Cash Flow Positive

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 navigate evolving tax laws while building a resilient investment portfolio. Whether you're investing in short-term rentals, midterm stays, or traditional long-term properties, this conversation is packed with insights to help you make smarter financial moves.<...

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. 

Becky explains how she balances aesthetics with function to attract better guests, command higher nightly rates, and reduce property issues. From managing remodels to optimiz...

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 in holding fees and lost revenue, and walks listeners through how to avoid making the same mistake.

Kenny breaks down the real financial impact of slow timelines, how to vet de...

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 Merit Harris.

In this episode of the Cash Flow Positive podcast, Kenny Bedwell welcomes Merit, founder of Merit Badge Property Management, to dive into the business of creating standout STRs through interactive amenities, ROI-driven design, and a deep understanding of what guests actually want. From his no-nonsense approach to systems and team leadership to the design decisions that impact bookings, Merit shares a wealth...

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—without breaking the bank.

Whether you’re furnishing a new property...

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 they compare to short-term rentals (STRs), and how to adapt your investment strategy for long-term success.

They...

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 investment choice based on your goals.

Whether you’re just getting started or looking to scale to c...

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-scenes look at what actually happens after launch day, including the unexpect...

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 launching—or even planning to launch—an STR, this episode is your financial wake-up call.

If you've enjoyed this epis...

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 wealth through real estate financing—and as someone who doesn’t shy away...

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 dynamics, and interest rates fluctuate. This episode provides a grounded perspective on when and why to make a move, an...

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 for more strategic, long-term investment thinking. This episode is a deep dive into shifting your m...

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 put your entire business at risk.

Katie explains the difference between de...

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 just about legal definitions—it’s about prevention, st...

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 converts, and shares his strategies for guest vetting, trust-building, and long-term nurt...

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 think in terms of guest journeys, content marketing, and simple tac...

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 high and low seasons, why most hosts underestimate the power of good photography, and what it really means to “...

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 night stays are a hidden lever, how to adju...

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 strategies that helped him go from a projected $30K loss to bre...

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 rushing to sell, and the most common (and fixabl...

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 books out months in advance.

Ashley reveals the challenges of designi...

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 experiences that guests will remember—and rebook.

Drawing inspiration from the world’s most unique Airbnbs...

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 advice, practical examples, and key lending insights that every investor needs to hear.

If you've e...

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 no-nonsense breakdown of gray areas in real estate, this episode will help you stay compliant, protect...

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 habits to the implications of bonu...

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 understanding when it makes sense to consider charging order protection entities, umbrella policies, or trusts.

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 matters, and how you can avoid the stress and financ...

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 good enough.

Drawing from his own projects, Kenny breaks down what many investors...

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 into a complete nightmare, with miscommunications, missed deadlines, and a designer who ghosted him in the middle of the process. The other? A more...

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 over 30 properties in some of the most stable STR markets available: military towns.

...

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 Trail in Kentucky—Kenny shares the realities of launching an STR outside the usual hotspots. He explains why vacation rental markets aren’t the on...

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, multi-unit properties, and now a boutique motel. He reveals the keys to finding great deals, structuring partnerships, and navigating the ch...

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 the “perfect” opportunity. He also discusses why defining what scaling means to you is crucial before making your next investment decision. 

A...

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 before Airbnb and Vrbo even existed, learning firsthand how smart pricing, marketing, and amenities ca...

Which amenities actually increase revenue in short-term rentals—and which ones are just a waste of money? In this solo episode of Cash Flow Positive, Kenny Bedwell breaks down the three types of amenities that move the needle: those that increase occupancy, boost ADR (average daily rate), or improve guest experience.

Kenny shares real data and case studies on what amenities truly impact bookings and pricing, revealing the biggest mistakes hosts make when choosing upgrades. He also explains how to market amenities effectively, why seasonal amenities can be a game-changer, and how five-star reviews directly impact revenue.

What’s the key to long-term success in real estate investing? It’s not just about strategy—it’s about the people you surround yourself with. In this episode of Cash Flow Positive, Kenny welcomes Tanya Rooney, a seasoned investor and short-term rental expert, to dive into the power of community, accountability, and networking in building a thriving business.

With 17+ years in real estate, Tanya has built a successful career in commercial real estate, flipping, and STR investing—but she credits her biggest wins to the relationships she’s built along the way. She reveals how masterminds, accountabili...

What’s the real secret to long-term success in real estate investing? It’s not just about the numbers—it’s about understanding your progress, defining success, and fueling momentum for the next step. In this solo episode of Cash Flow Positive, Kenny Bedwell shares his personal secret weapon for success, reflecting on how far he’s come and why taking time to acknowledge wins is essential for continued growth.

Kennt discusses how mindset, gratitude, and self-reflection play a huge role in building and scaling a real estate portfolio. He also reveals his latest big investment move—a $1.5M bout...

Buying out-of-state rental properties can feel like a gamble—so how do you ensure success and avoid costly mistakes? In this episode of Cash Flow Positive, Kenny Bedwell is joined by Jeana Deninger, an experienced short-term rental investor and consultant. With properties in Maine, Florida, and beyond, Jeana has mastered the art of managing STRs from a distance, ensuring they remain profitable while maintaining high guest satisfaction.

Jeana shares the critical steps every investor should take when purchasing and managing out-of-state properties, from choosing the right markets and assembling a reliable local team to marketing effectively and op...

In this episode of the Cash Flow Positive podcast, Kenny kicks things off with exciting news: the podcast has broken into the Top 100 in iTunes' entrepreneurship category. 

You'll discover the challenges and strategies for buying real estate out-of-state; properties that aren't just a short drive away but may require a flight or two to reach. 

Kenny shares practical advice for overcoming the fear of distance and emphasizes the importance of mindset in tackling these investments. You'll learn the key steps, including building a trustworthy acquisition team, with a focus on securing experienced le...

Are creative financing deals the key to unlocking your next short-term rental, or could they lead you into financial trouble? In this episode of Cash Flow Positive, Kenny Bedwell is joined by seasoned real estate investor Brandon Thompson, who has flipped over 2,000 homes and built a diverse portfolio of short-term rentals, long-term rentals, and commercial properties over the past 21 years.

Together, they dive into the real truths behind creative financing in the STR space. Brandon shares his personal experiences with seller financing, Subject-To deals, and owner financing, shedding light on the risks investors often overlook when chasing...