Hassle Free RE

Welcome to our latest episode! Today, we're joined by Jason Muth, Co-Founder and Director of Customer Experience at Prideaway Stays. Jason is a 31x Airbnb Superhost, 29x Vrbo Premier Host, and a full-time entrepreneur who transitioned from a corporate media career to scaling a successful short-term rental and co-hosting business. His story is filled with insights on intentional growth, hospitality, and building a business that aligns with your lifestyle and values.In this episode, Jason shares how one uncomfortable couch and an allergy to cats led to the purchase of his first short-term rental in 2016—and how that one home turned into five owned properties and a thriving co-hosting operation with 17 listings. He walks us through the lessons learned from a major property flood, why having the right insurance partner made all the difference, and how installing generators across his portfolio became a strategic move. Jason also unpacks the launch of Prideaway Stays, his Provincetown-focused management company that blends hospitality, niche branding, and community engagement.If you're curious about how to pivot into co-hosting, build a business that reflects your values, or simply hear how a seasoned host navigated the challenges of growth, this episode is for you. Tune in now to learn how Jason scaled from one rental to a robust hospitality brand—and what he wishes more short-term rental owners understood about success!TIMESTAMPS01:00 – Spring updates and business expansion04:58 – Guest intro: Jason Muth06:08 – How an uncomfortable couch sparked Jason's first short-term rental09:05 – From one rental to five: Jason's early investment journey13:28 – Transitioning from W-2 to full-time entrepreneur17:00 – Using DSCR and vacation loans to scale19:11 – Cost segregation and maximizing depreciation22:01 – The guest-caused flood and $130K in damages24:50 – Why proper insurance is worth every penny29:14 – Installing generators across all properties31:03 – Messaging guests and preparing for power outages33:36 – Neighbor relationships and protecting the business39:02 – Launching Prideaway Stays in Provincetown42:55 – Why niche focus matters: Knowing your target guest48:03 – Second homeowners vs. investors in New England markets50:47 – Giving back and community partnerships at Prideaway53:45 – Final thoughts and where to connect with JasonConnect with the Guest:Website: https://www.prideawaystays.com/Linkedin: https://www.linkedin.com/in/jasonmuth/Instagram: https://www.instagram.com/jasonmuth/Facebook: https://www.facebook.com/jasonmuth/Youtube: https://www.youtube.com/@smartstayshow#ShortTermRentals #AirbnbSuperhost #STRCoHosting #VacationRentalTips #EntrepreneurJourney

Welcome to our latest episode! Today, Dave and Will dive into one of the most crucial aspects of business success—building and managing a high-performing team. They share lessons from their own experiences in hiring, training, and leading virtual assistants (VAs) and in-person teams. Whether you're struggling to delegate or looking to scale your business efficiently, this episode provides actionable strategies for creating a team that operates at a high level.Dave and Will break down the common mistakes entrepreneurs make when hiring VAs, including rushing into hiring without systems, failing to provide clear expectations, and treating VAs as task-rabbits instead of valued team members. They discuss the importance of leadership, vision, and values in building a successful business and why self-awareness is key to becoming an effective leader. Dave shares his process for hiring, onboarding, and structuring virtual teams, including time studies, SOPs, and personality assessments. Will reveals how refining his calendar and improving delegation have transformed his productivity and business growth.Whether you're hiring your first VA or looking to optimize your existing team, this episode is packed with insights on scaling your business, improving leadership skills, and fostering a winning team culture. Tune in now to learn how to delegate effectively, create accountability, and build a business that runs smoothly—without burning out!TIMESTAMPS01:00 – Introduction and updates: boutique hotel management expansion03:07 – The power of masterminds in business growth06:12 – Hiring and leading a virtual team08:50 – Why most people fail when hiring VAs and team members11:00 – Vision, values, and leadership in team-building13:06 – Personality types and why they matter when hiring16:30 – Process for identifying tasks to delegate19:53 – Creating SOPs, structure, and accountability22:44 – Setting expectations and managing chaos26:18 – Time audits and optimizing your calendar for productivity30:05 – Slow down, lead better, and build the right tea#BusinessGrowth #LeadershipDevelopment #ScalingWithVAs

Welcome to our latest episode! Today, Dave and Will dive into the transformative power of mindset retreats, real estate conferences, and networking at high-level masterminds. Both recently returned from separate but impactful events in Las Vegas—Dave from the Freedom Mastermind and Will from Keller Williams Family Reunion. They break down their biggest takeaways and why stepping out of your comfort zone to invest in personal and professional growth can lead to massive success.In this episode, Dave shares insights from the Freedom Mastermind, where he worked with top industry leaders to refine decision-making, expand awareness, and elevate business strategy. He explains why high-ticket masterminds are critical for business owners looking to break through income ceilings and accelerate success. Will discusses the state of the real estate market, key strategies for listing lead generation, and what it's like to learn directly from Gary Keller and other top-producing agents. They also highlight the importance of being in the right environment, surrounding yourself with high-achievers, and constantly seeking new ideas to improve and scale.Whether you're a real estate investor, entrepreneur, or business owner, this episode will challenge you to think bigger and take action toward your goals. Tune in now to learn how to leverage masterminds, networking, and personal development to achieve long-term success!TIMESTAMPS02:09 – Will and Dave's recent trip to Las Vegas06:03 – The power of in-person networking and learning from top producers08:34 – Speaking on real estate panels10:49 – Direct mail strategies and listing lead generation14:33 – Market insights and mindset shift for 202416:49 – Experience at the Freedom Mastermind19:22 – Why entrepreneurs invest in high-ticket masterminds22:07 – How decision-making impacts income and business success24:50 – Upgrading your environment for business growth27:40 – Takeaways: self-investment, business mindset, and mentorship#MindsetMatters #RealEstateGrowth #EntrepreneurLife #NetworkingForSuccess #BusinessMastermind

Welcome to our latest episode! Today, we're joined by Chris Petzy, Co-owner and CEO of Seacoast2Summit Vacation Rentals. Chris is a real estate investor, coach, Airbnb Superhost, and industry thought leader. With over five years in the short-term rental space and a decade of experience in streamlining business operations, Chris has built a reputation for leveraging modern-day technology and assembling high-performing teams. Through his expertise, he helps homeowners earn more while stressing less by optimizing their short-term rental investments.In this episode, we dive into the evolving world of short-term rental management and explore the growing need for self-management solutions. Chris and his co-founder at LaunchPad Consulting, Dave Menapace, discuss their innovative approach to empowering property owners with the tools, systems, and strategies needed to operate efficiently. They break down the essential steps to running a short-term rental, from automating operations and leveraging technology to hiring vendors and managing guests effectively. Whether you're an investor looking to offset taxes, a host seeking to maximize returns, or someone considering entering the space, this conversation is packed with insights to help you navigate the process smoothly.Tune in now to learn how to take control of your short-term rental business while minimizing stress and maximizing profits!TIMESTAMPS03:07 – Guest intro: Chris Petzy05:03 – From investing to short-term rental management08:06 – The gap in the STR market and the need for self-management solutions12:18 – Short-term rental operators' pain points17:02 – Why hospitality matters in real estate investing22:24 – LaunchPad Consulting helps homeowners streamline operations28:02 – The importance of automation and revenue management 34:29 – How to connect with Chris and LaunchPad ConsultingConnect with the Guest:Website: https://www.seacoastvacationrentals.co/Linkedin: https://www.linkedin.com/in/chrispetzy/Instagram: https://www.instagram.com/chris_petzy/Linktree: https://linktr.ee/chrispetzy#ShortTermRentals #RealEstateInvesting #PassiveIncome #SelfManagement #STRAutomation

Welcome to our latest episode! Today, we're diving into the proposed short-term rental (STR) ordinance in Newry, Maine, a market that has remained largely unregulated—until now. This draft regulation aims to introduce new safety and operational standards for vacation rentals, impacting everything from occupancy limits to fire safety, parking, and trash control. With the town seeking to balance the needs of residents, visitors, and property owners, this discussion is crucial for anyone invested in the future of STRs in the area.In this episode, we break down the key provisions of the proposed ordinance, highlighting what we like, potential challenges, and how these changes could affect STR operators. We discuss the emphasis on health and safety, including new requirements for fire extinguishers, smoke detectors, emergency contacts, and water quality testing. We also explore how these rules compare to other regulated markets and whether Newry's small-town infrastructure can realistically implement and enforce them. Plus, we share insights on how STR owners can prepare for potential changes and ensure compliance while maximizing their rental business.Tune in now to get a full breakdown of the proposed Newry STR ordinance and what it means for the future of short-term rentals in the area!TIMESTAMPS00:00 – Introduction to the episode01:02 – Market updates and new developments03:58 – Overview of the proposed STR ordinance in Newry, Maine06:26 – Key safety regulations: fire extinguishers, occupancy limits, and egress10:04 – Trash control plans and parking regulations13:16 – Water testing requirements and compliance challenges16:03 – The role of emergency contacts and management logistics19:47 – Floor plan requirements and operational concerns23:12 – The financial and tax implications of enforcement26:50 – Final thoughts and predictions for the future of STRs in Newry#STRRegulations #ShortTermRentals #VacationRentals #RealEstateInvesting #STRMarketUpdates

Welcome to our latest episode! Today, we're joined by Adrienne Green for an insightful discussion on systemizing real estate investing and achieving true time freedom. Adrienne is a seasoned investor and entrepreneur who transitioned from running a real estate team to building a location-independent lifestyle while managing a robust rental portfolio. Through strategic delegation, virtual assistants, and automation, she has created a business model that allows her to travel full-time while maintaining and growing her investments. In this episode, Adrienne shares her journey from building a real estate sales team to selling it and transitioning into full-time real estate investing. She dives into how she leverages virtual assistants to streamline operations, eliminate busywork, and scale efficiently. We discuss the importance of shifting from solopreneur to business owner, utilizing automation tools, and focusing on high-impact tasks. Adrienne also provides actionable insights on hiring and managing virtual assistants, creating efficient systems, and reclaiming time for strategic growth. Tune in now to learn how to implement these game-changing strategies and take your real estate business to the next level! TIMESTAMPS 03:40 – Guest intro: Adrienne Green 07:00 – Selling a real estate team for time freedom 12:10 – Automation, virtual assistants, and streamlining real estate investing 18:25 – Mindset shift from solopreneur to business owner 24:50 – Overcoming common challenges with delegation 30:30 – Tools and systems for automation 37:05 – Key takeaways on leveraging virtual assistants 42:20 – Final thoughts and Adrienne's vision for the future Connect with the Guest: Website: https://adriennegreen.com/ Linkedin: https://www.linkedin.com/in/adrienne-green-real-estate/ Instagram: https://www.instagram.com/arealgreen/?hl=en #RealEstateAutomation #VirtualAssistants #PassiveIncome #Delegation #FinancialFreedom

Welcome to our latest episode! Today, we're joined by Jonathan Levitt, Co-Founder and President of No Worry Home, for an insightful discussion about proactive home maintenance. Jonathan, a former attorney and co-founder of Outside GC, has a rich background in entrepreneurship and professional services. Leveraging his expertise, Jonathan created No Worry Home, a service dedicated to providing preventive maintenance and total home care. His innovative approach ensures homeowners and short-term rental operators maintain safe, fully operational properties year-round. In this episode, Jonathan shares the journey behind No Worry Home, highlighting how his career in law and entrepreneurship inspired him to address a critical gap in home maintenance. We discuss the importance of proactive upkeep for short-term rentals, emphasizing the cost savings and peace of mind it offers. Jonathan outlines how his service addresses common issues such as HVAC maintenance, appliance care, and seasonal preparedness. He also dives into the value of building trust with homeowners through comprehensive reports, reliable handyman services, and a focus on safety. This conversation is packed with insights for STR owners looking to protect their investments and deliver exceptional guest experiences. Tune in now to explore how preventive maintenance can elevate your STR game and keep your properties in top shape! TIMESTAMPS 03:40 – Guest intro: Jonathan Levitt 06:50 – The inspiration behind No Worry Home 13:20 – How preventive maintenance prevents costly issues 19:10 – Addressing challenges with property safety 25:45 – Building trust with homeowners and referrals 30:50 – Expanding No Worry Home's services 36:15 – Key takeaways for STR operators 39:10 – Final thoughts and future plans Connect with the Guest: Website: https://noworryhome.com/ Linkedin: https://www.linkedin.com/in/jonlevitt/ #HomeMaintenance #STRSuccess #PreventiveCare #VacationRentals #ProactiveManagement

Welcome to our latest episode! Today, we're joined by Lucas Piper, the owner and founder of Five Star Vacation Home Rentals, for an in-depth conversation about his journey in the short-term rental (STR) industry. Lucas's path began with transforming his own home into a vacation rental, which evolved into a thriving career combining his passions for travel, hospitality, and helping others. With a background in social work and a wealth of life experience, including time spent volunteering in Guatemala, Lucas has built a business that focuses on delivering 5-star experiences for guests while mentoring investors and homeowners to achieve financial freedom. In this episode, Lucas shares how he transitioned from a career in social work to real estate, leveraging his experiences to build a unique STR brand in the competitive Austin market. He discusses his journey of starting with house hacking and Arbitrage properties, overcoming challenges in partnerships, and scaling his business with integrity and a guest-centric approach. Lucas emphasizes the importance of community, values-driven decision-making, and maintaining a strong brand in achieving success. Tune in now to discover Lucas's story and gain valuable insights into building a thriving STR business while fostering meaningful connections within the industry! TIMESTAMPS 03:10 - Guest Intro: Lucas Piper 06:45 - From house hacking to STRs 13:20 - Masterminds and finding mentorship 19:00 - Overcoming challenges with Arbitrage properties 27:15 - Transitioning full-time into STR management 36:40 - The importance of values-driven decision-making 43:20 - Building the Five Star Vacation Home Rentals brand 48:10 - Community-building efforts and mentoring 50:10 - Final thoughts and Lucas's vision for the future Connect with the Guest: Website: https://www.fivestarvhr.com/ Linkedin: https://www.linkedin.com/in/lucas-piper-10777056/ #ShortTermRentals #PassiveIncome #STRInvesting #VacationRentals #FinancialFreedom

Welcome to our latest episode! Today, we're thrilled to have Bernie Cesareo, a seasoned short-term rental (STR) entrepreneur and founder of Eagle Stays, join us for an insightful discussion. Bernie is not only a dedicated Airbnb Superhost but also a co-host and specialized bookkeeper for other Superhosts. With a unique real estate journey spanning decades, Bernie transitioned from long-term rentals to STRs, building a portfolio of properties that prioritize guest experiences and passive income. His hands-on approach and innovative strategies have enabled him to scale his business while maintaining a focus on time freedom and quality of life. In this episode, Bernie shares his journey from managing long-term rentals to transforming properties into STR successes. He discusses his approach to leveraging IRA investments, scaling efficiently with virtual assistants, and prioritizing large homes for maximum ROI. Bernie also dives into his unique co-investment model, explaining how he collaborates with investors to achieve shared success. If you're curious about building passive income, maximizing tax benefits, or scaling an STR business, this episode is packed with actionable insights and strategies. Tune in now to hear Bernie's story and discover how you can take your STR business to the next level by focusing on efficiency, guest experience, and creative investment strategies! TIMESTAMPS 01:00 – Guest intro: Bernie Cesareo 02:15 – From Malta to Long Island 05:40 – House hacking in 1990 09:20 – Transitioning to remote property management in the 1990s 16:00 – Leveraging the BRRRR strategy before it was popular 20:30 – Exploring rent-to-own strategies and their long-term benefits 24:00 – Introduction to short-term rentals in suburban Cleveland 28:35 – Managing STRs while working full-time 32:00 – Scaling and focusing on efficiency 36:10 – Utilizing IRA investments for multifamily deals 40:20 – Partnering with investors for STR acquisitions 45:00 – Strategies for balancing time freedom and profitability 48:00 – Final thoughts and Bernie's goals for the future Connect with the Guest: Website: https://eaglestays.com/ Linkedin: https://www.linkedin.com/in/bernie-cesareo-6979647/ #ShortTermRentals #PassiveIncome #STRInvesting

Welcome to our latest episode, where Dave and Will take a deep dive into the challenges and triumphs of the 2024 real estate market while sharing insights into what lies ahead for 2025. Drawing from their experiences in real estate, STR property management, and consulting, they break down shifting buyer profiles, market timing strategies, and the importance of having the right team. In this episode, Dave and Will explore the complexities of navigating a historically low-transaction market, highlighting the role of seller credits, buyer motivation, and evolving property preferences. They discuss how timing the market in regions like New England can impact success, and why having a cohesive lending and management team is critical. From mastering revenue management to adopting new amenities like hot tubs and saunas, the duo offers actionable advice to help investors stay competitive. If you're looking to enhance your strategies and thrive in the real estate and STR space, this episode is packed with expert insights and practical takeaways. Tune in now to learn how to prepare for 2025, adapt to market changes, and optimize your investments for long-term success! TIMESTAMPS 01:00 – Introduction and life updates 03:09 – 2024 market recap: challenges and shifting buyer profiles 05:24 – Seller credits and pricing strategies 07:56 – Market timing strategies in New England 11:09 – Seller motivation in sales success 15:16 – Dave's live-in BRRRR strategy 18:40 – Preparing during escrow is key to STR success 22:30 – The power of early adoption for STR amenities 26:28 – The "Smoky Mountain effect" 32:43 – 2025 predictions: safety, standardization, and evolving guest needs 36:02 – 2025 goals: portfolio growth, consulting expansion, and development plans #RealEstateTrends2025 #STRInvesting #PropertyManagementTips

Welcome to our latest episode, where Dave and Will are joined by Jess Lea, Director of Operations at The 5 Star Co-Host, to discuss the nuances of maintaining short-term rental properties effectively. With her extensive experience in managing operations and consulting, Jess offers invaluable insights into categorizing maintenance issues, optimizing team responses, and streamlining operations to enhance guest experiences while reducing costs. In this episode, Jess delves into how to identify and prioritize maintenance needs based on urgency and guest impact, providing actionable advice for both self-managing hosts and professional co-hosts. She shares her strategies for creating efficient systems to track, respond to, and resolve issues without unnecessary expenses or disruptions. Dave and Will add their perspectives on leveraging these systems to manage properties at scale while maintaining high guest satisfaction. Whether you're managing one property or an entire portfolio, this episode offers a practical guide to staying proactive and delivering hassle-free rental experiences. Tune in now to learn how to refine your property management processes, empower your team, and ensure your guests have memorable stays, every time! TIMESTAMPS 01:00 – Life and business updates 05:00 – Guest intro: Jess Lea 06:30 – Scaling property management operations with effective systems 10:00 – Categorizing maintenance issues: Low, high, and urgent 13:45 – Tracking maintenance and optimizing team workflows 18:00 – Balancing guest satisfaction with operational efficiency 22:30 – Insights for scaling hassle-free operations Connect with the Guest: Website: https://5strcohost.com/ Linkedin: https://www.linkedin.com/in/jesslea/ Instagram: https://www.instagram.com/its_jesslea/ #STRMaintenance #PropertyManagementTips #HassleFreeRentals --- Support this podcast: https://podcasters.spotify.com/pod/show/hasslefreere/support

Welcome to our latest episode where Dave and Will discuss the unique dynamics of winter short-term rental markets and how to prepare for the upcoming season. Drawing on their expertise in STR property management, consulting, and real estate, they explore strategies for success in snowy destinations and share exciting updates, including Dave's new venture into midterm rentals. In this episode, Dave and Will dive into essential tips for winter STR management, from securing reliable snow removal services to equipping properties with the right amenities like hot tubs and fireplaces. They also explore the evolving buyer profiles in today's market and discuss the advantages of slopeside condos for investors seeking a hassle-free experience. As winter bookings ramp up, the hosts provide actionable advice on pricing strategies, supply stocking, and marketing adjustments to capitalize on the season. Whether you're new to the STR world or looking to optimize your existing property, this episode is packed with valuable insights to help you thrive in winter markets. Tune in now to learn how to streamline your STR operations, make the most of seasonal opportunities, and set yourself up for success in 2024 and beyond! TIMESTAMPS 01:00 – Life and business updates 03:20 – Expanding into midterm rentals in Metro West, Massachusetts 06:30 – Seasonal STR dynamics: holiday bookings and beyond 09:00 – Evolving buyer profiles and trends in STR investments 13:00 – Tips for managing snow removal and winter maintenance 15:45 – The benefits of slopeside condos for investors 18:20 – Essential winter amenities: hot tubs, generators, and supplies 22:00 – Pricing and marketing strategies for the winter season 25:00 – Preparing properties for peak winter demand #WinterSTRTips #ShortTermRentals #STRInvesting --- Support this podcast: https://podcasters.spotify.com/pod/show/hasslefreere/support

Welcome to our latest episode where Dave and Will explore the thriving short-term rental market of Old Orchard Beach, Maine. Drawing from Dave's extensive experience in property management and consulting, and Will's expertise as New England's top STR-focused real estate agent, they provide actionable strategies for navigating this timeless destination. In this episode, Dave and Will dive into the unique dynamics of Old Orchard Beach, discussing its accessibility, enduring appeal, and diverse property options. From affordable condos to luxury oceanfront homes, they outline the market's key segments and highlight the critical factors that ensure thriving investments. Learn how to optimize your rental with thoughtful amenities, smart design, and by targeting the right guest avatar. Additionally, they share essential tips on navigating potential HOA restrictions, minimizing expenses, and maximizing cash-on-cash returns in one of New England's most reliable short-term rental markets. Tune in now to discover why Old Orchard Beach is a lucrative market for short-term rental investments and gain practical advice for creating properties that attract repeat guests year after year! TIMESTAMPS 01:00 – Old Orchard Beach as a vacation market 02:00 – Location and accessibility drive consistent demand 04:00 – Different types of STR properties 05:30 – Key considerations for investing in condos 08:00 – Starter single-family homes and their amenities 12:00 – Appeal of large family homes and oceanfront properties 15:00 – Understanding the market's high returns and low expenses 16:30 – Why Old Orchard Beach remains a timeless destination #ShortTermRentalTips #OldOrchardBeachSTR #STRInvesting --- Support this podcast: https://podcasters.spotify.com/pod/show/hasslefreere/support

Welcome to our latest episode where Dave and Will delve into the strategies and insights that make Sunday River one of the most desirable short-term rental markets in New England. With Dave's expertise in property management and consulting and Will's extensive experience in real estate, this dynamic duo provides a comprehensive guide to thriving in this unique year-round destination. In this episode, Dave and Will explore the core elements of success for short-term rental investors in the Sunday River area. From location and design to amenities and market saturation, they discuss everything you need to consider before purchasing or managing a property in this competitive market. They share actionable advice on optimizing your property's guest experience with must-have features like hot tubs, saunas, and spacious sleeping arrangements. You'll also learn about the seasonal dynamics of the market, budgeting for high expenses, and why this affordable yet lucrative area is a prime spot for real estate investment. Tune in now to gain exclusive insights and practical tips for navigating the Sunday River rental market. Whether you're a seasoned investor or considering your first mountain property, this episode is packed with valuable information to help you succeed! TIMESTAMPS 01:00 - Sunday River as a rental market 02:00 - Sunday River is an ideal year-round short-term rental destination 03:30 - Key location considerations 05:10 - Must-have amenities: hot tubs, saunas, and fire pits 07:30 - The rise of modern design and creating hotel-like experiences 09:45 - Understanding market saturation 12:00 - Expense considerations: snow removal, utilities, and maintenance 14:00 - Why summer can be just as profitable 15:00 - Key takeaways for investing in Sunday River properties #AirbnbInvesting #SundayRiverProperties #ShortTermRentals --- Support this podcast: https://podcasters.spotify.com/pod/show/hasslefreere/support

Welcome to our latest episode featuring Jordan Harboldt, Assistant Sales Manager at Mainely Tubs and a 20-year veteran in the pool and spa industry. Jordan shares his extensive experience helping property owners enhance guest experiences with high-quality hot tubs, saunas, and swim spas. From selecting durable, energy-efficient hot tubs to the wellness benefits of saunas and versatility of swim spas, Jordan covers everything you need to know about adding these sought-after amenities to your short-term rental. In this insightful discussion, Jordan dives into the crucial factors of purchasing and maintaining hot tubs designed for rental properties, offering tips on choosing the right model, avoiding common pitfalls, and maximizing the lifespan of your investment. He explains why hot tubs from big-box stores may not meet the durability needs of short-term rentals and highlights the benefits of Mainely Tubs' service-first approach. Jordan also explores the rise of saunas as a popular wellness feature, touching on how to pick a sauna built for cold climates and high occupancy. For those looking to offer a unique luxury experience, Jordan introduces swim spas as a dual-purpose alternative to traditional pools and hot tubs, ideal for year-round rentals. Tune in now to gain valuable insights from Jordan on how to select the best amenities for your rental property, create unforgettable guest experiences, and safeguard your investment with the right product choices and support. This episode is packed with expert tips for rental property owners looking to stand out in today's competitive market! TIMESTAMPS 01:00 - Guest intro: Jordan Harboldt, Mainely Tubs 02:15 - The value of high-quality hot tubs for short-term rentals 03:30 - How to choose the right hot tub for rental properties 05:00 - Common mistakes in choosing a hot tub and how to avoid them 07:30 - Financing options for property owners and their benefits 09:45 - The rise of saunas as a wellness feature in rentals 13:10 - Key quality considerations for selecting a sauna 15:50 - Why cheap saunas may not be ideal for cold climates 18:20 - Introducing swim spas as an alternative to pools 22:15 - Advantages of swim spas for year-round rental properties 25:00 - Maintenance and support: why it matters for rentals 28:40 - Summary of key considerations for hot tubs, saunas, and swim spas Connect with the Guest: Website: https://mainelytubs.com/ Linkedin: https://www.linkedin.com/in/jordan-harboldt-02476413a/ #ShortTermRentals #HotTubEssentials #SaunaBenefits #WellnessRentals #SwimSpa --- Support this podcast: https://podcasters.spotify.com/pod/show/hasslefreere/support

In this episode of Hassle-Free RE, hosts Dave Menapace and Will Van Wickler dive into the world of real estate investment, focusing on the nuances of flipping properties versus undertaking new construction projects. They bring real-life insights on how each path presents unique challenges, potential pitfalls, and opportunities for success. Dave and Will discuss their own experiences, including lessons learned about budgeting, unexpected costs, and maintaining control over project variables—especially in markets like New England. Will shares his journey from observing and collaborating with industry experts to managing his own successful new construction ventures. He details the advantages of new construction, such as predictability, flexibility with customization, and the potential for a stronger market appeal. For listeners interested in real estate investing, Dave and Will offer advice on financing options, forming partnerships, and building a strong network, emphasizing the importance of understanding market needs and establishing a focused strategy. Tune in now to gain valuable insights on navigating the complexities of real estate investments, whether through flipping or new construction! TIMESTAMPS 00:00 - Welcome and Introduction 05:03 - Differences Between Flipping and New Construction 07:31 - Challenges and Unexpected Costs in Flipping 08:14 - Benefits of New Construction and Control Over Variables 15:46 - Finding Deals and Building Relationships with Lenders 23:33 - Creative Financing for Property in Norway Lake 30:24 - Will's Goals for 2025 and New Projects 32:07 - Upcoming Events and Educational Courses for Investors 35:20 - Closing Remarks and Wrap-Up #RealEstateInvesting #NewConstruction #FlippingProperties #PropertyInvestment #InvestmentStrategies --- Support this podcast: https://podcasters.spotify.com/pod/show/hasslefreere/support

In this episode of Hassle-Free RE, Dave Menapace and Will Van Wickler tackle two important topics: managing guest reviews on platforms like Airbnb and VRBO, and finding the perfect time and strategies for buying a short-term rental (STR) property. Whether you're an experienced STR host or new to the business, understanding the nuances of guest reviews and the optimal buying times can significantly impact your success. They begin by exploring the evolving landscape of reviews, with Dave sharing insights into how they used to be easily removable and what has changed in recent months. The discussion dives into best practices for addressing and mitigating negative reviews, including proactive communication strategies and ways to maintain a five-star guest experience, regardless of the challenges that arise. In the second half, Dave and Will discuss why Q3 and Q4 are often ideal for buying STR properties, especially in markets like New England. They share insights on key investment markets, finding off-market deals, and why patience is crucial for locking in favorable deals. Dave and Will also stress the importance of investing in education and consulting to maximize property performance and ensure long-term profitability. Tune in now to gain valuable insights on handling reviews and timing your STR investment for optimal success! TIMESTAMPS 0:00 - Welcome and introduction from Cape Cod 1:00 - STR performance updates in Cape Cod and South Shore 7:17 - Changing landscape of STR reviews on Airbnb and VRBO 10:35 - Strategies for addressing review challenges and guest expectations 14:56 - Introducing the “Save the Review” process for better guest feedback 19:51 - Proactive communication to resolve guest issues effectively 23:43 - Best times for buying STR properties and market timing 27:54 - Finding off-market deals in New England's key STR markets 31:39 - High-potential investment areas and analyzing property values in MA 38:26 - Benefits of investing in STR education and consulting for success #GuestReviewManagement #ShortTermRentalTips #PropertyInvestment  --- Support this podcast: https://podcasters.spotify.com/pod/show/hasslefreere/support

In this episode of Hassle-Free RE, Dave Menapace and Will Van Wickler dive into the key elements of creating the perfect offer when buying a home. Whether you're a seasoned real estate investor or a first-time buyer, understanding how to craft an offer that stands out can be the difference between securing your dream property or losing out to another buyer. Dave and Will share insights from their combined experiences of over $100 million in transactions, breaking down what makes an offer competitive while keeping it simple and effective. The discussion covers everything from understanding key terms in the offer, building rapport with the seller, to strategically using earnest money and inspection contingencies to strengthen your position. They also explore the importance of working with a responsive lender, the benefits of flexible closing dates, and how to approach offers on properties with short-term rental potential. Tune in now to discover the strategies you need to create a winning offer and get ahead in a competitive market! TIMESTAMPS 01:00 - STR performance in peak season 04:25 - Crafting the perfect offer when buying a home. 05:59 - Mistakes new investors make when submitting offers 07:34 - Understanding what the seller values most 12:11 - How earnest money deposits show you're serious and help strengthen your offer. 16:19 - Why inspection contingencies matter 20:01 - Walk-and-talk inspections: A strategy for making your offer cleaner 23:03 - How down payment flexibility can improve your offer's appeal. 27:06 - Multiple pre-approvals and adjusting your offer during the process. 30:22 - Closing dates and personal property negotiations. 33:05 - Making offers that sellers can't refuse, and ensuring the deal makes sense for both sides. #RealEstateOffers #HomeBuyingStrategies #PropertyInvesting --- Support this podcast: https://podcasters.spotify.com/pod/show/hasslefreere/support

Welcome to our latest episode featuring Kenneth 'Kenny' Bedwell, Founder and CEO of STR Insights, and host of the Cash Flow Positive Podcast. In this episode, Kenny dives into the world of short-term rental data and shares his journey from purchasing his first STR to founding STR Insights, a data-driven tool designed to help investors identify profitable markets. With 6 STRs across New York, Kenny has a wealth of knowledge on how to strategically grow a rental portfolio using smart market research and the power of data. In this episode, Kenny shares how to break away from relying on OTAs like Airbnb and VRBO by using direct marketing strategies. He emphasizes the importance of building a long-term, self-sustaining rental business by finding hidden STR markets, creating standout properties, and enhancing them with unique, guest-focused amenities. The episode explores effective ways to identify profitable markets and introduces Kenny's concept of "Darkhorse amenities," which help properties stand out in competitive markets. Tune in now to discover how you can leverage data and unique amenities to transform your short-term rental investment strategy. This episode is packed with actionable advice for anyone looking to scale their STR business while breaking away from the constraints of OTAs. TIMESTAMPS 01:05 – Guest intro: Kenneth Bedwell, founder of STR Insights 03:00 – From CitiBank to STR investor and founding STR Insights 07:10 – The challenges of finding the best STR markets 09:25 – Why hyper-local STR markets often go unnoticed 12:15 – Exploring "guest booking fatigue" and making properties stand out 17:35 – Using data to find high-revenue properties in unknown markets 23:50 – Kenny's “Darkhorse amenities” concept and how unique amenities boost revenue 33:40 – How properties can outperform competitors with the right amenities 38:10 – Lessons from STR Insights data and market analysis 43:30 – Final thoughts and how to get started with STR Insights Connect with the Guest: Website: https://www.strinsights.com/ Linkedin: https://www.linkedin.com/in/kenneth-bedwell-9680a8113/ Instagram: https://www.instagram.com/kenny_bedwell/ Linktree: https://linktr.ee/kennybedwell #STRInvesting #DataDrivenInvesting #ShortTermRentals #CashFlowPositive #STRSuccess --- Support this podcast: https://podcasters.spotify.com/pod/show/hasslefreere/support

Welcome to Hassle-Free RE! In this episode, Dave Menapace and Will Van Wickler tackle a crucial topic for short-term rental hosts: breaking away from reliance on OTAs (Online Travel Agencies) like Airbnb and VRBO. They dive into effective strategies for transitioning guests to direct bookings, helping hosts build stronger, more profitable relationships with their guests. Dave and Will share both simple and tech-driven methods for capturing guest contact information, including tools like StayFi for gathering emails from all visitors. They also explore creative ways to use social media and Google Business pages to increase visibility and attract repeat bookings. By focusing on automation, thoughtful marketing, and delivering value, they outline a clear path to reducing OTA fees and boosting profits. If you're looking to grow your short-term rental business by creating a loyal customer base and taking control of your bookings, tune in now for actionable tips on how to successfully break away from OTAs. TIMESTAMPS 01:00 – How to transition guests from OTAs to direct bookings 02:01 – Simple ways to collect guest information 04:50 – Using StayFi to gather emails from all guests 07:00 – Leveraging Instagram and Facebook to build your brand 10:45 – Setting up a Google Business page for your property 12:02 – Direct booking websites: best practices 16:01 – Offering discounts and incentives for direct bookings 18:00 – Closing thoughts and sponsorship opportunities #DirectBookings #VacationRentals #ShortTermRentals --- Support this podcast: https://podcasters.spotify.com/pod/show/hasslefreere/support

Welcome to our latest episode! Today, we're thrilled to have Sam Mistretta, a seasoned short-term rental (STR) entrepreneur and president of GSTR, join us for a value-packed discussion. Sam has built an impressive portfolio of STR properties and has launched GSTR Marketing to help hosts increase their direct bookings. Sam's journey began in the IT industry, but after reading Rich Dad, Poor Dad, he transitioned into real estate, starting with duplexes and eventually moving into the short-term rental space. Now, Sam is known for his expertise in scaling STR businesses and helping others do the same with innovative marketing strategies. In this episode, Sam shares how he grew his co-hosting business across multiple markets, including Baton Rouge, Galveston, and Gulf Shores. He offers insights on the challenges and rewards of running a co-hosting business, the importance of leadership and team-building, and how to effectively market to past guests using GSTR Marketing. If you're a host looking to scale your STR business or interested in increasing direct bookings, this episode is full of actionable advice and strategies. Tune in now to discover Sam's journey from corporate life to full-time STR success and learn how you can improve your guest retention with targeted email and text campaigns! TIMESTAMPS 01:00 – Introduction Sam Mistretta 02:10 – From IT to real estate 03:35 – Starting with duplexes and scaling to STRs 09:02 – Transition from long-term rentals to short-term rentals 13:54 – Scaling the co-hosting business and marketing strategies 18:30 – Leaving the corporate world for full-time STR management 27:10 – Leadership lessons and building the right team 32:41 – Go STR: Direct booking marketing for STRs 36:28 – How Go STR increases direct bookings 44:00 – Markets where Sam's co-hosting business operates 47:02 – Final thoughts on the importance of guest retention and direct bookings Connect with the Guest: Website: https://www.gostrmarketing.com/ Linkedin: https://www.linkedin.com/in/samuel-mistretta-0162b71b/ Instagram: https://www.instagram.com/samuelmistrpm/ Youtube: https://www.youtube.com/@GoSTRmarketing/featured #ShortTermRentals #STRGrowth  #DirectBooking #STRMarketing  --- Support this podcast: https://podcasters.spotify.com/pod/show/hasslefreere/support

Welcome to Hassle-Free RE, where we simplify the world of short-term rentals (STR) and empower property owners to provide the best experience possible—while keeping safety top of mind. In this episode, your hosts Dave Menapace and Will Van Wickler dive into one of the most overlooked aspects of running a successful STR business: safety. From protecting your property to ensuring the well-being of your guests, this episode will equip you with the practical knowledge and tools you need to create a secure environment without sacrificing comfort or profitability. With guest safety consultant and expert Justin Ford's insights, Dave and Will unpack real-world examples, discuss common safety blind spots, and walk you through the must-do safety measures for any STR. Whether you're a seasoned property manager or a new Airbnb host, you'll learn about everything from fire hazards to ensuring your pool, furniture, and grills are guest-friendly and liability-proof. Dave and Will also share practical tips for seasonal property safety inspections and offer access to a detailed 12-page safety checklist used by industry experts. Plus, there's a pro tip on how listing “safe” in your Airbnb description can boost your bookings! If you're serious about running a hassle-free, profitable STR, this episode is packed with actionable advice you won't want to miss. Stay safe, maximize your earnings, and give your guests peace of mind with these essential tips. Timestamps: 00:00 – Introduction: Why STR Safety is Important 03:00 – Fire Safety & Fire Extinguishers: A Must for All STRs 06:45 – Exterior Safety: Walkways, Driveways & Lighting 10:15 – Grill & Barbecue Safety: Avoiding Fires 14:00 – Pool & Hot Tub Safety: Ensuring Fun Without Risk 18:30 – Furniture Safety: Why Inspections Matter 22:10 – Interior Safety: Fire Pits, Bunk Beds, and Portable Heaters 27:00 – Laundry Room Safety: Preventing Dryer Fires 30:30 – Final Thoughts: How Safety Can Boost Your Bookings & Protect Your Guests --- Support this podcast: https://podcasters.spotify.com/pod/show/hasslefreere/support

Welcome to Hassle-Free RE! In this episode, Dave Menapace and Will Van Wickler dive into an important aspect of short-term rental (STR) management: neighbor relations and technology solutions for preventing problems before they arise. With increasing scrutiny from neighbors and community groups, Dave and Will share best practices for managing properties responsibly and maintaining good relationships with neighbors while running a successful STR. They also explore essential technologies like cameras, smart locks, and noise decibel readers, and discuss how these tools help STR operators avoid issues, prevent property damage, and ensure compliance with local rules. If you're looking for practical tips on using tech to run your STR efficiently and minimize neighbor complaints, this episode has all the insights you need! Tune in now to discover how proactive management and the right tech stack can make all the difference in ensuring your STR operates smoothly while keeping the peace in your community. TIMESTAMPS 01:00 – Introduction 02:55 – Should I use a direct booking site to increase revenue? 04:00 – Why OTAs (Airbnb, VRBO) are still the best option for traffic 05:30 – Building trust with guests through direct booking marketing 07:35 – Neighbors, compliance, and STR tech stack 08:55 – Tech stack essentials: The best smart locks for STRs 10:00 – Why Ring cameras work best for monitoring properties 14:10 – The role of tech in protecting your assets 16:05 – Strategy for proactively communicating with neighbors 18:40 – Why staying professional and neutral in public forums is critical 20:10 – The importance of checking security cameras daily 21:00 – Conclusion and how to connect with Dave and Will #ShortTermRentals #STRTechStack #RealEstateInvesting #PropertyManagement #VacationRentals --- Support this podcast: https://podcasters.spotify.com/pod/show/hasslefreere/support

Welcome to Hassle-Free RE! In this episode, Dave Menapace and Will Van Wickler take a deep dive into what it means to be a leading short-term rental (STR) real estate agent. They share their journeys, discuss the critical skills and knowledge necessary to excel in this niche, and explain how to set yourself apart in a competitive market. In this episode, Dave and Will break down the value of creating a strong network of vendors, the importance of knowing your market in and out, and how to develop a reputation as a consultant who offers more than just a transaction. They also emphasize the value of personal experience, sharing how owning and managing STRs themselves gives them an edge in understanding the market. Whether you're a real estate agent looking to specialize in STRs, a buyer wanting to find the perfect vacation home, or simply interested in the ins and outs of the STR industry, this episode is packed with actionable tips. Tune in now to discover how you can leverage specialized knowledge and strategies to thrive in the short-term rental space. TIMESTAMPS 01:00 – Introduction 02:12 – What makes a leading STR real estate agent? 04:01 – Will shares how he got into the STR real estate niche 06:31 – Essential skills and knowledge for STR real estate agents 09:44 – The importance of being a fiduciary and offering consulting over just transactions 13:20 – How to create a value proposition and become a consultant 14:58 – The value of building a trusted vendor network 17:08 – Understanding local market trends and regulations 19:02 – How STR agents can create long-term relationships with clients 21:00 – Dave discusses his favorite emerging STR markets 23:05 – Wrapping up and how to connect with Dave and Will for more guidance #ShortTermRentals #RealEstateAgent #STRSuccess #RealEstateInvesting --- Support this podcast: https://podcasters.spotify.com/pod/show/hasslefreere/support

Welcome to Hassle-Free RE! In this episode, Dave Menapace and Will Van Wickler provide an in-depth market analysis on Old Orchard Beach, one of Maine's oldest vacation rental destinations. Whether you're an experienced investor or new to the game, this episode offers crucial insights into what makes this market a lucrative opportunity. Dave and Will explore the unique characteristics of Old Orchard Beach, touching on the advantages of investing in a market with a deep rental history. They break down property types, key amenities that boost ROI, and the importance of thoughtful design, smart marketing, and understanding the market's seasonal demands. From beachfront homes to tier two properties a few minutes from the water, this episode is packed with valuable tips for anyone looking to maximize returns in this emerging market. If you're ready to unlock success in Old Orchard Beach, tune in now to discover expert strategies, market trends, and the hidden potential waiting to be tapped in this prime coastal location. TIMESTAMPS 01:01 – Market deep dive on Old Orchard Beach 02:05 – Old Orchard Beach's history as a vacation destination 04:53 – Importance of Canadian tourists in Old Orchard Beach 09:50 – General market data overview: home values, occupancy, and ROI 13:43 – Tier 2 properties and how to maximize returns 22:22 – Old Orchard Beach as a central hub for exploring Maine 24:10 – Deep dive into property types: condos vs. single-family homes 29:00 – Amenities that make a difference: hot tubs, mini-splits, fire pits 32:03 – The power of thoughtful marketing and professional photos 35:28 – Overview of top-performing properties in Old Orchard Beach 37:00 – How to connect with Dave and Will for more guidance #ShortTermRentals #RealEstateInvesting #BeachRentals #OldOrchardBeach  --- Support this podcast: https://podcasters.spotify.com/pod/show/hasslefreere/support

Welcome to Hassle-Free RE. In this episode, Dave Menapace and Will Van Wickler dive deep into the strategies for successfully selling your short-term rental property. Whether you're self-managing or working with a property manager, this episode is packed with essential tips to help you maximize the value of your STR when it's time to sell. Dave and Will discuss the critical importance of planning with the end in mind, including setting up separate Airbnb and VRBO accounts for your property, understanding the non-transferability of bookings, and managing guest expectations during a sale. They also cover the nuances of working with lenders, the potential pitfalls in STR transactions, and how to set up your property for a smooth, profitable sale. If you're considering selling your STR, this episode is a must-listen for actionable insights and expert advice. Tune in now to learn how to position your property for success, attract the right buyers, and ensure a seamless transition that protects your investment and maximizes your returns! TIMESTAMPS 01:01 - Introduction and mindset tips for STR owners 03:42 - Importance of planning with the end in mind when selling an STR 05:45 - The pitfalls of non-transferable Airbnb and VRBO bookings 07:00 - Setting up separate accounts for future sales 10:02 - Managing guest expectations and maintaining booking value 12:58 - Working with property managers and ensuring smooth transitions 15:23 - The role of lenders and understanding DSCR loans 18:46 - Storytelling: Real-life examples of STR sales gone wrong 24:05 - Final thoughts on maximizing your STR sale 27:30 - How to connect with Dave and Will for more advice #ShortTermRentalsSale #RealEstateInvesting #PropertyManagement #RealEstateTips --- Support this podcast: https://podcasters.spotify.com/pod/show/hasslefreere/support

Welcome to Hassle-Free RE. Dave Menapace and Will Van Wickler dive into the essential topic of cleaning in the short-term rental industry. With their combined experience in managing thousands of stays, they share insights on how to handle cleaning challenges effectively, maintain high standards, and build strong relationships with your cleaning team. In this episode, Dave and Will discuss the importance of having a reliable, high-quality cleaning team and the common challenges property owners face. They emphasize the need for setting realistic expectations, treating cleaners as vital partners, and the benefits of switching to an hourly cleaning rate to manage costs better. They also provide practical tips on collaborating with your cleaners to create a seamless experience for guests, highlighting how crucial this aspect is to the overall success of your rental business. If you're looking to master the art of short-term rental cleaning and ensure your properties are always guest-ready, this episode is for you. Tune in now to learn strategies that can help you maintain top-notch cleanliness while keeping your operations hassle-free! TIMESTAMPS 01:01 - Introduction and updates from Dave and Will 03:32 - The challenges and importance of cleaning in STRs 04:23 - The balance between quality, dependability, and price in cleaning services 06:23 - Building strong relationships with your cleaning team 07:12 - Common cleaning challenges and how to overcome them 09:50 - The role of checklists and setting cleaning standards 13:01 - Managing cleaning costs and the benefits of an hourly rate 17:15 - Additional strategies to ensure cleanliness and guest satisfaction 19:58 - Closing thoughts and how to connect with Dave and Will #shorttermrentals #RentalCleaning #PropertyManagement #RealEstateInvesting --- Support this podcast: https://podcasters.spotify.com/pod/show/hasslefreere/support

In this episode of Hassle-Free RE, Dave Menapace and Will Van Wickler share their expert advice on the crucial topic of preventative maintenance for short-term rental properties. They dive into practical strategies for keeping your STR properties in top condition, both inside and out, especially during the shoulder seasons. Whether you're managing properties yourself or overseeing a team, these tips will help you stay ahead of potential issues and ensure a seamless guest experience. The discussion kicks off with a focus on the exterior of your property, covering essentials like septic pumping, generator servicing, and gutter maintenance. Dave and Will also touch on less obvious but equally important tasks like inspecting your driveway, checking the condition of outdoor amenities, and ensuring the house number is clearly visible for guests. As they move indoors, the importance of regular HVAC servicing, gas fireplace maintenance, and replacing batteries in smoke detectors and CO detectors is emphasized. They discuss common but critical tasks like checking furniture stability, updating first aid kits, and snaking drains to prevent clogs. By tackling these maintenance tasks proactively, you can avoid costly emergency repairs and keep your rental property running smoothly year-round. TIMESTAMPS 01:01 - Dave and Will discuss the importance of preventative maintenance for STR properties 04:00 - Exterior maintenance tips: septic pumping, generator servicing, and more 08:00 - The importance of driveway maintenance and curb appeal 09:56 - Interior maintenance tips: HVAC servicing, gas fireplace checks, and more 12:22 - Replacing batteries in smoke and CO detectors 14:00 - The significance of regular deep cleaning and checking all amenities 17:37 - Tips on snaking drains and checking furniture stability 19:16 - Using a Google Calendar for maintenance tracking 20:35 - Recap and final thoughts on maintaining your STR property #STRMaintenance #PropertyManagement #RentalProperty --- Support this podcast: https://podcasters.spotify.com/pod/show/hasslefreere/support

Welcome to our latest episode featuring Emanuele Pani, co-host of the STR Secrets podcast and a seasoned entrepreneur in the short-term rental industry. Emanuel, affectionately known as "E," has been a pivotal figure in the industry, influencing many through his unique insights on mindset and growth. This is E's second appearance on our show, with his first being in Episode 27, where he shared invaluable advice on short-term rental success. In this episode, E returns to discuss the crucial mindset shifts necessary for success in the short-term rental business. In this engaging conversation, E dives into the challenges that new hosts face when transitioning from their W2 jobs to full-time entrepreneurship. He explores the importance of upgrading your mindset, overcoming fears, and understanding the role of the environment in personal and professional growth. E shares his personal journey, including how changes in his life have shaped his approach to business and mindset. He offers actionable advice on how to navigate the complexities of balancing a W2 job with growing a rental business, and how to confidently step into a new phase of life and career. Tune in now to gain invaluable insights from Emanuele Pani on how to harness the power of mindset and environment to propel your short-term rental business to new heights. This episode is packed with wisdom for both new hosts and seasoned professionals alike! TIMESTAMPS 01:05 - Guest intro: Emanuel Pani and his impact on the industry 02:49 - The importance of understanding where you are and where you want to be 04:00 - The mindset shift needed to transition from W2 to full-time hosting 06:07 - E's personal journey and the power of environment in achieving success 12:02 - Tools and strategies to overcome the fear of making big decisions 17:01 - The role of self-image in your accomplishments and how to upgrade your mindset 27:06 - The importance of clear communication with your partner about business goals 31:02 - How to reassess your goals and adjust your path as circumstances change 36:21 - The relationship between identity and achievements in entrepreneurship 46:47 - How to take massive action and commit to your personal growth 54:42 - Final thoughts and how to connect with Emanuele Pani Connect with the Guest: Website: https://dolcevitamanagement.com/ Linkedin: https://www.linkedin.com/in/emanuele-pani-0b2970105/ Instagram: https://www.instagram.com/epani.realestate/?hl=en Linktree: https://linktr.ee/epani #MindsetShift #ShortTermRentals #Entrepreneurship #PersonalGrowth #STRSecrets --- Support this podcast: https://podcasters.spotify.com/pod/show/hasslefreere/support

Welcome to the show! Join us for another episode of Short Term Rental Success LIVE! This week, hosts Will and Dave dive deep into the world of automation, covering messaging, marketing strategies, pricing, and beyond. Discover expert tips to optimize efficiency and lighten your workload. Every week, we delve into strategies, topics, tips, and tricks aimed at boosting your success as a short-term rental operator. About your hosts: Will stands as the leading Short-Term Rental Real Estate Agent in New England, licensed in ME, NH, and VT. In addition to selling, he owns a small portfolio of STRs. (www.willvanwickler.com) Dave serves as the CEO of the 5 Star Co Host, an Airbnb management and consulting company. He has extensive experience, hosting thousands of stays on Airbnb. His firsthand knowledge and expertise have assisted numerous operators in replicating his success! (https://5strcohost.com/) --- Support this podcast: https://podcasters.spotify.com/pod/show/hasslefreere/support

Short Term Rental Success LIVE: Navigating Short-Term Rental Insurance Welcome to the show! Join us for another episode of Short Term Rental Success LIVE! This week, hosts Will and Dave are joined by the knowledgeable Susan Terhune, owner of one of New England's most successful insurance agencies under State Farm. With over three decades of experience and a specialization in serving short-term rental owners, Susan is the ultimate authority in navigating the complexities of insurance. As a hands-on expert, she not only talks the talk but walks the walk, managing two short-term rentals of her own. Tune in as we uncover essential insights into insuring your vacation rentals for ultimate peace of mind. About your hosts: Dave serves as the CEO of the 5 Star Co Host, an Airbnb management and consulting company. He has extensive experience, hosting thousands of stays on Airbnb. His firsthand knowledge and expertise have assisted numerous operators in replicating his success! (https://5strcohost.com/) Will stands as the leading Short-Term Rental Real Estate Agent in New England, licensed in ME, NH, and VT. In addition to selling, he owns a small portfolio of STRs. (www.willvanwickler.com) --- Support this podcast: https://podcasters.spotify.com/pod/show/hasslefreere/support

Welcome to the show! This week, Will and Dave will be discussing the critical aspects of managing finances and budgeting within your short-term rental venture. These elements are essential pillars in ensuring the profitability of your properties. Every week, we delve into strategies, topics, tips, and tricks aimed at boosting your success as a short-term rental operator. About your hosts: Will stands as the leading Short-Term Rental Real Estate Agent in New England, licensed in ME, NH, and VT. In addition to selling, he owns a small portfolio of STRs. (www.willvanwickler.com) Dave serves as the CEO of the 5 Star Co Host, an Airbnb management and consulting company. He has extensive experience, hosting thousands of stays on Airbnb. His firsthand knowledge and expertise have assisted numerous operators in replicating his success! (https://5strcohost.com/) --- Support this podcast: https://podcasters.spotify.com/pod/show/hasslefreere/support

Short Term Rental Success LIVE | Your Essential Pre-Launch Checklist Welcome to the show! This week, Will and Dave will be discussing the crucial steps for ensuring success with your new short-term rental listing. Drawing from Dave's wealth of experience with thousands of stays hosted, we'll be dissecting his personal checklist for launching a new STR. Every week, we delve into strategies, topics, tips, and tricks aimed at boosting your success as a short-term rental operator. About your hosts: Will stands as the leading Short-Term Rental Real Estate Agent in New England, licensed in ME, NH, and VT. In addition to selling, he owns a small portfolio of STRs. (www.willvanwickler.com) Dave serves as the CEO of the 5 Star Co-Host, an Airbnb management and consulting company. He has extensive experience, hosting thousands of stays on Airbnb. His firsthand knowledge and expertise have assisted numerous operators in replicating his success! (https://5strcohost.com/) --- Support this podcast: https://podcasters.spotify.com/pod/show/hasslefreere/support

Short-Term Rental Success LIVE: Insights into the Current State of the Short-Term Rental Market Welcome to the show! This week, Will and Dave will provide a comprehensive update on the state of the market. They'll delve into a recap of Q1, examining booking and market trends, while also offering insights into what lies ahead as we transition into spring and summer. Tune in for an informative discussion! Every week, we delve into strategies, topics, tips, and tricks aimed at boosting your success as a short-term rental operator. About your hosts: Will stands as the leading Short-Term Rental Real Estate Agent in New England, licensed in ME, NH, and VT. In addition to selling, he owns a small portfolio of STRs. (www.willvanwickler.com) Dave serves as the CEO of the 5 Star Co-Host, an Airbnb management and consulting company. He has extensive experience, hosting thousands of stays on Airbnb. His firsthand knowledge and expertise have assisted numerous operators in replicating his success! (https://5strcohost.com/  --- Support this podcast: https://podcasters.spotify.com/pod/show/hasslefreere/support

Welcome to another episode of Hassle Free RE! This week we welcome Michael Zaplin to the show!  Michael is a healthcare professional who has built an impressive real estate portfolio over the last several years!  Michael is passionate about creating alternative streams of income through real estate.  He explains the importance of doing so and why income diversification can help avoid physician burnout. Tune in for a gripping episode!  #HospitalityJourney #VacationExperiences #InspiringStories #PodcastEpisode #HassleFreeRE #VacationHomeOwner #PropertyManagement #HospitalityMindset #LifeJourney #Hospitality #airbnbsuperhost #vrbopremierhost #strtips #airbnb #airbnbsuperhost @5starcohost About your hosts: Dave serves as the President of the 5 Star Co-Host, an Airbnb management and consulting company. He has extensive experience, hosting thousands of stays on Airbnb. His firsthand knowledge and expertise have assisted numerous operators in replicating his success! (https://5strcohost.com/) Instagram: @dave_menapace     @kimmenapace  @5starcohost --- Support this podcast: https://podcasters.spotify.com/pod/show/hasslefreere/support

Welcome to another episode of Short-Term Rental Success! This week, we dive into the topic of "Handling Neighbors of your STR". In this discussion, we'll cover how to make friends with the locals and effectively add them to your team! When that proves to be impossible, we'll discuss how to manage that friction so everyone - guests and neighbors, stays happy! Accompanied by our guest, Kim Menapace. Beyond being Dave's significant other, Kim boasts an impressive resume as a best-selling author, real estate investor, co-founder of the 5 Star Co-Host, and a Principal Product Manager at a technology and data analytics firm. With a master's degree from Bentley University in Human Factors in Information Design, Kim brings invaluable expertise to our discussion on this topic.  #HospitalityJourney #VacationExperiences #InspiringStories #PodcastEpisode #HassleFreeRE #VacationHomeOwner #PropertyManagement #HospitalityMindset #LifeJourney #Hospitality #airbnbsuperhost #vrbopremierhost #strtips #airbnb #airbnbsuperhost @5starcohost @kimmenapace @ About your hosts: Will stands as the leading Short-Term Rental Real Estate Agent in New England, licensed in ME, NH, and VT. In addition to selling, he owns a small portfolio of STRs. (www.willvanwickler.com) Dave serves as the CEO of the 5 Star Co-Host, an Airbnb management and consulting company. He has extensive experience, hosting thousands of stays on Airbnb. His firsthand knowledge and expertise have assisted numerous operators in replicating his success! (https://5strcohost.com/) Instagram: @wvwickler @dave_menapace     @kimmenapace  @5starcohost --- Support this podcast: https://podcasters.spotify.com/pod/show/hasslefreere/support

Welcome to the show, Rashmi!!  Rashmi is a multi-business entrepreneur! Most recently, her focus has taken her into the hospitality space where she owns several short-term rentals and runs an extremely successful Short Term Rental property management business!  In addition, she has been making waves on social media as a STR influencer and educator in the space!  Tune in for this fantastic interview with Rashmi Baht!  #HospitalityJourney #VacationExperiences #InspiringStories #PodcastEpisode #HassleFreeRE #VacationHomeOwner #PropertyManagement #HospitalityMindset #LifeJourney #Hospitality #airbnbsuperhost #vrbopremierhost #strtips Links from the show: www.5strcohost.com www.tailoredstays.co Instagram: @rashmibhatofficial @Hasslefreere @5starcohost @tailoredstays.co @dave_menapace About the podcast hosts: Hosted by Dave Menapace & Anson Roberts - this is a real estate podcast for investors, those thinking of getting into investing, or anyone that is generally interested in what's happening today in the real estate market. Dave and Anson both operate Short Term Rental investment and management companies, but also have experience with long term rentals and flips. This podcast is perfect no matter where you are in your real estate journey! Contact Info for Hosts: Dave Menapace (Email: dave@5strcohost.com) Anson Roberts (Email: anson@tailoredstays.co) --- Support this podcast: https://podcasters.spotify.com/pod/show/hasslefreere/support

Welcome to the show Kim Menapace! Kim is the CEO of The 5-Star Co-Host and she has a deep background in Usability Experience and the psychology behind how and why products are used! Now, she brings that expertise to STRs and how to leverage this skillset to deliver an amazing guest experience! Looking to learn more from Kim? You can reach out to her on instagram @kimmenapace or drop an inquiry on www.5strcohost.com About your hosts:Will stands as the leading Short-Term Rental Real Estate Agent in New England, licensed in ME, NH, and VT with Keller Williams Realty. In addition to selling, he owns a small portfolio of STRs. (www.willvanwickler.com) Dave serves as the CEO of the 5 Star Co Host, an Airbnb management and consulting company. He has extensive experience, hosting thousands of stays on Airbnb. His firsthand knowledge and expertise have assisted numerous operators in replicating his success! (https://5strcohost.com/) --- Support this podcast: https://podcasters.spotify.com/pod/show/hasslefreere/support

Welcome to the show, Jess!!  Jess is the Director of Operations for The 5-Star Co-Host, LLC!  In today's episode, Jess shares her biggest takeaways from the STR Growth Summit with Stacey St. John! Tune in for the tips from top industry experts!  #HospitalityJourney #VacationExperiences #InspiringStories #PodcastEpisode #HassleFreeRE #VacationHomeOwner #PropertyManagement #HospitalityMindset #LifeJourney #Hospitality #airbnbsuperhost #vrbopremierhost #strtips Links from the show: www.5strcohost.com www.tailoredstays.co Instagram: @Hasslefreere @5starcohost @tailoredstays.co @dave_menapace About the podcast hosts: Hosted by Dave Menapace & Anson Roberts - this is a real estate podcast for investors, those thinking of getting into investing, or anyone that is generally interested in what's happening today in the real estate market. Dave and Anson both operate Short Term Rental investment and management companies, but also have experience with long term rentals and flips. This podcast is perfect no matter where you are in your real estate journey! Contact Info for Hosts: Dave Menapace (Email: dave@5strcohost.com) Anson Roberts (Email: anson@tailoredstays.co) --- Support this podcast: https://podcasters.spotify.com/pod/show/hasslefreere/support

This week we record live from Nashville at the STR Wealth conference! Learn our biggest takeaways from the conference! Welcome to the weekly live podcast hosted by Dave and Will! Every week, we delve into strategies, topics, tips, and tricks aimed at boosting your success as a short-term rental operator. About your hosts: Will stands as the #1 Short-Term Rental Real Estate Agent in New England, licensed in ME, NH, and Vermont. In addition to selling, he owns a small portfolio of STRs across Maine. (www.willvanwickler.com) Dave serves as the CEO of the 5 Star Co Host, an Airbnb management and consulting company. He has extensive experience, hosting thousands of stays on Airbnb. His firsthand knowledge and expertise have assisted numerous operators in replicating his success! (https://5strcohost.com/) --- Support this podcast: https://podcasters.spotify.com/pod/show/hasslefreere/support

Welcome to the weekly live podcast hosted by Dave and Will! Every week, we delve into strategies, topics, tips, and tricks aimed at boosting your success as a short-term rental operator. About your hosts: Will stands as the #1 Short-Term Rental Real Estate Agent in New England, licensed in ME, NH, and Vermont. In addition to selling, he owns a small portfolio of STRs across Maine. (www.willvanwickler.com) Dave serves as the CEO of the 5 Star Co Host, an Airbnb management and consulting company. He has extensive experience, hosting thousands of stays on Airbnb. His firsthand knowledge and expertise have assisted numerous operators in replicating his success! (https://5strcohost.com/) --- Support this podcast: https://podcasters.spotify.com/pod/show/hasslefreere/support

Welcome to the weekly live podcast hosted by Dave and Will! Every week, we delve into strategies, topics, tips, and tricks aimed at boosting your success as a short-term rental operator. About your hosts: Will stands as the #1 Short-Term Rental Real Estate Agent in New England, licensed in ME, NH, and Vermont. In addition to selling, he owns a small portfolio of STRs across Maine. (www.willvanwickler.com) Dave serves as the CEO of the 5 Star Co Host, an Airbnb management and consulting company. He has extensive experience, hosting thousands of stays on Airbnb. His firsthand knowledge and expertise have assisted numerous operators in replicating his success! (https://5strcohost.com/) --- Support this podcast: https://podcasters.spotify.com/pod/show/hasslefreere/support

Welcome to the show, Skylar! Skylar is the founder and managing partner of Maine Pointe Lending. She stands out as one of the premier loan originators and shares a mutual interest in short-term rental investments. This week, our focus turns to the market outlook and the pressing question on everyone's mind—what's happening in the mortgage world? Whether you're an owner or aspiring to become one, this episode promises a wealth of valuable insights. Every week, we delve into strategies, topics, tips, and tricks aimed at boosting your success as a short-term rental operator. About your hosts: Will stands as the #1 Short-Term Rental Real Estate Agent in New England, licensed in ME, NH, and Vermont. In addition to selling, he owns a small portfolio of STRs across Maine. (www.willvanwickler.com) Dave serves as the CEO of the 5 Star Co Host, an Airbnb management and consulting company. He has extensive experience, hosting thousands of stays on Airbnb. His firsthand knowledge and expertise have assisted numerous operators in replicating his success! (https://5strcohost.com/) Guest Skylar Welch: My goal is to always make each client a customer for life, as I want to be there with you, every step of your life for your lending needs! I am always available and can be contacted any day of the week, as I understand that purchasing a home is not something that always takes place during bankers hours. I look forward to helping make your homeownership dreams come true! (www.mainepointelending.com) MLO NMLS #86901 --- Support this podcast: https://podcasters.spotify.com/pod/show/hasslefreere/support

Welcome to the weekly live podcast hosted by Dave and Will! Every week, we delve into strategies, topics, tips, and tricks aimed at boosting your success as a short-term rental operator. About your hosts: Will stands as the #1 Short-Term Rental Real Estate Agent in New England, licensed in ME, NH, and Vermont. In addition to selling, he owns a small portfolio of STRs across Maine. (www.willvanwickler.com) Dave serves as the CEO of the 5 Star Co Host, an Airbnb management and consulting company. He has extensive experience, hosting thousands of stays on Airbnb. His firsthand knowledge and expertise have assisted numerous operators in replicating his success! (https://5strcohost.com/) --- Support this podcast: https://podcasters.spotify.com/pod/show/hasslefreere/support

Welcome to the show Shane!  Shane joins us from Orlando, Florida where he owns and manages a fairytale-like portfolio of amazing vacation homes!  From the navy to hospitality has been Shane's journey.  Faced with personal challenges and tragedy, he leaned into mindset and hospitality to craft amazing vacation experiences and has built a life that is truly inspiring! Links from the show: www.vacationalchemy.com www.5strcohost.com www.tailoredstays.co Instagram: @vacation.alchemy  @Hasslefreere @5starcohost @tailoredstays.co @dave_menapace About the podcast hosts: Hosted by Dave Menapace & Anson Roberts - this is a real estate podcast for investors, those thinking of getting into investing, or anyone that is generally interested in what's happening today in the real estate market. Dave and Anson both operate Short Term Rental invesment and mangement companies, but also have experience with long term rentals and flips. This podcast is perfect no matter where you are in your real estate journey! Contact Info for Hosts: Dave Menapace (Email: dave@5strcohost.com) Anson Roberts (Email: anson@tailoredstays.co) --- Support this podcast: https://podcasters.spotify.com/pod/show/hasslefreere/support

Welcome to the show Darryl and Ashley! Meeting this amazing short term rental power couple! Darryl and Ashley are the founders of Stay Space, a premier vacation rental management company covering the better part of New England! Tune in to hear their amazing story from cohosting to now published authors! Links from the show: www.stayspace.net www.5strcohost.com www.tailoredstays.co Instagram: @Hasslefreere @5starcohost @tailoredstays.co @dave_menapace About the podcast hosts: Hosted by Dave Menapace & Anson Roberts - this is a real estate podcast for investors, those thinking of getting into investing, or anyone that is generally interested in what's happening today in the real estate market. Dave and Anson both operate Short Term Rental invesment and mangement companies, but also have experience with long term rentals and flips. This podcast is perfect no matter where you are in your real estate journey! Contact Info for Hosts: Dave Menapace (Email: dave@5strcohost.com) Anson Roberts (Email: anson@tailoredstays.co) --- Support this podcast: https://podcasters.spotify.com/pod/show/hasslefreere/support

Welcome to the show Allie and Carrie! Allie and Carrie are two amazingly talented women in the STR industry! Each has an impressive portfolio of STRs, cohost clients, hotels, and more! They each are coaches for the STR Secrets mastermind and they also host a popular STR podcast called "She Invests"! Tune in to hear their incredible stories and learn the incredible impact they are making on the STR industry! Links from the show: www.5strcohost.com www.tailoredstays.co https://www.facebook.com/CherokeeRoseHomes https://podcasts.apple.com/us/podcast/she-invests/id1682074272 Instagram: @she_hosts_blueridge @carriedouglasrealtor @Hasslefreere @5starcohost @tailoredstays.co @menapace_realestate About the podcast hosts: Hosted by Dave Menapace & Anson Roberts - this is a real estate podcast for investors, those thinking of getting into investing, or anyone that is generally interested in what's happening today in the real estate market. Dave and Anson both operate Short Term Rental invesment and mangement companies, but also have experience with long term rentals and flips. This podcast is perfect no matter where you are in your real estate journey! Contact Info for Hosts: Dave Menapace (Email: dave@5strcohost.com) Anson Roberts (Email: anson@tailoredstays.co) --- Support this podcast: https://podcasters.spotify.com/pod/show/hasslefreere/support

Welcome back to the show, Kim! Kim is the CEO of The 5-Star Co-Host, a luxury vacation rental management company in New England. Kim recently attended WealthCon in Las Vegas. In this episode she shares her take aways from the conference with notable speakers such as Ed Mylett and Ryan Pineda! Links from the show: www.5strcohost.com www.tailoredstays.co Instagram: @Hasslefreere @5starcohost @tailoredstays.co @menapace_realestate About the podcast hosts: Hosted by Dave Menapace & Anson Roberts - this is a real estate podcast for investors, those thinking of getting into investing, or anyone that is generally interested in what's happening today in the real estate market. Dave and Anson both operate Short Term Rental invesment and mangement companies, but also have experience with long term rentals and flips. This podcast is perfect no matter where you are in your real estate journey! Contact Info for Hosts: Dave Menapace (Email: dave@5strcohost.com) Anson Roberts (Email: anson@tailoredstays.co) --- Support this podcast: https://podcasters.spotify.com/pod/show/hasslefreere/support

Welcome to the show, Skylar! Skyler is an absolute rockstar. The top lender in Maine, she is the founder of Maine Pointe Lending...but that's not all. Skyler has been an entreprenuer her entire life and she's leveraged that skillset and work ethic to not only lead the state in lending, but her and her husband have also launched a very successful wedding venue and operate their own Airbnb's! Links from the show: www.moonlitridge.com www.mainepointelending.com www.5strcohost.com www.tailoredstays.co Instagram: @moonlitridgeevents @skyeclosesmaine @mainepointelending @Hasslefreere @5starcohost @tailoredstays.co @menapace_realestate About the podcast hosts: Hosted by Dave Menapace & Anson Roberts - this is a real estate podcast for investors, those thinking of getting into investing, or anyone that is generally interested in what's happening today in the real estate market. Dave and Anson both operate Short Term Rental invesment and mangement companies, but also have experience with long term rentals and flips. This podcast is perfect no matter where you are in your real estate journey! Contact Info for Hosts: Dave Menapace (Email: dave@5strcohost.com) Anson Roberts (Email: anson@tailoredstays.co) --- Support this podcast: https://podcasters.spotify.com/pod/show/hasslefreere/support

Welcome to the show, Casey! Casey is a real estate investor, short term rental operator, a best selling author, and hospitable host! Casey owns and operates STRs. Its a family operated company where each member has a unique role in the business. We're so excited to share Casey's story with everyone! Learn how he leveraged his prior work experience with his family to build the business of his dreams and live his life on his terms! Links from the show: www.5strcohost.com www.tailoredstays.co Instagram: @casey_karlen @Hasslefreere @5starcohost @tailoredstays.co @menapace_realestate About the podcast hosts: Hosted by Dave Menapace & Anson Roberts - this is a real estate podcast for investors, those thinking of getting into investing, or anyone that is generally interested in what's happening today in the real estate market. Dave and Anson both operate Short Term Rental invesment and mangement companies, but also have experience with long term rentals and flips. This podcast is perfect no matter where you are in your real estate journey! Contact Info for Hosts: Dave Menapace (Email: dave@5strcohost.com) Anson Roberts (Email: anson@tailoredstays.co) Support this podcast: https://podcasters.spotify.com/pod/show/hasslefreere/support --- Support this podcast: https://podcasters.spotify.com/pod/show/hasslefreere/support

What a wonderful episode we have for our listeners this week! In this weeks show, we introduce the new book "Creating a life of Abundance" which luanches on October 4th, 2023! The book captures the journeys of 4 different couples who have built a life of abundance together through real estate. Each story goes deep into the challenges and success that each couple has gone through personally and professionally to get to where they are today. Links from the show: www.cashstreettech.com www.duffyhomesllc.com www.simplyrelaxstays.com www.strcouple.com www.duffley.com www.5strcohost.com www.tailoredstays.co https://www.facebook.com/duffyhomesbranson https://www.facebook.com/andrew.hanson.98284 Instagram: @cashstreetcouple @Hasslefreere @5starcohost @tailoredstays.co @menapace_realestate About the podcast hosts: Hosted by Dave Menapace & Anson Roberts - this is a real estate podcast for investors, those thinking of getting into investing, or anyone that is generally interested in what's happening today in the real estate market. Dave and Anson both operate Short Term Rental invesment and mangement companies, but also have experience with long term rentals and flips. This podcast is perfect no matter where you are in your real estate journey! Contact Info for Hosts: Dave Menapace (Email: dave@5strcohost.com) Anson Roberts (Email: anson@tailoredstays.co) --- Support this podcast: https://podcasters.spotify.com/pod/show/hasslefreere/support