Roy's first real job was picking up rocks and debris on a property in California.
Today he's a Tech Architecture Manager in San Antonio, Texas, with 16 years in tech behind him. And in less than a year on NextWork, he has completed more than 200 projects - every single one of them is sitting in his portfolio for anyone to open.
By almost any traditional measure, Roy has already made it. So why is he still learning at this pace? Because the job he worked so hard to get keeps changing, and building is how he has learned every single thing in his career so far.
Three careers and about twenty jobs
Roy didn't take the straight road into tech. He worked his way up in construction until, in his words, his body made that plan stop working. Then he moved into hospitality, and he chose it on purpose: he couldn't talk to people, so he took a job that would force him to. That became physical security for hotels and condos, and then an operations manager role.
His way into tech was a support desk job, with no tech experience at all. This is how he describes what came after:
"I bridged the gap with what hospitality had taught me, and it was still a completely different game. Three careers and about twenty jobs later, I am a senior engineer and a manager. All of it self-taught, on the job, by building.
Would I change any of it? No."
"Another way of learning"
When AI came along, Roy did the same thing he'd done with every career before it.
"I thought AI was for people with PhDs, locked in a lab somewhere. It is not. It is another way of learning, and you get at it the same way you get at anything else, by building with it."
He calls himself a "lazy engineer", and he builds accordingly. Most of his projects are systems that do the manual work for him, so he has more time for his family, his health, real estate, his hobbies and the advisory business he runs on the side. One of them is a mock interview system with three AI personas - a hiring manager, a technical lead and HR. Another is an Excalidraw-to-Linear workflow powered by Obsidian, Codex and 25 agents.
He says building these has changed how he works, both in his day job and in his own businesses.
Teaching what he learns
Roy believes you lock in what you've learned by building real things and then teaching them to someone else. He sums it up as "prompt, build, connect", and it's why he now runs a weekly Build & Brew group, where a small group of learners meets to build projects together.
He is very clear that he isn't there as the expert:
"Am I an expert? No. I am 10+ months in and building every day. That is the whole point of this Build & Brew group: I am a little further down the same road you are on, and we cover the rest of it together."
Our founder Amber Winton first wrote about Roy in The market most VCs miss, and he's still one of the clearest examples we know of someone who never really finishes learning, because the work he's responsible for never really stops moving.
Roy, thank you for showing up for your Build & Brew group every single week, and for proving to so many people that you don't need a PhD to build with AI.