Cash Flow Positive

What do you do when your Airbnb guest sues you—and the case drags on for years? In this solo episode of Cash Flow Positive, Kenny Bedwell shares the behind-the-scenes story of a lawsuit that caught him off guard, how he navigated the legal chaos, and the surprising truth about LLC protection and short-term rental insurance.This isn’t just a cautionary tale—it’s a wake-up call for every real estate investor who thinks they’re safe behind an LLC. Kenny breaks down exactly what happened, why it matters, and how you can avoid the stress and financial risk that comes with unexpected accidents, lawsuits, and worst-case scenarios.If you’re investing in STRs or planning to, this episode is essential listening. From legal layers to loss-of-income coverage, Kenny walks you through the lessons he learned the hard way—so you don’t have to.If you've enjoyed this episode of the Cash Flow Positive podcast, be sure to leave a review and subscribe today! Listen now and enjoy!In This Episode You'll Learn:Why your LLC might not protect you the way you think it doesWhat to do immediately if a guest is injured at your propertyThe most underrated mistake STR investors make about insuranceHow to assess the right coverage for your risk level and marketWhy loss-of-income coverage is non-negotiable in disaster-prone areasThe tipping point when you should start building layered asset protectionWhy having a great attorney isn’t enough—they need to review your policies tooAnd much more...Resources:Connect with Kenny on LinkedInFollow Kenny on Instagram

Are you truly ready to launch your next short-term rental—or are you overlooking the hidden costs that could derail your returns?In this episode of Cash Flow Positive, Kenny Bedwell continues the conversation on hard-earned lessons from the field, offering raw and practical advice every STR investor should hear. This isn’t just theory—it’s a behind-the-scenes look at what really happens when properties take longer to launch, when holding costs spiral, and when “almost guest-ready” just isn’t good enough.Drawing from his own projects, Kenny breaks down what many investors miss when budgeting for renovations, managing out-of-state setups, and relying too heavily on contractors without local oversight. He also digs deep into market conditions, sharing what he’s seeing as the industry matures, where opportunity still lies, and why having a “moat” around your investment is more crucial than ever.If you've enjoyed this episode of the Cash Flow Positive podcast, be sure to leave a review and subscribe today! Listen now and enjoy!In This Episode You'll Learn:Why having boots on the ground can make or break your STR setupWhat it really takes to get a property fully guest-ready—not just 90% thereHow to build a “moat” around your STR and avoid constant reinvestment battlesWhen seller credits work—and when they’re just smoke and mirrorsHow to prepare for appraisal gaps and navigate unrealistic seller expectationsWhy you should test everything—including toilets and outlets—before launchingWhat STR investors often overlook when assessing resale valueHow to avoid getting lured into overpriced “super properties”Why now might be a better time to buy than later this yearWhat maturing markets mean for buyers, sellers, and long-term investorsAnd much more...Resources:Connect with Kenny on LinkedInFollow Kenny on InstagramSTR Insights YouTube channel Part 1: Types of STR Markets No One is Talking About

What does it really take to launch a short-term rental successfully—when things don’t go as planned? In this solo episode of Cash Flow Positive, Kenny Bedwell pulls back the curtain on two recent STR setup experiences that tested his patience, budget, and systems.Kenneth shares everything he learned while launching properties in Asheville and Kentucky, including working with designers, managing contractors, and navigating delays, disasters, and unexpected design decisions. One project turned into a complete nightmare, with miscommunications, missed deadlines, and a designer who ghosted him in the middle of the process. The other? A more streamlined—but still challenging—process that highlighted the value of clear communication, strong referrals, and aligned teams.If you’ve ever thought about hiring a designer or project manager to help launch an STR—or wondered what pitfalls to avoid—this episode delivers a firsthand look at what not to do and what you can do instead to protect your investment and timeline.If you've enjoyed this episode of the Cash Flow Positive podcast, be sure to leave a review and subscribe today! Listen now and enjoy!In This Episode You'll Learn:Why hiring a designer isn’t enough—and what you actually need them to doHow to avoid costly delays when setting up a short-term rentalThe one mistake that caused a project to go totally off the railsWhy referrals and vetting are non-negotiable for anyone on your teamWhat happens when designers and contractors aren’t in syncHow small miscommunications lead to big issues (and how to fix them)The lessons learned from a 10,000 sq ft STR project in KentuckyWhy some STR entrepreneurs are choosing in-house design and build teamsAnd much more...Resources:Connect with Kenny on LinkedInFollow Kenny on Instagram

What if you could invest in STRs where demand never dries up—without competing in oversaturated vacation markets? In this episode of Cash Flow Positive, Kenny Bedwell sits down with Maria Reith, an experienced STR investor who has built a thriving rental portfolio in military towns, including Dayton, Ohio, and San Antonio, Texas.Maria didn’t start with a background in real estate—she began investing as a way to prepare for retirement. But what started as a simple strategy quickly scaled into over 30 properties in some of the most stable STR markets available: military towns.She reveals why military bases create consistent rental demand, how she balances short-term, midterm, and long-term rentals, and why word-of-mouth marketing plays a huge role in her success. Maria also shares her approach to creative financing, how she finds value-add properties, and the one thing investors should always research before buying near a military base.If you're looking for new STR markets with steady cash flow, this episode will open your eyes to a powerful, under-the-radar investment strategy. Listen now and njoy!In This Episode You'll Learn:How military towns offer consistent demand for STRs, even when vacation spots are saturatedWhy proximity to military bases can be key for STR profitabilityThe importance of buying properties with value-add potential for maximum returnsHow to balance between short-term, midterm, and long-term rentals to optimize cash flowWhy word-of-mouth and community engagement are crucial for military-based STR businessesHow Maria uses creative financing to scale her STR portfolioHow to evaluate the future stability of military bases and the surrounding real estate marketWhy Maria’s exit strategy involves preparing for long-term rental cash flowAnd much more...Resources:Mariareith.com Connect with Kenny on LinkedInFollow Kenny on Instagram

What if you could invest in short-term rentals without competing in oversaturated vacation markets? In this episode of Cash Flow Positive, host Kenny Bedwell challenges the idea that STR success is only found in traditional vacation destinations. Instead, he explores alternative STR markets that offer consistent demand, fewer competitors, and strong cash flow opportunities.Drawing from his own experience setting up two STR properties—a 5-bedroom renovation project and a rental on the Bourbon Trail in Kentucky—Kenny shares the realities of launching an STR outside the usual hotspots. He explains why vacation rental markets aren’t the only profitable options and breaks down key STR opportunities in less obvious locations, including college towns, military towns, state parks, and urban areas near hospitals.Throughout the episode, Kenny highlights how investors can leverage these markets to reduce risks, secure better returns, and manage seasonality more effectively. He also discusses exit strategies and the importance of adaptability when investing in these unique STR locations.This episode is a must-listen for anyone looking to expand their STR portfolio without getting caught in the vacation rental bubble.In This Episode You'll Learn:Why short-term rental markets go beyond vacation destinationsHow overlooked STR markets can offer better cash flow and stabilityWhat makes college towns a strong, steady investment choiceWhy military towns are ideal for short- and mid-term rental demandHow state parks have become an unexpected STR hotspotWhy STRs near hospitals can provide year-round bookingsHow to evaluate exit strategies in different STR marketsWhat investors should consider before entering these less obvious locationsAnd much more…Resources:Connect with Kenny on LinkedInFollow Kenny on Instagram

How do you scale from a single short-term rental to managing over 30 properties and owning a boutique hotel? In this episode, Kenny is joined by Tony Stancato, Founder of Book N' Gather Property Management. He shares how he leveraged partnerships, operational expertise, and a strategic mindset to build a thriving STR business in Southwest Michigan.Tony walks us through his journey—from buying his first vacation rental in 2021 to managing a diverse portfolio that includes single-family homes, multi-unit properties, and now a boutique motel. He reveals the keys to finding great deals, structuring partnerships, and navigating the challenges of short-term rental investing.Whether you're just starting out or looking to scale your STR portfolio, this episode is packed with practical insights on building a business that creates wealth, not just cash flow. If you've enjoyed this episode of the Cash Flow Positive podcast, be sure to leave a review and subscribe today! Listen now and enjoy!In This Episode You'll Learn:Why partnerships can accelerate growth and unlock bigger dealsThe mindset shift needed to go from one rental to a full-scale businessHow networking and sharing your journey can lead to unexpected opportunitiesThe importance of structuring a property management company for long-term successWhy successful investors focus on both cash flow and appreciationHow short-term rental markets like Southwest Michigan offer untapped potentialAnd much more…Resources:Connect with Kenny on LinkedInFollow Kenny on InstagramConnect with Tony on LinkedInMichigan Short Term Rentals PodcastMichiganSTRConference.com 

Scaling a real estate portfolio isn’t just about buying more properties—it’s about strategic growth, partnerships, and mindset shifts. In this solo episode of Cash Flow Positive, Kenny Bedwell shares his personal journey of scaling his short-term rental business, highlighting the biggest challenges, lessons, and strategies that helped him go from his first investment to a sustainable, cash-flowing portfolio.Kenny emphasizes the importance of starting small, taking action, and not waiting for the “perfect” opportunity. He also discusses why defining what scaling means to you is crucial before making your next investment decision. Additionally, he breaks down why partnerships and collaborations are the key to overcoming capital constraints and how to navigate the quantity vs. quality debate when expanding your portfolio.If you’re looking to grow your STR investments but feel stuck, this episode provides a clear roadmap for taking the next step—whether that’s buying your first property, securing funding for expansion, or building strategic partnerships to accelerate growth. Enjoy!In This Episode You'll Learn:Why you don’t need a massive budget to start investing in STRsThe biggest mistake investors make when scaling—and how to avoid itWhy taking action is more important than waiting for the “perfect” opportunityHow defining your vision of success will dictate your investment strategyThe power of partnerships in overcoming capital constraintsScaling isn’t just about adding more properties—it’s about smart growthHow to balance quality vs. quantity when expanding your portfolioWhy patience and long-term thinking are key to achieving sustainable successAnd much more…Resources:Connect with Kenny on LinkedInFollow Kenny on Instagram

What if you could increase bookings and nightly rates just by adding the right amenities? In this episode of Cash Flow Positive, Kenny Bedwell is joined by short-term rental expert Jose Cornejo to break down the real impact of STR amenities—and how to choose the ones that actually move the needle.With 18+ years of experience in the STR industry, Jose has built and managed lakefront homes in the Poconos, beachfront rentals in the Outer Banks, and additional properties in Kentucky. He started before Airbnb and Vrbo even existed, learning firsthand how smart pricing, marketing, and amenities can turn a property into a revenue-generating machine.Jose shares his insights on why not all amenities increase revenue, how seasonal upgrades can impact demand, and why marketing your amenities properly is just as important as offering them. He also discusses the biggest mistakes investors make when upgrading their properties and how to create an experience that justifies premium pricing.If you’re looking for data-backed strategies to maximize revenue and optimize guest experience, this episode will help you stand out in the crowded STR market and boost your bottom line. Enjoy!In This Episode You'll Learn:How strategic amenities increase bookings and nightly ratesWhy pictures are just as powerful as physical amenitiesThe surprising impact of seasonal amenities on guest demandHow to create a guest experience that justifies premium pricingWhy marketing your amenities properly is the real game-changerHow investing in the right upgrades can pay off quicklyAnd much more…Resources:Connect with Kenny on LinkedInFollow Kenny on InstagramConnect with Jose on LinkedInCornejoRentals.com 

Which amenities actually increase revenue in short-term rentals—and which ones are just a waste of money? In this solo episode of Cash Flow Positive, Kenny Bedwell breaks down the three types of amenities that move the needle: those that increase occupancy, boost ADR (average daily rate), or improve guest experience.Kenny shares real data and case studies on what amenities truly impact bookings and pricing, revealing the biggest mistakes hosts make when choosing upgrades. He also explains how to market amenities effectively, why seasonal amenities can be a game-changer, and how five-star reviews directly impact revenue.If you’re thinking about investing in amenities to stand out in a crowded market, this episode will help you make the smartest decisions to maximize profits.In This Episode You'll Learn:The three types of amenities: occupancy boosters, ADR boosters, and guest experience enhancersWhy not all amenities increase revenue—and how to identify the ones that doThe impact of seasonal amenities and when they actually generate bookingsHow to market your amenities properly to get the most value out of themWhy five-star reviews are worth $189 each—and how to get more of themHow small guest experience improvements can significantly impact long-term revenueAnd much more…Resources:Connect with Kenny on LinkedInFollow Kenny on InstagramEpisode Mentioned:Part 2: How to buy deals out-of-state with Jeana Deninger

What’s the key to long-term success in real estate investing? It’s not just about strategy—it’s about the people you surround yourself with. In this episode of Cash Flow Positive, Kenny welcomes Tanya Rooney, a seasoned investor and short-term rental expert, to dive into the power of community, accountability, and networking in building a thriving business.With 17+ years in real estate, Tanya has built a successful career in commercial real estate, flipping, and STR investing—but she credits her biggest wins to the relationships she’s built along the way. She reveals how masterminds, accountability groups, and surrounding yourself with the right people can accelerate success, plus the hard lessons she learned from a motel deal gone wrong.Whether you’re just starting out or scaling your investments, this episode will give you actionable insights on leveraging relationships to build wealth faster. If you've enjoyed this episode of the Cash Flow Positive podcast, be sure to leave a review and subscribe today!Enjoy!In This Episode You'll Learn:Why accountability groups are a game-changer for real estate investorHow surrounding yourself with the right people accelerates successThe importance of celebrating wins instead of always chasing the next goalHow networking in mastermind groups can save you from costly mistakesThe key differences between STRs and boutique hotels—and why it mattersHow effective communication can prevent revenue loss in STRsAnd much more…Resources:Connect with Kenny on LinkedInFollow Kenny on InstagramTribe Builders PodcastConnect with Tanya on LinkedIn