Cash Flow Positive

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:The challenges of managing properties near sports stadiums, such as the Buffalo Bills' stadium.Why Josh advises investors to focus on areas with established regulations and to work with experts who understand the local market.How small improvements, like adding a barrel sauna, can significantly increase revenue. The future of short-term rental investing in New York, taking into consideration new regulations and taxes.And much more...Resources:Connect with Kenny on LinkedInFollow Kenny on Instagram

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:The foremost concern people have about investing in blue states: regulations.Why some red states have strict regulations themselves against short-term rentals, such as Kentucky and Georgia.Kenny's personal preferences and reasons for not investing in California despite his positive outlook on blue states.The advantages of investing in highly regulated markets, such as lower competition and better protection.And much more...Resources:Connect with Kenny on LinkedInFollow Kenny on Instagram

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:Why investor expectations vs. reality can make or break a dealHow to spot red flags in revenue projections before purchasing a propertyThe difference between buying real estate vs. buying a business in STR investingWhy knowing your market is the single most important factor in making smart investmentsThe role of patience, persistence, and calculated risk in long-term successAnd much more…Resources:Connect with Kenny on LinkedInFollow Kenny on Instagram

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