Explorez tous les épisodes du podcast Cash Flow Positive
| Titre | Date | Durée | |
|---|---|---|---|
| Part 2: Tips for working with out of state contractors | 04 déc. 2025 | 00:42:29 | |
Hiring contractors is hard enough… hiring them out of state can feel terrifying. In this value-packed episode of Cashflow Positive, Kenny sits down with Jen Josey, real estate investor, coach, mastermind leader, and construction expert, to break down exactly how to find, vet, manage, and protect yourself when working with contractors in markets where you don’t live. Jen shares the six critical documents every investor should use, the insider process for finding investor-friendly contractors (hint: it’s not Google), how to structure payment schedules that protect your budget, and the legal tools that saved her from a lawsuit. If you plan to renovate a property outside your local market, this conversation may literally save you thousands. Timestamped Highlights[00:00] Meet guest Jen Josey and her path from teacher → corporate → real estate [00:01:20] How Jen replaced her corporate income in 8 months [00:01:55] What Jen is working on today: coaching, STRs, investing, and running multiple companies [00:03:00] Current STR portfolio: beach condo, Boone cabin, and plans for a micro-resort [00:05:00] What Jen looks for: smaller STRs, pet-friendly, waterfront, couples-focused [00:06:25] How she evaluates markets in NC, VA, and SC [00:08:10] Kenny’s lead-in to contractor horror stories and out-of-state projects [00:09:00] Jen’s #1 starting point: investor Facebook groups (and how to post correctly) [00:09:45] Step 2: local REIAs (why they matter and what quality they attract) [00:10:40] Window replacement sticker shock: a real example ($7K for three windows) [00:12:00] Never pay large deposits upfront—and what to do instead [00:12:45] The exact six critical documents every investor should use [00:13:35] The “lien waiver” that saved Jen from being sued [00:14:10] The contract: deadlines, penalties, warranties, and holding contractors accountable [00:15:40] Insurance + indemnification: adding yourself to a contractor’s policy [00:16:20] Building your scope of work from the inspection report [00:16:55] Paying your inspector to verify contractor work [00:17:40] The proper way to structure a payment schedule (why the final payment is the largest) [00:18:55] W-9 requirements for anyone paid over $600 [00:19:20] Contractors who refuse to sign contracts—why you should walk away [00:20:05] Kenny’s theater room story and how a missing change order cost him [00:21:55] How to prevent “death by $500 change orders” [00:23:15] How hard money lenders help enforce accountability [00:24:00] What makes someone an investor-friendly contractor [00:27:00] Jen’s secret weapon: “pimping out” contractors to keep prices low [00:29:00] Code of Conduct on job sites (English + Spanish) [00:33:00] The two most important people on your STR team: cleaners + handyman [00:34:25] Paying your handyman well to secure long-term loyalty [00:35:00] Jen’s final tip for cash flowing positive: deliver unforgettable guest experiences [00:37:00] Why theme ≠ experience (Kenny’s Taylor Swift pillow story) [00:39:20] Where to follow Jen and how to get her contractor documents About the GuestJen Josey is a real estate investor, coach, podcaster, and founder of the Real Estate Investor Growth Network (REIGN). After leaving her corporate job, Jen built a diverse portfolio across long-term rentals, short-term rentals, flips, and new construction. She runs multiple companies under the Joli brand, including construction, brokerage, and investment arms, and coaches investors nationwide on buying and renovating out of state. She is also the host of the Real Estate Investor Growth Network Podcast and leads a mastermind for active investors. 🔗 | |||
| Part 1: Tips for working with out of state contractors | 02 déc. 2025 | 00:25:18 | |
Ever felt blindsided by skyrocketing costs and endless delays when renovating a property out of state? You are not alone, and you do not have to fall victim to contractor nightmares again. In this no-fluff solo episode, Kenny Bedwell (the relentless numbers-driven voice behind Cash Flow Positive) drops a real talk blueprint for working with out-of-state contractors on STR investments, so you keep your profits high and your headaches low. Pulling from raw experience and data-backed practical steps, he reveals the biggest blunders investors make, how to negotiate with confidence, and exactly what you must ask (and never say!) before handing over your dollars. Don’t get burned by rookie mistakes or overpriced quotes. Listen now for the counterintuitive tactics, time-saving hacks, and inside knowledge you will not get anywhere else. Delay and you risk expensive lessons—press play for power, profit, and peace of mind. Timestamped Highlights[00:00] – Why most investors get “out-of-state” pricing—and how to avoid the trap [00:02:28] – The one detail about yourself you must hide when calling contractors [00:05:08] – Project management nightmares: overlapping crews, costly delays, and what nobody tells you [00:08:00] – Inside Kenny Bedwell’s painful 6-month permit saga (and the holding costs almost everyone forgets) [00:10:40] – Social media as a referral jungle: How to decode real reviews from angry rants [00:16:08] – The invisible 10–15% overage rule and why your budget always lies [00:18:00] – The supply scam: How to keep contractors from secretly padding their profits [00:22:05] – The exact moment you should call contractors (Miss it, and it’ll cost you thousands!) Mentioned Resources
Important Links
Cash Flow Positive is an original podcast hosted by Kenny Bedwell. Brought to you by STR Insights. Production and editing by Podcast Your Brand. | |||
| How Far Can $200K Really Go? | 25 nov. 2025 | 00:26:10 | |
$200,000 used to feel like a powerhouse investing budget… but in today’s short-term rental landscape, it doesn’t go nearly as far as it used to. In this solo episode, Kenny Bedwell breaks down the hard truth: $200K is the new $100K. Competitive STR markets have leveled up, amenities have escalated, and investor expectations have shifted. Kenny walks through why $200K no longer guarantees entry into the big-boy markets (Smokies, Bradenton, Asheville, Bourbon Trail), what buyers consistently misunderstand about down payments vs. true budget, and how to think like a strategic investor rather than a pre-approval chaser. He also unpacks the 20% Rule, the reality of amenity wars, why your biggest moat is future thinking, and the path newer investors should take when they have less than $200K to deploy. If you want to make your money actually work and stop getting crushed by competition, this episode is your roadmap. Timestamped Highlights[00:00] Why $200K doesn’t stretch like it used to [00:01:20] The psychological trap of buying based on pre-approval [00:02:10] The 20% Rule: what your true budget actually is [00:03:20] Why a $500K home can require $200K to do it right [00:04:40] Competitive markets and the real cost of keeping up [00:06:00] When big brokerage agents start pushing a market… it’s already too late [00:07:20] Why chasing what worked last year won’t work now [00:08:10] Downsizing: why a killer 2–3 bedroom beats an underfunded 6-bedroom [00:09:20] The amenity war: pickleball courts, splash pads, heated pools, full design [00:10:50] Real estate finance lesson: why abnormal returns disappear [00:11:40] Today ≠ 2021: why $200K no longer buys performance [00:12:25] How to pick markets with lower barriers of entry [00:13:10] What “drivable markets” really are and why they outperform [00:14:35] How to read metropolitan travel patterns for hidden gems [00:15:40] Why most investors are psychologically wired to overleverage [00:16:20] The only way to compete with bigger players [00:17:50] Planning for future competition, not past comps [00:18:30] Kenny’s Walkins Glen example: $350K → $144K gross [00:19:30] Why futuristic thinking builds moats [00:20:10] The Autopilot app story (Nancy Pelosi portfolio tracking) [00:22:15] Understanding how investor flood-ins flatten returns [00:23:20] How to pick properties that will hold up against new competition [00:24:30] If you want a moat, you must create it [00:25:10] Kenny’s offer to break down “moat categories” in a future episode [00:25:50] How to message Kenny directly with questions Mentioned Resources
Important Links
Cash Flow Positive is an original podcast hosted by Kenny Bedwell. Brought to you by STR Insights. Production and editing by Podcast Your Brand. | |||
| Investing beyond the returns | 19 nov. 2025 | 00:35:37 | |
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 more About 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. | |||
| Part 2: You MUST Innovate in the STR space | 13 nov. 2025 | 00:47:31 | |
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 positive About 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... | |||
| Part 1 – You MUST Innovate in the STR Space | 11 nov. 2025 | 00:22:58 | |
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 market Resources
Important Links
Cash 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. | |||
| Part 2: Scaling beyond single family homes | 06 nov. 2025 | 00:33:18 | |
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 yourself About 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. Important Links
Cash Flow Positive is an original podcast... | |||
| Part 1: Scaling beyond single family homes | 06 nov. 2025 | 00:29:34 | |
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 opportunities Resources Mentioned
Important Links
Cash 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. | |||
| Part 1: The curse of review driven real estate | 28 oct. 2025 | 00:31:35 | |
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 revenue Important Links
Cash 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 estate | 23 oct. 2025 | 00:23:01 | |
How to Get Rich Quick with Real Estate If 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 Links
Cash 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 | |||
| Part 1 & 2: The deal finding strategy no one is talking about | 07 oct. 2025 | 00:25:30 | |
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 Links
Cash 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. | |||
| Should you refinance your property? | 02 oct. 2025 | 00:35:33 | |
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 Guest Matt 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 @thestrloanguy Important Links
Cash 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. | |||
| Part 2: If you had $250k to invest, where should you go? | 25 sept. 2025 | 00:40:40 | |
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:
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.
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. | |||
| Part 1: If you had $250k to invest, where should you go? | 23 sept. 2025 | 00:29:27 | |
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 up Resources
Important Links
Cash 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. | |||
| Part 2: Airbnb just increased fees for hosts! | 16 sept. 2025 | 00:36:45 | |
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:
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 Gniady Connect with Rachel on LinkedIn
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... | |||
| Part 1: Airbnb just increased fees for hosts! | 09 sept. 2025 | 00:24:12 | |
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:
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. | |||
| Part 2: Why most people miss great deals | 02 sept. 2025 | 00:31:16 | |
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:
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. | |||
| Part 1: Why most people miss great deals | 26 août 2025 | 00:23:47 | |
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:
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. | |||
| Part 2: The infinite return model | 21 août 2025 | 00:43:17 | |
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:
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 Kenny on LinkedIn 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 | |||
| Part 1: The infinite return model | 19 août 2025 | 00:17:59 | |
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:
Resources: Connect with Kenny on LinkedIn 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. | |||
| Part 2: Finding deals before the end of the year | 12 août 2025 | 00:29:00 | |
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:
Resources: Connect with Kenny on LinkedIn The Strategy That Makes My Airbnbs Impossible to Compete With 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. | |||
| Part 1: Finding deals before the end of the year | 05 août 2025 | 00:19:54 | |
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:
Resources: Connect with Kenny on LinkedIn 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. | |||
| Part 2: Prepare, Position and Profit from Selling a STR | 31 juil. 2025 | 00:38:20 | |
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:
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 LinkedIn 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. | |||
| Part 1: Prepare, Position and Profit from Selling a STR | 29 juil. 2025 | 00:15:27 | |
Are you thinking about selling your short-term rental property, but unsure how to get top dollar for it? In this episode of the Cash Flow Positive podcast, Kenny Bedwell shares a step-by-step guide to help you prepare, list, and profit from selling your STR. You’ll learn what documents to gather, how to estimate your property’s value, what buyers are really looking for, and how to present your property in the most attractive light. Kenny also explains common mistakes to avoid, like underestimating how much your property is worth or ignoring the emotional aspects of the sale. Thinking of selling your short-term rental? Don’t list it before you listen to this episode. Kenny breaks down how to prep your STR like a pro—from documents and value estimates to buyer psychology and profit strategy. Whether you’re weeks or years away from a sale, this episode will help you exit smart. 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:
Resources: Connect with Kenny on LinkedIn 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. | |||
| Part 2: Be a Top Producer without the "Super Amenities" | 24 juil. 2025 | 00:42:46 | |
Can you create a top-performing short-term rental without spending a fortune on luxury amenities? In this episode of the Cash Flow Positive podcast, Kenny Bedwell sits down with Beata Lorinc to explore how smart design, thoughtful upgrades, and deep attention to detail can make your STR stand out—without breaking the bank. Beata shares her insights on how to approach STR design with both strategy and creativity. She explains how functionality, guest experience, and budget-conscious decisions can come together to elevate your listing above the competition. The conversation covers everything from curating standout features and maximizing ROI to managing vendors and understanding what guests really want. Whether you're just starting out or looking to refresh your existing rental, Beata’s practical tips and candid advice will help you rethink what it takes to build a high-performing property. Learn the subtle tweaks and smart differentiators that actually move the needle, and start creating unforgettable guest experiences that don’t break the bank. 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:
Guest Bio: Beata Lorinc is a North Carolina licensed Realtor, the owner of a boutique luxury full-service property management firm, and a trusted consultant for busy professionals. With a sharp eye for potential, she specializes in transforming ordinary homes into high-performing short-term rentals. Drawing from over a decade of experience at Procter & Gamble in supply chain and customer service—combined with years of hands-on success in property design, vendor management, and guest relations—Beata delivers strategic solutions that help hosts thrive in a competitive market. Resources: Connect with Kenny on LinkedIn 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. | |||
| Part 1: Be a Top Producer without the "Super Amenities" | 23 juil. 2025 | 00:19:25 | |
Can you dominate your short-term rental market without investing in expensive amenities? In this solo episode of the Cash Flow Positive podcast, Kenny Bedwell breaks down how to become a top producer, even without the flashy features competitors might rely on. Drawing from his own experience and industry data, Kenny explains why success in STR doesn’t always mean high capital investment. Instead, it starts with understanding your goals, the dynamics of your market, and how guests make decisions. He walks listeners through the difference between traditional vacation rental markets and emerging STR-friendly areas, revealing how location, expectations, and regulations can influence your strategy more than a hot tub or a game room ever could. Whether you’re just entering the STR game or reassessing your investment strategy, this episode will help you focus your efforts—and your budget—where it matters most. 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:
Resources: Connect with Kenny on LinkedIn 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. | |||
| Implications the Big Beautiful Bill Passing | 15 juil. 2025 | 00:45:23 | |
Are you making real estate investment decisions based on long-term strategy or short-term tax benefits? In this episode, Kenny Bedwell sits down with CPA and tax strategist Ryan Bakke to break down the financial and legal implications of the recent bill passage and what it means for real estate investors. From bonus depreciation strategies to qualifying for deductions, Ryan explains how to navigate evolving tax laws while building a resilient investment portfolio. Whether you're investing in short-term rentals, midterm stays, or traditional long-term properties, this conversation is packed with insights to help you make smarter financial moves. You’ll also hear Ryan's perspective on how government incentives are structured to stimulate the economy and why timing is everything when structuring your deals. Curious how the new tax bill could impact your real estate strategy? Before you lock in your next deal, hit play on this episode with CPA Ryan Bakke. You’ll walk away with smarter ways to approach depreciation, deductions, and portfolio planning in today’s shifting economy. 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:
Guest Bio: Ryan Bakke is a licensed CPA and the founder of Tax Strategy 365, where he helps real estate investors build generational wealth using the tax code. A Trinity Christian College graduate in Accounting and Finance, Ryan began his career at Deloitte, where he led tax technology initiatives for major investment banks. He’s also a former high-level athlete and passionate Christian servant leader. Resources: Connect with Kenny on LinkedIn Join the Tax Strategies For Real Estate Investors Group on Facebook 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.... | |||
| Part 2: Designing Your STR to Maximize Your Returns | 10 juil. 2025 | 00:41:35 | |
When it comes to designing short-term rentals, Becky Jones doesn’t just think in furniture—she thinks in photos. And in today’s market, that visual-first mindset can make or break your ROI. In this episode of the Cash Flow Positive podcast, Kenny Bedwell sits down with design expert and STR consultant Becky Jones to unpack how design, comfort, and guest experience all connect to your bottom line. Becky explains how she balances aesthetics with function to attract better guests, command higher nightly rates, and reduce property issues. From managing remodels to optimizing guest comfort, this episode is packed with actionable advice to make your short-term rental more profitable—and less stressful. 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:
Guest Bio: Becky Jones is an interior designer specializing in designing short-term rentals that are functional, beautiful, and profitable, and founder of Becky Jones Branding. Known for her visual-first approach and guest-centric design strategies, Becky helps STR owners elevate their properties through thoughtful upgrades that enhance comfort, increase profitability, and create memorable guest experiences. Resources: Connect with Kenny on LinkedIn 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. | |||
| Part 1: Designing Your STR to Maximize Your Returns | 08 juil. 2025 | 00:21:08 | |
Think interior design is just about picking pretty furniture? Think again—your return on investment might depend on it. In this solo episode of Cash Flow Positive, Kenny Bedwell reveals why the speed of your short-term rental launch is one of the most critical—and commonly overlooked—factors in maximizing profit. He shares a personal story of how delays during the design process cost him thousands in holding fees and lost revenue, and walks listeners through how to avoid making the same mistake. Kenny breaks down the real financial impact of slow timelines, how to vet designers for efficiency and market alignment, and why identifying your guest avatar should come before any décor decisions. You’ll also learn how to communicate clearly with designers, set firm expectations, and ensure your property is not just beautiful, but bookable. Whether you're launching your first STR or scaling a portfolio, this episode will shift the way you think about design, timelines, and how to protect your bottom line from the start. Ready to turn design delays into revenue wins? Subscribe now and discover more strategies that make your STR cash flow faster. If you've enjoyed this episode of the Cash Flow Positive podcast, be sure to leave a review. Listen now and enjoy! In This Episode You'll Learn:
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. | |||
| Part 2: How to make your STR unique with Micro Designs, with Merritt Haris | 03 juil. 2025 | 00:38:00 | |
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 Merritt Haris. In this episode of the Cash Flow Positive podcast, Kenny Bedwell welcomes Merritt, 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:
Guest Bio: Merritt Haris 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 LinkedIn Merit Badge Property Management 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. | |||
| Part 1: How to make your STR unique with Micro Designs | 01 juil. 2025 | 00:28:38 | |
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:
Resources: Connect with Kenny on LinkedIn 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. | |||
| Part 2: MTR's vs STR's with Vivian Yip | 26 juin 2025 | 00:45:28 | |
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:
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 LinkedIn 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... | |||
| Part 1: MTR's vs STR's | 24 juin 2025 | 00:19:58 | |
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:
Resources: Connect with Kenny on LinkedIn 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. | |||
| Part 2: Save Thousands by Doing This First Before Launching with Kim Fitzpatrick | 19 juin 2025 | 00:38:36 | |
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:
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 LinkedIn PART 2 Kim Fitzpatrick - The STR tortoise vs the hare 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... | |||
| Part 1: Save Thousands by Doing This First Before Launching | 17 juin 2025 | 00:18:00 | |
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:
Resources: Connect with Kenny on LinkedIn 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. | |||
| Part 2: Is It Really a Buyers' Market? with Brenna Carles | 12 juin 2025 | 00:46:36 | |
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:
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 LinkedIn 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. | |||
| Part 1: Is It Really a Buyers' Market? | 10 juin 2025 | 00:29:34 | |
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:
Resources: Connect with Kenny on LinkedIn 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. | |||
| Does the Future of STR's Look Bleak? | 03 juin 2025 | 00:30:46 | |
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:
Resources: Connect with Kenny on LinkedIn 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. | |||
| Part 2: Is Your STR Truly Legal with Katie Johnson | 29 mai 2025 | 00:39:49 | |
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:
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: Connect with Kenny on LinkedIn | |||
| Part 1: Is Your STR Truly Legal? | 27 mai 2025 | 00:16:18 | |
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:
Resources: Connect with Kenny on LinkedIn | |||
| Part 2: Should You Take Direct Bookings with Gil Chan | 22 mai 2025 | 00:42:14 | |
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:
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 LinkedIn The Ultimate Guide to Direct Bookings | |||
| Part 1: Should You Take Direct Bookings? | 20 mai 2025 | 00:19:39 | |
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:
Resources: Connect with Kenny on LinkedIn | |||
| Part 2: Pricing Strategies that Will Change Your Revenue with Jake Cohen | 15 mai 2025 | 00:43:18 | |
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:
Resources: Connect with Kenny on LinkedIn | |||
| Part 1: Pricing Strategies that Will Change Your Revenue | 13 mai 2025 | 00:20:50 | |
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:
Resources: Connect with Kenny on LinkedIn | |||
| Part 2: Finding Success in Competitive Markets | 09 mai 2025 | 00:39:13 | |
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:
Resources: Connect with Kenny on LinkedIn | |||
| Part 1: What Happens When You Buy the Wrong Property | 07 mai 2025 | 00:19:54 | |
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:
Resources: Connect with Kenny on LinkedIn | |||
| Part 2: Unique Airbnbs That Make Serious Money with Ashley Guy | 01 mai 2025 | 00:42:46 | |
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:
Resources: Connect with Kenny on LinkedIn Contact Ashley at ashley@thefemmeinvestor.com | |||
| Part 1: Unique Airbnbs That Make Serious Money | 29 avr. 2025 | 00:21:32 | |
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:
Resources: Connect with Kenny on LinkedIn The Pumpkin Plan: A Simple Strategy to Grow a Remarkable Business in Any Field | |||
| Part 2: What Mortgage Fraud and LLCs Have in Common with Parker Borofsky | 24 avr. 2025 | 00:44:45 | |
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:
Resources: Connect with Kenny on LinkedIn Wealth Builders Mortgage Group | |||
| Part 1: What Mortgage Fraud and LLCs Have in Common | 23 avr. 2025 | 00:22:42 | |
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:
Resources: | |||