Michael Friedman

Chief Executive Officer

With over 35 years of experience in luxury hospitality, vacation rentals, online travel, and real estate, Michael brings a wealth of knowledge and leadership to his role as CEO of The Simple Life Hospitality. He is also a distinguished co-founder and board member of Vacation Rental University (VRU), where he shares his expertise in coaching, consultative sales, executive leadership, talent development, and operational excellence.

Previously serving as COO for the Americas at Onefinestay, Michael led a luxury portfolio of more than 2,500 properties, driving profitability, operational efficiency, and exceptional guest satisfaction. Widely recognized in the industry, he was named one of the “Top 20 Most Influential Professionals in the Vacation Rental Industry Globally” and is a sought-after speaker and thought leader on the global stage.

Michael describes joining The Simple Life Hospitality as one of the most rewarding decisions of his career. His dedication to empowering others and fostering the company’s continued growth is evident in every facet of his leadership.

In his free time, Michael enjoys cheering on the Badgers and Packers, spending time outdoors fishing, and making memories with his sons, Alex and Sam. After two decades in Charleston, SC, he returned to the Madison, WI area in 2020.