Cracking the Code to Profitable Midterm Rentals | Mike Stone

Have you ever wondered if the skills you’ve developed in your day job could translate into a thriving business? Meet Mike Stone—a former corporate attorney who transformed his career, channeling his expertise into building a successful short- and medium-term rental empire. Mike’s journey began with an ambitious leap from the legal world into vacation rentals, and his success speaks to the power of leveraging industry insights in new ways. In this episode, Mike opens up about his pivot from attorney to rental entrepreneur, sharing how he secures high-yield, mid-term bookings by targeting insurance companies rather than traditional vacation renters. He provides insider tips on navigating the rental space, detailing his experience with Airbnb arbitrage—a venture that proved costly but ultimately led him to a co-hosting model he’s convinced is far more sustainable and profitable. Tune in as Mike reveals essential strategies for building credibility, tapping into your network, and finding unique opportunities in the rental industry, including landing a $12,000/month contract for a 12,000-square-foot property. Whether you’re curious about the transition into real estate or looking to expand your rental business, Mike’s story offers invaluable lessons and inspiration! Things we discussed in this episode: Mike Stone's transition from corporate attorney to short-term rental entrepreneur His experience with Airbnb arbitrage, including a costly failed deal The benefits of co-hosting over arbitrage, including equity, appreciation, and tax advantages Pro tips for mitigating risk in arbitrage deals The importance of leveraging group reputation to secure initial co-hosting opportunities Mike's recent success in securing a $12,000/month contract for a 12,000 sq ft home The process of building relationships with insurance companies for medium-term rentals The negotiation dynamics when working with insurance companies vs. individual renters Strategies for targeting medium-term rentals during short-term rental slow seasons The value of asking for higher prices and not accepting lower offers from individual renters Get in touch with Mike: Website -https://www.strignite.com / https://allstr.com Linkedin - https://www.linkedin.com/in/mike-stone-5a303b31/ Facebook - https://www.facebook.com/mstone219/about #SmartStayShow #realestate #realestateinvesting #realestateinvestor #realestatelaw #realestateagent #socialmedia #realestatemarketing #ShortTermRentals #MediumTermRentals #Airbnb #RealEstateInvesting #PropertyManagement #CareerChange #PersonalDevelopment #InsuranceCompanies #Masterminds #EntrepreneurLife ***** Join Jason Muth of Prideaway Stays and Straightforward Short-Term Rentals and Real Estate Attorney / Broker Rory Gill for another episode of SmartStay Show! Following and subscribing to SmartStay Show not only ensures that you'll get instant updates whenever we release a new episode, but it also helps us reach more people who could benefit from the valuable content that we provide. ***** SmartStay Show Website and on Instagram and YouTube Prideaway Stays Website and on Facebook and LinkedIn SmartStay Coaching Website and on Instagram Straightforward Short-Term Rentals Website Attorney Rory Gill on LinkedIn Jason Muth on LinkedIn ***** This podcast and these show notes are not legal advice, but we hope you find both entertaining and informative. Hospitality.FM SmartStay Show is part of Hospitality.FM, a podcast network dedicated to bringing the best hospitality-focused podcasts to those in and around the industry, from Food + Beverage, Guest Experience, Diversity & Inclusion, Tech, Operations, Hotels, Vacation Rentals, Real Estate Law, and so much more!