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...

In this episode of the Cashflow 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...

In this episode of the Cashflow 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...

In this episode of the Cashflow 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...

In this episode of the Cashflow 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...

In this episode of the Cashflow 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...

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 for both novice and seasoned investors, Kenny sets the stage for understanding the foundational principles of budget planning and investment readiness, ensuring you’re not just investing, but doing so wisely.  

Kenny will introduce two crucial concepts: bankability and affordability. These serve as guiding pillars for determining your financial limits and leveraging your resources effectively. From understanding what lenders evaluate when approving loans to ensuring you have sufficient capital for property improvements, Kenny will walk you through actionable steps to maximize their purchasing power. 

Whether you're starting small with a one-bedroom rental or scaling to larger, high-revenue properties, Kenny offers a balanced perspective on the time, effort, and financial outcomes involved.

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:

• The two critical factors when starting your short-term rental investment journey.
• Why setting aside at least 20% of a property's purchase price for furnishings, design, decor, and amenities is essential.
• The benefits of scaling from smaller properties to larger ones, and why bigger properties can generate higher cash flow while requiring similar time investment.  
• How to align your investment strategy with your financial and career situation, ensuring the time and effort spent on property investments are worthwhile.
• And much more...

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 maintaining a position of strength. 

Discover the emotional and psychological aspects of negotiation, as Kenny and Rachel touch on the influence of external factors such as agents' motivations and market pressure. The discussion also explores the critical role of making informed decisions from the outset and how proper preparation can lead to long-term success.

This episode brings insight into how minor adjustments in approach can unlock larger opportunities and avoid costly missteps, all while maintaining a disciplined focus on the bigger picture.

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:

• The importance of data and analytics in achieving cash flow positivity. 
• Why Rachel prefers short-term rentals over mid-term rentals due to their flexibility and market conditions.
• The BRRR strategy: buying a property, rehabbing it, renting it out, and refinancing it. 
• The role of relationships in securing better loan terms and the importance of having a track record with lenders.
• And much more...

Resources:

STR Insights

Rachel's LinkedIn

Connect with Kenny on LinkedIn

Follow Kenny on Instagram

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 upfront investment.

Kenny emphasizes the importance of focusing on undervalued properties, forcing appreciation, and approaching investments as a real estate investor first and a hospitality provider second. From leveraging seller credits to mastering the BRRRR strategy, this episode is packed with practical tips to help you find deals that cash flow without breaking the bank.

Whether you’re new to STRs or looking to scale your portfolio on a budget, this episode offers the insights you need to take action and start building wealth. Enjoy!

In This Episode You'll Learn:

• Why undervalued properties with “good bones” are your best bet for ROI
• How to leverage the BRRRR strategy to scale your STR portfolio
• The importance of combining real estate investment principles with hospitality goals
• Why you need to avoid buying properties based purely on revenue speculation
• How to stay scrappy and find financing solutions that work for you
• And much more…

Resources:

Connect with Kenny on LinkedIn

Follow Kenny on Instagram

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 dives into the transformative power of systems and automation for property managers.

The conversation covers the journey of Can Monkey from a small idea to a multi-state operation, serving thousands of properties. Alex and Kenny discuss how streamlined services like trash handling can save time, improve guest experiences, and build trust within neighborhoods.

Whether you’re managing one property or an entire portfolio, this episode provides insights into the value of consistency, automation, and being a good neighbor in your STR business.Enjoy!

In This Episode You'll Learn:

• Why consistency is the cornerstone of good STR management
• How automated services like Can Monkey help STR owners maintain harmony with neighbors
• The value of systems in streamlining operations and saving time
• How addressing overlooked tasks like trash management can significantly enhance guest experiences
• Tips for scaling your business while staying connected to community needs
• And much more…

Resources:

CanMonkey.com 

Connect with Alex on LinkedIn

Connect with Kenny on LinkedIn

Follow Kenny on Instagram