What happens when you run the numbers on the Airbnb you're staying in and realize it beats every turnkey rental you toured that day? For Tim Hubbard, it meant walking away from the long term rental deal he flew to Tennessee to find, buying a historic eight-unit apartment building instead, and converting it to short term rentals. That single property went on to earn roughly eight times what it produced as a long term rental, and it set him free.

In this episode, host David Richter sits down with Tim to trace the whole journey: discovering Rich Dad Poor Dad nearly 20 years ago, fighting through loan denials as a 1099 contractor to buy a foreclosure fourplex in downtown Sacramento in 2010, house hacking one unit while the other three covered the bills, and 1031 exchanging his way into bigger buildings and better markets.

Today Tim runs roughly 65 units, 45 of them short term rentals, from South America, where he's lived for nearly a decade, first in Colombia and now in Brazil. He's also weeks away from opening the first phase of a boutique resort in Colombia and leads Corzly, a core operating center that handles revenue management, 24/7 guest communication, and marketing for short term rental owners and property managers in more than 40 cities.

Tim doesn't sugarcoat the 2026 short term rental market: it's more competitive, guest expectations are higher, and owners still pricing like it's two years ago aren't getting booked. This conversation is a masterclass in reading supply and demand, finding the luxury edge, and building operations that let the profit actually reach you.