Cash Flow Positive (Kenny Bedwell)
Explorez tous les épisodes de Cash Flow Positive
| Date | Titre | Durée | |
|---|---|---|---|
| 28 Nov 2024 | Part 2: The #1 Hack to Scale Your Business with Stephanie Figueros | 00:46:06 | |
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 productivity. Stephanie dives into the benefits of hiring VAs, from managing guest communications to optimizing listings, and explains how to integrate them effectively into your business. She offers practical advice on identifying the right tasks to delegate, creating efficient training processes, and empowering VAs to help you scale without sacrificing work-life balance. Whether you’re managing one property or expanding a growing portfolio, this episode is packed with actionable tips to help you elevate your STR business and achieve greater freedom. Enjoy! In This Episode You'll Learn:
Resources: Connect with Kenny on LinkedIn | |||
| 25 Mar 2025 | Part 1: Types of STR Markets No One is Talking About | 00:18:24 | |
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 only profitable options and breaks down key STR opportunities in less obvious locations, including college towns, military towns, state parks, and urban areas near hospitals. Throughout the episode, Kenny highlights how investors can leverage these markets to reduce risks, secure better returns, and manage seasonality more effectively. He also discusses exit strategies and the importance of adaptability when investing in these unique STR locations. This episode is a must-listen for anyone looking to expand their STR portfolio without getting caught in the vacation rental bubble. In This Episode You'll Learn:
Resources: Connect with Kenny on LinkedIn | |||
| 10 Oct 2024 | Part 2: Future Trends on the STR Industry with Natalie Palmer | 00:39:51 | |
In today’s episode of the Cashflow Positive podcast, Kenny returns with Part 2 of his deep dive into the Future Trends of the STR (Short-Term Rental) Industry together with Natalie Palmer. You’ll explore the evolving dynamics that are shaping the future of the STR landscape, focusing on upcoming trends that could redefine the way investors and hosts approach the market. Kenny breaks down how technological advancements, shifting traveler preferences, and regulatory changes are playing a significant role in the industry's direction. The episode highlights the importance of staying ahead of these trends and adapting to future market realities before they become mainstream. As new opportunities emerge, Kenny emphasizes the need to remain agile, while also preparing for potential challenges that could impact profitability and long-term growth. If you want to future-proof your STR investments, this episode is a must-listen. Kenny shares actionable insights on what to expect in the coming years, ensuring you stay competitive in an industry that’s constantly evolving. If you’ve enjoyed this episode of the Cashflow Positive podcast, don’t forget to subscribe and leave a review! Enjoy! In This Episode You’ll Learn: How emerging technologies are changing the STR industry and what you can do to leverage them. Why understanding upcoming regulations is crucial for long-term success in the STR space. The impact of shifting traveler demographics and preferences on STR profitability. Strategies to future-proof your STR investments in an increasingly competitive market. And much more... | |||
| 18 Feb 2025 | Part 1: Creative Financing STR's | 00:26:58 | |
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:
Resources: | |||
| 11 Apr 2025 | Part 2: My Airbnb Guest Just Sued Me with Anthony Brister | 00:31:07 | |
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. Together, Kenny and Anthony dissect real-world strategies for STR investors looking to protect their assets while growing their portfolios the smart way. They also share stories—like Kenny’s own experience of being sued by a guest—that bring home the urgency of getting your protection and paperwork in place before problems arise. If you've enjoyed this episode of the Cash Flow Positive podcast, be sure to leave a review and subscribe today! Listen now and enjoy! In This Episode You'll Learn:
Resources: Connect with Kenny on LinkedIn | |||
| 08 Aug 2024 | The biggest trap with short term rentals (Part 2) | 00:38:37 | |
Kenny sits down with Dave Menapace, a successful co-host and manager of over 30 properties in the Northeast, to discuss the challenges and strategies unique to seasonal short-term rental markets like Cape Cod and Maine. They delve into the importance of budgeting for off-seasons, the value of strategic amenities such as hot tubs, and the benefits of flexible revenue management. They also emphasize the significance of location and proactive planning in maximizing property potential and revenue. Dave shares insights from his consulting company, Launchpad Consulting, which assists homeowners in launching and managing profitable short-term rentals. | |||
| 02 May 2024 | Is My Airbnb Market Saturated? (Pt. 2) | 00:39:38 | |
Welcome to Part 2 for this weeks topic - is my Airbnb market saturated? Kenny is joined by Elizabeth Richman, a seasoned co-host and property owner, who shares her journey and strategies in making her properties stand out and become highly profitable despite high market saturation. Elizabeth provides insights into various properties she manages across the country, including a cabin in Blue Ridge, Georgia, which has achieved remarkable success by catering to specific niches such as pet-friendly accommodations and focusing on unique value propositions like providing exceptional amenities and leveraging local attractions. She covers importance of creatively marketing properties to meet their specific needs and touches on the challenges of managing properties in areas with extreme competition and how to find unique selling points to attract guests. | |||
| 04 Jul 2024 | Is it my pricing, listing, or amenities - Pricing Segment (Part 2) | 00:40:53 | |
Kenny welcomes special guest Emile Sakhel, a pricing expert from 'Pricing by Mira.' They delve into advanced pricing strategies for short-term rental properties, emphasizing the importance of proper revenue management and data analytics. Emile shares his journey from anesthesia to short-term rentals and provides actionable insights on optimizing revenue through strategic pricing. They also discuss the critical role of understanding market dynamics, setting accurate base prices, and the necessity of constant adjustments for maximized revenue. Additionally, Kenny announces the upcoming 'STR Scale Summit,' a free virtual event focused on scaling short-term rental businesses through expert knowledge and innovative strategies. | |||
| 20 Jun 2024 | Is Property Management Actually Worth It? (Pt. 2) | 00:44:48 | |
Patryk Swietek is here for Pt 2 to dive into the ultimate question - is property management actually worth it? Patryk is the founder of STR Nation and a seasoned property manager with over 100 signed properties. This conversation covers the nuances of property management, the importance of localized expertise, the challenges of scaling property management at a national level, and the significance of continuous improvement in the competitive world of short-term rentals. | |||
| 16 Jan 2025 | Part 2: Don't Invest HERE | 00:42:10 | |
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 on balancing opportunity with realistic expectations. The conversation also dives into the nuanced challenges of navigating highly competitive landscapes and the risks of targeting niche segments without adequate preparation. Kenny shares candid observations about the pressures of adapting to rising standards and maintaining a competitive edge in environments that demand significant investment. This episode offers a refreshing perspective for those at various stages of their journey. Whether you’re seasoned or just starting out, the insights shared serve as a valuable guide for making informed choices in a rapidly changing environment. 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:
Resources: | |||
| 22 Aug 2024 | How to invest in new markets (Part 2) | 00:33:46 | |
Kenny welcomes former student Jade, a physician from Southern California, who shares her journey of transitioning from long-term to short-term rentals. Jade discusses the challenges she faced, including recovering from the 2008 financial crisis, navigating a competitive market for her first two cabins in the Smokies, and her strategic move to Asheville, North Carolina. Jade emphasizes the importance of education, using data to drive investment decisions, and developing a strong market analysis process. Her story illustrates how meticulous planning and the right guidance can transform an investment portfolio and achieve financial freedom. | |||
| 26 Dec 2024 | Part 2: How To Negotiate Like A Boss with Michael Cline | 00:45:29 | |
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 of vacation rentals. Michael breaks down critical components of successful negotiations, discussing scenarios ranging from hot properties with multiple offers to those languishing on the market. He emphasizes the importance of moving quickly, leveraging relationships, and understanding the unique dynamics of short-term rental investments versus traditional home purchases. This episode is a treasure trove of knowledge for anyone interested in real estate investment, particularly in navigating the intricacies of the short-term rental market. 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:
Resources: | |||
| 12 Dec 2024 | Part 2: Finding High ROI STR Deals with No Money with Rachel Gniady | 00:49:02 | |
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 and Rachel touch on the influence of external factors such as agents' motivations and market pressure. The discussion also explores the critical role of making informed decisions from the outset and how proper preparation can lead to long-term success. This episode brings insight into how minor adjustments in approach can unlock larger opportunities and avoid costly missteps, all while maintaining a disciplined focus on the bigger picture. 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:
Resources: | |||
| 21 May 2024 | What Is Dirty Data and How Can We Avoid It? (Pt. 1) | 00:17:14 | |
This week we're getting dirty...diving into the 'dirty data' within short-term rental market analyses. I'm talking about what dirty data is, its impact, and how to spot and avoid it using practical examples from Airbnb listings and data tools. You'll hear the importance of scrutinizing property listings for anomalies in revenue, review counts, and calendar availability as indicators of reliability. I hope this helps inspire you to evaluate market and property data, in order to make informed investment decisions. | |||
| 28 May 2024 | No data? No problem! (Pt. 1) | 00:17:31 | |
No data? No problem! This week, I’m talking all about how to make informed investment decisions even when there is limited or no data available. I share my personal experiences with adding unique amenities to properties and discuss the importance of risk management for investors, especially first-timers. You’ll hear my outline for a two-step method for handling situations with sparse data, practical examples, and a secret formula for evaluating the potential revenue impact of amenities. | |||
| 14 May 2024 | How To Find Cash Flowing Deals in 45 Days? (Pt. 1) | 00:15:40 | |
Today’s episode is Part 1 of how to find cash flowing deals in 45 days! You’ll learn my five-step strategy to finding cash-flowing deals within 45 days or less, while navigating a more challenging market than previous years. I highlight the importance of understanding ROI goals, targeting the right markets, identifying market sweet spots, conducting correct property evaluations, and crafting effective offers. Stay tuned for Part 2 where you will hear from someone who has actually applied these steps and been successful! | |||
| 01 Aug 2024 | The Top STR Markets to Invest In (Part 2) | 00:38:48 | |
Kenny interviews Madeline Blum, a real estate agent and short-term rental investor with properties in various markets including the Smoky Mountains, North Carolina, Bourbon Trail, and Panama City Beach. They discuss the challenges of investing in popular and emerging markets, the importance of design and property optimization, and the unique characteristics that make certain areas appealing for short-term rental investments. Madeline shares her experiences and insights on finding and managing properties, highlighting the significance of doing thorough research, understanding market dynamics, and maintaining high standards to stand out in competitive markets. | |||
| 24 Dec 2024 | Part 1: How To Negotiate Like A Boss | 00:26:55 | |
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 foster collaboration among all parties involved. From understanding the dynamics of agreements to uncovering overlooked negotiation tools, Kenny will reveal tactics that can shift the odds in your favor, even when circumstances seem unfavorable. With practical advice and actionable tips, this episode is a masterclass in preparation and adaptability. Whether it's navigating unexpected hurdles or working with others to achieve a shared goal, the discussion is rich with takeaways for anyone eager to refine their negotiation skills. 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:
Resources: | |||
| 06 Feb 2025 | Part 2: The "Good" Deal Gone Bad with Brian Lambert | 00:42:14 | |
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:
Resources: Connect with Kenny on LinkedIn | |||
| 21 Nov 2024 | Part 2: The CEO Mindset with Julie George | 00:38:25 | |
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 business—and your life. Julie shares her journey, starting with just one property, and how she scaled her business by mastering delegation, creating systems, and empowering her team to take ownership. She explains why developing a clear vision for your dream life and prioritizing what truly matters is essential to building a scalable and sustainable business. Julie’s insights into building a business culture based on collaboration, generosity, and shared success will inspire you to rethink your approach to leadership. Whether you’re managing a single rental or a growing portfolio, this episode offers practical advice and motivation to help you achieve more freedom and fulfillment. If you enjoyed this episode, don’t keep it to yourself—share it with someone who could benefit from Julie’s insights! Be sure to follow, rate, and review Cashflow Positive for more episodes that empower short-term rental entrepreneurs. In This Episode You'll Learn:
Resources: Connect with Julie on LinkedIn Connect with Kenny on LinkedIn Julie’s Books: | |||
| 30 Jul 2024 | The Top STR Markets to Invest In (Part 1) | 00:21:47 | |
Kenny discusses the pitfalls and biases of 'Top 10' short-term rental market lists, explaining why they are often unreliable. He then provides his own list, detailing his top 10 regions to invest in for STRs in 2024 while emphasizing the importance of market-specific variables like regulations, property types, and inventory. Kenny covers pros and cons of markets including Florida's Tampa area, Taos, New Mexico, the Finger Lakes in New York, and more. He concludes by highlighting the best markets for cashflow and prepares listeners for an upcoming episode featuring an investor's experience in lesser-known markets. | |||
| 15 Oct 2024 | Part 1: How to make over $500k on one STR | 00:18:29 | |
In this episode Kenny explores how to generate over $500,000 in revenue from a single short-term rental property. He discusses the unique features and strategies used by high-earning property owners, including large properties with six or more bedrooms, unique amenities like lazy rivers and wedding venues, and the importance of space, privacy, and hospitality. He emphasizes the impact of direct bookings and repeat guests on revenue. Stay tuned for part two, where Kenny interviews one of these successful property owners. | |||
| 11 Jul 2024 | Is it my pricing, listing, or amenities? - Amenities Edition (Part 2) | 00:36:54 | |
Kenny welcomes Bryndee Barton from Revity Refined to discuss strategies for maximizing revenue in vacation rentals through effective use of amenities and design. Bryndee shares insights into her journey from flipping houses to running successful vacation rentals, such as Loma Homes, which have gone viral due to their unique themes and amenities. They delve into the importance of understanding market demands, using data to inform design decisions, and standing out visually with bold concepts. The conversation covers specific strategies for different markets, the importance of guest avatars, and practical advice for existing property owners looking to revamp their rentals. Bryndee also teases her upcoming participation in the STR Scale Summit, where she'll share more detailed insights into data-driven design and managing nationwide property projects. | |||
| 17 Oct 2024 | Part 2: How to make over $500k on one STR with Jeff Usner | 00:56:31 | |
How do you generate over $500,000 with just one short-term rental? In this episode of Cashflow Positive, Kenny sits down with Jeff Usner, CEO of STR Digital, to uncover the secrets behind his luxury short-term rental properties. Jeff has built a portfolio of STRs across Pennsylvania, including a standout property that has grossed over $500,000 in revenue this year alone. He shares the insights, strategies, and mistakes learned over his 11 years in the business, offering actionable advice for anyone looking to scale their short-term rental portfolio. Jeff emphasizes the importance of understanding your target market and designing properties that cater to specific demographics, like families. From swimming pools to home theaters, Jeff's properties deliver a luxury experience that guests return for time and time again. This episode dives deep into the high-end amenities and exceptional hospitality that have set his properties apart, and how Jeff built a brand around this model. Curious about how you can work less and make more in the STR space? Jeff shares his strategies for maximizing revenue, creating memorable guest experiences, and why automating tasks is essential for growing a sustainable and profitable business. Listen now and enjoy! Key takeaways:
Resources: | |||
| 13 Feb 2025 | Part 2: Is it worth investing in Blue states with Josh Briner | 00:39:52 | |
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:
Resources: | |||
| 19 Nov 2024 | Part 1: The CEO Mindset | 00:18:18 | |
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. From hiring the right people with a growth mindset to fostering a collaborative culture where ownership and innovation thrive, Kenny offers practical advice that’s grounded in experience. You’ll discover why empowering your team, setting up systems, and letting go of micromanagement are critical for scaling successfully. He also discusses the importance of maintaining balance and staying true to your goals, offering actionable strategies to create a business that works for you—not the other way around. Whether you're managing your first property or scaling a large portfolio, this episode will inspire you to embrace the mindset of a true leader. With Kenny’s guidance, you’ll gain the confidence to step back from day-to-day operations and focus on what really matters: strategic growth, empowering your team, and achieving your ultimate goal of financial freedom. 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:
Resources: Connect with Kenny on LinkedIn Book: Who Not How: The Formula to Achieve Bigger Goals Through Accelerating Teamwork | |||
| 09 Jul 2024 | Is it my pricing, listing, or amenities? - Amenities Edition (Part 1) | 00:28:17 | |
Kenny delves into the crucial topic of property amenities and their impact on revenue for short-term rentals. Kenny explains the importance of understanding your 'guest avatar' to make informed decisions about which amenities to add. He highlights the difference between amenities that maximize revenue (such as pools and hot tubs) and those that sustain occupancy (such as theater rooms and barrel saunas). Bedwell emphasizes the importance of effectively marketing these amenities through top-notch photography and strategic placement in your listings. He also provides practical examples and data comparisons to underline his points. This episode includes valuable insights and actionable advice aimed at helping both novice and seasoned investors enhance their property portfolios for optimal financial returns. Additionally, Kenny invites listeners to join the free upcoming STR Scale Summit for more expert advice and networking opportunities. | |||
| 14 Jan 2025 | Part 1: Don't Invest HERE | 00:21:58 | |
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 of high-maintenance investments. Disocver how overly competitive markets often push investors into unsustainable cycles of reinvestment just to keep up. From expensive amenities to aggressive marketing campaigns, Kenny reveals how these efforts can drain both time and resources without adding meaningful returns. Finally, Kenny highlights the importance of evaluating long-term expenses and avoiding "boom and bust" markets. Drawing on examples like fluctuating tax rates and insurance costs, he suggests that you factor in these variables before committing to an investment. 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:
Resources: | |||
| 30 Jan 2025 | Part 2: Should I Use a Commercial Loan for My STR Purchase with Matt Stout | 00:37:31 | |
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 decision-making to understanding the nuances of construction loans, this episode offers invaluable advice for real estate investors looking to scale their portfolios while minimizing risk and maximizing returns. 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 Will Learn:
Resources: | |||
| 27 Aug 2024 | Does ranking on Airbnb actually matter? (Part 1) | 00:18:08 | |
In this episode of Cashflow Positive, Kenny dives deep into the intricacies of Airbnb rankings. He challenges the conventional focus on ranking, emphasizing instead on marketability to naturally improve listings' performance. Kenny goes through common scenarios faced by property owners, from maintaining a listing’s position to preparing new rentals for market entry. He offers step-by-step advice on enhancing marketability, including optimizing hero images and adjusting pricing strategies. Kenny also covers the significance of minimizing fees and managing minimum night stays. Lastly, he briefly discusses the impact of using multiple platforms like VRBO and strategies for direct bookings. The episode wraps with a preview of a special guest in the next episode who will share expert tips on ranking higher on Airbnb. | |||
| 27 Jun 2024 | Ways To Scale Your STR Portfolio - Finance Addition! (Pt. 2) | 00:35:22 | |
Brian Bockholdt, joins for this week’s part 2 episode on ways we can scale our STRs - finance addition! Brian, with 30 years of mortgage experience and 5 years as an STR investor, shares valuable insights about various loan products, including second home loans and investment property loans. He clears up misconceptions about second home loans and highlights the benefits of using them to minimize down payments and secure better lending terms. You’ll also hear about the nuances of debt-to-income ratios, refinancing options, adjustable-rate mortgages, and the importance of working with specialized lenders. Give Brian a call: (630)-210-4205 Connect with Brian on LinkedIn | |||
| 25 Jul 2024 | Your biggest mistake when you scale (Part 2) | 00:44:43 | |
Kenny talks with Margot, the CEO and co-founder of Hostfully, a leading property management software company. Kenny discusses his journey from replacing his W2 income with short-term rental cash flow to helping others achieve the same success. Margot delves into how Hostfully assists property managers, particularly smaller-scale and novice hosts, with features like digital guidebooks, booking platform integration, and dynamic pricing. They also explore how automation can manage cleaning schedules, guest communication, and upselling opportunities to optimize both revenue and guest satisfaction. Margot emphasizes the importance of planning and leveraging technology from the outset to ensure smooth scaling and effective management of rental properties. They also touch on the role of AI in property management and how it can enhance customer support and guest experiences. | |||
| 30 May 2024 | No data? No problem! (Pt. 2) | 00:41:38 | |
Please welcome special guest and seasoned real estate broker, Matthew McCall-Stillman, for this Part 2 episode! Matt shares his journey from long-term rentals to owning and managing a diverse portfolio of 51 properties, including a mix of short, mid, and long-term rentals. He highlights a case study of a successful property in Cadillac, Michigan, and outlines creative strategies for assessing market potential without relying heavily on traditional data sources. Throughout this conversation, you'll also hear about the significance of starting small for new investors, practical advice on maximizing cash flow, and the value of partnering with experienced mentors in the STR space. Connect with Kenny on LinkedIn! | |||
| 09 Oct 2024 | Part 1: Future Trends of the STR Industry | 00:20:41 | |
In today's episode of the Cashflow Positive podcast, Kenny dives into the intricacies of strategic growth and market adaptation. You'll discover the importance of recognizing how expansion in any sector can impact both supply and demand. The episode touches on how certain decisions may seem beneficial on the surface but could create unintended consequences for those entering specific markets too aggressively. Learn how some regions are experiencing significant shifts, with new developments pushing competition to new heights. As the landscape becomes more saturated, Kenny emphasizes the need for unique approaches that stand out and maintain relevance over time. The episode shows how staying competitive means not only adjusting strategies but also embracing a mindset of continuous improvement in an evolving, maturing industry. 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:
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| 23 Jan 2025 | Part 2: The 2-Door Strategy | 00:20:25 | |
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 success. From understanding the financial mechanics of short-term rentals to learning how to build momentum through small, consistent wins, this episode is packed with actionable advice for anyone looking to make their mark in real estate investing. Whether you’re starting out or scaling up, this episode offers practical tools to help you define and achieve your version of success. 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:
Resources: Connect with Kenny on LinkedIn | |||
| 06 Jun 2024 | Is It Too Late To Invest In Short-Term Rentals? (Pt. 2) | 00:35:04 | |
Welcome to Part 2 of this weeks topic - is it too late to invest in STRs? Brenna Carls, CEO and founder of The Mortgage Shop, joins to discuss this, talking about the current high-interest rate environment, how investors can still cashflow, and the importance of understanding loan types like DSCR. Brenna provides valuable tips on performing pro forma calculations, the significance of amenities, cost segregation for tax benefits, and navigating different loan options. | |||
| 20 Aug 2024 | How to invest in new markets (Part 1) | 00:17:19 | |
In this episode of Cashflow Positive, Kenny explores the challenges and strategies for investing in new short-term rental markets. Kenny discusses the importance of both data and emotional confidence when deciding to invest in unfamiliar markets. He emphasizes that understanding why people visit the market, housing price trends, and potential long-term appreciation are crucial. Kenny also addresses common fears, such as hiring new teams and finding reliable cleaners, and provides insights on overcoming them. This episode aims to help investors recognize their comfort levels and make informed decisions about diversifying their property portfolios. | |||
| 25 Jun 2024 | Ways To Scale Your STR Portfolio - Finance Addition! (Pt. 1) | 00:16:32 | |
This week, we are focusing on ways to scale your STR portfolio…finance addition! You’ll hear how to effectively scale your short-term rental portfolio through a variety of financing options, and key concepts like leveraging debt to income ratio (DTI), speaking with multiple lenders, and using other people's money to maximize growth. Stay tuned for part 2 on Thursday! | |||
| 11 Mar 2025 | Part 1: Amenities That Change the Game | 00:20:13 | |
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:
Resources: Connect with Kenny on LinkedIn Episode Mentioned: Part 2: How to buy deals out-of-state with Jeana Deninger | |||
| 29 Aug 2024 | Does ranking on Airbnb actually matter? (Part 2) | 00:53:41 | |
Kenny interviews Jeff Brown, founder of IntelliHost, in an episode focused on leveraging data to optimize short-term rental (STR) listings on Airbnb. Jeff shares his journey from investing in vacation rentals to creating IntelliHost, a platform designed to help properties rank higher and convert better. They discuss key metrics like impressions, first page impressions, click rates, and booking conversion rates, emphasizing data-driven strategies to improve property performance. The conversation also touches on common mistakes hosts make, practical tips for improving listing visibility, and the impact of small changes on overall success. The importance of buying the right property and the feasibility of investing in competitive markets are also explored. | |||
| 01 Apr 2025 | Part 1: Recent Hard Lessons Learned | 00:19:57 | |
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 streamlined—but still challenging—process that highlighted the value of clear communication, strong referrals, and aligned teams. If you’ve ever thought about hiring a designer or project manager to help launch an STR—or wondered what pitfalls to avoid—this episode delivers a firsthand look at what not to do and what you can do instead to protect your investment and timeline. If you've enjoyed this episode of the Cash Flow Positive podcast, be sure to leave a review and subscribe today! Listen now and enjoy! In This Episode You'll Learn:
Resources: | |||
| 06 Aug 2024 | The biggest trap with short term rentals (Part 1) | 00:20:23 | |
Kenny identifies the biggest trap for short-term rental hosts: not tracking future earnings and pacing. Kenny explains how hosts often get caught up in the high season's success and fail to prepare for the fall and shoulder seasons. He discusses how understanding key KPI metrics and being proactive, rather than reactionary, can help hosts maintain profitability. Kenny emphasizes the importance of data analytics, including understanding past trends, adjusting pricing strategies, and leveraging amenities in changing seasons. The episode also teases a future discussion with a professional co-host managing over 30 properties, who will share strategies for handling seasonality in highly seasonal markets. | |||
| 16 May 2024 | How To Find Cash Flowing Deals in 45 Days? (Pt. 2) | 00:32:06 | |
In this Part 2 episode, Sheila Hrinda from STR Insights is joining to discuss strategies for finding cashflow positive real estate deals within 45 days. Sheila shares her journey from a cost accountant in the construction industry to a full-time real estate investor since 2012. She shares her approach to buying short-term rentals from the beginning of the pandemic in 2020, her experience with overcoming analysis paralysis, and the importance of having a clear plan and understanding one's investment goals. Sheila offers practical advice for both new and experienced investors on property selection, underwriting processes, financing strategies, and the value of mentorship in navigating the competitive field of short-term rental investments. Connect with Sheila Hrinda on LinkedIn | |||
| 03 Dec 2024 | Part 1: How to Be a Good STR Neighbor | 00:15:30 | |
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, staying informed about local regulations to protect your investments, and contributing to the broader STR community to support other hosts and gain valuable insights. He also discusses how small actions, like maintaining your property’s appearance and building trust with nearby residents, can make a big difference in avoiding conflict and ensuring long-term success. Whether you’re an established host or just starting, this episode offers practical tips to elevate your STR game while creating harmony in your community. Enjoy! In This Episode You'll Learn:
Resources: Connect with Kenny on LinkedIn | |||
| 29 Oct 2024 | Part 1: The Beginner's Luck Trap | 00:19:28 | |
What’s the secret to sustainable success in short-term rentals? In this solo episode of Cash Flow Positive, Kenny takes listeners through the pitfalls of what he calls the “beginner’s luck trap” and offers insights on how to achieve steady, long-term growth in today’s shifting market. Kenny explains why strategies that worked for short-term rental investors a few years ago may no longer be effective and why the market now demands a more nuanced approach. He also introduces concepts like “fast,” “medium,” and “slow” money, helping listeners understand which type of investment return might be right for their goals and financial situation. This episode is packed with practical advice for both new and seasoned investors on how to evaluate properties effectively, navigate a maturing market, and avoid common mistakes. If you’re ready to adopt a strategy for long-term success, this episode is a must-listen. Enjoy! In This Episode You'll Learn:
Resources: Connect with Kenny on LinkedIn | |||
| 21 Jan 2025 | Part 1: The 2-Door Strategy with Dr. Rachel Gainsbrugh | 00:39:22 | |
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 courage to embrace a new identity, one that breaks free from the confines of a traditional career path and embraces entrepreneurship. Kenny and Dr. Rachel also touch on practical advice for those considering a shift toward entrepreneurship, especially for those who feel they might be on the edge of burnout or dissatisfaction in their current roles. This conversation offers a thought-provoking reminder about how serving others with authenticity can lead to unexpected success. 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:
Resources: | |||
| 06 Mar 2025 | Part 2: Your Secret Weapon for Success with Tanya Rooney | 00:41:22 | |
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:
Resources: Connect with Kenny on LinkedIn Connect with Tanya on LinkedIn | |||
| 18 Mar 2025 | Part 1: This is How YOU Scale | 00:21:04 | |
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. Additionally, he breaks down why partnerships and collaborations are the key to overcoming capital constraints and how to navigate the quantity vs. quality debate when expanding your portfolio. If you’re looking to grow your STR investments but feel stuck, this episode provides a clear roadmap for taking the next step—whether that’s buying your first property, securing funding for expansion, or building strategic partnerships to accelerate growth. Enjoy! In This Episode You'll Learn:
Resources: Connect with Kenny on LinkedIn | |||
| 25 Feb 2025 | Part 1: How to buy deals out-of-state | 00:19:52 | |
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:
Resources: Connect with Kenny on LinkedIn | |||
| 02 Oct 2024 | Part 1: Technology that increases your cash flow | 00:22:35 | |
In today's episode of the Cashflow Positive podcast, Kenny discusses how operators can avoid overcomplicating their setups with unnecessary tools and expensive software. You'll discover how, by focusing on the core elements that truly matter, you can reduce stress and keep things running smoothly without being bogged down by overwhelming tech demands. Discover the value of strategic decision-making when it comes to technology, pricing, and marketing. Rather than jumping into complex platforms, listeners are encouraged to choose affordable, user-friendly options that get the job done without overburdening their operations. This episode shows how, by being selective with investments and prioritizing the right strategies, operators can scale successfully without getting caught in unnecessary subscriptions or tools. 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:
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| 10 Dec 2024 | Part 1: Finding High ROI STR Deals with No Money | 00:19:54 | |
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 appreciation, and approaching investments as a real estate investor first and a hospitality provider second. From leveraging seller credits to mastering the BRRRR strategy, this episode is packed with practical tips to help you find deals that cash flow without breaking the bank. Whether you’re new to STRs or looking to scale your portfolio on a budget, this episode offers the insights you need to take action and start building wealth. Enjoy! In This Episode You'll Learn:
Resources: Connect with Kenny on LinkedIn | |||
| 11 Feb 2025 | Part 1: Is it worth investing in Blue states? | 00:16:28 | |
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:
Resources: | |||
| 16 Jul 2024 | How to determine the ROI from design? (Part 1) | 00:21:25 | |
Kenny shares detailed insights on determining the return on investment (ROI) from property design and décor. He emphasizes the impact of market-specific factors and competitive landscapes on budgeting for design improvements. Kenny outlines four key considerations for evaluating ROI, including the importance of design in your market, comparisons between properties with varying design qualities, the benefits of targeted design strategies, and the necessity of using available data to make informed decisions. He also provides rough budget guidelines based on different market competitiveness levels and bedroom counts. The episode concludes with a teaser for the next episode featuring an interview with a professional designer. | |||
| 02 Jul 2024 | Is it my pricing, listing, or amenities - Pricing Segment (Part 1) | 00:18:19 | |
Kenny delves deep into the critical topic of pricing strategies for vacation rental properties. Kenny emphasizes the importance of understanding and optimizing pricing before facing booking issues or market saturation. He discusses how to evaluate and adjust pricing, listing descriptions, and amenities to ensure competitive edge and higher revenue. Using a specific case study from Black Mountain, North Carolina, he demonstrates how improper pricing and high cleaning fees can impact bookings negatively. Kenny also outlines the need for dynamic pricing adjustments based on booking lead time and encourages proactive revenue management. Tune in to learn actionable tips to maximize your cashflow and stay ahead in the vacation rental market. | |||
| 17 Dec 2024 | Part 1: Where Should You Invest? | 00:16:36 | |
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 of budget planning and investment readiness, ensuring you’re not just investing, but doing so wisely. Kenny will introduce two crucial concepts: bankability and affordability. These serve as guiding pillars for determining your financial limits and leveraging your resources effectively. From understanding what lenders evaluate when approving loans to ensuring you have sufficient capital for property improvements, Kenny will walk you through actionable steps to maximize their purchasing power. Whether you're starting small with a one-bedroom rental or scaling to larger, high-revenue properties, Kenny offers a balanced perspective on the time, effort, and financial outcomes involved. 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:
Resources: | |||
| 23 Jul 2024 | Your biggest mistake when you scale (Part 1) | 00:17:53 | |
Kenny Bedwell discusses the common pitfalls of scaling short-term rental portfolios and offers solutions to avoid these mistakes. Kenny emphasizes the importance of focusing on quality over quantity, implementing property management software, utilizing dynamic pricing tools, building robust marketing strategies, establishing standard operating procedures, and tracking financial performance through accounting software. With his insights, Kenny aims to help both novice and seasoned investors achieve time freedom and business growth in the short-term rental industry. | |||
| 22 Oct 2024 | Part 1: How to Drive More Bookings Through Social Media Marketing | 00:18:04 | |
How can social media be used effectively to drive more bookings for your short-term rentals? In this solo episode of Cashflow Positive, Kenny dives deep into the strategies for leveraging social media to grow your business. Whether you're managing one property or multiple, understanding the power of social media marketing is essential to scaling without relying entirely on OTAs like Airbnb and VRBO. Kenny shares personal experiences, lessons learned, and practical tips on creating a presence that drives direct bookings, builds a brand, and attracts your target guests. Kenny walks listeners through the importance of having a direct booking site, how to vet social media marketers, and why simply posting your Airbnb link won’t cut it. He explains how to shift the focus from just marketing your property to promoting the location, offering insights on building content that appeals to cold leads and warms them up into future guests. If you're ready to step up your social media game, this episode is packed with actionable advice to get you started. Enjoy! What You'll Learn In This Episode:
Resources: Connect with Kenny on LinkedIn https://www.linkedin.com/in/kenneth-bedwell-9680a8113/ Follow Kenny on Instagram https://www.instagram.com/kenny_bedwell/ Episode mentioned: Does ranking on Airbnb actually matter? (Part 2) https://podcasts.apple.com/ca/podcast/does-ranking-on-airbnb-actually-matter-part-2/id1742644291?i=1000667002580 | |||
| 27 Feb 2025 | Part 2: How to buy deals out-of-state with Jeana Deninger | 00:43:54 | |
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:
Resources: Connect with Kenny on LinkedIn Connect with Jeana on LinkedIn | |||
| 05 Dec 2024 | Part 2: How to Be a Good STR Neighbor with Alex Shapiro | 00:33:25 | |
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 conversation covers the journey of Can Monkey from a small idea to a multi-state operation, serving thousands of properties. Alex and Kenny discuss how streamlined services like trash handling can save time, improve guest experiences, and build trust within neighborhoods. Whether you’re managing one property or an entire portfolio, this episode provides insights into the value of consistency, automation, and being a good neighbor in your STR business.Enjoy! In This Episode You'll Learn:
Resources: Connect with Kenny on LinkedIn | |||
| 27 Mar 2025 | Part 2: Types of STR Markets No One is Talking About with Maria Reith | 00:38:08 | |
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. She reveals why military bases create consistent rental demand, how she balances short-term, midterm, and long-term rentals, and why word-of-mouth marketing plays a huge role in her success. Maria also shares her approach to creative financing, how she finds value-add properties, and the one thing investors should always research before buying near a military base. If you're looking for new STR markets with steady cash flow, this episode will open your eyes to a powerful, under-the-radar investment strategy. Listen now and njoy! In This Episode You'll Learn:
Resources: Connect with Kenny on LinkedIn | |||
| 13 Aug 2024 | The #1 ROI for your property (Part 1) | 00:18:20 | |
Kenny reveals the top strategy to maximize ROI for short-term rental properties: high-quality photography. Kenny emphasizes that professional photos, particularly those that evoke emotion and show the property's best features, are crucial to attracting guests. He shares detailed tips on how to choose the right photographer, the importance of a hero image, the types of shots that perform well on platforms like Airbnb, and how to effectively communicate your needs to photographers. Additionally, Kenny dispels common misconceptions about property photos and provides actionable advice to help property owners improve their listings’ marketability and booking rates. | |||
| 20 Feb 2025 | Part 2: Creative Financing STR's with Brandon Thompson | 00:44:12 | |
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:
Resources: Connect with Kenny on LinkedIn Connect with Brandon on LinkedIn | |||
| 04 Jun 2024 | Is It Too Late To Invest In Short-Term Rentals? (Pt. 1) | 00:17:42 | |
Is it too late to invest in short-term rentals? In today’s Part 1 episode, I’m sharing a detailed analysis, talking about treating STRs as an active business rather than a passive investment, the importance of understanding market revenue drivers, and more. Stay tuned for part 2 to hear from an expert in the STR industry about this frequently asked question! | |||
| 23 May 2024 | What Is Dirty Data and How Can We Avoid It? (Pt. 2) | 00:39:50 | |
Joe Rohne, real estate agent and investor, joins us this week to discus the challenges and lessons learned from using unreliable data in real estate investment. Joe shares his journey from participating in an accelerator program to owning and co-hosting short-term rentals in Panama City Beach and Branson, Missouri. We focus on why it's important to have accurate, season-specific data and robust performance analysis to avoid making poor investment decisions based on 'dirty data'. | |||
| 19 Dec 2024 | Part 2: Where Should You Invest? | 00:41:23 | |
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 episode, Kenny will highlight the dynamic interplay between accessibility and exclusivity, showcasing how proximity to attractions and thoughtful property enhancements can elevate performance. The discussion balances affordability and market demand, with specific insights on untapped regions. By exploring the intersection of market trends, strategic timing, and creative approaches, this episode will spark curiosity and inspire you to investigate new opportunities. 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:
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| 05 Nov 2024 | Part 1: The Easiest Deal Finding Strategy | 00:21:12 | |
In this episode, Kenny shares his proven strategy for uncovering profitable short-term rental properties. Centered around the "moat" principle, Kenny emphasizes finding unique features that make a property stand out and protect it from competition. He identifies four key moat categories—location, property quality, design/decor, and amenities—and advises on stacking multiple moats to create a truly resilient investment. Through practical examples, Kenny shows how overlooked properties can have hidden cash flow potential. He also shares specific tips for identifying these high-potential deals and stresses the importance of looking beyond obvious attributes. Explore Kenny’s “moat”-focused strategy today and reach out to him for guidance on finding valuable deals in your target markets. If you've enjoyed this episode of the Cashflow Positive podcast, be sure to leave a review and subscribe today! What You'll Learn in this Show:
Resources: | |||
| 20 Mar 2025 | Part 2: This is How YOU Scale with Tony Stancato | 00:41:18 | |
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 challenges of short-term rental investing. Whether you're just starting out or looking to scale your STR portfolio, this episode is packed with practical insights on building a business that creates wealth, not just cash flow. If you've enjoyed this episode of the Cash Flow Positive podcast, be sure to leave a review and subscribe today! Listen now and enjoy! In This Episode You'll Learn:
Resources: Connect with Kenny on LinkedIn Michigan Short Term Rentals Podcast | |||
| 24 Oct 2024 | Part 2: How To Drive More Bookings Through Social Media Marketing with Emily Lethgo | 00:39:54 | |
In today's episode of the Cashflow Positive podcast, Kenny is joined by Emily Lethgo, Social Media Manager and Coach at Match Point Socials and The Profitable Host. Throughout the conversation, Emily and Kenny explore fresh strategies for boosting success in a competitive field through savvy use of tools that can turn a side hustle into a profitable venture. Emily shares a wealth of knowledge, offering insights into behind-the-scenes tactics that add a personal touch and make an impact. You'll discover creative approaches to content creation that work even when managing from afar. With a focus on consistency and analytics, the conversation emphasizes how to track what works, adjust tactics, and stay committed to long-term goals. This episode shows why steady efforts, grounded in realistic goals, are the foundation for sustained growth. 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:
Guest Bio: Emily Lethco is a Social Media Manager and Coach at Match Point Socials and The Profitable Host, with five years of experience in social media marketing. She holds a bachelor's degree in psychology from East Tennessee State University and an MBA from Tennessee Tech, focusing on entrepreneurship and marketing. Emily's expertise in understanding human behavior and building brands has driven her success, particularly in the short-term rental industry. After purchasing a cabin in the Smoky Mountains, she applied her skills to grow the property's brand and increase bookings through strategic content creation. Emily now extends her services to other rental owners and hospitality brands, helping them enhance their online presence and build strong connections with their audiences. Resources: Disclaimer: The views, information, or opinions expressed during this podcast are solely those of the individuals involved and do not necessarily represent those of the Cashflow Positive podcast or its affiliates. The content provided is for informational and entertainment purposes only and is not intended to be a substitute for professional advice. We make no representations as to the accuracy, completeness, suitability, or validity of any information on this podcast and will not be liable for any errors, omissions, or delays in this information or any losses, injuries, or damages arising from its display or use. Listeners should consult with a professional for specific advice tailored to their situation. By accessing this podcast, you acknowledge that any reliance on the content is at your own risk. | |||
| 10 Sep 2024 | The STR tortoise vs the hare - why we want the hare to win (Part 1) | 00:19:11 | |
In today's episode of the Cashflow Positive podcast, Kenny uses a clever analogy involving the famous tale of the tortoise and the hare to illustrate a key principle for success in managing short-term rentals. You'll discover the importance of launching rental properties quickly, avoiding the common pitfalls of slow decision-making, and utilizing strategic multitasking to maximize cash flow. Go on a journey through the process of preparing a rental property for market, from handling renovations and furnishing to optimizing listings for early bookings. With insights on balancing cost-saving measures and hiring professionals, this episode promises practical strategies for achieving fast and profitable rental property launches. If you've enjoyed this episode of the Cashflow Positive podcast, be sure to leave a review and subscribe today! In This Episode You'll Learn:
And much more... Resources: Connect with Kenny on LinkedIn! Disclaimer: The views, information, or opinions expressed during this podcast are solely those of the individuals involved and do not necessarily represent those of the Cashflow Positive podcast or its affiliates. The content provided is for informational and entertainment purposes only and is not intended to be a substitute for professional advice. We make no representations as to the accuracy, completeness, suitability, or validity of any information on this podcast and will not be liable for any errors, omissions, or delays in this information or any losses, injuries, or damages arising from its display or use. Listeners should consult with a professional for specific advice tailored to their situation. By accessing this podcast, you acknowledge that any reliance on the content is at your own risk. | |||
| 04 Mar 2025 | Part 1: Your Secret Weapon for Success | 00:16:54 | |
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:
Resources: Connect with Kenny on LinkedIn | |||
| 30 Apr 2024 | Is My Airbnb Market Saturated? (Pt. 1) | 00:17:20 | |
This week, Kenny is addressing the common concerns surrounding market saturation in the short-term rental industry. He talks about the concept of market saturation, explaining that it's not markets but properties that become saturated. You’ll learn a formula to measure saturation based on revenue per active rental comparisons year over year and Kenny emphasizes the importance of considering bedroom count when assessing saturation. He offers strategic advice on finding opportunities in seemingly saturated markets by focusing on unique property features and amenities, rather than the broader market trends. Kenny also shares examples, including an analysis of the Orlando market, to help listeners understand how to calculate and interpret saturation levels for their investments. | |||
| 18 Jul 2024 | How to determine the ROI from design? (Part 2) | 00:36:25 | |
Kenny discusses achieving maximum ROI from design and decor with Paige Hayes from Hayes and Company Interiors. Paige shares her expert insight into the strategies of integrating design into short-term rental properties to boost their appeal and financial return. Topics range from identifying the property's story, managing design budgets, to understanding market-specific adjustments. Listeners will also deep dive into a specific case study of a property on the Bourbon Trail in Kentucky, and learn Paige's unique approach to setting up spaces that attract guests and ensure a profitable experience for property owners. | |||
| 25 Apr 2024 | Cash on Cash vs. Cash Flow? (Pt. 2) | 00:26:02 | |
Welcome to Part 2 of Cash on Cash vs. Cash Flow! In this second part, you'll hear from Katie, an art teacher who ventured into real estate investment as a backup plan during COVID-19. After purchasing a duplex and managing it successfully, Katie and her husband dove into short-term rentals, buying a property by the beach with Kenny's guidance. They discuss the process of selecting the right market, the importance of cash on cash versus cash flow evaluation, and Katie's personal preference for a vibrant, colorful property close to the beach. Katie shares her experience and plans for transforming her new property into a lively vacation rental, emphasizing outdoor living spaces and gives advice and encouragement for listeners considering their first short-term rental investment. | |||
| 04 Feb 2025 | Part 1: The "Good" Deal Gone Bad | 00:16:08 | |
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 that could mean the difference between long-term success and a costly mistake. You'll learn how even the most well-intentioned strategies can backfire, leaving investors scrambling for a way out. Kenny explores why some deals unravel despite careful planning and what factors should truly guide an investment decision. Whether you’re new to real estate or a seasoned investor, this conversation will prompt you to rethink conventional wisdom and equip you with a smarter approach to navigating the market. 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:
Resources: | |||
| 26 Nov 2024 | Part 1: The #1 Hack to Scale Your Business | 00:16:25 | |
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. He also explains how many investors fall into the trap of trading their nine-to-five job for another job by focusing solely on the number of doors they manage. He discusses the importance of prioritizing cash flow and hiring the right team, especially virtual assistants, to handle repetitive and time-consuming tasks. This episode is packed with insights on how to create a scalable business model, achieve a higher time ROI by investing in people, and adopt the mindset of a true CEO. Whether you’re managing a few properties or planning to expand your portfolio, Kenny’s actionable advice will inspire you to work smarter, prioritize what matters, and achieve more freedom in your business and personal life. Enjoy! In This Episode You'll Learn:
Resources: Connect with Kenny on LinkedIn | |||
| 12 Sep 2024 | PART 2 Kim Fitzpatrick - The STR tortoise vs the hare - why we want the hare to win | 00:36:34 | |
In today's episode of the Cashflow Positive podcast, Kenny is joined by Kim Fitzpatrick, the CEO of Launched Host, a company that works with short-term rental designers to get their plans installed in as little as a week. During the conversation, Kenny and Kim dive into a lively discussion about navigating unexpected challenges in a demanding and unpredictable field. They highlight the importance of preparation, patience, and resilience when taking on complex projects. You'll discover real-world examples of the mental, physical, and emotional strain that can accompany high-stakes work. Kim offers insights into the value of meticulous planning and the balance required to juggle multiple responsibilities. This episode serves as a motivational reminder that, while the journey can be tough, it’s important to have a clear strategy and to lean on others for support. 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:
Resources: | |||
| 14 Nov 2024 | Part 2: Who Cares About Macro Trends? The Secrets to STR Success with Fouad Bazzi | 00:43:13 | |
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 insights into building a business with focus, managing properties across multiple markets, and adapting to regulatory challenges. Whether it’s diversifying income streams, hiring strategically, or mastering the "why" behind your goals, this episode equips listeners with the tools and mindset needed to thrive in today’s evolving STR landscape. Enjoy! In This Episode You Will Learn:
Resources: Connect with Kenny on LinkedIn | |||
| 07 May 2024 | How to Find Secret Emerging Markets? (Pt. 1) | 00:16:36 | |
Welcome to Part 1 of how to find secret emerging markets! In this episode you will hear about the common pitfalls of chasing popular markets in real estate investment and introduces strategies for identifying and investing in emerging markets instead. I shares insights into what defines an emerging market, including rapid and consistent demand growth and a limited number of active listings. This episode covers practical tips for researching potential emerging markets using data on tourism, short-term rentals availability, and ROIs, with specific reference to locations like Blue Ridge, North Georgia, and areas around national parks. | |||
| 12 Nov 2024 | Part 1: Who Cares About Macro Trends? The Secrets to STR Success | 00:17:24 | |
Do macro trends in the short-term rental industry really matter? In this solo episode of Cash Flow Positive, Kenny breaks down why focusing on broad industry statistics could be misleading for individual investors. With revenue per property declining across many markets, Kenny explains why properties with unique "moats" consistently outperform, regardless of overall market conditions. He emphasizes the importance of studying specific markets, understanding barriers to entry, and building properties that stand out. Kenneth challenges listeners to shift their focus from average data to actionable insights that lead to success. He provides practical advice on evaluating properties, balancing occupancy and ADR, and why understanding your property's unique value proposition can insulate you from industry-wide downturns. If you're ready to rise above the average and thrive in today’s competitive landscape, this episode is for you. In This Episode You'll Learn:
Resources: Connect with Kenny on LinkedIn | |||
| 11 Jun 2024 | Secret Deal Finding Strategies (Pt. 1) | 00:18:00 | |
Are you looking for new ways to find real estate deals? Tune in to hear secret strategies with detailed examples and methods to help you think outside the box and optimize your real estate investments! | |||
| 31 Oct 2024 | Part 2: The Beginner's Luck Trap: Achieving Long-Term Growth in a Changing STR Market with Ryan Bakke | 00:58:25 | |
This episode of the Cashflow Positive podcast is part two of "The Beginner's Luck Trap." This time out, Kenny sits down with Ryan Bakke, host of the Learn Like a CPA podcast to discuss the hidden dynamics of investment success. You'll hear about the allure of different asset classes along with insights on how initial wins can lead to false confidence. Through relatable analogies and real-world examples, Kenny and Ryan highlight how unpredictable events can disrupt even the best-laid plans, making a strong case for caution, adaptability, and the value of building a financial safety net. Discover the power of strategic diversification, as the hosts illustrate how this approach can create unexpected vulnerabilities, especially in specific sectors or regions prone to market shifts and environmental impacts. Kenny and Ryan reveal how diversifying across different markets and types of investments helps to buffer against risk and maximize returns. With a blend of humor and expertise, the episode offers deeper strategies that investors can apply, whether you're just starting out or already managing a diverse portfolio. 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:
Resources: | |||
| 23 Apr 2024 | Cash on Cash vs. Cash Flow? (Pt. 1) | 00:17:20 | |
Welcome to the Cash Flow Positive podcast, hosted by Kenny Bedwell! This show is aimed at helping listeners achieve financial freedom through short-term rentals. In this first episode, Kenny outlines his vision for the show: a format that combines straightforward advice (Part 1 of each episode) with real-world applications and interviews (Part 2). Today, Kenny is diving into the importance of cash flow over cash on cash return and shares strategies for setting investment goals based on personal criteria and market understanding. This episode is a resource for both novice and seasoned investors looking to optimize their property portfolios for better cash flow. | |||
| 13 Jun 2024 | Secret Deal Finding Strategies (Pt. 2) | 00:34:50 | |
Savvy realtor and short-term rental expert Tyler Coon joins for this week's part 2 episode on secret deal finding strategies! Tyler shares his unique strategies for finding hidden deals in the market, a recent success story involving a property that grossed $210,000 to $250,000 in its first year, and insights into the benefits of creative financing and the importance of amenities. Tyler also talks about maximizing cash flow, sharing valuable tips on executing successful short-term rental investments. Connect with Tyler on LinkedIn | |||
| 18 Jun 2024 | Is Property Management Actually Worth It? (Pt. 1) | 00:17:40 | |
Is property management actually worth it? In today’s Part 1 episode, I’m covering the common misconceptions surrounding property management within the STR industry. I talk about the potential benefits of hiring property managers, the importance of utilizing technology, hiring virtual assistants, and how to enhance property performance without relying on expensive property management firms. | |||
| 26 Sep 2024 | Part 2: Marc Hostovsky - Real Estate vs Hospitality: The Secret to Profitable Short-Term Rentals | 00:47:05 | |
How do you transform a short-term rental from a basic property into a hospitality experience that keeps guests coming back? In this episode of Cashflow Positive, Kenneth Bedwell sits down with Marc Hostovsky, the founder and CEO of Minoan, to dive into the essential shift from real estate thinking to hospitality-focused management. Learn how Marc's innovative approach helps hosts maximize the potential of their properties through thoughtful design, furnishings, and guest experiences. Marc shares his journey from working at a fast-growing startup to founding Minoan, a platform that allows hosts to access exclusive discounts and marketing opportunities from top brands. More importantly, Marc explains why creating spaces that guests love to experience—not just visit—is key to unlocking higher revenue and building a successful rental business. Curious about how you can boost your nightly rates with just a few design changes? Wondering if investing in high-quality furnishings is really worth it? Marc breaks down the balance between making smart investments and providing a memorable guest experience, and why focusing on hospitality can lead to long-term profitability. In This Episode You'll Learn:
Resources: Connect with Marc on LinkedIn - https://www.linkedin.com/in/marc-hostovsky/ Follow Marc on Instagram - https://www.instagram.com/minoanexperience/?hl=en Minoan.com - https://minoan.com/ Connect with Kenny on LinkedIn - https://www.linkedin.com/in/kenneth-bedwell-9680a8113/ Follow Kenny on Instagram - https://www.instagram.com/kenny_bedwell/ | |||
| 10 Apr 2025 | Part 1: My Airbnb Guest Just Sued Me | 00:15:41 | |
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 financial risk that comes with unexpected accidents, lawsuits, and worst-case scenarios. If you’re investing in STRs or planning to, this episode is essential listening. From legal layers to loss-of-income coverage, Kenny walks you through the lessons he learned the hard way—so you don’t have to. If you've enjoyed this episode of the Cash Flow Positive podcast, be sure to leave a review and subscribe today! Listen now and enjoy! In This Episode You'll Learn:
Resources: Connect with Kenny on LinkedIn | |||
| 15 Aug 2024 | The #1 ROI for your property (Part 2) | 00:41:14 | |
Kenny speaks with Andrew Keller, a leading short-term rental photographer. They discuss the importance of professional photography in enhancing property listings, share tips for staging and preparing properties for a photo shoot, and emphasize the significance of 'scroll-stopping' images. Andrew details his meticulous process, including the use of drone shots and twilight photos, and shares client success stories showing significant revenue increases. The episode is a comprehensive guide on how to leverage high-quality photography to boost bookings and revenue for short-term rental properties. | |||
| 09 May 2024 | How to Find Secret Emerging Markets? (Pt. 2) | 00:34:41 | |
Welcome to Part 2 of how to find secret emerging markets! I’m excited to be joined by Will Van Wickler, a leading real estate agent focusing on emerging short-term rental markets in New England. We talk about identifying and capitalizing on emerging markets in Maine, New Hampshire, and Vermont, with a detailed exploration of areas like Sunday River, Bar Harbor, and Old Orchard Beach. Will shares his journey from cybersecurity student to real estate investor and agent and discusses the significance of choosing the right locations, accurately projecting expenses, and the art of revenue management to achieve positive cash flow. You’ll also hear about the resilience and growth of New England's STR market, despite challenges and fluctuations in seasonal demand. Stick around for the end, you won’t want to miss Will’s tips for new investors! | |||
| 19 Sep 2024 | Part 2: The Profit Power of Hospitality: Maximize Your ROI by Elevating Guest Experiences with Superior Hospitality | 00:45:22 | |
Have you ever wondered what makes a guest experience truly unforgettable? Whether you're a short-term rental host or just looking for ways to improve your business, elevating your guest experience is key. In today's episode of the Cashflow Positive podcast, you will learn more about the small but impactful details that can transform a guest’s stay from average to extraordinary—and why it's not just about fancy amenities. In this second part of “Maximize Your ROI by Elevating Guest Experiences with Superior Hospitality”, Kenny is joined by Sarah Karakaian and Annette Grant, founders of Thanks for Visiting and seasoned short-term rental hosts. With 34 properties under their management, they know a lot about creating a lasting impression on guests. Their mission? To elevate the short-term rental industry and inspire hosts to think like business owners, not just side hustlers. Curious about how a simple handwritten card can lead to rave reviews or why hiring an inspector could save you from bad feedback? Want to learn how patience and strategic risk-taking can increase your revenue, even in a competitive market? Kenny and his guests explore these topics and more, including the hidden tactics that successful hosts use to stay ahead of the competition. If you're ready to take your short-term rental game to the next level and unlock the secrets to a five-star guest experience, hit play and enjoy! In This Episode You'll Learn:
Resources: ThanksforVisiting Instagram Page ThanksForVisiting Youtube Channel | |||
| 13 Mar 2025 | Part 2: Amenities That Change the Game with Jose Cornejo | 00:32:26 | |
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 can turn a property into a revenue-generating machine. Jose shares his insights on why not all amenities increase revenue, how seasonal upgrades can impact demand, and why marketing your amenities properly is just as important as offering them. He also discusses the biggest mistakes investors make when upgrading their properties and how to create an experience that justifies premium pricing. If you’re looking for data-backed strategies to maximize revenue and optimize guest experience, this episode will help you stand out in the crowded STR market and boost your bottom line. Enjoy! In This Episode You'll Learn:
Resources: Connect with Kenny on LinkedIn | |||
| 03 Apr 2025 | Part 2: Recent Hard Lessons Learned | 00:33:40 | |
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 miss when budgeting for renovations, managing out-of-state setups, and relying too heavily on contractors without local oversight. He also digs deep into market conditions, sharing what he’s seeing as the industry matures, where opportunity still lies, and why having a “moat” around your investment is more crucial than ever. If you've enjoyed this episode of the Cash Flow Positive podcast, be sure to leave a review and subscribe today! Listen now and enjoy! In This Episode You'll Learn:
Resources: Connect with Kenny on LinkedIn Part 1: Types of STR Markets No One is Talking About | |||
| 17 Sep 2024 | Part 1: Maximize Your ROI by Elevating Guest Experiences with Superior Hospitality | 00:21:51 | |
In today's episode of the Cashflow Positive podcast, Kenny discusses how elevating the guest experience can dramatically impact your ROI in short-term rentals. While the focus is often on choosing the right property and market, Kenny shifts the spotlight to the crucial, yet frequently overlooked, element of hospitality. You'll discover how excelling in this area can significantly boost your financial returns, challenging the misconception that great hosting only involves personal touches like baking cookies or offering flowers. Kenny also discusses the importance of sustainable and replicable hospitality practices that go beyond the typical hands-on approaches, advocating for automating and systematizing guest interactions to maintain a personal touch without requiring constant physical presence. This episode shows how maintaining a high level of care, precision and quality control, not only ensures a great guest experience - leading to five-star reviews - but also optimizes your property’s profitability. 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:
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| 28 Jan 2025 | Part 1: Should I Use a Commercial Loan for My STR Purchase? | 00:15:33 | |
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 loans, understanding debt-to-income (DTI) ratios, and the critical importance of running your numbers before finalizing any deal. If you’re looking to scale your short-term rental portfolio and want to avoid costly mistakes, this episode is packed with actionable insights to guide your financing decisions. In This Episode You Will Learn:
Resources: Connect with Kenny on LinkedIn | |||
| 24 Sep 2024 | Part 1: Real Estate vs Hospitality: The Secret to Profitable Short-Term Rentals | 00:17:42 | |
Can short-term rentals really deliver the financial freedom many investors expect? In this episode, listeners can learn the critical difference between short-term rentals and traditional real estate investments. It’s not just about buying properties—it’s about running a hospitality business, where guest experience is everything. During this episode, Kenny clears up the common misconception that short-term rentals are easy, passive income. He explains why success in this space relies heavily on mastering hospitality, not just real estate. Kenny emphasizes the importance of putting in the time and effort to create five-star experiences for guests, sharing insights on how to maintain profitability in this hands-on industry. Listeners will be encouraged to rethink their approach to short-term rentals by focusing on what really drives success: understanding the hospitality aspect of the business and having the right motivation to stay committed long-term. Tune in to find out essential strategies for creating a sustainable, cash-flow-positive rental business. Listen now and enjoy! In This Episode You'll Learn:
Resources: | |||
| 07 Nov 2024 | Part 2: The Easiest Deal Finding Strategy | 00:45:18 | |
Ever wondered how to spot the hidden gems in the real estate market that others miss? In part 2 of this week’s series, Kenny dives deeper into his proven strategies for finding short-term rental deals that truly stand out. With a focus on making data-driven decisions, he explains why relying solely on advice from realtors or gurus won’t cut it in today’s market. He shares how understanding the unique characteristics of successful properties and leveraging overlooked opportunities can make all the difference. Kenny also breaks down how to evaluate properties that have the potential but need the right touch to turn into high-yield investments. He emphasizes the importance of emotional intelligence in decision-making and explains why recognizing your comfort zone before investing is crucial. This episode provides listeners with actionable insights on how to navigate seller credits, concessions, and how interest rates affect cash flow, ensuring that your next property is a smart investment. Enjoy! In This Episode You Will Learn:
Resources: Connect with Kenny on LinkedIn Register and reserve your seat for the FREE workshop of Finding Wildly Profitable STR's at this link | |||
| 03 Oct 2024 | Part 2: Cody Wood - Technology that increases your cash flow | 00:47:21 | |
How do you build systems that actually help your short-term rental business grow—and not just add more chaos? In this episode of Cashflow Positive, Kenny welcomes Cody Wood, a seasoned operations expert who has managed over 187 short-term rental properties and specializes in creating streamlined systems. Cody shares his journey of scaling up to nearly 200 properties and realizing the critical importance of trimming inefficiencies, building SOPs, and using the right technology to drive sustainable growth. Listeners will learn about the pitfalls of "shiny object syndrome" when it comes to adopting new tech and why it’s crucial to understand what really fits your business. Cody also explains the transformative effect of focusing on fewer but more profitable properties and offers insights into what systems are truly necessary for operators just starting out. Whether you’re managing one property or twenty, Cody’s insights on optimizing processes and scaling effectively will help take your rental business to the next level. Curious about what property management software is right for you, or whether you really need all those subscriptions? Cody provides practical tips on how to determine what’s essential and how to avoid adding unnecessary complexity to your operations. In This Episode You’ll Learn:
Resources: | |||