Cash Flow Positive

If you want to dominate your market and attract guests who keep coming back, your property needs to stand out in ways others can’t (or won’t) replicate. In this episode of the Cash Flow Positive podcast, Kenny Bedwell shares advanced strategies for turning an ordinary property into a top-performing short-term rental that crushes the competition. Kenny explains why unique property characteristics,...

What separates a property that barely breaks even from one that dominates its market? It’s not just timing, it’s strategy. In this episode of the Cash Flow Positive podcast, Kenny Bedwell shares hard-earned insights from his latest experiences in the field and on stage at the STR Wealth Conference. Drawing from real client case studies, personal portfolio wins, and lessons learned from analyzing h...

Are you thinking about selling your short-term rental but unsure how to prepare it for a profitable sale? In this episode of the Cash Flow Positive podcast, host Kenny Bedwell sits down with real estate expert and investor Madeline Blum to unpack the strategic steps needed to maximize your return when exiting a short-term rental investment. Madeline shares her insights from both the agent and inve...

Are you thinking about selling your short-term rental property, but unsure how to get top dollar for it? In this episode of the Cash Flow Positive podcast, Kenny Bedwell shares a step-by-step guide to help you prepare, list, and profit from selling your STR. You’ll learn what documents to gather, how to estimate your property’s value, what buyers are really looking for, and how to present your pro...

Can you create a top-performing short-term rental without spending a fortune on luxury amenities? In this episode of the Cash Flow Positive podcast, Kenny Bedwell sits down with Beata Lorinc to explore how smart design, thoughtful upgrades, and deep attention to detail can make your STR stand out—without breaking the bank. Beata shares her insights on how to approach STR design with both strategy...

Can you dominate your short-term rental market without investing in expensive amenities? In this solo episode of the Cash Flow Positive podcast, Kenny Bedwell breaks down how to become a top producer, even without the flashy features competitors might rely on. Drawing from his own experience and industry data, Kenny explains why success in STR doesn’t always mean high capital investment. Instead,...

Are you making real estate investment decisions based on long-term strategy or short-term tax benefits? In this episode, Kenny Bedwell sits down with CPA and tax strategist Ryan Bakke to break down the financial and legal implications of the recent bill passage and what it means for real estate investors. From bonus depreciation strategies to qualifying for deductions, Ryan explains how to navigat...

When it comes to designing short-term rentals, Becky Jones doesn’t just think in furniture—she thinks in photos. And in today’s market, that visual-first mindset can make or break your ROI. In this episode of the Cash Flow Positive podcast, Kenny Bedwell sits down with design expert and STR consultant Becky Jones to unpack how design, comfort, and guest experience all connect to your bottom line....

Think interior design is just about picking pretty furniture? Think again—your return on investment might depend on it. In this solo episode of Cash Flow Positive, Kenny Bedwell reveals why the speed of your short-term rental launch is one of the most critical—and commonly overlooked—factors in maximizing profit. He shares a personal story of how delays during the design process cost him thousands...

If people just wanted a place to sleep, they’d book a hotel. But in today’s competitive short-term rental market, it’s experiences that drive revenue, and no one knows that better than Merritt Haris. In this episode of the Cash Flow Positive podcast, Kenny Bedwell welcomes Merritt, founder of Merit Badge Property Management, to dive into the business of creating standout STRs through interactive a...

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 bot...

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...

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 gu...

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...

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 benef...

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 de...

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 w...

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 c...

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 i...

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...

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 thr...

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 prop...

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...

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 “ju...

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 w...