If your short-term rental isn't getting enough bookings, your first instinct might be to add something new. A pickleball court. A hot tub. An Xbox. An espresso machine. Whatever the competition seems to have.

But what if that's the wrong question?

In this episode of Cash Flow Positive, Kenny Bedwell breaks down why constantly adding amenities isn't necessarily going to make your property stand out. Instead, investors should focus on building a moat: something that creates a memorable experience and gives guests a reason to choose your property over the hundreds of other options available.

From better photography and guest experience photos to space, privacy, design, lighting, and making the most of what your property already has, Kenny explains how to think differently about standing out in an increasingly competitive STR market.

• Why adding more amenities isn't always the answer when a property is underperforming.
• The “keeping up with the Joneses” problem and why copying the amenities of successful properties can be misleading.
• Why you should ask “How can I stand out?” instead of “What am I missing?”
• How your property's layout can affect bookings, even when you technically have enough beds to accommodate more guests.
• Why short-term rental investing is ultimately a marketing race and how your listing needs to capture attention and emotion.
• How guest experience photos can elevate your listing and why models can be particularly valuable for higher-end properties.
• Why space and privacy are underrated selling points that should be highlighted in your marketing.
• The three types of amenities: those that primarily impact ADR, occupancy, or the guest experience.
• Why simply adding an amenity isn't enough if you aren't actually marketing it.
• What Kenny means by a “moat” and the different ways you can create one through design, location, views, water access, space, privacy, property type, or amenities.
• Why professional lighting can become a powerful moat by transforming the way a property looks and feels in photos.
• How one property used extensive professional lighting to stand out and become one of the top-performing properties in its market.
• Why the best moat isn't necessarily something nobody else can copy, but something that creates enough differentiation and effort that most competitors won't replicate it.
• How to elevate existing advantages, such as turning water access into a complete guest experience rather than simply adding kayaks or paddleboards.
• Why marketing is what activates your moat and turns a property's advantages into more bookings.
• How to identify your property's existing moat: ask why guests are choosing your property in the first place.
• Why checking boxes doesn't bring bookings unless those features are actually communicated and marketed effectively.

Kenny Bedwell is the host of Cash Flow Positive and an experienced short-term rental investor. Through the podcast, Kenny shares practical insights on real estate investing, short-term rentals, market data, cash flow, and the lessons he's learned from building and operating his own portfolio.

STR Insights: Want us to find the deals for you?

https://strinsights.com

STR Scale Summit: Join Kenny and 300+ serious STR investors in Louisville, Kentucky, March 3–5, 2027.

https://STRScaleSummit.com

Instagram: @kenny_bedwell

YouTube: Cash Flow Positive

LinkedIn: Kenneth Bedwell

Cash Flow Positive is an original podcast hosted by Kenny Bedwell.

As the short-term rental industry matures, competition is increasing not just among property owners, but among the vendors, influencers, services, and businesses built around the industry.

In this episode, Kenny Bedwell takes a closer look at what happens when markets stabilise and competition increases, and why that can lead to more hype, stronger sales pitches, and advice that isn't always backed by the numbers.

The key is learning to recognise the difference between genuine, data-backed insight and someone simply trying to sell you a particular market, strategy, service, or idea.

• Why STR vendor saturation is increasing as more businesses enter the industry to solve problems for hosts.
• What rising customer acquisition costs mean for vendors and why increasing competition can change how businesses market themselves.
• Why market saturation can create more hype as businesses and influencers look for new ways to attract customers.
• How to recognise when advice is based on data versus speculation.
• Why you should question claims about “the best markets” and ask where the supporting data actually comes from.
• How incentives can influence the advice you receive, particularly when someone benefits financially from your decision.
• Why you should never assume that spending more money on a property automatically means you'll make more money.
• The danger of confusing a successful outcome with a proven strategy, especially when someone may simply have gotten lucky.
• Why amenities don't produce identical results in every market, and why strategies need to be evaluated in the context of the individual property and market.
• A real-world example of using data to evaluate pools and increased revenue, rather than assuming a particular type of pool will work everywhere.
• Why investors should underwrite using what the market has actually proven, rather than projecting an unproven revenue ceiling.
• The importance of understanding the failures you don't hear about when evaluating success stories in the STR industry.
• How to ask better questions before making an investment: Why this market? Why this amenity? Where did the data come from? How does this benefit the person giving the advice?
• Why data-driven decisions should come before hype when you're investing significant amounts of your own money.

Kenny Bedwell is the host of Cash Flow Positive and an experienced short-term rental investor. Through the podcast, Kenny shares practical insights on real estate investing, short-term rentals, market data, cash flow, and the lessons he's learned from building and operating his own portfolio.

STR Insights: Want us to find the deals for you?

https://strinsights.com

STR Scale Summit: Join Kenny and more than 300 real estate investors in Louisville, Kentucky, March 3–5, 2027.

https://STRScaleSummit.com

Instagram: @kenny_bedwell

YouTube: Cash Flow Positive

LinkedIn: Kenneth Bedwell

Cash Flow Positive is an original podcast hosted by Kenny Bedwell.

How the Pros Get Real Estate Deals Done Faster

One of the biggest things holding real estate investors back isn't a lack of good deals. It's analysis paralysis.

In this episode, Kenny Bedwell breaks down how experienced investors approach offers differently and why making an offer doesn't have to mean making a hard commitment. Instead, the offer is the beginning of the due diligence process, giving you time to investigate the property, update your numbers, uncover potential issues, and decide whether the deal actually works.

Kenny explains how thinking about the buying process as a series of decisions, rather than one big commitment, can help investors move faster and avoid missing great opportunities. He also shares how experienced investors use multiple offers, buy box criteria, and concurrent due diligence to speed up their acquisition process when deadlines demand it.

Plus, Kenny shares a real example of an investor who missed out on a strong cash-flowing property by asking for extensive due diligence before making an offer, while another buyer moved quickly, completed the research under contract, negotiated the price, and ultimately got the deal.

• Why making an offer is a soft commitment, not a hard commitment

• How due diligence gives investors time to properly evaluate a property

• Why trying to eliminate all risk before making an offer can cause you to miss great deals

• How experienced investors approach negotiations differently

• Why your deal analysis should remain fluid throughout the entire buying process

• The two levels of deal-making Kenny sees among experienced investors

• How making multiple offers can accelerate acquisitions when working against a deadline

• Why buy box criteria allow experienced investors to move quickly without acting recklessly

• How opportunity cost can make waiting for the "perfect" deal more expensive than taking action

• A real-world example of an investor who missed a 19% gross ROI property by waiting for too much information

• Why getting under contract can actually give you more negotiating leverage

• How treating real estate investing as a process rather than a one-time decision can make buying much easier

Kenny Bedwell is a short term rental investor, entrepreneur, and founder of STR Insights. Through Cash Flow Positive, he shares his experience building and operating high performing short term rentals while helping investors make smarter decisions about acquiring, operating, and growing their portfolios.

Want us to find the deals for you? https://strinsights.com

Instagram: @kenny_bedwell

YouTube: Cash Flow Positive

LinkedIn: Kenneth Bedwell

Cash Flow Positive is an original podcast hosted by Kenny Bedwell.

Why I’m Not Buying More Airbnbs Right Now

What if buying another Airbnb isn’t actually the best move for your portfolio?

In this episode, Kenny Bedwell explains why he has paused his Airbnb acquisitions after years of building and growing his short term rental portfolio. But that doesn’t mean he’s done buying Airbnbs. Instead, Kenny breaks down why successful investing is about knowing what your portfolio needs at each stage and making sure your next investment supports your bigger goals.

With several properties already generating significant cash flow, Kenny explains why he is shifting his focus toward stabilization and long term appreciation rather than simply adding another cash flowing property. He also shares how his 14 room hotel fits into that strategy and why the right investment can look completely different depending on where you are in life.

From knowing when to stop acquiring to understanding your exit strategy, this episode is about being intentional with your investments instead of constantly chasing the next deal.

If you're building a short term rental portfolio, this episode will help you step back, look at the bigger picture, and figure out what your next investment should actually accomplish.

• Why Kenny paused his Airbnb acquisitions after years of aggressive buying

• Why constantly chasing cash flow can eventually create another job

• How to know when it is time to stop acquiring and start stabilizing

• Why your investment goals should determine what you buy and when you buy it

• The difference between generating cash flow and building long term wealth

• Why appreciation becomes more important once you have enough cash flow

• How Kenny's hotel investment fits into his longer term wealth strategy

• Why your exit strategy should influence the markets and properties you choose

• Why operating and marketing your existing properties is just as important as finding new deals

• Why your investment plan needs to change as your life, goals, and circumstances change

Kenny Bedwell is a short term rental investor, entrepreneur, and founder of STR Insights. Through Cash Flow Positive, he shares his experience building and operating high performing short term rentals while helping investors make smarter decisions about acquiring, operating, and growing their portfolios.

Want us to find the deals for you? https://strinsights.com

Instagram: @kenny_bedwell

YouTube: Cash Flow Positive

LinkedIn: Kenneth Bedwell

Cash Flow Positive is an original podcast hosted by Kenny Bedwell.

What are the real foundations of a successful real estate investment?

There’s a lot of conflicting advice online about what matters most when investing in real estate. Some investors swear by cash flow, others chase appreciation, and others focus heavily on tax savings. But according to Kenny Bedwell, the answer isn’t as simple as picking one.

In this episode, Kenny goes back to the fundamentals and breaks down the four pillars of real estate investing: tax savings, cash flow, appreciation, and equity pay down. He explains why each one matters, how their importance changes depending on where you are in your investing journey, and why focusing too heavily on any single benefit can lead to a bad investment.

Kenny also breaks down the difference between speculative and calculated appreciation, why cash flow is better viewed as an accelerator rather than the foundation of a portfolio, and how combining cash flow with appreciation can help investors scale faster.

Plus, Kenny introduces a new segment called Random Internet Musings, where he takes real comments from online investors and breaks down what they get right, what they get wrong, and what the fundamentals actually tell us.

• The four pillars of real estate investing and how each one contributes to your overall return

• Why you shouldn't build an investment strategy around tax savings alone

• How your priorities should change as you move through different stages of investing

• The difference between natural appreciation, speculative appreciation, and forced appreciation

• Why your planned exit timeline changes how you should think about appreciation

• Why cash flow is an accelerator for building a portfolio rather than the entire foundation

• How combining cash flow and equity growth can help you scale faster

• Why buying at the top of a market and hoping for appreciation can be a risky strategy

• How to think about cash flow, appreciation, and tax savings when evaluating a deal

• Kenny's take on the common advice that cash flow makes you an investor, appreciation makes you a speculator, and tax benefits make you an idiot

Kenny Bedwell is a short term rental investor, entrepreneur, and founder of STR Insights. Through Cash Flow Positive, he shares his experience building and operating high performing short term rentals while helping investors make smarter decisions about acquiring, operating, and growing their portfolios.

Want us to find the deals for you? https://strinsights.com

Instagram: @kenny_bedwell

YouTube: Cash Flow Positive

LinkedIn: Kenneth Bedwell

Cash Flow Positive is an original podcast hosted by Kenny Bedwell.

With bonus depreciation back at 100%, many investors are once again rushing into short-term rentals to reduce their tax bills. But is chasing tax savings enough to make a property a good investment?

In this episode, Kenny Bedwell and Ryan Bakke, CPA, discuss how investor behavior has changed since the return of full bonus depreciation. They explain why cash flow should always come before tax benefits, how to identify markets with long-term potential, and the biggest mistakes investors make when buying under year-end pressure.

Whether you're purchasing your first short-term rental or adding to an existing portfolio, this conversation offers practical strategies for making smarter investment decisions that build wealth beyond tax season.

• Why buying solely for tax savings can become an expensive mistake
• How to evaluate cash flow versus depreciation when comparing investment opportunities
• What "market saturation" really means and why it's often misunderstood
• The characteristics Kenny looks for when identifying promising markets in 2026
• How guest avatars and property differentiation create a competitive advantage
• Why larger, experience-focused properties can outperform traditional vacation rentals
• Tax strategies that can improve cash flow throughout the year instead of waiting for a refund
• How investors can avoid making rushed purchases before year-end deadlines
• Why diversification matters as real estate portfolios continue to grow
• Markets that may be regaining momentum after several years of heavy competition

Ryan Bakke is a CPA and real estate tax strategist who helps investors maximize tax efficiency while building profitable real estate portfolios. Through his accounting firm and educational platform, he specializes in bonus depreciation, cost segregation, retirement tax strategies, and long-term wealth planning for real estate investors.

Want us to find the deals for you?

https://strinsights.com

Instagram: @kenny_bedwell

YouTube: Cash Flow Positive

LinkedIn: Kenneth Bedwell

Guest Instagram: @ryanbakkecpa

Ryan's Community: https://www.skool.com/taxes

Cash Flow Positive is an original podcast hosted by Kenny Bedwell. Production and editing by Podcast Your Brand.

How do you grow an Airbnb from barely breaking even to one of the most wish listed properties in your state?

Janelle Gallucci joins Kenny Bedwell to share how she transformed a struggling Lake Tahoe Airbnb into one of the highest performing properties in Nevada. Starting with a property that barely covered its mortgage, she reveals the strategies that helped grow annual revenue from $25,000 to $165,000 while many hosts in competitive markets watched their earnings decline.

From identifying the right guest avatar to creating memorable experiences for families and pets, Janelle explains why thoughtful hospitality consistently beats chasing the latest trends. She also shares the operational systems, marketing strategies, and guest touches that helped her property become the most wish listed Airbnb in Nevada.

If you've ever wondered whether your current property still has room to grow, this episode offers practical strategies you can apply to create better guest experiences, increase revenue, and stand out in any market.

02:45 How Janelle grew one property from $25,000 to $165,000 in annual revenue

08:42 Why firing the property manager completely changed the business

15:07 The biggest mistake new hosts make when designing their property

20:54 How defining one guest avatar transformed bookings

26:38 The family friendly and pet friendly upgrades that guests love

36:15 Creating premium pet experiences that justify higher fees

44:20 The welcome basket strategy that generates five star reviews

53:12 Why amenities create experiences instead of filling space

59:46 Building a direct booking strategy that actually works

1:07:18 Why optimizing one property can outperform buying another

Janelle Gallucci is a short term rental investor, educator, and co founder of Seven Summers Host Academy. After leaving a successful career in tech sales, she now helps Airbnb hosts increase revenue through hospitality, branding, and operational excellence. Her Lake Tahoe property became the most wish listed Airbnb in Nevada while consistently increasing revenue in one of the country's most competitive vacation rental markets.

Want us to find the deals for you? https://strinsights.com

Instagram: @kenny_bedwell

YouTube: Cash Flow Positive

LinkedIn: Kenneth Bedwell

Guest Instagram: @sevensummershostacademy

Property Instagram: @thetahoehouse

Cash Flow Positive is an original podcast hosted by Kenny Bedwell. Production and editing by Podcast Your Brand.

What does it actually take to become one of the highest earning Airbnb properties in your market?

In this episode, Kenny Bedwell shares the strategies behind one of Kentucky's top performing short term rentals and explains why success is about much more than adding expensive amenities. From choosing the right market to understanding exactly who your property is designed for, he walks through the framework that has helped his properties consistently outperform the competition.

You'll learn why patience matters more than most hosts realize, how to evaluate a market before investing, and why the best properties are built around a specific guest instead of trying to appeal to everyone.

If you want to increase revenue, stand out in your market, and create a property guests remember, this episode is packed with practical lessons you can apply.

00:00 Why becoming a top performing property starts with the right strategy

02:10 The numbers behind one of Kentucky's highest earning short term rentals

05:08 Why your second year is often your most important

08:44 How investing more than your competition can create an advantage

13:15 When spending more stops producing better returns

17:02 How to find markets where you can stand out

22:10 Why many hosts struggle to keep up with changing guest expectations

28:06 How knowing your ideal guest influences every decision

33:08 The marketing mistake that causes properties to blend in

37:15 Four lessons every host can use to build a stronger business

Kenny Bedwell is a short term rental investor, educator, and founder of STR Insights. He owns and operates vacation rentals across the United States, including one of the highest earning properties in Kentucky. Through Cash Flow Positive, he shares practical strategies that help investors increase revenue, improve the guest experience, and build stronger hospitality businesses.

STR Insights

Airbnb

VRBO

Booking.com

Kentucky Bourbon Trail

Want us to find the deals for you? https://strinsights.com

Instagram: @kenny_bedwell

YouTube: Cash Flow Positive

LinkedIn: Kenneth Bedwell

Cash Flow Positive is an original podcast hosted by Kenny Bedwell. Brought to you by STR Insights.