
“I’m going to take the plunge!” Grant told me as we headed into the after party. It was Christmas 2011. We had just left the official Net Friends holiday bash, and he was in very high spirits. I remember seeing in the cold night air a manic gleam in his eyes. It was a mix of being terrified and thrilled at the prospect of going out on his own. “It’s going to actually happen,” he said, “just a matter of time now.” I knew Grant was eager to break out. He had so many great ideas, and his passion was bridled working within the massive enterprise environments he’d spent the last decade doing contract security work for.
I first met Grant Leonard back in 2002. We hired him at Net Friends as a contractor to help with all sorts of IT security projects and initiatives. Within a year, he helped me build and execute our first recurring service: monthly HIPAA compliance reports for healthcare customers. Since then, he’d helped us iterate and expand the service from analyzing five core areas of security to more than a dozen. There was no doubt in my mind that Grant had the talent, the grit, and the ability to sustain through good times and bad. I’d seen him in action, and I knew he was going to be wildly successful in his new venture.
The next summer, Grant made it official. His sole focus now had a name: Castra Consulting. Although he was busy launching a startup, Grant maintained strong ties with Net Friends. He helped build out our security log collection and monitoring services, and he continued helping us with those HIPAA compliance reports. We had several discussions in 2012, trying to figure out some way for Castra and Net Friends to collaborate officially. Understandably, Grant and his business partner, Tony, were primarily focused on developing their unique professional service offerings. But Grant kept telling me, “We’re going to figure out some way for Castra and Net Friends to work together, brother!”
After lots of phone meetings and email exchanges (Grant traveled a ton in Castra’s first year!), the die was cast on May 23, 2013. We met for coffee in the morning, at Beyú Caffè in downtown Durham, and then hashed out the broad strokes of what would become the Castra/Net Friends joint venture: Castra Managed Services.
Up to this point, Castra had been solely offering professional services, which essentially meant project and consulting work that was tracked and billed hourly. Together, our two companies could assemble a Security Operations Center (SOC) and build a series of managed security service offerings. We knew we could build this joint venture together based on our shared values, shared work ethic, mutual respect, and deep well of trust. Although we went right to work, it took another 2 years before our SOC was actively up and running, supporting multiple customers, and operating under a well-defined agreement.

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