Cash Flow Positive

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.If you’re thinking about investing in amenities to stand out in a crowded market, this episode will help you make the smartest decisions to maximize profits.In This Episode You'll Learn:The three types of amenities: occupancy boosters, ADR boosters, and guest experience enhancersWhy not all amenities increase revenue—and how to identify the ones that doThe impact of seasonal amenities and when they actually generate bookingsHow to market your amenities properly to get the most value out of themWhy five-star reviews are worth $189 each—and how to get more of themHow small guest experience improvements can significantly impact long-term revenueAnd much more…Resources:Connect with Kenny on LinkedInFollow Kenny on InstagramEpisode Mentioned:Part 2: How to buy deals out-of-state with Jeana Deninger

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, accountability groups, and surrounding yourself with the right people can accelerate success, plus the hard lessons she learned from a motel deal gone wrong.Whether you’re just starting out or scaling your investments, this episode will give you actionable insights on leveraging relationships to build wealth faster. If you've enjoyed this episode of the Cash Flow Positive podcast, be sure to leave a review and subscribe today!Enjoy!In This Episode You'll Learn:Why accountability groups are a game-changer for real estate investorHow surrounding yourself with the right people accelerates successThe importance of celebrating wins instead of always chasing the next goalHow networking in mastermind groups can save you from costly mistakesThe key differences between STRs and boutique hotels—and why it mattersHow effective communication can prevent revenue loss in STRsAnd much more…Resources:Connect with Kenny on LinkedInFollow Kenny on InstagramTribe Builders PodcastConnect with Tanya on LinkedIn

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 boutique hotel—and how shifting his perspective helped him take on challenges he never imagined a year ago.If you’re looking for more than just investment strategies and want to build a mindset that drives success, this episode will help you reframe how you measure progress, set goals, and push past your limits.In This Episode You'll Learn:Why success isn’t just about hitting big milestones—it’s about progressThe power of gratitude and self-reflection in business growthHow defining your “why” helps guide smart real estate decisionsWhy tracking your achievements fuels momentum for bigger opportunitiesHow surrounding yourself with the right people accelerates successKenny’s personal experience with scaling investments and taking on new risksAnd much more…Resources:Connect with Kenny on LinkedInFollow Kenny on Instagram

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 optimizing guest experiences. She also discusses common mistakes investors make and the red flags to watch for when working with property managers, cleaners, and maintenance teams.If you’re thinking about expanding your real estate portfolio into new markets, this episode is packed with insider strategies to help you buy, manage, and scale STR properties like a pro. Enjoy! In This Episode You'll Learn:Why hiring the right professionals can make or break your STR businessThe importance of researching local markets and guest expectationsHow to properly vet and manage cleaners, handymen, and house managersThe top mistakes investors make when buying properties sight unseenHow to market your STR to stand out and maximize bookingsWhy you should never skip inspections—and how they can save you thousandsThe smart way to budget for amenities that increase guest satisfaction and ROIAnd much more…Resources:Connect with Kenny on LinkedInFollow Kenny on InstagramSavvyBreezy.com Connect with Jeana on LinkedIn

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 lenders and realtors who are well-versed in short-term rental markets.Whether you're a seasoned investor or just considering your first long-distance deal, this episode lays the groundwork for growing your real estate empire beyond your local market.If you've enjoyed this episode of the Cash Flow Positive podcast, be sure to leave a review and subscribe today!Enjoy!In This Episode You'll Learn:The importance of overcoming the fear and limiting mindset associated with buying out-of-state.Why you should always connect with the right acquisition team when buying out-of-state properties.The concept of Planned Unit Developments (PUDs) and the unique lending challenges they present.How having a quality control person can reduce the stress and hassle of managing out-of-state properties.And much more...Resources:Connect with Kenny on LinkedInFollow Kenny on Instagram

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 low-interest deals. He also opens up about pivoting his own portfolio after market saturation and declining returns, and why being intentional with your investments is more important than ever.If you’re weighing creative financing options or looking to scale your STR business without getting burned, this episode will arm you with practical advice from a veteran investor who’s seen it all. Enjoy!In This Episode You'll Learn:Why creative financing isn’t a “one-size-fits-all” solutionHow to structure seller financing and Subject-To deals the right wayThe hidden risks behind “no money down” dealsWhy the glory days of STR investing are over—and how to adaptHow to evaluate your return on equity and know when it’s time to pivot.The importance of finding the right market and avoiding oversaturated areasAnd much more…Resources:Connect with Kenny on LinkedInFollow Kenny on InstagramStrwealthbrokers.com SouthernCharmVacay.com Connect with Brandon on LinkedInFollow Brandon on Facebook

In this episode of the Cash Flow Positive podcast, Kenny explores unconventional strategies that can open doors for those looking to make significant moves without following the traditional path.These methods offer flexibility, allowing individuals to bypass common roadblocks while still creating valuable opportunities. However, while these approaches can be highly effective, they also come with unique risks and challenges that must be carefully navigated.  You'll learn how these strategies benefit both parties involved, offering potential advantages that aren’t typically available in standard agreements. By understanding how to structure these arrangements wisely, individuals can maximize their potential while minimizing exposure to unnecessary pitfalls. At the same time, it’s crucial to be aware of the fine print—certain decisions could lead to unexpected consequences if not handled correctly.  Whether you’re new to this approach or simply looking for ways to refine your strategy, this episode will provide valuable takeaways you won’t want to miss.If you've enjoyed this episode of the Cash Flow Positive podcast, be sure to leave a review and subscribe today!Enjoy!In This Episode You'll Learn:Creative financing for STRs, and how it allows direct negotiations with sellers, creating custom terms without the extensive paperwork required by banks.The concept of subject-to financing, where the seller assigns their mortgage to the buyer. Owner financing, a method popular with sellers who don't need immediate cash and want to avoid taxable events from selling.The risks associated with creative financing, including the potential for banks to call the loan if they discover the deed change.And much more...Resources:Connect with Kenny on LinkedInFollow Kenny on Instagram

In this episode of the Cash Flow Positive podcast, Kenny is joined by Josh Briner, owner of Vibe Short Term Rental Management.During the conversation, Kenny and Josh emphasize the importance of putting your best foot forward from the start, surrounding yourself with knowledgeable professionals, and making data-driven decisions. They highlight how working with industry experts, leveraging the right tools, and carefully crafting an experience tailored to a target audience can make all the difference.You'll learn the value of looking beyond surface-level costs and considering long-term gains. A conservative but intentional approach to investing in quality can lead to higher returns and a competitive edge. By understanding market demand and focusing on key differentiators, individuals can set themselves apart in an increasingly crowded space.This episode shows that, with a strong foundation and a willingness to adapt, even seemingly daunting landscapes can become profitable and rewarding.If you've enjoyed this episode of the Cashflow Positive podcast, be sure to leave a review and subscribe today!Enjoy!In This Episode You'll Learn:The challenges of managing properties near sports stadiums, such as the Buffalo Bills' stadium.Why Josh advises investors to focus on areas with established regulations and to work with experts who understand the local market.How small improvements, like adding a barrel sauna, can significantly increase revenue. The future of short-term rental investing in New York, taking into consideration new regulations and taxes.And much more...Resources:Connect with Kenny on LinkedInFollow Kenny on Instagram

In this episode of the Cash Flow Positive podcast, Kenny challenges a widely held belief that could be limiting opportunities for many investors. While common concerns about market conditions, regulatory landscapes, and financial implications drive decision-making, Kenny suggests you look beyond surface-level assumptions. By breaking down key data points and firsthand experiences, the episode presents a compelling case for reconsidering markets that some might instinctively overlook.  While no one-size-fits-all approach exists, Kenny's insights offer a fresh perspective on navigating potential challenges — and even turning them into advantages. For those willing to dig deeper and move past conventional wisdom, this episode presents thought-provoking ideas that could redefine the way they evaluate future investments.If you've enjoyed this episode of the Cashflow Positive podcast, be sure to leave a review and subscribe today!Enjoy!In This Episode You'll Learn:The foremost concern people have about investing in blue states: regulations.Why some red states have strict regulations themselves against short-term rentals, such as Kentucky and Georgia.Kenny's personal preferences and reasons for not investing in California despite his positive outlook on blue states.The advantages of investing in highly regulated markets, such as lower competition and better protection.And much more...Resources:Connect with Kenny on LinkedInFollow Kenny on Instagram

What happens when a great deal turns bad? In this episode of the Cash Flow Positive Podcast, Kenny Bedwell welcomes Brian Lambert, an experienced real estate investor, to break down the realities of short-term rental investing.Brian shares his journey in real estate, from flipping over 100 homes to building a successful short-term rental portfolio. He dives into the risks of over-projecting revenue, the importance of realistic expectations, and how misleading property listings can set investors up for failure. Through a real-life example, Brian explains why due diligence is critical and how knowing the market can prevent costly mistakes.This episode is a must-listen for investors looking to make smarter decisions, avoid financial pitfalls, and navigate today’s shifting short-term rental landscape.In This Episode You'll Learn:Why investor expectations vs. reality can make or break a dealHow to spot red flags in revenue projections before purchasing a propertyThe difference between buying real estate vs. buying a business in STR investingWhy knowing your market is the single most important factor in making smart investmentsThe role of patience, persistence, and calculated risk in long-term successAnd much more…Resources:Connect with Kenny on LinkedInFollow Kenny on Instagram