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:Transition from treating your business like a job to embracing your role as a CEOFocus on building a business that achieves financial freedom rather than trading one job for anotherHire the right people with a mindset for growth and ownershipMotivate your team members to grow alongside your business by offering opportunities and incentivesFoster an environment where employees can offer constructive feedback and take ownership of challengesShift your focus from managing day-to-day tasks to overseeing strategic growth and scaling effectivelyAnd much more…Resources:Connect with Kenny on LinkedInFollow Kenny on InstagramBook:Who Not How: The Formula to Achieve Bigger Goals Through Accelerating Teamwork

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:Think like a real estate investor first, not just a short-term operator​Begin with the end in mind and reverse engineer your goals for clarity and direction​Stay true to your values and align your strategy with your "why"​Use tools like STR Insights and rely on data to understand where you can truly cash flow​Don’t be afraid to expand your skills by managing other properties or offering co-hosting services​Build a team strategically by hiring people who can complement your strengths and bring experience​Regulatory risks make it crucial to focus on markets with mature rules and a history of supporting STRs​Seek mentorship and education to avoid common pitfalls and accelerate your growth​And much more…Resources:Follow Fouad on InstagramConnect with Kenny on LinkedInFollow Kenny on Instagram

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:Why properties with "moats" are less impacted by macro trends Understanding the barriers to entry in a specific market is crucial before investingFocusing on occupancy balance and ADR optimization maximizes revenue potentialAvoid relying on average market data; instead, study individual market attributesRevenue can still increase for top-performing properties, even when market averages declineAnd much more…Resources:Connect with Kenny on LinkedInFollow Kenny on Instagram

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:The importance of making data-driven decisions over relying on gut feeling or generic adviceHow studying the characteristics of successful properties in your target market leads to smarter investmentsThe value of finding properties that have strong fundamentals but need improvements to reach their potentialUnderstanding emotional factors in investments and aligning them with your comfort zoneLeveraging seller credits and concessions to optimize your investment strategyHow interest rates directly impact monthly cash flow and overall investment successAnd much more…Resources:Connect with Kenny on LinkedInFollow Kenny on InstagramRegister and reserve your seat for the FREE workshop of Finding Wildly Profitable STR's at this link

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:The importance of understanding the "moat" principle for short-term rental successThe four key moat categories and how to identify themWhy design and decor alone are not enough to create a sustainable competitive advantageSpecific property attributes that correlate with the ability to gross $200,000+ annuallyHow to spot hidden gems that have been overlooked by the marketKenny's personal approach to finding and evaluating high-potential dealsAnd so much more…Resources:Kenny’s LinkedInKenny’s Instagram

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:The importance of balancing risk and safety in investments, particularly in real estate, and the pitfalls of putting too much net worth into a single property.The concept of a "Buy Box" for properties that meet specific net income criteria, similar to commercial real estate trading.Why having multiple scenarios in pro forma analysis helps account for potential risks and ensure financial stability.The value of understanding the political and economic climate of the areas where investments are made, to aid in risk mitigation.And much more...Resources:Learn Like a CPA podcastRyan's LinkedInKenny’s LinkedInKenny’s Instagram

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:Understanding the “beginner’s luck trap” and why past strategies may not work todayHow to categorize investment returns as “fast,” “medium,” or “slow” moneyWhy adapting to a maturing industry is essential for staying competitiveThe importance of evaluating properties based on current market conditionsWhy “slow money” investments offer tax benefits and wealth-building opportunities over timePractical advice on choosing the right investment strategy based on market trends and personal goalsAnd much more…Resources:Connect with Kenny on LinkedInFollow Kenny on Instagram

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:How Emily started using social media to brand her property and build an email list before opening it for bookings. The benefits of showing behind-the-scenes content and engaging with local businesses to grow the audience.Emily's strategy of sending monthly newsletters with valuable information about the location and property.  The various property management software options available and when it makes sense to invest in one.And much more...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:Emily's LinkedInEmily's websiteEmily's InstagramThe Profitable HostDisclaimer: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.

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:You don’t need to be fake on social media to be successfulAs short-term rental hosts, it's critical to look for exposure outside of OTAsInvesting in social media marketing is a must for insulating your business from platform risksBefore diving into social media marketing, ensure you have a direct booking site in placeThe importance of tracking the performance of your social media efforts by monitoring clicks and conversionsPeople book based on the location experience, not just your property, so target your content accordinglyHow to focus your marketing on the right audience to drive bookingsAnd much more…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

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:The importance of catering to a specific demographic for luxury short-term rentalsHow to differentiate your property from competitors by offering unique, high-end amenitiesWhy hospitality and guest experience are more important than just having a beautiful propertyThe benefits of building a brand around your STRs for repeat guests and long-term successAutomating guest communication and operations to save time and reduce stress while scalingHow Jeff generates $500,000 in gross income from one property by working smarter, not harderAnd much more…Resources:Jeff’s LinkedInLuxuryRentals.com  STRdigital.com Connect with Kenny on LinkedInFollow Kenny on Instagram

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.Connect with Kenny on LinkedIn!Follow Kenny on IG

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...

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:The importance of adapting strategies to changing market conditions and economic shifts.Why the industry's growth is not as robust as the Average Daily Rate (ADR) data suggests.The value of finding a unique selling proposition (USP) or "moat" to differentiate properties from competitors.The concept of a wealth divide, where top performers in the 90th percentile outperform the average properties.And much more...

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:Scaling up doesn’t mean adding more propertiesThe 80/20 rule can help cut out unprofitable properties and focus on maximizing returnsThe dangers of adopting technology without knowing if it fits your business.How SOPs (Standard Operating Procedures) can help you manage your operations effectivelyHow to audit your technology stack to keep costs low and improve operational efficiencyWhy adding technology should enhance your business instead of complicating itAnd much more…Resources:STRhub.com [email protected] Cody’s LinkedInSchedule a free 1 on 1 consult with Cody

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:Kenny's personal journey with short-term rentals, fluctuating from six to three properties and planning to add two more.Why rookie operators need to be involved in their property's pricing and revenue management, as no single software is game-changing.The importance of consistency and simplicity in managing cleaning and maintenance processes.The value of keeping expenses low and being efficient with software and subscriptions.And much more...

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:Why short-term rentals are more than just real estate investmentsHow to strategically invest in furnishings and amenities to maximize guest experience and revenueThe importance of identifying your target audience when designing your propertyHow to avoid overspending while still creating a high-end guest experienceWhy short-term rental hosts should view themselves as “four-walled influencers” and capitalize on marketing partnershipsThe value of hospitality-focused design in reaching the full potential of your property’s revenueAnd much more…Resources:Connect with Marc on LinkedIn - https://www.linkedin.com/in/marc-hostovsky/Follow Marc on Instagram - https://www.instagram.com/minoanexperience/?hl=enMinoan.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/

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:Short-term rentals are more than just real estate investments—they require hospitality skillsWhy short-term rentals aren’t passive income and what it really takes to succeedThe importance of defining your “why” to avoid burnout and stay motivatedHow delivering exceptional guest experiences can boost your profitabilityTime management strategies and tips for outsourcing tasks effectivelyThe key differences between managing short-term rentals and traditional real estate investmentsAnd much more…Resources:Connect with Kenny on LinkedIn!Follow Kenny on IG The Profit Power of Hospitality: Maximize Your ROI by Elevating Guest Experiences with Superior Hospitality (Part 2)

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:Why adding an inspector role can make or break your guest reviewsHow personal touches can create memorable experiencesThe importance of tracking historical data to consistently improve your revenueWhy raising your nightly rate strategically can increase profits in the long runHow guest feedback can help you rebrand your property for even better resultsThe role of patience and testing in setting competitive pricesWhy paying attention to details, like presentation and communication, is crucial for guest satisfaction.And much more…Resources:Thanksforvisiting.comThanksforVisiting Instagram PageThanksForVisiting Youtube Channel Connect with Kenny on LinkedInFollow Kenny on IG

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:Why hospitality is crucial, but often overlooked in the world of short-term rentals.The need for sustained and replicable hospitality that can be automated.Why hosts should stay in their properties for at least two nights to understand the guest experience.The importance of having the right teams in place to maintain and enhance hospitality in short-term rentals.And much more...

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:The origin of Launch Host's mission: to help property owners get their money back quickly by setting up their properties within seven days.The importance of sticking to performance timelines, budgets, and ensuring quality work.The value of engaging an STR-specific designer who understands tight turnaround times and delivery dates.Why treating the installation process as a full-time job and managing emotions and energy levels can prevent burnout.And much more...Resources:Launched HostLaunched Host Facebook

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:The importance of launching a property quickly to minimize holding costs and maximize cash flow.The relevance of having a plan in place before starting the design process.The significance of surrounding oneself with experts who can complete tasks faster.The challenges of replacing furniture and making renovations within a tight timeframe.And much more...Resources:Connect with Kenny on LinkedIn!Follow Kenny on IGDisclaimer: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.

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.https://intellihost.co/Connect with Kenny on LinkedIn!Follow Kenny on IG

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.Connect with Kenny on LinkedIn!Follow Kenny on IG

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.Connect with Kenny on LinkedIn!Follow Kenny on IG

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.Connect with Kenny on LinkedIn!Follow Kenny on IG

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.https://strscalesummit.com/Connect with Kenny on LinkedIn!Follow Kenny on IG

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.https://strscalesummit.com/Connect with Kenny on LinkedIn!Follow Kenny on IG

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.https://strscalesummit.com/Connect with Kenny on LinkedIn!Follow Kenny on IG

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.https://strscalesummit.com/Connect with Kenny on LinkedIn!Follow Kenny on IG

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.https://strscalesummit.com/Connect with Kenny on LinkedIn!Follow Kenny on IG

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.https://strscalesummit.com/Connect with Kenny on LinkedIn!Follow Kenny on IG

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.https://strscalesummit.com/Connect with Kenny on LinkedIn!Follow Kenny on IG

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.https://strscalesummit.com/Connect with Kenny on LinkedIn!Follow Kenny on IG

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.https://strscalesummit.com/Connect with Kenny on LinkedIn!Follow Kenny on IG

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.https://strscalesummit.com/Connect with Kenny on LinkedIn!Follow Kenny on IG

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.https://strscalesummit.com/Connect with Kenny on LinkedIn!Follow Kenny on IG

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.https://strscalesummit.com/https://www.strinsights.com/Connect with Kenny on LinkedIn!Follow Kenny on IG

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.https://strscalesummit.com/Connect with Kenny on LinkedIn!Follow Kenny on IG

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.https://strscalesummit.com/Connect with Kenny on LinkedIn!Follow Kenny on IG

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)-210-4205Connect with Brian on LinkedInConnect with Kenny on LinkedIn!Follow Kenny on IG

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!Connect with Kenny on LinkedIn!Follow Kenny on IG

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. Follow Patryk on IGConnect with Kenny on LinkedIn!Follow Kenny on IG

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. Connect with Kenny on LinkedIn!Follow Kenny on IG

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.Follow Tyler on IGConnect with Tyler on LinkedInConnect with Kenny on LinkedIn!Follow Kenny on IG

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!Connect with Kenny on LinkedIn!Follow Kenny on IG

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.Connect with Kenny on LinkedIn!Follow Kenny on IGConnect with Brenna on IG!

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! Connect with Kenny on LinkedIn!

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 Matt on IG!Connect with Kenny on LinkedIn!