Cash Flow Positive

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:The problem of misleading posts by realtors and influencers promoting certain investments. Kenny's approach of always looking for better deals and learning from each transaction. The importance of finding the right deals that will appreciate over time. Why you should be a real estate investor first and a short-term rental operator second.And much more...Resources:Connect with Kenny on LinkedInFollow Kenny on Instagram

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:Why DSCR loans are a game-changer for real estate investorsThe challenges and opportunities of financing new construction short-term rentalsHow to balance risk tolerance and emotional decisions when purchasing propertiesWhy running the numbers is critical to making smart investment decisionsThe importance of finding the right lender and understanding your financing optionsAnd much more…Resources:Connect with Kenny on LinkedInFollow Kenny on InstagramConnect with Matt on LinkedInSTRloanguy.com

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:The differences between commercial loans and conventional financingHow DSCR loans work and their unique advantages for STR investorsWhy understanding your debt-to-income ratio is crucial for financing decisionsThe importance of planning for long-term goals while choosing loan optionsWhy you should always run your numbers and consult with a trusted lenderAnd much more…Resources:Connect with Kenny on LinkedInFollow Kenny on Instagram

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:Why tracking progress is essential to staying on top of your short-term rental goalsHow setting short-term, attainable goals builds the momentum needed for long-term successWhy it’s more important to focus on the outcomes from your properties rather than the number of doorsHow to balance big, scary goals with achievable milestones to keep your confidence growingWhy chasing money and comparing yourself to others can derail your progressAnd much more…Resources:Connect with Kenny on LinkedInFollow Kenny on Instagram

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:Dr. Rachel's shift from traditional real estate strategies to short term rentals, focusing on the need for aggressive income rather than passive income. The practical aspects of the 2-door strategy, including its applicability for W2 earners and the importance of systems and operations. The importance of understanding the guest avatar and targeting markets that align with their needs and preferences.The benefits of having a support network and the importance of sharing knowledge and resources with others.And much more...Resources:Connect with Kenny on LinkedInFollow Kenny on Instagram

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:The regulatory risks in cities like Miami, Florida, and Las Vegas, Nevada. The high prices and low returns in the Emerald Coast, including Destin, Miramar Beach, and Panama City Beach.The regulatory and financial challenges in Oregon and Washington.The evolving market conditions in Asheville, North Carolina, as well as the significant investment needed to compete.And much more...Resources:Connect with Kenny on LinkedInFollow Kenny on Instagram

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:The confusion caused by various market lists and gurus who claim to know the best markets. The importance of having the right properties in the right markets, not just cool properties in the wrong areas. The value of finding markets where you don't have to constantly reinvest in the property to stay competitive.The challenge of competing against established resorts and hotels in high-demand markets. And much more...Resources:Connect with Kenny on LinkedInFollow Kenny on Instagram

In this episode of the Cash Flow Positive podcast, Kenny is joined by 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:The importance of working with an agent who understands short-term rentals (STRs).Insights into the Poconos real estate market, including why it's a competitive yet rewarding area for STR investments.Strategies for navigating multi-offer situations on highly desirable properties.Approaches to handling appraisal gaps and negotiating lower prices on properties that have been on the market for an extended period.And much more...Resources:Connect with Kenny on LinkedInFollow Kenny on Instagram

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:How to determine if a property is a logical deal before diving into negotiations and why understanding the market timing is crucial to making successful offers.  Creative strategies for leveraging agent commissions to close deals when buyer and seller expectations don’t align.  The importance of inspections in uncovering negotiation opportunities, including securing credits or repairs that can significantly reduce the final cost.  Why negotiation is a critical skill in real estate investing and how honing this ability can consistently lead to more favorable deals.And much more...Resources:Connect with Kenny on LinkedInFollow Kenny on Instagram

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:How understanding market affordability and property features can significantly impact real estate investment decisions.  Why seclusion, land, and unique amenities like pools are essential for maximizing property appeal and ROI.  How low competition and dynamic pricing strategies in areas like Berkeley Springs, West Virginia, create high-return opportunities for investors.  Why Geneva, Ohio, stands out as a top investment market due to its affordability, strong revenue growth, and untapped potential in property design and amenities.And much more...