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 t...
Mar 11, 2025•20 min•Ep. 87
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 he...
Mar 06, 2025•41 min•Ep. 86
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...
Mar 04, 2025•17 min•Ep. 85
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 w...
Feb 27, 2025•44 min•Ep. 84
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 k...
Feb 25, 2025•20 min•Ep. 83
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 p...
Feb 20, 2025•44 min•Ep. 82
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 bene...
Feb 18, 2025•27 min•Ep. 81
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 differe...
Feb 13, 2025•40 min•Ep. 80
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 on...
Feb 11, 2025•16 min•Ep. 79
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...
Feb 06, 2025•42 min•Ep. 78
In this episode of the Cash Flow Positive podcast, Kenny dives into a high-stakes dilemma that many investors face — one that separates those who thrive from those who barely break even. Drawing from his own experiences and observations in the market, he unpacks a trend that has captivated aspiring investors, promising lucrative returns but carrying hidden risks that often go unspoken. As he reflects on recent real estate activity, he challenges common assumptions and urges a shift in mindset th...
Feb 04, 2025•16 min•Ep. 77
What’s the smartest way to finance your next short-term rental property? In this episode of the Cash Flow Positive Podcast, Kenny sits down with Matt Stout, a seasoned broker and expert in real estate lending, to tackle the big questions around financing STR investments. With over 30 years of experience and more than 4,000 transactions, Matt shares insider knowledge on DSCR loans, builder financing, and strategies to make your numbers work—no matter the market conditions. From avoiding emotional...
Jan 30, 2025•38 min•Ep. 76
Are commercial loans the right choice for your short-term rental purchase? In this solo episode of the Cash Flow Positive Podcast, host Kenneth Bedwell breaks down the complexities of commercial lending for real estate investors. Drawing on his own experiences, Kenneth explores when commercial loans make sense, the trade-offs between commercial and conventional financing, and how to make decisions that align with your financial goals. This episode offers a deep dive into the mechanics of DSCR lo...
Jan 28, 2025•16 min•Ep. 75
In this solo episode of the Cash Flow Positive Podcast, Kenny dives into part two of The 2-Door Strategy. This strategy, introduced in part 1 by Dr. Rachel explores how achieving key milestones with just two properties can set the foundation for financial freedom, time flexibility, or reaching other personal goals. Kenny shares his own experiences, combining insights from Dr. Rachel and his journey, to highlight how tracking progress and setting attainable goals pave the way for long-term succes...
Jan 23, 2025•20 min•Ep. 74
In this episode of the Cash Flow Positive podcast, Kenny is joined by Dr. Rachel, a former medical professional. You'll discover the transformative journey of a successful professional who had reached the pinnacle of corporate success, only to realize that the conventional path wasn't aligning with her true calling. Hear about the turning point where a significant decision was made to step away from a secure, prestigious position in favor of something entirely different. It's a tale of finding c...
Jan 21, 2025•39 min•Ep. 73
In this episode of the Cash Flow Positive podcast, Kenny explores the shifting dynamics of various markets, offering insights into how they have evolved over time and what that means for those looking to make strategic decisions. You'll discover key factors like supply, competition, and the importance of understanding your audience to ensure long-term success. Learn how to think critically about your own goals and the unique characteristics of the markets you’re interested in, with an emphasis o...
Jan 16, 2025•42 min•Ep. 72
In this episode of the Cash Flow Positive podcast, Kenny flips the script on investment advice for 2025, diving into what not to do. Instead of blindly following the latest market trends or top-ten lists, Kenny explores the pitfalls of oversaturated areas and the challenges of properties that don't align with local demand. He emphasizes that the issue isn't necessarily the market itself but the competition, pricing, and suitability of properties within those areas. You'll learn about the danger ...
Jan 14, 2025•22 min•Ep. 71
In this episode of the Cash Flow Positive podcast, Kenny is joined by Michael Cline, a seasoned real estate agent with a venture capitalist background. During the conversation, Michael brings his extensive experience in the short-term rental market to the table, sharing valuable insights that promise to reshape your understanding of property investment. You'll find strategies, real-life examples, and practical advice that highlight the complexities and opportunities within the competitive market...
Dec 26, 2024•45 min•Ep. 70
In this episode of the Cash Flow Positive podcast, Kenny dives into the nuances of crafting deals in a highly competitive environment, blending strategy, negotiation, and creative thinking. You'll discover the importance of recognizing opportunities and leveraging timing to maximize outcomes, providing you with a fresh perspective on how to navigate tough decisions when faced with limited options. You'll be guided through various techniques to handle stalemates, identify leverage points, and fos...
Dec 24, 2024•27 min•Ep. 69
In this episode of the Cash Flow Positive podcast, Kenny continues with the second of a two-part episode concerning where you should be investing. Listen as Kenny lays the groundwork with an analysis of how diverse price points and property features can create lucrative potential in under-the-radar areas. You'll learn to think beyond traditional metrics, emphasizing the importance of privacy, amenities, and unique selling points that set properties apart in competitive landscapes. Throughout the...
Dec 19, 2024•41 min•Ep. 68
In this episode of the Cash Flow Positive podcast, Kenny dives deep into the art of making smart investment decisions, particularly for those eyeing the short-term rental market. You'll discover the importance of preparation and strategy, and why simply following the herd into trending markets without considering their unique financial circumstances should be avoided. With insights tailored for both novice and seasoned investors, Kenny sets the stage for understanding the foundational principles...
Dec 17, 2024•17 min•Ep. 67
In this episode of the Cash Flow Positive podcast, Kenny is joined by Rachel Gniady, STR consultant with STR Insights. During the conversation, they discuss strategic decisions in a competitive market, particularly in real estate. You'll learn how to leverage knowledge and timing when approaching a potential deal, emphasizing the importance of understanding the broader market context and maintaining a position of strength. Discover the emotional and psychological aspects of negotiation, as Kenny...
Dec 12, 2024•49 min•Ep. 66
What’s the best way to find high ROI short-term rental deals when you’re short on funds? In this solo episode of Cash Flow Positive, Kenny Bedwell shares actionable strategies to uncover lucrative STR opportunities with little to no money down. Drawing on his own experiences, Kenny discusses creative approaches to deal structuring, financing options, and how to maximize returns while minimizing upfront investment. Kenny emphasizes the importance of focusing on undervalued properties, forcing app...
Dec 10, 2024•20 min•Ep. 65
What role does consistency play in being a great neighbor in the short-term rental world? In this episode of Cash Flow Positive, Kenny Bedwell welcomes Alex Shapiro, co-founder of Can Monkey, to discuss how this innovative service simplifies one of the biggest headaches for STR owners: trash management. From keeping properties clean and communities happy to ensuring neighbors are stress-free, Alex dives into the transformative power of systems and automation for property managers. The conversati...
Dec 05, 2024•33 min•Ep. 64
What does it truly mean to be a good neighbor in the short-term rental industry? In this solo episode of Cash Flow Positive, host Kenny Bedwell explores the key principles of being a responsible and engaged STR owner. From fostering positive relationships with neighbors to actively participating in your local and online communities, Kenny shares actionable insights to help you build a sustainable and successful business. Kenny emphasizes the importance of guest vetting to minimize issues, stayin...
Dec 03, 2024•16 min•Ep. 63
How can you scale your short-term rental business while reclaiming your time? In this episode of Cash Flow Positive, host Kenneth Bedwell is joined by Stephanie Figueros, co-founder of Bravo Virtual Assistants, to discuss the game-changing role virtual assistants can play in growing your STR portfolio. Stephanie shares her incredible journey from registered nurse to STR entrepreneur and VA agency founder, highlighting the strategies that helped her build a business that frees up time and boosts ...
Nov 28, 2024•46 min•Ep. 62
What’s the biggest mistake holding short-term rental owners back from real growth? In this solo episode of Cash Flow Positive, Kenny uncovers the number one hack to scaling your STR business without burning out. The secret? Shifting your focus from simply adding more properties to building a team and system that creates true freedom. Kenny shares the strategies that helped him move from an operator mindset to a CEO approach and emphasizes why quality over quantity is the key to achieving success...
Nov 26, 2024•16 min•Ep. 61
What if the secret to success wasn’t working harder but thinking differently? In this episode of Cashflow Positive, Kenny welcomes Julie George, best known as the “Million Dollar Host,” to discuss the transformative power of adopting a CEO mindset. Julie built an $8 million short-term rental business with over 130 properties before selling it and pivoting to coaching and inspiring others. She knows firsthand how shifting from a worker’s mindset to a leader’s vision can revolutionize your busines...
Nov 21, 2024•38 min•Ep. 60
Are you running your short-term rental business, or is it running you? In this episode of Cash Flow Positive, Kenny dives deep into the crucial mindset shift every entrepreneur needs: thinking and acting like a CEO. Too often, short-term rental owners fall into the trap of creating a new job for themselves instead of building a scalable, sustainable business. Kenny shares his hard-earned insights on how to break free from this cycle and align your business with your vision for financial freedom....
Nov 19, 2024•18 min•Ep. 59
Does focusing on macro market trends really matter for short-term rental success? In this episode of Cash Flow Positive, Kenny invites Fouad Bazzi, a seasoned real estate investor, to share his journey of scaling his portfolio to over $18 million while navigating the challenges of short-term rental markets. They discuss how staying true to your goals, leveraging data, and thinking like a real estate investor first can set you apart in an increasingly competitive industry. Fouad offers actionable...
Nov 14, 2024•43 min•Ep. 58
