What does it take to walk away from a high-paying corporate job and build a 50+ property short-term rental empire?

In this episode, I sit down with real estate investor and coach Matt McCall Stillman, along with attorney and legal expert Rory Gill, for a powerful conversation about what it really takes to succeed in the short-term rental world.

We dive into Matt’s journey—how he went from corporate burnout to STR powerhouse—and unpack the mindset shifts, calculated risks, and coaching that helped him scale. Along the way, we explore market trends, legal must-knows for investors, and why having local knowledge and legal support can make or break your success.

Whether you're managing your first listing or looking to grow your portfolio, this episode is full of raw insight, practical advice, and stories that will inspire and inform your next move.

👉 Don't forget to like, subscribe, and hit the bell for more STR success stories and tips!

Things we discussed in this episode:

From Corporate to Real Estate: Matt's Bold Career Shift

Why Mindset Matters in Entrepreneurship

How Matt Scaled to 50+ Properties

The Real Value of a Great Coach in Real Estate

STR Market Trends: Design, Amenities & Regulations

Seasonality & Revenue Strategy in Short-Term Rentals

Local vs. Remote Investing: What Works Best?

Lessons Learned from Hotel Ownership

Legal Must-Knows for STR Investors

Top Advice for First-Time STR Buyers

Get in touch with Matt:

Facebook - ⁠⁠https://www.facebook.com/MyBrokerMatt

Instagram - ⁠https://www.linkedin.com/in/mybrokermatt/

Website - ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://go.thestrlegend.com/mastermind

#SmartStayShow #realestate #realestateinvestor #realestateagent #RealEstateInvesting #AirbnbInvestment #RealEstateSuccess

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Join Jason Muth of Prideaway Stays and Straightforward Short-Term Rentals and Real Estate Attorney / Broker Rory Gill for the first 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

Straightforward Short-Term Rentals ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Website⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ and on ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Instagram⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠

Attorney Rory Gill ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠on LinkedIn⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠

Jason Muth on ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠LinkedIn⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠

Ever wonder what it really takes to pack up your life, move to a new city, and build a short-term rental business from scratch?

In this episode, We sat down with my friend Chachi Horgan — a former real estate agent from Maine who took a leap, moved to Florida, and built Roam Ready Vacation Rentals, scaling to 11 properties in less than two years.

We talk about everything — the mindset it took to start over, the power of building a solid network, what it’s like navigating a new market, and why learning to delegate is absolutely critical if you want to grow. Chachi also shares how coaching lacrosse and a love of personal development shaped how he runs his business today.

If you're thinking about starting a vacation rental business — or scaling the one you already have — this one's loaded with real stories, raw insights, and some seriously motivating perspective.

Things we discussed in this episode:

Get in touch with Chachi:

Facebook - ⁠https://www.facebook.com/chachi.horgan

Instagram - https://www.instagram.com/the_realestate_chachi/

Website - ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://roamreadyvacationrentals.com/

#SmartStayShow #realestate #realestateinvestor #realestateagent #RealEstateInvesting #AirbnbInvestment #RealEstateSuccess

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Join Jason Muth of Prideaway Stays and Straightforward Short-Term Rentals and Real Estate Attorney / Broker Rory Gill for the first 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

Straightforward Short-Term Rentals ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Website⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ and on ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Instagram⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠

Attorney Rory Gill ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠on LinkedIn⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠

Jason Muth on ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠LinkedIn⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠

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!

Can a side hustle built on friendship and a love of travel become something bigger?

Join Jason Muth, Rory Gill, and Ethan Sobel as they share the real story behind Prideaway Stays, their co-hosting venture in Provincetown. From a family dream of owning a Cape home to building a guest-first rental brand, this episode dives into the heart of short-term rental hosting.

Discover how they scaled their business while staying personal, built community connections, and turned passion into purpose.

🎧 A must-listen for anyone curious about real estate, entrepreneurship, or the power of partnership.

Things we discussed in this episode:

Ethan’s Cape Cod Investment Origin

Founding Pride Away Stays

Emotional Drivers in STR Investing

Scaling with a Personal Touch

Building Trust with Owners & Guests

Seasonality & Slow Growth in Ptown

Diverse Team & Strong Systems

Friendship to Business Partnership

STRs as Income & Fulfillment

Community-Focused Hosting Mission

Get in touch with Fouad:

Facebook - https://www.facebook.com/prideawaystays/

Linkedin - ⁠⁠⁠⁠⁠⁠⁠⁠⁠https://www.linkedin.com/company/98969932/admin/dashboard/

Website - ⁠⁠⁠⁠⁠⁠⁠⁠⁠https://prideawaystays.com/

#SmartStayShow #realestate #realestateinvestor #realestateagent #RealEstateInvesting #PridewayStays #ProvincetownRentals #STRBusiness #VacationRentals #GayOwnedBusiness #AirbnbTips #TravelCommunity #EntrepreneurJourney

Follow Us!

Join Jason Muth of Prideaway Stays and Straightforward Short-Term Rentals and Real Estate Attorney / Broker Rory Gill for the first 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

Straightforward Short-Term Rentals ⁠⁠⁠⁠⁠⁠⁠⁠⁠Website⁠⁠⁠⁠⁠⁠⁠⁠⁠ and on ⁠⁠⁠⁠⁠⁠⁠⁠⁠Instagram⁠⁠⁠⁠⁠⁠⁠⁠⁠

Attorney Rory Gill ⁠⁠⁠⁠⁠⁠⁠⁠⁠on LinkedIn⁠⁠⁠⁠⁠⁠⁠⁠⁠

Jason Muth on ⁠⁠⁠⁠⁠⁠⁠⁠⁠LinkedIn⁠⁠⁠⁠⁠⁠⁠⁠⁠

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!

What if your best-performing Airbnb was sitting just a mile away—and you almost missed it?

In this episode, we talk with Jeremy Beland, a real estate investor who made the leap from wholesaling to building a killer short-term rental portfolio in Port St. Lucie, Florida. He shares how one overlooked pocket became home to his top-performing property—and why hyper-local strategy matters more than most people realize.

Jeremy and his wife pull back the curtain on what it really takes to succeed in the Airbnb space. From rehabbing a rundown house to creating a five-star guest experience, they walk through the messy, unglamorous, and essential parts of running short-term rentals like a real business.

Whether you’re already hosting or just thinking about it, this one’s packed with real-world advice, hard-earned lessons, and a few laughs along the way.

Things we discussed in this episode:

Jeremy’s shift from off-market deals to short-term rentals

Why location—down to a one-mile radius—matters

The real challenges of furnishing from scratch

Building a strong local cleaning and maintenance team

Treating STRs like a business, not a side hustle

Smart guest screening to protect your property

How reviews impact long-term success

Jeremy’s REI Freedom program on off-market strategies

Long-term wealth potential of STR investments

The hospitality mindset behind a top-tier Airbnb

Get in touch with Jeremy:

Linkedin - ⁠⁠⁠⁠⁠⁠⁠https://www.linkedin.com/in/jeremy-beland-164b8913/

Facebook - ⁠⁠⁠⁠⁠⁠⁠https://www.facebook.com/groups/795700988329071/media

Instagram - ⁠⁠⁠⁠⁠⁠⁠https://www.instagram.com/jeremybeland_/

#SmartStayShow #realestate #realestateinvestor #realestateagent #RealEstateInvesting #AirbnbInvestment #RealEstateSuccess #PropertyInvesting #STRStrategy #OffMarketDeals #AirbnbTips #RealEstateCoaching #PassiveIncome #PropertyManagement

Follow Us!

Join Jason Muth of Prideaway Stays and Straightforward Short-Term Rentals and Real Estate Attorney / Broker Rory Gill for the first 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

Straightforward Short-Term Rentals ⁠⁠⁠⁠⁠⁠⁠Website⁠⁠⁠⁠⁠⁠⁠ and on ⁠⁠⁠⁠⁠⁠⁠Instagram⁠⁠⁠⁠⁠⁠⁠

Attorney Rory Gill ⁠⁠⁠⁠⁠⁠⁠on LinkedIn⁠⁠⁠⁠⁠⁠⁠

Jason Muth on ⁠⁠⁠⁠⁠⁠⁠LinkedIn⁠⁠⁠⁠⁠⁠⁠

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!

What if your real estate business was designed to serve your life — not run it?

In this episode, we chat with Fouad Bazzi, a former banker who left the corporate world to build a thriving short-term rental business centered around freedom, family, and purpose. He shares how he scaled his operations, mentors the next generation (including his own kids), and shifted from chasing work-life balance to creating true work-life unity.

This isn’t just about real estate — it’s about building a values-driven business that aligns with the life you want. Whether you're an investor or just curious about the space, this conversation will challenge and inspire you. Hit play and get ready to rethink success.

Things we discussed in this episode:

Fouad’s shift from banking to STR for time and financial freedom

Goal-driven real estate strategies over social media trends

Rebranding from Crescent Retreats to The Owner Hosts

Involving family in staging and business learning

Building a global team with specialized virtual assistants

Health and fitness as pillars of entrepreneurial success

STR Cohort: action-based consulting and peer learning

Embracing “work-life unity” over balance

Tax strategies and real estate for high-income earners

Creating sellable, legacy-driven businesses

Get in touch with Fouad:

Facebook - ⁠⁠⁠⁠⁠⁠⁠⁠https://www.facebook.com/foubazzi/

Linkedin - ⁠⁠⁠⁠⁠⁠⁠⁠https://www.linkedin.com/in/fouad-bazzi-4415973/

Website - ⁠⁠⁠⁠⁠⁠⁠⁠https://www.fouadbazzi.com/

#SmartStayShow #realestate #realestateinvestor #realestateagent #RealEstateInvesting #OpportunityZones #ShortTermRentals #EntrepreneurLife #FamilyBusiness #FinancialFreedom #AirbnbHost #BusinessMindset #PropertyManagement #EntrepreneurialFamily

Follow Us!

Join Jason Muth of Prideaway Stays and Straightforward Short-Term Rentals and Real Estate Attorney / Broker Rory Gill for the first 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

Straightforward Short-Term Rentals ⁠⁠⁠⁠⁠⁠⁠⁠Website⁠⁠⁠⁠⁠⁠⁠⁠ and on ⁠⁠⁠⁠⁠⁠⁠⁠Instagram⁠⁠⁠⁠⁠⁠⁠⁠

Attorney Rory Gill ⁠⁠⁠⁠⁠⁠⁠⁠on LinkedIn⁠⁠⁠⁠⁠⁠⁠⁠

Jason Muth on ⁠⁠⁠⁠⁠⁠⁠⁠LinkedIn⁠⁠⁠⁠⁠⁠⁠⁠

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!

What if your next real estate deal could help you eliminate capital gains taxes—while building a thriving short-term rental business?

In this episode, tax strategist Ashley Tison dives into the powerful world of Opportunity Zones and how investors can use them to unlock huge tax advantages. These zones aren't just distressed areas—they include beachfront properties, university towns, and booming urban districts.

Ashley explains how to transform a property in an Opportunity Zone, count even furniture and equipment as improvements, and potentially walk away from the investment completely tax-free after 10 years. But there’s a deadline: you’ll need a capital gain by December 31, 2026, and an active business within the zone.

Whether you're eyeing a downtown mixed-use building or a waterfront rental community, this episode shows how to invest with strategy, purpose, and serious long-term upside.

Things we discussed in this episode:

Opportunity Zones: Created by the 2017 Tax Cuts and Jobs Act

Defer and Eliminate Capital Gains by Holding for 10 Years

Short-Term Rentals Qualify—Including Furnishings and Equipment

Act Fast: Final Investment Deadline is December 31, 2026

University Areas Offer Prime OZ Investment Potential

You Must Actively Operate a Business—Not Just Use Personally

Mixed-Use Buildings Are Ideal for OZ Strategies

Meet the ‘Substantial Improvement’ Rule to Qualify

Use SBA Loans to Fund Mixed-Use OZ Projects

Invest Gains from Stocks, Real Estate, or Other Appreciated Assets

Get in touch with Ashley:

Facebook - ⁠⁠⁠⁠⁠⁠⁠https://www.facebook.com/ozpros

Linkedin - ⁠⁠⁠⁠⁠⁠⁠https://www.linkedin.com/company/ozproscom/

Website - ⁠⁠⁠⁠⁠⁠⁠https://ozpros.com/

#SmartStayShow #realestate #realestateinvestor #realestateagent #RealEstateInvesting #OpportunityZones #ShortTermRentals #TaxStrategy #WealthBuilding #TaxSavings #PropertyInvestment #AirbnbInvesting #PassiveIncome #InvestmentTips

Follow Us!

Join Jason Muth of Prideaway Stays and Straightforward Short-Term Rentals and Real Estate Attorney / Broker Rory Gill for the first 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

Straightforward Short-Term Rentals ⁠⁠⁠⁠⁠⁠⁠Website⁠⁠⁠⁠⁠⁠⁠ and on ⁠⁠⁠⁠⁠⁠⁠Instagram⁠⁠⁠⁠⁠⁠⁠

Attorney Rory Gill ⁠⁠⁠⁠⁠⁠⁠on LinkedIn⁠⁠⁠⁠⁠⁠⁠

Jason Muth on ⁠⁠⁠⁠⁠⁠⁠LinkedIn⁠⁠⁠⁠⁠⁠⁠

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!

What does it take to turn a small real estate side hustle into a global corporate housing empire?

In this episode, we sit down with Gary Brown and his son Ken Brown of Furnished Quarters to explore their incredible journey from NYC real estate investors to international leaders in corporate housing. With roots in their family’s furniture business and a knack for strategic growth, this father-and-son duo has helped shape the company’s expansion from a few furnished apartments in Manhattan to a global portfolio of 1,000+ units.

They break down how corporate housing fills a unique niche between hotels and Airbnb—offering professionals fully furnished apartments for 30 days or longer—and explain what truly sets their approach apart when it comes to design, guest experience, and client retention.

From navigating post-COVID market shifts to scaling operations across continents, Gary and Ken share hard-earned insights that every entrepreneur in hospitality, real estate, or short-term rentals needs to hear.

Whether you're new to the space or ready to scale, this episode is packed with lessons in adaptability, service, and smart growth.

Things we discussed in this episode:

Get in touch with Ken and Gary:

Linkedin Ken - ⁠⁠⁠⁠⁠⁠https://www.linkedin.com/in/ken-brown-89555035/

Linkedin Gary - ⁠⁠⁠⁠⁠⁠https://www.linkedin.com/in/gary-brown-b324512/

Website - ⁠⁠⁠⁠⁠⁠https://www.furnishedquarters.com/meet-the-team

#SmartStayShow #realestate #realestateinvestor #realestateagent #RealEstateInvesting #HospitalityTrends #BusinessTravel #PropertyManagement #FurnishedQuarters #RealEstateStrategy #TravelAccommodations #EntrepreneurialJourney

Follow Us!

Join Jason Muth of Prideaway Stays and Straightforward Short-Term Rentals and Real Estate Attorney / Broker Rory Gill for the first 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

Straightforward Short-Term Rentals ⁠⁠⁠⁠⁠⁠Website⁠⁠⁠⁠⁠⁠ and on ⁠⁠⁠⁠⁠⁠Instagram⁠⁠⁠⁠⁠⁠

Attorney Rory Gill ⁠⁠⁠⁠⁠⁠on LinkedIn⁠⁠⁠⁠⁠⁠

Jason Muth on ⁠⁠⁠⁠⁠⁠LinkedIn⁠⁠⁠⁠⁠⁠

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!

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:

Get in touch with Alex:

Facebook - ⁠⁠⁠⁠⁠https://www.facebook.com/alex.steeg86/

Instagram - ⁠⁠⁠⁠⁠https://www.instagram.com/alexsteeg/

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

#SmartStayShow #realestate #realestateinvestor #realestateagent #RealEstateInvesting #AirbnbManagement #EntrepreneurJourney

Follow Us!

Join Jason Muth of Prideaway Stays and Straightforward Short-Term Rentals and Real Estate Attorney / Broker Rory Gill for the first 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

Straightforward Short-Term Rentals ⁠⁠⁠⁠⁠Website⁠⁠⁠⁠⁠ and on ⁠⁠⁠⁠⁠Instagram⁠⁠⁠⁠⁠

Attorney Rory Gill ⁠⁠⁠⁠⁠on LinkedIn⁠⁠⁠⁠⁠

Jason Muth on ⁠⁠⁠⁠⁠LinkedIn⁠⁠⁠⁠⁠

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!

Want to turn your vacation rental into an unforgettable adventure that guests can’t stop talking about?

In this episode of the SmartStay Show, we sit down with Rachel DeSantis — the mastermind behind QR Clue, a groundbreaking in-home escape game that transforms ordinary short-term rentals into immersive, puzzle-filled experiences!

Imagine your guests stepping into a thrilling story where they solve clever puzzles, uncover hidden clues, and win prizes — all through simple, strategically placed QR codes. Rachel shares how this innovative concept not only makes stays wildly fun but also skyrockets your five-star reviews and booking rates.

With quick three-minute setups and fully customizable storylines, QR Clue offers a fresh, tech-savvy way to stand out in a crowded rental market and create lasting memories for your guests. If you’re a host looking to boost your rental’s appeal and provide an experience guests rave about, this episode is packed with insights you don’t want to miss.

Press play and discover how storytelling and technology can literally change the game for your short-term rental business!

Things we discussed in this episode:

Get in touch with Rachel:

Facebook - ⁠⁠⁠⁠https://www.facebook.com/qrclue/

Instagram - ⁠⁠⁠⁠https://www.instagram.com/getqrclue/

Website - ⁠⁠⁠⁠https://www.qrclue.com/

#SmartStayShow #realestate #realestateinvestor #realestateagent #RealEstateInvesting #QRClue #ShortTermRental #AirbnbExperience #TravelTech #HostTips #VacationRental #GuestExperience #EscapeRoom #HospitalityInnovation #STRMarketing

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Join Jason Muth of Prideaway Stays and Straightforward Short-Term Rentals and Real Estate Attorney / Broker Rory Gill for the first 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

Straightforward Short-Term Rentals ⁠⁠⁠⁠Website⁠⁠⁠⁠ and on ⁠⁠⁠⁠Instagram⁠⁠⁠⁠

Attorney Rory Gill ⁠⁠⁠⁠on LinkedIn⁠⁠⁠⁠

Jason Muth on ⁠⁠⁠⁠LinkedIn⁠⁠⁠⁠

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!

Feeling “equity rich” but still cash strapped? You’re not alone—and there’s a smarter way to break free.

In this eye-opening episode, We sit down with Certified Financial Planner Alan Franks to explore how real estate investors can unlock hidden capital, boost returns, and build lasting wealth. Alan shares powerful strategies for using tools like home equity lines of credit and securities-based lending to access cash without selling off valuable assets. He also sheds light on how the post-COVID real estate market has shifted—and how savvy investors are adapting.

With clarity, humor, and real-world examples, Alan unpacks complex financial concepts and shows how to take advantage of tax-saving opportunities, diversify your portfolio, and rethink the way you use leverage.

Whether you're managing multiple short-term rentals or just starting out, this episode will help you think bigger, plan smarter, and make your money work harder. It’s the conversation every real estate investor needs—but probably never had.

Ready to reimagine your investment strategy? Hit play and discover what’s possible.

Things we discussed in this episode:

Use HELOCs to access cash for investment opportunities.

Diversify across real estate and traditional assets.

Borrow against securities to unlock investment capital.

Leverage tax benefits like bonus depreciation and RE pro status.

Adapt to STR shifts post-COVID in supply and demand.

Prioritize appreciation, even with low initial cash flow.

Use credit lines to scale real estate portfolios.

Plan for high rates and increased competition.

Factor opportunity cost into investment decisions.

Balance investments across real estate, retirement, and taxable accounts.

Get in touch with Alan:

LinkedIn - ⁠⁠⁠https://www.linkedin.com/in/alanfranks/

Instagram - ⁠⁠⁠https://www.instagram.com/frankly_financial/

Website - ⁠⁠⁠https://www.empowered-money.com/

#SmartStayShow #realestate #realestateinvestor #realestateagent

Follow Us!

Join Jason Muth of Prideaway Stays and Straightforward Short-Term Rentals and Real Estate Attorney / Broker Rory Gill for the first 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

Straightforward Short-Term Rentals ⁠⁠⁠Website⁠⁠⁠ and on ⁠⁠⁠Instagram⁠⁠⁠

Attorney Rory Gill ⁠⁠⁠on LinkedIn⁠⁠⁠

Jason Muth on ⁠⁠⁠LinkedIn⁠⁠⁠

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!