoolery. The company, which has been stealthily building enterprise apps for the better part of a year, has just 10 employees, a third of whom works remotely. Like many companies that exercise flexible telecommuting policies, Tomfoolery is lucky to ever have all its employees in the same place at the same time.

Srivastava is showing me Tomfoolery’s first product, which goes live today: a web- and iOS-based social network app called Anchor. At the core of Anchor, which looks and acts like a more beautiful cross between Facebook and an enterprise network like Yammer, are self-created groups. Tomfoolery’s team has dedicated groups for new music, what they’re cooking (that one’s called “Tomfoodery”), and cat pictures. But they also have an invite-only group just for founders and a public one for discussing bugs. Team members can share links, photos and video, check-ins, and other content, as well as engage in group and one-on-one chats. Much of the Anchor experience is about taking existing social behaviors–checking in on Foursquare, sending status updates to Facebook, texting with friends–and contextualizing them for the workplace.

Srivastava is quick to point out that Anchor, and Tomfoolery at large, is not trying to replace existing task management or collaboration tools like Asana or Basecamp. Instead, she likens the ideal Anchor experience to that of company offsites, which she says are powerful for team bonding, but happen only once in awhile.

“We want that kind of culture creation and real-life connection to be happening in real time,” she says.

The hope is that Anchor will serve as a platform for all kinds of apps that solve different pain points in the enterprise world (think apps for calendars, or meetings). Tomfoolery, which has raised $1.7 million from investors including Andreessen Horowitz and TechStars’ cofounder David Tisch, has several app concepts in the pipeline. But Srivastava’s cofounder, Sol Lipman, says he would also like Anchor to serve as a playground for third-party developers to build upon.

If anyone can make enterprise sound as sexy to consumers as Box‘s Aaron Levie does to businesses, Srivastava and Lipman want to be those people. Both have deep backgrounds in consumer products: Srivastava has managed teams at Adobe for Photoshop and Yahoo for Flickr, Mail, and Messenger; Lipman, a serial entrepreneur, has also worked on product for AOL. The duo’s consumer backgrounds have led them away from a direct-to-CIO model for selling their software–instead, Tomfoolery will sell its products through app stores, the same place you’d go to find and download a typical consumer app. That business decision reflects a trend the two anticipate will permeate the modern workplace very soon.


“The future of work is about friendships, bringing your own devices, picking your own software,” Lipman says. “It’s about collaborating outside of the lines,” Srivastava adds.

The iOS app will be free for life to anyone who downloads it before September 25th (a marketing ploy–that’s Lipman’s birthday). And though it’s not coming out today, the Tomfoolery team has also created a version of Anchor for Google Glass, the smart-computer headset which, along with an Android app, is coming within a month.

About the author

Christina is an associate editor at Fast Company, where she writes about technology, social media, and business.