117 - From Zero to Market Leader in Hot Springs, Arkansas | Carey Antoon of Overnight Digs

What does it look like to build a luxury STR management company from scratch, keep your W2, win a Home Innovation Award before your second birthday as a business, and position yourself for acquisition all at the same time? Carey Antoon is doing exactly that, and this conversation is one of the most grounded and relatable episodes the show has had. Matt and Austin sit down with Carey Antoon, founder of Overnight Digs, the premier luxury vacation rental and property management company serving Hot Springs and Lake Hamilton in Arkansas. Hot Springs is a unique and thriving STR market, home to the nation's first national park, healing thermal waters, a legendary historic downtown, and the only horse racetrack in Arkansas, all of which draw millions of visitors a year looking for an experience that goes beyond a standard hotel room. Carey saw the opportunity and built a boutique, concierge-level brand to serve it. Founded in 2022 by three families and fellow investors, Overnight Digs grew from a single investment property to nearly 50 doors in under three years and was recognized with a Home Innovation Award before most companies even find their footing. The brand has become synonymous with luxury in the Hot Springs market and Carey is already thinking several moves ahead. Here is what you will learn: How Carey got into STRs after selling out of a franchise business and why he chose short-term rentals over other asset classes for the tax benefits and cash flow, how he structured his management company partnership from day one with a licensed broker on record and why that decision paid off, what it is like to build and grow an STR business while still working a W2 and managing time between two worlds, why Carey calls STRs lifestyle assets and how that framing shapes the way he thinks about his portfolio and his future, how Overnight Digs built a reputation as the luxury operator in Hot Springs and what concierge-level service actually looks like in practice, how he thinks about acquisitions and the possibility of acquiring other boutique STR brands to expand his portfolio, and why he is seriously considering attending VRMA for the first time and what he hopes to get out of it. Carey also shares his honest take on what it means to set up a business the right way from the start, even when you do not know yet how big it will become. Find Carey and Overnight Digs on all social media channels at @overnightdigs or visit overnightdigs.com to learn more and book direct. You can also email at Care@overnightdigs 👥 Follow The Show The Co-Host Bros Podcast Instagram: @cohostbros Facebook: @cohostbros YouTube: @cohostbros TikTok: @cohost.bros ⸻ Follow the Hosts Matt Codd Instagram: @creativecodds TikTok: @creativecodds Facebook: @matt.codd.3 LinkedIn: https://www.linkedin.com/in/matthew-codd-9a3761375/ Austin Spitzenberger Instagram: @austin_spitzz TikTok: @austin_spitzz Facebook: @austin.spitzenberger LinkedIn: https://www.linkedin.com/in/austin-spitzenberger-70481111b/