Updated on May 23, 2023
Sarah Bradford and Tim Cafferty recently marked a milestone with the recording of their 150th episode of Sarah and T: The Professional Vacation Rental Manager’s Podcast.
Every other Monday for nearly six years, they have released a new 30-minute episode packed with takeaways to improve your vacation rental management business.
A distinguishing trait of the podcast is that it’s largely content they create from their combined experiences and expertise rather than a lineup of interviews – though they do sometimes host guests.
“Most of the time, it’s Tim and my experience and knowledge that we’re sharing; we’re creating content, so it’s honestly boundless,” Sarah said.
But where did the podcast get its start? And what’s the secret to Sarah and T’s longevity in an ecosystem where, according to a study by Medium, the average lifespan of a podcast is less than six months?
Insider meeting of vacation rental managers
Sarah and Tim are both seasoned vacation rental managers with a combined experience of 56 years (20 for Sarah and 36 for Tim).
They come from different markets 2,000 miles apart.
Until last year, Sarah and her husband owned two vacation rental management companies in the ski towns of Steamboat Springs and Winter Park in the mountains of Colorado, while Tim still owns and operates two vacation rental management companies in Kitty Hawk, North Carolina, and Sandbridge, Virginia, both southern beach towns on the Atlantic.
Steamboat Springs, CO and Outerbanks, NC
Photos by Sean Kelley and Raymond Kotewicz on Unsplash
They met when they both participated in a confidential vacation rental insider group organized by Claire Reiswerg, owner of Sand ‘N Sea Properties in Galveston, Texas and facilitated by Sue Jones. The group met every six months in different cities to talk about industry trends and share their wins and struggles with each other.
Vacation rental management banter
Their memories of the first time they met reverberate with the humor and banter that make Sarah and T as entertaining as it is educational.
“So, we went to Chicago and we met in the lobby of a hotel,” Tim recounted. “I think I gravitated to her more than she gravitated to me. She was like, who in the hell is this guy?”
“No, by the way, he got there a day late,” Sarah interjected, “and he walked in like a hotshot.”
First impressions aside, the idea of the podcast came six months later when the group convened a second time in Louisville, Kentucky, a towering city on the banks of the Ohio River.
“We were sitting around this room, and we had to say what’s been happening the last six months in our life, what’s been bringing us joy, something new we’ve learned,” Sarah recalled. “And I said, ‘You know, I’ve been listening to a lot of podcasts. It would be so fun someday to have my own podcast.’”
“And then we laughed and moved on,” she said. “Then it went around the room – I can see this visually. When it got to Tim, he gave all his updates on what he’s been doing and hotshot stuff. And then he goes, ‘Sarah, I just came up with a name. How about Sea to Ski with Sarah and T?’ And everyone just howled like, oh, that’s so funny; he came up with a name.”
From a half-joke to a vacation rental podcast success story
It turned out that Tim was serious. With a background in broadcast journalism, he had presentation and audio editing skills that would be useful.
Three weeks after the roundtable in Louisville, he called Sarah and said, “We should do this.”
Sarah thought “really? Like how do you even do a podcast?”
They started recording episodes of Sea to Ski with Sarah and T for fun. (They later changed the name to just Sarah and T.)
“Honestly, I didn’t think anyone would really listen,” Sarah said. “So it’s crazy to see now when we upload an episode, and it shows all the downloads happening. And then when you go to a conference and people come up to you and they exclaim, I learned so much from you. You changed my business.”
What are pullover moments?
The goal of the podcast is to leave listeners with takeaways that they can immediately apply to their businesses. Sarah and Tim call these takeaways “pullover moments,” which means essentially valuable nuggets of information that a listener who is driving might want to pull over to write down notes.
“Safety first,” Tim quipped, “We don’t want anybody writing while they’re driving. Or if they’re jogging, we don’t want them to trip over a rock because they had a great idea and they need to write it down.”
That aligns with a statistic that shows nearly half of podcast listeners tune in while they’re driving or exercising, according to a survey by NuVoodoo.
They also coined NSHOTPBDH, an acronym that stands for Not So Hot Off The Press But Definitely Happening. NSHOTPBDH is a short news segment at the end of most episodes when Sarah and Tim comment on what’s happening in the vacation rental industry.
Keeping property management interesting
A focus on practicality and professionalism doesn’t mean the duo and their listeners can’t have a little fun. The co-hosts have recorded episodes under adventurous conditions, including while drinking rum and Coke at one of their vacation rental insider group meetings, live in a VRMA conference session, even while in the back of an Uber.
In the Uber episode, 10 Keys to Housekeeping, “The Uber driver started to give his opinion, so we just let him talk,” Sarah said.
Every year, they record an episode live at the VRMA National Conference where everyone in the audience takes the microphone and shares one thing they’re going to take away from the conference. The episode is a way for those who couldn’t participate in the conference to still learn some of the takeaways and apply it to their businesses.
From podcast to professional vacation rental management education
But Sarah and T’s lasting legacy may be as a resource library of evergreen content for property managers. Sarah and Tim both have used their episodes to train employees at their own businesses, and listeners have done the same.
On their 100th episode, Brian Harris, founder of Harris Vacation Rentals in Gulf Shores, Alabama, called in to say the podcast has helped him to grow his business and that he uses the podcast’s library of content to train new employees, including the new COO/CFO. “We are actually using your podcast as a training guide so he can learn the ropes and learn from the best,” Brian said.
And the podcast’s popularity continues to grow.
Since its inception, the podcast has been downloaded over 170,000 times, ranks in the top 10% of Apple podcasts, and has a five-star rating from 77 reviewers.
How vacation rental managers can be better citizens
Tim and Sarah recently participated in the “podcaster takeover” at the Rent Responsibly Summit: People, Places, and Planet on April 18, 2023, where they recorded a podcast episode called How Many Guests Are Too Many?
The episode covered what vacation rental managers can do to be better citizens. Sarah and Tim emphasized the importance of volunteerism and community involvement, especially joining the conversation about how much workforce housing is needed in your destination.
Tim volunteers as chairman of the Dare County Tourism Board and is housing committee chairman of the Dare Education Foundation in his local community. The Dare Education Foundation is spearheading the construction of 36 housing units for teachers employed in the local public school system.
Core values and paying it forward
Perhaps one aspect of Sarah and T’s staying power is that they have stayed true to their core values from the start of the podcast.
“A professional vacation rental manager’s podcast has been really an important differentiator for me,” Tim said. “It’s like I tell my staff, being professional is not something you can say about yourself. It’s something that somebody has to describe you as.”
“And so what does it mean to be professional? There’s a seriousness to it. This is not a hobby. We give you tips to run your business, professionally. And I think that has been a core value from day one. And I think every episode has pretty much reflected that.”
Part of their success has also been their passion for vacation rentals, entrepreneurship, and helping others.
“Tim and I both love teaching,” said Sarah, who is a former high school teacher. “Seeing somebody light up learning something, being a better person, being a better business. It brings us joy.”
“I have just an insatiable curiosity,” Tim added. “And vacation rentals satisfy that because every day is a new challenge. And I think at heart, a lot of us in the vacation rental business are problem solvers. And I want to help. And I get to do that everyday. I never know what today’s gonna hold, but I know it’s going to be fun.”
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