No Real Estate Background - 40+ STRs Later (HERE'S HOW) - with Alex Steeg

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 - ⁠⁠⁠⁠⁠⁠  / ⁠  
• Instagram - ⁠⁠⁠⁠⁠⁠  / ⁠  
• Website - ⁠⁠⁠⁠⁠⁠https://www.shorewaymgmt.com/⁠

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