From fetching golf carts to flipping houses

While recovering from a failed business venture and working as a caddie at a golf course, Denny Anderson decided to check out a tax deed auction, where he met a friendly flipper named Josh Williams. “He wanted to teach me, so I started working for him,” Anderson recalls. “He became one of my best friends, and he’s still a mentor to this day.” Here’s how that inspired Anderson to launch his own real estate business, Built to Buy, in Jacksonville, FL.

Average home price: $285,103 (down 0.8% YoY, per Zillow)
Homes that sell over list price: 18.3%
Homes that sell under list price: 59.4%
Average rent: $1,601/month

How he got started: After learning the ropes from a professional flipper, Anderson set off to buy his own first flip: a three-bedroom bungalow for $45,000, “off-market, from a tired landlord,” he says. He sank about $50k into renovations, then sold it for $155k.

His market’s pros: “Jacksonville is the largest city by land area in the continental US,” Anderson explains, which means a steady stream of builders, military relocations, and out-of-state movers. “Demand here doesn’t dry up,” he says. Plus, “infill lots are scarce, so the ones you find hold their value.”

The cons: “Florida insurance is the headwind nobody prices in until it wrecks their numbers,” Anderson says. Beachfront properties are especially risky, he notes, since entry prices are steep enough that “one bad buy erases two good ones.”

His advice: Run the real carrying costs (insurance, taxes, and vacancy), not the optimistic ones. That gap is where rookies get buried, Anderson warns. To lower insurance costs, certain renovations can help—especially a new roof, since it’s typically “the first thing insurers look at.” Even a roof’s shape matters, with flat roofs costing more to insure than slanted ones. Chalk that up as an only-in-Florida thing worth knowing before you buy.

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