Guy Filippelli

Guy Filippelli

Managing Partner
Squadra Ventures

When Guy Filipelli and his team make investments, they do it when they can make a contribution beyond capital. He and his team bring not only the dollars behind the investment, they work to “dominate, create value and grind.”

This special recipe came after Filipelli’s own experience as an entrepreneur. He built what he wished had existed when he was raising capital – first as a founder- CEO of bootstrapped information technology services firm Berico Technologies, and second as a founder- CEO of a venture-backed cybersecurity company, RedOwl Analytics. RedOwl was acquired for $54 million by Raytheon in 2017.

Filipelli also combines his nearly decade of work as an Army intelligence officer with his strong belief in integrity when finding and investing in the next venture. He describes himself as “being obsessed with helping entrepreneurs build and run great companies – and making the connections that truly move the needle.”

He started Squadra Ventures in 2019 with the goal of building a world-class venture fund. He and his team have a deep appreciation for leadership and team-building, and the “soft side” of hard tech.

To him, exceptional teams are the key to outsized success. He and team view their investments as an 18-month accelerator program, working alongside a company to help it succeed.

Squadra’s first investment came in 2019 when the firm helped Pinkaloo, a charitable giving startup. The company’s most recent investment was for Overwatch Imaging, a Portland-based firm that makes imaging systems for piloted and autonomous aircraft.

While Filipelli and his team are interested in growing their venture firm into a top-tier fund throughout the mid-Atlantic, they are dedicated to seeing the Baltimore community develop.

In addition to being passionate about building the next generation of tech companies, Filipelli is an ardent lover of food, wine, and all things Italian. He is also a zealous bread baker.