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PODCAST

Cash Flow Positive

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

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All Episodes

41:11

Part 2: Emile Sakhel - How Airbnb's Fee Change...

Cash Flow Positive ·

2026/03/26

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

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21:20

Part 1: How Airbnb's Fee Change Impact Hosts

Cash Flow Positive ·

2026/03/25

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

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24:13

The Opportunity Cost of Buying Today

Cash Flow Positive ·

2026/03/19

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

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23:31

Recap of the STR Scale Summit

Cash Flow Positive ·

2026/03/12

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

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44:23

Part 2 - Stacey St. John - The “Toilet Test” Every...

Cash Flow Positive ·

2026/03/05

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,

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19:29

Part 1: Easy hack to bump revenue by 15%

Cash Flow Positive ·

2026/03/03

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

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32:04

How to make money on the buy

Cash Flow Positive ·

2026/02/24

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

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40:46

Part 2: Current State of the Industry

Cash Flow Positive ·

2026/02/12

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

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24:00

Part 1: Current State of the Industry

Cash Flow Positive ·

2026/02/10

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

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40:30

Sarah Karakaian and Annette Grant | Turn Your...

Cash Flow Positive ·

2026/02/05

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

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32:12

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

Cash Flow Positive ·

2026/01/27

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

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41:41

Part 2: Brett Swarts - Preparing For A 1031 Exchange...

Cash Flow Positive ·

2026/01/15

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

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26:30

Part 1: Preparing For A 1031 Exchange The Right Way

Cash Flow Positive ·

2026/01/13

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

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37:09

Top STR Markets for 2026

Cash Flow Positive ·

2025/12/30

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

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30:58

2026 Predictions and 2025 Market Recap

Cash Flow Positive ·

2025/12/18

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

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42:18

Part 2: The #1 strategy to increasing occupancy

Cash Flow Positive ·

2025/12/11

Are you feeling stuck with underwhelming bookings, even with a great short-term rental? Wondering how savvy investors transform high-mortgage properties into unstoppable cash flow machines without risky over-investment or luck?In this bold, results-focused episode, Kenny Bedwell sits down with data-driven real estate strategist Jess Broyles, who reveals the real-world playbook that turned ordinary homes into 6-figure yielders.Get ready for an unfiltered breakdown of advanced multi-listing tactics,

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24:26

Part 1: The #1 strategy to increasing occupancy

Cash Flow Positive ·

2025/12/09

Who says you have to settle for empty nights and slow seasons in your short-term rental business?Today, Kenny Bedwell, the data-driven founder of SCR Insights and host of Cashflow Positive, uncovers the single most overlooked tactic for filling your calendar year-round. Whether you’re brand new or a seasoned investor tired of watching rival listings rack up bookings, you’re about to learn how to outsmart the algorithm, target untapped guest avatars, and supercharge your occupancy without slashing

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42:29

Part 2: Tips for working with out of state contractors

Cash Flow Positive ·

2025/12/04

Hiring contractors is hard enough… hiring them out of state can feel terrifying.In this value-packed episode of Cashflow Positive, Kenny sits down with Jen Josey, real estate investor, coach, mastermind leader, and construction expert, to break down exactly how to find, vet, manage, and protect yourself when working with contractors in markets where you don’t live.Jen shares the six critical documents every investor should use, the insider process for finding investor-friendly contractors (hint:

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25:18

Part 1: Tips for working with out of state contractors

Cash Flow Positive ·

2025/12/02

Ever felt blindsided by skyrocketing costs and endless delays when renovating a property out of state? You are not alone, and you do not have to fall victim to contractor nightmares again.In this no-fluff solo episode, Kenny Bedwell (the relentless numbers-driven voice behind Cash Flow Positive) drops a real talk blueprint for working with out-of-state contractors on STR investments, so you keep your profits high and your headaches low. Pulling from raw experience and data-backed practical steps, he

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26:10

How Far Can $200K Really Go?

Cash Flow Positive ·

2025/11/25

$200,000 used to feel like a powerhouse investing budget… but in today’s short-term rental landscape, it doesn’t go nearly as far as it used to.In this solo episode, Kenny Bedwell breaks down the hard truth: $200K is the new $100K.Competitive STR markets have leveled up, amenities have escalated, and investor expectations have shifted. Kenny walks through why $200K no longer guarantees entry into the big-boy markets (Smokies, Bradenton, Asheville, Bourbon Trail), what buyers consistently

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165 results

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