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...

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, buil...

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...

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...

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 a...

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 a...

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...

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,...

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 op...

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, amen...

In this episode of the Cash Flow Positive podcast, Kenny dives deep into the art of making smart investment decisions, particularly for those eyeing the short-term rental market.  You'll discover the importance of preparation and strategy, and why simply following the herd into trending markets without considering their unique financial circumstances should be avoided. With insights tailored...

In this episode of the Cash Flow  Positive podcast, Kenny is joined by Rachel Gniady, STR consultant with STR Insights. During the conversation, they discuss strategic decisions in a competitive market, particularly in real estate. You'll learn how to leverage knowledge and timing when approaching a potential deal, emphasizing the importance of understanding the broader market context and mai...

What’s the best way to find high ROI short-term rental deals when you’re short on funds? In this solo episode of Cash Flow Positive, Kenny Bedwell shares actionable strategies to uncover lucrative STR opportunities with little to no money down. Drawing on his own experiences, Kenny discusses creative approaches to deal structuring, financing options, and how to maximize returns while minimizing up...

What role does consistency play in being a great neighbor in the short-term rental world? In this episode of Cash Flow Positive, Kenny Bedwell welcomes Alex Shapiro, co-founder of Can Monkey, to discuss how this innovative service simplifies one of the biggest headaches for STR owners: trash management. From keeping properties clean and communities happy to ensuring neighbors are stress-free, Alex...

What does it truly mean to be a good neighbor in the short-term rental industry? In this solo episode of Cash Flow Positive, host Kenny Bedwell explores the key principles of being a responsible and engaged STR owner. From fostering positive relationships with neighbors to actively participating in your local and online communities, Kenny shares actionable insights to help you build a sustainable...

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 a...

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 operato...

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. Sh...

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...

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 esta...

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 emphasize...

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 t...

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...

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-wor...

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 effecti...