Cash Flow Positive

Kenny Bedwell
  • 5.0 (60)
  • ENTREPRENEURSHIP
  • UPDATED SEMIWEEKLY

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!

  1. 2D AGO

    Recap of the STR Scale Summit

    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 time Mentioned ResourcesSTR Scale SummitBoutique hotel investingWayfair Professional account managerBRRRR strategyCommercial lending – Mark Sacco506(c) and 506(b) syndication structures 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 Bedwell Cash Flow Positive is an original podcast hosted by Kenny Bedwell. Brought to you by STR Insights. Production and editing by Podcast Your Brand.

    24 min

  2. MAR 5

    Part 2 - Stacey St. John - The “Toilet Test” Every STR Owner Should Use

    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 weapon Mentioned ResourcesFemale Short-Term Rental Investors Facebook GroupCozy GetawaysBook: Live Big by Stacey St. JohnAirbnbVRBO About 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 | Instagram Important 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 Bedwell Cash Flow Positive is an original podcast hosted by Kenny Bedwell. Brought to you by STR Insights. Production and editing by Podcast Your Brand.

    44 min

  3. MAR 3

    Part 1: Easy hack to bump revenue by 15%

    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 means Mentioned ResourcesAirbnb search algorithm strategies (in-episode explanation)Watkins Glen property case studyBooking lead time analysis 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 Bedwell Cash Flow Positive is an original podcast hosted by Kenny Bedwell. Brought to you by STR Insights. Production and editing by Podcast Your Brand.

    19 min

  4. FEB 24

    How to make money on the buy

    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 2026 Mentioned ResourcesPrice Per Square FootARV (After Repair Value) CalculationLegal bedroom requirements (egress window, heating, cooling, etc.)Desk appraisal70% RuleCash flow and appreciation models 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 Bedwell Cash Flow Positive is an original podcast hosted by Kenny Bedwell. Brought to you by STR Insights. Production and editing by Podcast Your Brand.

    32 min

  5. FEB 12

    Part 2: Current State of the Industry

    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 exit Mentioned ResourcesSmarter Short Term Rentals – Facebook groupSTR Scale SummitBRRRR Strategy by David GreeneBiggerPockets About 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 | Website Important LinksWant us to find the deals for you? https://strinsights.com Get Top Markers for STRs (2025) - https://rebrand.ly/28b1df Instagram – @kenny_bedwellYouTube – Cash Flow PositiveLinkedIn – Kenneth Bedwell Cash Flow Positive is an original podcast hosted by Kenny Bedwell. Brought to you by STR Insights. Production and editing by Podcast Your Brand.

    41 min

  6. FEB 10

    Part 1: Current State of the Industry

    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 Bedwell Cash Flow Positive is an original podcast hosted by Kenny Bedwell. Brought to you by STR Insights. Production and editing by Podcast Your Brand.

    24 min

  7. FEB 5

    Sarah Karakaian and Annette Grant | Turn Your Calendar into Cash in 2026

    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 competition Mentioned 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 Grant 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 Bedwell Cash Flow Positive is an original podcast hosted by Kenny Bedwell. Brought to you by STR Insights. Production and editing by Podcast Your Brand.

    41 min

  8. JAN 27

    The Most Important Deal-finding Metric You Aren't Calculating

    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-free Mentioned 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 Bedwell Cash Flow Positive is an original podcast hosted by Kenny Bedwell. Brought to you by STR Insights. Production and editing by Podcast Your Brand.

    32 min
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5
out of 5
60 Ratings

About

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!

Information

  • Creator
    Kenny Bedwell
  • Years Active
    2024 - 2026
  • Episodes
    161
  • Rating
    Clean
  • Copyright
    © Kenny Bedwell
  • Show Website
    Cash Flow Positive

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