Podcast

Zen and the Art of Real Estate Investing with Jonathan Greene

194: Learning To Bet On Yourself as a Real Estate Investor with Andrew Owlett

When boutique hotels started gaining popularity, today’s guest moved from single-family investing into the burgeoning boutique hotel space.

On this episode of Zen and the Art of Real Estate Investing, Jonathan interviews Andrew Owlett, a former firefighter who transitioned into real estate investing. Andrew is a developer of hotels, short-term rentals, long-term rentals, and now boutique hotels with a wellness twist. He is also the founder of Night Owl Academy, Night Owl Management, Night Owl Capital, and STR on Auto-Drive.

Jonathan and Andrew begin their discussion by exploring Andrew’s experience as a firefighter, which led to PTSD and, ultimately, real estate investing and wellness. Andrew explains the importance of building camaraderie and community to create a positive impact for remnants and guests, as well as getting your spouse or partner on board with investing. You’ll hear what appeals to Andrew about boutique hotels and invisible personalization, how he got his start with a townhome in Baltimore, and how he stays focused on the customer experience and business optimization. Andrew explains why he and his wife are both still at their W2s, hiring others to take care of the things you don’t enjoy, and creating hospitality for hotel guests while depending on their online reviews of your property.

Boutique hotels are a unique way to reap the benefits of short-term rentals and multifamily while offering experiences for guests. Andrew Owlett is passionate about this investing niche and is sharing the benefits with others.

In this episode, you will hear:

Andrew Owlett’s transition from his job as a firefighter and struggling with PTSD into real estate investing and wellness
Building camaraderie and community with others to make a positive impact for tenants and guests
Having your spouse or partner on board and supporting one another
The appeal behind boutique hotels and implementing invisible personalization
How Andrew got his start with real estate investing using a townhome in Baltimore and what it taught him
Not being 100% hands-off but remaining focused on customer experience and business optimization
Why Andrew is still at his W2 and who is transitioning out first
Hiring people to take care of the things you don’t enjoy and starting small
Creating hospitality for guests in a boutique hotel environment, reviews, and the downsides of not being able to screen guests

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