The Vintory Podcast Episode 55: Top 10 Mistakes — 26-Year-Old CEO Jack Zoppa’s Journey in the STR Industry
In Episode 55 of the Vintory Podcast, Brooke Pfautz sits down with Jack Zoppa, a 26-year-old entrepreneur who is already leading two companies in the vacation rental space. Jack is the CEO of Haven Vacation Rentals in the Smoky Mountains and the Co-Founder & CEO of Tendwell Cleaning Co.
At just 26, Jack has built and scaled both a property management company and a cleaning operation in one of the most competitive short-term rental markets in the country. But the journey hasn’t been smooth.
In this episode, Jack shares his top 10 mistakes in the industry — the lessons that shaped him as a young CEO navigating rapid growth, operational challenges, team building, and the realities of scaling service-based businesses.
Enjoy!
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Vintory is the first and only platform designed exclusively to help vacation rental managers recruit new homeowners and add more properties to their management program.