Cash Flow Positive

Kenny Bedwell
  • 5.0 (68)
  • Entrepreneurship
  • Updated Semiweekly

Step into the world of Cash Flow Positive, where the secrets to short-term real estate success await. Join our host, Kenny Bedwell, each week as he unveils a treasure trove of strategies for identifying, acquiring, and scaling profitable rental deals. In Part 1, experience a whirlwind of knowledge in just 15 minutes, packed with actionable insights and proven techniques. Then, immerse yourself in captivating interviews lasting 20 to 45 minutes, featuring industry mavens who've mastered the very concepts you've learned. Whether you're a seasoned pro or just starting out, Cash Flow Positive is your roadmap to unlocking the full potential of your property portfolio. Don't miss your chance to thrive in the dynamic world of real estate investment – tune in now!

  1. 4d ago

    How Much Cash Do You Really Need to Buy an STR?

    How Much Cash Do You Really Need to Buy an STR?How much cash do you actually need to buy a short-term rental? It’s a question Kenny Bedwell gets all the time, and the answer has changed dramatically as the STR industry has become more competitive. In this episode of Cash Flow Positive, Kenny breaks down what it really takes to invest in a short-term rental today, why STRs have become a much more capital-intensive investment, and why having more money doesn't automatically mean you'll get better returns. From the five major components of an STR investment to the point where additional spending starts producing diminishing returns, Kenny explains how investors can think more logically about the amount of capital they put into a property. Key TakeawaysWhy STR investing has become a luxury-style investment that requires significantly more upfront capital than it did several years ago.The five things you need to budget for: down payment, closing costs, improvements, amenities, and furnishings.How the STR industry has changed since 2016, from relatively simple Airbnb setups to highly designed, amenity-driven properties.Why the rise in competition has increased the amount investors need to put into their properties to achieve strong returns.Why outdated STR advice can be misleading as the industry continues to evolve and professionalise.How different markets are at different stages of adoption and why that affects the level of investment required to compete.Why there isn't a secret market where you can invest almost nothing and still expect a great return.Kenny's personal benchmark of roughly $150,000 in available capital as a minimum starting point for investing seriously in an STR today.Why having around $200,000 can open up more options and make it easier to properly fund a property.Why roughly $300,000–$350,000 in available capital can create a different level of opportunity, particularly when competing for larger properties and better amenities.Why more capital doesn't mean you should spend all of it. Kenny explains how diminishing returns eventually kick in.The danger of overspending on design, furnishings, amenities, or expensive vendors simply because you have the money available.Why gross revenue can be a vanity metric and why investors need to look at what they're actually netting relative to the capital invested.Why occupancy isn't everything. Kenny shares an example of a property producing strong net income despite having only 46% occupancy.The difference between being fully booked and actually generating a strong ROI.Why investors need to find the balance between underinvesting and overspending.How to use the competition in your market to understand what level of investment is actually required.Why the goal isn't necessarily to create the most expensive property, but to create a property that produces a strong return on the capital invested. About the HostKenny 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. Important LinksSTR Insights: 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.

  2. Sep 24

    Stop Asking, “What’s the Best Airbnb Market?”

    Stop Asking Me What the Best STR Markets Are“What are the best markets to invest in?” It’s one of the most common questions Kenny Bedwell gets asked. But as the short-term rental industry has become more professional and competitive, that question has become much harder to answer. In this episode of Cash Flow Positive, Kenny explains why there is no single list of “best markets” that works for every investor. The right market depends on how much you can actually invest, what you're trying to achieve, and what type of market you're willing to operate in. Kenny breaks down how the professionalisation of the STR industry has changed the way investors should evaluate markets, why your budget can determine where you can realistically compete, and why personal preferences matter more than investors might think. Key TakeawaysWhy “What are the best markets?” is becoming the wrong question as the STR industry becomes more competitive and professionalised.How the STR market has evolved from simply choosing a popular market to identifying the right property and sub-market within it.Why your investment budget can determine which markets make sense for you.The five components of an STR budget: down payment, closing costs, improvements, amenities, and furnishings.Why stretching your budget can quickly become a problem when unexpected project costs start adding up.How diminishing returns can affect heavily invested properties and why spending more doesn't automatically mean earning a better return.Why you need enough capital to compete with the existing top properties in the market you're entering.How to research what competitors are actually spending by looking at newly launched properties, their amenities, design, furnishings, and overall level of investment.Why today's investment costs matter rather than relying on what properties may have cost before or during the COVID-era STR boom.Why your investment goals need to be specific, whether that's cash flow, cash-on-cash return, tax savings, or long-term wealth.Why “I want as much as possible” isn't a useful investment goal and how establishing a minimum acceptable return can make decisions clearer.Why your personal preferences matter when choosing a market.How personal biases about certain locations can cause investors to overlook opportunities.Why you need to be interested enough in a market to operate the property well, even if you're primarily investing for the numbers.Why the average property isn't necessarily the target when you're looking for strong STR returns.How defining your budget, goals, and preferences together can narrow down the markets that actually make sense for you.The three questions investors should ask instead: What's my budget? What are my ROI goals? What are my personal preferences? About the HostKenny 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. Important LinksSTR Insights: 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.

  3. Sep 17

    You don't need another amenity. You need a moat.

    Stop Adding Amenities. Build a Better Moat.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. Key TakeawaysWhy 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. About the HostKenny 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. Important LinksSTR 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.

  4. Sep 10

    Data Over Hype - What to Watch Out For

    Data Over Hype: How to Make Smarter STR Investment DecisionsAs 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. Key TakeawaysWhy 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. About the HostKenny 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. Important LinksSTR 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.

  5. Sep 3

    How the pros get deals done

    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. Key Takeaways• 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 About the HostKenny 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. Important LinksWant 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.

  6. Aug 25

    I stopped buying Airbnbs! Here's why

    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. Key Takeaways• 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 About the HostKenny 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. Important LinksWant 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.

  7. Aug 20

    The Foundations of Real Estate Investing

    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. Key Takeaways• 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 About the HostKenny 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. Important LinksWant 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.

  8. Aug 6

    Common Mistakes Investors Are Making in 2026

    Should Tax Savings Drive Your Next Airbnb Investment?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. Key TakeawaysWhy buying solely for tax savings can become an expensive mistakeHow to evaluate cash flow versus depreciation when comparing investment opportunitiesWhat "market saturation" really means and why it's often misunderstoodThe characteristics Kenny looks for when identifying promising markets in 2026How guest avatars and property differentiation create a competitive advantageWhy larger, experience-focused properties can outperform traditional vacation rentalsTax strategies that can improve cash flow throughout the year instead of waiting for a refundHow investors can avoid making rushed purchases before year-end deadlinesWhy diversification matters as real estate portfolios continue to growMarkets that may be regaining momentum after several years of heavy competition About the GuestRyan 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. Important LinksWant 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.

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5
out of 5
68 Ratings

About

Step into the world of Cash Flow Positive, where the secrets to short-term real estate success await. Join our host, Kenny Bedwell, each week as he unveils a treasure trove of strategies for identifying, acquiring, and scaling profitable rental deals. In Part 1, experience a whirlwind of knowledge in just 15 minutes, packed with actionable insights and proven techniques. Then, immerse yourself in captivating interviews lasting 20 to 45 minutes, featuring industry mavens who've mastered the very concepts you've learned. Whether you're a seasoned pro or just starting out, Cash Flow Positive is your roadmap to unlocking the full potential of your property portfolio. Don't miss your chance to thrive in the dynamic world of real estate investment – tune in now!

Information

  • Creator
    Kenny Bedwell
  • Years Active
    2024 - 2026
  • Episodes
    189
  • Rating
    Clean
  • Copyright
    © Kenny Bedwell
  • Show Website
    Cash Flow Positive

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