Cash Flow Positive

Are you making investment moves that could unknowingly cross the line into mortgage fraud?In today’s episode of the Cash Flow Positive Podcast, Kenny Bedwell breaks down some of the hottest (and riskiest) real estate strategies being pushed today—from seller credits to subject-to deals to buying properties under LLCs. Kenny reveals what’s truly legal, what’s risky, and what could get investors into serious trouble if not handled properly.Packed with practical examples, actionable advice, and a no-nonsense breakdown of gray areas in real estate, this episode will help you stay compliant, protect your investments, and build a smarter portfolio.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 improperly handling seller credits could land you in legal troubleWhat actually constitutes mortgage fraud—and how to avoid itThe difference between seller concessions and seller creditsWhy working with the wrong agent can expose you to major riskHow "subject-to" deals work—and why they’re riskier than they appearWhy buying properties in LLCs doesn’t always offer the protection you thinkThe smarter way to move a property into an LLC without hurting your financingHow to set up a safe, compliant strategy when investing in gray areasAnd much more...Resources:Connect with Kenny on LinkedInFollow Kenny on Instagram

What if global economic decisions could reshape the future of your short-term rental investments?In this solo episode of the Cash Flow Positive podcast, Kenny Bedwell dives deep into the ripple effects of tariffs, presidential policies, and tax changes—and how they’re likely to impact STR markets across the U.S.Drawing on his economics background and personal real estate experience, Kenny breaks down the macroeconomic trends in simple, real-world terms. From potential shifts in consumer travel habits to the implications of bonus depreciation and fluctuating interest rates, this episode provides actionable insights for anyone looking to navigate today’s uncertain economic climate with strategy and confidence.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 macroeconomic changes don’t impact every STR market the same wayHow tariffs could influence STR demand in driving vs. flying destinationsWhy now might be a good time to invest in real estate (if you do it smart)What to expect from potential tax changes and bonus depreciationHow to evaluate your STR’s position in the market to determine riskWhy fear-based headlines might not apply to your unique situationThe importance of buying with a strategy—and a moatHow occupancy and ADR play different roles in your revenue storyAnd much more...Resources:Connect with Kenny on LinkedInFollow Kenny on Instagram

What happens when your Airbnb guest sues you—and are you actually protected?In this episode of Cash Flow Positive podcast, Kenny Bedwell invites tax attorney and strategic advisor Anthony Brister to share crucial insights into asset protection, estate planning, and insurance—especially for short-term rental (STR) investors.Anthony, founder of the Brister Law Firm, breaks down the levels of legal and financial protection STR operators should consider, from forming the right kind of LLC to understanding when it makes sense to consider charging order protection entities, umbrella policies, or trusts.Together, Kenny and Anthony dissect real-world strategies for STR investors looking to protect their assets while growing their portfolios the smart way. They also share stories—like Kenny’s own experience of being sued by a guest—that bring home the urgency of getting your protection and paperwork in place before problems arise.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 setting up an LLC is not enough—and what formalities you must follow to actually be protectedHow to layer your protections over time as your STR portfolio growsWhat a revocable trust really protects—and why it's about more than just assetsHow the state where you form your LLC could make or break your legal shieldThe single most overlooked insurance mistake STR investors makeWhat umbrella policies do (and don’t) cover in real-life lawsuitsHow to time a deed transfer to an LLC without raising red flagsWhen it's worth considering advanced tools like family limited partnerships or irrevocable trustsWhy asset protection is about planning ahead—not reacting too lateAnd much more...Resources:Connect with Kenny on LinkedInFollow Kenny on InstagramBrister Law Firm, PLLC 

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