Cash Flow Positive

If people just wanted a place to sleep, they’d book a hotel. But in today’s competitive short-term rental market, it’s experiences that drive revenue, and no one knows that better than Merit Harris.In this episode of the Cash Flow Positive podcast, Kenny Bedwell welcomes Merit, founder of Merit Badge Property Management, to dive into the business of creating standout STRs through interactive amenities, ROI-driven design, and a deep understanding of what guests actually want. From his no-nonsense approach to systems and team leadership to the design decisions that impact bookings, Merit shares a wealth of practical insights for property owners and managers alike.Whether you’re co-hosting a few properties or scaling a management business, this conversation will inspire you to think bigger and design smarter.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 design and amenities must go beyond aesthetics to actually drive revenueHow to evaluate your property as an experience, not just a place to stayWhat makes a listing “sticky” and how that affects your nightly rateWhy most designers miss the mark on interactive ROIHow Merit approaches team management with outcomes—not micromanagementThe importance of systems in building a scalable STR businessHow to identify design strengths and expand creatively without losing cohesionAnd much more...Guest Bio:       Merit Harris is the founder of Merit Badge Property Management, where he helps short-term rental owners increase revenue and create unforgettable guest experiences through strategic design and streamlined operations. Known for his bold mindset and system-driven approach, Merit is passionate about empowering clients and team members alike to live their “best life” while building a thriving STR business.Resources:Connect with Kenny on LinkedInFollow Kenny on InstagramMerit Badge Property Management Follow Merit on FacebookFollow Merit on InstagramFollow Merit on TikTokDisclaimer: 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.

Is your short-term rental just blending into the crowd? In this episode of the Cash Flow Positive podcast, Kenny Bedwell breaks down one of the most powerful (and affordable) ways to make your property stand out—micro designs.Kenny explores why the typical templated design approach fails to drive bookings and how a strategic focus on a few unique spaces can elevate your listing and boost your bottom line. You’ll learn how to approach short-term rental design from a marketing-first perspective—without breaking the bank.Whether you’re furnishing a new property or looking to revamp an existing one, this episode offers smart, practical advice to help you create an unforgettable guest experience.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 traditional, templated setups don’t maximize your STR’s revenue potentialWhat micro designs are and how they can transform a propertyHow to choose which spaces to focus on—and why less is moreThree types of amenities that directly affect your revenueHow photo strategy influences booking decisionsWhy micro designs work for any budget, not just luxury listingsThe real reason most STRs fail to stand out—and how to fix itAnd 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.

Is the mid-term rental strategy a hidden gem in today’s market, or are short-term rentals still king?In this insightful continuation of the MTR vs. STR conversation, host Kenny Bedwell brings back real estate investor and healthcare professional Vivian Yip to break down the realities of both strategies in today’s economic climate. Drawing from her extensive experience operating properties across multiple states, Vivian walks listeners through the nuances of running mid-term rentals (MTRs), how they compare to short-term rentals (STRs), and how to adapt your investment strategy for long-term success.They also dive into key data points, guest expectations, regulations, and real-world profitability scenarios, making this a must-listen for anyone considering a shift in their rental portfolio or entering the game with a clear strategy in mind.Listeners like you are scaling faster—and smarter—by following this show. Subscribe now and level up your STR playbook. 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 type of investor is best suited for MTRs vs. STRsWhy MTRs can be more stable but not necessarily passiveKey differences in guest expectations, operations, and pricingHow to adapt your rental strategy when regulations changeWhy the STR narrative has shifted and what it means for your cash flowVivian’s insight into property selection, especially in healthcare-heavy marketsHow to evaluate the real profit margins when choosing your rental typeWhen and how to pivot from STR to MTR depending on demand and seasonalityAnd much more...Guest Bio:       Vivian Yip, formerly a program manager at Apple, transitioned full-time into real estate in 2018 alongside her husband, James. While raising two children and flipping homes, they discovered the power of furnishing affordable properties for extended stays—an approach that thrived during the pandemic and simplified management. Today, Vivian leads Corporate Rentals USA by Hestia, where she merges hospitality with real estate and helps investors elevate their rental income through strategic branding and smart operational systems.Resources:Connect with Kenny on LinkedInFollow Kenny on InstagramCruHomes.com VivianYip.com Follow Vivian 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.

Are mid-term rentals really the safer bet—or are short-term rentals still the reigning champion when it comes to maximizing cash flow?In this episode, Kenny Bedwell dives into the often-debated comparison between MTRs and STRs. He breaks down the financial, operational, and strategic nuances of each model, offering a balanced look at the pros and cons. From tax savings and revenue potential to guest expectations and personal preferences, Kenny lays out a clear framework for making the right investment choice based on your goals.Whether you’re just getting started or looking to scale to commercial-grade properties, this episode will help you think beyond the hype and make data-informed decisions.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 makes STRs more dynamic—but also more volatileThe role of "experience" in STR marketing vs. MTR expectationsHow future financing may be based more on revenue potential than creditWhat buying the right “moat” means for long-term STR successThe tax advantages of STRs over MTRsWhy STRs are a stepping stone to owning commercial or hotel propertiesAnd 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.

Most new hosts waste thousands before guests ever check in—Kim Fitzpatrick is here to change that.In this episode of the Cash Flow Positive podcast, Kenney Bedwell is joined by STR expert and Launched Host founder Kim Fitzpatrick, who reveals the #1 thing she wishes she’d done before opening the doors to guests. Hint: It’s not about having Instagram-worthy decor or the perfect throw pillows. It’s about protection, durability, and saving your sanity.Kim shares a refreshingly honest behind-the-scenes look at what actually happens after launch day, including the unexpected ways guests use (and sometimes misuse) your space. She dives into what she learned through her own costly mistakes—like hours spent stain-fighting ottomans and chasing down replacement remotes—and how a few proactive decisions could have saved her thousands of dollars and endless frustration.If you’re about to launch your own STR—or thinking about upgrading an existing one—this conversation is packed with actionable insights that will help you furnish smarter, protect your investment, and build a guest-ready home that holds up to real-world wear and tear.Want expert help launching your STR? Visit LaunchedHost.com to get started with Kim’s team. 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 investing in fewer, better-quality furnishings saves money in the long runWhat “preventative maintenance” actually looks like in a real STRThe importance of protecting fabrics and surfaces from day oneHow to prioritize your STR budget when it starts to stretchThe simple cleaning items every STR needs on-siteWhat Kim regrets not doing from the start, and how it cost her hours of frustrationAnd much more...Guest Bio:       Kim Fitzpatrick is the owner and founder of Launched Host, a company that helps short-term rental owners stage and prepare their properties for guests fast. After a 20-year career as a physical education teacher, Kim transitioned into real estate and became a successful investor and Superhost across multiple states. Her hands-on experience revealed a major need in the short-term rental (STR) market: efficient, professional property setup.Resources:Connect with Kenny on LinkedInFollow Kenny on InstagramPART 2 Kim Fitzpatrick - The STR tortoise vs the hareConnect with Kim on LinkedInLaunchedhost.com Disclaimer: 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.

Ever feel like launching your short-term rental is like pouring money into a black hole? Before you spend a dime on furniture or tools, you need to hear this. In this episode, Kenny Bedwell breaks down five high-impact strategies to help STR operators save thousands of dollars before even opening their doors to guests.From leveraging partnerships with cleaning companies to understanding tax benefits, Kenny shares tactical, money-saving insights that many first-time hosts overlook. If you're launching—or even planning to launch—an STR, this episode is your financial wake-up call.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 getting on your cleaning company’s preferred list can give you major discountsHow to avoid unnecessary tool and equipment costsThe benefits of hiring a general contractor vs. DIYWhat you need to know about state and local STR licensesHow to leverage tax strategies to reduce your upfront expensesThe critical importance of knowing your zoning laws before launchingWhy doing less yourself might actually save you money in the long runPractical real-world examples of STR operators who saved bigAnd 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.

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