Cash Flow Positive

Rates are high, inventory is tight, and opinions are all over the place—so is now actually a good time to buy a property? In this episode, Kenny Bedwell sits down with mortgage expert Brenna Carles to cut through the confusion and answer the big question: Is it really a buyers' market? They dive into hard truths about investing, bust common excuses, and offer no-nonsense guidance on how to make decisions based on data, not drama.Brenna shares her perspective as someone who helps investors build wealth through real estate financing—and as someone who doesn't shy away from calling it like it is. Whether you're waiting for rates to drop, unsure if you should refinance, or just feeling paralyzed by market uncertainty, this episode will give you the clarity and confidence you need.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:The reality of fluctuating interest rates and what it means for your investment plansHow to approach refinancing with realistic expectations and avoid being caught off guardWhy the housing market isn't as “bad” as it may seem for investors willing to act strategicallyWhat's driving the market: understanding the difference between residential and short-term rental dynamicsWhy you should stop making excuses and start taking action if the numbers work for youHow the 100% bonus depreciation change could affect short-term rental investment strategiesThe importance of building reserves and being financially prepared for unexpected costsAnd much more...Guest Bio: Brenna Carles is the CEO and founder of The Mortgage Shop, specializing in short-term rental, long-term rental, and vacation home loans. With over $600 million in loan volume closed, Brenna is one of the top brokers in the industry and a trusted resource for investors navigating complex financing landscapes. She's passionate about educating and empowering her clients to make informed decisions and build sustainable wealth through real estate. Brenna is also known for her work on creating solutions for real estate investors, particularly in managing financing in today's shifting market conditions.Resources:Connect with Kenny on LinkedInFollow Kenny on Instagrammortgage.shop Follow Brenna on FacebookDisclaimer: The views, information, or opinions expressed during this podcast are solely those of the individuals involved and do not necessarily represent those of the Cash Flow Positive podcast or its affiliates. The content provided is for informational and entertainment purposes only and is not intended to be a substitute for professional advice. We make no representations as to the accuracy, completeness, suitability, or validity of any information on this podcast and will not be liable for any errors, omissions, or delays in this information or any losses, injuries, or damages arising from its display or use. Listeners should consult with a professional for specific advice tailored to their situation. By accessing this podcast, you acknowledge that any reliance on the content is at your own risk.

Everyone's talking about a "buyer's market"—but is that really what we're seeing in short-term rental real estate right now? In this episode, Kenny Bedwell explores whether today's environment truly favors buyers or if the opportunity is more nuanced. He breaks down current market dynamics, challenges assumptions, and reveals what it actually takes to land a great STR deal right now.He explores why short-term rentals remain a viable long-term investment, even when buyer competition, pricing dynamics, and interest rates fluctuate. This episode provides a grounded perspective on when and why to make a move, and what “timing the market” actually looks like in real estate.Whether you're considering your first STR or evaluating your next acquisition, this episode offers the strategic lens you need to cut through the noise.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 a slower buyer's market could mean better deals for STR investorsWhat makes “the best deals” move off-market quicklyHow bonus depreciation can drive market activity toward year-endThe two components you must consider beyond just price or revenueWhy short-term rentals are not a trend, but a lasting piece of the economyWhat it takes to ride out challenges in any market cycleHow to think long-term while spotting near-term opportunitiesAnd much more...Resources:Connect with Kenny on LinkedInFollow Kenny on InstagramDisclaimer: The views, information, or opinions expressed during this podcast are solely those of the individuals involved and do not necessarily represent those of the Cash Flow Positive podcast or its affiliates. The content provided is for informational and entertainment purposes only and is not intended to be a substitute for professional advice. We make no representations as to the accuracy, completeness, suitability, or validity of any information on this podcast and will not be liable for any errors, omissions, or delays in this information or any losses, injuries, or damages arising from its display or use. Listeners should consult with a professional for specific advice tailored to their situation. By accessing this podcast, you acknowledge that any reliance on the content is at your own risk.

With the short-term rental market evolving rapidly, simply following the old playbook won't cut it anymore. In this episode of Cash Flow Positive, Kenny Bedwell breaks down what the future of STR investing really looks like—and it's not for the faint of heart. From industry-wide professionalization to a rising demand for uniqueness, he outlines what successful hosts need to know (and do) to stay competitive.Kenny shares his insights into how STRs are becoming more commercial and why that calls for more strategic, long-term investment thinking. This episode is a deep dive into shifting your mindset to hospitality professional—and building properties that people will rave about.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 STR investing today requires a different approach than even a few years agoHow the industry is becoming more commercial and what that means for hostsWhy five-star reviews are no longer the gold standard—repeat guests areHow to build properties that can't be easily replicatedWhat “stacking amenities” really means—and how to do it wellThe importance of targeting your ideal guest with intentional designWhy your cash-on-hand matters more than your lender's pre-approvalHow to create a STR investment that will stand the test of timeAnd much more...Resources:Connect with Kenny on LinkedInFollow Kenny on InstagramDisclaimer: The views, information, or opinions expressed during this podcast are solely those of the individuals involved and do not necessarily represent those of the Cash Flow Positive podcast or its affiliates. The content provided is for informational and entertainment purposes only and is not intended to be a substitute for professional advice. We make no representations as to the accuracy, completeness, suitability, or validity of any information on this podcast and will not be liable for any errors, omissions, or delays in this information or any losses, injuries, or damages arising from its display or use. Listeners should consult with a professional for specific advice tailored to their situation. By accessing this podcast, you acknowledge that any reliance on the content is at your own risk.

How do you know your short-term rental is actually legal, and not one neighbor complaint away from a lawsuit?In today's episode of the Cash Flow Positive podcast, Kenny Bedwell is joined by Katie Johnson, a real estate attorney and investor, to break down one of the most misunderstood legal threats in the short-term rental world: deed restrictions. Whether you're operating in Michigan or buying in Texas, these buried clauses in your title documents could override local STR-friendly zoning and put your entire business at risk.Katie explains the difference between deed restrictions and HOA rules, why “residential use only” language matters, how to spot red flags in your title work, and the limited defenses available if a neighbor sues. They also discuss what title insurance really covers, when to bring in an attorney, and how to protect yourself before closing.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:What deed restrictions actually are, and how they differ from zoning lawsWhy a city permit doesn't protect you from private enforcementHow to find and interpret deed restrictions in your title workWhat to do if you discover a restriction after closingWhy Katie always requests title work on day one of due diligenceHow to use contingencies to protect your deal before it's too lateWhy talking to your neighbors might save your investmentThe real risks of buying in unregulated STR marketsAnd much more...Guest Bio: Katie Johnson is a real estate attorney, investor, and founder of Katie Johnson, PLC, a Michigan-based law firm specializing in real estate and business law. She's licensed in Michigan and Illinois, with a pending license in Indiana, and works closely with investors and short-term rental operators on everything from contract review to regulatory strategy. Known for her practical, investor-minded approach, Katie also speaks at conferences across the country and is an advocate for proactive legal planning in real estate. Her goal is to help property owners navigate regulations with confidence and clarity—before it's too late.Resources:KatieJohnsonPLC.com Connect with Kenny on LinkedInFollow Kenny on Instagram

Just because you have a permit doesn't mean your short-term rental is actually legal.In today's episode of the Cash Flow Positive podcast, Kenny Bedwell shares a real-life cautionary tale that every STR operator needs to hear. After working with a client who discovered a deed restriction after closing on a property, Kenny breaks down how these restrictions work, why title companies won't protect you, and how neighbor relationships can make or break your rental's future.But this episode isn't just about legal definitions—it's about prevention, strategy, and people. Kenny dives into what you should do before you buy, how to read the fine print, and most importantly, how to build lasting trust with neighbors who have the power to shut you down.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:What deed restrictions are and why they matter more than zoningWhy title companies don't flag every STR risk in advanceHow a neighbor lawsuit can override your city permitWhat to ask for in your title documents before closingHow to talk to neighbors before and after you purchaseWhy good relationships can protect you from legal troubleHow to turn STR-haters into direct booking alliesThe mindset that keeps your business safe—and your neighbors happyAnd much more...Resources:Connect with Kenny on LinkedInFollow Kenny on Instagram

What does it take to turn a direct booking website into a real revenue driver?In today's episode of the Cash Flow Positive Podcast, Kenny Bedwell is joined by Gil Chan, tech founder, short-term rental host, and the creator of CraftedStays—a platform that helps STR hosts easily build customizable direct booking sites without breaking the bank.Drawing on his background in e-commerce, Gil walks through the parallels between retail and hospitality, explains how to structure a site that actually converts, and shares his strategies for guest vetting, trust-building, and long-term nurture campaigns. He breaks down what most hosts get wrong about direct bookings, and what to focus on instead—starting with knowing your ideal guest avatar and optimizing every piece of the guest journey around them.From lead magnets and email flows to the psychology of brand visibility, this episode is packed with insights on how to grow your direct bookings sustainably—without trying to master every marketing channel at once.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 e-commerce and STRs are more similar than you thinkWhat your direct booking site must include to build trust and convert visitorsHow to structure your site around your “guest avatar”What most STR owners misunderstand about branding and professionalismHow to handle guest vetting on direct booking platformsWhy starting small (with the right tools) beats outsourcing everythingGil's favorite ways to collect and nurture guest emails automaticallyWhat a good year-one direct booking rate looks like—and how to scale itAnd much more...Guest Bio: Gil Chan is a short-term rental host, tech entrepreneur, and founder of CraftedStays—a platform that makes it easy for hosts to build fully integrated, conversion-focused direct booking websites. With a background as a product director in e-commerce, Gil saw the gap between STR operators and the tech tools they needed to take control of their businesses. After building the first version of CraftedStays for his own properties, he left his six-figure job in tech to grow the company full-time. Today, Gil helps hosts across the U.S. build their brands, attract the right guests, and increase revenue—one click at a time.Resources:Connect with Kenny on LinkedInFollow Kenny on InstagramConnect with Gil on LinkedInCraftedStays.co The Ultimate Guide to Direct BookingsBooked Solid Podcast

Should you take direct bookings—and what does it take to make them work?In today's episode of the Cash Flow Positive podcast, Kenny Bedwell unpacks the real considerations behind building a direct booking strategy. While many hosts focus on software and site setup, Kenny zeroes in on the biggest challenge: attracting the right traffic. He explains how to create repeat business, leverage your property's location, and build trust with potential guests—without relying on OTAs.You'll learn how to think in terms of guest journeys, content marketing, and simple tactics like email and signage to grow your brand over time. Whether you're just starting to consider direct bookings or trying to make an existing strategy more effective, this episode offers clear, actionable guidance on how to do it right.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:The top three concerns people have with direct booking sitesHow to identify and market to your “warm” and “cold” traffic segmentsWhy repeat business is more powerful (and cheaper) than new trafficSimple ways to promote your brand inside your propertyHow to use email and social to stay top-of-mind year-roundWhy promoting your market, not your property, builds trustHow lead magnets and content marketing drive real resultsAnd much more...Resources:Connect with Kenny on LinkedInFollow Kenny on Instagram

Are you pricing your short-term rental based on facts—or just following what everyone else is doing?In today's episode of the Cash Flow Positive podcast, Kenny Bedwell sits down with Jake Cohen, founder of Step By Step BNB and a seasoned revenue manager overseeing 300+ listings. Together, they unpack the real strategies behind sustainable revenue, debunking myths and simplifying key concepts like RevPAR, booking windows, and market dynamics.Jake breaks down the difference between pricing for high and low seasons, why most hosts underestimate the power of good photography, and what it really means to “be booked first” when it matters most. He also explains how to calculate and interpret RevPAR, set minimum night stays with intention, and use tools like PriceLabs to monitor real-time market behavior.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 RevPAR is Jake's #1 metric for STR healthHow to adjust your pricing based on seasonality and demandWhy minimum night stays should change based on booking windowsWhat most hosts get wrong about high vs. low season pricingHow to calculate your property's RevPAR (and why it matters)Why listing optimization is just as important as price strategyHow to simplify your pricing—and book more with less effortAnd much more...Resources:Connect with Kenny on LinkedInFollow Kenny on InstagramStep By Step BNB Price Your STR Facebook Group

What if the real problem with your revenue isn't your price—it's your mindset?In today's episode of the Cash Flow Positive podcast, Kenny Bedwell breaks down exactly why so many hosts struggle with pricing—and how to turn things around with consistent, proactive revenue management. From hiring a revenue manager to leveraging tools like PriceLabs, Kenny shares what works, what doesn't, and why “just dropping your price” is the fastest way to lose control of your numbers.You'll hear why minimum night stays are a hidden lever, how to adjust to low-season buyer behavior, and why your average daily rate (ADR) and occupancy must be evaluated together. Kenny also talks about the “potato chip pricing strategy,” a simple analogy that can help you figure out where your property stands in the market—and how to price accordingly, without emotion or ego.Whether you're overwhelmed by dynamic pricing or trying to recover from poor performance, this episode will give you the clarity and tools to make smarter pricing decisions going forward.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 revenue manager might be the smartest investmentHow to stop reacting and start planning when bookings slow downWhy “dropping prices” isn't a strategy—it's a symptomHow to use minimum night stays to drive more bookingsThe difference between revenue, ADR, and occupancy—and why it mattersHow seasonality affects guest behavior and price sensitivityThe mindset shift that separates consistent earners from frustrated hostsAnd much more...Resources:Connect with Kenny on LinkedInFollow Kenny on Instagram

What do you do when you buy a short-term rental, and it just doesn't perform?In today's episode of the Cash Flow Positive Podcast, Kenny Bedwell welcomes Erik Courson, an STR investor, tech enthusiast, and data-driven host, to share the honest story of how he bought a property at the peak of the market—and what he did when it started bleeding cash. In this open, numbers-first conversation, Erik walks us through the decisions that led to the purchase, the surprises he encountered, and the strategies that helped him go from a projected $30K loss to breakeven performance.From redesigning a forgettable cabin in Blue Ridge, Georgia, to implementing revenue management tools and facing hard truths about sunk costs and missed expectations, Erik lays out what really works when you're trying to fix a less-than-ideal deal. He also reflects on the emotional toll of managing underperformance, the benefits of holding vs. selling, and why STR investors should embrace humility and adaptation.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:How Erik turned a projected $30K loss into breakeven performanceWhat to do before deciding to sell an underperforming propertyWhy “locking in your losses” is often the most expensive mistakeHow niche positioning and small design changes can drive bookingsWhy emotion and market timing can lead smart investors astrayHow to use technology and AI to spot blind spots and hidden issuesWhat Erik learned from investing in two very different STR marketsWhy community, critique, and clarity matter more than quick winsAnd much more...Resources:Connect with Kenny on LinkedInFollow Kenny on Instagram

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

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

What's the real secret to long-term success in real estate investing? It's not just about the numbers—it's about understanding your progress, defining success, and fueling momentum for the next step. In this solo episode of Cash Flow Positive, Kenny Bedwell shares his personal secret weapon for success, reflecting on how far he's come and why taking time to acknowledge wins is essential for continued growth.Kennt discusses how mindset, gratitude, and self-reflection play a huge role in building and scaling a real estate portfolio. He also reveals his latest big investment move—a $1.5M boutique hotel—and how shifting his perspective helped him take on challenges he never imagined a year ago.If you're looking for more than just investment strategies and want to build a mindset that drives success, this episode will help you reframe how you measure progress, set goals, and push past your limits.In This Episode You'll Learn:Why success isn't just about hitting big milestones—it's about progressThe power of gratitude and self-reflection in business growthHow defining your “why” helps guide smart real estate decisionsWhy tracking your achievements fuels momentum for bigger opportunitiesHow surrounding yourself with the right people accelerates successKenny's personal experience with scaling investments and taking on new risksAnd much more…Resources:Connect with Kenny on LinkedInFollow Kenny on Instagram

Buying out-of-state rental properties can feel like a gamble—so how do you ensure success and avoid costly mistakes? In this episode of Cash Flow Positive, Kenny Bedwell is joined by Jeana Deninger, an experienced short-term rental investor and consultant. With properties in Maine, Florida, and beyond, Jeana has mastered the art of managing STRs from a distance, ensuring they remain profitable while maintaining high guest satisfaction.Jeana shares the critical steps every investor should take when purchasing and managing out-of-state properties, from choosing the right markets and assembling a reliable local team to marketing effectively and optimizing guest experiences. She also discusses common mistakes investors make and the red flags to watch for when working with property managers, cleaners, and maintenance teams.If you're thinking about expanding your real estate portfolio into new markets, this episode is packed with insider strategies to help you buy, manage, and scale STR properties like a pro. Enjoy! In This Episode You'll Learn:Why hiring the right professionals can make or break your STR businessThe importance of researching local markets and guest expectationsHow to properly vet and manage cleaners, handymen, and house managersThe top mistakes investors make when buying properties sight unseenHow to market your STR to stand out and maximize bookingsWhy you should never skip inspections—and how they can save you thousandsThe smart way to budget for amenities that increase guest satisfaction and ROIAnd much more…Resources:Connect with Kenny on LinkedInFollow Kenny on InstagramSavvyBreezy.com Connect with Jeana on LinkedIn

In this episode of the Cash Flow Positive podcast, Kenny kicks things off with exciting news: the podcast has broken into the Top 100 in iTunes' entrepreneurship category. You'll discover the challenges and strategies for buying real estate out-of-state; properties that aren't just a short drive away but may require a flight or two to reach. Kenny shares practical advice for overcoming the fear of distance and emphasizes the importance of mindset in tackling these investments. You'll learn the key steps, including building a trustworthy acquisition team, with a focus on securing experienced lenders and realtors who are well-versed in short-term rental markets.Whether you're a seasoned investor or just considering your first long-distance deal, this episode lays the groundwork for growing your real estate empire beyond your local market.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:The importance of overcoming the fear and limiting mindset associated with buying out-of-state.Why you should always connect with the right acquisition team when buying out-of-state properties.The concept of Planned Unit Developments (PUDs) and the unique lending challenges they present.How having a quality control person can reduce the stress and hassle of managing out-of-state properties.And much more...Resources:Connect with Kenny on LinkedInFollow Kenny on Instagram

Are creative financing deals the key to unlocking your next short-term rental, or could they lead you into financial trouble? In this episode of Cash Flow Positive, Kenny Bedwell is joined by seasoned real estate investor Brandon Thompson, who has flipped over 2,000 homes and built a diverse portfolio of short-term rentals, long-term rentals, and commercial properties over the past 21 years.Together, they dive into the real truths behind creative financing in the STR space. Brandon shares his personal experiences with seller financing, Subject-To deals, and owner financing, shedding light on the risks investors often overlook when chasing low-interest deals. He also opens up about pivoting his own portfolio after market saturation and declining returns, and why being intentional with your investments is more important than ever.If you're weighing creative financing options or looking to scale your STR business without getting burned, this episode will arm you with practical advice from a veteran investor who's seen it all. Enjoy!In This Episode You'll Learn:Why creative financing isn't a “one-size-fits-all” solutionHow to structure seller financing and Subject-To deals the right wayThe hidden risks behind “no money down” dealsWhy the glory days of STR investing are over—and how to adaptHow to evaluate your return on equity and know when it's time to pivot.The importance of finding the right market and avoiding oversaturated areasAnd much more…Resources:Connect with Kenny on LinkedInFollow Kenny on InstagramStrwealthbrokers.com SouthernCharmVacay.com Connect with Brandon on LinkedInFollow Brandon on Facebook

In this episode of the Cash Flow Positive podcast, Kenny explores unconventional strategies that can open doors for those looking to make significant moves without following the traditional path.These methods offer flexibility, allowing individuals to bypass common roadblocks while still creating valuable opportunities. However, while these approaches can be highly effective, they also come with unique risks and challenges that must be carefully navigated. You'll learn how these strategies benefit both parties involved, offering potential advantages that aren't typically available in standard agreements. By understanding how to structure these arrangements wisely, individuals can maximize their potential while minimizing exposure to unnecessary pitfalls. At the same time, it's crucial to be aware of the fine print—certain decisions could lead to unexpected consequences if not handled correctly. Whether you're new to this approach or simply looking for ways to refine your strategy, this episode will provide valuable takeaways you won't want to miss.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:Creative financing for STRs, and how it allows direct negotiations with sellers, creating custom terms without the extensive paperwork required by banks.The concept of subject-to financing, where the seller assigns their mortgage to the buyer. Owner financing, a method popular with sellers who don't need immediate cash and want to avoid taxable events from selling.The risks associated with creative financing, including the potential for banks to call the loan if they discover the deed change.And much more...

In this episode of the Cashflow Positive podcast, Kenny is joined by Josh Briner, owner of Vibe Short Term Rental Management.During the conversation, Kenny and Josh emphasize the importance of putting your best foot forward from the start, surrounding yourself with knowledgeable professionals, and making data-driven decisions. They highlight how working with industry experts, leveraging the right tools, and carefully crafting an experience tailored to a target audience can make all the difference.You'll learn the value of looking beyond surface-level costs and considering long-term gains. A conservative but intentional approach to investing in quality can lead to higher returns and a competitive edge. By understanding market demand and focusing on key differentiators, individuals can set themselves apart in an increasingly crowded space.This episode shows that, with a strong foundation and a willingness to adapt, even seemingly daunting landscapes can become profitable and rewarding.If you've enjoyed this episode of the Cashflow Positive podcast, be sure to leave a review and subscribe today!Enjoy!In This Episode You'll Learn:The challenges of managing properties near sports stadiums, such as the Buffalo Bills' stadium.Why Josh advises investors to focus on areas with established regulations and to work with experts who understand the local market.How small improvements, like adding a barrel sauna, can significantly increase revenue. The future of short-term rental investing in New York, taking into consideration new regulations and taxes.And much more...

In this episode of the Cashflow Positive podcast, Kenny challenges a widely held belief that could be limiting opportunities for many investors. While common concerns about market conditions, regulatory landscapes, and financial implications drive decision-making, Kenny suggests you look beyond surface-level assumptions. By breaking down key data points and firsthand experiences, the episode presents a compelling case for reconsidering markets that some might instinctively overlook. While no one-size-fits-all approach exists, Kenny's insights offer a fresh perspective on navigating potential challenges — and even turning them into advantages. For those willing to dig deeper and move past conventional wisdom, this episode presents thought-provoking ideas that could redefine the way they evaluate future investments.If you've enjoyed this episode of the Cashflow Positive podcast, be sure to leave a review and subscribe today!Enjoy!In This Episode You'll Learn:The foremost concern people have about investing in blue states: regulations.Why some red states have strict regulations themselves against short-term rentals, such as Kentucky and Georgia.Kenny's personal preferences and reasons for not investing in California despite his positive outlook on blue states.The advantages of investing in highly regulated markets, such as lower competition and better protection.And much more...

What happens when a great deal turns bad? In this episode of the Cash Flow Positive Podcast, Kenny Bedwell welcomes Brian Lambert, an experienced real estate investor, to break down the realities of short-term rental investing.Brian shares his journey in real estate, from flipping over 100 homes to building a successful short-term rental portfolio. He dives into the risks of over-projecting revenue, the importance of realistic expectations, and how misleading property listings can set investors up for failure. Through a real-life example, Brian explains why due diligence is critical and how knowing the market can prevent costly mistakes.This episode is a must-listen for investors looking to make smarter decisions, avoid financial pitfalls, and navigate today's shifting short-term rental landscape.In This Episode You'll Learn:Why investor expectations vs. reality can make or break a dealHow to spot red flags in revenue projections before purchasing a propertyThe difference between buying real estate vs. buying a business in STR investingWhy knowing your market is the single most important factor in making smart investmentsThe role of patience, persistence, and calculated risk in long-term successAnd much more…Resources:Connect with Kenny on LinkedInFollow Kenny on Instagram

In this episode of the Cashflow Positive podcast, Kenny dives into a high-stakes dilemma that many investors face — one that separates those who thrive from those who barely break even. Drawing from his own experiences and observations in the market, he unpacks a trend that has captivated aspiring investors, promising lucrative returns but carrying hidden risks that often go unspoken. As he reflects on recent real estate activity, he challenges common assumptions and urges a shift in mindset that could mean the difference between long-term success and a costly mistake. You'll learn how even the most well-intentioned strategies can backfire, leaving investors scrambling for a way out. Kenny explores why some deals unravel despite careful planning and what factors should truly guide an investment decision. Whether you're new to real estate or a seasoned investor, this conversation will prompt you to rethink conventional wisdom and equip you with a smarter approach to navigating the market.If you've enjoyed this episode of the Cashflow Positive podcast, be sure to leave a review and subscribe today!Enjoy!In This Episode You'll Learn:The problem of misleading posts by realtors and influencers promoting certain investments. Kenny's approach of always looking for better deals and learning from each transaction. The importance of finding the right deals that will appreciate over time. Why you should be a real estate investor first and a short-term rental operator second.And much more...

What's the smartest way to finance your next short-term rental property? In this episode of the Cash Flow Positive Podcast, Kenny sits down with Matt Stout, a seasoned broker and expert in real estate lending, to tackle the big questions around financing STR investments. With over 30 years of experience and more than 4,000 transactions, Matt shares insider knowledge on DSCR loans, builder financing, and strategies to make your numbers work—no matter the market conditions.From avoiding emotional decision-making to understanding the nuances of construction loans, this episode offers invaluable advice for real estate investors looking to scale their portfolios while minimizing risk and maximizing returns.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 Will Learn:Why DSCR loans are a game-changer for real estate investorsThe challenges and opportunities of financing new construction short-term rentalsHow to balance risk tolerance and emotional decisions when purchasing propertiesWhy running the numbers is critical to making smart investment decisionsThe importance of finding the right lender and understanding your financing optionsAnd much more…Resources:Connect with Kenny on LinkedInFollow Kenny on InstagramConnect with Matt on LinkedInSTRloanguy.com

Are commercial loans the right choice for your short-term rental purchase? In this solo episode of the Cash Flow Positive Podcast, host Kenneth Bedwell breaks down the complexities of commercial lending for real estate investors. Drawing on his own experiences, Kenneth explores when commercial loans make sense, the trade-offs between commercial and conventional financing, and how to make decisions that align with your financial goals.This episode offers a deep dive into the mechanics of DSCR loans, understanding debt-to-income (DTI) ratios, and the critical importance of running your numbers before finalizing any deal. If you're looking to scale your short-term rental portfolio and want to avoid costly mistakes, this episode is packed with actionable insights to guide your financing decisions.In This Episode You Will Learn:The differences between commercial loans and conventional financingHow DSCR loans work and their unique advantages for STR investorsWhy understanding your debt-to-income ratio is crucial for financing decisionsThe importance of planning for long-term goals while choosing loan optionsWhy you should always run your numbers and consult with a trusted lenderAnd much more…Resources:Connect with Kenny on LinkedInFollow Kenny on Instagram

In this solo episode of the Cash Flow Positive Podcast, Kenny dives into part two of The 2-Door Strategy. This strategy, introduced in part 1 by Dr. Rachel explores how achieving key milestones with just two properties can set the foundation for financial freedom, time flexibility, or reaching other personal goals. Kenny shares his own experiences, combining insights from Dr. Rachel and his journey, to highlight how tracking progress and setting attainable goals pave the way for long-term success.From understanding the financial mechanics of short-term rentals to learning how to build momentum through small, consistent wins, this episode is packed with actionable advice for anyone looking to make their mark in real estate investing. Whether you're starting out or scaling up, this episode offers practical tools to help you define and achieve your version of success. 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 tracking progress is essential to staying on top of your short-term rental goalsHow setting short-term, attainable goals builds the momentum needed for long-term successWhy it's more important to focus on the outcomes from your properties rather than the number of doorsHow to balance big, scary goals with achievable milestones to keep your confidence growingWhy chasing money and comparing yourself to others can derail your progressAnd much more…Resources:Connect with Kenny on LinkedInFollow Kenny on Instagram

In this episode of the Cash Flow Positive podcast, Kenny is joined by Dr. Rachel, a former medical professional.You'll discover the transformative journey of a successful professional who had reached the pinnacle of corporate success, only to realize that the conventional path wasn't aligning with her true calling. Hear about the turning point where a significant decision was made to step away from a secure, prestigious position in favor of something entirely different. It's a tale of finding courage to embrace a new identity, one that breaks free from the confines of a traditional career path and embraces entrepreneurship.Kenny and Dr. Rachel also touch on practical advice for those considering a shift toward entrepreneurship, especially for those who feel they might be on the edge of burnout or dissatisfaction in their current roles. This conversation offers a thought-provoking reminder about how serving others with authenticity can lead to unexpected success.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:Dr. Rachel's shift from traditional real estate strategies to short term rentals, focusing on the need for aggressive income rather than passive income. The practical aspects of the 2-door strategy, including its applicability for W2 earners and the importance of systems and operations. The importance of understanding the guest avatar and targeting markets that align with their needs and preferences.The benefits of having a support network and the importance of sharing knowledge and resources with others.And much more...

In this episode of the Cashflow Positive podcast, Kenny explores the shifting dynamics of various markets, offering insights into how they have evolved over time and what that means for those looking to make strategic decisions. You'll discover key factors like supply, competition, and the importance of understanding your audience to ensure long-term success. Learn how to think critically about your own goals and the unique characteristics of the markets you're interested in, with an emphasis on balancing opportunity with realistic expectations.The conversation also dives into the nuanced challenges of navigating highly competitive landscapes and the risks of targeting niche segments without adequate preparation. Kenny shares candid observations about the pressures of adapting to rising standards and maintaining a competitive edge in environments that demand significant investment.This episode offers a refreshing perspective for those at various stages of their journey. Whether you're seasoned or just starting out, the insights shared serve as a valuable guide for making informed choices in a rapidly changing environment.If you've enjoyed this episode of the Cashflow Positive podcast, be sure to leave a review and subscribe today!Enjoy!In This Episode You'll Learn:The regulatory risks in cities like Miami, Florida, and Las Vegas, Nevada. The high prices and low returns in the Emerald Coast, including Destin, Miramar Beach, and Panama City Beach.The regulatory and financial challenges in Oregon and Washington.The evolving market conditions in Asheville, North Carolina, as well as the significant investment needed to compete.And much more...

In this episode of the Cashflow Positive podcast, Kenny flips the script on investment advice for 2025, diving into what not to do. Instead of blindly following the latest market trends or top-ten lists, Kenny explores the pitfalls of oversaturated areas and the challenges of properties that don't align with local demand. He emphasizes that the issue isn't necessarily the market itself but the competition, pricing, and suitability of properties within those areas.You'll learn about the danger of high-maintenance investments. Disocver how overly competitive markets often push investors into unsustainable cycles of reinvestment just to keep up. From expensive amenities to aggressive marketing campaigns, Kenny reveals how these efforts can drain both time and resources without adding meaningful returns.Finally, Kenny highlights the importance of evaluating long-term expenses and avoiding "boom and bust" markets. Drawing on examples like fluctuating tax rates and insurance costs, he suggests that you factor in these variables before committing to an investment.If you've enjoyed this episode of the Cashflow Positive podcast, be sure to leave a review and subscribe today!Enjoy!In This Episode You'll Learn:The confusion caused by various market lists and gurus who claim to know the best markets. The importance of having the right properties in the right markets, not just cool properties in the wrong areas. The value of finding markets where you don't have to constantly reinvest in the property to stay competitive.The challenge of competing against established resorts and hotels in high-demand markets. And much more...

In this episode of the Cashflow Positive podcast, Kenny is joined by Michael Cline, a seasoned real estate agent with a venture capitalist background.During the conversation, Michael brings his extensive experience in the short-term rental market to the table, sharing valuable insights that promise to reshape your understanding of property investment. You'll find strategies, real-life examples, and practical advice that highlight the complexities and opportunities within the competitive market of vacation rentals.Michael breaks down critical components of successful negotiations, discussing scenarios ranging from hot properties with multiple offers to those languishing on the market. He emphasizes the importance of moving quickly, leveraging relationships, and understanding the unique dynamics of short-term rental investments versus traditional home purchases.This episode is a treasure trove of knowledge for anyone interested in real estate investment, particularly in navigating the intricacies of the short-term rental market.If you've enjoyed this episode of the Cashflow Positive podcast, be sure to leave a review and subscribe today!Enjoy!In This Episode You'll Learn:The importance of working with an agent who understands short-term rentals (STRs).Insights into the Poconos real estate market, including why it's a competitive yet rewarding area for STR investments.Strategies for navigating multi-offer situations on highly desirable properties.Approaches to handling appraisal gaps and negotiating lower prices on properties that have been on the market for an extended period.And much more...

In this episode of the Cashflow Positive podcast, Kenny dives into the nuances of crafting deals in a highly competitive environment, blending strategy, negotiation, and creative thinking. You'll discover the importance of recognizing opportunities and leveraging timing to maximize outcomes, providing you with a fresh perspective on how to navigate tough decisions when faced with limited options. You'll be guided through various techniques to handle stalemates, identify leverage points, and foster collaboration among all parties involved. From understanding the dynamics of agreements to uncovering overlooked negotiation tools, Kenny will reveal tactics that can shift the odds in your favor, even when circumstances seem unfavorable.With practical advice and actionable tips, this episode is a masterclass in preparation and adaptability. Whether it's navigating unexpected hurdles or working with others to achieve a shared goal, the discussion is rich with takeaways for anyone eager to refine their negotiation skills.If you've enjoyed this episode of the Cashflow Positive podcast, be sure to leave a review and subscribe today!Enjoy!In This Episode You'll Learn:How to determine if a property is a logical deal before diving into negotiations and why understanding the market timing is crucial to making successful offers. Creative strategies for leveraging agent commissions to close deals when buyer and seller expectations don't align. The importance of inspections in uncovering negotiation opportunities, including securing credits or repairs that can significantly reduce the final cost. Why negotiation is a critical skill in real estate investing and how honing this ability can consistently lead to more favorable deals.And much more...

In this episode of the Cashflow Positive podcast, Kenny continues with the second of a two-part episode concerning where you should be investing.Listen as Kenny lays the groundwork with an analysis of how diverse price points and property features can create lucrative potential in under-the-radar areas. You'll learn to think beyond traditional metrics, emphasizing the importance of privacy, amenities, and unique selling points that set properties apart in competitive landscapes.Throughout the episode, Kenny will highlight the dynamic interplay between accessibility and exclusivity, showcasing how proximity to attractions and thoughtful property enhancements can elevate performance. The discussion balances affordability and market demand, with specific insights on untapped regions.By exploring the intersection of market trends, strategic timing, and creative approaches, this episode will spark curiosity and inspire you to investigate new opportunities.If you've enjoyed this episode of the Cashflow Positive podcast, be sure to leave a review and subscribe today!Enjoy!In This Episode You'll Learn:How understanding market affordability and property features can significantly impact real estate investment decisions. Why seclusion, land, and unique amenities like pools are essential for maximizing property appeal and ROI. How low competition and dynamic pricing strategies in areas like Berkeley Springs, West Virginia, create high-return opportunities for investors. Why Geneva, Ohio, stands out as a top investment market due to its affordability, strong revenue growth, and untapped potential in property design and amenities.And much more...

In this episode of the Cash Flow Positive podcast, Kenny dives deep into the art of making smart investment decisions, particularly for those eyeing the short-term rental market. You'll discover the importance of preparation and strategy, and why simply following the herd into trending markets without considering their unique financial circumstances should be avoided. With insights tailored for both novice and seasoned investors, Kenny sets the stage for understanding the foundational principles of budget planning and investment readiness, ensuring you're not just investing, but doing so wisely. Kenny will introduce two crucial concepts: bankability and affordability. These serve as guiding pillars for determining your financial limits and leveraging your resources effectively. From understanding what lenders evaluate when approving loans to ensuring you have sufficient capital for property improvements, Kenny will walk you through actionable steps to maximize their purchasing power. Whether you're starting small with a one-bedroom rental or scaling to larger, high-revenue properties, Kenny offers a balanced perspective on the time, effort, and financial outcomes involved.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:The two critical factors when starting your short-term rental investment journey.Why setting aside at least 20% of a property's purchase price for furnishings, design, decor, and amenities is essential.The benefits of scaling from smaller properties to larger ones, and why bigger properties can generate higher cash flow while requiring similar time investment. How to align your investment strategy with your financial and career situation, ensuring the time and effort spent on property investments are worthwhile.And much more...

In this episode of the Cash Flow Positive podcast, Kenny is joined by Rachel Gniady, STR consultant with STR Insights.During the conversation, they discuss strategic decisions in a competitive market, particularly in real estate. You'll learn how to leverage knowledge and timing when approaching a potential deal, emphasizing the importance of understanding the broader market context and maintaining a position of strength. Discover the emotional and psychological aspects of negotiation, as Kenny and Rachel touch on the influence of external factors such as agents' motivations and market pressure. The discussion also explores the critical role of making informed decisions from the outset and how proper preparation can lead to long-term success.This episode brings insight into how minor adjustments in approach can unlock larger opportunities and avoid costly missteps, all while maintaining a disciplined focus on the bigger picture.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:The importance of data and analytics in achieving cash flow positivity. Why Rachel prefers short-term rentals over mid-term rentals due to their flexibility and market conditions.The BRRR strategy: buying a property, rehabbing it, renting it out, and refinancing it. The role of relationships in securing better loan terms and the importance of having a track record with lenders.And much more...Resources:STR InsightsRachel's LinkedInConnect with Kenny on LinkedInFollow Kenny on Instagram

What's the best way to find high ROI short-term rental deals when you're short on funds? In this solo episode of Cash Flow Positive, Kenny Bedwell shares actionable strategies to uncover lucrative STR opportunities with little to no money down. Drawing on his own experiences, Kenny discusses creative approaches to deal structuring, financing options, and how to maximize returns while minimizing upfront investment.Kenny emphasizes the importance of focusing on undervalued properties, forcing appreciation, and approaching investments as a real estate investor first and a hospitality provider second. From leveraging seller credits to mastering the BRRRR strategy, this episode is packed with practical tips to help you find deals that cash flow without breaking the bank.Whether you're new to STRs or looking to scale your portfolio on a budget, this episode offers the insights you need to take action and start building wealth. Enjoy!In This Episode You'll Learn:Why undervalued properties with “good bones” are your best bet for ROIHow to leverage the BRRRR strategy to scale your STR portfolioThe importance of combining real estate investment principles with hospitality goalsWhy you need to avoid buying properties based purely on revenue speculationHow to stay scrappy and find financing solutions that work for youAnd much more…Resources:Connect with Kenny on LinkedInFollow Kenny on Instagram

What role does consistency play in being a great neighbor in the short-term rental world? In this episode of Cash Flow Positive, Kenny Bedwell welcomes Alex Shapiro, co-founder of Can Monkey, to discuss how this innovative service simplifies one of the biggest headaches for STR owners: trash management. From keeping properties clean and communities happy to ensuring neighbors are stress-free, Alex dives into the transformative power of systems and automation for property managers.The conversation covers the journey of Can Monkey from a small idea to a multi-state operation, serving thousands of properties. Alex and Kenny discuss how streamlined services like trash handling can save time, improve guest experiences, and build trust within neighborhoods.Whether you're managing one property or an entire portfolio, this episode provides insights into the value of consistency, automation, and being a good neighbor in your STR business.Enjoy!In This Episode You'll Learn:Why consistency is the cornerstone of good STR managementHow automated services like Can Monkey help STR owners maintain harmony with neighborsThe value of systems in streamlining operations and saving timeHow addressing overlooked tasks like trash management can significantly enhance guest experiencesTips for scaling your business while staying connected to community needsAnd much more…Resources:CanMonkey.com Connect with Allex on LinkedInConnect with Kenny on LinkedInFollow Kenny on Instagram

What does it truly mean to be a good neighbor in the short-term rental industry? In this solo episode of Cash Flow Positive, host Kenny Bedwell explores the key principles of being a responsible and engaged STR owner. From fostering positive relationships with neighbors to actively participating in your local and online communities, Kenny shares actionable insights to help you build a sustainable and successful business.Kenny emphasizes the importance of guest vetting to minimize issues, staying informed about local regulations to protect your investments, and contributing to the broader STR community to support other hosts and gain valuable insights. He also discusses how small actions, like maintaining your property's appearance and building trust with nearby residents, can make a big difference in avoiding conflict and ensuring long-term success. Whether you're an established host or just starting, this episode offers practical tips to elevate your STR game while creating harmony in your community. Enjoy!In This Episode You'll Learn:Why being a good neighbor goes beyond running a clean and quiet rentalHow to stay actively involved in your community, even from out of stateThe importance of having an abundant mindset and sharing knowledge with othersSimple ways to build positive relationships with neighbors and gain their trustPractical strategies for guest vetting and maintaining property standardsAnd much more…Resources:Connect with Kenny on LinkedInFollow Kenny on Instagram

How can you scale your short-term rental business while reclaiming your time? In this episode of Cash Flow Positive, host Kenneth Bedwell is joined by Stephanie Figueros, co-founder of Bravo Virtual Assistants, to discuss the game-changing role virtual assistants can play in growing your STR portfolio. Stephanie shares her incredible journey from registered nurse to STR entrepreneur and VA agency founder, highlighting the strategies that helped her build a business that frees up time and boosts productivity.Stephanie dives into the benefits of hiring VAs, from managing guest communications to optimizing listings, and explains how to integrate them effectively into your business. She offers practical advice on identifying the right tasks to delegate, creating efficient training processes, and empowering VAs to help you scale without sacrificing work-life balance. Whether you're managing one property or expanding a growing portfolio, this episode is packed with actionable tips to help you elevate your STR business and achieve greater freedom. Enjoy!In This Episode You'll Learn:How to identify the right tasks to delegate to virtual assistantsWhy scaling your business starts with hiring the right teamThe mindset shift needed to lead effectively and build trustPractical steps to train VAs and set them up for successThe long-term benefits of freeing up your time to focus on growthAnd much more…Resources:Connect with Kenny on LinkedInFollow Kenny on InstagramBravoVirtualAssistants.com