PODCAST · business
Hassle Free RE
by Hassle Free RE
Hosted by Dave Menapace & Will Van Wickler - 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 Will are both industry thought leaders and own several real estate businesses, from real estate sales teams, consulting firms, and property management companies. This podcast is perfect no matter where you are in your real estate journey!
Episodes
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90 - From W-2 to STR Co-Hosting: Maine Markets, Amenities, and Expansion with Matt Welch
Welcome to Hassle-Free RE! Today, Dave Menapace and Will Van Wickler sit down with guest Matt Welch—a former CPG sales leader who left his W-2 to scale a short-term rental portfolio and co-hosting company across Maine. Matt shares how he and his partners built an owner-first management model, why...
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89 - Vacation Rental Design Trends: ROI Myths, Amenities, and Guest Experience
Welcome to Hassle-Free RE! Today, Dave Menapace and Will Van Wickler take a closer look at vacation rental design trends and uncover why not all upgrades and amenities actually boost your ROI. From flashy but impractical amenities to simple design tweaks that consistently improve guest...
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88 - Scaling Beyond 10 Properties: Hidden Costs, Mindset Shifts, and Team Building
Welcome to Hassle-Free RE! Today, Dave Menapace and Will Van Wickler break down what it really takes to scale beyond 10 properties in the short-term rental business. From hidden costs to operational complexity, they reveal the challenges no one talks about and the mindset shifts required to build…
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87 - The War on Short-Term Rentals: Regulation, Opportunity, and Due Diligence
Welcome to our latest episode! Today, Dave Menapace and Will Van Wickler tackle one of the most pressing issues in real estate and hospitality—the growing wave of short-term rental regulations. From Boston and Portland to vacation markets like Cape Cod and Bar Harbor, they break down how local...
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86 - Airbnb vs. Boutique Hotels: Shifts, Standards, and the Future of Hospitality
Welcome to our latest episode! Today, Dave Menapace and Will Van Wickler dive into one of the hottest debates in hospitality—Airbnb versus boutique hotels. With firsthand experience managing both luxury vacation rentals and boutique hotels across New England, they unpack the shifts in traveler...
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85 - From Superhost to Co-Host: Jason Muth’s Short-Term Rental Evolution
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…
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84 - Building a Winning Team: Leadership, Virtual Assistants, and Business Growth
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…
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83 - Lessons from Vegas – Mindset, Masterminds, and Business Growth
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…
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82 - The Power of Self-Managing Your Short-Term Rental with Chris Petzy
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...
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81 - Breaking Down Newry’s Proposed STR Ordinance
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...
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80 - Systemizing Real Estate Investing – Virtual Assistants, Automation, and Time Freedom with Adrienne Green
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...
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79 - Founder, No Worry Home - Your MVP in home and guest protection with Jon Levitt
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...
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78 - A season of growth - Navigating Real Estate, Business Scaling, and Mindset!
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...
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77 - Building Passive Income and Leveraging STR Growth with Bernie Cesareo
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...
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76 - 2024 Real Estate Recap and 2025 Predictions
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…
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75 - Optimizing STR Maintenance with Jess Lea
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...
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74 - Maximizing STR Growth in Winter Markets
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…
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73 - Unlocking STR Potential in Old Orchard Beach
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...
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72 - Expert Tips for Short-Term Rental Success in Sunday River
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...
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71 - The Complete Guide to Hot Tubs, Saunas & Swim Spas for Short-Term Rentals
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...
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70 - Flipping vs. New Construction: Choosing the Right Path in Real Estate
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,...
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69 - Navigating Reviews and Buying the Ideal STR Property
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...
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68 - Crafting the Perfect Offer for Buying a Home
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…
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67 - Moving Beyond OTAs: Strategic Markets & Winning Amenities with Kenneth Bedwell
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...
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66 - Breaking Away from OTAs
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,...
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65 - Scaling STRs and Mastering Direct Booking Marketing with Sam Mistretta
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...
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64 - Protect Your Property and Ensure Guest Safety!
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...
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63 - Effective Neighbor Management and STR Tech for Hassle-Free Operations
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,...
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62 - Becoming a Leading STR Real Estate Agent
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…
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61 - STR Success in the Old Orchard Beach Market
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...
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60 - How to prepare for selling your STR
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…
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59 - Clean Sweep Short Term Rental Cleaning Mastery
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,...
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58 - Pro Strategies for Preventative Maintenance
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...
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57 - Creating a Life of Success and Growth with Emanuele Pani
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...
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56 - STR Success - Streamlining your business with these automations!
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...
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55- STR Success - Navigating Short Term Rental Insurance w/Susan Terhune
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...
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54 - STR Success - Mastering Finances and Budgeting for Your STR Business
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…
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53 - STR Success - Your ESSENTIAL Pre-Launch Checklist
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...
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52 - STR Success - Insights into the state of the STR industry
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...
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51 - Michael Zaplin - The Importance of Creating Financial Freedom for Healthcare Professionals
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…
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STR Success - Handling the Neighbors of your Airbnb
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...
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49 - Rashmi Baht - Multi-Industry Entrepreneur Makes Waves in Hospitality
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…
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STR Success - Usability Experience in STR with Kim Menapace
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!...
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Episode 48 - Jess Lea - Takeaways from the STR Growth Summit
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...
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STR Success - Dave & Will record live from the Nashville Studio at the STR Wealth Conference!
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...
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STR Success - Dave & Will Discuss the topic of allowing dogs at your STR
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…
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STR Success - Dave & Will discuss critical tech for investing and operating STRs
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…
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STR Success - Dave & Will Discuss Investing & Mortgages w/ Skylar Welch
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...
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STR Success - Dave & Will cover the 2024 STR Industry Outlook
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…
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47 - Shane O'Connor - Overcoming personal tragedy and getting creative with hospitality
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…
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ABOUT THIS SHOW
Hosted by Dave Menapace & Will Van Wickler - 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 Will are both industry thought leaders and own several real estate businesses, from real estate sales teams, consulting firms, and property management companies. This podcast is perfect no matter where you are in your real estate journey!
HOSTED BY
Hassle Free RE
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Frequently Asked Questions
How many episodes does Hassle Free RE have?
Hassle Free RE currently has 96 episodes available on PodParley. New episodes are automatically indexed when they're published to the podcast feed.
What is Hassle Free RE about?
Hosted by Dave Menapace & Will Van Wickler - 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 Will are both industry thought leaders and own several real estate...
How often does Hassle Free RE release new episodes?
Hassle Free RE has 96 episodes. Check the episode list to see recent publication dates and frequency.
Where can I listen to Hassle Free RE?
You can listen to Hassle Free RE on PodParley by clicking any episode. We provide an embedded audio player for direct listening, and you can also subscribe via your preferred podcast app using the RSS feed.
Who hosts Hassle Free RE?
Hassle Free RE is created and hosted by Hassle Free RE.
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