Cash Flow Positive

Most people get into real estate for freedom, but what happens when the money isn’t enough?In this powerful episode of Cashflow Positive, host Kenny Bedwell sits down with Caleb David, a commercial real estate broker, investor, and longtime nonprofit leader whose story goes far beyond deals, commissions, and spreadsheets.Caleb opens up about his early years growing up in a strict environment, his burnout in the nonprofit world, and the leap of faith that brought him into commercial real estate. He also shares candidly about nearly going bankrupt, rebuilding from scratch twice in the same year, and discovering what it really means to live a life of purpose.The deeper theme of this episode: Real estate might bring wealth… But purpose and service bring fulfillment.Caleb’s work with Crazy Love Africa, his time in Ethiopia, his worldview shaped by humanitarian work, and his approach to “creating space and building community” give listeners a new way to think about success, impact, and the life they’re building.This conversation is grounding, challenging, and wildly inspiring.Timestamped Highlights[00:00] Meet Caleb, from conservative upbringing to nonprofit burnout[00:01:50] The leap into commercial real estate and surviving on commission[00:03:00] Becoming Rookie of the Year during a recovering market[00:04:20] Why Caleb doesn’t specialize and how sectors overlap (retail, industrial, STR + commercial combos)[00:05:10] COVID’s impact on the industrial + retail markets[00:06:20] How STR investors can begin learning commercial real estate[00:07:00] The value of curious brokers, not “know-it-alls”[00:09:20] Why empathy belongs in real estate[00:10:30] The theme of “creating space, building community”[00:11:00] Looking beyond money — purpose, faith, and fulfillment[00:12:10] Caleb’s global nonprofit work in Ethiopia and the Middle East[00:14:15] The dangers of “savior mentality” when giving[00:15:40] Introducing When Helping Hurts (book)[00:16:25] Supporting women with HIV in Uganda through Crazy Love Africa[00:17:25] Microgrants: $500 that changes a family’s future[00:18:10] Fair-trade crafts made by women artisans[00:19:00] How giving time can matter more than giving money[00:20:00] Letting go of ego + redefining impact[00:21:30] How to find nonprofits that align with your values[00:23:45] Using 990 forms to evaluate nonprofit transparency[00:25:50] How Caleb balances business, service, and personal well-being[00:27:00] Why rest makes you more productive[00:28:20] Healing from trauma and overcoming near-bankruptcy[00:30:10] Taking “the next right step” in real estate and life[00:33:15] Caleb’s final advice to ambitious professionals[00:34:20] How to connect with Caleb + where to learn moreAbout the GuestCaleb David is a commercial real estate broker, investor, podcaster, and humanitarian based in Colorado. With a background that spans 20+ years in the nonprofit sector, global humanitarian work in Ethiopia and the Middle East, and nearly a decade in commercial brokerage, Caleb brings a rare blend of business expertise and deep-purpose leadership.Today, he serves clients across the Colorado market through Keller Williams Commercial while also serving on the board of Crazy Love Africa, an organization supporting women and children impacted by HIV in Uganda. His mission: create space, build community, and leave a meaningful impact both locally and globally.🔗 LinkedIn | Instagram |

Innovation isn’t just about building something new; it’s about building something better.In this episode of Cash Flow Positive, host Kenny Bedwell sits down with Juliano Silva, a full-time short-term rental investor and designer who’s built a portfolio of standout “signature properties” across multiple U.S. markets. From his early beginnings renting out a spare bedroom in Minnesota to creating high-performing STRs in Florida, Juliano shares how data, creativity, and intention fuel his approach to innovation.They discuss the art of designing properties that can’t be copied, why standing out takes more than adding a pickleball court, and how to create guest experiences that drive both profitability and longevity. Juliano also opens up about building his own construction and design team, the value of experimentation, and how he protects his creative work while staying one step ahead of imitators.If you’ve ever wondered how to make your STR truly unforgettable, this conversation is your blueprint.Timestamped Highlights[00:00] Meet Juliano Silva – From web developer to full-time STR investor[00:01:30] The accidental first Airbnb: renting a bedroom in Minneapolis[00:03:40] Early lessons in regulation and risk[00:05:00] Transitioning from long-term rentals to short-term opportunities[00:07:00] How COVID opened the door to their first real STR in Sarasota[00:09:00] Turning a distressed property into a six-figure rental[00:10:00] Building an in-house design and renovation team from scratch[00:11:30] From experimentation to intentionality – creating “signature properties”[00:14:20] The first pickleball court in Sarasota-Bradenton[00:15:30] Using Google Trends and data to innovate amenities[00:17:30] Why copycats will never win and how to stay ahead through originality[00:19:00] Innovation as a mindset, not just a feature[00:21:00] Designing for brand identity and guest retention[00:23:00] Balancing appreciation and cash flow in every investment[00:24:20] How Juliano protects his designs (and his energy)[00:27:00] Drawing inspiration from international design and hospitality[00:29:30] Innovating the guest experience with continuity and theme[00:32:00] The E.R.O. Formula: Acquisition, Experience, Revenue, Operations[00:37:00] Innovation as problem-solving like early check-in strategies[00:39:30] Competing through service, not just price[00:43:00] Juliano’s top advice: “When they zig, you zag.”[00:45:00] Staying true to your fundamentals and cash flowing positiveAbout the GuestJuliano Silva is a full-time real estate investor, designer, and founder of Behind Every Stay, a newsletter and consulting platform that helps investors create profitable, guest-loved short-term rentals. Based in California with properties across Florida, Minnesota, and North Carolina, Juliano has spent more than a decade in real estate, transitioning from long-term rentals to building data-driven, experience-focused STRs he calls “signature properties.” His approach blends creativity, analytics, and brand identity, helping investors think beyond amenities and build lasting value through intentional design and innovation.🔗 LinkedIn | Website | Facebook | Instagram | X | Behind Every Stay...

If your short-term rental looks the same as it did three years ago, you’re already falling behind.In this episode of Cash Flow Positive, host Kenny Bedwell explains why innovation isn’t optional. It’s the only way to stay competitive in a rapidly evolving STR market. From hotel refresh cycles to new amenity trends, Kenny breaks down how to model what the pros do and apply it to your own properties.He shares real examples of how top operators are staying ahead, from custom pickleball-court designs and splash pads to unique features like three-sided golf simulators and container pools, and why the hosts who think three to five years ahead always win.Learn how to build your own “moat,” create long-term value, and keep your listings at the top of the market.Timestamped Highlights[00:00] Why every STR owner must think like a hotel brand[00:01:00] The hotel renovation cycle and what it teaches hosts about innovation[00:02:00] Sneak peek: Kenny’s live event in New Orleans (Feb 28 – Mar 1) on scaling beyond STRs[00:04:30] The hidden power of staying ahead of your competition[00:07:00] Thinking long-term three- to five-year reposition cycles[00:08:30] Why copying others’ amenities is a race to the bottom[00:09:40] The “Fab Five” amenities and how to make yours stand out[00:12:45] How Kenny’s $40K three-sided golf simulator became a game-changer[00:15:30] New trends: designer pickleball courts, splash pads, and beyond[00:17:30] Building room for future upgrades into every property[00:18:40] How one container pool added $60K in annual revenue[00:20:35] When it’s smarter to innovate than to buy another property[00:21:20] Lessons from hotel design and guest experience[00:22:45] Practical ways to stay “top dog” in your marketResourcesAttend Kenny’s Live Scaling Event (Feb 28–Mar 1, New Orleans) Important LinksWant us to find the deals for you? https://strinsights.com Get Top Markers for STRs (2025) - https://rebrand.ly/28b1df Instagram – @kenny_bedwellYouTube – Cash Flow PositiveLinkedIn – Kenneth BedwellCash Flow Positive is an original podcast hosted by Kenny Bedwell. Brought to you by STR Insights and Podcast Your Brand. Production and editing by Podcast Your Brand.

You don’t have to stop at single-family short-term rentals. You can build the systems and businesses that help others scale, too.In this episode of Cash Flow Positive, host Kenny Bedwell sits down with Tyler Gruskiewicz, a full-time real estate investor and entrepreneur from Louisville, Kentucky. Tyler shares his journey from leaving a W2 job to building a growing portfolio of STRs, boutique hotels, and vertically integrated businesses, including a cleaning company, renovation arm, and property management service, all designed to solve the pain points he faced as a host.They dive into the mindset shifts needed to scale sustainably, the lessons learned from operational chaos, and the power of turning real problems into real opportunities. Tyler also reveals his latest project: transforming one of Kentucky’s oldest bed-and-breakfasts into a mission-driven property supporting veterans and children with speech challenges.If you’ve ever felt “stuck” at the single-family level, this conversation will show you how to think and build bigger.Timestamped Highlights[00:00] Meet Tyler: From Ohio roots to full-time investor in Louisville[01:00] Growing a 7-property STR portfolio + hotels in Florida and Missouri[02:00] What vertical integration really looks like for real estate investors[05:00] Faith Renovations and Signature Stays: turning problems into services[07:00] How Tyler built cleaning, install, and property management teams[08:30] The cleaning nightmare that pushed him to start his own company[13:00] Why checks and balances matter in STR operations[17:00] How one bad turnover led to a total systems overhaul[21:00] Building culture, communication, and shared vision inside your team[25:00] The importance of purpose-driven leadership[29:00] Turning early check-ins into new revenue and guest satisfaction[32:00] The story behind Kentucky’s oldest B&B—and how it became a mission[36:00] Giving back to veterans and kids through real estate[40:00] The takeaway: No one’s coming to save you—build the solution yourselfAbout the GuestTyler Gruskiewicz is a real estate investor known for owning several short-term rental properties in Kentucky with a proven track record in the short-term rental (STR) market. He has gained recognition through interviews and podcasts for his unique approach to growing wealth through STR investments, highlighting both the challenges and strategies for success in this niche real estate segment.​ In addition to his property investments, Gruskiewicz also owns and operates a renovation and cleaning company, leveraging his experience to support and scale his rental business. Recently, he expanded his real estate portfolio by purchasing a 29-door hotel in Branson, Missouri, indicating significant growth and diversification in his hospitality ventures.🔗 LinkedIn | Website Important LinksWant us to find the deals for you? https://strinsights.com Get Top Markers for STRs (2025) - https://rebrand.ly/28b1df Instagram – @kenny_bedwellYouTube – Cash Flow PositiveLinkedIn – Kenneth BedwellCash Flow Positive is an original podcast...

What does “scaling” really mean for you?In this episode of Cash Flow Positive, host Kenny Bedwell breaks down what it truly takes to grow beyond single-family short-term rentals and why the definition of “scaling” should be unique to every investor.Kenny walks through his personal evolution from duplex house hacking to managing multi-unit portfolios, building a co-hosting business, and partnering with investors to acquire large-scale STRs and boutique hotels. Along the way, he shares the mindset, strategies, and lessons that help hosts move from buying one property at a time to building a sustainable, scalable business model that fits their goals, not social media’s definition of success.Timestamped Highlights [00:00] Why “scaling” looks different for every STR owner [00:01:00] Kenny’s early investing story, from house hacking to Airbnb [00:04:45] How Buffalo, NY shaped his mindset on scaling and diversification [00:06:30] Breaking through capital limitations with rental arbitrage [00:09:00] The rise (and fall) of arbitrage and what works better now [00:10:30] Scaling into co-hosting and property management [00:11:45] The power of sharing your wins to attract partnerships [00:13:40] How to start small but think like a business owner [00:15:20] Diversifying across markets for long-term stability [00:18:00] Leveraging other people’s money (OPM) to scale faster [00:20:20] Building partnerships and equity deals with no capital invested [00:22:00] Why hotels aren’t the only way to scale and how big STRs can outperform [00:24:00] Choosing properties that match your goals, not trends [00:25:15] The truth about hotel deals vs. high-performing STRs [00:26:40] Redefining success and scaling on your own terms [00:27:50] A look ahead: scaling through new business opportunitiesResources MentionedLaunch Hosts by Kim Fitzpatrick - Example of scaling through servicesImportant LinksWant us to find the deals for you? https://strinsights.com Get Top Markers for STRs (2025) - https://rebrand.ly/28b1df Instagram – @kenny_bedwellYouTube – Cash Flow PositiveLinkedIn – Kenneth BedwellCash Flow Positive is an original podcast hosted by Kenny Bedwell. Brought to you by STR Insights and Podcast Your Brand. Production and editing by Podcast Your Brand.

What if your next short-term rental deal isn’t failing because of the numbers… but because of your reviews?In this episode of Cash Flow Positive, Kenny Bedwell digs into the “curse” of review-driven real estate—how guest expectations, property condition, and first impressions can quietly make or break your returns. He breaks down the two sides of STR investing (real estate + hospitality), shares real-world examples from his own portfolio, and explains why operations and guest experience are just as critical as deal analysis.You’ll learn what details guests really notice, how to find properties that support great reviews from day one, and the simple fixes that turn complaints into five-star ratings.If you want your short-term rental to outperform the market, hit play and start thinking like a guest, not just an investor.Timestamped Highlights[00:00] Why Kenny “hates” reviews 4and how they shape investor behavior[01:00] The two-headed monster of STR investing: real estate + hospitality[02:30] Why being a great host directly impacts revenue[04:00] How property age and updates influence guest satisfaction[06:00] Lessons from a historic 1860s home that became a five-star stay[09:00] The hidden cost of ignoring capital expenditures[10:40] When old systems (like HVAC) destroy the guest experience[12:00] How unfinished basements and outdated designs kill reviews[15:20] External factors: neighbors, privacy, roads, and power lines[20:00] Designing for privacy, accessibility, and comfort[23:00] How to impress guests from the moment they arrive[25:00] The power of small touches, like Kenny’s ice cream bar idea[27:00] Why first impressions make or break your ratings[30:20] The link between five-star reviews and long-term revenueImportant LinksWant us to find the deals for you? https://strinsights.com Get Top Markers for STRs (2025) - https://rebrand.ly/28b1df Instagram – @kenny_bedwellYouTube – Cash Flow PositiveLinkedIn – Kenneth BedwellCash Flow Positive is an original podcast hosted by Kenny Bedwell. Brought to you by STR Insights and Podcast Your Brand. Production and editing by Podcast Your Brand

How to Get Rich Quick with Real EstateIf you’ve been chasing the next “get rich quick” shortcut in real estate… this episode is your reality check.In this episode of Cash Flow Positive, Kenny Bedwell flips the script on fast money and exposes the truth about building real wealth through real estate. He shares insights from conversations with high-level investors: Those who buy $100M hotels and still play the long game and reveals why the biggest wins come from appreciation, tax strategy, and equity paydown, not just monthly cash flow.You’ll learn the four true pillars of wealth in real estate, how to think like an investor instead of a speculator, and why repositioning your assets the right way can transform your portfolio faster than chasing short-term returns ever will.Stop looking for overnight success. Press play now to learn how the smartest investors actually get rich with patience, data, and a long-term plan.Timestamped Highlights[00:00] Back from the flu and fired up about “get rich quick” myths[01:30] The problem with chasing only cash flow[03:35] Lessons from top-tier investors who buy $100M properties[05:00] The four wealth pillars: cash flow, appreciation, tax savings, and equity paydown[07:00] What “repositioning” really means and why it’s where wealth is built[09:25] When cash flow should be your priority and when it shouldn’t[10:30] Why high-income professionals invest differently (and what that means for you)[12:30] How to calculate true ROI using total return, not just cash flow[15:20] The mindset shift: stop chasing income, start building net worth[18:30] Defining your investment goals before you buy your next STR[21:15] How Kenny evaluates deals now and why forced appreciation beats “good enough”Important LinksWant us to find the deals for you? https://strinsights.com Get Top Markers for STRs (2025) - https://rebrand.ly/28b1df Instagram – @kenny_bedwellYouTube – Cash Flow PositiveLinkedIn – Kenneth BedwellCash Flow Positive is an original podcast hosted by Kenny Bedwell. Brought to you by STR Insights and Podcast Your Brand. Production and editing by Podcast Your Brand

Most investors look at bedroom counts at face value. Kenny Bedwell doesn’t.In this episode of Cash Flow Positive, Kenny reveals a deal-finding strategy he’s seen quietly pay off in competitive short-term rental markets: targeting properties with extra square footage and converting them into higher bedroom counts. From Sedona to the Poconos, Kenny explains why “heads in beds” is the #1 revenue driver, how to legally add bedrooms to force appreciation, and why average-performing STRs will always lose out to top properties.You’ll hear how to spot these overlooked opportunities, the math that makes them work, and why moving quickly under contract is often the difference between landing a deal and watching it slip away.Don’t settle for average returns. Press play now to learn how Kenny turns overlooked listings into high-cash-flow, high-appreciation wins.Important LinksWant us to find the deals for you? https://strinsights.com Get Top Markers for STRs (2025) - https://rebrand.ly/28b1df Instagram – @kenny_bedwellYouTube – Cash Flow PositiveLinkedIn – Kenneth BedwellCash Flow Positive is an original podcast hosted by Kenny Bedwell. Brought to you by STR Insights and Podcast Your Brand. Production and editing by Podcast Your Brand.

Is refinancing your short-term rental a smart move—or a trap that eats away your cash flow?In this episode of Cash Flow Positive, Kenny Bedwell sits down with veteran mortgage broker and STR financing expert Matt Stout. With over 32 years of lending experience and thousands of deals funded, Matt pulls back the curtain on when refinancing actually makes sense. From dropping interest rates and shifting housing trends to creative ways to redeploy “dead equity” into higher cash-flowing properties, this episode delivers the unvarnished truth about refinancing in today’s market.You’ll learn the right (and wrong) reasons to refinance, how to weigh costs versus cash flow, and why keeping versus selling a property can make or break your long-term wealth.Don’t guess your way through one of the biggest financial decisions you’ll face as an investor. Press play now to get Kenny and Matt’s proven framework for knowing when to refinance and how to use it to build real generational wealth.About the GuestMatt Stout is “The STR Loan Guy” and founder of Consumers Financial, a mortgage brokerage licensed in 48 states. With over three decades in lending and a personal background in real estate investing, Matt specializes in STR and DSCR loans that help investors unlock equity and scale their portfolios. He’s known for creative lending strategies, hybrid loan solutions, and his straight-shooting approach to helping investors win deals.🔗 STR Loan Guy Website | YouTube – STR Loan Guy | Facebook | TikTok @thestrloanguyImportant LinksWant us to find the deals for you? https://strinsights.com Get Top Markers for STRs (2025) - https://rebrand.ly/28b1df Instagram – @kenny_bedwellYouTube – Cash Flow PositiveLinkedIn – Kenneth BedwellCash Flow Positive is an original podcast hosted by Kenny Bedwell. Brought to you by STR Insights and Podcast Your Brand. Production and editing by Podcast Your Brand.

If someone handed you $250,000 in cash to invest in a short-term rental, where would you buy and what strategy would you use to make that money work?In this episode of the Cash Flow Positive Podcast, host Kenny Bedwell is joined by Erin Wegrzyn, a real estate consultant with STR Insights, to explore exactly that scenario. Together, they break down how to choose the right markets, set realistic expectations, and avoid the “amenities arms race” that eats into cash flow.Erin shares her journey from long-term rental investor to short-term rental specialist and why her strategy has shifted toward properties that both cash flow and create memories for her family. Kenny and Erin discuss how to research markets, stay ahead of competitors, and build a property that can grow with the market over time, without burning out or over-renovating.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!Key takeaways:How to choose markets without spreading yourself too thinWhy being “one of one” in a market is a huge advantageHow to avoid competing in an endless amenities warWhat to look for in properties that allow for future upgradesWhy following where large investors are putting money can reveal emerging marketsThe best way to build a reliable local team of contractors and cleanersWhy you should visit and experience a market before you invest thereAnd much more...Guest Bio:       Erin Wegrzyn is a real estate consultant with STR Insights, where she helps investors analyze markets and identify profitable short-term rental opportunities. Based in Kentucky, she brings firsthand experience as an investor and a deep understanding of market trends, property selection, and building reliable local teams. Erin is passionate about helping clients choose properties that cash flow, grow in value, and fit their lifestyle goals.Important LinksWant us to find the deals for you? https://strinsights.com Get Top Markers for STRs (2025) - https://rebrand.ly/28b1df Instagram – @kenny_bedwellYouTube – Cash Flow PositiveLinkedIn – Kenneth BedwellDisclaimer: 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.

If $250,000 dropped into your lap today, would you actually know what to do with it?In this episode of Cash Flow Positive, Kenny Bedwell pulls back the curtain on exactly how he’d put that money to work in short-term rentals. He breaks down why your financing strategy can make or break a deal, the five cost buckets most investors forget about, and why setting your ROI goal up front is non-negotiable.You’ll hear Kenny think through real markets, from Florida beaches to Shenandoah cabins, and explain how to spot which ones fit your budget and which ones will bleed you dry.Don’t guess your way into a $250K mistake. Hit play now to hear Kenny’s no-fluff, data-backed roadmap and get clarity on where your money will actually cash flow.Timestamped Highlights[00:00] How a $250K windfall changes your investing strategy overnight[02:14] The financing trap that torpedoes deals before they close[04:18] The five hidden costs every STR investor must budget for[07:36] Kenny’s minimum ROI goals—and why cash flow beats percentages[10:53] The “process of elimination” method for picking your markets[14:25] Why Bradenton, FL, might work—and the brutal barrier to entry[21:00] Shenandoah’s low-barrier charm vs. beach market competition[24:38] How lakefronts in Michigan and urban rentals in Cincinnati stack upResourcesSTR Insights softwareTop Markets Report (via STR Insights website)Dave Ramsey podcast (benchmark reference)Zillow & Redfin (for market comps)Important LinksWant us to find the deals for you? https://strinsights.com Get Top Markers for STRs (2025) - https://rebrand.ly/28b1df Instagram – @kenny_bedwellYouTube – Cash Flow PositiveLinkedIn – Kenneth BedwellCash Flow Positive is an original podcast hosted by Kenny Bedwell. Brought to you by STR Insights and Podcast Your Brand. Production and editing by Podcast Your Brand.

What does Airbnb’s latest fee increase mean for your bottom line, and how should it change the way you evaluate deals?In this episode of the Cash Flow Positive Podcast, Kenny Bedwell sits down with Rachel Gniady, full-time real estate investor and STR Insights consultant, to talk about how the new 15.5% host fee is reshaping underwriting, deal selection, and long-term strategy.Rachel shares how she is being even more conservative with revenue estimates, why she is rejecting deals that don’t have a wide enough margin, and why being “one of one” in a market is more important than ever. Together, Kenny and Rachel dive into moats, market trends, appraisals, and the importance of thinking like an investor first, even as competition heats up and the “middle” of the STR market gets squeezed.Want to keep spotting high-margin STR deals even as fees climb? Listen now and sharpen your strategy. 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!Key takeaways:Why Airbnb’s fee change demands more conservative underwritingHow to evaluate properties with a “good, better, best” revenue approachWhy being unique in your market protects your profitsThe dangers of chasing trends and how to know when to walk awayWhy comps, cost basis, and appraisals matter more than everHow to protect yourself in today’s “Wild West” real estate marketWhy stability can beat higher short-term returns in the long runThe importance of making offers quickly and confidentlyAnd much more...Guest Bio:       Rachel Gniady is a full-time real estate investor and consultant for STR Insights, where she has helped over 50 clients close deals and build profitable short-term rental portfolios. Based in New Orleans, she has nearly 20 years of experience buying, improving, and selling properties. Resources:Part 2: Finding High ROI STR Deals with No Money with Rachel GniadyConnect with Rachel on LinkedInImportant LinksWant us to find the deals for you? https://strinsights.com Get Top Markers for STRs (2025) - https://rebrand.ly/28b1df Instagram – @kenny_bedwellYouTube – Cash Flow PositiveLinkedIn – Kenneth BedwellDisclaimer: 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...

Airbnb has just announced a major change to its fee structure, and for hosts, the impact could be huge.In this episode of the Cash Flow Positive podcast, Kenny Bedwell breaks down the shift from a split-fee model to a single-host fee of 15.5%. He explains what this really means for your payouts, why simply raising your rate isn’t the answer, and how the wrong pricing strategy could tank your rankings and bookings.Kenny walks through the math behind the change, why some hosts will be hit harder than others, and what you can do to protect your bottom line. From understanding price elasticity to planning ahead with discounts and direct bookings, this episode is packed with insights and strategies you won’t want to miss.Don’t let Airbnb’s new fee structure cut into your earnings. Tune in to learn the smart strategies that keep your payouts strong.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!Key takeaways:Why raising your prices could hurt your rankingsHow pricing without a strategy leaves you vulnerable to underpriced competitorsWhy cookie-cutter properties are more exposed than unique listingsThe exact percentage increase needed to maintain your current payoutsWhy timing your price adjustments can affect your Airbnb search rankingsHow to think about cause and effect when responding to platform changesAnd much more...Important LinksWant us to find the deals for you? https://strinsights.com Get Top Markers for STRs (2025) - https://rebrand.ly/28b1df Instagram – @kenny_bedwellYouTube – Cash Flow PositiveLinkedIn – Kenneth BedwellDisclaimer: 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.

What separates investors who land the best deals from those who watch them slip away?In this episode of the Cash Flow Positive podcast, Kenny Bedwell continues his deep dive into the reasons most people miss out on profitable real estate deals. Building on Part 1’s discussion of vision and creating a moat, Kenny highlights three more critical factors that separate average investors from top performers: acting fast, knowing your guest avatar, and truly understanding what makes a property special in its market.Through real-world examples, Kenny shows why hesitation, personal bias, and limited knowledge often cost investors life-changing opportunities. This episode is a practical roadmap to spotting hidden value and moving with confidence when great deals appear.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!Key takeaways:Why hesitation and “analysis paralysis” cause investors to miss out on dealsThe importance of acting fast while protecting yourself with contingenciesHow top investors use due diligence periods to secure multiple opportunitiesWhy buying for personal preference instead of guest demand leads to missed dealsHow understanding your “guest avatar” reveals what drives revenue in each marketWhy many investors fail simply because they don’t know what to look forHow to elevate a property’s value by adding design, decor, and amenitiesThe difference between a natural moat and a completed moat — and how to build oneAnd much more...Important LinksWant us to find the deals for you? https://strinsights.com Get Top Markers for STRs (2025) - https://rebrand.ly/28b1df Instagram – @kenny_bedwellYouTube – Cash Flow PositiveLinkedIn – Kenneth BedwellDisclaimer: 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.

Why do so many investors pass up incredible opportunities that are sitting right in front of them?In this episode of the Cash Flow Positive Podcast, Kenny Bedwell breaks down the number one reason most people miss out on great real estate deals: a lack of vision. Using real-world examples, including a six-bedroom Montana property overlooked by more than ten investors, Kenny illustrates how the best opportunities often require foresight, creativity, and the willingness to see potential where others only see problems.From the concept of building a “moat” that sets your property apart, to understanding why people default to safe, turnkey investments, Kenny shows how successful investors think differently. Discover how one investor turned a rejected Montana property into a top-performing STR.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!Key takeaways:Why most investors fail to recognize the potential in overlooked propertiesThe importance of having vision when evaluating dealsHow to identify and build a “moat” that separates your property from the competitionWhy great deals often come in the form of outdated or overlooked homesHow one investor turned a rejected Montana property into a cash-flowing success storyWhy copying turnkey models is short-term thinking, and how long-term strategies create real wealthAnd much more...Important LinksWant us to find the deals for you? https://strinsights.com Get Top Markers for STRs (2025) - https://rebrand.ly/28b1df Instagram – @kenny_bedwellYouTube – Cash Flow PositiveLinkedIn – Kenneth BedwellDisclaimer: 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.

What does it really take to turn a rundown property into a high-return investment? In this episode of the Cash Flow Positive podcast, host Kenny Bedwell is joined by Kyle Powers, a top-producing agent and experienced real estate investor, to continue the discussion on the infinite return model.Kyle shares his hands-on approach to finding undervalued properties, forcing appreciation, and navigating the emotional roller coaster of major renovation projects. From choosing the right markets to building reliable teams, Kyle explains how smart planning and execution can eliminate risk and create life-changing financial wins.Want to know how pros turn rundown homes into cash-flow machines? Hear the infinite return model explained step by step in this episode. Don’t just buy another property—discover the strategy that pays you back in full and keeps paying you forever.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!Key takeaways:Why having “boots on the ground” is invaluable for successful real estate projectsHow to budget realistically and prepare for surprises in renovation projectsThe emotional side of investing and why big returns require taking calculated risksWhy eliminating risk comes down to working with the right people and running the right numbers.How to find the best markets for forcing equity and long-term gains.Kyle’s coaching insights on what makes the infinite return model sustainable.And much more...Guest Bio:       Kyle Powers is a Top Producing Agent from Manhattan, Kansas, ranking in the top 5% of Realtors with over 400 homes sold in just 8 years. Beyond sales, he invests in long-term and short-term rentals, house flips, and co-founded The Elevated Realtors, where he trains agents to scale their businesses.Resources:Connect with Kyle on LinkedInConnect 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

What if you could own a property that pays you back entirely and then continues to cash flow year after year, with no money left in the deal? In this episode of the Cash Flow Positive podcast, Kenny Bedwell breaks down the infinite return model and shows how real estate investors can use it to create cash flow with minimal long-term capital tied up.Kenny explains how this strategy works in both short-term rentals and larger projects, including his own experience renovating a hotel in New Orleans. From understanding appraisals and refinancing to leveraging other people’s money, this episode offers practical insights into achieving truly infinite returns in real estate.Don’t just buy another property. Learn the strategy that can give you returns with no money left in the deal. 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!Key takeaways:What the infinite return model is and why it matters in real estate investingHow to force appreciation through renovations or strategic value-add projectsThe role of appraisals, refinancing, and financing options in pulling money back out of a dealWhy short-term rentals are uniquely positioned for infinite returnsHow building or renovating with short-term rentals in mind creates long-term advantagesKenny’s real-world hotel investment example and how it demonstrates this model in actionAnd 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.

If you want to dominate your market and attract guests who keep coming back, your property needs to stand out in ways others can’t (or won’t) replicate. In this episode of the Cash Flow Positive podcast, Kenny Bedwell shares advanced strategies for turning an ordinary property into a top-performing short-term rental that crushes the competition.Kenny explains why unique property characteristics, “Wow” spaces, and smart upgrades can make your listing nearly impossible for competitors to match. He also discusses how to identify undervalued opportunities, keep expenses down, and plan for long-term profitability, all while staying laser-focused on 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!Key takeaways:Why the most successful properties have attributes that competitors can’t easily replicateHow to identify and enhance unique characteristics in your propertyThe role of “Wow” spaces in boosting bookings and enhancing guest satisfactionWhy keeping expenses low is just as powerful as finding undervalued dealsHow Kenny applies his own “Crusher Competition” strategy to make his Airbnbs unbeatableAnd much more...Resources:Connect with Kenny on LinkedInFollow Kenny on InstagramThe Strategy That Makes My Airbnbs Impossible to Compete WithDisclaimer: 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.

What separates a property that barely breaks even from one that dominates its market? It’s not just timing, it’s strategy.In this episode of the Cash Flow Positive podcast, Kenny Bedwell shares hard-earned insights from his latest experiences in the field and on stage at the STR Wealth Conference. Drawing from real client case studies, personal portfolio wins, and lessons learned from analyzing hundreds of STRs, Kenny emphasizes one core principle: if you want to stand out, you need to do what 95% of people won’t, or can’t do.Whether it’s investing in an unconventional niche, buying undervalued properties with built-in equity, or avoiding oversaturated markets that everyone’s rushing into, this episode offers a blueprint for smarter decision-making. Kenny doesn’t just talk numbers, he dives deep into mindset, strategy, and the critical difference between copying a great idea and creating one.You will walk away with a sharper understanding of what makes an STR truly resilient and why now, more than ever, real estate investing requires bold moves and creative thinking. If you’ve been sitting on the sidelines or unsure where to focus your next property search, this episode will give you the urgency and clarity to act.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!Key takeaways:Why you shouldn’t wait until fall to start searching for STR propertiesThe 95% rule and how to apply it to your next investmentWhat it really means to have a moat and how to create oneHow to spot undervalued properties with instant equityWhy copying a good deal isn’t the same as creating oneWhat investors are getting wrong in oversaturated marketsThe biggest mistake Kenny sees when hosts chase cash flow aloneHow to structure your next deal to survive any dip in revenueAnd 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.

Are you thinking about selling your short-term rental but unsure how to prepare it for a profitable sale? In this episode of the Cash Flow Positive podcast, host Kenny Bedwell sits down with real estate expert and investor Madeline Blum to unpack the strategic steps needed to maximize your return when exiting a short-term rental investment.Madeline shares her insights from both the agent and investor perspective, offering practical advice on preparing a property for listing, managing guest experience during the transition, and understanding the realities of today’s saturated market. From the importance of budgeting and inspections to the value of patience and honesty, this conversation is a candid and informative guide for anyone considering selling an STR.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!Key takeaways:Why budgeting upfront for guest experience can make or break your STR’s performanceHow to coach your clients for STR success before listingWhy a bad cleaner can hurt your reviews—and your ability to sellThe importance of routine inspections and functional appliancesWhy pre-listing inspections are crucial in today’s competitive marketWhen it might be wiser to take a loss and move onHow to make executive decisions based on your unique situationThe value of leaning on local resources and being adaptableWhy honesty—from yourself and your agent—is key to successWhy patience is a necessary mindset in a slow marketAnd much more...Guest Bio:       Madeline Blum is a real estate agent and short-term rental investor with properties in multiple markets, including the Smoky Mountains, North Carolina, the Bourbon Trail, and Panama City Beach. With experience on both sides of the deal, she brings a strategic, investor-savvy approach to buying, selling, and managing STRs—always focused on creating long-term value and delivering exceptional service.Resources:Connect with Kenny on LinkedInFollow Kenny on InstagramFollow Madeline on InstagramFollow Madeline 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.