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Stan Horst is one of the world’s few vacation rental veterans. He’s been hosting guests before the days of AirBnB, HomeAway, and even before the internet itself. With his unique perspective, Stan shares how his business modeled has evolved in the digital age, and how he still uses old-school marketing tactics to drive extraordinary results. We hope this episode will stir up some latent creativity, and show you...
Lot’s of people dream of unplugging from “the grind” and escaping to some far off exotic island paradise. Karla Gustafson, owner of Tropical Blessings, did just that. Frustrated with life as an English teacher in Dallas, Karla escaped to the Caribbean island of St. John where she became a “Moko Jumbie”, and then eventually found herself owning a vacation rental property with zero experience. In this episode...
Darik Eaton is the founder of Seattle Oasis Vacation Rentals. After the 2008 financial crash Darik closed down his business in commercial finance, and transformed his vacation rental from a simple side business, to a full-time vacation rental property management company with over 45 properties. Darik shares his experiences growing his vacation rental business, exporting his business model to Hawaii and the most...
Teena Kulakowski is a former chemist who now runs the successful Four Seasons Lodge in New Hampshire. Her experiments have taken her from newspaper advertising to chainsaw artists to building her own website. Along the way we’ll find out that the “secret ingredient” to her vacation rental’s success is a high dose of good ol’ fashioned personality. You’ll leave here learning the value of knowing your audience, why...
Rick Oster’s career has had many twists and turns. He spent most of his professional life climbing the corporate ladder as an overworked executive in the television & cable industry, and then took a detour to building his own aquatic installation company. Eventually, a curious insight led him to build his first vacation rental, a business he had zero experience in. Now, as the owner of Oster Golf Houses, Rick...
Jan Stevens’s journey in the vacation rental industry began when she inherited an old family fishing shack that they bought for $1,200 in the 50’s. Realizing she could leverage her talents as a professional interior designer, she turned the home into a vacation rental. As peers began to take notice of her business, they began asking her if she can manage their properties too. Jan shares her experiences growing...
Ralph and his wife Karen, like many people, fell in love with Paris. However, instead of doing what most people would of done, they began buying property in Paris & Nice. Since then, they have been successfully operating a vacation rental business remotely. In this episode we learn how Ralph and Karen have created a remotely operated business process, and how they’ve overcome the tragedies brought on upon by...
The vacation rental industry has exploded in the last few years with big players. Big players like AirBnB, HomeAway & Booking.com have been rapidly consolidating the industry, creating an industry with more familiarity that’s palatable to the average consumer. But what does this mean for the “mom-and-pop” style businesses who don’t want to grow? Those who would rather create a small limited edition business...
Bernardo Retana of Otium Residences in Marbella, Spain has a great pedigree of hospitality and finance. But what I like most about his topic here is its unconventionality — it’s innovative in that no one taught him or instructed him to do this. But simple enough that pretty much all of us could do it too. I was drinking beers with Bernardo in Barcelona, Spain at the KigoWorld event, when he shared the Whatsapp...
Lawrie Lawrence is a real estate guy. He loves real estate. he’s really good at real estate. And only recently has he become infatuated with a new kind of real estate, and that’s vacation rentals. But in his typical renegade style, Lawrie doesn’t do anything textbook. What I like most about Lawrie’s boat model is that it is based highly on statistics and evidence. He wouldn’t invest in something that he wasn’t...
Mailie Green manages three vacation rental villas in Bali from her home in South Africa. And like any manager, she is constantly on the lookout for ways to boost occupancy in the low season: she is always open to ideas that result in a win for everyone involved. This particular technique started with a skeptical email...but it has turned into one of her regular booking channels, while simultaneously benefiting...
Alex Barba was the General Manager at BCN Apartments when we recorded this conversation -- it's a boutique vacation rental fleet in Barcelona, Spain. And while he's not there anymore, the way he helped change my perspective on start-ups, acquisitions, and problem solving in our young vacation rental industry still whispers at me regularly. It's a creative solution for any property manager not satisfied with...
Brad Stewart of Stewart Mountain Lodging in Sundance, Utah is one of my best buddies in the industry. I think it’s fair to say that I admire his work as much as he appreciates mine. More specifically, I really admire how Brad thinks in systems and processes. And as a property manager, one of Brad’s big turning points was with regards to his owners: like we’d strengthen any good relationship, he and Vicky created...
John Dean of Only Provence is what I like to refer to as one of the most limited edition property managers in the world. His fleet of properties are widely recognized as the best properties in the Provence region of France. But this distinction does not happen by accident. I was in Barcelona, Spain at KigoWorld when John told me about this tactic. I asked him to step into the side room and we archived it for...
It's not often I meet a mastermind like Jeanne Dailey, she's the Founder and CEO of Newman-Dailey Resort Properties in Destin, Florida. Like many vacation rental professionals, Jeanne is keen on the idea of diversification. But unlike many vacation rental professionals, Jeanne views this concept through an industry lens: having built several pillars in her business to avoid having all her eggs in the vacation...
Durk Johnson is a housekeeping guru. He’s the director of the Vacation Rental Housekeeping Professionals (VRHP) but he’s also the consummate systems thinker: Durk is always looking for a way to systematize or temptatify or create a framework that can be followed and scaled: it could be argued that Durk's ability to do this has the potential to unlock the vacation rental industry as a whole. This interview...
Jeremiah Gall is a vacation rental pioneer: he was one of the founders of the listing site FlipKey, which was eventually sold to TripAdvisor. And not willing to leave the industry, Jeremiah’s latest brainchild is Breezway which is an app that allows hosts to optimize the operations of their vacation rental businesses. After the Streamline conference in Phoenix, Arizona I got the chance to challenge Jeremiah...
Eric Bay is a connector. He’s the kind of guy that every neighborhood would be lucky to have: he shoots straight, he respects opposing viewpoints, and he’s willing to work hard for the community. Pretty much a model small business advocate. He’s also the President of the Alliance for Neighborhood Prosperity, which, based in New Orleans, is one of the most influential short-term rental advocacy groups in the...
Mike Harrington was the de-facto head of VRMA up until a few hours after our conversation. He’s also the President of Topsail Realty in North Carolina which was hit by a nasty hurricane in September. Almost 75% of Mike’s properties had damage so this was a pivotal learning experience for him and his team. Mike’s big saving grace was trip insurance. If you’re the kind of person who thinks a natural disaster...
Jeff Jensen and his team of concierges at Utopian Luxury Vacation Homes believe that personalization is luxury: that placing your favorite newspaper or a hat from your alma mater in your vacation rental can convey thoughtfulness and win repeat business. But in order to personalize you need to know something about those guests — something personal. So from the moment of receiving the inquiry, Jeff’s...
Jean-Philippe Ramé of 2 Be Apart in Lyon France is something of a vacation rental icon: he’s one of those entrepreneurs that sort of transcends industry and his management fleet is about as personality-driven as anything I’ve ever seen (check out the website if you don’t believe me). It was in Barcelona, Spain at the KigoWorld event that Jean Philippe was sharing with me his strategy for baking flavor into...
Zaira Guzman is the Director of Sales and Revenue Management at Bluewater Vacation Homes in San Diego. Since San Diego is such a competitive vacation environment, Bluewater's recent occupancy growth (month upon month) isn't attributable to much other than Zaira's dynamic pricing skills, which means changing the nightly rates of properties to generate a fair return for the owner and a great value for the guest...
Danna Kittell is the founder of Starfish Luxury Rentals on the coast of Oregon. Her enthusiasm and positivity for the industry is eclipsed only by her hard work. After doing some rehab to her family's vacation home, she and her husband Jeff realized the potential of having a renovation aspect to their management services: upgrading a diamond in the rough has now become Starfish's secret weapon. It's not a...
I only met Steve a few years ago but he's been leading the PM charge for eons with his company VTrips and he can also be spotted on the speaking circuit at conferences around the world: shooting straight and saying some of the things that others may not like...but need to hear. I had the chance to sit down with Steve in Barcelona, Spain this month after we bumped into each other at the airport en route to the...
Bradie Beagley-Reiner went through an incredibly stressful process in the crackdown of vacation rentals in San Diego, California. And in hindsight, she realized that a whole new kind of sharing economy sits within just beneath the surface: something we can all begin doing before it's too late. The instinct of independent vacation rental professionals is not always to get together with their competitors or...
Kristi Kautz used to work in the digital entertainment space, so she was familiar with the world of influencers before her property manager Brad Klopman of The CoHost Company suggested offering a few free nights to some instagram influencers in exchange for a fresh set of photos. The tactic ended up becoming a way to unlock their vacation rental, Starship Landing Retreat, to the right kinds of travelers. If...

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