EPISODE · Feb 27, 2026 · 59 MIN
Episode 55: Top 10 Mistakes — 26-Year-Old CEO Jack Zoppa’s Journey in the STR Industry
from The Vintory Podcast · host Brooke Pfautz
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!⭐️ Links & Show NotesVacation Rental SecretsBrooke PfautzJack ZoppaHaven Vacation Rentals Tendwell Cleaning Co.🔗 Connect With VintoryWebsiteLinkedIn🚀 About VintoryVintory is the first and only platform designed exclusively to help vacation rental managers recruit new homeowners and add more properties to their management program.
What this episode covers
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!⭐️ Links & Show NotesVacation Rental SecretsBrooke PfautzJack ZoppaHaven Vacation Rentals Tendwell Cleaning Co.🔗 Connect With VintoryWebsiteLinkedIn🚀 About VintoryVintory is the first and only platform designed exclusively to help vacation rental managers recruit new homeowners and add more properties to their management program.
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Episode 55: Top 10 Mistakes — 26-Year-Old CEO Jack Zoppa’s Journey in the STR Industry
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