Cash Flow Positive

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,...

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 regulatio...

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 wh...

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 ordinar...

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...

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 do...

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...

$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 int...

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, h...

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...

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 properti...

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 hot...

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 partneri...

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...

How to Get Rich Quick with Real Estate If 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...

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 dr...

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 shi...

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 ex...

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-negoti...

What does Airbnb’s latest fee increase mean for your bottom line, and how should it change the way you evaluate deals? In this episode of the Cash Flow Positive Podcast, Kenny Bedwell sits down with Rachel Gniady, full-time real estate investor and STR Insights consultant, to talk about how the new 15.5% host fee is reshaping underwriting, deal selection, and long-term strategy. Rachel shares how...

Airbnb has just announced a major change to its fee structure, and for hosts, the impact could be huge. In this episode of the Cash Flow Positive podcast, Kenny Bedwell breaks down the shift from a split-fee model to a single-host fee of 15.5%. He explains what this really means for your payouts, why simply raising your rate isn’t the answer, and how the wrong pricing strategy could tank your rank...

What separates investors who land the best deals from those who watch them slip away? In this episode of the Cash Flow Positive podcast, Kenny Bedwell continues his deep dive into the reasons most people miss out on profitable real estate deals. Building on Part 1’s discussion of vision and creating a moat, Kenny highlights three more critical factors that separate average investors from top perfo...

Why do so many investors pass up incredible opportunities that are sitting right in front of them? In this episode of the Cash Flow Positive Podcast, Kenny Bedwell breaks down the number one reason most people miss out on great real estate deals: a lack of vision. Using real-world examples, including a six-bedroom Montana property overlooked by more than ten investors, Kenny illustrates how the be...

What does it really take to turn a rundown property into a high-return investment? In this episode of the Cash Flow Positive podcast, host Kenny Bedwell is joined by Kyle Powers, a top-producing agent and experienced real estate investor, to continue the discussion on the infinite return model. Kyle shares his hands-on approach to finding undervalued properties, forcing appreciation, and navigatin...

What if you could own a property that pays you back entirely and then continues to cash flow year after year, with no money left in the deal? In this episode of the Cash Flow Positive podcast, Kenny Bedwell breaks down the infinite return model and shows how real estate investors can use it to create cash flow with minimal long-term capital tied up. Kenny explains how this strategy works in both s...