Is your short-term rental just blending into the crowd? In this episode of the Cash Flow Positive podcast, Kenny Bedwell breaks down one of the most powerful (and affordable) ways to make your property stand out—micro designs. Kenny explores why the typical templated design approach fails to drive bookings and how a strategic focus on a few unique spaces can elevate your listing and boost your bottom line. You’ll learn how to approach short-term rental design from a marketing-first perspective—w...
Jul 01, 2025•29 min•Ep. 117
Is the mid-term rental strategy a hidden gem in today’s market, or are short-term rentals still king? In this insightful continuation of the MTR vs. STR conversation, host Kenny Bedwell brings back real estate investor and healthcare professional Vivian Yip to break down the realities of both strategies in today’s economic climate. Drawing from her extensive experience operating properties across multiple states, Vivian walks listeners through the nuances of running mid-term rentals (MTRs), how ...
Jun 26, 2025•45 min•Ep. 116
Are mid-term rentals really the safer bet—or are short-term rentals still the reigning champion when it comes to maximizing cash flow? In this episode, Kenny Bedwell dives into the often-debated comparison between MTRs and STRs. He breaks down the financial, operational, and strategic nuances of each model, offering a balanced look at the pros and cons. From tax savings and revenue potential to guest expectations and personal preferences, Kenny lays out a clear framework for making the right inv...
Jun 24, 2025•20 min•Ep. 115
Most new hosts waste thousands before guests ever check in—Kim Fitzpatrick is here to change that. In this episode of the Cash Flow Positive podcast, Kenney Bedwell is joined by STR expert and Launched Host founder Kim Fitzpatrick, who reveals the #1 thing she wishes she’d done before opening the doors to guests. Hint: It’s not about having Instagram-worthy decor or the perfect throw pillows. It’s about protection, durability, and saving your sanity. Kim shares a refreshingly honest behind-the-s...
Jun 19, 2025•39 min•Ep. 114
Ever feel like launching your short-term rental is like pouring money into a black hole? Before you spend a dime on furniture or tools, you need to hear this. In this episode, Kenny Bedwell breaks down five high-impact strategies to help STR operators save thousands of dollars before even opening their doors to guests. From leveraging partnerships with cleaning companies to understanding tax benefits, Kenny shares tactical, money-saving insights that many first-time hosts overlook. If you're lau...
Jun 17, 2025•18 min•Ep. 113
Rates are high, inventory is tight, and opinions are all over the place—so is now actually a good time to buy a property? In this episode, Kenny Bedwell sits down with mortgage expert Brenna Carles to cut through the confusion and answer the big question: Is it really a buyers’ market? They dive into hard truths about investing, bust common excuses, and offer no-nonsense guidance on how to make decisions based on data, not drama. Brenna shares her perspective as someone who helps investors build...
Jun 12, 2025•47 min•Ep. 112
Everyone's talking about a "buyer’s market"—but is that really what we’re seeing in short-term rental real estate right now? In this episode, Kenny Bedwell explores whether today’s environment truly favors buyers or if the opportunity is more nuanced. He breaks down current market dynamics, challenges assumptions, and reveals what it actually takes to land a great STR deal right now. He explores why short-term rentals remain a viable long-term investment, even when buyer competition, pricing dyn...
Jun 10, 2025•30 min•Ep. 111
With the short-term rental market evolving rapidly, simply following the old playbook won’t cut it anymore. In this episode of Cash Flow Positive, Kenny Bedwell breaks down what the future of STR investing really looks like—and it’s not for the faint of heart. From industry-wide professionalization to a rising demand for uniqueness, he outlines what successful hosts need to know (and do) to stay competitive. Kenny shares his insights into how STRs are becoming more commercial and why that calls ...
Jun 03, 2025•31 min•Ep. 110
How do you know your short-term rental is actually legal, and not one neighbor complaint away from a lawsuit? In today’s episode of the Cash Flow Positive podcast, Kenny Bedwell is joined by Katie Johnson, a real estate attorney and investor, to break down one of the most misunderstood legal threats in the short-term rental world: deed restrictions. Whether you're operating in Michigan or buying in Texas, these buried clauses in your title documents could override local STR-friendly zoning and p...
May 29, 2025•40 min•Ep. 109
Just because you have a permit doesn’t mean your short-term rental is actually legal. In today’s episode of the Cash Flow Positive podcast, Kenny Bedwell shares a real-life cautionary tale that every STR operator needs to hear. After working with a client who discovered a deed restriction after closing on a property, Kenny breaks down how these restrictions work, why title companies won’t protect you, and how neighbor relationships can make or break your rental’s future. But this episode isn’t j...
May 27, 2025•16 min•Ep. 108
What does it take to turn a direct booking website into a real revenue driver? In today’s episode of the Cash Flow Positive Podcast, Kenny Bedwell is joined by Gil Chan, tech founder, short-term rental host, and the creator of CraftedStays—a platform that helps STR hosts easily build customizable direct booking sites without breaking the bank. Drawing on his background in e-commerce, Gil walks through the parallels between retail and hospitality, explains how to structure a site that actually co...
May 22, 2025•42 min•Ep. 107
Should you take direct bookings—and what does it take to make them work? In today’s episode of the Cash Flow Positive podcast, Kenny Bedwell unpacks the real considerations behind building a direct booking strategy. While many hosts focus on software and site setup, Kenny zeroes in on the biggest challenge: attracting the right traffic. He explains how to create repeat business, leverage your property’s location, and build trust with potential guests—without relying on OTAs. You’ll learn how to ...
May 20, 2025•20 min•Ep. 106
Are you pricing your short-term rental based on facts—or just following what everyone else is doing? In today’s episode of the Cash Flow Positive podcast, Kenny Bedwell sits down with Jake Cohen, founder of Step By Step BNB and a seasoned revenue manager overseeing 300+ listings. Together, they unpack the real strategies behind sustainable revenue, debunking myths and simplifying key concepts like RevPAR, booking windows, and market dynamics. Jake breaks down the difference between pricing for h...
May 15, 2025•43 min•Ep. 105
What if the real problem with your revenue isn’t your price—it’s your mindset? In today’s episode of the Cash Flow Positive podcast, Kenny Bedwell breaks down exactly why so many hosts struggle with pricing—and how to turn things around with consistent, proactive revenue management. From hiring a revenue manager to leveraging tools like PriceLabs, Kenny shares what works, what doesn’t, and why “just dropping your price” is the fastest way to lose control of your numbers. You’ll hear why minimum ...
May 13, 2025•21 min•Ep. 104
What do you do when you buy a short-term rental, and it just doesn’t perform? In today’s episode of the Cash Flow Positive Podcast, Kenny Bedwell welcomes Erik Courson, an STR investor, tech enthusiast, and data-driven host, to share the honest story of how he bought a property at the peak of the market—and what he did when it started bleeding cash. In this open, numbers-first conversation, Erik walks us through the decisions that led to the purchase, the surprises he encountered, and the strate...
May 09, 2025•39 min•Ep. 103
What do you do when a property isn’t performing—and how do you know if it’s time to cut your losses or hold tight and turn it around? In today’s episode of the Cash Flow Positive Podcast, Kenny Bedwell offers a grounded, practical perspective on one of the toughest situations a real estate investor can face: owning a short-term rental that just isn’t working. Drawing from real-world examples and lessons learned from clients across the U.S., Kenny walks through the key questions to ask before rus...
May 07, 2025•20 min•Ep. 102
What happens when you take a massive design risk on a short-term rental—and it turns into your most profitable investment ever? In today’s episode of the Cash Flow Positive podcast, Kenny Bedwell welcomes Ashley Guy, a short-term rental investor, mom of six, agent, coach, and creative powerhouse behind one of the most unique Airbnbs in the U.S. Ashley shares the full story behind her now-famous “kink cabin” in Gatlinburg, Tennessee—a bold, adult-themed STR that grosses six figures annually and b...
May 01, 2025•43 min•Ep. 101
What makes a short-term rental not just good, but unforgettable—and why do the most unique properties often deliver the biggest returns? In today’s episode of the Cash Flow Positive Podcast, Kenny Bedwell explores how creating wildly unique properties can lead to massive success in the short-term rental market. Instead of copying cookie-cutter designs, Kenny explains why the most profitable hosts think differently: they go all in on targeting a specific guest avatar and design unforgettable expe...
Apr 29, 2025•22 min•Ep. 100
Are you navigating real estate deals without fully understanding the risks—or worse, putting yourself in legal jeopardy? In today’s episode of the Cash Flow Positive Podcast, Kenny Bedwell welcomes Parker Borofsky, an experienced investor and short-term rental lending expert, to unpack some of the hottest—and riskiest—topics in real estate today. From the realities of seller credits and subject-to deals to the right (and wrong) ways to use LLCs for property ownership, Parker shares real-world ad...
Apr 24, 2025•45 min•Ep. 99
Are you making investment moves that could unknowingly cross the line into mortgage fraud? In today’s episode of the Cash Flow Positive Podcast, Kenny Bedwell breaks down some of the hottest (and riskiest) real estate strategies being pushed today—from seller credits to subject-to deals to buying properties under LLCs. Kenny reveals what’s truly legal, what’s risky, and what could get investors into serious trouble if not handled properly. Packed with practical examples, actionable advice, and a...
Apr 23, 2025•23 min•Ep. 98
What if global economic decisions could reshape the future of your short-term rental investments? In this solo episode of the Cash Flow Positive podcast, Kenny Bedwell dives deep into the ripple effects of tariffs, presidential policies, and tax changes—and how they’re likely to impact STR markets across the U.S. Drawing on his economics background and personal real estate experience, Kenny breaks down the macroeconomic trends in simple, real-world terms. From potential shifts in consumer travel...
Apr 16, 2025•39 min•Ep. 97
What happens when your Airbnb guest sues you—and are you actually protected? In this episode of Cash Flow Positive podcast, Kenny Bedwell invites tax attorney and strategic advisor Anthony Brister to share crucial insights into asset protection, estate planning, and insurance—especially for short-term rental (STR) investors. Anthony, founder of the Brister Law Firm, breaks down the levels of legal and financial protection STR operators should consider, from forming the right kind of LLC to under...
Apr 11, 2025•31 min•Ep. 96
What do you do when your Airbnb guest sues you—and the case drags on for years? In this solo episode of Cash Flow Positive, Kenny Bedwell shares the behind-the-scenes story of a lawsuit that caught him off guard, how he navigated the legal chaos, and the surprising truth about LLC protection and short-term rental insurance. This isn’t just a cautionary tale—it’s a wake-up call for every real estate investor who thinks they’re safe behind an LLC. Kenny breaks down exactly what happened, why it ma...
Apr 10, 2025•16 min•Ep. 95
Are you truly ready to launch your next short-term rental—or are you overlooking the hidden costs that could derail your returns? In this episode of Cash Flow Positive, Kenny Bedwell continues the conversation on hard-earned lessons from the field, offering raw and practical advice every STR investor should hear. This isn’t just theory—it’s a behind-the-scenes look at what really happens when properties take longer to launch, when holding costs spiral, and when “almost guest-ready” just isn’t go...
Apr 03, 2025•34 min•Ep. 94
What does it really take to launch a short-term rental successfully—when things don’t go as planned? In this solo episode of Cash Flow Positive, Kenny Bedwell pulls back the curtain on two recent STR setup experiences that tested his patience, budget, and systems. Kenneth shares everything he learned while launching properties in Asheville and Kentucky, including working with designers, managing contractors, and navigating delays, disasters, and unexpected design decisions. One project turned in...
Apr 01, 2025•20 min•Ep. 93
What if you could invest in STRs where demand never dries up—without competing in oversaturated vacation markets? In this episode of Cash Flow Positive, Kenny Bedwell sits down with Maria Reith, an experienced STR investor who has built a thriving rental portfolio in military towns, including Dayton, Ohio, and San Antonio, Texas. Maria didn’t start with a background in real estate—she began investing as a way to prepare for retirement. But what started as a simple strategy quickly scaled into ov...
Mar 27, 2025•38 min•Ep. 92
What if you could invest in short-term rentals without competing in oversaturated vacation markets? In this episode of Cash Flow Positive, host Kenny Bedwell challenges the idea that STR success is only found in traditional vacation destinations. Instead, he explores alternative STR markets that offer consistent demand, fewer competitors, and strong cash flow opportunities. Drawing from his own experience setting up two STR properties—a 5-bedroom renovation project and a rental on the Bourbon Tr...
Mar 25, 2025•18 min•Ep. 91
How do you scale from a single short-term rental to managing over 30 properties and owning a boutique hotel? In this episode, Kenny is joined by Tony Stancato, Founder of Book N' Gather Property Management. He shares how he leveraged partnerships, operational expertise, and a strategic mindset to build a thriving STR business in Southwest Michigan. Tony walks us through his journey—from buying his first vacation rental in 2021 to managing a diverse portfolio that includes single-family homes, mu...
Mar 20, 2025•41 min•Ep. 90
Scaling a real estate portfolio isn’t just about buying more properties—it’s about strategic growth, partnerships, and mindset shifts. In this solo episode of Cash Flow Positive, Kenny Bedwell shares his personal journey of scaling his short-term rental business, highlighting the biggest challenges, lessons, and strategies that helped him go from his first investment to a sustainable, cash-flowing portfolio. Kenny emphasizes the importance of starting small, taking action, and not waiting for th...
Mar 18, 2025•21 min•Ep. 89
What if you could increase bookings and nightly rates just by adding the right amenities? In this episode of Cash Flow Positive, Kenny Bedwell is joined by short-term rental expert Jose Cornejo to break down the real impact of STR amenities—and how to choose the ones that actually move the needle. With 18+ years of experience in the STR industry, Jose has built and managed lakefront homes in the Poconos, beachfront rentals in the Outer Banks, and additional properties in Kentucky. He started bef...
Mar 13, 2025•32 min•Ep. 88
