A Winding Road To Success

Crazy. That’s how David Pessis describes his decision to enroll in Northwestern’s Master of Science in Information Technology program and to launch a new business venture simultaneously.

“People say entrepreneurs are the dumbest smart people in the world because they don’t know what they’re up against,” Pessis jokes. “I guess that’s me.”

In late 2007, Pessis launched Fippex, a cloud-based client enablement and communications platform built initially for private equity firms and hedge funds. At the height of the financial crisis and amid the fallout from scandals triggered by the likes of Bernie Madoff, Fippex promised to inject transparency into the marketplace by allowing investors to see the real-time status of their investments.

For Pessis, Fippex became a religion, consuming his hours and his heart. “I lived and breathed it every day,” he says. With his graduate program’s business courses to inform his entrepreneurial efforts, Pessis says, “I felt pretty good about the tech side, but learning about marketplace positioning and customers, cash flow statements, and balance sheets made me much more effective.”

Delivering custom, big-enterprise deployments fueled by the system architecture skills of Aly Boghani (MSIT ’07), Pessis’s fellow Northwestern Engineering alum, Fippex gained traction quickly, earning the business of leading private equity firms and international banking giants.

“I FELT PRETTY GOOD ABOUT THE TECH SIDE, BUT LEARNING ABOUT MARKETPLACE POSITIONING AND CUSTOMERS, CASH FLOW STATEMENTS, AND BALANCE SHEETS MADE ME MUCH MORE EFFECTIVE.”

Energizing as that was, Pessis and his Fippex colleagues recognized an even greater opportunity: spinning that kind of transparency from the realm of finance to sales.

In June 2013, Fippex reincarnated and rebranded itself as PointDrive, a sales-oriented application designed to help sales teams package, personalize, and share digital content—files, links, videos, and more—with prospective customers. The PointDrive system also included analytics to identify the most relevant content for streamlining a successful sales cycle.

“This opened up a whole new world for us,” Pessis says. PointDrive quickly earned acceptance by top real estate firms and sales organizations, including LinkedIn, which saw so much potential that it acquired the company in July 2016. As the social networking powerhouse performed its due diligence en route to closing the deal, Pessis relished—albeit sometimes anxiously—the trip “down memory lane,” reliving the milestones and missteps of his startup’s winding, nine-year journey.

“You make thousands of mistakes as an entrepreneur since you are doing so many new things,” says Pessis, who joined Amazon Web Services in Seattle in 2013 but remained a member of the PointDrive board. “I’m so grateful we had a successful exit; I know that’s not the case for most entrepreneurs.”

Pessis acknowledges that a little crazy in the entrepreneurial life goes a long way, but still says, “Honestly, I can’t wait to do it again.”