Cash Flow Positive

What do you do when a property isn’t performing—and how do you know if it’s time to cut your losses or hold tight and turn it around?In today’s episode of the Cash Flow Positive Podcast, Kenny Bedwell offers a grounded, practical perspective on one of the toughest situations a real estate investor can face: owning a short-term rental that just isn’t working. Drawing from real-world examples and lessons learned from clients across the U.S., Kenny walks through the key questions to ask before rushing to sell, and the most common (and fixable) issues holding properties back.You’ll learn why immediate selling is often premature, how to calculate the true value of tax savings and appreciation, and what steps to take to improve revenue without over-investing. Whether you're breaking even, losing a little, or just frustrated with underperformance, this episode is packed with insight to help you analyze, adjust, and move forward with 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 not all underperforming properties are “bad” investmentsHow to avoid locking in unnecessary losses by selling too soonWhat to analyze before deciding to exit a propertyWhy tax savings, equity paydown, and appreciation still matterThe top 3 levers to increase STR revenue—and how to check themHow to remove personal bias and get honest feedback on your propertyWhen it does make sense to sell—and how to do it strategicallyWhat seasoned investors know about failure and learning from mistakesAnd much more...Resources:Connect with Kenny on LinkedInFollow Kenny on Instagram

What happens when you take a massive design risk on a short-term rental—and it turns into your most profitable investment ever?In today’s episode of the Cash Flow Positive podcast, Kenny Bedwell welcomes Ashley Guy, a short-term rental investor, mom of six, agent, coach, and creative powerhouse behind one of the most unique Airbnbs in the U.S. Ashley shares the full story behind her now-famous “kink cabin” in Gatlinburg, Tennessee—a bold, adult-themed STR that grosses six figures annually and books out months in advance.Ashley reveals the challenges of designing a fully immersive, highly targeted guest experience—from sourcing custom furniture to marketing without relying on traditional channels. She also breaks down why most investors play it too safe, how to stand out in saturated markets like Gulf Shores, and what it really takes to create properties that command premium rates and loyal repeat guests.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 the “kink cabin” idea was a strategic investment, not a gimmickHow Ashley made over $80K net on a $333K cabin in just one yearThe power of immersive design and what most hosts missHow to turn judgment and taboo into brand loyalty and bookingsWhy niche STRs outperform copy-paste properties in saturated marketsThe role of guest avatars and how to truly design for themHow Ashley scales her creativity across multiple markets and property typesWhy “commit and figure it out” is a mindset every STR investor needsAnd much more...Resources:Connect with Kenny on LinkedInFollow Kenny on Instagramthefemmeinvestor.com Contact Ashley at ashley@thefemmeinvestor.com 

What makes a short-term rental not just good, but unforgettable—and why do the most unique properties often deliver the biggest returns?In today’s episode of the Cash Flow Positive Podcast, Kenny Bedwell explores how creating wildly unique properties can lead to massive success in the short-term rental market. Instead of copying cookie-cutter designs, Kenny explains why the most profitable hosts think differently: they go all in on targeting a specific guest avatar and design unforgettable experiences that guests will remember—and rebook.Drawing inspiration from the world’s most unique Airbnbs, Kenny shares the strategies behind selecting the right market, crafting experiences guests actually want, and making smart, strategic design choices. He also highlights the risks of generic, templated properties and why deep research, creativity, and bold execution separate the best rentals from the rest.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 wildly unique short-term rentals often achieve the best returnsHow to identify and design for your specific guest avatarWhy "selling an experience" matters more than adding more amenitiesHow strategic, memorable features boost bookings and brand recognitionThe dangers of copy-paste designs—and how to avoid blending into the crowdWhy standing out is critical in saturated rental marketsHow going “all in” with your property creates an undeniable competitive edgeWhy half-hearted design efforts cost more than they saveAnd much more...Resources:Connect with Kenny on LinkedInFollow Kenny on InstagramThe Pumpkin Plan: A Simple Strategy to Grow a Remarkable Business in Any Field

Are you navigating real estate deals without fully understanding the risks—or worse, putting yourself in legal jeopardy?In today’s episode of the Cash Flow Positive Podcast, Kenny Bedwell welcomes Parker Borofsky, an experienced investor and short-term rental lending expert, to unpack some of the hottest—and riskiest—topics in real estate today. From the realities of seller credits and subject-to deals to the right (and wrong) ways to use LLCs for property ownership, Parker shares real-world advice, practical examples, and key lending insights that every investor needs to hear.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 can put you at risk of mortgage fraudWhat most people misunderstand about subject-to deals—and why they’re riskyThe truth about transferring properties into LLCs (and when it’s allowed)Why changing title ownership doesn’t automatically trigger alarms with lendersHow DSCR loans and non-QM loans actually work—and their hidden challengesWhy working with knowledgeable lenders can protect you from costly mistakesHow failing to strategize your debt-to-income ratio could limit your growthWhy talking to the right lender early can open up more opportunities than you thinkAnd much more...Resources:Connect with Kenny on LinkedInFollow Kenny on InstagramWealth Builders Mortgage Group

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