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Town board also finalizing rental law A survey of Philipstown residents found little support for a tax on home purchases that would fund the purchase of open spaces, wildlife habitats and other natural resources, according to Town Board member Nat Prentice. The Trust for Public Land funded a three-week poll to "test out support" for a Community Preservation Fund, said Prentice at the board's July 9 meeting. "The results, from 307 responses, "suggested that the voters would not support a community preservation fund at this time, citing mostly cost-of-living reasons," he said. "All they heard was tax." Ted Warren, the public policy manager for the Hudson Highlands Land Trust, told the board last year that a tax of up to 2 percent would apply to the portion of a property purchase exceeding the median price for home sales in Putnam County, which was $580,000 in 2025. For example, a house that sold for $700,000 would be taxed on $120,000 of the sale. Philipstown took an initial step to create the fund, which would need voter approval, in August 2023 by adopting a Community Conservation Plan. But Supervisor John Van Tassel said at the time that the idea of a new tax during the pandemic "did not settle well" with the board. In addition, said Warren, another survey of Philipstown residents conducted by the Trust for Public Land showed "a lot of ambivalence" about a fund. Under the Hudson Valley Community Preservation Act, a state law that grants municipalities in Putnam and Westchester counties the authority to establish conservation funds, the money would be administered by a five- or seven-member advisory board composed of volunteer residents. The Town Board on Wednesday (July 15) approved a $95,050 bid by Cemco Water & Wastewater Specialists to buy and install water meters at properties in the Garrison's Landing Water District. The other bids were $276,400 and $320,200. The previous meters failed in 1999 after the district's source "went from a ground/surface-fed system to a well-fed system" and the pressure increased, Van Tassel said. Philipstown officials said the town did not have the funds to buy meters until the board authorized borrowing $500,000 last year to cover capital upgrades. To repay the loan, the town added a $2,500 levy to the tax bills of property owners within the district, including those who are not connected but use wells. Once the meters are installed, the town will calculate a per-gallon usage fee for properties that use the water, Van Tassel said. Philipstown is finalizing regulations governing short-term rentals, such as those offered on Airbnb. The town is expected to introduce a local law at its Aug. 6 meeting and schedule a public hearing. At the suggestion of Board Member Ned Rauch, the board agreed on Wednesday to add language clarifying that the limit of two people per sleeping area includes an exception for parents who want an infant or small child in their room. Prentice suggested the town eliminate an inspection requirement because STRs are "a very market-driven, self-regulating industry where bad operators don't survive." He noted that the owners of about 100 of the roughly 140 STRs in Beacon have not registered, as mandated by the city. "You could get people to attest that they are keeping in line with code and that their insurance covers them," said Prentice. "If you made it easy on them, they'd all sign up." But Van Tassel said he "would never rely on a homeowner" to ensure an STR unit is safe. In the past, he has cited a 2024 fire at an unregistered Airbnb in Salt Point that killed a Cape Cod woman and her 1-year-old daughter. The owners of the unit, which did not have smoke detectors despite an attestation that it did, were charged with manslaughter. "My feeling would be to send a building inspector," said Van Tassel. The Town Board presented a proclamation to Haldane High School student Allegra Clementson, who organized a food-scrap recycling program in the district as part of a pilot pro...
How do you turn what feels like an “ordinary” property into a brand that guests connect with, remember, and actively choose over everyone else's? In this episode, I'm joined by branding and marketing strategist Ali Haney. We're unpacking how she transitioned from a long-term rental disaster into remote short-term rental management across multiple states, eventually blending her photography background with her hospitality experience to help hosts build true brand equity.We talk about:Flipping perceived property weaknesses into powerful market differentiators, like turning a Gatlinburg cabin's lack of internet into an intentional, off-the-grid romantic reset complete with analog experiences.Building a foundational brand strategy from scratch by defining core messaging pillars, identifying a hyper-specific guest avatar, and establishing values that serve as concrete criteria for hiring and firing your team.Utilizing ChatGPT and AirDNA as a market research "cheat code" to analyze competitor specs, summarize guest review trends, and spot high-impact amenities missing in your local market.Designing property features around guest origin data, such as installing an EV charger at a Catskills rental specifically to attract higher-income, eco-conscious travelers driving up from the city.Executing a deep property rebrand that goes beyond a logo tweak, using your brand strategy as a daily filter for social content, listing updates, and team briefs to eliminate decision fatigue.Ali pulls back the curtain on how to use your brand strategy as the literal backbone of your guest experience and long-term business scaling. You'll hear how to shift your mindset to view marketing as structured testing and learning rather than a verdict on your worth, allowing you to "do it scared" and out-position your competition.If you are a short-term rental / Airbnb host wondering how to stop competing on price alone and start engineering an unforgettable hospitality brand that commands premium rates, this conversation is your blueprint. Get ready to learn how to drop perfectionism and start leading your life and business with intention.HIGHLIGHTS AND KEY POINTS:[01:07] A short introduction about our guest Ali Haney, and how she got into the world of short-term rentals[03:12] Ali talks about using branding strategy to move beyond photography and create marketing that connects with ideal guests [06:50] Ali explains how defining a property's personality and turning perceived limitations into unique selling points creates a memorable brand that attracts the right guests [09:32] How identifying a property's natural differentiators helps build a stronger and more memorable brand[10:49] Ali shares how operators can decide between separate property brands or a unified brand strategy when managing multiple listings across different markets[12:39] Ali outlines portfolio-level values as the foundation for aligning multiple property brands while preserving each listing's individuality [15:40] Ali defines brand strategy as the foundational framework that aligns mission, guest targeting, differentiation, and messaging to guide every part of a short-term rental business[21:14] How the core value of excellence creates clear operational boundaries and simplifies decision-making across hospitality and property management[24:33] Ali highlights branding as a profit-driven strategy that turns one-time OTA guests into repeat direct bookings while improving long-term ROI[27:51] Ali frames rebranding as a full strategic reset that goes beyond visuals to ensure alignment between guest targeting, design, and business goals [30:16] Ali distinguishes between legacy brands and STR assets while outlining when rebranding makes sense and how to use guest data to guide the decision [32:52] How competitor and review analysis can uncover actionable differentiators that directly shape STR brand strategy and guest experience design[34:56] Ali reframes STR marketing as a data-driven cycle of testing and learning, separating performance outcomes from personal identity to support better decision-making[37:31] Ali shares how short-term rental owners can begin building a brand strategy by using existing performance data and evaluating properties through a differentiation-first mindset[40:07] The lightning round Golden Nuggets:“You're giving the house essentially a personality, so that people can start to feel like they know that property before they even step foot into it.”“We took what she thought was a weakness and instead tailored the entire property's brand and made it their superpower.”“If we don't have a strategy that we want to enact within our business and we just build pretty things on top of it, it's probably going to fall down at some point.”“Create an experience that people want to return to, because it's much easier to nurture a client or a guest that already trusts you, versus having to consistently acquire new ones.”“If we just take a small step each and every day, and we do that scared, that is still a huge amount of progress over six months time, nine months time, 12 months time.”Let's Connect: Website : https://brandandmarket.co/Instagram : https://www.instagram.com/brandandmarket.co/Enjoyed the show? 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CONTACT MIKE & KEVIN:https://www.revotaxpayer.com/WEBINAR LINK:https://shawnmoore.clickfunnels.com/optiniyvvg89sWant 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-15a5caa687b7FOLLOW US:https://www.instagram.com/vodysseyshawnmoorehttps://www.facebook.com/vodysseyshawnmoore/https://www.linkedin.com/company/str-financial-freedomhttps://www.tiktok.com/@vodysseyshawnmooreCONTACT US:support@vodyssey.comChapters00:00:00 Intro00:00:23 Meet the guests and discuss the importance of strategy00:00:58 Timing and planning for end-of-year asset purchases00:01:27 Debunking myths about bonus depreciation qualification00:02:24 Active participation and managing short-term rentals00:03:19 Material participation and management roles00:04:50 Active involvement without managing day-to-day operations00:06:14 Qualifying as an active participant in a trader business00:12:56 Understanding the $512,000 limit and tax law changes00:14:20 Limits for high W-2 earners and carryforward strategies00:16:19 Using bonus depreciation and cost segregation effectively00:20:57 Purchase price allocation and its importance in real estate deals00:24:02 Passive vs. active rental properties and tax implications00:27:21 Market environment and negotiating strategies00:28:15 The importance of proactive planning and expert guidance00:29:43 Final thoughts on tax strategies and wealth building
What if your “unique” short-term rental is actually invisible… and costing you thousands?Steph Weber joins Kenny Bedwell to unpack the brutal disconnect between what most STR and boutique hotel owners think is a brand, and what truly drives guest loyalty, market differentiation, and higher ADR. From confusing “luxury” with actual value to the real reason guests rebook through Airbnb, you'll learn why strong branding is the difference between getting buried by algorithms and building a hospitality business guests remember and seek out.Fail to master these steps, and you'll keep paying the Airbnb tax forever. Listen now to learn exclusive, field-tested strategies for transforming how guests see and book your property. Brand clarity isn't optional anymore. If you want real direct bookings and a sellable business, this is your playbook.Timestamped Highlights00:29 – Why calling your STR “luxury” is killing your results09:48 – The instant trust hacks big platforms use (and how you can, too)12:53 – The hidden branding mistake costing you direct bookings16:52 – How “avatar clarity” instantly changes your marketing game23:19 – Real-world examples: When does every property need its own brand?29:16 – The blueprint for turning your portfolio into a premium, sellable asset33:50 – The power move that gets guests coming back—without discounts36:21 – The critical mistake most hosts make with guest experienceAbout The GuestSteph Weber is the founder of The Weber Co., a top-tier branding and marketing agency specializing in hospitality businesses. Leveraging deep experience from both the fashion industry and high-performing influencer partnerships, she's helped entrepreneurs scale to seven figures, reimagine their STR brands, and create properties guests return to year after year.
Are you quietly losing thousands by ignoring your rental's brand?In this punchy solo episode, Kenny Bedwell cuts through the noise and exposes why branding is not just logos or pretty fonts. Right now, as Airbnb changes the rules again and hosts are questioning their dependence on big platforms, building your own brand is your only edge.You'll get a direct, step-by-step breakdown of Kenny's three-phase branding model from picking the right property name (and why it matters) to advanced tactics that skyrocket direct bookings and multiply revenue. Whether you own one STR or ten, if you're not branding now, you're falling behind in a market that's professionalizing fast.If you miss this, you're gambling with your margins. Quit playing catch-up… Listen now for the most practical, numbers-backed strategies nobody else is showing you.Timestamped Highlights00:05 – The single branding mindset shift most hosts get wrong01:32 – The myth that only luxury or big properties need branding02:24 – The brutal truth about Airbnb's changes and your risk05:09 – A centuries-old branding move that still works now06:32 – The one thing every host MUST do for phase one branding09:02 – Kenny's three unfiltered phases for building a real brand10:33 – The unexpected revenue multiplier hidden in guest avatars14:26 – What happens when you actually brand around guest desiresMentioned ResourcesFiverrChatGPTClaudeMarriottAirbnbVRBOImportant LinksWant us to find the deals for you? https://strinsights.comGet Top Markers for STRs (2025) - https://rebrand.ly/28b1dfInstagram – @kenny_bedwellYouTube – Cash Flow PositiveLinkedIn – Kenneth BedwellCash Flow Positive is an original podcast hosted by Kenny Bedwell. Brought to you by STR Insights. Production and editing by Podcast Your Brand.
WEBINAR LINK:https://shawnmoore.clickfunnels.com/optiniyvvg89sWant 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-15a5caa687b7FOLLOW US:https://www.instagram.com/vodysseyshawnmoorehttps://www.facebook.com/vodysseyshawnmoore/https://www.linkedin.com/company/str-financial-freedomhttps://www.tiktok.com/@vodysseyshawnmooreCONTACT US:support@vodyssey.comPROPERTIES:https://www.experiencetennessee.us/propertiesChapters00:00:00 Intro00:04:47 Transitioning to Short-Term Rentals00:08:01 Navigating Challenges in Short-Term Rentals00:11:17 Learning and Adapting in the Market00:15:26 Revamping Properties for Target Audience00:19:48 Self-Managing Properties: Pros and Cons00:22:55 Building a Regional Portfolio00:25:45 Favorite Properties and Their Stories00:28:24 Advice for New Investors
AI is changing the way travelers discover short-term rentals—and it's happening faster than most hosts realize.In this episode, Mark Lumpkin sits down with Gil Chan, Founder & CEO of Crafted Stays, to discuss how AI search, direct bookings, and modern website strategies are reshaping the future of the STR industry.Gil explains why relying solely on OTAs is becoming increasingly risky, how AI platforms like ChatGPT and Gemini are influencing guest booking behavior, and what hosts can do today to position their properties for the next generation of search. He also shares how Crafted Stays is helping operators build high-converting direct booking websites that are optimized for both traditional SEO and AI-powered discovery.Whether you're managing one property or hundreds, this conversation is packed with practical insights to help you future-proof your business.In this episode, you'll learn: Why AI is changing how guests search for vacation rentals How direct bookings compound over time while OTA bookings stay transactional The importance of identifying your ideal guest avatar What SEO, AEO, and GEO mean—and why they matter How to build a website that's ready for the future of travel search Why hospitality and guest experience still matter more than ever If you're serious about growing your direct bookings and staying ahead of where the industry is headed, this is an episode you won't want to miss. __Episode Sponsored By:STR SearchSTR Search is the industry leading property finder service. They've helped investors acquire over 215 profitable STRs across the US. If you'd like the data professionals to help you find your next STR, reach out to STRsearch.com
Are your Airbnb investments sabotaging your wealth before you even realize it?In this episode, Kenny Bedwell delivers a blunt reality check for tax-savvy short-term rental investors chasing bonus depreciation and “easy” write-offs. He exposes the #1 mistake even experienced buyers keep repeating: letting potential tax savings override every other investing principle. You'll hear why treating your STR like a “break-even” tax play leads to wasted time, lost money, and painful exit decisions.Speaker Link Format makes the case for focusing on cash flow and fundamentals first, then using tax benefits as the cherry, not the sundae. If you let the tax tail wag the investment dog, you're putting your financial future at risk.Act now or keep falling for the hype. This episode delivers not just advice, but a clear framework to avoid regret and finally build real, generational wealth that lasts.Timestamped Highlights00:22 – The single mindset mistake elite investors keep repeating03:47 – Why “breaking even” is the last thing you want to say06:16 – The dangerous difference between tax savings and ROI08:17 – The strategic moat that top buyers always look for12:11 – How land value can quietly erase your tax benefits15:45 – The 5 cash flow essentials every Airbnb buyer overlooks17:44 – The states and markets with the best tax-saving upside18:13 – The cash flow vs. tax savings showdown—real numbers, real stakes22:56 – The practical formula to banish buyer's remorse for goodMentioned ResourcesBonus depreciation (Congressional legislation)Real Estate Professional Status (IRS definition)Important LinksWant us to find the deals for you? https://strinsights.com Get Top Markers for STRs (2025) - https://rebrand.ly/28b1df Instagram – @kenny_bedwellYouTube – Cash Flow PositiveLinkedIn – Kenneth BedwellCash Flow Positive is an original podcast hosted by Kenny Bedwell. Brought to you by STR Insights. Production and editing by Podcast Your Brand.
Most short-term rental owners assume Airbnb and Vrbo handle all of their lodging taxes.They don't.In this episode, Mark Lumpkin sits down with Julie Banting Rogers from Avalara to uncover one of the biggest blind spots in the STR industry: lodging tax compliance.Julie explains why thousands of hosts and property managers unknowingly fall out of compliance, how platform-collected taxes actually work, and why failing to file the right paperwork can result in massive penalties, interest, or even liens on your properties.In this episode, you'll learn: How Airbnb and Vrbo handle lodging taxes (and what they don't do) The difference between state, county, and local lodging taxes Why many STR operators unknowingly owe back taxes The costly mistakes property managers make How to stay compliant without spending hours on paperwork What every STR owner should know before buying their next property If you own, manage, or are planning to invest in short-term rentals, this episode could save you from an expensive mistake.__Episode Sponsored By:STR SearchSTR Search is the industry leading property finder service. They've helped investors acquire over 215 profitable STRs across the US. If you'd like the data professionals to help you find your next STR, reach out to STRsearch.com
Are you truly in control of the demand for your short-term rentals, or have you quietly outsourced it to the OTAs without even realizing it? Relying solely on large platforms means you don't actually own your customer base; the hosts who master true demand generation are the ones who will thrive in the next phase of our industry.In this episode, I sit down with Amber Knight, the founder of Bookings Cloud and a seasoned veteran of vacation rental heavyweights like Vacasa, Rented, Inhabit, and LiveRez. We're unpacking what it really means to build a direct guest acquisition engine for your properties and step into true ownership of your business.We talk about:How public booking platforms control the narrative using your listing content, and why reclaiming that control is vital for long-term business survival.Why a beautiful direct booking website means nothing if it breaks guest trust by kicking them over to an unbranded, clunky PMS engine at the final step.Utilizing true paid social ads, not just boosted posts, to feed rich property data into algorithms that match your stay with the perfect guest.Why clicks on Meta can be pennies compared to dollars on Google, why you should never put pricing in your ads, and how to automate property-level campaigns at scale.Clear guidance on when to focus strictly on guest communication versus when your portfolio size justifies a full website investment.We pull back the curtain on the messy reality of data tracking and attribution in a world of privacy laws and GA4. You'll hear why diversifying your booking sources isn't just a quick fix for the low season, but a long-game retirement strategy that compounds over time and builds a business with real enterprise value.If you are ready to move from hoping bookings show up to intentionally creating your own demand, this conversation will give you the playbook. Get ready to stop letting other platforms dictate your revenue and start engineering your own growth.HIGHLIGHTS AND KEY POINTS:[01:03] A short introduction about our guests Amber Knight, and journey from growing up around vacation rentals to building a career focused on strengthening local hospitality businesses and destination communities[04:12] Amber reflects on how intentionally building a life and business through consistent daily actions creates opportunities that once seemed out of reach[06:10] Amber explains how owning guest demand has become a critical competitive advantage as short-term rental operators can no longer rely solely on OTAs to drive bookings[10:58] Amber emphasizes that successful demand generation starts with building trust and creating a direct-booking experience that converts website visitors into guests[18:24] How demand generation moves beyond simply having a trusted website and focuses on actively driving qualified traffic to it [21:07] Amber breaks down Meta advertising as a layered system—from organic content to fully automated, property-level ads—designed to turn raw property data into targeted demand at scale[28:15] Amber explains when paid social becomes viable for STR operators based on ad spend consistency and unit economics versus OTA commissions[30:40] What are the effective Meta ads for STRs rely on high-intent, property-specific visuals and structured data feeding rather than pricing-driven creatives[33:35] Amber explains that attribution is imperfect and long-term direct booking growth should be measured through influence, pacing, and consistent investment rather than immediate ROAS results[42:16] The lightning round Golden Nuggets:“It's really empowering that we each have the ability to build a business around a life that we love.”“If every day you make another step to get to the life you want, the career you want, in the place that you want, eventually you'll get there.”“A business that is sellable does not require the owner to be in the day to day.”“You can't change what happens to you, you can change how you respond to it.”Let's Connect:Website : www.bookingscloud.com Instagram : https://www.linkedin.com/company/bookingscloud/ Email : aknight@bookingscloud.comProudly sponsored by PriceLabsEnjoyed the show? Subscribe, Rate, Review, Like, and Share!
What if the only thing standing between you and rapid portfolio growth isn't money, but mindset and strategy?Kenny Bedwell drills into the raw realities of leveraging Other People's Money (OPM) to explode your short-term rental business, exposing what actually works and what will quietly kill your progress. Whether you have time but no capital, or capital with no time, he details the only partnership structures that protect you, your investors, and your reputation in this cutthroat market.If you're tired of inching forward one property at a time, this episode is your unfair advantage. Miss this, and you risk years of wasted effort or worse, destroyed trust. Listen now to claim your spot among the 5% who do deals with true confidence and never look back. This level of transparency and actionable detail is only here.Timestamped Highlights00:54 – The brutal reality of scaling fast with limited capital03:07 – Why asking for investor money scares most, and how to get over it06:16 – Top 20% status: Why simply owning ONE STR puts you way ahead09:19 – How investors decide who to trust (it's not just about the deal)10:59 – The game-changing 3-part partnership framework revealed13:31 – The equity mistake 90% of new executors make16:43 – The unheard-of way to split tax savings and keep everyone happy18:54 – The critical conversation most partnerships skip (at their peril)20:28 – Why time or money isn't your issue—your circle isMentioned ResourcesAirbnb506B & 506C syndications“Analysis paralysis”Passive investingImportant LinksWant us to find the deals for you? https://strinsights.com Get Top Markers for STRs (2025) - https://rebrand.ly/28b1df Instagram – @kenny_bedwellYouTube – Cash Flow PositiveLinkedIn – Kenneth BedwellCash Flow Positive is an original podcast hosted by Kenny Bedwell. Brought to you by STR Insights. Production and editing by Podcast Your Brand.
What does it take to stay relevant in the short-term rental industry for nearly three decades?In this episode, Mark Lumpkin sits down with Michael St. Pierre, a hospitality veteran with 28 years of experience spanning vacation rentals, luxury resorts, revenue management, owner acquisition, and some of the industry's most recognized brands.Michael shares how he got started in the business, the lessons he learned from working in Hawaii and with Hyatt-affiliated properties, and why hospitality is still the foundation of long-term success in a rapidly changing industry.They also discuss:• What investors can learn from luxury hotel brands• Why relationships are one of the most valuable assets in business• The evolution of revenue management and dynamic pricing• How AI is changing the vacation rental landscape• The importance of building systems, standards, and memorable guest experiences• What the next generation of STR operators needs to focus onWhether you manage one property or hundreds, this conversation is packed with practical insights on hospitality, growth, and building a sustainable business in the vacation rental industry.Connect with Michael St. Pierre on LinkedIn to learn more about revenue management, owner acquisition, and the future of short-term rentals.
Is your short-term rental truly set up to cash flow, or are you just hoping the market will do the heavy lifting for you? Most hosts look at dynamic pricing as a "set it and forget it" tool, but real revenue strategy requires getting behind the wheel of your data.In this episode, I sit down with Colorado host and revenue strategist Melissa Stewart, the founder of Rev Collective. Melissa scaled from zero to four high-performing mountain cabins in under two years by combining a value-add investment blueprint with a highly intentional, data-driven revenue management strategy.We talk about:Buying distressed mountain properties for maximum negotiating power, doing a full gut rehab to build equity, and leveraging a smart refi to roll into the next deal.Moving past simple bulleted descriptions to craft narrative-driven listing copy that makes guests feel like they are walking through a storybook.What a "healthy" MPI looks like, how to recognize if you are underpriced or overpriced, and why treating dynamic pricing tools like autopilot is a massive mistake.Designing interior and exterior spaces with a strict guest avatar in mind—from luxury robes and sound machines to curated coffee and tea stations.Shifting your mindset around money as energy, shedding old financial stories, and building wealth that creates real opportunities for other women in hospitality.Melissa pulls back the curtain on how her background in accounting and data analysis gave her a unique edge in the short-term rental market. You'll hear how she bridges the gap between high-end hospitality and cold, hard data, and how she built her company specifically to empower women hosts who love the guest experience but feel overwhelmed by numbers and tech.If you are ready to stop guessing on your pricing, master your local pacing, and inject serious intention into your operations, this conversation will completely redefine your approach to revenue. Get ready to stop relying on market luck and start commanding the rates your property deserves.HIGHLIGHTS AND KEY POINTS:[01:14] A short introduction about our guests Melissa Stewart and shared her journey from exiting a business to getting into the short-term rental industry[03:06] Melissa reflects on how a background in real estate and a desire for lifestyle-driven wealth building led her and her husband into the world of short-term rentals[05:30] How strategic investing, leveraging equity, and taking bold action helped Melissa scale from one short-term rental property to four in a relatively short time[07:36] Melissa and I dive into how taking on distressed properties, embracing renovation challenges, and viewing obstacles as opportunities helped accelerate equity growth and STR success[12:31] How embracing problems, adapting quickly, and treating short-term rental hosting as a constant problem-solving business is essential for long-term success [14:36] Melissa unpacks how creating intentional five-star guest experiences, strategic branding, and emotionally driven listings became the foundation of cash-flowing STR properties at the top of the market[21:10] Melissa highlights how overlooking listing strategy after investing heavily in a property is a common mistake, and how emotional storytelling and optimization are key to turning beautiful homes into booked STRs[24:54] How STR success depends not just on design, but on operations, pricing, and listing strategy working together to drive higher nightly rates and long-term profitability[28:08] Melissa shares how her passion for entrepreneurship, wealth building, and supporting women in business ultimately led her to launch The Rev Collective[34:16] Melissa's emphasis on active revenue management as a critical profit driver that requires strategy, oversight, and expertise beyond Pricelabs[38:15] Melissa's guidance on using listing optimization, market pacing, and key revenue metrics to make smarter pricing decisions and improve booking performance [43:23] The lightning round Golden Nuggets:“Know your obstacles. That way when they come, they're opportunities.”“We cannot leave any stone unturned when it comes to positioning ourselves for getting that booking, these guests have so many options in front of them on the OTAs.”“If you're not operating well, your reviews are not going to be what you need them to be, and you're going to fall to your competition in the marketing.”“Stick to doing things that you're good at and delegate the rest.”“If your ultimate goal is to cash flow to build wealth in this real estate, you know, gig that you've got going, if that's your goal, then revenue management should be your top priority when it comes to running your business, because that's how you make your moneyLet's Connect:Website : www.revcollective.co Instagram : https://www.instagram.com/itsmelissastewart Enjoyed the show? Subscribe, Rate, Review, Like, and Share!
What if the three things holding back your short-term rental revenue are hiding in plain sight?Kenny Bedwell, data-driven investor and STR educator, breaks down the amenities most investors miss, ones that are scientifically proven to spike your bookings and cash flow fast. Forget the gimmicks and “guru” advice. In this brutally practical episode, you'll hear real numbers, tactical breakdowns, and the overlooked upgrades that have delivered six-figure jumps for Kenny Bedwell and his clients.You will miss out on the bookings your comps are snatching up right now if you ignore these simple moves. Listen in and get the honest playbook for immediate results. No fluff. No hype. Just the uncommon upgrades that separate winning properties from the pack, only on Cash Flow Positive.Timestamped Highlights00:15 – The three revenue-slaying amenities every STR owner misses01:46 – Are you making this six-figure mistake with your amenities?04:39 – How a heated pool turned winter dead zones into year-round cash08:17 – Container pool case study. From $150K to $244K in a single year10:21 – The no-glamour upgrade that quietly adds $15K to your bottom line13:16 – Why full bathrooms are the untapped ROI secret in most markets20:08 – The lighting hack delivering 500 percent returns (not string lights)25:12 – One color tweak to your property lighting that boosts revenue 30 percentMentioned ResourcesAirbnbChatGPTImportant LinksWant us to find the deals for you? https://strinsights.com Get Top Markers for STRs (2025) - https://rebrand.ly/28b1df Instagram – @kenny_bedwellYouTube – Cash Flow PositiveLinkedIn – Kenneth BedwellCash Flow Positive is an original podcast hosted by Kenny Bedwell. Brought to you by STR Insights. Production and editing by Podcast Your Brand.
The Appraisal Update - the official podcast of Appraiser eLearning
In today's episode, Bryan Reynolds sits down with Bill Waltenbaugh, Chief Appraiser at Nationwide Appraisal Network (NAN), about something that's been a hot topic for a while now in the appraisal space: short-term rentals. How do you appraise them? What do the lenders expect? What do the AMCs expect? Does anyone expect the same thing?Bill shares his wealth of knowledge on this topic, walks us through NAN's resources for appraisers, and talks about what the future of appraising STRs will look like. Don't miss this insightful conversation.
His wife said something to him that he'll never forget."I would let every business burn to the ground if it meant that when it's nighttime and on weekends, we could spend it as a family."Dave Menapace didn't argue. Didn't defend himself.He sat with it. And then he changed everything.In this episode, E sits down with STR Secrets coach and Five Star Co-Host founderDave Menapace — on his birthday — for a raw, unfiltered look at four years ofbuilding, burning down, and rebuilding a short-term rental management companythe right way.Dave left corporate healthcare in April 2022 with two STRs and a vision.Four years later, he's managing 58 properties. He signed number 58 this morning.But the path there? It looked nothing like what he planned.In this episode:→ The "seven streams vs. seven jobs" mistake that keeps most operators brokeand burned out — and how Dave finally broke the cycle→ How he started Five Star Co-Host over from scratch after realizinghe'd built it wrong the first time→ The $100K IRA withdrawal that gave him the team he needed to grow→ Why he went from 30 properties to 58 in just 5 months — and the threeobsessions that made it possible→ The $80,000 trust account crisis that hit in September 2025 — and whyhis response to it doubled the business→ What it actually takes to build a management company worth $100M(and why Dave believes it's just a choice)This is not a highlight reel.It's the version of the story most people are too scared to tell.Want to connect with Dave? Find him on Instagram: @dave_menapaceJoin the community: STR Secrets Facebook GroupFree 6-step course: level.strsecrets.com/pc-bookTimestamps: 00:00 - "Seven streams of income is not seven jobs"08:07 - Leaving corporate, WealthCon, and the birth of Five Star Co-Host15:48 - The Miami pool moment Kim told E: "my husband is doing a million things"32:21 - The most important thing Kim ever said to Dave35:45 - The three obsessions that unlocked 30 to 58 properties in 5 months48:17 - The $80,000 crisis and what focus does under pressure
His wife said something to him that he'll never forget."I would let every business burn to the ground if it meant that when it's nighttime and on weekends, we could spend it as a family."Dave Menapace didn't argue. Didn't defend himself.He sat with it. And then he changed everything.In this episode, E sits down with STR Secrets coach and Five Star Co-Host founderDave Menapace — on his birthday — for a raw, unfiltered look at four years ofbuilding, burning down, and rebuilding a short-term rental management companythe right way.Dave left corporate healthcare in April 2022 with two STRs and a vision.Four years later, he's managing 58 properties. He signed number 58 this morning.But the path there? It looked nothing like what he planned.In this episode:→ The "seven streams vs. seven jobs" mistake that keeps most operators brokeand burned out — and how Dave finally broke the cycle→ How he started Five Star Co-Host over from scratch after realizinghe'd built it wrong the first time→ The $100K IRA withdrawal that gave him the team he needed to grow→ Why he went from 30 properties to 58 in just 5 months — and the threeobsessions that made it possible→ The $80,000 trust account crisis that hit in September 2025 — and whyhis response to it doubled the business→ What it actually takes to build a management company worth $100M(and why Dave believes it's just a choice)This is not a highlight reel.It's the version of the story most people are too scared to tell.Want to connect with Dave? Find him on Instagram: @dave_menapaceJoin the community: STR Secrets Facebook GroupFree 6-step course: level.strsecrets.com/pc-bookTimestamps: 00:00 - "Seven streams of income is not seven jobs"08:07 - Leaving corporate, WealthCon, and the birth of Five Star Co-Host15:48 - The Miami pool moment Kim told E: "my husband is doing a million things"32:21 - The most important thing Kim ever said to Dave35:45 - The three obsessions that unlocked 30 to 58 properties in 5 months48:17 - The $80,000 crisis and what focus does under pressure
Tax season just got a lot more interesting.In this episode, Mark Lumpkin sits down with CPA and real estate tax strategist Ryan Carriere to break down one of the most powerful tax strategies available to short-term rental investors today.Ryan explains how the return of 100% bonus depreciation under the One Big Beautiful Bill impacts investors, why the Short-Term Rental Tax Loophole remains a game changer for high-income earners, and the specific rules you must follow to qualify.They cover:• The return of 100% bonus depreciation and what it means for investors• How the Short-Term Rental Tax Loophole actually works• The 7-day average stay rule explained• Material participation requirements and common mistakes• How to track hours correctly for audit protection• Personal use rules that can destroy your tax benefits• Why most investors need a tax strategist, not just a tax preparer• Real-world examples of how investors can potentially save six figures in taxesIf you're buying short-term rentals for cash flow, appreciation, and tax savings, this episode is essential listening.Connect with Ryan Carrier:Website: CarrierTaxConsulting.comLinkedIn: Ryan Carrier, CPAYouTube: Ryan Carrier, CPA__Episode Sponsored By:STR SearchSTR Search is the industry leading property finder service. They've helped investors acquire over 215 profitable STRs across the US. If you'd like the data professionals to help you find your next STR, reach out to STRsearch.com
Navigating short-term rental regulations in Summit County just got a whole lot easier. In this episode, Candice De unveils a brand-new interactive map tool — built with the help of AI — that consolidates STR licensing information from all seven jurisdictions and unincorporated Summit County into one searchable, parcel-level map.Candice walks through each basin and municipality — Silverthorne, Dillon, Keystone, Frisco, Copper Mountain, Blue River, and Breckenridge — breaking down where licenses are available, where waitlists exist, and where STRs are restricted altogether. She also shares a critical update on Blue River's 2026 license freeze and explains why understanding STR eligibility matters even if you never plan to rent your property.Find the map at amynakos.com/short-term-rentals.Note: This map covers jurisdictional rules and does not include HOA overlays.
Are you prepared for the Airbnb landscape to feel brutally different this summer? Kenny Bedwell, founder of STR Insights and numbers-driven host of Cash Flow Positive, pulls back the curtain on the truth behind short-term rental trends and the shifting power moves that will make or break your returns in 2026.In this hard-hitting episode, Kenny Bedwell reveals why stabilization is here, what “professionalization” actually means for hosts, and how oversaturation is crushing easy wins. You'll hear the rare data and stories behind $10K bookings, competitive vendor wars, and why flashy isn't always smart. Learn exactly where experienced investors are pivoting and what the herd of copycats is missing.Miss this episode, and you risk falling behind in the new normal leaving real profits and lasting success for someone else. Listen now for the brutal, numbers-first roadmap you won't find in overhyped trend recaps.Timestamped Highlights00:18 – The subtle factor that will quietly decide who survives in STRs02:00 – A $10K summer booking that exposes the game-changing power of peak season04:29 – Why even expensive gas and rising costs are not slowing down travel demand06:24 – The unexpected data that proves market stabilization is here07:50 – Professionalization crushes returns for lazy investors (and creates opportunity)10:38 – The overlooked negotiating trick you should use with every vendor now12:36 – What most investors miss when evaluating their competition each summer16:08 – How “commercialized amenities” quietly future-proof your rental (with real examples)19:00 – Why tired strategies are failing and what separates investors with infinite returns21:30 – The costly mistake of chasing trends instead of compounding long-term valueMentioned ResourcesAirbnbCan MonkeyHost BuddySheratonMarriottImportant LinksWant us to find the deals for you? https://strinsights.com Get Top Markers for STRs (2025) - https://rebrand.ly/28b1df Instagram – @kenny_bedwellYouTube – Cash Flow PositiveLinkedIn – Kenneth BedwellCash Flow Positive is an original podcast hosted by Kenny Bedwell. Brought to you by STR Insights. Production and editing by Podcast Your Brand.
A dirty property can ruin a guest experience before the vacation even begins.In this episode, Mark sits down with Logan, founder of Dream Clean Team, one of the largest vacation rental cleaning companies on Florida's Emerald Coast. Starting as a side hustle with his wife cleaning properties during summer break, Logan has grown the business into a full-service operation serving hundreds of short-term rentals across Northwest Florida.The conversation dives into one of the most overlooked parts of STR success: cleaning systems, guest readiness, and operational consistency.You'll learn:• The difference between a clean property and a guest-ready property • Why laundry is often the biggest bottleneck in vacation rentals • How professional operators scale cleaning across hundreds of properties • The systems and SOPs that transformed a small side hustle into a major operation • How cleaning impacts reviews, rankings, and repeat bookings • Real stories of the wildest guest damage and turnover situations they've encountered • How AI is helping streamline operations without replacing peopleIf you're an STR owner, host, property manager, or investor, this episode will change the way you think about cleaning, guest experience, and operational excellence.__Episode Sponsored By:STR SearchSTR Search is the industry leading property finder service. They've helped investors acquire over 215 profitable STRs across the US. If you'd like the data professionals to help you find your next STR, reach out to STRsearch.com
HELP US IMPROVE THE PODCAST - TAKE THIS 3 MIN SURVEY:https://forms.gle/fRTV2YiJqncKVpFh7WEBINAR LINK:https://shawnmoore.clickfunnels.com/optiniyvvg89sWant 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-15a5caa687b7FOLLOW US:https://www.instagram.com/vodysseyshawnmoorehttps://www.facebook.com/vodysseyshawnmoore/https://www.linkedin.com/company/str-financial-freedomhttps://www.tiktok.com/@vodysseyshawnmooreCONTACT US:support@vodyssey.comPROPERTIES:https://www.airbnb.com/rooms/1667348904350233215?unique_share_id=26c563d9-be21-4667-80da-13b9daf699d1&viralityEntryPoint=1&s=76&source_impression_id=p3_1777312723_P3yexqjgooDm6_UcChapters00:00:00 Intro00:03:05 Background and Motivation for Short-Term Rentals00:05:50 Understanding Tax Benefits and Investment Strategy00:08:45 Family Involvement and Personal Use of Properties00:11:59 The Setup Process: Challenges and Fun00:15:05 Market Research and Property Selection00:17:59 DIY Approach vs. Turnkey Solutions00:20:50 Designing for Success: Standing Out in the Market00:25:02 Designing for Success: The Importance of Aesthetics00:28:42 Navigating Launch Delays: Planning and Execution00:31:19 The Power of Local Expertise: Finding the Right Realtor00:36:10 Performance Metrics: Analyzing Launch Success00:41:02 Lessons Learned: Embracing Challenges in the Process
AI is moving faster than most short-term rental hosts realize.In this episode of the STR Investing Podcast, Mark Lumpkin welcomes back Boostly founder Mark Simpson for a deep dive into how AI agents, automation, and direct booking technology are changing the future of hospitality.Mark Simpson shares how he went all-in on AI at the beginning of 2026, replacing repetitive manual tasks with AI agents that now help run parts of his business 24/7. What started as simple experiments quickly turned into real revenue, operational efficiencies, and entirely new systems for managing guests, marketing, and direct bookings.Throughout the conversation, they discuss the difference between basic AI chat tools and true AI agents, how operators can use AI without losing the hospitality element, and why most hosts are still thinking too small when it comes to automation.They also break down:AI agents and how they actually workUsing automation to increase direct bookingsWhy hospitality still matters more than AIThe future of Airbnb algorithms and booking platformsAI tools that save operators hours every weekHow hosts can leverage guest data more effectivelyThe importance of owning your customer relationshipsReal examples of AI-generated revenue growthMark also shares details about Boostly Connect, the new platform designed to help hosts better manage guest data, automate outreach, and improve direct booking performance.If you're trying to stay ahead in the short-term rental industry, this is an episode you don't want to miss.__Episode Sponsored By:STR SearchSTR Search is the industry leading property finder service. They've helped investors acquire over 215 profitable STRs across the US. If you'd like the data professionals to help you find your next STR, reach out to STRsearch.com
Ever lost thousands simply by trusting the wrong process or the wrong person?Kenny Bedwell returns from a break not just with fresh life perspective but with the hard-won, painful truths of renovating an 1848 boutique hotel from hundreds of miles away. This episode dives deep into the exact mistakes that cost him actual cash, and even more valuable time from contractor sequencing chaos to shipments gone missing to why “project management by Zoom” is a surefire road to blown budgets.If you own or plan to own any STR, now's the time to learn how to lead projects to the finish line without bleeding money. Skip this one, and you risk repeating the most expensive rookie mistakes in the book. Listen now for practical, brutally honest strategies you're not getting anywhere else.Timestamped Highlights00:11 – The real cost of learning by fire on big renovation deals01:47 – The one-day trip that revealed everything broken about remote project management03:14 – Why showing up in person sparks a momentum shift with contractors05:25 – How a simple shipping oversight vanished $2,000 overnight06:10 – Where even pros screw up sequencing and lose weeks08:08 – The shocking truth about contractor incentives (and why they don't care)09:25 – The proven fix that instantly cuts through project chaos12:10 – Why virtual management almost always leads to costly delays15:44 – Life-after-loss: Exact steps to prevent these disasters in your next STR projectMentioned ResourcesWayfair consolidated delivery serviceAmazon (referenced for shipping)Important LinksWant us to find the deals for you? https://strinsights.com Get Top Markers for STRs (2025) - https://rebrand.ly/28b1df Instagram – @kenny_bedwellYouTube – Cash Flow PositiveLinkedIn – Kenneth BedwellCash Flow Positive is an original podcast hosted by Kenny Bedwell. Brought to you by STR Insights. Production and editing by Podcast Your Brand.
On this special holiday episode of Good Morning Hospitality, Brandy Canaley and Michael Goldin unpack one of the biggest shifts happening in travel right now: AI-powered booking. Joined by Jason Cincotta, founder of Kismet, the conversation breaks down Google's new push into agentic hotel booking, what it means to become “AI-bookable,” and why independent hotels and vacation rentals may need to rethink how they show up online. The episode also dives into Airbnb's massive Summer Release, including boutique hotels, AI-powered review tools, airport pickups, grocery delivery, rental cars, and the company's expanding push toward becoming a full trip platform. Michael and Brandy debate whether Airbnb's latest features are meaningful product evolution or just great PR, while also exploring how AI could reshape direct bookings, loyalty, and the future of travel planning. This episode is presented by Plusgrade & Bilt. Visit plusgrade.com to learn more. And for hotels with restaurants and restaurant owners, Bilt Hospitality is finally here. Go to joinbilt.com/gmh to learn more.
What happens when a short-term rental operator loses over $1,000,000 during COVID?In this episode of the STR Investing Podcast, Mark Lumpkin sits down with Jason Baxter to talk about the highs, lows, and future of the short-term rental industry.Jason shares how he accidentally got started in Airbnb over 10 years ago, scaled to a portfolio of 50 lofts in Montreal, and then watched everything collapse during the COVID shutdowns in Canada.Facing bankruptcy, Jason rebuilt from the ground up by leaning into technology, automation, hospitality, and smarter booking strategies.In this episode, they dive into:The early days of Airbnb automationSurviving a million-dollar loss during COVIDThe biggest mistakes STR hosts make with techWhy hospitality still matters more than AIHow Airbnb algorithms really workPricing strategy and booking optimizationThe future of direct bookings and alternative platformsWhy “short-term rentals are a long-term game”Jason also explains how the right positioning and strategy helped one property grow from $65,000/year to over $210,000/year in bookings.If you're an STR investor, property manager, or host trying to scale smarter, this is an episode you don't want to miss.__Episode Sponsored By:STR SearchSTR Search is the industry leading property finder service. They've helped investors acquire over 215 profitable STRs across the US. If you'd like the data professionals to help you find your next STR, reach out to STRsearch.com
What if the difference between an average short-term rental and a standout, revenue-driving asset came down to story, strategy, and a few well-placed details on your walls? Most hosts view design as a finishing touch; my guest today views it as the core of the investment.In this episode, I'm joined by designer, investor, and boutique hotel visionary Courtney Petrovich of Denori Designs. We're talking about the intersection of high-level underwriting and high-impact creativity, and how you can use that balance to build properties that truly perform.We dive into:Why every creative choice, from a hot tub to a fire pit, must be backed by AirDNA data, pro formas, and a clear path to ROIDesigning for operational reality, turnover efficiency, and the hard truth about why white sofas and kids don't mixHow to create local resonance using custom pieces, regional cookbooks, and art that actually reflects the property's locationA deep dive into using wallpaper at the beach, including how to handle humidity, vetting installers, and spotting quality paper.How Courtney is translating STR logic into the boutique hotel world with a massive project in Page, Arizona.Courtney pulls back the curtain on how a site visit and a fascination with local history can lead to a hotel concept that investors instantly understand and get behind. You'll hear how she rethinks everything from lobby layouts to "cold plunge" amenities, ensuring that every design choice serves both the guest's emotions and the owner's bottom line.If you've been thinking of design as an optional expense rather than a strategic business tool, this conversation will completely shift your perspective. Get ready to start designing spaces that are profitable, operationally smart, and impossible to scroll past.HIGHLIGHTS AND KEY POINTS:[01:00] A short introduction about our guest Courtney Petrovich, and how her passion for design unexpectedly evolved into building a business within the short-term rental space[02:33] Courtney explains how balancing design, guest experience, and operational practicality shapes successful short-term rentals[06:15] Courtney shares how she discovered that thoughtful design directly influences performance and revenue in short-term rentals[09:27] Courtney describes the overlooked details that elevate guest experience beyond just design and amenities[12:29] Courtney explains how intentional, place-based art choices play a key role in elevating short-term rental design[13:39] How Courtney evaluates wallpaper choices for beach and humid environments, balancing durability, installation quality, and design impact[17:24] Courtney shares practical guidance on how to find a qualified wallpaper installer, emphasizing starting with trusted referrals such as local networks, or community groups rather[20:03] Courtney describes the challenges of installing wallpaper in beach homes where walls and ceilings are often not perfectly level and how installers navigate them[22:34] How transitioning into boutique hotel design has introduced Courtney to a more complex, on-site, and collaborative development process compared to short-term rentals[24:44] Courtney describes how boutique hotel design operates on a different scale than short-term rentals[28:02] How boutique hotel design uses immersive storytelling rooted in local history to shape a fully themed guest experience that extends from branding and interiors to reflective moments[31:13] Courtney shares how short-term rental owners can uncover a meaningful design story by starting with the nature, geography, and local history as the foundation for creative direction[32:45] Courtney explains how AI can support storytelling design, and why on-site experience remains critical for shaping boutique hotel guest experience[34:37] Courtney shares how working on a boutique hotel project revealed an unexpected but critical role of design in capital raising[37:50] Courtney describes how property owners can determine whether a designer is the right fit by first reviewing their portfolio to understand their aesthetic style and experience level[39:53] The lightning round Golden Nuggets:“We should be moving towards that level of detail that guests notice during their stay.”“When you're actually talking to designers in the short term rental space, it's important to find someone who's focused on short term rentals and not a residential designer. That can go really wrong, really fast.”“Always bet on yourself. So whatever your dreams are, your ambitions, whatever your heart desires, bet that you can do it and make that happen.”“What you believe about yourself, what you believe is possible, makes a huge impact on reality.”Let's Connect:Instagram : https://www.instagram.com/denoridesigns/Website : denoridesigns.com Proudly sponsored by Futurestay: futurestay.com/staceyEnjoyed the show? Subscribe, Rate, Review, Like, and Share!
Smart locks are no longer optional in short-term rentals.In this episode, Mark Lumpkin sits down with Amber Baron from Dormakaba to talk about why access control is one of the most overlooked parts of the guest experience — and how bad systems can completely ruin a stay.They break down:Why check-in is one of the most important moments in hospitalityThe biggest mistakes hosts still make with property accessWhy physical keys are creating massive operational headachesHow smart lock systems integrate with PMS software and automationThe importance of backup systems and emergency access plansHow remote operators can manage properties more securelyWhere AI and smart access technology are headed nextReal stories from the field — including a property manager literally Kool-Aid-manning through a door to save a guest stayIf you own, manage, or plan to scale short-term rentals, this episode is packed with practical insights on security, operations, and creating a smoother guest experience.Listen now and learn why access is the new front desk in hospitality.__Episode Sponsored By:STR SearchSTR Search is the industry leading property finder service. They've helped investors acquire over 215 profitable STRs across the US. If you'd like the data professionals to help you find your next STR, reach out to STRsearch.com
Chattanooga might be one of the biggest STR opportunities flying under the radar.In this week's Monday Market Data Report, Mark Lumpkin breaks down why Chattanooga is still in the early innings of the amenity arms race — and how investors can create a true “unicorn” property with surprisingly little competition.The numbers are eye-opening:Only 18% of listings have hot tubsOnly 3.8% have swimming poolsLess than 1% have movie theaters, saunas, mini golf, or pickleball courtsTranslation?Most properties in Chattanooga still look basic.That creates massive opportunity for investors willing to buy the right property, add strategic amenities, and stand out in a market that hasn't fully matured yet.In this episode, Mark breaks down:Why Chattanooga's tourism market keeps growingThe events and attractions driving travel demandWhich amenities are becoming mandatoryWhich amenities almost nobody has yetHow to create a top-performing STR without competing against thousands of heavily amenitized propertiesIf you've been looking for a market where you can still get ahead of the curve instead of fighting oversaturation, this episode is worth your attention.__Episode Sponsored By:STR SearchSTR Search is the industry leading property finder service. They've helped investors acquire over 215 profitable STRs across the US. If you'd like the data professionals to help you find your next STR, reach out to STRsearch.com
What happens when the “messy middle” of short-term rental hosting gets so chaotic that you decide to build the software you wish already existed? Most hosts just keep duct-taping systems together; my guest today decided to build a better way.In this episode, I sit down with Beth Turner, the non-technical founder of Simpli Host. We're talking about the unfiltered reality of operating multiple short-term rentals while working a demanding full-time job, and how that operational anxiety pushed her to create an all-in-one platform designed for the hands-on host.We dive into:The "messy middle" of juggling seven different apps and the constant anxiety of wondering if the cleaner showed up or the hot tub is actually hot.Practical tools for reclaiming your peace—from the power of a deep breath to reframing yourself as a true business owner rather than a "side-hustle" host.How repeated requests for help led to a platform with unified messaging, integrated locks, and seasonal maintenance reminders.The hard lessons of hiring and firing dev teams, trusting the experts, and resisting the urge to "just learn to code."Why establishing firm policies and guardrails around things like pets and trash days is the only way to protect both your profit and your sanity.But this isn't just about software. It's about buying back your time. We pull back the curtain on the importance of quiet time, journaling, and surrounding yourself with a community that understands the unique weight of this industry. You'll hear about the power of a daily gratitude practice and a vision for building a business that serves your life, rather than one that consumes it.If you've ever felt like you're drowning in notifications and logistics, this conversation will offer you a roadmap to systems, support, and a more aligned way of hosting. Get ready to move out of the chaos and into a more intentional way of leading.HIGHLIGHTS AND KEY POINTS:[00:47] A short introduction about our guest Beth Turner, her accidental journey into short-term rentals, and how she started Simpli Host[02:52] Beth describes the chaotic behind-the-scenes reality that quietly overwhelms hosts before they realize something has to change [05:13] Beth and I challenge the “passive income” myth and highlight the hands-on reality of running short-term rentals[06:51] Beth shares how the “messy middle” actually begins earlier, when juggling a full-time job, constant travel, and nonstop guest demands[09:40] Beth reveals how simple mental shifts, not complex systems, helped her regain control in high-stress hosting moments[12:18] How separating identity from the business helps operators lead more objectively, improve standards, and make stronger operational decisions[16:44] How documenting processes, especially through simple repeatable methods, prevents knowledge from being siloed and ensures business continuity and consistency[20:41] How using policies as a neutral authority helps operators remove emotion from guest decisions and maintain consistency, even when running solo[21:54] Beth explains how fragmented systems and operational overload led her to create Simpli Host as a unified solution for short-term rental management[25:37] Beth describes how the software functions as a centralized system that brings together the core operational layers of short-term rental management[31:58] Beth explains how building Simpli Host forced her to delegate, stop coding herself, and shifting from frustration and control to empowerment and trust in her team[34:36] Beth and I explore how clarity, creativity, and business insight emerge through quiet reflection, self-awareness, and intentional disconnection from noise[43:56] The importance of surrounding yourself with a supportive network of women and operators at different stages of their short-term rental journeys[47:26] The lightning round Golden Nuggets:“One thing that people don't realize is, STRs are not passive.”“You feel that rising and you know that you're no longer in a good mental space to make good choices. And even if you do make good choices, you're rolling the dice on that choice when you're in that state. So one of those is taking, taking that deep breath.”“I think it is so important that we learn as business owners to separate ourselves from the business.”“Having good people in your business is 100% essential. However, I will say, you know, I learned a huge lesson. Yeah, along with those good people, we have to make sure that if they're smarter than you about something, they're helping you build your policies, your processes and procedures. So that if they ever got hit by a bus, you know you would still operate without them.”“Exploit your strengths and hide your weaknesses.”“Having a network of other women around us who have experienced different things that are in all different stages of their businesses, I will tell you, I have mastermind programs. I have mentorships, I learn as much from the folks that I have the opportunity to support in their journeys as they learn from me.”“All of these masterminds, all these beautiful women, all of these smart, ambitious people that I've been around have gotten me where I am today. I carry a little bit of them everywhere I go.”Let's Connect:Website : https://simplihost.com/ Instagram : https://www.instagram.com/simplihostinc/Facebook : https://www.facebook.com/simplihostincEnjoyed the show? Subscribe, Rate, Review, Like, and Share!
Are you stuck grinding but never really escaping?In this punchy solo episode, Kenny Bedwell drops the curtain on the two proven secrets that transformed his own portfolio, and he does not sugarcoat the realities. With sharp stories of scrappy beginnings, W2 frustration, and the gut-check moment that forced him to choose between comfort and growth, Kenny Bedwell dives deep into the real reasons investors stall out.Listen in if you're ready to challenge the “just buy another unit” mentality, discover why time (not money) is your biggest bottleneck, and learn exactly what stops even high-income professionals from breaking through. Miss this episode and you're gambling with years of wasted effort, stretching your goals into a never-arriving someday. Hit play now for straight answers you truly won't find recycled elsewhere.Timestamped Highlights00:00 – What most investors get wrong about “scaling up”01:58 – The single conversation that shattered my old plan03:49 – The moment I made triple rent… and everything changed05:25 – The ugly reality of juggling W2, family, and side hustles08:23 – The corporate drama that forced my hand10:22 – Why time, not money, is your real shortcut to freedom14:42 – Why “bold” isn't gambling and how I protect against disaster16:40 – The uncomfortable moves that led to explosive cash flowMentioned ResourcesAirbnbBiggerPocketsImportant LinksWant us to find the deals for you? https://strinsights.com Get Top Markers for STRs (2025) - https://rebrand.ly/28b1df Instagram – @kenny_bedwellYouTube – Cash Flow PositiveLinkedIn – Kenneth BedwellCash Flow Positive is an original podcast hosted by Kenny Bedwell. Brought to you by STR Insights. Production and editing by Podcast Your Brand.
She thought it had to be one or the other.Career or kids. No middle ground.Then her daughter was diagnosed with leukemia at three years old.And everything changed.Jane Ng left corporate America to care for her daughter full time. Her daughter survived — but was left with a brain injury that means she will never be fully independent. Jane will care for her for the rest of her life.So going back to a W2 was never an option.Instead she found real estate. Then short term rentals. Then co-hosting. Then a coaching business helping other moms do the same thing.Today she owns 4 STRs, co-hosts 11 properties, runs a coaching business — and is home every single day for her kids.Here's what she shared in this episode:→ How she bought her first out-of-state property for $50K while parked on the side of a road in New Orleans→ Why STRs are one of the most powerful tax savings tools for stay-at-home parents→ How she built a team that runs the whole operation — with just one weekly check-in call→ How she structures her week so she is never tied to her phone→ The mindset shift that stopped her from quitting when things got hard→ How she uses AI to find her next STR market before she even talks to a realtor→ Why hospitality — not just for guests but for cleaners, neighbors, and vendors — is her #1 secretThis episode is for every mom who thinks she has to choose.She doesn't.Connect with Jane:Instagram: @theinvestingmomYouTube: @theinvestingmomConnect with us:Free 6-step course for scaling STR operators: https://level.strsecrets.com/pc-book STR Secrets FB group: https://www.facebook.com/groups/STRentalsecretsTimestamps:0:00 - Intro4:10 - Introducing Jane Ng: The Investing Mom4:42 - How Jane's Daughter's Diagnosis Changed Her Life Forever6:21 - Why Going Back to a W2 Was Never an Option7:03 - Parked on the Side of a Road in New Orleans: The Moment Everything Changed8:20 - From Long-Term Rentals to STRs: The 1031 Exchange That Started It All9:18 - Why Her Daughter's Illness Made Her Braver in Business11:39 - The Middle Ground: How STRs Let Her Be a Mom and an Operator13:28 - The Identity Guilt That Holds Moms Back — and How to Get Past It15:10 - Her Morning Routine: Up at 5:30, Kids First, Business Second18:01 - Portfolio Overview: 4 Owned STRs, 11 Co-Hosted Properties, 3 Businesses18:25 - Why the STR Tax Loophole Is a Game Changer for Stay-at-Home Parents20:32 - How Co-Hosting Started: She Said No 6 Times Before Saying Yes22:06 - How She Built Her Social Presence as a Self-Described Introvert25:49 - How She Manages Everything: VA Structure, Weekly Check-Ins and Time Blocking28:07 - How She Structures Her Week to Never Feel Tied to Her Phone31:07 - Start Small: How to Build Good Habits Without Overwhelming Yourself36:46 - How She Uses AI to Find Her Next STR Market39:19 - Her #1 Secret to STR Success: Hospitality for Everyone
She thought it had to be one or the other.Career or kids. No middle ground.Then her daughter was diagnosed with leukemia at three years old.And everything changed.Jane Ng left corporate America to care for her daughter full time. Her daughter survived — but was left with a brain injury that means she will never be fully independent. Jane will care for her for the rest of her life.So going back to a W2 was never an option.Instead she found real estate. Then short term rentals. Then co-hosting. Then a coaching business helping other moms do the same thing.Today she owns 4 STRs, co-hosts 11 properties, runs a coaching business — and is home every single day for her kids.Here's what she shared in this episode:→ How she bought her first out-of-state property for $50K while parked on the side of a road in New Orleans→ Why STRs are one of the most powerful tax savings tools for stay-at-home parents→ How she built a team that runs the whole operation — with just one weekly check-in call→ How she structures her week so she is never tied to her phone→ The mindset shift that stopped her from quitting when things got hard→ How she uses AI to find her next STR market before she even talks to a realtor→ Why hospitality — not just for guests but for cleaners, neighbors, and vendors — is her #1 secretThis episode is for every mom who thinks she has to choose.She doesn't.Connect with Jane:Instagram: @theinvestingmomYouTube: @theinvestingmomConnect with us:Free 6-step course for scaling STR operators: https://level.strsecrets.com/pc-book STR Secrets FB group: https://www.facebook.com/groups/STRentalsecretsTimestamps:0:00 - Intro4:10 - Introducing Jane Ng: The Investing Mom4:42 - How Jane's Daughter's Diagnosis Changed Her Life Forever6:21 - Why Going Back to a W2 Was Never an Option7:03 - Parked on the Side of a Road in New Orleans: The Moment Everything Changed8:20 - From Long-Term Rentals to STRs: The 1031 Exchange That Started It All9:18 - Why Her Daughter's Illness Made Her Braver in Business11:39 - The Middle Ground: How STRs Let Her Be a Mom and an Operator13:28 - The Identity Guilt That Holds Moms Back — and How to Get Past It15:10 - Her Morning Routine: Up at 5:30, Kids First, Business Second18:01 - Portfolio Overview: 4 Owned STRs, 11 Co-Hosted Properties, 3 Businesses18:25 - Why the STR Tax Loophole Is a Game Changer for Stay-at-Home Parents20:32 - How Co-Hosting Started: She Said No 6 Times Before Saying Yes22:06 - How She Built Her Social Presence as a Self-Described Introvert25:49 - How She Manages Everything: VA Structure, Weekly Check-Ins and Time Blocking28:07 - How She Structures Her Week to Never Feel Tied to Her Phone31:07 - Start Small: How to Build Good Habits Without Overwhelming Yourself36:46 - How She Uses AI to Find Her Next STR Market39:19 - Her #1 Secret to STR Success: Hospitality for Everyone
STR software is evolving fast - but the best operators know the real edge isn't just automation.In this episode of the STR Investing Podcast, Mark Lumpkin sits down with Amber Knight from bookingcloud.com to break down where the industry is headed—and what most hosts are still getting wrong.Amber shares her journey from helping scale early-stage operations at Vacasa to building new technology that drives visibility, bookings, and revenue for short-term rental operators.They dive into:• How automation is reshaping the STR industry• Why most hosts are still behind on direct booking strategy• The real role of AI in your business (and what it can't replace)• How top operators are driving more visibility and bookings• Why guest experience is still the ultimate differentiatorAs Amber puts it: you can automate processes—but you can't automate how a guest feels. If you're managing properties, building a brand, or trying to scale your STR business, this episode will challenge how you think about tech, marketing, and hospitality.Listen now and start building a more profitable, experience-driven STR business.__Episode Sponsored By:STR SearchSTR Search is the industry leading property finder service. They've helped investors acquire over 215 profitable STRs across the US. If you'd like the data professionals to help you find your next STR, reach out to STRsearch.com
On this episode of Zen and the Art of Real Estate Investing, Jonathan Greene interviews Julie Thomas, founder of The STR Edit and The STR Visionary, who shares how she built a successful short-term rental business starting with a $20,000 budget. Julie walks through her journey from being a teacher to becoming an experienced investor and designer, helping others create high-performing STR properties without overspending. Julie explains how her first investment in West Yellowstone came from poor guest experiences and a desire to do better. She and her husband took a hands-on approach, sourcing furniture creatively, prioritizing key amenities, and focusing on guest experience to dramatically increase revenue and reviews. The conversation also highlights the biggest misconceptions about short-term rentals, including the idea that they require massive design budgets or operate as passive income. Julie emphasizes the importance of understanding your market, knowing your guest avatar, and balancing both design and operations to create a successful property. Jonathan and Julie also discuss practical strategies like setting a strict budget, avoiding unnecessary upgrades, and learning from real guest feedback. They stress that strong operations, responsiveness, and attention to detail are just as important as aesthetics when it comes to earning five-star reviews and repeat bookings. In this episode, you will hear: How Julie Thomas got started in short-term rentals with a $20K budget Why most STRs don't require massive design budgets to succeed The biggest mistakes new investors make when getting started How to balance design and operations to improve guest experience Why knowing your market and guest avatar is critical to success Follow and Review If you enjoy the show, please follow Zen and the Art of Real Estate Investing on Apple Podcasts and leave a rating and review. It helps other listeners discover the show and supports its continued growth. Supporting Resources Connect with Julie: Website: https://www.stredit.com/ LinkedIn: https://www.linkedin.com/in/strvisionary/ Connect with Jonathan: Podcast - www.zenandtheartofrealestateinvesting.com Brokerage - www.streamlined.properties YouTube - www.youtube.com/c/JonathanGreeneRE/videos Instagram - www.instagram.com/zenrealestateinvesting Instagram- www.instagram.com/trustgreene Instagram - www.instagram.com/streamlinedproperties Instagram - www.instagream.com/zenupstate Zillow - www.zillow.com/profile/trustgreene Bigger Pockets - www.biggerpockets.com/users/TrustGreene Facebook - www.facebook.com/zenandtheartofrealestateinvesting Jonathan's Hub Site - www.trustgreene.com Email - Jonathan@trustgreene.com This episode was produced by Outlier Audio.
What if the biggest threat to your short-term rental business… is also your biggest opportunity? In this episode of The STR Data Lab, Jamie Lane sits down with returning guest Mark Simpson to unpack how AI is rapidly reshaping the STR landscape—and what hosts and property managers need to do right now to stay ahead.From London conference “carnage” to real-world AI experiments generating thousands in bookings, Mark shares a front-row view of how operators are no longer just using tech—they're building it. The conversation dives into the rise of AI-powered workflows, custom-built tools, and “AI chiefs of staff” that can analyze, optimize, and even run parts of your business. The result? A shift from reactive hosting to proactive, data-driven growth.But this isn't just about automation—it's about strategy. As OTAs continue to dominate, Mark makes the case that direct bookings aren't dead—they're evolving. With AI lowering the barrier to entry, hosts now have unprecedented access to tools that can drive repeat guests, unlock new revenue streams, and personalize guest experiences at scale. The question isn't whether AI will change your business—it's whether you'll adapt fast enough to benefit.You don't want to miss this episode.Key TakeawaysAI is eliminating traditional barriers to growth Lack of time, money, or technical expertise is no longer an excuse—hosts can now build powerful workflows and tools with minimal effort.Direct bookings aren't dead—they're entering a new phase With smarter targeting, personalization, and AI-driven outreach, operators can reclaim repeat guests and drive more direct revenue.Your “AI Chief of Staff” is closer than you think By connecting your PMS, CRM, and tools to AI, you can get real-time insights, automate decisions, and run your business more efficiently.The real revenue opportunity goes beyond the stay Upsells, services, and partnerships (like private chefs or local experiences) are becoming critical profit drivers—not just nice-to-haves.Not all AI tools are created equal—buyer beware Many flashy tools are just “AI slop.” Look for real functionality, proven results, and tools that actually integrate into your workflow.Sign up for AirDNA for FREE
#882 Thinking about investing in an Airbnb but not sure how to know if it's a good deal? In this episode, host Brien Gearin sits down with John Bianchi — founder of STR Search and widely known as “The Airbnb Data Guy.” John shares how he went from financial advisor to short-term rental data expert, helping investors avoid costly mistakes and identify profitable properties using deep data analysis. You'll learn what really makes an Airbnb stand out, how to evaluate markets, the truth about today's STR landscape, and why understanding your numbers is more crucial than ever! (Original Air Date - 8/27/25) What we discuss with John: + How John became “The Airbnb Data Guy” + Transition from financial advisor to STR expert + Why most people buy the wrong Airbnb properties + How STR Search helps investors with data + Common Airbnb revenue-driving features + Importance of pricing strategy and revenue managers + Why many STRs fail — and how to avoid it + Airbnb market conditions in 2025 + The truth behind the “Airbnb bust” narrative + How to use STRs for tax savings and cash flow Thank you, John! Check out STR Search at STRSearch.com. Follow John on Instagram and YouTube. Watch the video podcast of this episode! To get access to our FREE Business Training course go to MillionaireUniversity.com/training. To get exclusive offers mentioned in this episode and to support the show, visit millionaireuniversity.com/sponsors. Learn more about your ad choices. Visit megaphone.fm/adchoices
Are your short-term rentals sitting empty while your competitors rake in bookings? You might be targeting the wrong guest without even knowing it. In this tough-love, numbers-driven solo episode, Kenny Bedwell, founder of STR Insights, reveals the six REAL buyer personas that drive every booking decision and why most hosts get it dead wrong.Cut through the industry fluff: This episode breaks down how each persona thinks, what drives their decisions, and how seasonality radically shifts who you're really marketing to. Whether you're struggling to fill high-end properties, want to squeeze more out of the low season, or just avoid attracting guests who tank your reviews, this episode gives you direct, actionable insight you simply won't find on other STR podcasts.Stop the guesswork. Listen right now to protect your cash flow, outsmart your competition, and attract the guests you actually want. These frameworks are exclusive, urgent, and can change your booking game overnight.Timestamped Highlights00:02 – Dad shirts are back… but is your STR guest strategy stuck in winter?00:44 – The secret reason you keep attracting the “wrong” guests (and how to fix it)03:03 – Why budget buyers will ignore your amenities—and the pricing trap most hosts fall into07:32 – Value seekers, Costco logic, and the most common STR buyer (are you missing easy profits here?)10:46 – The convenience persona: Why location, reviews, and guarantees can replace discounts13:17 – Experience seekers exposed: Social media-worthy guests—and the Instagram marketing mistake16:55 – Luxury buyer drama: When high expectations drive guests to cancel… and why “luxury” is more than just a word20:29 – Occasion seekers and the money left on the table when you ignore group dynamicsMentioned ResourcesAirbnb LuxeCostco, Sam's Club, Dollar Tree (buyer mindset examples)Instagram (direct booking for experience stays)Marriott, Sheraton (hotel chains, buyer persona contrasts)Important LinksWant us to find the deals for you? https://strinsights.com Get Top Markers for STRs (2025) - https://rebrand.ly/28b1df Instagram – @kenny_bedwellYouTube – Cash Flow PositiveLinkedIn – Kenneth BedwellCash Flow Positive is an original podcast hosted by Kenny Bedwell. Brought to you by STR Insights. Production and editing by Podcast Your Brand.
In this Good Morning Hospitality, A Skift Podcast Bonus episode, Brandreth Canaley and Michael Goldin sit down with Tim Rosolio, VP of Vacation Rental Partnerships at Vrbo/Expedia Group, from a standout “Vacation Rental of the Year” property in New Hampshire. Tim breaks down what actually drives performance on Vrbo today, from must-have amenities and pricing strategies to the growing importance of quality, consistency, and reviews in an increasingly saturated market. He shares why the short-term rental “gold rush” is officially over, and what operators need to do now to stay competitive. The conversation also dives into Expedia Group's broader strategy, including the rapid growth of B2B distribution, the expansion of vacation rentals across Expedia's ecosystem, and how new tools like promotions and sponsored listings are changing visibility and bookings. They also tackle AI in travel, where it's already delivering value, where it's overhyped, and why the human element still matters in hospitality. Episode Chapters: 00:00 Snowy New Hampshire Setup 01:08 Why This Rental Won 01:26 How Vrbo Picks Homes 02:35 Hosts Who Go All In 05:22 Amenity Must-Haves 07:57 Boosting Rankings Fast 08:25 Promotions That Convert 10:25 Is The Gold Rush Over 12:44 Quality Over Quantity Era 16:58 Standards And Trust Issues 19:00 Cleaning and Reviewing Data 20:26 Reviews Signal Quality 21:36 Star Ratings Confusion 22:26 B2B Growth Expansion 25:09 AI In Travel Tech 26:32 Keeping Human Hospitality 28:16 OneKey On Vrbo 29:48 Sponsored Listings Launch 33:14 Rapid Fire Wrap Up Connect with Skift LinkedIn: https://www.linkedin.com/company/skift/ WhatsApp: https://whatsapp.com/channel/0029VaAL375LikgIXmNPYQ0L/ Facebook: https://facebook.com/skiftnews Instagram: https://www.instagram.com/skiftnews/ Threads: https://www.threads.net/@skiftnews Bluesky: https://bsky.app/profile/skiftnews.bsky.social X: https://twitter.com/skift Subscribe to @SkiftNews and never miss an update from the travel industry.
In this episode of Tax Tuesday, Anderson advisors Eliot Thomas, Esq., and Barley Bowler, CPA, tackle a packed lineup of listener questions covering construction business accounting, rental property depreciation, and family tax planning. They explain the pros and cons of switching from accrual to cash accounting, and when a SEP or Solo 401(k) can help reduce a tax bill before an extension deadline. They walk through how to claim a college student as a dependent even if the student earns grant income, and how hiring your kids through a C corporation can shift income and fund a Roth IRA. Eliot and Barley detail how the Ladybird enhanced life estate deed works in the five states that allow it, and how stepped-up basis applies at inheritance. They cover when a management corporation makes sense for short-term rental owners with W2 jobs, the real risk of children's working hours undermining a spouse's material participation, and how the aggregation election simplifies real estate professional status across multiple properties. Other topics include how to catch up missed depreciation using Form 3115, how to properly report an owner-financed note, and whether repairs and maintenance on a non-income-producing rental are deductible. Tune in for expert guidance on these topics and more! Submit your tax question to taxtuesday@andersonadvisors.com Highlights/Topics: 00:00 Intro to Tax Tuesday with Eliot and Barley 7:09 We file accrual; however, if I switch to cash, the tax bill will be lower. Is this a good idea? Is there anything I can do to lower 2025 taxes before my extension is due in September, like a SEP or retirement plan? - Cash basis is simpler; a SEP or Solo 401(k) can still be established. 16:16 My son gets some grant money from the University for his peer mentor role and research he does. He is a Junior and is 20 years old. Can I still list him as before as a dependent on my tax return? - Yes, if you provide more than half of his total annual support. 21:28 What are the tax ramifications of my brother and I inheriting my mom's home via a Ladybird (enhanced life estate) deed? - You receive stepped-up basis; rental or personal use rules then apply. 27:17 My husband and I both have W2 jobs. We have both long-term and short-term rentals. I manage the STRs. Does it make sense that I open an S Corporation as a management company? Is there an additional advantage to employing my teenage kids to help manage properties? - A C corporation management company maximizes tax-free reimbursement benefits for families. 39:00 We have a home management company (partnership). My spouse qualifies for REP status with no other job. Could he have both? Can you also elaborate on this: "Under §469, each rental property is treated as a separate activity. You must participate in each property. Not just your portfolio as a whole." - An aggregation election bundles all rentals to simplify material participation requirements significantly. 49:05 I have a single-family home rental. Depreciation was not taken on previous tax returns. How do I go back and calculate depreciation? -File Form 3115 to catch up all missed depreciation in one year. 53:50 How do I report the mortgage payment paid to me from my owner finance note? - Report interest received on Form 1098 and installment gain on Form 6252. 57:38 Can you write off expenses and maintenance costs for rentals that are not producing any income due to disrepair? - Yes, if the property remains available for rent or is temporarily out of service. Resources: Tax and Asset Protection Events https://andersonadvisors.com/real-estate-asset-protection-workshop-training/?utm_source=how-to-claim-missed-depreciation-on-a-rental-property%20&utm_medium=podcast Schedule Your FREE Consultation https://andersonadvisors.com/strategy-session/?utm_source=how-to-claim-missed-depreciation-on-a-rental-property%20&utm_medium=podcast Anderson Advisors https://andersonadvisors.com/ Toby Mathis YouTube https://www.youtube.com/@TobyMathis Toby Mathis TikTok https://www.tiktok.com/@tobymathisesq Clint Coons YouTube https://www.youtube.com/@ClintCoons
Are you obsessed with high booking rates, glowing reviews, or six-figure revenue? What if those metrics are secretly keeping you broke and blind to your property's true potential?In this punchy solo episode, Kenny Bedwell, founder of STR Insights and host of Cash Flow Positive, exposes the most overhyped “STR swear words” in the business, metrics that sound good but can destroy your bottom line if you chase them blindly. You'll learn why occupancy rate, guest ratings, and even jaw-dropping gross revenue can cost you time, money, and deal flow if you don't dig deeper.Don't gamble your freedom or future on surface numbers. Listen now to dodge expensive pitfalls, outsmart the sharks, and finally see REAL cash flow. Miss this episode, and you'll risk overpaying for duds nobody else wants to touch.Timestamped Highlights00:02 – The “STR swear words” that make Kenny Bedwell furious (and should make you nervous)02:26 – The real story behind high occupancy rates—why 100% bookings can be a trap04:24 – The 46% rule: How a “low” occupancy rate led to insane ROI (and less headaches)06:53 – The year-round bookings myth and why chasing monthly returns kills your annual gains08:00 – A 4.89-star rating, $60K more profit—what everyone gets wrong about reviews10:03 – Why high bookings and high ratings still don't guarantee cash flow (and what to demand instead)13:23 – Gross revenue exposed: How sellers weaponize the most misleading metric in STR16:13 – $5K “brag posts” vs. $2K net: The social media profit illusion you must avoidMentioned ResourcesVRBOAirbnbFacebookProfit & Loss statements (PNL)Booking Lead Time (industry trend)“Superhost” and Airbnb algorithm factorsImportant LinksWant us to find the deals for you? https://strinsights.comGet Top Markers for STRs (2025) - https://rebrand.ly/28b1dfInstagram – @kenny_bedwellYouTube – Cash Flow PositiveLinkedIn – Kenneth BedwellCash Flow Positive is an original podcast hosted by Kenny Bedwell. Brought to you by STR Insights. Production and editing by Podcast Your Brand.
Are your Airbnb profits slipping and you don't know why? Imagine waking up to a revenue model change that could make or break your short-term rental business. In this urgent solo episode, Kenny Bedwell breaks open the truth behind Airbnb's blockbuster reversal on host fees, the quiet switch nobody was supposed to notice, but every smart investor needs to understand today.You'll discover what's really behind the fee flip, how it impacts your property's ranking and bookings, and exactly how to adapt before the window slams shut. Don't let another booking cycle pass you by while others get ahead. If you care about maximizing profit and avoiding algorithm disaster, you need these exclusive, data-backed strategies right now. Only Cash Flow Positive gives you the real numbers, the pitfalls, and the playbook to WIN before the changes vanish again!Timestamped Highlights00:00 – The wildest podcast cold open yet—did Airbnb really listen to this show?01:45 – The “split fee” is BACK: What it means and why it matters for your profit05:40 – Insider data: What happened to hosts' bookings and income after the single fee switch08:30 – Why Airbnb claims hosts get “more bookings” (and why that's a vanity metric trap)12:55 – The one move you must make in your property management system to cash in17:00 – The truth about algorithm rankings and dropping your fees (what Airbnb won't say)18:40 – Top-performing properties vs. average: Who really survives policy chaos?20:00 – Exactly how to prepare for June's next pricing reset and outsmart 90% of hostsMentioned ResourcesVRBO (competitive shifts and booking volume)Airbnb Host Fee Structures (split fee vs single fee)Property Management Software (PMS)Emile Sakhel (industry revenue manager)Important LinksWant us to find the deals for you? https://strinsights.com Get Top Markers for STRs (2025) - https://rebrand.ly/28b1df Instagram – @kenny_bedwellYouTube – Cash Flow PositiveLinkedIn – Kenneth BedwellCash Flow Positive is an original podcast hosted by Kenny Bedwell. Brought to you by STR Insights. Production and editing by Podcast Your Brand.
Could the ingredients for life have arrived on asteroids? Neil deGrasse Tyson and comic co-host Chuck Nice unpack what the sample collected from asteroid Bennu is teaching us about the origins of life itself with Harold Connolly, geologist and mission scientist for OSIRIS-REx. NOTE: StarTalk+ Patrons can listen to this entire episode commercial-free here: https://startalkmedia.com/show/secrets-of-asteroid-bennu-with-harold-connolly-jr/ Thanks to our Patrons Kevin Widener, WilfriedLepuschitz, Rodney Juste, Aladin Mihai, Marc Washington, david smith, Gary Flenthrope, Christian Becker, EricRobert, Sonya a, Steve Jones, leeinalaska, Sewit Haile, Edward Janezich, Miguel Rodriguez, Shea M, Mister E, G.Montagnard, Vincent Jenkins, Ryan B, Brandon Kavulla, Owoskeun Cinder, LehensGivris, Marc, Debbie Evercloud, Fakhreddine Madi, Logan Koehler, Cem Oğuz, Aaron Greeley, Ohad Meir, Paul Osborne, Bodnár Márton János, STRS, Lawrence, THEO NNEBE, Richard Mosby, Kenneth Hawley, Robert Wilson, Amelia Cooper, mabus98, Mandana Rad, Lucas Kiil, Channing Hodges, Elizabeth Newton, Sebastián Egaña, Eric Hall, Sondre Rypdal, Anne Shirley, Andrew Rosenfeld, Michael Owen, T Playle, Kevin Selman, david Aldridge, Raymond Wright, Biotoxin, Brittany, Wraptile, Frances Cooley, Rodney Bell, Hesam Eskandari, Patrick Dietz, Alexandre Malouin, Diana Smith, Jesse Hoffman, Ian Peterson, WickedProf, Jonathan, SUSAN Moore, Tom DeGerlia, Jessica Holden, Simeon Ivaylov Petrov, Dario Kubler, Robert Passeri, Jr., Fred Miller, Jason Delancey, Rory L, Alice Kelaine Harline Davis, Loonertick, Rich, Jason Rich, jon meier, Susan, Robert Christine, Simon, Lauren Zajac, Brandon Abramovitz, J Sauce, Christopher Smith, Suzan Stocker, Roch Dylla, Treven Price, Zippo, Preet Sandhawalia, Chris McAfee, Hoth, Cody Mecham, Lewis, Casey Hampton, Jason Beezley, and Anthony Gliganic for supporting us this week. Subscribe to SiriusXM Podcasts+ to listen to new episodes of StarTalk Radio ad-free and a whole week early.Start a free trial now on Apple Podcasts or by visiting siriusxm.com/podcastsplus. Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.
What happens when two sisters team up to build a powerhouse short-term rental brand in two of the most competitive markets in the country? Most people think working with family is a recipe for disaster; Jen and Lauren prove it's actually a competitive advantage.In this episode, I sit down with Jen Stone and Lauren Schmidt, better known as The Airbnb Sisters. We're unpacking how they've grown a thriving portfolio across Nashville and 30A while keeping their standards sky-high and their sisterly bond intact.We talk about:How a single CMA Fest booking turned into a professional management career for Nashville's biggest developersThe strategy behind their iconic pink-themed homes and how they attract high-value group stays like weddings and bachelorette partiesHow Jen transitioned from personal assistant to the engine of the business, managing guest flow and flawless check-insThe story of finding (and fiercely protecting) a standout cleaning crew to maintain five-star standards from hundreds of miles awayA candid look at hosting large groups, and how their branding and screening process attract guests who actually respect the propertyBut this isn't just a story about pretty houses. It's about the evolution of a brand. Jen and Lauren pull back the curtain on the delicate conversations they have with owners about decor budgets and why they now insist on being involved before a home is even furnished. You'll hear how they still run a high-volume business with a personal touch, and my honest take on where they can finally let technology take some of the weight off their shoulders.If you've ever wondered how to turn a "side hustle" into a recognizable brand or how to successfully partner with family, this conversation is your front-row seat. Get ready to learn what it really takes to dominate the high-energy group stay market.HIGHLIGHTS AND KEY POINTS:[01:15] A short introduction about our guests Jen Stone and Lauren Schmidt, and share how they started and grew their short-term rental business together as sisters[05:42] Jen explains how she and Lauren divided roles while building their short-term rental business[07:16] Lauren shares why she brought her sister Jen into the short-term rental business[08:29] Jen explains how social media helped grow their short-term rental business and attract large group bookings[10:54] Lauren outlines their mixed short-term rental business model of ownership and management, and how a long-term developer partnership shaped their portfolio[13:41] Lauren highlights that running properties far from home, like their 30A beach rentals, is very different from managing Nashville homes[14:35] Jen and Lauren discuss managing long-distance properties and finding the right cleaning team [18:19] Lauren and Jen explain how they maintain quality and consistent design across their properties[20:12] Lauren describes managing guest communications themselves and my advice to them about dynamic pricing tool and property management software[26:57] Jen explains that their approach to adding properties is highly selective, focusing first on the relationship and communication style with the owner rather than just the property itself[29:19] How Jen and Lauren use experience and firm standards to guide budgeting and property fit decisions [33:12] Jen and Lauren debunks bachelorette myths and highlights the reality of high-quality group guests [36:00] Lauren and Jen share how they generally don't actively screen bachelorette parties or other group bookings and they treat all guests equally and welcome those who want to book[37:47] The lightning round Golden Nuggets:“It's so important that we've got backups and backups for our backups.”“You can have a beautifully designed property, but if it's poorly run, you're not going to get great reviews.”“If somebody is giving you trouble, kill them with kindness.”Let's Connect:Instagram : https://www.instagram.com/the.airbnb.sisters/ Enjoyed the show? Subscribe, Rate, Review, Like, and Share!
In 2016, Cara and Mark Truckey lost their 14-month-old son. He never woke up at daycare.Most couples don't survive a loss like that. Instead, it became the moment that changed everything.In this episode, E and Chris sit down with Cara and Mark Truckey — two STR Secrets boardroom alumni who have built a real estate portfolio of 65+ units across Wisconsin and Florida while raising three kids and running multiple businesses.This is one of the most honest and human conversations we have had on this show.In this episode Cara and Mark cover:- How losing their son reshaped their entire perspective on time, work, and money- How Cara quit her hospital job in 2020 and Mark quit his plumbing W-2 in 2021- How they went from a few house flips to 65+ rental units across two states- Their first STR — a lake property in Wisconsin they bought by accident- Why Mark struggled with delegation for years — and the 80/20 rule that broke the pattern- How to find the right people for the right seats — and why belief in the vision matters more than skills- How Cara transitioned into Savvy Realty as a top agent in the Tampa Clearwater market- What actually keeps a husband and wife business partnership aligned- The daily habit that is their real superpower — and has nothing to do with business- How to change your identity before the results show up- Mark's upcoming $130 million capital campaign for a K-12 school in Wisconsin- Cara's goal: 40 STRs under management in Florida by end of 2027- Their #1 secrets to success: courage and fighting past limiting beliefsIf you want to increase your revenue, automate your day to day operations and spend more time with your kids: http://strsecrets.com/applyIf you want to join our weekly free training:https://www.facebook.com/groups/STRentalsecretsConnect with Cara: Instagram: www.instagram.com/caratruckeyFacebook: www.facebook.com/caratruckeySavvy Realty: www.savvy.realty/caraTimestamps:0:00 - Highlights1:00 - Introducing Cara and Mark Truckey5:05 - Their Story: Growing Up in Wisconsin and Losing Their Son in 20167:32 - How Grief Changed Their Relationship With Time and Money9:03 - How They Built the Portfolio: Flips, BRRRs and Their First Accidental STR10:21 - How They Split the Business: Cara on Sales, Mark on Construction11:56 - Building the Team: Florida and Wisconsin Operations14:11 - Mark's Delegation Journey: The 80/20 Rule That Changed Everything16:48 - Right People in the Right Seats: Why Belief in the Vision Matters Most18:24 - Identity First: You Have to Become the Person Before the Results Show Up21:33 - How to Actually Change Your Identity — Not Just Understand It24:28 - Why Being Part of a Mastermind Has Always Been Their Edge25:25 - Running a Business With Your Spouse — What Actually Works26:47 - Spiritual Alignment: The Foundation That Kept Them Together Through Tragedy27:23 - The Matthew McConaughey Analogy: You Won't Always Walk Side by Side32:21 - How Cara Made the Decision to Join Savvy Realty35:00 - Their Real Superpower: Health, Accountability and Alignment38:27 - What's Next: Mark's $130M School Campaign and Cara's Management Goals42:23 - Their #1 Secrets to STR Success
Ever wondered why real estate investors lose big while others exit with effortless wins?In this can't-miss episode, Kenny Bedwell gets brutally real with veteran broker and multi-cycle investor Ryan Cadwell, exploring why the majority of investors walk into deals blind, and what separates the survivors from the victims when markets shift. You'll hear hard-won lessons from the Great Recession to today, the overlooked math that keeps you safe, and why your emotions are quietly sabotaging your wealth.Stop playing checkers in a chess market. Listen now to learn the proven, data-backed playbook for winning with your exit before you ever buy. Miss this, and you'll pay a premium for mistakes you could have avoided. Your future self is begging you not to skip these strategic insights, no fluff, zero hype, and exactly what the gurus won't warn you about.If you want to avoid painful losses, stop buying blind, and gain immediate edge in today's market—this episode is your ticket. Listen now before your competition does.Timestamped Highlights00:00 – The raw mistake that nearly took down veteran investors in ‘0805:12 – Why BlackRock's latest moves are the market signal you can't ignore10:07 – How optimism bias and emotional attachment wreck your returns14:19 – The 7 Whys Framework that exposes what investors really want17:34 – If you LOVE a deal, why that's your loudest red flag20:17 – The data traps: Outdated numbers, ignored expenses, and the illusion of “free” vacation homes25:54 – Rookie math that destroys deals and the exit-first equation that saves you35:02 – The 10-minute investment journal habit that will transform your discipline (and profit)About The GuestRyan Cadwell is a Certified Property Manager and Principal partner at Resolute RDM with nearly two decades of hands-on investment, development, and commercial consulting experience. Ryan's roots go back to family rentals at age 12, spanning every market cycle from the Great Recession to post-COVID surges. He's known for his surgical approach to due diligence, asset management, and the no-nonsense brokerage advice trusted by seasoned and rookie investors alike.
Are you racing to buy more properties but never stopping to ask, “What's my end game?” If you want true financial freedom from short-term rentals—not just another job—you need a proven, numbers-driven exit plan.Host Kenny Bedwell, founder of STR Insights, reveals why most investors build backwards and sabotage their long-term wealth. This episode exposes why cash flow is not the secret, how to use data to scale faster, and the killer reason your “forever” property usually isn't. Kenny tears down common myths, puts hard numbers behind every decision, and lays out a blueprint for achieving wealth beyond the next tax season.Listen now and escape the newbie trap, avoid five-figure mistakes, and get the exclusive strategic insights trusted by top-performing STR investors. Your next level depends on understanding your exit, and no one else is telling you this.Timestamped Highlights[00:00] – Why today's cash flow obsession is tricking investors out of real wealth[00:38] – The “backwards builder” myth and how serial investors think differently[02:58] – A jaw-dropping stat: Why 3–5 years is the true STR hold window[04:20] – The ROI vs ROE showdown when selling trumps holding[06:44] – The 1031 dilemma: Are you setting yourself up to be stuck?[09:09] – The tax savings rabbit hole and why one year of relief kills your strategy[11:09] – Kenny's market-moving confession: What happens when a crowd follows your lead[14:19] – How to spot the exact “sell trigger” (and double your portfolio wealth)[19:02] – The trap of quantity over quality—how chasing properties makes you your own worst bossMentioned Resources1031 Exchange strategyReturn on Equity (ROE)Return on Investment (ROI)Important LinksWant us to find the deals for you? https://strinsights.com Get Top Markers for STRs (2025) - https://rebrand.ly/28b1df Instagram – @kenny_bedwellYouTube – Cash Flow PositiveLinkedIn – Kenneth BedwellCash Flow Positive is an original podcast hosted by Kenny Bedwell. Brought to you by STR Insights. Production and editing by Podcast Your Brand.
Most Airbnb failures don't come from bad luck. They come from bad assumptions made before the deal ever closes. In this episode, John Bianchi, founder of STR Search, breaks down how he evaluates short-term rental deals using data most investors either misunderstand or completely ignore. John has helped guide more than $100M+ into short-term rental properties and has reviewed 350+ deals nationwide, all using a strict data-first process designed to avoid downside risk. This conversation focuses on how to pressure-test Airbnb deals so they still work when demand softens, regulations tighten, or competition increases. What we cover: Why many Airbnbs fail within 1–2 years The biggest mistakes investors make when reading Airbnb data How to identify bad data vs. reliable data in AirDNA Why listings must show 270+ days of activity and consistent reviews How regulations can quietly kill otherwise "great" deals Why cash flow matters more for STRs than long-term rentals John's 20% price-to-revenue rule and how it compares to the 1% rule Why Class-A vacation markets often underperform How oversupply, foreign capital, and design arms races crush returns What data reveals about competition, saturation, and revenue durability Why management matters less than buying the right property How John reverse-engineers top-performing listings to find winners Where investors go wrong trying to "make" bad deals work John also explains why he never publicly shares specific markets, how he thinks about regulatory risk at the state and local level, and why not buying a bad deal is often the real win. Resources: STR Search: www.strsearch.com Free 7-Day Airbnb Data Course available on the site This episode is essential listening for anyone considering short-term rentals, especially investors who want clear downside protection, not hype. Today's episode is brought to you by Green Property Management, managing everything from single family homes to apartment complexes in the West Michigan area. https://www.livegreenlocal.com And RCB & Associates, helping Michigan-based real estate investors and small business owners navigate the complex world of health insurance and medicare benefits. https://www.rcbassociatesllc.com
Send a textNational parks can be unbeatable demand engines… but hype also creates overpriced disasters. Then comes the deeper punch: people buying STRs that don't cash flow just to chase depreciation and getting hit again with recapture later. If you've ever justified a bad deal with “tax benefits,” this is your wake-up call.Learn how to invest in real estate with the Cashflow 2.0 System! Your business in a box with 1:1 coaching, motivated seller leads, & softwares. https://www.wealthyinvestor.com/Want to work 1:1 with Ryan Pineda? Apply at ryanpineda.comJoin our FREE community, weekly calls, and bible studies for Christian entrepreneurs and business people. https://tentmakers.us/Want to grow your business and network with elite entrepreneurs on world-class golf courses? Apply now to join Mastermind19 – Ryan Pineda's private golf mastermind for high-level founders and dealmakers. www.mastermind19.com--- 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 generated over 1 billion views online. Starting as a minor league baseball player making less than $2,000 a month, Ryan is now worth over $100 million. He shares his experiences in building wealth and believes that anyone can change their life with real estate investing. ...
Send a textEveryone keeps yelling “Airbnb is dead,” but the real truth is harsher: the easy wins are gone. If you learned STRs during the 2–4% rate era, you weren't a genius… you were playing on easy mode. Now it's a sophistication game: better deals, better hospitality, and way better execution.Learn how to invest in real estate with the Cashflow 2.0 System! Your business in a box with 1:1 coaching, motivated seller leads, & softwares. https://www.wealthyinvestor.com/Want to work 1:1 with Ryan Pineda? Apply at ryanpineda.comJoin our FREE community, weekly calls, and bible studies for Christian entrepreneurs and business people. https://tentmakers.us/Want to grow your business and network with elite entrepreneurs on world-class golf courses? Apply now to join Mastermind19 – Ryan Pineda's private golf mastermind for high-level founders and dealmakers. www.mastermind19.com--- 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 generated over 1 billion views online. Starting as a minor league baseball player making less than $2,000 a month, Ryan is now worth over $100 million. He shares his experiences in building wealth and believes that anyone can change their life with real estate investing. ...
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