Cash Flow Positive

Ever 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exposes what investors really want17:34 – If you LOVE a deal, why that’s your loudest red flag20:17 – The data traps: Outdated numbers, ignored expenses, and the illusion of “free” vacation homes25:54 – Rookie math that destroys deals and the exit-first equation that saves you35:02 –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.

Are 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.

Is 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.

Are 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.

in 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.

Ever wonder why some real estate investors explode their portfolios while others fumble with endless spreadsheets? Today, Kenny Bedwell pulls back the curtain on the STR Scale Summit and shares proven strategies, uncommon lessons, and hard truths from inside the event. If you crave more than generic advice, Kenny’s frank, numbers-driven breakdowns of scaling, partnerships, and real-world deal structures will give you exactly what you need.This episode hits everything from micro resorts, boutique hotels, and creative financing, to why relationships—not just deal math—make or break your business. It’s the shortcut to avoid expensive mistakes, get access to exclusive insider tactics, and finally feel confident about scaling your STR game.Listen now, because next year’s opportunities won’t wait, and this episode delivers practical, actionable takeaways you won’t get anywhere else.Timestamped Highlights[00:00] – STR Scale Summit recap: Will you be a victim of FOMO or grab your victory?[00:01:24] – Why micro resorts are revolutionizing the cash flow game—economies of scale revealed[00:03:15] – Inside boutique hotel investing: Real costs, real risks, and a live tour that shocked the crowd[00:04:13] – The “whoopsie budget”—the surprising truth that blows up perfect spreadsheets[00:05:47] – The 3 C’s of STR investing: Cute, Comfortable, Clean… and not over-amenitizing[00:06:47] – Kenny’s “secret formula” for $100K+ cash flow properties—do you really know what to look for?[00:07:25] – Raising capital, partnerships, and how not to get screwed—unfiltered deal structure lessons[00:12:02] – Trust but verify: The hard rules for protecting yourself in partnerships[00:13:08] – Why commercial lenders care about relationships more than your spreadsheets[00:16:15] – The game-changing logistics every big investor now needs from Wayfair[00:19:18] – Relationship ROI: Why “having a guy” beats hiring the big box company every timeMentioned ResourcesSTR Scale SummitBoutique hotel investingWayfair Professional account managerBRRRR strategyCommercial lending – Mark Sacco506(c) and 506(b) syndication structuresImportant 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.

Ever worry that one bad cleaning review could shatter your STR returns or even threaten your bookings? Imagine systematically boosting your ratings, delighting guests, and generating reliable cash flow, all simply by revolutionizing your approach to quality and teams.This episode, host Kenny Bedwell sits down with short-term rental powerhouse Stacey St. John, whose unique playbook has catapulted her from long-term investor to founder of a wildly impactful community and management empire. Together, they destroy myths about “minimum viable cleaning,” break down why most owners are still losing thousands, and share the real leverage hidden in systems, mindset, and (yes) the legendary “toilet test.”If you’re serious about staying competitive, maximizing income, and avoiding industry shakeout, you need these exclusive upgrades now, not next season. Listen in for data-backed strategies that no other podcast is telling you about.Timestamped Highlights[00:00] – A wild Ohio-to-beach vacation trend exposes a hidden rental goldmine[00:02:13] – COVID, eviction bans, and the shocking trigger for a rental pivot[00:03:33] – Why oceanfront for under $100k changed everything (and you missed it…)[00:05:08] – Accidentally creating a 66,000-member community and why it matters[00:11:46] – The real numbers: How “clean team” upgrades spiked ratings and revenue[00:15:34] – Cattle call cleaners, uncomfortable truths, and busting industry norms[00:29:40] – The “toilet test” and secrets of inspection culture that make or break your reviews[00:41:56] – Building a true team: How to transform cleaners into your STR profit weaponMentioned ResourcesFemale Short-Term Rental Investors Facebook GroupCozy GetawaysBook: Live Big by Stacey St. JohnAirbnbVRBOAbout the GuestStacey St. John is a data-driven short-term rental investor, educator, and founder of Female Short-Term Rental Investors, the largest women’s STR community with over 66,000 members. Based in Cincinnati and operating properties across Myrtle Beach and Ohio, Stacey is also CEO of Cozy Getaways, where her focus on quality, systems, and empowering women has set new industry benchmarks for guest experience and financial performance.🔗 LinkedIn | Website | YouTube | Facebook | InstagramImportant 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.

Are your short-term rental photos quietly costing you thousands in lost revenue? Most hosts lock in their listing photos and hope for the best, but what if a single, data-backed tweak could drive a double-digit leap in bookings? In this eye-opening solo episode, Kenny Bedwell pulls back the curtain on a simple yet game-changing hack designed to bump your STR revenue by 15% (or more). Forget the tired advice about marketing and pricing. Kenny gets razor-specific about leveraging seasonality, booking lead time, and the psychology of Airbnb’s search algorithm so you can outshine saturated competition and start ranking higher, faster.Don’t miss this episode if you’re done losing bookings to “average” listings or fighting the algorithm blind. Tune in now or risk staying buried while others claim the cash flow you deserve. This is an exclusive, numbers-driven tactic you won’t find in the usual STR playbooks!Timestamped Highlights[00:00] The #1 mistake hosts make that kills their revenue potential[00:00:45] Why seasonality crushes static listing photos every time[00:01:34] Booking lead time: the underrated, live metric that changes everything[00:02:41] Natural disasters, “anomaly events,” and their surprising aftermath in STR bookings[00:06:07] Want more bookings? Here’s how your photos can attract the right demand, fast[00:07:49] The wrong photo at the wrong time: Are your snow pics scaring off summer travelers?[00:11:01] What amenities to spotlight for instant desire in every season[00:12:56] Christmas magic on Airbnb: the tiny photo tweak most hosts overlook[00:14:56] How the Airbnb algorithm picks winners (and why early bookings are your lifeline)[00:17:17] Are you overthinking seasonal photos? Kenny’s zero-fluff take on what “enough” really meansMentioned ResourcesAirbnb search algorithm strategies (in-episode explanation)Watkins Glen property case studyBooking lead time analysisImportant 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.

Are you tired of the hype, confusion, and conflicting advice dominating short-term rental investing? What if the real secret to real estate freedom isn’t just how you operate, but how you buy?In this solo episode, Kenny Bedwell gets brutally honest about the surprising ways investors lose money by overpaying, believing guru projections, and missing the “money on the buy” formula. He shreds industry misconceptions and unpacks the exact math and legal details behind ARV (After Repair Value), showing how cash flow and forced appreciation are the double-headed dragon of breakthrough investing.Tune in now to sidestep costly mistakes, stop relying on rumors, and get exclusive, actionable clarity you won’t hear from brokers, TikTok gurus, or random Facebook groups. Listen before you make your next offer or risk losing your shot at financial freedom!Timestamped Highlights[00:00] – Why operating isn’t enough: The unseen risk of buying wrong[00:01:29] – Do you really have to be a top operator, or is buying right the real unlock?[00:03:02] – The two proven ways properties actually make money and where most get it wrong[00:04:21] – ARV exposed: How emotional upgrades mislead you (and what counts as real value)[00:05:35] – The appraisal rollercoaster: Millionaires or victims of ‘desk appraisals’?[00:06:33] – Savvy investors spot the difference: How to cut through market myths[00:10:14] – Buying at the top of the market—why every improvement becomes worthless[00:13:31] – Legal bedroom drama: Why adding beds can blow up your deal[00:16:49] – Pools, game rooms, and garages: What really moves the needle (and what’s a sunk cost)[00:18:13] – Are you using the wrong comps? How one tweak can save or sink your entire investment[00:24:25] – The price per square foot strategy: How real pros calculate ARV (step-by-step)[00:25:30] – The 70% rule and double-headed approach: Protecting your cash flow and upside for 2026Mentioned ResourcesPrice Per Square FootARV (After Repair Value) CalculationLegal bedroom requirements (egress window, heating, cooling, etc.)Desk appraisal70% RuleCash flow and appreciation modelsImportant 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.

Are you stuck waiting for the “big crash” to finally buy your dream short-term rental? What if that crash already came…and left you behind?In this radically honest episode of Cash Flow Positive, host Kenny Bedwell brings on industry powerhouse Avery Carl for an unfiltered look at the post-pandemic real estate landscape. Avery Carl pulls from 10+ years and 5,000+ deals to reveal why smart investors are thriving while others are paralyzed by analysis, hype, and old strategies that simply don’t work anymore. If you want no-BS answers on timing the market, dealing with stubborn sellers, navigating high-interest rates, and finally making offers that actually win, you’ll find them here.Don’t miss this straight-shooting, numbers-backed conversation with actionable takeaways for buyers AND sellers. Listen now to avoid the pain of missing out (again), capitalize on this rare window, and sidestep the false promises dominating today’s real estate noise. The market’s moving fast, and this episode is your roadmap to real victory.Timestamped Highlights[00:00] Startling confessions: Why the crash you’re waiting for already happened[00:02:31] The brutal math on home prices—what truly stops them from falling[00:03:39] Are you “catching a falling knife?” The secret cost of waiting for perfection[00:07:51] How the offer game has totally changed (and hacks for today’s market)[00:11:04] Real talk for sellers: Tough love, tough comps, and the biggest mistakes to avoid in 2024[00:17:16] Stop buying ugly houses: Emotional pitfalls and winning tricks for higher resale value[00:20:25] Beach access, views, and “turds with sprinkles”—what REALLY draws cash flow (and what kills it)[00:26:48] The amenities arms race: At what point does “over-improving” backfire?[00:33:36] Who’s buying next? The ignored risk that threatens every STR investor’s exitMentioned ResourcesSmarter Short Term Rentals – Facebook groupSTR Scale SummitBRRRR Strategy by David GreeneBiggerPocketsAbout the GuestAvery Carl is the CEO and Founder of The Short Term Shop, the nation’s largest short-term rental-specific real estate brokerage. With more than 5,000 vacation rental transactions and 250+ personal investment doors, she’s a leading voice on how to think—AND act—smart in today’s unpredictable market. Avery’s blunt, data-backed advice and “own what works” mentality make her a must-follow for anyone serious about building wealth through real estate.🔗 LinkedIn | WebsiteImportant 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.

Are you sick of recycled guru advice and worried about making the wrong move in today’s wild STR market?Kenny Bedwell cuts through the noise with brutal honesty and stark data, giving you the freedom to say no to hype and yes to cash-flow-positive deals.In this punchy solo episode, he dives into the real state of the industry for 2026: how incentives twist advice you hear, why copycat “hotspots” will cost you big, and the practical innovations it takes to own your future profits. From dissecting shady vendor deals to revealing why being different is safer than ever, Kenny Bedwell arms you with rare, actionable insights.Don’t get taken for a ride. Listen now to dodge avoidable disasters and seize proven, data-driven strategies you won’t find in the TikTok echo chamber. This is your unfair advantage, before the market leaves you behind.Timestamped Highlights[00:00] — The explosive problem with industry advice everyone ignores[00:01:06] — Why “I just want to help” usually hides a dollar sign[00:04:13] — The hidden motives that can quietly sink your next deal[00:05:50] — Who’s selling short-term rental hope… and who’s selling hype?[00:07:16] — The low-rate loan trap: what most investors miss before it’s too late[00:10:04] — Realtor myths exposed: why those “best markets” rarely are[00:11:01] — Overhyped markets vs. overlooked goldmines: what really works in 2026[00:17:02] — The real shortcut to stand-out STR success (hint: it’s not more decor)Mentioned ResourcesDSCR loans / second home loansAirdna (indirect mention: short-term rental data providers)STR Scale SummitSTR Wealth ConChatGPT (tool for creative brainstorming)Wayfair (STR furnishing and amenity sourcing, referenced in context)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.

When’s the last time your calendar made you real money? Most hosts set their pricing, cross their fingers, and hope the bookings roll in… all while leaving thousands on the table and letting holidays sabotage their revenue. In this actionable episode, Kenny Bedwell sits down with powerhouse educators Annette Grant and Sarah Karakaian from Thanks for Visiting to unpack how “mom and pop” operators can finally run their rentals like strategic businesses.Packed with real-world tactics, this episode exposes costly blind spots in operations, team structure, and revenue management you can fix now. You’ll get proven approaches for transforming your calendar into a cash-generating asset, especially with high-risk holiday traps looming in 2026.Listen now to skip overwhelm, outmaneuver your market, and grab the edge most hosts will miss. Wait, and you risk another year of margin-sucking mistakes… These battle-tested strategies are the difference between surviving and thriving, and you won’t hear them anywhere else.Timestamped Highlights[00:00] “You’re not running a business…you’re bleeding money”—the surprising mindset shift every STR host needs[00:05:37] How to build your dream STR team (hint: it’s way more than a cleaner and remote lock)[00:12:40] Panic pricing exposed! Why most hosts sabotage their revenue—and the wild fix you need[00:16:05] The “Nashville hack” for algorithm dominance—how to rewrite your listings like a pro and win more visibility[00:18:16] The untapped event strategy: Why a board game convention can outperform the Arnold Fitness event and what it teaches about true demand[00:19:35] Squeeze every dollar from existing bookings—transforming “dead space” in your calendar into pure profit[00:26:33] 2026’s high-risk holidays decoded: How a Friday July 4th or Christmas can kill (or skyrocket) your revenue if you’re not prepared[00:32:36] Why revenue managers alone won’t save you—and the critical questions smart owners must ask to beat the competitionMentioned ResourcesThanks for Visiting BootcampPriceLabs Market DashboardAirbnbVRBODynamic Pricing Tools (e.g., PriceLabs)Arnold Fitness ExpoBoard Game Convention (Columbus, OH)About the GuestsSarah Karakaian and Annette Grant are co-founders of Thanks for Visiting, the revered short-term rental education brand helping thousands of hosts maximize profit and hospitality through operations excellence. As STR investors, property managers, and top trainers, they’ve coached hosts across the US to ditch hobby status, treat their rentals like real businesses, and outperform the market with data-driven, proven methods.🔗 Website | Instagram | YouTube | LinkedIn: Sarah Karakaian | LinkedIn: Annette GrantImportant 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.

Are you hustling for cash flow but secretly terrified of buying the wrong property? What if you’re obsessing over the wrong number… and it’s killing your returns?In this punchy, numbers-driven solo, Kenny Bedwell (founder, STR Insights) reveals the overlooked metric that separates the real STR winners from the wannabes: ARV (After Repair Value). He breaks down why focusing only on cash flow or gross revenue is the most common — and expensive — mistake investors make, especially as the market shifts in 2026 and beyond. Learn how the savviest investors lock in instant equity, create options, and bulletproof their portfolios… while everyone else chases hype.Don’t wait. Listen now to avoid the pain of a dud deal and embrace an approach that gives you more freedom, flexibility, and long-term wealth. There’s no fluff here, just the data-driven truth no one else will say out loud.Timestamped Highlights[00:00] The #1 investor mistake that’s rarely talked about—are you making it?[00:02:18] Why cash flow worship could backfire: brutal deal math exposed[00:03:45] The California trap: when betting on appreciation costs you real money[00:06:30] The $450k blunder: how over-improving can destroy your exit options[00:10:17] The illusion of “winning”—when high gross revenue is secretly a loss[00:14:21] Why 2026 will punish investors who ignore forced appreciation[00:17:01] Case study: how to engineer instant equity and triple your exits[00:24:47] Scouting for gold: how to spot ARV spreads in crowded markets[00:29:47] The real goal: buying so well, operations become nearly stress-freeMentioned ResourcesPriceLabsAirbnb (smart pricing)Hunter, New York (market example)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.

Are you really leveling up or just running in circles with your real estate deals? If you’ve ever raced through a 1031 exchange, felt stuck chasing “passive” income that never arrives, or lost sleep over looming capital gains taxes, this episode is your game-changer.Host Kenny Bedwell sits down with Brett Swarts, renowned capital gains tax strategist, for a blunt, numbers-driven masterclass on using Deferred Sales Trusts (DSTs) to crush the limitations of traditional 1031 exchanges and unleash truly passive income. Together, they dismantle common myths, reveal jaw-dropping case studies, and map out the step-by-step moves to reclaim your time, freedom, and cash flow.Stop letting taxes and deadlines push you into the wrong deals. Listen now to discover how DSTs can hand you ultimate flexibility and real peace of mind. This exclusive episode is packed with proven strategies and insider tactics you won’t find anywhere else. Tune in now before you overpay for your next deal!Timestamped Highlights[00:00] – The moment that launched Brett’s obsession with beating capital gains taxes[00:04:07] – Why “chasing 1031s” is making investors poor (and what to do first instead)[00:07:45] – The “no-shoes, no-shirt, no problem” blueprint for replacing active headaches with true passive income[00:09:19] – The killer move: How to actually “sell high, buy low” (and why 1031 jail kills your returns)[00:12:39] – When you must set up your DST (miss this window and the tax man wins)[00:15:31] – The shocking truth about 1031 “boot,” negotiation power, and not overpaying[00:21:45] – Passive income math: The exact steps to multiplying your cash flow (with no toilets, trash, or termites)[00:29:44] – How to reinvest, defer, and build wealth—without the dreaded time crunchAbout the GuestBrett Swarts is the founder and lead trustee at Capital Gains Tax Solutions. A nationally recognized expert in capital gains tax deferral strategies, Brett Swarts specializes in helping high net worth investors unlock growth, time freedom, and generational wealth through Deferred Sales Trusts. His practical approach has made him a trusted advisor to real estate entrepreneurs, business sellers, and anyone ready to escape the tax treadmill for truly passive income.🔗 LinkedIn | WebsiteResources MentionedBuilding a Capital Gains Tax Exit Plan (book by Brett Swarts)Build it to Billions and Give More (podcast by Brett Swarts)Cash Flow Quadrant (concept from Rich Dad Poor Dad)Marcus & MillichapPoint Loma Nazarene UniversityWilliam Jessup UniversityImportant 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.

Are you scared of losing tens of thousands to the IRS on your next property sale? Wondering if a 1031 exchange is really the secret weapon for building unstoppable cash flow… or just a headache waiting to happen?This episode, Kenny Bedwell, no-fluff educator and the data-driven mind behind STR Insights, breaks down exactly how to prepare for a 1031 exchange the right way—using numbers, timelines, and real investor mistakes. From crushing the fear of tax bills to unlocking hidden strategies for short-term rental success, Kenny’s frank approach is full of hard truths and simple steps.Listen now to sidestep costly errors, dodge timeline traps, and discover insider tactics you won’t hear anywhere else. Miss this episode, and you risk making one of the most expensive mistakes in real estate. Tune in while the stakes are high and every dollar counts!Timestamped Highlights[00:00] The hidden 1031 pitfalls that even experienced investors miss[00:01:14] Why “waiting until closing” could wreck your 1031 dreams[00:02:12] The shocking impact of capital gains—the numbers that matter now[00:03:16] How to use the IRS rules to your advantage (and avoid a nightmare)[00:05:13] The #1 reason most investors lose money on STR furnishings[00:07:37] The uncommon truth about 1031 down payments and boot traps[00:11:03] Kenny’s proven equity audit method: Should you sell or wait?[00:14:04] Mapping your cash flow and equity for a powerful portfolio move[00:16:50] When you should start hunting for your next market (spoiler: it’s not what you think)[00:20:46] The 60-day strategy no one is teaching for stress-free 1031 shopping[00:22:03] The risky world of reverse 1031 exchanges—what you must knowMentioned ResourcesSTR Scale Summit (event)STR Insights softwareIRS Section 1031 (1031 exchange rules)QI / 1031 Intermediary servicesReturn on Equity (ROE) auditImportant 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.

Are you terrified of sinking your cash into a dying market or worse, following the herd off a financial cliff? In this masterclass episode, Kenny Bedwell rips the lid off his 2026 Top STR Markets Report, arming you with the real numbers, raw pitfalls, and hidden opportunities no one else will dare mention.You’ll hear the unbiased, hard-hitting truth: where data says to buy, where strict regulations ruin even the prettiest towns, and razor-sharp strategies to squeeze maximum ROI in a landscape rocked by new rules and unpredictability. Kenny reveals not only the top 10 investable markets, but exactly why they’re worth your attention (and why some previous darlings are falling off).Do not wait. Miss this, and you’re risking real money, real time, and watching your freedom slip away, while others secure the deals that change their financial destiny. This episode gives you numbers, biases called out, and actionable steps you won’t get anywhere else.Timestamped Highlights[00:01] – Why most “top STR market” lists are wrong (and what everyone’s missing)[00:10] – The wild, thrilling impact of new regulations and market shakeups—this year’s biggest surprises revealed[00:23] – Kenny’s ultra-candid red light, green light analysis: Where you really should be scared (and where to pounce)[00:46] – The shocking climb of Mohican State Park and the overlooked cash cows in rural regions[01:13] – Dirty little secrets behind high-grossing mountain and lake towns (and why access and permits matter more than hype)[01:38] – Are you sitting on cash? Kenny reveals the uncommon ways budget transforms your deal-finding lens (with 4 ROI-driven categories)[01:57] – How to beat city restrictions with region plays and advanced location hunting—no more bureaucratic land mines[02:15] – The final, blunt warning: What happens if you listen to influencers over the data... and why you can’t skip this downloadMentioned ResourcesSTR Scale Summit (event)Airdna (STR market data)BiggerPocketsInterview reference: "Part 2: How to make over $500k on one STR with Jeff Usner” episode, August/September 2024Important 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.