Pat Matthews

Entrepreneur, Operator, Investor

Hi, I'm Pat. I'm an entrepreneur turned investor who's spent my entire career starting, scaling, and investing in startups.

In 1999, I dropped out of Virginia Tech to start a dot-com with some of my best friends and college roommates. Then the dot-com bubble burst. After a few years of doom and gloom, we started to see the IT landscape shift. Businesses were becoming comfortable with software delivered over the internet. Software-as-a-Service was becoming real, and we went all in.

From 2002 to 2007, we built Webmail.us into a $10 million SaaS company on just $500,000 of outside capital. We bootstrapped the company to $1 million in annual recurring revenue before raising money from investors. We built an amazing team and culture, hosted email for tens of thousands of businesses around the world, and ranked #217 on Inc. Magazine's list of the fastest-growing private companies in America.

And we did it all from the tiny town of Blacksburg, Virginia…the home of Virginia Tech.

In 2007, we were acquired by Rackspace, our hosting partner at the time. Based in San Antonio, Texas, Rackspace was one of the fastest-growing tech companies of that era, generating $300 million in annual revenue when we joined. A year later, in August 2008, Rackspace went public. Being a public company is crazy. Going public in the middle of a global financial crisis is even crazier!

I spent six years at Rackspace…longer than any entrepreneur whose company we acquired…and loved every minute of it. I was fascinated by our culture of Fanatical Support, our ability to differentiate in a crowded industry, and what product-market fit looked like at massive scale.

I eventually found myself leading some of the fastest-growing parts of the company, including our cloud computing businesses. It was an amazing time for the industry, for Rackspace, and for me. During my six years there, Rackspace grew from $300 million to $1.5 billion in annual revenue…and we were profitable the entire time.

After leaving Rackspace, I spent a couple of years consulting, angel investing, and figuring out what I wanted to do next. I loved certain aspects of angel investing, but it wasn't fulfilling enough for me to do full time. I wanted to work more closely with founders. I wanted to be there earlier, when the company was still small and messy and a few people could make a huge difference.

So I decided to combine the investor in me with the entrepreneur in me.

In 2018, Active Capital was born.

Today, Active is a pre-seed venture firm backing technical founders as they rebuild software and infrastructure for an AI-native world. We're often among the first investors involved, and I get to spend my days doing what I love…working alongside ambitious founders as they turn early ideas into valuable, enduring companies.

I still live in San Antonio with my long-time girlfriend and teenage son, although these days I'm spending more and more time in San Francisco. I love traveling the world, spending time with awesome founders, meeting interesting people, and having fun along the way.


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