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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

41:41

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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35:37

Investing beyond the returns

Cash Flow Positive ·

2025/11/19

Most people get into real estate for freedom, but what happens when the money isn’t enough?In this powerful episode of Cashflow Positive, host Kenny Bedwell sits down with Caleb David, a commercial real estate broker, investor, and longtime nonprofit leader whose story goes far beyond deals, commissions, and spreadsheets.Caleb opens up about his early years growing up in a strict environment, his burnout in the nonprofit world, and the leap of faith that brought him into commercial real estate. He

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47:31

Part 2: You MUST Innovate in the STR space

Cash Flow Positive ·

2025/11/13

Innovation isn’t just about building something new; it’s about building something better.In this episode of Cash Flow Positive, host Kenny Bedwell sits down with Juliano Silva, a full-time short-term rental investor and designer who’s built a portfolio of standout “signature properties” across multiple U.S. markets. From his early beginnings renting out a spare bedroom in Minnesota to creating high-performing STRs in Florida, Juliano shares how data, creativity, and intention fuel his approach to

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22:58

Part 1 – You MUST Innovate in the STR Space

Cash Flow Positive ·

2025/11/11

If your short-term rental looks the same as it did three years ago, you’re already falling behind.In this episode of Cash Flow Positive, host Kenny Bedwell explains why innovation isn’t optional. It’s the only way to stay competitive in a rapidly evolving STR market. From hotel refresh cycles to new amenity trends, Kenny breaks down how to model what the pros do and apply it to your own properties.He shares real examples of how top operators are staying ahead, from custom pickleball-court designs

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33:18

Part 2: Scaling beyond single family homes

Cash Flow Positive ·

2025/11/06

You don’t have to stop at single-family short-term rentals. You can build the systems and businesses that help others scale, too.In this episode of Cash Flow Positive, host Kenny Bedwell sits down with Tyler Gruskiewicz, a full-time real estate investor and entrepreneur from Louisville, Kentucky. Tyler shares his journey from leaving a W2 job to building a growing portfolio of STRs, boutique hotels, and vertically integrated businesses, including a cleaning company, renovation arm, and property

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29:34

Part 1: Scaling beyond single family homes

Cash Flow Positive ·

2025/11/06

What does “scaling” really mean for you?In this episode of Cash Flow Positive, host Kenny Bedwell breaks down what it truly takes to grow beyond single-family short-term rentals and why the definition of “scaling” should be unique to every investor.Kenny walks through his personal evolution from duplex house hacking to managing multi-unit portfolios, building a co-hosting business, and partnering with investors to acquire large-scale STRs and boutique hotels.Along the way, he shares the mindset,

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31:35

Part 1: The curse of review driven real estate

Cash Flow Positive ·

2025/10/28

What if your next short-term rental deal isn’t failing because of the numbers… but because of your reviews?In this episode of Cash Flow Positive, Kenny Bedwell digs into the “curse” of review-driven real estate—how guest expectations, property condition, and first impressions can quietly make or break your returns. He breaks down the two sides of STR investing (real estate + hospitality), shares real-world examples from his own portfolio, and explains why operations and guest experience are just as

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23:01

How to get rich quick with real estate

Cash Flow Positive ·

2025/10/23

How to Get Rich Quick with Real EstateIf you’ve been chasing the next “get rich quick” shortcut in real estate… this episode is your reality check.In this episode of Cash Flow Positive, Kenny Bedwell flips the script on fast money and exposes the truth about building real wealth through real estate. He shares insights from conversations with high-level investors: Those who buy $100M hotels and still play the long game and reveals why the biggest wins come from appreciation, tax strategy, and equity

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25:30

Part 1 & 2: The deal finding strategy no one is...

Cash Flow Positive ·

2025/10/07

Most investors look at bedroom counts at face value. Kenny Bedwell doesn’t.In this episode of Cash Flow Positive, Kenny reveals a deal-finding strategy he’s seen quietly pay off in competitive short-term rental markets: targeting properties with extra square footage and converting them into higher bedroom counts. From Sedona to the Poconos, Kenny explains why “heads in beds” is the #1 revenue driver, how to legally add bedrooms to force appreciation, and why average-performing STRs will always lose

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35:33

Should you refinance your property?

Cash Flow Positive ·

2025/10/02

Is refinancing your short-term rental a smart move—or a trap that eats away your cash flow?In this episode of Cash Flow Positive, Kenny Bedwell sits down with veteran mortgage broker and STR financing expert Matt Stout. With over 32 years of lending experience and thousands of deals funded, Matt pulls back the curtain on when refinancing actually makes sense. From dropping interest rates and shifting housing trends to creative ways to redeploy “dead equity” into higher cash-flowing properties, this

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40:40

Part 2: If you had $250k to invest, where should you go?

Cash Flow Positive ·

2025/09/25

If someone handed you $250,000 in cash to invest in a short-term rental, where would you buy and what strategy would you use to make that money work?In this episode of the Cash Flow Positive Podcast, host Kenny Bedwell is joined by Erin Wegrzyn, a real estate consultant with STR Insights, to explore exactly that scenario. Together, they break down how to choose the right markets, set realistic expectations, and avoid the “amenities arms race” that eats into cash flow.Erin shares her journey from

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29:27

Part 1: If you had $250k to invest, where should you go?

Cash Flow Positive ·

2025/09/23

If $250,000 dropped into your lap today, would you actually know what to do with it?In this episode of Cash Flow Positive, Kenny Bedwell pulls back the curtain on exactly how he’d put that money to work in short-term rentals. He breaks down why your financing strategy can make or break a deal, the five cost buckets most investors forget about, and why setting your ROI goal up front is non-negotiable.You’ll hear Kenny think through real markets, from Florida beaches to Shenandoah cabins, and explain

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154 results

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