Podcasts about short term rentals

Send us a message!In this week's episode, we're joined by Matt Gurley, Director of Sales and Partner Integrations at the Lynnbrook Group, for a deep dive into the payment side of vacation rentals that most property managers overlook until it's too late.From fraud prevention to faster checkouts to smarter cash flow tools, Matt breaks down how Lynnbrook is simplifying payment processing and helping operators keep more of what they earn. With a career that started in the OTA integration trenches and evolved into leading-edge fintech, Matt brings a unique perspective on why vacation rental companies need more than just a generic payment provider.If you've ever dealt with chargebacks, payout delays, or struggled with reconciling your books, this one's for you.Key Topics Discussed:1️⃣ Why payment processing is more than just a backend task in vacation rentals2️⃣ Common blind spots property managers face when it comes to fraud and chargebacks3️⃣ How modern checkout options like Apple Pay, Pay Later, and Venmo are shaping guest expectations4️⃣ What property managers can do to protect profits and streamline payouts5️⃣ The importance of industry-specific tools for high-risk booking scenarios6️⃣ Lessons learned from OTAs, hurricanes, and helping PMs stay financially stable7️⃣ What operators should ask when choosing a payment partner8️⃣ The real cost of ignoring risk and complianceConnect with Matt:LinkedIn: https://www.linkedin.com/in/matthew-gurley-74688592/ Website: https://www.lynnbrookgroup.com/ Mention "Alex & Annie" when you sign up with Boom to get 50% off your onboarding fee and 1 month FREE: ⁠⁠⁠https://www.boomnow.com/⁠⁠Get a free Growth Hack Review and P&L Evaluation when you mention “Alex & Annie” during your discovery call with the Grand Welcome team: https://calendly.com/jessica-singer-grandwelcome/intro#vacationrentals #shorttermrentals #paymentprocessing

Short-term rentals—popularized by Airbnb and Vrbo—have been given modern platforms for the customary alternative to hotels: in-home stays. Yet their rapid growth has prompted a wave of local and state regulations at odds with the practice, driven by lobbying from the hotel industry, concerns about housing affordability, neighborhood character, and other regulatory assertions. While some critics, including city officials and interest groups, support increased oversight, others—including advocates of limited government and individual rights—contend that these services represent an exercise of property rights, expand consumer choice, and note that there is limited evidence of significant impact on the housing market.This panel will explore the constitutional, statutory, historical, and policy implications of short-term rental regulation. Are local governments properly protecting community interests, or are they infringing on fundamental property rights? What legal frameworks govern this space—and what should they be?Join us for a lively discussion featuring the Hon. Paul Clement, Tony Francois, and Ron Klain, moderated by Prof. Donald Kochan, that will examine the intersection of private property, regulatory authority, and economic liberty.

Send us a message!In this episode, we sit down with two industry powerhouses: Dennis Goedheid, CEO of Casiola, and Shahar Goldboim, CEO of Boom and founder of DesignedVR, to unpack the story behind their groundbreaking new partnership.As the vacation rental industry continues to mature, operators are finding new ways to grow that prioritize sustainability, clarity, and control. This conversation explores the revenue-sharing agreement between DesignedVR and Casiola, a creative alternative to the traditional franchise or acquisition model.Shahar shares his decision to step away from the day-to-day operations of DesignedVR to fully focus on growing Boom, the AI-powered property management system he built with his two brothers. Dennis explains how Casiola's clear focus on hospitality and operations made them the right partner to take over and grow the DesignedVR portfolio.Key Topics Discussed:1️⃣ Why Shahar chose to partner rather than sell or franchise2️⃣ How Dennis and Shahar aligned on values, leadership, and long-term vision3️⃣ What property managers can learn about letting go to grow4️⃣ The operational and cultural challenges of integrating a new team and brand5️⃣ How Casiola approaches expansion without sacrificing focus6️⃣ Why the traditional "do it all" mindset often leads to burnout in STR7️⃣ How Dennis views focus as a competitive advantage8️⃣ Why Shahar sees clarity as a form of leadership9️⃣ What role AI and automation will play as Boom continues to scaleYou'll also hear how Casiola is managing the integration of DesignedVR's team, technology, and properties, and why this move is about more than just operations. At its core, it's a partnership built on aligned values and a shared vision for what vacation rental businesses can become.Connect with Shahar:LinkedIn: https://www.linkedin.com/in/shahar-goldboim-80820b95/ Boom: https://www.boomnow.com/ Connect with Dennis:LinkedIn: https://www.linkedin.com/in/dennisgoedheid/ Casiola: https://www.casiola.com/ Mention "Alex & Annie" when you sign up with Boom to get 50% off your onboarding fee and 1 month FREE: ⁠⁠⁠https://www.boomnow.com/⁠⁠Get a free Growth Hack Review and P&L Evaluation when you mention “Alex & Annie” during your discovery call with the Grand Welcome team: https://calendly.com/jessica-singer-grandwelcome/intro #vacationrentals #vacationrentalfranchising #STR

Think long-term tenants cause less damage than short-term guests? Think again. In this episode, we dive into surprising data from Tim's personal portfolio showing how short-term rentals can actually reduce your maintenance costs. Discover the real numbers, real stories, and real savings that might change your rental strategy forever. Why long-term rentals may cost you more in the long run—especially after tenant turnover Real-world maintenance savings Tim uncovered over 10+ years of STR operations How frequent cleanings and guest stays actually help preserve your property The secret power of proactive maintenance in short-term rental success What landlords often overlook when calculating true maintenance costs Short-term rentals aren't just higher income—they can actually be lower maintenance, too. If you've only considered LTRs for their “ease,” this episode may shift your thinking. Want to keep learning? Don't forget to subscribe, share this with a fellow investor, and check out our helpful resources below. Resource Links Check out our videos on YouTube: https://www.youtube.com/@ShortTermRentalRiches Grab your free management eBook: https://strriches.com/#tools-resources Looking to earn more with your property (without the headaches)? Chat with our expert management team: https://strriches.com/management-services/

This week Cameron and Anthony dig into the world of Airbnb investing with John Bianchi, a specialist who boasts a 100% success rate in guiding clients to profitable short-term rental properties. John debunks common misconceptions about the Airbnb market, lays out his proven evaluation methods—including the “20% rule”—and dives into the differences between long-term and short-term rental strategies. The conversation highlights the importance of data over guesswork, especially when it comes to selecting markets, assessing true property potential, and leveraging tax advantages unique to Airbnbs. John also shares details about new tax legislation and how his team at STR Search makes investing stupid simple for their clients.   Resources: STR Search: How We Can Help You Join the Infinite Wealth Study Group: https://www.facebook.com/share/g/qC3sAWg6PhHYpRAs/  Schedule your 15-minute call with Anthony or Cameron here: http://bit.ly/iwc15podcast Check our online course at www.InfiniteWealthCourse.com Buy Becoming Your Own Banker by R. Nelson Nash http://bit.ly/BYOBbookIWC 

Want to boost your Airbnb bookings and stand out in a crowded short-term rental market? In this episode of the STR Sisterhood Podcast, I'm joined by Liz Lyons—an expert in short-term rental photography who knows exactly how to turn a listing into a scroll-stopper. With her deep hospitality roots and a creative eye that knows what converts, Liz breaks down how high-quality, professional photos can dramatically increase your occupancy rates and revenue. We explore how to turn your Airbnb or vacation rental into a booking magnet through visual storytelling—because it's not just about snapping pretty pictures. It's about showcasing the experience guests can expect and highlighting the unique features that make your property unforgettable. From lighting and angles to staging tips and must-have hero shots, Liz shares the insider secrets every host needs to know to attract the right guests—and get them to click “Book Now” faster than ever. If you're ready to elevate your short-term rental listing and create visuals that sell your stay before guests even arrive, don't miss this game-changing conversation. HIGHLIGHTS AND KEY POINTS: [01:18] A short introduction about our guest Liz Lyons and how she ventured in the world of the hospitality industry [05:35] Liz's perspective on how photography serves as a marketing tool to attract your ideal guest [07:55] Liz shares how to vet the right photographer for short-term rentals to align with your style and creative vision [12:31] Liz's insights on using outside photo inspiration that aren't within the photographer's portfolio [14:20] What are the must-have shots every short-term rental needs to create a wow factor [17:57] What are the key things to prepare for when your photographer shows up to ensure that the space is ready and clutter-free [24:59] Liz's approach to detailed client collaboration to enhance the client-photographer relationship in short-term rental photography [29:59] Liz's perspective to navigating remote property management and collaborating with photographers to capture the essence of a space in short-term rental photography [32:34] Liz's thoughts on professional photography and iPhone photography [37:47] The importance of high-quality photos to enhance the appeal of short-term rental listings and attract ideal guests [40:17] The lightning round Golden Nuggets: “The number one thing that people tend to forget, is that, at the end of the day, your photography really is just a marketing tool.” “Short-term rental photography is becoming such a very kind of niche little industry, because you really have to understand what your marketing and what your client wants to market.” “Your photography is the only way that you have to show people what you have to offer.” “Our responsibility as owners and operators hosts, is to position the property in the best way possible, so that what we want it to do is be a magnet for our ideal guests.” “It's so common for us to be people pleasers. I believe, as a woman, as a wife, as a mom, as a sister, a daughter, that we are okay with setting boundaries and saying no, and saying, you know what, I'm sorry, this doesn't feel right, and that's not easy to do sometimes.” Let's Connect! Website: strphotography.com Enjoyed the show? Subscribe, Rate, Review, Like, and Share!

Send us a textColin and Josh finally spill the beans on their latest mobile home park deal — a $3.6 million portfolio they locked down with (almost) no money out of pocket. But here's the catch: they actually did bring a few grand to the table… so is "no money down" just a sexy lie to sell you a course?This episode dives into what “no money out of pocket” really means, how their investor got 5% equity, and the beautiful mess of coordinating signatures with trusts, partners, and a very tired Josh who went to bed at 7:30 PM. Oh, and if you're a high-income earner looking to offset taxes — the boys talk depreciation and short-term rental loopholes too. Grab a wine (hopefully worth $460 like Colin's), and enjoy the banter.

How do you transition from a stable corporate career to building a thriving real estate empire? In this episode, we sit down with Niyi Adewole, a former corporate executive turned real estate investor managing a large portfolio of both short and long term rentals. Niyi shares his inspiring journey, from taking the leap into real estate to becoming a master of house hacking and scaling profitable rental properties. Discover: ✅ Why house hacking is a game-changer for reducing living costs and growing wealth. ✅ Proven strategies for managing short-term rentals and generating direct booking revenue. ✅ How to navigate the challenges of investing in properties across multiple markets. ✅ The creative financing methods that helped Niyi scale his portfolio. ✅ Hard-earned lessons from setbacks and how they shaped his success. If you're ready to unlock financial freedom through real estate, this episode is packed with actionable advice, insider tips, and motivational insights.

In this episode, we unpack a week full of headlines that reveal the shifting tides in America's cultural and economic landscape.We start on a high note with Ryan Coogler's latest film "Sinners" dominating the box office and stirring up critical buzz what does its success say about the appetite for bold, Black storytelling in Hollywood?Then we pivot to the economic storm clouds gathering: UPS is slashing 20,000 jobs, a move that signals deeper issues in the shipping and logistics sector. Could this be the canary in the coal mine for the broader economy?We also dive into a surprising immigration development: White South African families are reportedly being brought into the U.S. under humanitarian grounds. What's behind this—and how does it fit into America's evolving immigration narrative?On the policy front, the Trump administration's tariffs are rattling the movie and fashion industries. Major players like Nike and Adidas are lobbying hard for exemptions. If they don't get them, are empty store shelves on the horizon?And finally, we talk about a move flying under the radar but with massive implications: a potential cut to Section 8 housing. What could this mean for low-income families already struggling to stay afloat?It's a jam-packed episode of culture, policy, and hard truths—let's get into it. Enjoy!!!If you'd like to grab some merch, canvas prints for your home or office, or see the full length video from this episode please visit dopevision.com. Follow me on ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Instagram⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠, ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Facebook⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠, ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Twitter⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠, @dopevisionsf. Send me an email of someone you'd like to hear on the podcast at ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠dopevisionsf@gmail.com⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ Also, please join the Dope Vision Club at patreon.com/dopevision for early access to content and a behind the scene look of some of my episodes.While you're listening don't forget to hit the subscribe button and comment on the podcast as well my ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠YouTube channel⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ and turn on the notifications so you'll be notified each and every time I drop a new episode. Thanks for listening and remember it's collaboration over competition. Enjoy!When you're ready to create your beautiful website to promote your business don't forget about Squarespace and to support THE DOPE VISION EXPERIENCE PODCAST⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠CLICK HERE⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ to save 10% off your first subscription to your Squarespace website and use my promo code PARTNER10 at checkout⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠CLICK HERE⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ to get 30-day Free Premium Access to Printify use promo code ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠dope vision⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠If you'd like to schedule a quick 15 min meeting with me please ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Click Here⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Click Here⁠⁠⁠⁠⁠⁠ to checkout my Short Term Rental property

Want to learn more about Vodyssey or start your STR journey. Book a call here:https://meetings.hubspot.com/vodysseystrategysession/booknow?utm_source=vodysseycom&uuid=80fb7859-b8f4-40d1-a31d-15a5caa687b7The conversation covers their motivations, challenges faced during market shifts, and the importance of location and appeal in property selection. Joe and Amy discuss the hard work behind their success, emphasizing that opportunities often come at inconvenient times and require resourcefulness to navigate. In this conversation, Shawn Moore discusses the journey of building a successful property portfolio, emphasizing the importance of resilience, communication, and customer experience in the vacation rental industry.BOOK THEIR PROPERTIES:https://goparadisevacations.com/propertiesFOLLOW US:https://www.instagram.com/vodysseyshawnmoorehttps://www.facebook.com/vodysseyshawnmoore/https://www.linkedin.com/company/str-financial-freedomhttps://www.tiktok.com/@vodysseyshawnmooreGET YOUR FREE BOOK & TRAINING HERE:https://vodyssey.com/Chapters00:00:00 Intro00:02:51 The Seed of Vacation Rental Investing00:06:04 Navigating the Market Shifts00:08:49 Building the Portfolio00:12:04 Challenges and Opportunities in Property Management00:14:58 The Importance of Location and Appeal00:17:50 Scaling the Portfolio00:21:03 The Hard Work Behind Success00:26:10 Building Resilience Through Experience00:29:05 The Importance of Communication in Customer Experience00:30:52 Expanding the Property Portfolio00:34:07 Navigating Property Choices: Condos vs. Single Family Homes00:37:02 The Law of Attraction in Real Estate Investments00:45:21 Advice for Aspiring Real Estate Investors

In this episode, Ben Wolff, co-founder and developer of Onera and CEO of Oasi, shares a preview into his next big move: developing a tropical landscape resort in South Florida.Connect with Ben:LinkedInTwitter (@UniqueStaysGuy)Instagram (@IAmBenWolff)NewsletterSee our other episodes with Ben: Why Most Hotels Fail at Social Media (And How to Get It Right) Unleash Your Inner Creative: How Hospitality Leaders Can Build Something MeaningfulWhy Today's Guests Want to Be Participants, Not ObserversThe Hidden Cost of Playing It Safe: Why Hospitality Leaders Must Innovate NowHow We're Scaling Innovation and Investment from Short-Term Rentals to Hotels A few more resources: If you're new to Hospitality Daily, start here. You can send me a message here with questions, comments, or guest suggestions If you want to get my summary and actionable insights from each episode delivered to your inbox each day, subscribe here for free. Follow Hospitality Daily and join the conversation on YouTube, LinkedIn, and Instagram. If you want to advertise on Hospitality Daily, here are the ways we can work together. If you found this episode interesting or helpful, send it to someone on your team so you can turn the ideas into action and benefit your business and the people you serve! Music for this show is produced by Clay Bassford of Bespoke Sound: Music Identity Design for Hospitality Brands

In this conversation, Mike Demson shares his journey from a tech career to real estate, focusing on boutique hotels and short-term rentals. He discusses the challenges faced in the short-term rental market, including regulatory changes and operational difficulties. Mike highlights the importance of strategic partnerships and learning from experienced individuals in the industry. He also delves into his consulting business and future plans for growth in the boutique hotel sector. Professional Real Estate Investors - How we can help you: Investor Fuel Mastermind:  Learn more about the Investor Fuel Mastermind, including 100% deal financing, massive discounts from vendors and sponsors you're already using, our world class community of over 150 members, and SO much more here: http://www.investorfuel.com/apply   Investor Machine Marketing Partnership:  Are you looking for consistent, high quality lead generation? Investor Machine is America's #1 lead generation service professional investors. Investor Machine provides true ‘white glove' support to help you build the perfect marketing plan, then we'll execute it for you…talking and working together on an ongoing basis to help you hit YOUR goals! Learn more here: http://www.investormachine.com   Coaching with Mike Hambright:  Interested in 1 on 1 coaching with Mike Hambright? Mike coaches entrepreneurs looking to level up, build coaching or service based businesses (Mike runs multiple 7 and 8 figure a year businesses), building a coaching program and more. Learn more here: https://investorfuel.com/coachingwithmike   Attend a Vacation/Mastermind Retreat with Mike Hambright: Interested in joining a “mini-mastermind” with Mike and his private clients on an upcoming “Retreat”, either at locations like Cabo San Lucas, Napa, Park City ski trip, Yellowstone, or even at Mike's East Texas “Big H Ranch”? Learn more here: http://www.investorfuel.com/retreat   Property Insurance: Join the largest and most investor friendly property insurance provider in 2 minutes. Free to join, and insure all your flips and rentals within minutes! There is NO easier insurance provider on the planet (turn insurance on or off in 1 minute without talking to anyone!), and there's no 15-30% agent mark up through this platform!  Register here: https://myinvestorinsurance.com/   New Real Estate Investors - How we can work together: Investor Fuel Club (Coaching and Deal Partner Community): Looking to kickstart your real estate investing career? Join our one of a kind Coaching Community, Investor Fuel Club, where you'll get trained by some of the best real estate investors in America, and partner with them on deals! You don't need $ for deals…we'll partner with you and hold your hand along the way! Learn More here: http://www.investorfuel.com/club   —--------------------

In this episode, Ben Wolff, co-founder and developer of Onera and CEO of Oasi, shares his experiences with engaging groups and events in the hospitality industry.Connect with Ben:LinkedInTwitter (@UniqueStaysGuy)Instagram (@IAmBenWolff)NewsletterSee our other episodes with Ben: Why Most Hotels Fail at Social Media (And How to Get It Right) Unleash Your Inner Creative: How Hospitality Leaders Can Build Something MeaningfulWhy Today's Guests Want to Be Participants, Not ObserversThe Hidden Cost of Playing It Safe: Why Hospitality Leaders Must Innovate NowHow We're Scaling Innovation and Investment from Short-Term Rentals to Hotels A few more resources: If you're new to Hospitality Daily, start here. You can send me a message here with questions, comments, or guest suggestions If you want to get my summary and actionable insights from each episode delivered to your inbox each day, subscribe here for free. Follow Hospitality Daily and join the conversation on YouTube, LinkedIn, and Instagram. If you want to advertise on Hospitality Daily, here are the ways we can work together. If you found this episode interesting or helpful, send it to someone on your team so you can turn the ideas into action and benefit your business and the people you serve! Music for this show is produced by Clay Bassford of Bespoke Sound: Music Identity Design for Hospitality Brands

Send us a message!Is the short-term rental industry on the edge of a travel recession, or just entering a new phase of normalization?In this episode of Alex & Annie: The Real Women of Vacation Rentals, AirDNA's Chief Economist Jamie Lane joins us to explain what the data is revealing about the 2025 market. With demand softening among budget travelers, international bookings pulling back, and economic uncertainty on the rise, Jamie helps make sense of the mixed signals facing STR professionals today.Jamie also shares how AirDNA is evolving to better support property managers in this climate, with new tools, smarter comps, and deeper forecasting capabilities. Whether you're adjusting pricing strategies, watching booking windows shrink, or wondering what's next for growth, this conversation provides the clarity and context you need.Key Topics Discussed:1️⃣ Are we in a travel recession? Early signals from airline and STR data2️⃣ Why summer 2025 bookings are slower, especially in budget and urban segments3️⃣ Hotels gaining share in cities as STR growth is restricted by regulation4️⃣ Supply growth slows across most markets and what that means for operators5️⃣ Signs of guests trading down, shortening trips, and delaying decisions6️⃣ The impact of fewer Canadian and European travelers this year7️⃣ Airbnb's urban inventory problem and the increasing presence of hotels on OTAsJamie also shares his outlook for the rest of 2025 and why, despite current challenges, the long-term growth of short-term rentals remains strong.Connect with Jamie:LinkedIn: https://www.linkedin.com/in/jamiehlane/Mention "Alex & Annie" when you sign up with Boom to get 50% off your onboarding fee and 1 month FREE: ⁠⁠⁠https://www.boomnow.com/⁠⁠#vacationrentals #travelrecession #shorttermrentals

In this episode, Ben Wolff, co-founder and developer of Onera and CEO of Oasi, shares insights on the structural barriers holding back innovation in the hospitality industry and how unique properties are outperforming others in the market.Connect with Ben:LinkedInTwitter (@UniqueStaysGuy)Instagram (@IAmBenWolff)NewsletterSee our other episodes with Ben: Why Most Hotels Fail at Social Media (And How to Get It Right) How We're Scaling Innovation and Investment from Short-Term Rentals to Hotels A few more resources: If you're new to Hospitality Daily, start here. You can send me a message here with questions, comments, or guest suggestions If you want to get my summary and actionable insights from each episode delivered to your inbox each day, subscribe here for free. Follow Hospitality Daily and join the conversation on YouTube, LinkedIn, and Instagram. If you want to advertise on Hospitality Daily, here are the ways we can work together. If you found this episode interesting or helpful, send it to someone on your team so you can turn the ideas into action and benefit your business and the people you serve! Music for this show is produced by Clay Bassford of Bespoke Sound: Music Identity Design for Hospitality Brands

What if your weekly calendar was designed to fit your life—and not the other way around? In this inspiring episode, I sit down with Melissa Mondzelewski—a powerhouse mom of four, Airbnb host, short-term rental entrepreneur, and master of intentional living. Melissa pulls back the curtain on how she structures her “ideal week”—a flexible, evolving framework that helps her stay grounded in what matters most while managing a thriving Airbnb business, motherhood, and personal growth. From themed workdays to long-term vision planning, Melissa shares the systems and routines that keep her short-term rental business running smoothly without sacrificing her sanity. We dive into how she balances hosting, handles disruptions in her Airbnb operations, and embraces delegation as a key to growth. This isn't about rigid schedules or perfection—it's about creating a week that aligns with your life, your business goals, and your values. Whether you're managing one vacation rental or scaling a portfolio of Airbnbs, Melissa's approach will inspire you to rethink what balance and productivity look like as a short-term rental host. If you're ready for more alignment, more ease, and more clarity in how you run your Airbnb or short-term rental business (and your life!), this episode is your permission slip to build success your way. HIGHLIGHTS AND KEY POINTS: [01:09] A short introduction about our guest Melissa Mondzelewski and how she got started in the world of short-term rentals [03:44] Melissa talks about how balancing motherhood and business requires constant adjustment and shares that her “ideal week” evolves regularly [05:03] Melissa's ideal week concept and how it evolved from managing a busy family schedule to setting firm personal and family priorities first [08:29] Melissa share her experience and approach to navigating disruptions and prioritizing family over business during a crisis [11:27] Melissa share her weekly planning tools and strategies for family and business balance [16:31] Melissa's advice for non-planners highlights how planning helps manage stress and progress toward goals [23:19] How Melissa manages guest communications for her four properties and the importance of delegation [29:03] How  Melissa structures her workweek to keep herself on track and productive [32:56] Melissa shares how she structures her workdays, incorporating creative time and flexibility [36:48] How Melissa handles the unpredictability of her schedule and the importance of avoiding overwhelm [42:12] The lightning round Golden Nuggets: “There are certain things that I just won't compromise on. I won't compromise on my kids schedule. I won't compromise on my workouts. I won't compromise, doing family stuff. So when I create my ideal week, all of that goes into my week first, then I put the business stuff in.” “I think you really need to have that five year vision of where you want to go. And if you don't have that five year vision, you're never going to get there.” “I think those priorities come front and center, and they're always there to remind us, hey, I have a business. I love my business, but my family comes first.” “Be true to yourself and your values; find your why and just stick to it.” “Talk to yourself like you would your best friend.” This episode is brought to you by StayFi — the easiest way to grow your direct bookings! ⁠http://stayfi.com/STRSisterhood⁠ Use the code “SISTERHOOD” at checkout for 50% off your first 3 months. Let's Connect! Website: https://www.stylishstay.com/ Enjoyed the show? Subscribe, Rate, Review, Like, and Share!

In this episode, Ben Wolff, co-founder and developer of Onera and CEO of Oasi, shares insights on the evolving expectations of today's travelers and how creating immersive, participatory experiences can lead to deeper emotional connections and memorable guest experiences.View Ben's post on LinkedIn about thisConnect with Ben:LinkedInTwitter (@UniqueStaysGuy)Instagram (@IAmBenWolff)NewsletterSee our other episodes with Ben: Why Most Hotels Fail at Social Media (And How to Get It Right) How We're Scaling Innovation and Investment from Short-Term Rentals to Hotels A few more resources: If you're new to Hospitality Daily, start here. You can send me a message here with questions, comments, or guest suggestions If you want to get my summary and actionable insights from each episode delivered to your inbox each day, subscribe here for free. Follow Hospitality Daily and join the conversation on YouTube, LinkedIn, and Instagram. If you want to advertise on Hospitality Daily, here are the ways we can work together. If you found this episode interesting or helpful, send it to someone on your team so you can turn the ideas into action and benefit your business and the people you serve! Music for this show is produced by Clay Bassford of Bespoke Sound: Music Identity Design for Hospitality Brands

In this episode, Ben Wolff, co-founder and developer of Onera and CEO of Oasi, shares his journey of discovering creativity in hotel development and why he views it as an artistic act, not just a business endeavor.Connect with Ben:LinkedInTwitter (@UniqueStaysGuy)Instagram (@IAmBenWolff)NewsletterSee our other episodes with Ben: Why Most Hotels Fail at Social Media (And How to Get It Right) How We're Scaling Innovation and Investment from Short-Term Rentals to Hotels A few more resources: If you're new to Hospitality Daily, start here. You can send me a message here with questions, comments, or guest suggestions If you want to get my summary and actionable insights from each episode delivered to your inbox each day, subscribe here for free. Follow Hospitality Daily and join the conversation on YouTube, LinkedIn, and Instagram. If you want to advertise on Hospitality Daily, here are the ways we can work together. If you found this episode interesting or helpful, send it to someone on your team so you can turn the ideas into action and benefit your business and the people you serve! Music for this show is produced by Clay Bassford of Bespoke Sound: Music Identity Design for Hospitality Brands

In this episode of Good Morning Hospitality, Wil Slickers, Michael Goldin, and Brandreth Canaley are joined by Phocuswright's Madeline List to unpack the newly released “U.S. Short-Term Rentals 2025: Guest Attitudes and Decision Making” report. We explore the shifting expectations of today's travelers, especially the under-35 segment that's showing growing skepticism toward the STR category. Madeline walks us through why travelers are comparing rentals and hotels more than ever, the true impact of bad PR on booking decisions, and what the STR sector must do to compete on service, professionalism, and design. Whether you're an operator, host, or vendor, this conversation is a must-listen to understand the next phase of guest decision-making in short-term rentals. ---- ⁠⁠⁠⁠⁠⁠⁠⁠Good Morning Hospitality⁠⁠⁠⁠⁠⁠⁠⁠ is part of the ⁠⁠⁠⁠⁠⁠⁠⁠Hospitality.FM⁠⁠⁠⁠⁠⁠⁠⁠ Multi-Media Network and is a Hospitality.FM Original The hospitality industry is constantly growing, changing, and innovating! This podcast brings you the top news and topics from industry experts across different hospitality fields. Good Morning Hospitality publishes three thirty-minute weekly episodes: every Monday and Wednesday at 7 a.m. PST / 10 a.m. EST and every Tuesday at 8 a.m. CET for our European and UK-focused content. Make sure to tune in during our live show on our ⁠⁠⁠⁠⁠⁠⁠⁠LinkedIn page⁠⁠⁠⁠⁠⁠⁠⁠ or ⁠⁠⁠⁠⁠⁠⁠⁠YouTube⁠⁠⁠⁠⁠⁠⁠⁠ every week and join the conversation live! Explore everything Good Morning Hospitality has to offer: • Well & Good Morning Coffee: Enjoy our signature roast—⁠⁠⁠⁠⁠⁠⁠⁠order here!⁠⁠⁠⁠⁠⁠⁠⁠ • Retreats: Join us at one of our exclusive retreats—learn more and register your interest ⁠⁠⁠⁠⁠⁠⁠⁠here!⁠⁠⁠⁠⁠⁠⁠⁠ • Episodes & More: Find all episodes and additional info at ⁠⁠⁠⁠⁠⁠⁠⁠GoodMorningHospitality.com⁠⁠⁠⁠⁠⁠⁠⁠ Thank you to all of the Hospitality.FM Partners that help make this show possible. If you have any press you want to be covered during the show, email us at goodmorning@hospitality.fm Learn more about your ad choices. Visit megaphone.fm/adchoices

A once-profitable approach is now facing oversaturation, rising costs, and tighter regulations. Investors should reassess before committing to outdated strategies.Get access to our real estate community, coaching, courses, and events at Wealthy University https://www.wealthyuniversity.com/Join our FREE community, weekly calls, and bible studies for Christian entrepreneurs and business people. https://www.wealthykingdom.com/ If you want to level up, text me at 725-527-7783!--- About Ryan Pineda: Ryan Pineda has been in the real estate industry since 2010 and has invested in over $100,000,000 of real estate. He has completed over 700 flips and wholesales, and he owns over 650 rental units. As an entrepreneur, he has founded seven different businesses that have generated 7-8 figures of revenue. Ryan has amassed over 2 million followers on social media and has generat...

In this episode, Ben Wolff, co-founder and developer of Onera and CEO of Oasi, shares his insights on staying resilient in the hospitality industry and the importance of recovery for long-term success.Connect with Ben:LinkedInTwitter (@UniqueStaysGuy)Instagram (@IAmBenWolff)NewsletterSee our other episodes with Ben: Why Most Hotels Fail at Social Media (And How to Get It Right) How We're Scaling Innovation and Investment from Short-Term Rentals to Hotels A few more resources: If you're new to Hospitality Daily, start here. You can send me a message here with questions, comments, or guest suggestions If you want to get my summary and actionable insights from each episode delivered to your inbox each day, subscribe here for free. Follow Hospitality Daily and join the conversation on YouTube, LinkedIn, and Instagram. If you want to advertise on Hospitality Daily, here are the ways we can work together. If you found this episode interesting or helpful, send it to someone on your team so you can turn the ideas into action and benefit your business and the people you serve! Music for this show is produced by Clay Bassford of Bespoke Sound: Music Identity Design for Hospitality Brands

In this episode, Ben Wolff, co-founder and developer of Onera and CEO of Oasi, shares how his team has proven that social media can drive real results for traditional hotels and the surprising attribution gap they uncovered by just asking guests how they found them.Connect with Ben:LinkedInTwitter (@UniqueStaysGuy)Instagram (@IAmBenWolff)NewsletterSee our earlier episode with Ben: How We're Scaling Innovation and Investment from Short-Term Rentals to Hotels A few more resources: If you're new to Hospitality Daily, start here. You can send me a message here with questions, comments, or guest suggestions If you want to get my summary and actionable insights from each episode delivered to your inbox each day, subscribe here for free. Follow Hospitality Daily and join the conversation on YouTube, LinkedIn, and Instagram. If you want to advertise on Hospitality Daily, here are the ways we can work together. If you found this episode interesting or helpful, send it to someone on your team so you can turn the ideas into action and benefit your business and the people you serve! Music for this show is produced by Clay Bassford of Bespoke Sound: Music Identity Design for Hospitality Brands

In this episode of the Real Estate Education and Investing Podcast, Erin Spradlin and James Carlson, tackle two critical issues affecting property investors: Furnished Finder's new "worry-free waiver" program and a concerning short-term rental ban in Woodland Park, Colorado. They analyze Furnished Finder's deposit alternative which charges hosts $60-80 monthly for protection up to $3,500 in damages, highlighting numerous limitations including cosmetic damage exclusions and comparing it unfavorably to traditional landlord protection policies. The hosts argue that security deposits serve not only as protection but also as an essential tenant screening tool—if prospective tenants cannot afford a deposit, they likely cannot afford the rental itself. The second segment examines Woodland Park's citizen-led ballot measure that completely banned STRs without grandfathering existing permit holders. What's particularly alarming is a recent court ruling suggesting property owners have little chance of successful legal challenge, setting a potentially dangerous precedent unlike previous regulatory changes in Colorado communities which typically preserved existing STR permits. Throughout the episode, the hosts emphasize the importance of working with knowledgeable professionals who understand local STR laws and can help investors navigate the increasingly complex regulatory landscape. Contact James: james@jamescarlsonRE.com Contact Erin: Erin@erinspradlin.com For more information visit: https://www.jamescarlsonre.com/ https://www.erinandjamesrealestate.com/

Have feedback or a topic you want to hear about, let us know by sending us a direct message!Welcome back to another exciting episode of KarWell Chronicles!

In this episode of Uncontested Investing,we dive into the booming world of short-term rentals (STRs) and explore how savvy investors are leveraging platforms like Airbnb and Vrbo to maximize cash flow, diversify geographically, and reduce risk.   From vacation properties to workforce housing, the hosts break down how investors of all sizes can scale intelligently by choosing the right locations, designing a memorable guest experience, and taking advantage of seasonal markets.    Whether you're new to STRs or looking to grow your portfolio, this episode is full of practical advice and fresh ideas to expand your impact in the rental space.   Key Talking Points of the Episode   00:00 Introduction 01:05 How STRs can earn 2–3x the monthly income vs. long-term rentals 02:07 Avoiding competitive metro markets through location flexibility 03:25 Underrated markets: Wyoming, Buffalo, Acadia, and snowmobile trails 05:21 Lower maintenance burden for STRs vs. traditional property managers 07:22 Guest experience: why it matters and how to differentiate your STR 08:23 Becoming a Superhost: reputation, reviews, and responsiveness 09:45 What is PadSplit? 10:38 Targeting the workforce for your STRs 12:31 The value of guest feedback: guestbooks, quick fixes, seasonal upgrades 14:00 How smart home tech can help improve your STR 16:14 How shorter tenancies reduce strain and increase adaptability   Quotables   “With a short-term rental, you can actually generate two to three times more income than a long-term lease.”   “You decide your level of involvement—from doing it yourself to having a full-service team handle it all.”   “Diversification isn't just about property type. It's about location, lease length, and tenant type.”   Links   RCN Capital https://www.rcncapital.com/podcast https://www.instagram.com/rcn_capital/ info@rcncapital.com   REI INK https://rei-ink.com/

In this episode of the AIA podcast, host Alex Perny welcomes Lamè Kinikini, the founder and CEO of Elk Ridge Management, to discuss the short-term rental market, particularly in Florida and other vacation destinations.Subscribe to our YouTube channel and join our growing community for new videos every week.If you are interested in being a podcast guest speaker or have questions, contact us at ⁠⁠⁠⁠⁠Podcast@AdvantaIRA.com.⁠⁠⁠⁠⁠⁠⁠⁠Learn more about our guest, Lamè Kinikini:https://www.linkedin.com/in/hailamekinikini/Learn more about Advanta IRA: https://www.AdvantaIRA.com/ The Alternative Investing Advantage is brought to you by Advanta IRA.Advanta IRA does not offer investment, tax, or legal advice, nor do we endorse any products, investments, or companies that provide such advice and/or investments. This includes any investments promoted or discussed during the podcast as neither Advanta IRA nor its employees, have reviewed or vetted any investments, persons, or companies that may discuss their services during this podcast.  All parties are strongly encouraged to perform their own due diligence and consult with the appropriate professional(s) before entering into any type of investment.

Send us a message!Alex & Annie bring you behind the scenes at VRNation 2025 to explore direct booking strategies, industry growth, tech innovation, and the evolving role of associations in vacation rentals.Recorded live in Austin, Texas, this special bonus episode captures real-time insights from the conference floor. Alex & Annie had on-the-spot conversations with some of the industry's most influential voices and rising innovators to unpack the real story behind what's shaping the vacation rental space today.In true Alex & Annie fashion, they also asked some of the conference participants one powerful question: “In one word, what's the biggest problem in vacation rentals?” The answers reveal a lot about where the industry stands and where it's headed.Featuring interviews with:Heidie Henriksen – Executive Director of VRNationOrlie Benjamin – Founder of LasohDylan Bozarth – General Manager of 30A EscapesTera Lorimer – Founder of Luxury Getaways and VRNation Board MemberHeather Van Wie – Founder of Cottages on the Key and VRNation Board MemberNicholas Wegener & Roy Collins – Founders of SendSquaredAnne Gardner – Executive Director at VRMAWhether you were at VRNation or following the buzz afterward, this episode captures the energy and insight straight from Austin.Mention "Alex & Annie" when you sign up with Boom to get 50% off your onboarding fee and 1 month FREE: ⁠⁠⁠https://www.boomnow.com/⁠⁠ Get $50 credit and $0 onboarding fee when you sign up for Beyond, the leading dynamic pricing tool for vacation rentals: http://beyondpricing.info/alexandannie #vacationrentals #Shorttermrentals #VRNation2025

Welcome to Dentist Money Two Cents, a look at the latest financial and economic news from the past week.
 On this episode, Matt, Jake, and Rabih cover new economic data topics like GDP, unemployment, and inflation and explain why fears of a recession may be overblown. They also dive into short-term rentals—a popular tax strategy that allows owners to offset losses against active income. And finally, they emphasize the importance of focusing on long-term asset ownership over short-term market moves. Book a free consultation with a CFP® advisor who only works with dentists. Get an objective financial assessment and learn how Dentist Advisors can help you live your rich life.

In this episode of the Real Estate Pros podcast, Stephen Schmidt interviews Jessica Fischer, an expert in short-term rentals and property management. Jessica shares her personal journey from facing financial hardships to successfully managing properties for busy professionals. She discusses the importance of technology, systems, and processes in property management, as well as the value of learning from mistakes and building strong relationships with service providers. Jessica emphasizes the significance of coaching and masterminds in her growth and offers advice for those looking to enter the property management field.   Professional Real Estate Investors - How we can help you: Investor Fuel Mastermind:  Learn more about the Investor Fuel Mastermind, including 100% deal financing, massive discounts from vendors and sponsors you're already using, our world class community of over 150 members, and SO much more here: http://www.investorfuel.com/apply   Investor Machine Marketing Partnership:  Are you looking for consistent, high quality lead generation? Investor Machine is America's #1 lead generation service professional investors. Investor Machine provides true ‘white glove' support to help you build the perfect marketing plan, then we'll execute it for you…talking and working together on an ongoing basis to help you hit YOUR goals! Learn more here: http://www.investormachine.com   Coaching with Mike Hambright:  Interested in 1 on 1 coaching with Mike Hambright? Mike coaches entrepreneurs looking to level up, build coaching or service based businesses (Mike runs multiple 7 and 8 figure a year businesses), building a coaching program and more. Learn more here: https://investorfuel.com/coachingwithmike   Attend a Vacation/Mastermind Retreat with Mike Hambright: Interested in joining a “mini-mastermind” with Mike and his private clients on an upcoming “Retreat”, either at locations like Cabo San Lucas, Napa, Park City ski trip, Yellowstone, or even at Mike's East Texas “Big H Ranch”? Learn more here: http://www.investorfuel.com/retreat   Property Insurance: Join the largest and most investor friendly property insurance provider in 2 minutes. Free to join, and insure all your flips and rentals within minutes! There is NO easier insurance provider on the planet (turn insurance on or off in 1 minute without talking to anyone!), and there's no 15-30% agent mark up through this platform!  Register here: https://myinvestorinsurance.com/   New Real Estate Investors - How we can work together: Investor Fuel Club (Coaching and Deal Partner Community): Looking to kickstart your real estate investing career? Join our one of a kind Coaching Community, Investor Fuel Club, where you'll get trained by some of the best real estate investors in America, and partner with them on deals! You don't need $ for deals…we'll partner with you and hold your hand along the way! Learn More here: http://www.investorfuel.com/club   —--------------------

In this powerful solo episode, Heather Bayer reflects on one of the most fundamental - and often overlooked - questions in the short-term rental space: What kind of leader are you? Through years of podcast interviews and her own journey managing STR properties, Heather unpacks the evolving nature of leadership and how it uniquely manifests in the vacation rental industry. From traditional leadership styles to emotionally intelligent approaches, she guides us through a wide spectrum of frameworks, weaving in personal stories and rich insights from some of the most inspiring voices in the business. This episode highlights the remarkable leadership archetypes shaping our space - from the spiritual and creative to the cultural and transformational. Whether you're managing a team, growing a portfolio, or simply aiming to lead with more purpose, this episode is a must-listen. Revolutionize Your Employee Onboarding with THRIVE Essentials: Faster Training, Stronger Teams, Better Results! Discover how THRIVE Essentials accelerates onboarding for new property management staff, boosting performance and reducing turnover. >> THRIVE Essentials Are you listening to this podcast on the move? Get to the show notes here: https://www.vacationrentalformula.com/VRS609

Send us a message!In this episode of Alex & Annie: The Real Women of Vacation Rentals, we're joined by Ian Ackland, Managing Director of the Americas at Booking.com, for a candid look at how one of the world's largest travel platforms is evolving its approach to better serve property managers.With more than 30 years in the travel industry and over a decade at Booking.com, Ian shares how the company is shifting from being just a distribution channel to becoming a true partner for vacation rental professionals. From reimagining payment systems and investing in connectivity, to expanding their U.S. market presence and leveraging AI, Ian walks us through the strategy behind Booking.com's efforts to reduce friction and drive more value for hosts at every stage of growth.Whether you're a large enterprise or just getting started, this episode is packed with practical insights on how to work smarter, tap into new guest demand, and build a more effective tech stack through stronger partnerships.Key Topics Discussed:1️⃣ Ian's background in hospitality and why hosting is personal to him2️⃣ The evolution of Booking.com's vacation rental strategy3️⃣ Why connectivity partners like NextPax play a key role in host success4️⃣ How Booking.com is supporting both enterprise and mid-sized property managers5️⃣ What makes listings convert: content, rate plans, and smart distribution6️⃣ The redesign of their payment system to solve real host pain points7️⃣ How generative AI is helping streamline guest communication8️⃣ Loyalty, trust, and the value of high-frequency guests9️⃣ The tools and resources Booking.com offers to support property managers at scaleConnect with Ian:LinkedIn: https://www.linkedin.com/in/ian-ackland-1b3b444/ Mention "Alex & Annie" when you sign up with Boom to get 50% off your onboarding fee and 1 month FREE: ⁠⁠⁠https://www.boomnow.com/⁠⁠ Get $50 credit and $0 onboarding fee when you sign up for Beyond, the leading dynamic pricing tool for vacation rentals: http://beyondpricing.info/alexandannie #VacationRentals #ShortTermRentals #OTA

One asset class within commercial real estate that many people don't think about is luxury Short-Term Rentals. Houses that cost between $2 and $5 million typically rent for $500-$1,500 per night and generate $200,000 or even more per year in revenue, comparable to small apartment buildings. Investors can use these properties themselves, they enjoy the cash flow, plus they benefit from capital preservation and appreciation. Stephen Petasky, Founder and CEO of the Luxus Group, manages high-end Short-Term Rentals, develops luxury condo communities in partnership with The Four Seasons, and refurbishes centuries old farmhouses in Tuscany and converts them into luxury rentals. 

What's the real reason most people can't qualify for real estate professional tax status? In this episode, Brandon Hall breaks down one of the most misunderstood areas of tax law for real estate investors: Real Estate Professional Status (REPS). He explains what it really takes to meet the IRS requirements, why many investors get it wrong, and how short-term rentals provide a unique workaround to unlock non-passive tax losses. Brandon shares actionable insights about what kinds of hours count, how to keep an audit-proof time log, and the tax-saving power of partial asset dispositions. Whether you're a full-time employee or a hands-on investor, this episode offers practical takeaways on reducing your tax burden through smart structuring and documentation.     [00:01 - 04:12] Why REPS Isn't What You Think It Is The importance of understanding the IRS's specific definition of real estate professional status Why full-time employees are generally disqualified from REPS—even if they work in real estate The significance of your spouse's time if you file jointly and they are more available to qualify   [04:13 - 08:34] What Hours Actually Count Toward REPS What kinds of work count toward REPS hours—and which ones don't Why education, travel, and investor-related tasks often don't qualify The importance of maintaining a detailed and credible time log   [08:35 - 12:48] Short-Term Rentals: The REPS Loophole Without the Status How short-term rentals avoid the REPS rules entirely under tax code Section 469 What the “seven-day rule” is and why it matters How material participation alone is enough to make short-term rental losses non-passive   [12:49 - 17:00] 3 Tests for Material Participation Explanation of the three most common IRS tests for material participation Why documentation is key to proving participation, especially with vendors Strategies to meet the 500-hour threshold or qualify under the 100-hour rule   [17:01 - 22:25] The Most Overlooked Tax Deduction: Partial Asset Dispositions How replacing property components like roofs and appliances can create immediate write-offs Why this strategy reduces both current taxes and future depreciation recapture How to apply this method consistently for long-term tax savings     Connect with Andy:   LinkedIn: https://www.linkedin.com/in/andymcmullen/       Key Quotes:   “People treat real estate professional status as a tax loophole—but it's not. It's a heavily litigated area and the IRS expects solid documentation.” – Brandon Hall   “You don't have to be a real estate professional to make short-term rental losses non-passive. You just have to materially participate.” – Brandon Hall     Visit sponsorcloud.io/contact today and unlock $2,000 of free services exclusively for REI Rocks community members! Get automated syndication and investor relationship management tools to save time and money. Mention your part of the REI Rocks community for exclusive offers. Help make affordable, low-cost education summits possible. Check out Sponsor Cloud today!   LEAVE A REVIEW + help someone who wants to explode their business growth by sharing this episode.

Are you curious about what it's like to own short-term rentals with your partner? In today's episode, Ali chats with her husband Caleb about their best Airbnb renter stories, short-term rental experiences, and Caleb's upcoming birthday plans. Time-stamps:Caleb's favorite birthday memories (1:36)What Caleb says Ali does for work (4:06)What really is Ali's name? (5:48)Does Caleb listen to the podcast? (8:36)Reflecting on living in Kentucky (11:30)Brand Strategy Framework Course (21:10)Best Airbnb stories (22:30)Invest, Sell, or Live? (29:17)Caleb's advice to be the best in your brand and market (34:39)Mentioned in This Episode:Episode 3 A Wedding Venue Venture: podcasts.apple.com/us/podcast/the-best-laid-brandBrand Strategy Framework Course: brandandmarket.thrivecart.com/brand-strategyWebsite: brandandmarket.coInstagram: instagram.com/brandandmarket.co

We're excited to welcome Dana Lynch to the Hospitable Hosts podcast. Dana is a short-term rental host based in Austin, Texas, with properties in Osage Beach, Missouri. Dana started her hosting journey while working full-time as a real estate closer—learning the ins and outs of the business by listening to podcasts during her 2.5-hour commute to work. Initially, she relied on a property manager but quickly realized that communication was lacking, pushing her to take control of her business with the help of automation tools like Hospitable. Now, she's on a mission to scale her portfolio, aiming to add seven more properties this year.Sleep easy, host confidently with Hospitable. Automate your guest messages, sync your calendar across booking channels, and protect yourself from bad direct booking guests.Sign up today at hospitable.com/podcast and get 25% off your bill for 3 months.

Are you unknowingly leaving thousands of dollars on the table with your Airbnb or short-term rental listings? In this episode, I sit down with short-term rental revenue management experts Jillian Heilman and Karin Leung to uncover how small pricing and listing tweaks can unlock big profits for Airbnb hosts. We dive deep into key strategies every short-term rental owner needs to know—like optimizing booking windows, avoiding common Airbnb pricing mistakes, and eliminating revenue leaks you may not even realize are happening. Jillian and Karin reveal how they use dynamic pricing tools, create high-performing seasonal rate profiles, and why a reactive pricing approach is causing many Airbnb hosts to miss out on bookings and revenue. But it's not just about pricing—listing optimization plays a massive role in increasing your Airbnb or short-term rental property's visibility and profitability. We break down the power of photo placement, keyword-rich descriptions, and how to position your short-term rental to attract high-value guests without slashing your nightly rate. If you're an Airbnb host or short-term rental investor who's ready to increase occupancy, boost average nightly rates, and grow your bottom line—this episode is packed with actionable strategies and insider tips to help you master Airbnb revenue management and become a more profitable host. HIGHLIGHTS AND KEY POINTS: [00:59] A short introduction about our guests Jillian Heilmann and Karin Leung, and how they got into managing revenue for owners and hosts of short term rentals [06:05] What is a booking window or lead time, and why is it important for owners and hosts to pay attention to it [08:16] Why people haven't paid attention to booking window in the past and how booking window impacts pricing strategy [10:09] The strategic use of discounts based on where you are within your average booking window [14:18] Jllian and Karin's thoughts on how often should someone continue to inch their prices down [19:20] The seasonal profile approach and why they are so important to have at a more granular level than just the four seasons of the year [21:14] How much time do hosts anticipate it will take to set up 35 seasonal profiles [23:45] What is the best approach or recommendation to pricing for those far-out bookings [29:08] The declining daily rates in saturated short-term rental markets and how to monitor them using market data tools [31:11] Staying competitive in saturated markets without dropping prices [33:44] The importance of comprehensive listing optimization and captions for each photo to enhance the guest experience [36:24] Karin and Jillian's words of wisdom for hosts to get started and get comfortable with managing their revenue [39:59] The value of outsourcing tasks in your business that you don't enjoy to focus on what you excel at and love doing [41:42] The lightning round Golden Nuggets: “It's really important that you understand where your market is and where people are and how people are booking within that lead time. So if your booking window has really shortened, you've got to make sure that your pricing is right in line.” “If a week or two goes by and you don't have any activity, then you know that something needs to happen in your pricing to move the needle. So the longer you wait, you know the more negative impact can happen.” “Keep your prices competitive enough that if you were to get that booking a year out or three months out, you're still happy with it.” “I would not recommend utilizing any pricing optimization through any of the OTAs, because a lot of times they're pricing for the benefit of getting as many bookings as possible, which means, not necessarily maximum revenue.” “Think about what you enjoy doing and the value of your time leading your business.” Let's Connect! Website: stepbystepbnb.com Enjoyed the show? Subscribe, Rate, Review, Like, and Share!

Today, we're revisiting short-term rentals, specifically the City's proposed updates to its regulations.Whether you're a homeowner, a renter, a downtown business owner, or someone just trying to understand what these changes could mean for your neighborhood, we've got you covered.We connect with Development Services Director Jeremy Pagan to break down what's happening with the City's Zoning Ordinance of Short Term Rentals—updates that could expand where short-term rentals are allowed, particularly in the heart of our city: the Downtown Mixed-Use District.We'll talk about:What's prompting these changes?What do the proposed updates actually do?How is the City balancing economic growth with community concerns?We will also discuss community feedback, housing affordability, and the broader context of how short-term rentals fit into Redding's vision for the future and its tourism strategy. So stick around as Jeremy walks us through it.Read the transcript >>Learn more about Short Term Rentals in Redding >>Contact the City of Redding Podcast Team Email us at podcast@cityofredding.org Connect with us on Facebook, Twitter and Instagram Visit the City of Redding website Love the podcast? The best way to spread the word is to rate and review!

Ready to save $10k-$50k in taxes this year? Book a call here:► https://taxstrategy365.com/pod-appIn this episode, I break down one of the most powerful tax strategies available to real estate investors: the short-term rental (STR) tax loophole. I explain how investors who don't qualify as real estate professionals can still use rental losses to offset W-2 and active business income—if they meet specific IRS requirements. I outline the two major tests you must pass (average stay and material participation), how to document them properly, and the massive tax savings this can unlock. If you want to pay less tax, accelerate your real estate goals, and avoid costly mistakes, this episode is your blueprint.Want me to answer your real estate questions? Come to my next Ask Me Anything Q&A:► https://taxstrategy365.com/pod-amaLet's connect!► Instagram: https://www.instagram.com/ryanbakkecpa/► LinkedIn: https://www.linkedin.com/in/ryanbakkecpa/► Twitter: https://twitter.com/RyanBakkeCPA► Facebook: https://www.facebook.com/ryanbakkecpa► TikTok: https://www.tiktok.com/@ryanbakkecpa⁠*None of this is meant to be specific investment advice, it's for entertainment purposes only.

Maximize Your Short-Term Rental Profits: Expert Tips from Dan Rivers | REIGN Podcast with Jen Josey   Join Jen Josey, hostess of the Real Estate Investor Growth Network (REIGN), as she talks with Dan Rivers, Owner of SynergyStays, in this informative podcast episode. Dan shares his extensive experience in real estate, focusing on the importance of having legal backup, identifying profitable short-term rental markets, and optimizing revenue management. Learn from Dan's strategies and real-world insights to make your short-term rental a top performer. Don't miss this episode for essential tips and actionable advice to take your real estate investing to the next level! Listen now!   00:00 Introduction to REIGN 01:00 Today's Topic: The Power of Legal Backup 03:38 Guest Introduction: Dan Rivers 04:55 Dan Rivers' Journey into Real Estate 06:50 The Importance of Networking in Real Estate 09:34 Short-Term Rentals: Key Factors for Success 16:59 Revenue Management and Optimization 25:06 Experience and Masterminds in Revenue Management 27:05 Advice for New Real Estate Investors 28:18 Overcoming Life-Changing Challenges 30:08 Finding Your Why and Personal Goals 33:51 Setting and Achieving Financial Goals 36:55 What Makes Dan Rivers a Badass 43:49 Conclusion and Final Thoughts   Social Media Links: @danrivers_rcg for IG and FB Website: www.synergystayslocal.com   To learn more about Jen Josey, visit www.TheRealJenJosey.com To join REIGN, visit www.REIGNmastermind.com Stuff Jen Josey Loves: https://www.reignmastermind.com/resources Buy Jen Josey's Book: From Beginner to Badass: https://a.co/d/bstKlby

In this episode, we break down Shannon Sharpe's jaw-dropping $50 million lawsuit. Then, we tackle the return of student loan repayments and the ripple effects hitting millions of Americans. We'll also explore the escalating tariff battles between the U.S. and global powers, and how the dismantling of the Department of Education could reshape the country's future. Plus, in a bombshell revelation, China pulls back the curtain on luxury brands exposing shocking truths about manufacturing and the illusion of "high-end" quality. No fluff. No spin. Just the raw reality you need to know. Enjoy!!!If you'd like to grab some merch, canvas prints for your home or office, or see the full length video from this episode please visit dopevision.com. Follow me on ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Instagram⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠, ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Facebook⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠, ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Twitter⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠, @dopevisionsf. Send me an email of someone you'd like to hear on the podcast at ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠dopevisionsf@gmail.com⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ Also, please join the Dope Vision Club at patreon.com/dopevision for early access to content and a behind the scene look of some of my episodes.While you're listening don't forget to hit the subscribe button and comment on the podcast as well my ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠YouTube channel⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ and turn on the notifications so you'll be notified each and every time I drop a new episode. Thanks for listening and remember it's collaboration over competition. Enjoy!When you're ready to create your beautiful website to promote your business don't forget about Squarespace and to support THE DOPE VISION EXPERIENCE PODCAST⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠CLICK HERE⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ to save 10% off your first subscription to your Squarespace website and use my promo code PARTNER10 at checkout⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠CLICK HERE⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ to get 30-day Free Premium Access to Printify use promo code ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠dope vision⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠If you'd like to schedule a quick 15 min meeting with me please ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Click Here⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Click Here⁠⁠⁠⁠⁠ to checkout my Short Term Rental property

Joining me on this episode of Living Off Rentals is someone who's been an athlete, Navy veteran, cyber engineer, and now, a short-term rental investor. Stylianos “Steve” Kalamaras is a fighter in every sense of the word. A former boxer turned real estate investor, he's built an impressive short-term rental portfolio that brings in solid cash flow to rival his tech salary.  He is also a member of my First Vacation Rental Investment Blueprint Program, and since joining, he's closed on a handful of standout deals, including one where he converted a two-unit into a three-unit property that's already generating over $3,000 in monthly cash flow. In this episode, we dive into how each chapter of his life, from sports to military service to tech, has contributed to his success as an investor. We also talk about the lessons he learned through the deals he's closed, working with contractors, and why a good house hack might just be the best financial decision you can make. Enjoy the episode! Key Takeaways: [00:00] Introducing Stylianos Kalamaras and his background [02:24] Before getting into real estate [05:28] Skills as a professional athlete and military that played a part in his success as a real estate investor [08:18] His first deal and first full rental [15:42] Launching a new property [17:31] What is the BRRRR strategy? [21:07] The bare minimum in considering a deal [25:23} The biggest risk in business is a knowledge gap [31:21] Getting the kids involved  [32:02] "Get started as soon as you can." [37:26] Connect with Stylianos Kalamaras Guest Links: Instagram: https://www.instagram.com/thegoldengreek  Show Links: Living Off Rentals YouTube Channel – youtube.com/c/LivingOffRentals  Living Off Rentals YouTube Podcast Channel - youtube.com/c/LivingOffRentalsPodcast  Living Off Rentals Facebook Group – facebook.com/groups/livingoffrentals  Living Off Rentals Website – https://www.livingoffrentals.com/  Living Off Rentals Instagram – instagram.com/livingoffrentals  Living Off Rentals TikTok – tiktok.com/@livingoffrentals 

Over the last decade, Madeleine has built 3 successful companies and a community of over 2 million people.She is the founder of MHM Luxury Properties, Madeleine Raiford-Holland (MRH) Education, and Moderately High Maintenance Luxury Properties.Her mission is to inspire anyone who feels chained by golden handcuffs to step out of their comfort zone and build their own massively profitable short term rental business.Madeleine helps aspiring short term rental investors and established operators, start or optimize short term rental businesses that focus on elevated guest experiences and automated systems. Her goal is not only financial freedom but also time freedom to live life on your terms.To know more about Madeleine visit her website: www.madeleineraifordholland.comWatch The Luxe and The Short of It Podcast Episode 4 with Lyndsay Dowd Here:https://podcasts.apple.com/us/podcast/04-lyndsay-dowd-bouncing-back-better-finding-opportunity/id1792946314?i=1000689220717This episode is sponsored by: The Outlier ProjectWebsite: https://www.theoutlierproject.live/LinkedIn: @theoutlierproject

Do you know the value of interior design for your short-term rental? In today's episode, Ali chats with designer Morgan Wise of Morgan Kay Interiors. Morgan shares her advice for rental owners who are looking to make the best impression of their space, balance functionality and aesthetic, and keep up with design trends while on a budget. Time-stamps:Introducing Morgan Wise (1:10)The virtual interior design experience (5:31)Virtual versus in-person design (9:09)Crafting the first impression of your short-term rental (11:56)Using interior design to reinforce brand identity (16:45)Airbnb (21:00)Budgeting for interior design (22:00)Balancing functionality and aesthetic (31:06)Trends in the short-term rental industry (34:55)Morgan's key piece of advice (37:49)Mentioned in This Episode:Morgan Wise Website: morgankayinteriors.comMorgan Wise Instagram: instagram.com/morgankayinteriorsAirbnb: brandandmarket.co/airbnbWebsite: brandandmarket.coInstagram: instagram.com/brandandmarket.co

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In this episode of The Real State, we uncover the truth about short-term rentals with Christina Robinson, real estate entrepreneur, educator, and self-made superhost. From house-hacking her first property while working a 9-to-5, to managing a portfolio of vacation rentals in South Florida, Christina walks us through the highs, lows, and total myths of the short-term rental game. We dig into: Why short-term rentals are not as passive as they seem The difference between long-term and vacation rental income Self-managing vs. using property managers (and why it's not just about the money) How technology, systems, and building the right team helped her escape the 9-to-5 Why mindset, location, and hustle matter more than hype Whether you're dreaming of Airbnb riches or just curious about getting into real estate, this conversation breaks down what it really takes to win in the short-term rental world. Timestamps00:00 – Intro + Why this episode matters03:05 – Christina's origin story: From finance to first-time buyer11:20 – House-hacking before it had a name15:45 – Short sales, student tenants, and the path to passive income21:15 – The Airbnb algorithm: what every host should know25:35 – Vacation rentals vs. long-term rentals: what's the real payoff?33:00 – The truth about self-managing (and burnout)40:20 – Tech, tools, and what makes a 5-star stay48:10 – The 3 C's: Checklist, CRM, and Capacity52:40 – Final thoughts + Key takeaways

In this episode of the no BS podcast, we explore the intersection of co-living and short-term rentals with guests Cliff Johnson and Atticus LeBlanc. The discussion delves into the benefits of co-living, the flexibility and financial empowerment it offers, and its role in addressing affordable housing issues. Atticus shares his journey into creating PadSplit, including his experiences with real estate investment and the evolution of the co-living model. Cliff adds insights from his extensive background in vacation rentals and highlights how co-living can complement the short-term rental market. The episode also covers regulatory challenges, the potential for commercial property conversions, and the community support PadSplit provides to both investors and residents.PadSplit https://www.padsplit.com/Episode Highlights:00:00 Introduction to the No BS Podcast00:57 Diving into Co-Living and Short-Term Rentals02:31 Atticus LeBlanc's Journey and Vision07:19 The Birth of PadSplit13:10 PadSplit's Impact and Future20:41 Challenges and Misconceptions21:33 Regulatory Clarifications and Affordable Housing24:15 Addressing Misconceptions About Co-Living26:15 Making Co-Living Easy and Effective28:19 Community and Peer Support in Co-Living34:31 Scaling and Future Prospects of PadSplit35:29 Innovative Housing Solutions and Conversions40:34 Empowerment and Community Impact41:39 Final Thoughts and Call to Action

Send us a message!In this episode of Alex & Annie: The Real Women of Vacation Rentals, we sit down with Boogie Wittenburg, the new CEO of TravelNet Solutions, makers of Track PMS. With a background in mission-critical technology powering global brands, Boogie brings a fresh, people-first perspective to the vacation rental tech space.Building on the strong foundation laid by the company's founders, Boogie shares how he's guiding TravelNet Solutions into its next chapter — one that balances continuity with innovation. With a renewed focus on culture, customer experience, and thoughtful technology, Boogie brings a clear vision for scaling both the platform and the people behind it.Key Topics Discussed:1️⃣Boogie's journey from global tech to short-term rentals2️⃣Why servant leadership is at the core of his management style3️⃣How TravelNet Solutions is improving customer support and answering the phone again (yes, really!)4️⃣The rollout of the new Owner Mobile App and its impact on retention5️⃣Track's approach to product development: build, buy, or partner6️⃣The role of AI in scaling support and internal operations7️⃣What true team engagement looks like—and why it mattersBoogie also shares a powerful reflection on legacy, leadership, and building a company where employees, customers, and innovation thrive together.Whether you're a property manager, tech vendor, or industry leader, this episode offers valuable insight into what it takes to scale a software company without losing sight of people.Connect with Boogie:LinkedIn: https://www.linkedin.com/in/oduswittenburg/Website: https://tnsinc.com/Get $50 credit and $0 onboarding fee when you sign up for Beyond, the leading dynamic pricing tool for vacation rentals: http://beyondpricing.info/alexandannieReady to take your operations to the next level? Visit https://tnsinc.com/podcasts-alex-and-annie/  to learn more.#VacationRentals  #TrackPMS  #ServantLeadership

Hey friends + welcome to another episode on the Your Brand of Beautiful Podcast! In case you're new, this is the podcast where we chat with women who have created their own unique version of a beautiful life, in hopes that their stories, life experiences, or insider tips might inspire others to do the same. This week, I got the chance to chat with Madeleine Raiford Holland about going from a Kitchen Table Breaking Point to a 7-Figure Family. Madeleine is the founder + CEO of MHM Luxury Properties, a 7 figure boutique Short Term Rental company. She's also the founder & CEO of MRH Education with a thriving community she helps to build their STR business empires. If you're anything like me, stories about women who hit their breaking point + decide to do something about it intrigues you. And also, the idea of investing in short term or vacation rental properties piques your interest! If so, you'll want to listen to this episode. Madeleine is sharing about the very moment everything changed for her: sitting at her kitchen table, after a hard week, with a 6 month old baby + a husband who was equally as filled with exhaustion as she was. Then, how from that moment, she got to where she is today -- owning 16+ properties + a 7-figure investment STR company. Madeleine also shares… About times when she flopped or struggled getting started in business. How to tell if you're a right fit for the STR biz + if it's a right fit for you. And how becoming big givers was a huge turning point in she + her husband's business. I hope you love this conversation and learn from it the way I did! For more info on Madeleine: https://www.madeleineraifordholland.com/ Follow Madeleine on Instagram: https://www.instagram.com/madeleineraifordholland Check out Madeleine's Rental Properties: https://mhmluxuryproperties.com/ About Your Brand of Beautiful Host, Bailie White: Bailie White is a motivational speaker with nearly 10 years of entrepreneurial experience and a heart for serving, motivating, and encouraging women. After starting and scaling her first business — a luxury travel agency with a team of 15 women, a celebrity clientele, and multi-millions of dollars in annual sales — she sold the business after realizing what she once thought was her dream, didn't fully align with the woman she wanted to become. Today, Bailie is the host of the Your Brand of Beautiful Podcast (debuting on Apple's Top Charts) and a published author and speaker. Bailie facilitates workshops and delivers keynote speeches to college women, young professionals, and mamapreneurs. Bailie teaches these women how to Stop Being Busy, Quiet The Noise, and Start Being Them — she teaches them how to become Their Own Brand of Beautiful. Bailie has been featured in media outlets like Buzzfeed and Forbes, but is most proud of her title as ‘wife' and ‘mom' to her two small children. Bailie lives with her family on the outskirts of Savannah, Georgia.   LET'S CONNECT! For speaking, event, or podcasting collabs, email: hey@bailiewhite.com Connect on Instagram: https://www.instagram.com/heybailiewhite/ Visit Website: https://www.bailiewhite.com Weekly Newsletter: https://www.bailiewhite.com/newsletter

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Today's Flash Back Friday episode is from #660 that originally aired on Oct. 23, 2023. Join us as Alex Jarbo, the visionary founder and CEO of Sargon Investments, takes us on a journey into the world of short-term rental resort development. With an MBA in real estate development, a distinguished history as a Marine, and a prominent presence in the real estate investing community, Alex shares his expertise in a special episode. Discover how he masterfully manages his current and upcoming luxury short-term vacation rentals, including an exciting treehouse project. Dive into the world of short-term rentals with Alex Jarbo on the YouTube channel "Alex Builds," and gain insights from the industry's best.   Quote:  “I hate it when I talk to someone and I'm like, “Oh what business are you in or what type of real estate they're in and they say, “I'm in AirBnBs.” That's the wrong answer. What I say is I'm in vacation rentals, short term rentals, or what I started saying in the last six months is, “I'm in hospitality.”  “Every single one of your guests is an influencer, because they have their own following.“   Highlights:  7:50: Post-COVID, what is the revenue like in short term rentals?  12:30: From an owner's perspective  19:40: Treehouse community project  24:00: Amenities people expect  27:30: How to navigate uncertainties   Connect with Alex: alexjarbo.com  Openatlas.investments  https://www.youtube.com/@AlexBuilds1    Recommended Resources: Accredited Investors, you're invited to Join the Cashflow Investor Club to learn how you can partner with Kevin Bupp on current and upcoming opportunities to create passive cash flow and build wealth. Join the Club! If you're a high net worth investor with capital to deploy in the next 12 months and you want to build passive income and wealth with a trusted partner, go to InvestWithKB.com for opportunities to invest in real estate projects alongside Kevin and his team.  Looking for the ultimate guide to passive investing? Grab a copy of my latest book, The Cash Flow Investor at KevinBupp.com.  Tap into a wealth of free information on Commercial Real Estate Investing by listening to past podcast episodes at KevinBupp.com/Podcast.