From Law School to Top 20 Most Influential People in the Vacation Rental Industry Globally

Michael’s journey began in a Milwaukee suburb near the beautiful shores of Lake Michigan, where he cherished his childhood. He pursued higher education at the University of Wisconsin in Madison, where he majored in history and political science.

At first, Michael wasn’t entirely sure about his career path. He had contemplated law school and government work but found himself increasingly intrigued by his family’s real estate background. After a brief and unsatisfying stint at Macy’s in New York, he wholeheartedly embraced real estate, diving into areas like residential sales, vacation rentals, and hospitality.


Michael’s passion for vacation rentals and travel has remained unwavering. He also has a deep love for food and dreams of a life akin to Anthony Bourdain’s globetrotting culinary adventures. But at his core, he’s all about real estate and the vacation rental industry.


During the interview, Michael emphasized the significance of hiring based on character, not just education. He stressed that while education is valuable, understanding social dynamics and having industry-specific social skills are equally important. Education is just one piece of the puzzle; the ability to perform effectively in a field matters greatly. In the hospitality industry, where Michael operates, character takes center stage.


When asked about his family’s influence on his career choices, Michael acknowledged their role but also highlighted his personal pull toward real estate. His success in residential real estate is attributed to his charisma and strong interpersonal skills. He talked about his knack for building genuine relationships quickly, a skill that led him to an industry that thrives on close collaboration. This path eventually led him to real estate and, more specifically, the short-term vacation rental industry, where he’s been active for an impressive 15 to 16 years.


Michael passionately stressed the importance of character-driven hiring, particularly in hospitality. He firmly believes that understanding social dynamics and having industry-specific skills are crucial for success. Although his family nudged him toward real estate after some uncertainty, it was his charisma and relationship-building skills that allowed him to excel in residential real estate. These same qualities guided him toward the vacation rental sector, where he’s been a prominent figure for over a decade.


Flo noted the value of being likable in the real estate industry, a sentiment that Michael wholeheartedly agreed with. He emphasized how his charisma has significantly benefited his career. Reflecting on his journey, Michael mentioned his pivotal role in assisting his father’s company and recognizing real estate’s potential. Although he initially found it uninspiring, he came to appreciate its profitability through his father’s insights, eventually leading him to embrace residential real estate.


Michael’s journey in real estate has been extensive. A humorous comment from Flo triggered his realization about the importance of aligning values when buying and selling properties. Despite initial doubts, he excelled in the field, eventually becoming a real estate coach alongside his sales role. This passion eventually led him to the world of vacation rentals.


His journey into vacation rentals began with consulting for i-trip, a prominent franchise in the industry. Initially tasked with developing their training program, I Tripp University, Michael helped new franchisees scale their businesses. What began as consulting evolved into a dedicated six-year commitment, immersing him in the vacation rental sector.


When it comes to choosing companies and roles, Michael places a strong emphasis on shared ethics and values. He acknowledges the industry’s fragmentation and champions collaboration as the key to unifying it. In his view, uniting the industry requires collective effort and strong leadership.


Michael also underscores the importance of aligning personal values with a company’s culture. This alignment serves as a guiding compass when making decisions and embracing new opportunities. His appetite for challenges and change significantly influences his career choices, with a strong emphasis on the value of aligning personal values with a company’s ethos.


Michael reflects on the intricate process of aligning companies and employees, likening it to the art of building personal relationships. Although he doesn’t claim to have a definitive solution, he underscores the significance of matching leadership values with individual enthusiasm for the product or service.


Regarding his move to One Fine Stay, Michael recounted his previous experience with a startup that didn’t go as planned. He explained how he joined One Fine Stay as the Chief Operating Officer for their Americas expansion, facilitated by a US-based search company. Drawing on his expertise in business growth, he contributed significantly to One Fine Stay’s property management and online travel agency (OTA) efforts on a global scale.


Looking ahead, Michael envisions continued career growth within the expansive hospitality industry. While specific plans may remain uncertain, his focus is on giving back to and supporting the industry’s development. He contemplates providing consultation, sharing insights, and offering support to various companies, property management firms, and vendors. He places a profound emphasis on the value of contributing to an industry that has played a pivotal role in shaping his journey.


Shifting to Vacation Rental University, Michael discusses its creation five years ago. Recognizing a need for comprehensive education in the vacation rental sector, they embarked on a journey to develop an extensive curriculum over seven months. This platform offers not only free foundational lessons but also affordable subscription options for deeper content. From assisting small management firms to integrating with larger enterprises’ learning systems, the university empowers professionals with essential tools for success in the vacation rental business.


The interview concludes with Michael’s unwavering commitment to giving back, his enthusiasm for education, and a lighthearted mention of potentially teaching vacation rental management at the University of Wisconsin.

Watch the full interview here.