Pamplin alumnus on building companies and backing entrepreneurs

What started as a random roommate pairing in Lee Hall in 1995 (now Hoge Hall) turned into a lasting friendship, a successful startup, and a lifelong commitment to entrepreneurship.

Pat Matthews ’02 is an entrepreneur turned investor who now runs Active Capital, a venture firm he founded to support the next generation of software founders. After building and selling his own company, Matthews shifted from founder to funder, but he never lost his connection to Virginia Tech or his passion for early-stage entrepreneurship.

Today, he channels that experience into investing, mentoring, and serving on the board of the Apex Center for Entrepreneurs. It is his way of giving back and staying close to the energy and creativity that comes with Hokies chasing big ideas.

“I love being around students who are just getting started,” Matthews said. “It reminds me of where we were–young, scrappy, and trying to build something from nothing.”

Matthews came to Virginia Tech as a general studies major and a first-generation college student. Growing up, he was always the friend in his group who worked multiple jobs. This taught him grit and work ethic, traits he carried through college and into his career. While still enrolled, he and two fellow Hokies turned their friendship into a business venture. As the company got off the ground, Matthews dropped out just a semester and a half before graduation in 2000 to focus full time on building the startup.

“We dropped out to start a dot-com company and pursue our dreams of being entrepreneurs,” Matthews said. “Shortly after starting the first iteration of our business, the whole dot-com market crashed and put us in a difficult spot.”

As Hokies do when facing adversity, Matthews continued to reposition and reimagine the company until success came in the form of an enterprise software business. One of the smartest bets he made during that time was returning to Virginia Tech to finish his degree.

“It’s cool to talk about being a college dropout, but when you’re a college dropout with $100,000 in credit card debt and your business is failing, it’s not as cool,” Matthews said. “My business partner and I took turns going back to school to hedge our bets on ourselves, and I graduated in May of 2002. While back in school, the world was rapidly changing around us, and that shift allowed us to find success.”

That success became Webmail.us, one of the first large-scale business email hosting services in the world. Suddenly, Matthews and his co-founders were managing mission-critical email infrastructure for companies across the globe. They moved the business to Northern Virginia to facilitate growth, but Matthews quickly realized the best talent he could hire was still in Blacksburg. He brought the company back to where it all started and began recruiting ambitious Hokies to work part time and year-round while still in school. Many of those students would later become full-time employees.

By 2007, Webmail.us had grown to $10 million in annual revenue and was acquired by Rackspace. Matthews relocated to Rackspace’s headquarters in Texas, where he lives today. Over the next six years, he served on the executive leadership team, helping the company scale and solidify its customer-first culture.

In 2014, after leaving Rackspace, Matthews embarked on a new chapter supporting founders who were building companies from the ground up, just like he had in 1999.

“I started angel investing in startups with the money I had personally made through selling my company,” Matthews said. “After a few years of investing, I felt like something was missing. I wanted to build something again, so I founded Active Capital in 2017 to invest in the future of enterprise software and cloud infrastructure.  Today we’re a venture capital firm with more than $100M under management across three funds and a portfolio of over 75 startups.”

Matthews shared that he focuses on investing at the earliest stages, often backing founders based on their vision, grit, and business instincts.

Nearly a decade later, Matthews continues to apply that philosophy through Active Capital, as a dedicated Apex Center board member, and through his dedicated annual philanthropic support. He regularly connects with Virginia Tech students and alumni, introducing them to entrepreneurship and the power of the Hokie network.

For Hokies with big ideas, Matthews is more than an inspiring story. He is living proof that the right mix of vision, perseverance, and community can turn a dorm room dream into lasting success.