With the short-term rental market evolving rapidly, simply following the old playbook won’t cut it anymore. In this episode of Cash Flow Positive, Kenny Bedwell breaks down what the future of STR investing really looks like—and it’s not for the faint of heart. From industry-wide professionalization to a rising demand for uniqueness, he outlines what successful hosts need to know (and do) to stay competitive.

Kenny shares his insights into how STRs are becoming more commercial and why that calls for more strategic, long-term investment thinking. This episode is a deep dive into shifting your mindset to hospitality professional—and building properties that people will rave about.

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 STR investing today requires a different approach than even a few years ago
• How the industry is becoming more commercial and what that means for hosts
• Why five-star reviews are no longer the gold standard—repeat guests are
• How to build properties that can’t be easily replicated
• What “stacking amenities” really means—and how to do it well
• The importance of targeting your ideal guest with intentional design
• Why your cash-on-hand matters more than your lender’s pre-approval
• How to create a STR investment that will stand the test of time
• And much more...

Resources:

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Disclaimer: 

The views, information, or opinions expressed during this podcast are solely those of the individuals involved and do not necessarily represent those of the Cash Flow Positive podcast or its affiliates. The content provided is for informational and entertainment purposes only and is not intended to be a substitute for professional advice. We make no representations as to the accuracy, completeness, suitability, or validity of any information on this podcast and will not be liable for any errors, omissions, or delays in this information or any losses, injuries, or damages arising from its display or use. Listeners should consult with a professional for specific advice tailored to their situation. By accessing this podcast, you acknowledge that any reliance on the content is at your own risk.

How do you know your short-term rental is actually legal, and not one neighbor complaint away from a lawsuit?

In today’s episode of the Cash Flow Positive podcast, Kenny Bedwell is joined by Katie Johnson, a real estate attorney and investor, to break down one of the most misunderstood legal threats in the short-term rental world: deed restrictions. Whether you're operating in Michigan or buying in Texas, these buried clauses in your title documents could override local STR-friendly zoning and put your entire business at risk.

Katie explains the difference between deed restrictions and HOA rules, why “residential use only” language matters, how to spot red flags in your title work, and the limited defenses available if a neighbor sues. They also discuss what title insurance really covers, when to bring in an attorney, and how to protect yourself before closing.

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:

• What deed restrictions actually are, and how they differ from zoning laws
• Why a city permit doesn’t protect you from private enforcement
• How to find and interpret deed restrictions in your title work
• What to do if you discover a restriction after closing
• Why Katie always requests title work on day one of due diligence
• How to use contingencies to protect your deal before it’s too late
• Why talking to your neighbors might save your investment
• The real risks of buying in unregulated STR markets
• And much more...

Guest Bio:       

Katie Johnson is a real estate attorney, investor, and founder of Katie Johnson, PLC, a Michigan-based law firm specializing in real estate and business law. She’s licensed in Michigan and Illinois, with a pending license in Indiana, and works closely with investors and short-term rental operators on everything from contract review to regulatory strategy. Known for her practical, investor-minded approach, Katie also speaks at conferences across the country and is an advocate for proactive legal planning in real estate. Her goal is to help property owners navigate regulations with confidence and clarity—before it’s too late.

Resources:

KatieJohnsonPLC.com 

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Just because you have a permit doesn’t mean your short-term rental is actually legal.

In today’s episode of the Cash Flow Positive podcast, Kenny Bedwell shares a real-life cautionary tale that every STR operator needs to hear. After working with a client who discovered a deed restriction after closing on a property, Kenny breaks down how these restrictions work, why title companies won’t protect you, and how neighbor relationships can make or break your rental’s future.

But this episode isn’t just about legal definitions—it’s about prevention, strategy, and people. Kenny dives into what you should do before you buy, how to read the fine print, and most importantly, how to build lasting trust with neighbors who have the power to shut you down.

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:

• What deed restrictions are and why they matter more than zoning
• Why title companies don’t flag every STR risk in advance
• How a neighbor lawsuit can override your city permit
• What to ask for in your title documents before closing
• How to talk to neighbors before and after you purchase
• Why good relationships can protect you from legal trouble
• How to turn STR-haters into direct booking allies
• The mindset that keeps your business safe—and your neighbors happy
• And much more...

Resources:

Connect with Kenny on LinkedIn

Follow Kenny on Instagram

What does it take to turn a direct booking website into a real revenue driver?

In today’s episode of the Cash Flow Positive Podcast, Kenny Bedwell is joined by Gil Chan, tech founder, short-term rental host, and the creator of CraftedStays—a platform that helps STR hosts easily build customizable direct booking sites without breaking the bank.

Drawing on his background in e-commerce, Gil walks through the parallels between retail and hospitality, explains how to structure a site that actually converts, and shares his strategies for guest vetting, trust-building, and long-term nurture campaigns. He breaks down what most hosts get wrong about direct bookings, and what to focus on instead—starting with knowing your ideal guest avatar and optimizing every piece of the guest journey around them.

From lead magnets and email flows to the psychology of brand visibility, this episode is packed with insights on how to grow your direct bookings sustainably—without trying to master every marketing channel at once.

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 e-commerce and STRs are more similar than you think
• What your direct booking site must include to build trust and convert visitors
• How to structure your site around your “guest avatar”
• What most STR owners misunderstand about branding and professionalism
• How to handle guest vetting on direct booking platforms
• Why starting small (with the right tools) beats outsourcing everything
• Gil’s favorite ways to collect and nurture guest emails automatically
• What a good year-one direct booking rate looks like—and how to scale it
• And much more...

Guest Bio:       

Gil Chan is a short-term rental host, tech entrepreneur, and founder of CraftedStays—a platform that makes it easy for hosts to build fully integrated, conversion-focused direct booking websites. With a background as a product director in e-commerce, Gil saw the gap between STR operators and the tech tools they needed to take control of their businesses. After building the first version of CraftedStays for his own properties, he left his six-figure job in tech to grow the company full-time. Today, Gil helps hosts across the U.S. build their brands, attract the right guests, and increase revenue—one click at a time.

Resources:

Connect with Kenny on LinkedIn

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Connect with Gil on LinkedIn

CraftedStays.co 

The Ultimate Guide to Direct Bookings

Booked Solid Podcast

Should you take direct bookings—and what does it take to make them work?

In today’s episode of the Cash Flow Positive podcast, Kenny Bedwell unpacks the real considerations behind building a direct booking strategy. While many hosts focus on software and site setup, Kenny zeroes in on the biggest challenge: attracting the right traffic. He explains how to create repeat business, leverage your property’s location, and build trust with potential guests—without relying on OTAs.

You’ll learn how to think in terms of guest journeys, content marketing, and simple tactics like email and signage to grow your brand over time. Whether you’re just starting to consider direct bookings or trying to make an existing strategy more effective, this episode offers clear, actionable guidance on how to do it right.

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:

• The top three concerns people have with direct booking sites
• How to identify and market to your “warm” and “cold” traffic segments
• Why repeat business is more powerful (and cheaper) than new traffic
• Simple ways to promote your brand inside your property
• How to use email and social to stay top-of-mind year-round
• Why promoting your market, not your property, builds trust
• How lead magnets and content marketing drive real results
• And much more...

Resources:

Connect with Kenny on LinkedIn

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Are you pricing your short-term rental based on facts—or just following what everyone else is doing?

In today’s episode of the Cash Flow Positive podcast, Kenny Bedwell sits down with Jake Cohen, founder of Step By Step BNB and a seasoned revenue manager overseeing 300+ listings. Together, they unpack the real strategies behind sustainable revenue, debunking myths and simplifying key concepts like RevPAR, booking windows, and market dynamics.

Jake breaks down the difference between pricing for high and low seasons, why most hosts underestimate the power of good photography, and what it really means to “be booked first” when it matters most. He also explains how to calculate and interpret RevPAR, set minimum night stays with intention, and use tools like PriceLabs to monitor real-time market behavior.

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 RevPAR is Jake’s #1 metric for STR health
• How to adjust your pricing based on seasonality and demand
• Why minimum night stays should change based on booking windows
• What most hosts get wrong about high vs. low season pricing
• How to calculate your property’s RevPAR (and why it matters)
• Why listing optimization is just as important as price strategy
• How to simplify your pricing—and book more with less effort
• And much more...

Resources:

Connect with Kenny on LinkedIn

Follow Kenny on Instagram

Step By Step BNB 

Price Your STR Facebook Group

What if the real problem with your revenue isn’t your price—it’s your mindset?

In today’s episode of the Cash Flow Positive podcast, Kenny Bedwell breaks down exactly why so many hosts struggle with pricing—and how to turn things around with consistent, proactive revenue management. From hiring a revenue manager to leveraging tools like PriceLabs, Kenny shares what works, what doesn’t, and why “just dropping your price” is the fastest way to lose control of your numbers.

You’ll hear why minimum night stays are a hidden lever, how to adjust to low-season buyer behavior, and why your average daily rate (ADR) and occupancy must be evaluated together. Kenny also talks about the “potato chip pricing strategy,” a simple analogy that can help you figure out where your property stands in the market—and how to price accordingly, without emotion or ego.

Whether you're overwhelmed by dynamic pricing or trying to recover from poor performance, this episode will give you the clarity and tools to make smarter pricing decisions going forward.

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 hiring a revenue manager might be the smartest investment
• How to stop reacting and start planning when bookings slow down
• Why “dropping prices” isn’t a strategy—it’s a symptom
• How to use minimum night stays to drive more bookings
• The difference between revenue, ADR, and occupancy—and why it matters
• How seasonality affects guest behavior and price sensitivity
• The mindset shift that separates consistent earners from frustrated hosts
• And much more...

Resources:

Connect with Kenny on LinkedIn

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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:

Connect with Kenny on LinkedIn

Follow Kenny on Instagram

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

Follow Kenny on Instagram

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]