Cash Flow Positive

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:How to identify the right tasks to delegate to virtual assistantsWhy scaling your business starts with hiring the right teamThe mindset shift needed to lead effectively and build trustPractical steps to train VAs and set them up for successThe long-term benefits of freeing up your time to focus on growthAnd much more…Resources:Connect with Kenny on LinkedInFollow Kenny on InstagramBravoVirtualAssistants.com 

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:Avoid the trap of trading one job for another; focus on quality over quantityA CEO mindset is about prioritizing time and hiring the right team to scale effectivelyVirtual assistants can handle repetitive tasks, giving you time to focus on growthInvesting in people yields a higher time ROI, allowing for more freedom and balanceScaling a business requires surrounding yourself with individuals who support your visionAnd much more…Resources:Connect with Kenny on LinkedInFollow Kenny on InstagramSTRinsights.com 

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:A CEO mindset is about delegating, trusting others, and focusing on strategyEmpowering your team and sharing the rewards leads to mutual successSuccess starts with defining your vision and working towards your dream lifeCelebrate the wins, big or small, to stay motivated and inspiredGenerosity and collaboration can create a thriving business cultureAnd much more…Resources:Follow Julie on FacebookFollow Julie on InstagramConnect with Julie on LinkedInConnect with Kenny on LinkedInFollow Kenny on InstagramMilliondollarhost.com.au Julie’s Books:Million Dollar Host: Julie's Airbnb Portfolio Earned Over a Million Dollars In Her First Year...Yours can too! Hospitable Hosts: Inspiring & Memorable Stories From Airbnb Hosts Around The World To Educate & Motivate

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