Are creative financing deals the key to unlocking your next short-term rental, or could they lead you into financial trouble? In this episode of Cash Flow Positive, Kenny Bedwell is joined by seasoned real estate investor Brandon Thompson, who has flipped over 2,000 homes and built a diverse portfolio of short-term rentals, long-term rentals, and commercial properties over the past 21 years.

Together, they dive into the real truths behind creative financing in the STR space. Brandon shares his personal experiences with seller financing, Subject-To deals, and owner financing, shedding light on the risks investors often overlook when chasing low-interest deals. He also opens up about pivoting his own portfolio after market saturation and declining returns, and why being intentional with your investments is more important than ever.

If you’re weighing creative financing options or looking to scale your STR business without getting burned, this episode will arm you with practical advice from a veteran investor who’s seen it all. Enjoy!

In This Episode You'll Learn:

• Why creative financing isn’t a “one-size-fits-all” solution
• How to structure seller financing and Subject-To deals the right way
• The hidden risks behind “no money down” deals
• Why the glory days of STR investing are over—and how to adapt
• How to evaluate your return on equity and know when it’s time to pivot.
• The importance of finding the right market and avoiding oversaturated areas
• And much more…

Resources:

Connect with Kenny on LinkedIn

Follow Kenny on Instagram

Strwealthbrokers.com 

SouthernCharmVacay.com 

Connect with Brandon on LinkedIn

Follow Brandon on Facebook

In this episode of the Cash Flow Positive podcast, Kenny explores unconventional strategies that can open doors for those looking to make significant moves without following the traditional path.

These methods offer flexibility, allowing individuals to bypass common roadblocks while still creating valuable opportunities. However, while these approaches can be highly effective, they also come with unique risks and challenges that must be carefully navigated.  

You'll learn how these strategies benefit both parties involved, offering potential advantages that aren’t typically available in standard agreements. By understanding how to structure these arrangements wisely, individuals can maximize their potential while minimizing exposure to unnecessary pitfalls. At the same time, it’s crucial to be aware of the fine print—certain decisions could lead to unexpected consequences if not handled correctly.  

Whether you’re new to this approach or simply looking for ways to refine your strategy, this episode will provide valuable takeaways you won’t want to miss.

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:

• Creative financing for STRs, and how it allows direct negotiations with sellers, creating custom terms without the extensive paperwork required by banks.
• The concept of subject-to financing, where the seller assigns their mortgage to the buyer. 
• Owner financing, a method popular with sellers who don't need immediate cash and want to avoid taxable events from selling.
• The risks associated with creative financing, including the potential for banks to call the loan if they discover the deed change.
• And much more...

In this episode of the Cashflow 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...

In this episode of the Cashflow 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...

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 deal
• How to spot red flags in revenue projections before purchasing a property
• The difference between buying real estate vs. buying a business in STR investing
• Why knowing your market is the single most important factor in making smart investments
• The role of patience, persistence, and calculated risk in long-term success
• And much more…

Resources:

Connect with Kenny on LinkedIn

Follow Kenny on Instagram

In this episode of the Cashflow 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...

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 investors
• The challenges and opportunities of financing new construction short-term rentals
• How to balance risk tolerance and emotional decisions when purchasing properties
• Why running the numbers is critical to making smart investment decisions
• The importance of finding the right lender and understanding your financing options
• And much more…

Resources:

Connect with Kenny on LinkedIn

Follow Kenny on Instagram

Connect with Matt on LinkedIn

STRloanguy.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 financing
• How DSCR loans work and their unique advantages for STR investors
• Why understanding your debt-to-income ratio is crucial for financing decisions
• The importance of planning for long-term goals while choosing loan options
• Why you should always run your numbers and consult with a trusted lender
• And much more…

Resources:

Connect with Kenny on LinkedIn

Follow 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 goals
• How setting short-term, attainable goals builds the momentum needed for long-term success
• Why it’s more important to focus on the outcomes from your properties rather than the number of doors
• How to balance big, scary goals with achievable milestones to keep your confidence growing
• Why chasing money and comparing yourself to others can derail your progress
• And much more…

Resources:

Connect with Kenny on LinkedIn

Follow 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...