Real Estate Strategy that Works | Jason Matthews & Leo Climaco

The fastest way to lose money in real estate is to believe a market headline without ever touching the street. From the Ritz Carlton in Dallas at the Board of Advisors Q1 Summit, we talk with Jason Matthews, a 30-year real estate investor and developer based in Tampa, Florida, about how he actually picks winning neighborhoods and why “local” beats “logical” when you’re only looking at spreadsheets.Jason breaks down how his best deals start with a simple habit: park, get out, and walk. He explains what you can learn from the cars on the road, the way homes are maintained, and the feel of a block that’s starting to turn. We also dig into the myth-making that happens when people rely on broad data alone, and why following public money like bridges, airports, and infrastructure projects can reveal where demand is getting built next. If you care about neighborhood analysis, real estate market trends, and risk management, this conversation is packed with clear signals you can apply.From there, we get tactical about operations and scale. Jason shares his one-hour drive rule for staying in control, how he built a high-performance ecosystem without employees by partnering with motivated business owners, and how his team grew a portfolio that includes luxury beach homes run as short-term rentals designed for group bookings. We also go deeper on mentorship and family business succession, including the decisions he and his wife made to put their kids first so the next generation wants to carry the business forward.If this hit home, subscribe, share it with a builder or investor you respect, and leave a review so more founders can find the show.