A former banking consultant turned a family medical situation into a 95-property short-term rental empire by treating vacation homes as both lifestyle assets and business platforms—proving that the real wealth isn’t in owning real estate, it’s in building something on top of it.
Most real estate investors treat properties like passive piggy banks. But what if you could build an entire business empire on top of your portfolio—one that private equity firms are already eyeing? This conversation reveals how someone turned a family medical crisis into a $95-property management company, all while teaching their kids to be entrepreneurs. The tax benefits alone might change how you think about your next acquisition.
After 20 years in corporate banking consulting, this entrepreneur left the safety of the C-suite to launch coffee shops—only to have COVID destroy that dream completely. A daughter’s severe food allergies requiring trips to California sparked an unexpected pivot: buying short-term rentals as lifestyle assets that generate income when not in use. By leveraging banking knowledge of deal structuring and capital raising, he scaled to 11 owned properties and 95 managed units in just six years. The secret isn’t just real estate—it’s understanding how to stack multiple financial levers (equity, cash flow, and cost segregation) to create custom deals with investors. Now he’s building something his three kids can inherit while exploring exit strategies with private equity.