How a Tech Sales Guy Built an Airbnb Business on Cape Cod (Unfiltered) | Matt Cutler

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0:00 – Introduction & Matt’s Real Estate Journey
0:42 – Building Relationships in Real Estate
2:51 – Entering the Cape Cod Market
4:29 – First Rental Experiences & Lessons Learned
8:01 – Managing Neighbors and Community Relations
12:51 – The Cape Cod Vacation Rental Market
14:28 – Amenities and Guest Experience
16:41 – Handling Seasonality and Off-Season Strategies
17:57 – Attracting and Managing Repeat Guests
22:23 – Differentiating as a Property Manager
25:14 – Working with Owner-Occupied vs. Investment Properties
32:27 – Transitioning from W2 to Full-Time Entrepreneurship
38:18 – Advice for Aspiring Real Estate Entrepreneurs
42:02 – Where to Find Matt & Episode Wrap-Up
Let me know if you’d like more detail or additional segments!

Ever wondered what it really takes to leave your 9–5 and build a successful short-term rental business on Cape Cod? 🌊🏡


In this episode, we sit down with Matt Cutler, who made the bold leap from a traditional W2 career to creating a thriving STR operation in one of New England’s most iconic vacation destinations. Matt pulls back the curtain on the emotional and financial realities of leaving corporate life, what it’s like to manage properties in a seasonal market, and why guest experience is everything. He also shares how he builds strong relationships with property owners, attracts repeat guests, and invests in the amenities that actually move the needle.
Whether you’re dreaming of your first rental or scaling a growing portfolio, this episode is packed with hard-earned insights and honest advice you won’t want to miss.
🎧 Hit play and get inspired to take your next big step.


Things we discussed in this episode:
Transitioning from a W2 job to full-time real estate investing and short-term rental management.The journey of starting with a duplex outside Boston and expanding to Cape Cod and St. Augustine Beach.The importance of building relationships with property owners and setting clear expectations.The unique characteristics and predictability of the Cape Cod vacation rental market.Strategies for managing seasonality and filling off-season vacancies, including midterm rentals and platforms like Furnish Finder.The role of amenities and design in attracting guests, especially during shoulder seasons.Approaches to handling repeat guests and the challenges of aligning pricing with market rates.Differentiating as a property manager by focusing on guest experience and continuous improvement.Navigating owner-occupied versus investment properties and managing owner expectations.The challenges and rewards of entrepreneurship, including scaling the business and deciding when to hire additional help.


Get in touch with Matt:


Facebook - ⁠⁠⁠⁠  / beacondestinations⁠  
Instagram - ⁠⁠⁠https://www.instagram.com/beacondesti...
Website - ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://www.beacondestinationsstr.com/⁠


#SmartStayShow #realestate #realestateinvestor #realestateagent #RealEstateInvesting #ShortTermRentals #CapeCod #VacationRentals #Entrepreneurship #PropertyManagement #GuestExperience #MidTermRentals #DirectBooking #BusinessGrowth




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