Podcast
Cash Flow Positive
Hosted by Kenny Bedwell · EN
Step into the world of Cash Flow Positive, where the secrets to short-term real estate success await. Join our host, Kenny Bedwell, each week as he unveils a treasure trove of strategies for identifying, acquiring, and scaling profitable rental deals. In Part 1, experience a whirlwind of knowledge in just 15 minutes, packed with actionable insights and proven techniques. Then, immerse yourself in captivating interviews lasting 20 to 45 minutes, featuring industry mavens who've mastered the very concepts you've learned. Whether you're a seasoned pro or just starting out, Cash Flow Positive is your roadmap to unlocking the full potential of your property portfolio. Don't miss your chance to thrive in the dynamic world of real estate investment – tune in now!
30episodes
Episodes
Newest firstAll episodes
This Mistake Just Cost Me THOUSANDS
2w ago00:16:59Tap to summarizeEver lost thousands simply by trusting the wrong process or the wrong person?Kenny Bedwell returns from a break not just with fresh life perspective but with the hard-won, painful truths of renovating an 1848 boutique hotel from hundreds of miles away. This episode dives deep into the exact mistakes that cost him actual cash, and even more valuable time from contractor sequencing chaos to shipments gone missing to why “project management by Zoom” is a surefire road to blown budgets.If you own or plan to own any STR, now’s the time to learn how to lead projects to the finish line without bleeding money. Skip this one, and you risk repeating the most expensive rookie mistakes in the book. Listen now for practical, brutally honest strategies you’re not getting anywhere else.Timestamped Highlights00:11 – The real cost of learning by fire on big renovation deals01:47 – The one-day trip that revealed everything broken about remote project management03:14 – Why showing up in person sparks a momentum shift with contractors05:25 – How a simple shipping oversight vanished $2,000 overnight06:10 – Where even pros screw up sequencing and lose weeks08:08 – The shocking truth about contractor incentives (and why they don’t care)09:25 – The proven fix that instantly cuts through project chaos12:10 – Why virtual management almost always leads to costly delays15:44 – Life-after-loss: Exact steps to prevent these disasters in your next STR projectMentioned ResourcesWayfair consolidated delivery serviceAmazon (referenced for shipping)Important LinksWant us to find the deals for you? https://strinsights.com Get Top Markers for STRs (2025) - https://rebrand.ly/28b1df Instagram – @kenny_bedwellYouTube – Cash Flow PositiveLinkedIn – Kenneth BedwellCash Flow Positive is an original podcast hosted by Kenny Bedwell. Brought to you by STR Insights. Production and editing by Podcast Your Brand.
Transcribe →Two Secrets to Scaling a Successful Portfolio
May 500:24:11Tap to summarizeAre you stuck grinding but never really escaping?In this punchy solo episode, Kenny Bedwell drops the curtain on the two proven secrets that transformed his own portfolio, and he does not sugarcoat the realities. With sharp stories of scrappy beginnings, W2 frustration, and the gut-check moment that forced him to choose between comfort and growth, Kenny Bedwell dives deep into the real reasons investors stall out.Listen in if you’re ready to challenge the “just buy another unit” mentality, discover why time (not money) is your biggest bottleneck, and learn exactly what stops even high-income professionals from breaking through. Miss this episode and you’re gambling with years of wasted effort, stretching your goals into a never-arriving someday. Hit play now for straight answers you truly won’t find recycled elsewhere.Timestamped Highlights00:00 – What most investors get wrong about “scaling up”01:58 – The single conversation that shattered my old plan03:49 – The moment I made triple rent… and everything changed05:25 – The ugly reality of juggling W2, family, and side hustles08:23 – The corporate drama that forced my hand10:22 – Why time, not money, is your real shortcut to freedom14:42 – Why “bold” isn’t gambling and how I protect against disaster16:40 – The uncomfortable moves that led to explosive cash flowMentioned ResourcesAirbnbBiggerPocketsImportant LinksWant us to find the deals for you? https://strinsights.com Get Top Markers for STRs (2025) - https://rebrand.ly/28b1df Instagram – @kenny_bedwellYouTube – Cash Flow PositiveLinkedIn – Kenneth BedwellCash Flow Positive is an original podcast hosted by Kenny Bedwell. Brought to you by STR Insights. Production and editing by Podcast Your Brand.
Transcribe →Who Is ACTUALLY Booking Your Property?
Apr 2800:27:07Tap to summarizeAre your short-term rentals sitting empty while your competitors rake in bookings? You might be targeting the wrong guest without even knowing it. In this tough-love, numbers-driven solo episode, Kenny Bedwell, founder of STR Insights, reveals the six REAL buyer personas that drive every booking decision and why most hosts get it dead wrong.Cut through the industry fluff: This episode breaks down how each persona thinks, what drives their decisions, and how seasonality radically shifts who you’re really marketing to. Whether you’re struggling to fill high-end properties, want to squeeze more out of the low season, or just avoid attracting guests who tank your reviews, this episode gives you direct, actionable insight you simply won’t find on other STR podcasts.Stop the guesswork. Listen right now to protect your cash flow, outsmart your competition, and attract the guests you actually want. These frameworks are exclusive, urgent, and can change your booking game overnight.Timestamped Highlights00:02 – Dad shirts are back… but is your STR guest strategy stuck in winter?00:44 – The secret reason you keep attracting the “wrong” guests (and how to fix it)03:03 – Why budget buyers will ignore your amenities—and the pricing trap most hosts fall into07:32 – Value seekers, Costco logic, and the most common STR buyer (are you missing easy profits here?)10:46 – The convenience persona: Why location, reviews, and guarantees can replace discounts13:17 – Experience seekers exposed: Social media-worthy guests—and the Instagram marketing mistake16:55 – Luxury buyer drama: When high expectations drive guests to cancel… and why “luxury” is more than just a word20:29 – Occasion seekers and the money left on the table when you ignore group dynamicsMentioned ResourcesAirbnb LuxeCostco, Sam’s Club, Dollar Tree (buyer mindset examples)Instagram (direct booking for experience stays)Marriott, Sheraton (hotel chains, buyer persona contrasts)Important LinksWant us to find the deals for you? https://strinsights.com Get Top Markers for STRs (2025) - https://rebrand.ly/28b1df Instagram – @kenny_bedwellYouTube – Cash Flow PositiveLinkedIn – Kenneth BedwellCash Flow Positive is an original podcast hosted by Kenny Bedwell. Brought to you by STR Insights. Production and editing by Podcast Your Brand.
Transcribe →STR Vanity Metrics to Avoid
Apr 2100:23:06Tap to summarizeAre you obsessed with high booking rates, glowing reviews, or six-figure revenue? What if those metrics are secretly keeping you broke and blind to your property’s true potential?In this punchy solo episode, Kenny Bedwell, founder of STR Insights and host of Cash Flow Positive, exposes the most overhyped “STR swear words” in the business, metrics that sound good but can destroy your bottom line if you chase them blindly. You’ll learn why occupancy rate, guest ratings, and even jaw-dropping gross revenue can cost you time, money, and deal flow if you don’t dig deeper.Don’t gamble your freedom or future on surface numbers. Listen now to dodge expensive pitfalls, outsmart the sharks, and finally see REAL cash flow. Miss this episode, and you’ll risk overpaying for duds nobody else wants to touch.Timestamped Highlights00:02 – The “STR swear words” that make Kenny Bedwell furious (and should make you nervous)02:26 – The real story behind high occupancy rates—why 100% bookings can be a trap04:24 – The 46% rule: How a “low” occupancy rate led to insane ROI (and less headaches)06:53 – The year-round bookings myth and why chasing monthly returns kills your annual gains08:00 – A 4.89-star rating, $60K more profit—what everyone gets wrong about reviews10:03 – Why high bookings and high ratings still don’t guarantee cash flow (and what to demand instead)13:23 – Gross revenue exposed: How sellers weaponize the most misleading metric in STR16:13 – $5K “brag posts” vs. $2K net: The social media profit illusion you must avoidMentioned ResourcesVRBOAirbnbFacebookProfit & Loss statements (PNL)Booking Lead Time (industry trend)“Superhost” and Airbnb algorithm factorsImportant LinksWant us to find the deals for you? https://strinsights.comGet Top Markers for STRs (2025) - https://rebrand.ly/28b1dfInstagram – @kenny_bedwellYouTube – Cash Flow PositiveLinkedIn – Kenneth BedwellCash Flow Positive is an original podcast hosted by Kenny Bedwell. Brought to you by STR Insights. Production and editing by Podcast Your Brand.
Transcribe →BIG NEWS: Airbnb listened to this podcast!
Apr 1800:19:51Tap to summarizeAre your Airbnb profits slipping and you don’t know why? Imagine waking up to a revenue model change that could make or break your short-term rental business. In this urgent solo episode, Kenny Bedwell breaks open the truth behind Airbnb’s blockbuster reversal on host fees, the quiet switch nobody was supposed to notice, but every smart investor needs to understand today.You’ll discover what’s really behind the fee flip, how it impacts your property’s ranking and bookings, and exactly how to adapt before the window slams shut. Don’t let another booking cycle pass you by while others get ahead. If you care about maximizing profit and avoiding algorithm disaster, you need these exclusive, data-backed strategies right now. Only Cash Flow Positive gives you the real numbers, the pitfalls, and the playbook to WIN before the changes vanish again!Timestamped Highlights00:00 – The wildest podcast cold open yet—did Airbnb really listen to this show?01:45 – The “split fee” is BACK: What it means and why it matters for your profit05:40 – Insider data: What happened to hosts’ bookings and income after the single fee switch08:30 – Why Airbnb claims hosts get “more bookings” (and why that’s a vanity metric trap)12:55 – The one move you must make in your property management system to cash in17:00 – The truth about algorithm rankings and dropping your fees (what Airbnb won’t say)18:40 – Top-performing properties vs. average: Who really survives policy chaos?20:00 – Exactly how to prepare for June’s next pricing reset and outsmart 90% of hostsMentioned ResourcesVRBO (competitive shifts and booking volume)Airbnb Host Fee Structures (split fee vs single fee)Property Management Software (PMS)Emile Sakhel (industry revenue manager)Important LinksWant us to find the deals for you? https://strinsights.com Get Top Markers for STRs (2025) - https://rebrand.ly/28b1df Instagram – @kenny_bedwellYouTube – Cash Flow PositiveLinkedIn – Kenneth BedwellCash Flow Positive is an original podcast hosted by Kenny Bedwell. Brought to you by STR Insights. Production and editing by Podcast Your Brand.
Transcribe →Part 2 ft. Ryan Cadwell - Exit Strategy First: Why Most Investors Build Backwards: Exit Strategy First: Why Most Investors Build Backwards
Apr 1000:43:47Tap to summarizeEver wondered why real estate investors lose big while others exit with effortless wins?In this can’t-miss episode, Kenny Bedwell gets brutally real with veteran broker and multi-cycle investor Ryan Cadwell, exploring why the majority of investors walk into deals blind, and what separates the survivors from the victims when markets shift. You’ll hear hard-won lessons from the Great Recession to today, the overlooked math that keeps you safe, and why your emotions are quietly sabotaging your wealth.Stop playing checkers in a chess market. Listen now to learn the proven, data-backed playbook for winning with your exit before you ever buy. Miss this, and you’ll pay a premium for mistakes you could have avoided. Your future self is begging you not to skip these strategic insights, no fluff, zero hype, and exactly what the gurus won’t warn you about.If you want to avoid painful losses, stop buying blind, and gain immediate edge in today’s market—this episode is your ticket. Listen now before your competition does.Timestamped Highlights00:00 – The raw mistake that nearly took down veteran investors in ‘0805:12 – Why BlackRock’s latest moves are the market signal you can’t ignore10:07 – How optimism bias and emotional attachment wreck your returns14:19 – The 7 Whys Framework that exposes what investors really want17:34 – If you LOVE a deal, why that’s your loudest red flag20:17 – The data traps: Outdated numbers, ignored expenses, and the illusion of “free” vacation homes25:54 – Rookie math that destroys deals and the exit-first equation that saves you35:02 – The 10-minute investment journal habit that will transform your discipline (and profit)About The GuestRyan Cadwell is a Certified Property Manager and Principal partner at Resolute RDM with nearly two decades of hands-on investment, development, and commercial consulting experience. Ryan’s roots go back to family rentals at age 12, spanning every market cycle from the Great Recession to post-COVID surges. He’s known for his surgical approach to due diligence, asset management, and the no-nonsense brokerage advice trusted by seasoned and rookie investors alike.🔗 LinkedIn | WebsiteMentioned ResourcesInvestment Journaling (habit Ryan recommends)Reference to BlackRock’s market activityCapital expense planning/cost segregation (advanced tax and asset strategies)Important LinksWant us to find the deals for you? https://strinsights.com Get Top Markers for STRs (2025) - https://rebrand.ly/28b1df Instagram – @kenny_bedwellYouTube – Cash Flow PositiveLinkedIn – Kenneth BedwellCash Flow Positive is an original podcast hosted by Kenny Bedwell. Brought to you by STR Insights. Production and editing by Podcast Your Brand.
Transcribe →Part 1 - Exit Strategy First Why Most Investors Build Backward
Apr 900:24:18Tap to summarizeAre you racing to buy more properties but never stopping to ask, “What’s my end game?” If you want true financial freedom from short-term rentals—not just another job—you need a proven, numbers-driven exit plan.Host Kenny Bedwell, founder of STR Insights, reveals why most investors build backwards and sabotage their long-term wealth. This episode exposes why cash flow is not the secret, how to use data to scale faster, and the killer reason your “forever” property usually isn’t. Kenny tears down common myths, puts hard numbers behind every decision, and lays out a blueprint for achieving wealth beyond the next tax season.Listen now and escape the newbie trap, avoid five-figure mistakes, and get the exclusive strategic insights trusted by top-performing STR investors. Your next level depends on understanding your exit, and no one else is telling you this.Timestamped Highlights[00:00] – Why today’s cash flow obsession is tricking investors out of real wealth[00:38] – The “backwards builder” myth and how serial investors think differently[02:58] – A jaw-dropping stat: Why 3–5 years is the true STR hold window[04:20] – The ROI vs ROE showdown when selling trumps holding[06:44] – The 1031 dilemma: Are you setting yourself up to be stuck?[09:09] – The tax savings rabbit hole and why one year of relief kills your strategy[11:09] – Kenny’s market-moving confession: What happens when a crowd follows your lead[14:19] – How to spot the exact “sell trigger” (and double your portfolio wealth)[19:02] – The trap of quantity over quality—how chasing properties makes you your own worst bossMentioned Resources1031 Exchange strategyReturn on Equity (ROE)Return on Investment (ROI)Important LinksWant us to find the deals for you? https://strinsights.com Get Top Markers for STRs (2025) - https://rebrand.ly/28b1df Instagram – @kenny_bedwellYouTube – Cash Flow PositiveLinkedIn – Kenneth BedwellCash Flow Positive is an original podcast hosted by Kenny Bedwell. Brought to you by STR Insights. Production and editing by Podcast Your Brand.
Transcribe →Part 2: Emile Sakhel - How Airbnb's Fee Change Impacts Hosts
Mar 2600:41:11Tap to summarizeIs your short-term rental income safe, or is the new Airbnb fee model slashing profits behind your back? Most hosts have no idea how much they’re really losing or why Vrbo is suddenly on the rise.In this urgent, myth-busting episode, Kenny Bedwell sits down with revenue mastermind Emile Sakhel (Founder, Pricing by Mira) to expose the surprising ripple effects of Airbnb’s 15.5% host-only fee. From real-world numbers to emotional guest decisions, you’ll learn exactly who’s winning and who’s losing after this game-changing shift. Discover proven tactics for protecting your net cash flow, avoiding “measurement mistakes,” and leveraging platform psychology before your next competitor.Listen now to stop the silent drain on your profits. Avoid costly traps and get exclusive strategies you won’t hear from industry gurus or Facebook groups. This episode could mean the difference between cash flow victory and yearly regret.Timestamped Highlights[00:00] – Meet Emile Sakhel: The psychology (and math) of true STR profits[00:02:37] – Airbnb’s shocking fee switch: The little-known 40% mistake sabotaging hosts[00:04:14] – Why an 18.34% markup matters and the hidden math most hosts miss[00:07:20] – The #1 mistake investors make when underwriting STR deals post-fee change[00:10:09] – True or false: Did raising prices kill your ranking… or actually help?[00:12:17] – Who’s quietly winning? The Vrbo surge nobody saw coming[00:16:13] – Subscription secrets: How some hosts are crushing Airbnb margins on Vrbo[00:23:17] – Price parity panic: Why guests (and algorithms) punish sloppy pricing[00:31:19] – How to bulletproof your underwriting—get net right or get wreckedAbout The GuestEmile Sakhel is the founder of Pricing by Mira, a revenue management consultancy transforming how short-term rental operators pursue profit. Known for his deep-dive approach to revenue psychology, system building, and outperforming market RevPAR by up to 4x, Emile is a trusted educator and advisor for ambitious investors. He’s also the creator of My Revenue Academy, empowering hosts to master the art of pricing and platform strategy for themselves.🔗 LinkedIn | Website | Facebook | InstagramMentioned ResourcesMy Revenue AcademyAirDNAPriceLabsRankBreezeVrbo (and “One Key” promo system)DARM Conference (Data & Revenue Management)Important LinksWant us to find the deals for you? https://strinsights.com Get Top Markers for STRs (2025) - https://rebrand.ly/28b1df Instagram – @kenny_bedwellYouTube – Cash Flow PositiveLinkedIn – Kenneth BedwellCash Flow Positive is an original podcast hosted by Kenny Bedwell. Brought to you by STR Insights. Production and editing by Podcast Your Brand.
Transcribe →Part 1: How Airbnb's Fee Change Impact Hosts
Mar 2500:21:20Tap to summarizeAre you leaving hidden cash on the table after Airbnb’s dramatic fee overhaul or, worse, losing it without knowing? In this data-charged episode, Kenny Bedwell breaks down the most misunderstood shift in recent STR history: Airbnb’s transfer of guest fees to hosts. If you’ve ever worried you’re charging the wrong nightly rate, or you’re blindsided by shrinking net returns despite steady bookings, you’re not alone.With surgical clarity (and zero fluff), Kenny Bedwell reveals who actually won, who lost, and why only the savviest hosts survived. This isn’t another regurgitated news brief, it’s your exclusive masterclass on elasticity, ranking risk, and tactical pivots that could save (or sink) your STR portfolio.Listen now to avoid sabotaging your own profits, act before your competition does, and get the unfiltered inside scoop you won’t find scrolling social or Reddit.Timestamped Highlights[00:00] The day everything changed: Airbnb’s shocking fee flip and what most hosts missed[01:08] The chaos and confusion: Why hosts panicked over math and which ones got it right[02:01] The 30/30/40 rule: Why most hosts failed to adjust and what it cost them[05:57] The big economic reveal: Does the guest really care, or do hosts pay the highest price?[07:09] The VRBO effect: How Airbnb’s move handed business to its rivals[09:13] Secret algorithms: How fees, ranking, and property uniqueness now decide your fate[11:14] Elastic vs. inelastic: Why “average” properties are at greatest risk in 2024[15:20] How to future-proof your portfolio: Building your moat before the next big changeMentioned ResourcesVRBO (Vacation Rentals by Owner)Ranking algorithm discussions on AirbnbImportant LinksWant us to find the deals for you? https://strinsights.com Get Top Markers for STRs (2025) - https://rebrand.ly/28b1df Instagram – @kenny_bedwellYouTube – Cash Flow PositiveLinkedIn – Kenneth BedwellCash Flow Positive is an original podcast hosted by Kenny Bedwell. Brought to you by STR Insights. Production and editing by Podcast Your Brand.
Transcribe →The Opportunity Cost of Buying Today
Mar 1900:24:13Tap to summarizein a short-term rental? This episode will shake you out of indecision and challenge everything you thought you knew about market timing. Kenny Bedwell, founder of STR Insights, goes straight to the heart of opportunity cost, showing how hesitation can quietly devastate your wealth, your tax savings, and even your freedom.Packed with frank, numbers-backed stories and actionable logic, Kenny breaks down why waiting for “the perfect market” is an investor’s biggest mistake and how missed months equal missed thousands. If you’re tired of guru hype and ready for practical data-driven education, tune in now. The longer you wait, the more you lose.Listen today to avoid costly inaction and gain exclusive insight no algorithm or “expert” will give you. This episode is your wake-up call.Timestamped Highlights[00:00] – Why “timing the market” is just a myth (no crystal ball needed)[00:02:42] – The shocking truth about real estate crashes and market cycles[00:05:07] – The finite supply of “good deals” and how STR seasonality affects your shot[00:07:18] – Real-life regret: Kenny’s confessions about not acting faster during COVID[00:08:33] – How opportunity cost quietly steals your cash flow every missed month[00:12:42] – Tale of two investors: Who wins and why taking action fuels exponential growth[00:16:47] – “Ugly” puzzle properties: Why complexity signals massive upside[00:22:17] – The secret to unlocking deals others fear (and how Kenny found a jackpot)[00:23:30] – Kenny’s final brutal advice: Only act when you really have the meansMentioned ResourcesGoldman Sachs – Market rate forecast referenceProper, Steadily – Insurance companies for STRsWatkins Glen lottery system (STR permitting example)Bonus depreciation (tax strategy for STR buyers)Important LinksWant us to find the deals for you? https://strinsights.com Get Top Markers for STRs (2025) - https://rebrand.ly/28b1df Instagram – @kenny_bedwellYouTube – Cash Flow PositiveLinkedIn – Kenneth BedwellCash Flow Positive is an original podcast hosted by Kenny Bedwell. Brought to you by STR Insights. Production and editing by Podcast Your Brand.
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