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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...


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...


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...


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...


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...


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...

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Here Goes Nothin'

Retreats, workshops, and discussions that spark creative leaps in your business.

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Upcoming Retreats

Matt's first Here Goes Nothin' retreat is slated for THIS NEW YEARS Dec 26-30 (cohort 1) and Dec 30-Jan 3 (cohort 2).

This retreat is all about creativity as an advanced leadership technique and is open to anyone exploring more creative risks in business (and life!)

Simply reach out to [email protected] with a bit about your current goals to learn more...

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