--- title: Cracking the Code to Profitable Midterm Rentals - with Mike Stone description: Mike Stone's transition from corporate attorney to short-term rental entrepreneur image: https://str.legal/hubfs/166c05-024-67d3-004d-1ca8514cb82_tommy_and_mike_horizontal.jpg --- [Skip to main content](https://str.legal/smartstay-show/mike-stone#main) [![FullLogo_Transparent_NoBuffer-2](https://str.legal/hs-fs/hubfs/FullLogo_Transparent_NoBuffer-2.png?width=300&height=82&name=FullLogo_Transparent_NoBuffer-2.png) ![FullLogo_Transparent_NoBuffer-2](https://str.legal/hs-fs/hubfs/FullLogo_Transparent_NoBuffer-2.png?width=300&height=82&name=FullLogo_Transparent_NoBuffer-2.png) ![FullLogo_Transparent_NoBuffer-2](https://str.legal/hs-fs/hubfs/FullLogo_Transparent_NoBuffer-2.png?width=300&height=82&name=FullLogo_Transparent_NoBuffer-2.png) ![FullLogo_Transparent_NoBuffer-2](https://str.legal/hs-fs/hubfs/FullLogo_Transparent_NoBuffer-2.png?width=300&height=82&name=FullLogo_Transparent_NoBuffer-2.png)](https://str.legal) - [Podcast](https://str.legal/smartstay-show) - [Contact Us](https://str.legal/contact) Open main navigation Close main navigation - [Podcast](https://str.legal/smartstay-show) - [Contact Us](https://str.legal/contact) - Search - [Get Started](https://str.legal/get-started) [Get Started](https://str.legal/get-started) Search [SmartStay Show](https://str.legal/smartstay-show) # Cracking the Code to Profitable Midterm Rentals - with Mike Stone ![Rory Gill](https://app.hubspot.com/settings/avatar/52a7403c0c5152799543ceb531cdb16d) Nov 5, 2024 7:00:00 AM 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://www.youtube.com/redirect?event=video_description&redir_token=QUFFLUhqbGo2bG52aHZXSWJiSWZrWGdBMTNmNW1pNzBrd3xBQ3Jtc0tuNDR0VUZ1XzJNSGdtNkJKdmVaLVVkUjZEVXpwcU40RURacUxsSlR0X1RiMDVYMkxyQmUyUWJoMVJSemJqSklkb1ZUeEpndlJSU1Rtdll1MkVYLVFPWHFDY2R3Vy1GbF9YRnhjblhlNl9EWWRQWmNaMA&q=https%3A%2F%2Fwww.strignite.com%2F&v=ncsHoO2cBfg) / [https://allstr.com](https://www.youtube.com/redirect?event=video_description&redir_token=QUFFLUhqbDdZeS1iMXdTejBKeHhKWGQ1ZE9lT1laWWJqZ3xBQ3Jtc0trVFF5YWN0WGxtcV9GTXJGaE9jZDktQUVPdXYwVlVUdklvUGdrZFNiNHlfc1hBb1dsRWN3Q2p0UmZTNlNXZzY5NmpsSHVzTlBVNXRfOFlLQ3RNcDhwUnBsd3hPRVlrQlZDbm9nYjZHU2NNRTNxTmFZNA&q=https%3A%2F%2Fallstr.com%2F&v=ncsHoO2cBfg) - Linkedin - [ ![](https://www.gstatic.com/youtube/img/watch/social_media/linkedin_1x.png) / mike-stone-5a303b31  ](https://www.youtube.com/redirect?event=video_description&redir_token=QUFFLUhqbnBKbGEtTWxiSGJOWWJGMm9ZaXNvVW5vUTZtZ3xBQ3Jtc0ttNnJhVkw0eWc4QzRHRnZoRnFIXzJrTklnSEtlcC1vUEpXdmZHV2tRRmY0azRSNHBvYkpEZFpZSTJJRDdnTUJhSWliWmZ1ZHVwckNuTG5JV19yc1ptbVhpRjB2a1NLMVN3LVlNeTRPdFNsWGR2R1JCSQ&q=https%3A%2F%2Fwww.linkedin.com%2Fin%2Fmike-stone-5a303b31%2F&v=ncsHoO2cBfg) - Facebook - [ ![](https://www.gstatic.com/youtube/img/watch/social_media/facebook_1x.png) / about  ](https://www.youtube.com/redirect?event=video_description&redir_token=QUFFLUhqa195dmpWVGxNSWMwVVYwN2RJYngwN0tEYUszQXxBQ3Jtc0tuZ1l3VlB0aW5yWVBCamZkY1NtZzVFT2lPS1NLOWduaTFRbVgweUNtZDFXc0I4ZUJlQVlveGF0TE5OSlJ0bUFZVGdDejU2RDRDMmpveFdLTGNtTlVqWE84QTR3LVo5R2drcXk0V2JWVjNjSHZXQ2NoSQ&q=https%3A%2F%2Fwww.facebook.com%2Fmstone219%2Fabout&v=ncsHoO2cBfg) ➢ Subscribe: [  ![](https://www.gstatic.com/youtube/img/watch/yt_favicon_ringo2.png) / @smartstayshow  ](https://www.youtube.com/channel/UC9hSZeHoPAwF2bcEib0RCvg) - [0:00:00](https://www.youtube.com/watch?v=ncsHoO2cBfg&t=0s) Turning Skills into Rental Income - [0:00:09](https://www.youtube.com/watch?v=ncsHoO2cBfg&t=9s) $12,000/Month Rental Contract - [0:00:21](https://www.youtube.com/watch?v=ncsHoO2cBfg&t=21s) From Attorney to Rental Entrepreneur - [0:00:29](https://www.youtube.com/watch?v=ncsHoO2cBfg&t=29s) Risks and Rewards of Airbnb Arbitrage - [0:01:03](https://www.youtube.com/watch?v=ncsHoO2cBfg&t=63s) Becoming an Airbnb Superhost - [0:01:44](https://www.youtube.com/watch?v=ncsHoO2cBfg&t=104s) Lessons from Airbnb Arbitrage - [0:03:00](https://www.youtube.com/watch?v=ncsHoO2cBfg&t=180s) Downsides of Airbnb Arbitrage - [0:06:09](https://www.youtube.com/watch?v=ncsHoO2cBfg&t=369s) Selling the Arbitrage Approach - [0:08:16](https://www.youtube.com/watch?v=ncsHoO2cBfg&t=496s) Securing a $33,000/Month Rental - [0:10:10](https://www.youtube.com/watch?v=ncsHoO2cBfg&t=610s) Building Insurer Relationships - [0:13:05](https://www.youtube.com/watch?v=ncsHoO2cBfg&t=785s) Budgets vs. Feelings in Negotiations - [0:14:54](https://www.youtube.com/watch?v=ncsHoO2cBfg&t=894s) Targeting Insurers for Medium-Term - [0:18:33](https://www.youtube.com/watch?v=ncsHoO2cBfg&t=1113s) Shifting Focus from Renters to Entities **Tags:** ### Related Articles ### Comments ![SmartStay Coaching (transparent background).png-3](https://str.legal/hubfs/SmartStay%20Coaching%20(transparent%20background).png-3.avif) ### Short-Term Rental Counsel + Coaching Welcome to the SmartStay Show, where profit meets strategy for short-term rental hosts. Hosted by STR.Legal Attorney Rory Gill and 30-time Airbnb Superhost Jason Muth, this podcast is your go-to resource for mastering the world of vacation rentals on platforms like Airbnb and Vrbo. Each episode is packed with actionable tips and real-life strategies designed to help you maximize your income while safeguarding your property. Whether you're just starting out or looking to enhance your existing listings, the SmartStay Show covers everything from pricing optimization and guest communication to legal compliance and automation tools. With expert advice from seasoned hosts and industry insiders, we provide the playbook for turning your rental into a top-performing asset. What sets us apart is our focus on owners of small but mighty portfolios. You don’t need to own dozens of properties to succeed — we specifically cater to hosts who self-manage and want to get the most out of their vacation rentals.   ###### Categories ###### Recent Posts [![FullLogo_Transparent_NoBuffer](https://str.legal/hs-fs/hubfs/FullLogo_Transparent_NoBuffer.png?width=250&height=142&name=FullLogo_Transparent_NoBuffer.png)](https://str.legal) 40R Merrimac Street, Suite 201 East Newburyport, MA 01950   [978-351-9050](tel:9783519050)   ©2026 STR Legal PC. All rights reserved. Licensed in Massachusetts and New Hampshire.  [Privacy Policy](https://str.legal/privacy). - - - ```json { "@context" : "https://schema.org", "@type" : "BlogPosting", "author" : { "@type" : "Person", "name" : "Rory Gill", "url" : "https://str.legal/smartstay-show/author/rory-gill" }, "dateModified" : "2025-01-03T15:04:51.343Z", "datePublished" : "2024-11-05T12:00:00.000Z", "headline" : "Cracking the Code to Profitable Midterm Rentals - with Mike Stone", "image" : [ "https://str.legal/hubfs/166c05-024-67d3-004d-1ca8514cb82_tommy_and_mike_horizontal.jpg" ], "mainEntityOfPage" : { "@id" : "https://str.legal/smartstay-show/mike-stone", "@type" : "WebPage" }, "publisher" : { "@type" : "Organization", "logo" : { "@type" : "ImageObject", "url" : "https://str.legal/hubfs/FullLogo_Transparent_NoBuffer.png" }, "name" : "STR Legal" } } ```