Cash Flow Positive

What do you do when you buy a short-term rental, and it just doesn’t perform?

In today’s episode of the Cash Flow Positive Podcast, Kenny Bedwell welcomes Erik Courson, an STR investor, tech enthusiast, and data-driven host, to share the honest story of how he bought a property at the peak of the market—and what he did when it started bleeding cash. In this open, numbers-first conversation, Erik walks us through the decisions that led to the purchase, the surprises he encountered, and the strategies that helped him go from a projected $30K loss to breakeven performance.

From redesigning a forgettable cabin in Blue Ridge, Georgia, to implementing revenue management tools and facing hard truths about sunk costs and missed expectations, Erik lays out what really works when you're trying to fix a less-than-ideal deal. He also reflects on the emotional toll of managing underperformance, the benefits of holding vs. selling, and why STR investors should embrace humility and adaptation.

If you've enjoyed this episode of the Cash Flow Positive podcast, be sure to leave a review and subscribe today! Listen now and enjoy!

In This Episode You'll Learn:

• How Erik turned a projected $30K loss into breakeven performance
• What to do before deciding to sell an underperforming property
• Why “locking in your losses” is often the most expensive mistake
• How niche positioning and small design changes can drive bookings
• Why emotion and market timing can lead smart investors astray
• How to use technology and AI to spot blind spots and hidden issues
• What Erik learned from investing in two very different STR markets
• Why community, critique, and clarity matter more than quick wins
• And much more...

Resources:

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What do you do when a property isn’t performing—and how do you know if it’s time to cut your losses or hold tight and turn it around?

In today’s episode of the Cash Flow Positive Podcast, Kenny Bedwell offers a grounded, practical perspective on one of the toughest situations a real estate investor can face: owning a short-term rental that just isn’t working. Drawing from real-world examples and lessons learned from clients across the U.S., Kenny walks through the key questions to ask before rushing to sell, and the most common (and fixable) issues holding properties back.

You’ll learn why immediate selling is often premature, how to calculate the true value of tax savings and appreciation, and what steps to take to improve revenue without over-investing. Whether you're breaking even, losing a little, or just frustrated with underperformance, this episode is packed with insight to help you analyze, adjust, and move forward with confidence.

If you've enjoyed this episode of the Cash Flow Positive podcast, be sure to leave a review and subscribe today! Listen now and enjoy!

In This Episode You'll Learn:

• Why not all underperforming properties are “bad” investments
• How to avoid locking in unnecessary losses by selling too soon
• What to analyze before deciding to exit a property
• Why tax savings, equity paydown, and appreciation still matter
• The top 3 levers to increase STR revenue—and how to check them
• How to remove personal bias and get honest feedback on your property
• When it does make sense to sell—and how to do it strategically
• What seasoned investors know about failure and learning from mistakes
• And much more...

Resources:

Connect with Kenny on LinkedIn

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What happens when you take a massive design risk on a short-term rental—and it turns into your most profitable investment ever?

In today’s episode of the Cash Flow Positive podcast, Kenny Bedwell welcomes Ashley Guy, a short-term rental investor, mom of six, agent, coach, and creative powerhouse behind one of the most unique Airbnbs in the U.S. Ashley shares the full story behind her now-famous “kink cabin” in Gatlinburg, Tennessee—a bold, adult-themed STR that grosses six figures annually and books out months in advance.

Ashley reveals the challenges of designing a fully immersive, highly targeted guest experience—from sourcing custom furniture to marketing without relying on traditional channels. She also breaks down why most investors play it too safe, how to stand out in saturated markets like Gulf Shores, and what it really takes to create properties that command premium rates and loyal repeat guests.

If you've enjoyed this episode of the Cash Flow Positive podcast, be sure to leave a review and subscribe today! Listen now and enjoy!

In This Episode You'll Learn:

• Why the “kink cabin” idea was a strategic investment, not a gimmick
• How Ashley made over $80K net on a $333K cabin in just one year
• The power of immersive design and what most hosts miss
• How to turn judgment and taboo into brand loyalty and bookings
• Why niche STRs outperform copy-paste properties in saturated markets
• The role of guest avatars and how to truly design for them
• How Ashley scales her creativity across multiple markets and property types
• Why “commit and figure it out” is a mindset every STR investor needs
• And much more...

Resources:

Connect with Kenny on LinkedIn

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thefemmeinvestor.com 

Contact Ashley at [email protected] 

What makes a short-term rental not just good, but unforgettable—and why do the most unique properties often deliver the biggest returns?

In today’s episode of the Cash Flow Positive Podcast, Kenny Bedwell explores how creating wildly unique properties can lead to massive success in the short-term rental market. Instead of copying cookie-cutter designs, Kenny explains why the most profitable hosts think differently: they go all in on targeting a specific guest avatar and design unforgettable experiences that guests will remember—and rebook.

Drawing inspiration from the world’s most unique Airbnbs, Kenny shares the strategies behind selecting the right market, crafting experiences guests actually want, and making smart, strategic design choices. He also highlights the risks of generic, templated properties and why deep research, creativity, and bold execution separate the best rentals from the rest.

If you've enjoyed this episode of the Cash Flow Positive podcast, be sure to leave a review and subscribe today! Listen now and enjoy!

In This Episode You'll Learn:

• Why wildly unique short-term rentals often achieve the best returns
• How to identify and design for your specific guest avatar
• Why "selling an experience" matters more than adding more amenities
• How strategic, memorable features boost bookings and brand recognition
• The dangers of copy-paste designs—and how to avoid blending into the crowd
• Why standing out is critical in saturated rental markets
• How going “all in” with your property creates an undeniable competitive edge
• Why half-hearted design efforts cost more than they save
• And much more...

Resources:

Connect with Kenny on LinkedIn

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The Pumpkin Plan: A Simple Strategy to Grow a Remarkable Business in Any Field

Are you navigating real estate deals without fully understanding the risks—or worse, putting yourself in legal jeopardy?

In today’s episode of the Cash Flow Positive Podcast, Kenny Bedwell welcomes Parker Borofsky, an experienced investor and short-term rental lending expert, to unpack some of the hottest—and riskiest—topics in real estate today. From the realities of seller credits and subject-to deals to the right (and wrong) ways to use LLCs for property ownership, Parker shares real-world advice, practical examples, and key lending insights that every investor needs to hear.

If you've enjoyed this episode of the Cash Flow Positive podcast, be sure to leave a review and subscribe today! Listen now and enjoy!

In This Episode You'll Learn:

• Why improperly handling seller credits can put you at risk of mortgage fraud
• What most people misunderstand about subject-to deals—and why they’re risky
• The truth about transferring properties into LLCs (and when it’s allowed)
• Why changing title ownership doesn’t automatically trigger alarms with lenders
• How DSCR loans and non-QM loans actually work—and their hidden challenges
• Why working with knowledgeable lenders can protect you from costly mistakes
• How failing to strategize your debt-to-income ratio could limit your growth
• Why talking to the right lender early can open up more opportunities than you think
• And much more...

Resources:

Connect with Kenny on LinkedIn

Follow Kenny on Instagram

Wealth Builders Mortgage Group

Are you making investment moves that could unknowingly cross the line into mortgage fraud?

In today’s episode of the Cash Flow Positive Podcast, Kenny Bedwell breaks down some of the hottest (and riskiest) real estate strategies being pushed today—from seller credits to subject-to deals to buying properties under LLCs. Kenny reveals what’s truly legal, what’s risky, and what could get investors into serious trouble if not handled properly.

Packed with practical examples, actionable advice, and a no-nonsense breakdown of gray areas in real estate, this episode will help you stay compliant, protect your investments, and build a smarter portfolio.

If you've enjoyed this episode of the Cash Flow Positive podcast, be sure to leave a review and subscribe today! Listen now and enjoy!

In This Episode You'll Learn:

• Why improperly handling seller credits could land you in legal trouble
• What actually constitutes mortgage fraud—and how to avoid it
• The difference between seller concessions and seller credits
• Why working with the wrong agent can expose you to major risk
• How "subject-to" deals work—and why they’re riskier than they appear
• Why buying properties in LLCs doesn’t always offer the protection you think
• The smarter way to move a property into an LLC without hurting your financing
• How to set up a safe, compliant strategy when investing in gray areas
• And much more...

Resources:

Connect with Kenny on LinkedIn

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What if global economic decisions could reshape the future of your short-term rental investments?

In this solo episode of the Cash Flow Positive podcast, Kenny Bedwell dives deep into the ripple effects of tariffs, presidential policies, and tax changes—and how they’re likely to impact STR markets across the U.S.

Drawing on his economics background and personal real estate experience, Kenny breaks down the macroeconomic trends in simple, real-world terms. From potential shifts in consumer travel habits to the implications of bonus depreciation and fluctuating interest rates, this episode provides actionable insights for anyone looking to navigate today’s uncertain economic climate with strategy and confidence.

If you've enjoyed this episode of the Cash Flow Positive podcast, be sure to leave a review and subscribe today! Listen now and enjoy!

In This Episode You’ll Learn:

• Why macroeconomic changes don’t impact every STR market the same way
• How tariffs could influence STR demand in driving vs. flying destinations
• Why now might be a good time to invest in real estate (if you do it smart)
• What to expect from potential tax changes and bonus depreciation
• How to evaluate your STR’s position in the market to determine risk
• Why fear-based headlines might not apply to your unique situation
• The importance of buying with a strategy—and a moat
• How occupancy and ADR play different roles in your revenue story
• And much more...

Resources:

Connect with Kenny on LinkedIn

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What happens when your Airbnb guest sues you—and are you actually protected?

In this episode of Cash Flow Positive podcast, Kenny Bedwell invites tax attorney and strategic advisor Anthony Brister to share crucial insights into asset protection, estate planning, and insurance—especially for short-term rental (STR) investors.

Anthony, founder of the Brister Law Firm, breaks down the levels of legal and financial protection STR operators should consider, from forming the right kind of LLC to understanding when it makes sense to consider charging order protection entities, umbrella policies, or trusts.

Together, Kenny and Anthony dissect real-world strategies for STR investors looking to protect their assets while growing their portfolios the smart way. They also share stories—like Kenny’s own experience of being sued by a guest—that bring home the urgency of getting your protection and paperwork in place before problems arise.

If you've enjoyed this episode of the Cash Flow Positive podcast, be sure to leave a review and subscribe today! Listen now and enjoy!

In This Episode You'll Learn:

• Why setting up an LLC is not enough—and what formalities you must follow to actually be protected
• How to layer your protections over time as your STR portfolio grows
• What a revocable trust really protects—and why it's about more than just assets
• How the state where you form your LLC could make or break your legal shield
• The single most overlooked insurance mistake STR investors make
• What umbrella policies do (and don’t) cover in real-life lawsuits
• How to time a deed transfer to an LLC without raising red flags
• When it's worth considering advanced tools like family limited partnerships or irrevocable trusts
• Why asset protection is about planning ahead—not reacting too late
• And much more...

Resources:

Connect with Kenny on LinkedIn

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Brister Law Firm, PLLC 

What do you do when your Airbnb guest sues you—and the case drags on for years? In this solo episode of Cash Flow Positive, Kenny Bedwell shares the behind-the-scenes story of a lawsuit that caught him off guard, how he navigated the legal chaos, and the surprising truth about LLC protection and short-term rental insurance.

This isn’t just a cautionary tale—it’s a wake-up call for every real estate investor who thinks they’re safe behind an LLC. Kenny breaks down exactly what happened, why it matters, and how you can avoid the stress and financial risk that comes with unexpected accidents, lawsuits, and worst-case scenarios.

If you’re investing in STRs or planning to, this episode is essential listening. From legal layers to loss-of-income coverage, Kenny walks you through the lessons he learned the hard way—so you don’t have to.

If you've enjoyed this episode of the Cash Flow Positive podcast, be sure to leave a review and subscribe today! Listen now and enjoy!

In This Episode You'll Learn:

• Why your LLC might not protect you the way you think it does
• What to do immediately if a guest is injured at your property
• The most underrated mistake STR investors make about insurance
• How to assess the right coverage for your risk level and market
• Why loss-of-income coverage is non-negotiable in disaster-prone areas
• The tipping point when you should start building layered asset protection
• Why having a great attorney isn’t enough—they need to review your policies too
• And much more...

Resources:

Connect with Kenny on LinkedIn

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Are you truly ready to launch your next short-term rental—or are you overlooking the hidden costs that could derail your returns?

In this episode of Cash Flow Positive, Kenny Bedwell continues the conversation on hard-earned lessons from the field, offering raw and practical advice every STR investor should hear. This isn’t just theory—it’s a behind-the-scenes look at what really happens when properties take longer to launch, when holding costs spiral, and when “almost guest-ready” just isn’t good enough.

Drawing from his own projects, Kenny breaks down what many investors miss when budgeting for renovations, managing out-of-state setups, and relying too heavily on contractors without local oversight. He also digs deep into market conditions, sharing what he’s seeing as the industry matures, where opportunity still lies, and why having a “moat” around your investment is more crucial than ever.

If you've enjoyed this episode of the Cash Flow Positive podcast, be sure to leave a review and subscribe today! Listen now and enjoy!

In This Episode You'll Learn:

• Why having boots on the ground can make or break your STR setup
• What it really takes to get a property fully guest-ready—not just 90% there
• How to build a “moat” around your STR and avoid constant reinvestment battles
• When seller credits work—and when they’re just smoke and mirrors
• How to prepare for appraisal gaps and navigate unrealistic seller expectations
• Why you should test everything—including toilets and outlets—before launching
• What STR investors often overlook when assessing resale value
• How to avoid getting lured into overpriced “super properties”
• Why now might be a better time to buy than later this year
• What maturing markets mean for buyers, sellers, and long-term investors
• And much more...

Resources:

Connect with Kenny on LinkedIn

Follow Kenny on Instagram

STR Insights YouTube channel 

Part 1: Types of STR Markets No One is Talking About