Episode 30: Connecting with Dakoyta Greenman

Meet Dakota Greenman, Founder and CEO of Westwood AI, a technology company revolutionizing how commercial real estate owners, property managers, and portfolio holders assess, monitor, and protect their assets. A U.S. Air Force veteran with a background in geospatial intelligence, Dakota bridged his military experience with entrepreneurship to build Westwood AI from the ground up — bootstrapped, deliberate, and built to last. At its core, Westwood AI's flagship product, Roof Ranger, uses drone technology, machine learning, and multi-spectral analytics to give commercial property owners unparalleled visibility into the condition and value of their assets — from due diligence through long-term portfolio management. Dakota recently accepted back into a PhD program in data science, and Westwood AI is now ready for its full commercial launch — with Power Connections CRE as the launchpad. Explore Dakota's non-linear journey from barely graduating high school to guiding hunters in the Brooks Range, to opening businesses out of a Muskegon recruiter's office, to building a machine-learning platform that's now turning heads across Michigan and beyond. His story is one of calculated risk, relentless belief, and the discipline to slow-roll a product until it's truly ready — then show up at exactly the right room. IN THIS EPISODE, WE TALK ABOUT: -The absurdity of belief required to build something real, "It's okay to have absolutely no rational idea justifying what you're doing — but there's such a belief in there that if I don't, I'm gonna hate this decision for the rest of my life." -The risk of not acting, "There's a risk of doing — and there's also a risk of not doing." -Why preparation earns the opportunity, "I get one shot to impress. If you go out there and it flops, that's a small community. It's almost impossible to get that second chance."