In the mid-1980s conditions were such that Sarasota could absorb the development of a single high-rise office building. Encouraged by the tax code at the time and abundantly available financing, five developers built it. This same scene played out nationwide, increasing supply to unsustainable levels and ushered in the collapse of commercial real estate and of lenders not seen since the Great Depression of the 1930s and a crash that devastated commercial real estate. Two decades later, beginning in 2003 through 2007, another real estate boom took hold in the U.S. and especially in Southwest Florida. Unlike the upcycle of the 1980s, however, last decade’s growth was focused almost exclusively on residential product, largely fueled again by undisciplined lending practices. The pain of the subsequent collapse is, or should be, all too fresh in our minds. The present cycle in Sarasota and throughout the region has already eclipsed previous booms, especially for downtown development. But real estate remains a cyclical business. Though equity and all-cash deals are prevalent today, investors must be prepared for Southwest Florida to cycle into a slowdown, crash or worse. Time will tell if, or more likely when, that will occur.