EP 08: How She is Always Under Contract with Madi from The Love of Upstate

Off Grid with Zoey B

In this episode of Off Grid with Zoey B, we sit down with the powerhouse behind some of the most iconic short-term rentals in Upstate New York—Madi. Known for her unmatched eye for design, next-level underwriting skills, and lightning-fast execution, Madi shares the behind-the-scenes journey of how she and her partner Skyler built a thriving real estate business from scratch.

From discovering rental arbitrage via a chatty Uber driver in San Francisco to flipping and living in a “sneaky duplex” in Big Bear, to now dominating the Upstate NY STR scene—Madi brings the receipts and the strategy. You'll learn how she went from startup life to analyzing nationwide deals, why she's obsessed with old homes and waterfront properties, and how she curates properties that are not just beautiful but wildly profitable.

💥 What You’ll Learn:

• How to trust your gut when the numbers don’t tell the full story
• Creating a branded STR portfolio that speaks directly to your ideal guest
• Madi’s go-to strategy for furnishing, photographing, and launching homes FAST
• Why design is more than aesthetics—it’s a marketing weapon
• Lessons from running mega-homes and tips for staying ahead in today’s market

Whether you're an investor, host, or just love a good real estate glow-up, this episode is packed with insight, strategy, and aesthetic inspiration.

🎧 Tune in and take notes—Madi doesn’t gatekeep.

Ready to build a lifestyle aligned real estate portfolio? Apply for the Rooted in Rentals Mentorship and Interview with Zoey to join the community: https://www.zoeyberghoff.com/rnrmentorship

Get Zoey’s free resources for her listenings and stay in the know with the monthly Rooted Report here: https://www.zoeyberghoff.com/tools

Exclusive discounts and free trials from brands Zoey loves for her listeners. Unlock them here: https://www.zoeyberghoff.com/resources-