--- title: No Real Estate Background - 40+ STRs Later (HERE'S HOW) - with Alex Steeg description: In this episode, we sit down with Alex Steeg, a short-term rental entrepreneur who's built a thriving business across Boston’s North Shore. image: https://str.legal/hubfs/Slack%20Profile%20Picture%202_JPG.jpg.avif --- [Skip to main content](https://str.legal/smartstay-show/alex-steeg#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) # No Real Estate Background - 40+ STRs Later (HERE'S HOW) - with Alex Steeg ![Rory Gill](https://app.hubspot.com/settings/avatar/52a7403c0c5152799543ceb531cdb16d) Jun 10, 2025 2:22:39 PM What does it take to grow from managing one small rental to overseeing 40+ short-term properties in just seven years? In this episode, we sit down with Alex Steeg, a short-term rental entrepreneur who's built a thriving business across Boston’s North Shore. His journey is nothing short of inspiring—from starting with a modest two-family property to managing a diverse and growing portfolio. Alex shares how his early career in residential advising unexpectedly prepared him for the world of property management. Alongside his wife Rachel, he began with traditional long-term rentals before discovering the game-changing potential of short-term stays—unlocking significantly higher cash flow and more flexibility. Today, Alex manages everything from cozy studios to expansive 22-acre estates, and he’s in the middle of renovating a 10-unit inn in Ipswich. He dives into the strategies that helped him scale, the lessons learned along the way, and how intentional planning and adaptability have fueled his success. Whether you’re just starting out or looking to grow your own STR business, this episode is packed with real-world insights and inspiration. Things we discussed in this episode: - Alex Steeg's career transition from seminary and residential advising to short-term rental management - The founding of Shoreway Management by Alex and his wife Rachel, growing to over 40 properties - Their strategic approach to real estate investing, starting with a two-family property in 2018 - The game-changing impact of short-term rentals on their cash flow and business growth - Alex's recent purchase and renovation of the 10-unit Ipswich Inn, managing a complex commercial property renovation - The importance of complementary skills in a spouse-run business, with Rachel handling operations and Alex focusing on client relations - Their geographical focus on managing properties along Boston's North Shore, including towns like Marblehead, Salem, and Gloucester - Being named a top-rated short-term rental management company by AirDNA - The challenges and benefits of working together as a married couple in a business - Their involvement with Smart Stay coaching and helping other aspiring real estate investors and short-term rental operators Get in touch with Alex: - Facebook - ⁠⁠⁠⁠⁠⁠[ ![](https://www.gstatic.com/youtube/img/watch/social_media/facebook_1x.png) / ⁠  ](https://www.youtube.com/redirect?event=video_description&redir_token=QUFFLUhqblR6VGdnX1N6VlZDcHVMNDRnTmpZdkk3cWo2Z3xBQ3Jtc0ttSHd0Yy1GbmdsQ1ZNTVFBWXZXb2tqX1hCRXVDOVFqNlNyMC0za2lDS3Y4a0NFQ3Z2aG5oVkdKT2wwSTdWVlZOZXFSX2ZkQUFQYWlJUmsxX3d1VEs4dlozY0J4TkdjVmRKSld3M2J1MGlYb2prTWxiRQ&q=https%3A%2F%2Fwww.facebook.com%2Falex.steeg86%2F%E2%81%A0&v=GRHzgzCLadU) - Instagram - ⁠⁠⁠⁠⁠⁠[ ![](https://www.gstatic.com/youtube/img/watch/social_media/instagram_1x.png) / ⁠  ](https://www.youtube.com/redirect?event=video_description&redir_token=QUFFLUhqbjFNRkdKeXRwVmNCVzhpTXJEM2czZkUwLWlDUXxBQ3Jtc0tuSnNtc3pkU1ljWGlOc1F5YmhydE51ckE3NGZhb1JaRUJJdEZ2VWJrcjljdEROMGFsV21ZdjNGbTRXZkNFZUM0ODZSd3dkbXhfbEs4Vk5fVGsxcVVMcEZfUE9KWlhLc0VZVUVmNnRMN0tIZlFoRzZjUQ&q=https%3A%2F%2Fwww.instagram.com%2Falexsteeg%2F%E2%81%A0&v=GRHzgzCLadU) - Website - ⁠⁠⁠⁠⁠⁠[https://www.shorewaymgmt.com/⁠](https://www.youtube.com/redirect?event=video_description&redir_token=QUFFLUhqbUtFemlqYmVRSkpaeW9LTkJ5dDBVVGF5OHRtZ3xBQ3Jtc0trM2l5UWN2Umc0cE9yczlLX0pmcndLaG1SUmdRTmxFZ2daMktTcnkwNmZEcFdpcGFUZjVtRnpablZ1WkxVTjV1elBJMGtNYlZrM2c2d3RBbE93T0ZjZUhVS3VSNURSVGFjY0g4N3FxS3VyYTRqWURKZw&q=https%3A%2F%2Fwww.shorewaymgmt.com%2F%E2%81%A0&v=GRHzgzCLadU) ➢ Subscribe: [  ![](https://www.gstatic.com/youtube/img/watch/yt_favicon_ringo2.png) / @smartstayshow  ](https://www.youtube.com/channel/UC9hSZeHoPAwF2bcEib0RCvg) **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" : "2025-06-10T18:22:39.791Z", "datePublished" : "2025-06-10T18:22:39.000Z", "headline" : "No Real Estate Background - 40+ STRs Later (HERE'S HOW) - with Alex Steeg", "image" : [ "https://str.legal/hubfs/Slack%20Profile%20Picture%202_JPG.jpg.avif" ], "mainEntityOfPage" : { "@id" : "https://str.legal/smartstay-show/alex-steeg", "@type" : "WebPage" }, "publisher" : { "@type" : "Organization", "logo" : { "@type" : "ImageObject", "url" : "https://str.legal/hubfs/FullLogo_Transparent_NoBuffer.png" }, "name" : "STR Legal" } } ```