How We Helped 200+ Investors Use the STR Loophole Blake Anthony Carter + Jeremy Courtney

What does it really take to scale a short-term rental business, and when does “more” stop meaning “better”? In this episode, we sit down with Blake and Jeremy from Cribs Consulting, the powerhouse duo behind one of Austin’s most respected short-term rental operations. We dig into their journey from managing just three Airbnbs to nearly a hundred properties, and the surprising decision to intentionally scale back in order to gain clarity, profitability, and balance. We talk candidly about creative financing strategies, tax-smart moves like the STR loophole, and what it truly means to build a long-term, legacy business alongside your spouse. Blake and Jeremy also share how community events, genuine relationships, and showing up authentically for clients have been key drivers of their success. If you’re a host, investor, or entrepreneur questioning how to grow smarter, not just bigger, this conversation is packed with real-world insight, hard-earned lessons, and plenty of inspiration. Things we discussed in this episode: Blake and Jeremy’s rapid growth from three Airbnbs to nearly 100, and their decision to scale down for quality. Transition from managing co-living, by-the-room properties to focusing on short-term rentals in Austin. The STR (short-term rental) loophole and its tax benefits for high-income earners investing in real estate. The importance of building systems and processes for successful property management. Creative financing strategies, including seller financing and low down payment deals. Differences between Austin’s investment-driven rental market and markets like Provincetown with more second-home owners. The unique challenges and rewards of running a business as a married couple. Building a family legacy and integrating children and family life with business goals. The role of community events and local networking in growing a short-term rental brand. Ongoing goals to improve team training, operations, and business scalability for the future. Get in touch with Blake and Jeremy: Instagram - ⁠⁠⁠⁠⁠⁠ Linkedin - ⁠⁠ Website - ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ ⁠⁠⁠⁠⁠⁠

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How We Helped 200+ Investors Use the STR Loophole Blake Anthony Carter + Jeremy Courtney is an episode from The Real Estate Law Podcast by Airbnb Superhost Jason Muth + Rory Gill.

This episode is 00:49:27 long.

This episode was published on Dec 16, 2025.

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