Some people chase the biggest portfolio they can find. Michael Friedman did the opposite, and it might be the smartest thing he ever did. Matt and Austin sit down with Michael Friedman, CEO of Simple Life Hospitality and co-founder of Vacation Rental University, for one of the most experience-packed conversations the show has ever had.

With over 35 years in hospitality, vacation rentals, and real estate, Michael has held executive roles at two of the largest franchise operations in the industry, served as COO of the Americas for the ultra-luxury Onefinestay brand where he oversaw more than 3,500 properties, and is now intentionally leading a tight, focused operation of 150 homes across Door County, the Northwoods, and Green Bay, Wisconsin. Door County, often called the Cape Cod of the Midwest, is a stunning peninsula wedged between Lake Mic ...