Cash Flow Positive

Kenny Bedwell
  • 5.0 (59)
  • 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. 3D AGO

    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 li...

    41 min

  2. 5D AGO

    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_bedwella href="https://rebrand.ly/01b56a" rel="noopener noreferrer"...

    24 min

  3. 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...

    41 min

  4. 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

  5. JAN 15

    Part 2: Brett Swarts - Preparing For A 1031 Exchange The Right Way

    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 crunch About 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 | Website Resources 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 Universityli...

    42 min

  6. JAN 13

    Part 1: Preparing For A 1031 Exchange The Right Way

    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 know Mentioned ResourcesSTR Scale Summit (event)STR Insights softwareIRS Section 1031 (1031 exchange rules)QI / 1031 Intermediary servicesReturn on Equity (ROE) audit 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...

    27 min

  7. 12/30/2025

    Top STR Markets for 2026

    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 download Mentioned 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 2024 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 Positivespan class="ql-ui"...

    37 min

  8. 12/18/2025

    2026 Predictions and 2025 Market Recap

    Are you one tough market away from making or breaking your STR dreams? In this eye-opening solo episode, Kenny Bedwell delivers his no-BS, data-driven breakdown of 2025’s market shakeups and lays out urgent, can’t-miss predictions for 2026. With competition at a boiling point and Airbnb’s pricing bombshell still sending shockwaves, Kenny Bedwell exposes where investors keep getting crushed, and who’s quietly winning big. From wild price slashes to the “big fish or die” investor mentality, this episode is packed with the kind of ruthless honesty and hard metrics you won’t get from any hype-driven guru. Tune in now or risk fumbling the next 12 months. Discover the exclusive moves smart investors will make next, before the rest of the market catches on, and before average operators are left behind for good. Timestamped Highlights[00:00] – Why “average” properties are getting destroyed while 90th percentile performers quietly flourish [00:03:51] – The mindset shift every STR buyer must make now to avoid draining cash flow [00:06:26] – Markets you’d written off are making a shocking comeback—here’s why [00:08:17] – Explosive legal shakeups: Are STRs still real estate or something else? [00:10:33] – The Airbnb fee switch: How hosts are sabotaging themselves and tanking in search rankings [00:13:10] – The real reason your smart price hikes backfired—and how to break the algorithm instead [00:18:46] – The “turnkey trap”: Why offloading STRs is about to flood the market (and what smart buyers must do now) [00:24:33] – Surprise winners & fallen stars: The brutally honest 2026 top markets preview [00:26:31] – Kenny’s wild 2026 prediction: The coming Airbnb “pay to play” era Mentioned ResourcesSTR Scale Summit (event)Top Markets Report (via STR Insights)Airbnb LuxeAirdna (STR market data) 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.

    31 min
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5
out of 5
59 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
    157
  • Rating
    Clean
  • Copyright
    © Kenny Bedwell
  • Show Website
    Cash Flow Positive

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