Exploring Unique Stays and Investing in Real Estate

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Ben Wolff discusses the concept of unique stays and their impact on the modern traveler. He shares his journey in real estate, from building an Airbnb management portfolio to raising a real estate fund. The chapter also covers their experience during the COVID-19 pandemic and the challenges they faced in acquiring properties.

Patrick Donley (@JPatrickDonley) sits down with Ben Wolff to discuss his strategy of building a “unique stays” portfolio. You’ll also hear about how Ben first got involved in the Airbnb/STR market, how he went about his first unique stay development, how he thinks about taking on risk and making entrepreneurial moves, and how he is building his team at Onera.

Ben co-founded a fund overseeing $65 million in experiential hospitality real estate, featuring treehouses, safari tents, and container homes. He's the CEO of StayOasi, an experiential hospitality management firm, and played a key role in developing StayOasi properties like Onera and Spirit of Sophia.

IN THIS EPISODE, YOU’LL LEARN:

00:00 - Intro

02:10 - Why Ben feels “unique stays” are the way of the future.

03:43 - How Ben first got involved in the Airbnb STR market.

06:02 - How he handled the fallout from the pandemic.

08:59 - How he went about finding land for his first development.

14:34 - Ben’s strategy has been for raising money for his projects.

16:20 - How they went about finding great designs for the treehouses.

27:00 - How Ben went about building a direct booking engine through social media.

32:43 - How Ben thinks about making career decisions.

35:35 - What the books and people that have influenced his entrepreneurial career have been.

39:09 - How he has gone about building the team at Onera.

45:19 - What his new project in Texas is going to look like.

53:14 - What an average day looks like for Ben.

54:36 - Why Ben and his team are increasingly focused on content creation.

57:07 - Why he feels the higher-end unique stays market has much more room to grow.

*Disclaimer: Slight timestamp discrepancies may occur due to podcast platform differences.

BOOKS AND RESOURCES

Join the exclusive TIP Mastermind Community to engage in meaningful stock investing discussions with Kyle and the other community members.
Sign up for TIP’s free newsletter, We Study Markets.
The Everything Guide to House Hacking by Robert Leonard.
Related episode: Listen to REI135: Unique Multi-Unit Airbnb/STR w/ Isaac French, or watch the video.
Related episode: Listen to REI192: Building an Empire w/ Nick Huber, or watch the video.
Related episode: Listen to REI170: Transforming Spaces w/ Antonia Botero, or watch the video.
How to Win Friends and Influence People by Dale Carnegie.
Stayonera.com to book.
Onera’s Instagram.

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