Cash Flow Positive

Kenny Bedwell
  • 5.0 (69)
  • Entrepreneurship
  • 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. 2d ago

    Navigating the legal side of Airbnb's new terms and conditions

    Airbnb's New Rules: How to Protect Yourself Legally as a HostAirbnb's latest policy changes have short-term rental hosts asking some serious questions. While everyone seems focused on the new rules around guest chores, there's a much bigger issue that could put hosts at risk: restrictions on rental agreements and guest verification. In this episode of Cash Flow Positive, Kenny Bedwell sits down with Katie Johnson, an attorney and experienced short-term rental host, to break down what Airbnb's announced changes could mean for property owners and how hosts can protect themselves. From rental agreement exceptions and local occupancy laws to insurance coverage, LLCs, and property safety, Kenny and Katie discuss the legal protections every short-term rental investor should understand. Kenny also shares his own experience dealing with a guest injury lawsuit and why having the right safeguards in place matters long before something goes wrong. Whether you own one Airbnb or manage an entire portfolio, this episode offers practical steps to help you review your legal exposure, protect your investments, and prepare for changing platform policies. Key TakeawaysWhy Airbnb's rental agreement changes matter more than guest chores: Kenny and Katie explain why restrictions on rental agreements could create bigger problems for hosts than the widely discussed changes to checkout chores.Understanding the exceptions to Airbnb's new policy: Katie discusses circumstances where rental agreements may still be permitted, including legal requirements, HOA rules, qualifying amenities, and stays of 28 days or longer.When Airbnb's rules conflict with local occupancy laws: Platform policies don't override local regulations. Hosts still need to understand municipal occupancy limits, including restrictions on daytime visitors, to protect their permits and properties.Why rental agreements are an important layer of protection: Guest agreements can help establish expectations, communicate property rules, and discourage bookings from guests who don't intend to follow them.The four pillars of legal protection: Katie identifies rental agreements, insurance, LLCs, and property safety as the foundations of protecting a short-term rental business.Common insurance mistakes that leave hosts exposed: From failing to disclose short-term rental use to overlooking coverage for pools, hot tubs, and other amenities, Katie explains why reviewing your policy is essential.What Kenny learned from a real guest injury lawsuit: Kenny shares how a slip-and-fall claim involving one of his properties led to a legal dispute lasting several years, reinforcing the importance of insurance, documentation, and property safety.Why safety requirements shouldn't be overlooked: Smoke detectors, carbon monoxide detectors, handrails, pool signage, and other safety measures can help reduce the risk of injuries and legal claims.How hosts can respond to changing Airbnb policies: Rather than making rushed decisions, Katie encourages hosts to review applicable laws, understand their options, and establish clear procedures for guest agreements and verification.Why legal protection needs to evolve with your business: As short-term rentals become more professionalised and regulated, investors need to treat legal compliance and risk management as essential parts of operating a successful hospitality business. About the GuestKatie Johnson is a Michigan-based attorney and experienced short-term rental host who has been practising law since 2011 and hosting since 2015. After years of experience in both industries, Katie founded her own law firm focused on helping short-term rental owners protect their properties and businesses. She works with hosts on rental agreements, liability protection, insurance considerations, and legal compliance. Katie is also a speaker at the STR Scale Summit, where she shares her expertise on the legal side of short-term rental investing. About the HostKenny Bedwell is the host of Cash Flow Positive and founder of STR Insights, a data platform helping short-term rental investors make smarter, data-driven decisions. After replacing his W-2 income through successful short-term rental investments, Kenny has expanded his portfolio into long-term rentals and boutique hospitality. Through the podcast, he shares real investment experiences, lessons learned, and practical strategies for building sustainable wealth through real estate. Important LinksConnect with Katie Johnson: Instagram @strlaw.with.katie — DM “PODCAST” to request her free legal audit guide.Want us to find the deals for you? https://strinsights.comSTR Scale Summit: https://strscalesummit.comInstagram: @kenny_bedwellYouTube: Cash Flow PositiveLinkedIn: Kenneth Bedwell Cash Flow Positive is an original podcast hosted by Kenny Bedwell. Note: The episode discusses Airbnb policy changes announced at the time of recording. Hosts should verify the current platform terms and applicable local laws before acting on the legal options discussed.

  2. Oct 22

    I’m Buying Long-Term Rentals Again—Here’s Why

    Why would a successful short-term rental investor start buying long-term rentals again? In this episode of Cash Flow Positive, Kenny Bedwell shares why he's expanding his long-term rental portfolio, including a new quadplex under contract near Buffalo, New York, and how his investment strategy has evolved as his portfolio has grown. Kenny isn't walking away from short-term rentals. Instead, he's taking a more strategic approach to building wealth by balancing cash flow, appreciation, tax savings, and diversification. He breaks down the five reasons behind his decision, why owning more short-term rentals isn't always better, and how he's building a long-term rental portfolio with a specific exit strategy in mind. From stabilising existing properties to creating value through renovations, Kenny explains why the best investment isn't always the one generating the most cash flow today. Sometimes, it's the one positioning you for greater wealth five or ten years down the road. Key TakeawaysWhy diversification matters as your portfolio grows: Relying entirely on short-term rentals can expose investors to unexpected disruptions. Adding long-term rentals helps Kenny spread risk across different types of real estate investments.Cash flow builds income, but appreciation builds wealth: Kenny explains why he's taking profits from his short-term rentals and reinvesting them into properties with long-term appreciation potential rather than simply accumulating more cash flow.Quality over quantity in short-term rentals: Buying more properties isn't always the answer. Managing too many short-term rentals can become another full-time job, and spreading yourself too thin can hurt the guest experience and your returns.Why stabilising your portfolio is part of scaling: After acquiring five short-term rentals over three years, Kenny is focusing on improving operations, maintenance, amenities, and performance before expanding further.How long-term rentals fit into Kenny's tax strategy: Kenny discusses how his real estate professional status allows him to pursue tax benefits through cost segregation and depreciation on long-term rental properties, subject to the applicable tax rules.Why he's targeting properties with renovation potential: Rather than chasing immediate cash flow, Kenny is looking for undervalued properties where improvements can create genuine appreciation over a five-to-seven-year period.Building a portfolio with the exit in mind: Kenny shares his plan to acquire long-term rentals in a concentrated area near Buffalo, with the goal of potentially selling them together as a portfolio rather than individually.Why every property needs a purpose: Whether you're investing for income, tax savings, appreciation, or an eventual exit, Kenny explains why each acquisition should support a larger financial strategy. About the HostKenny Bedwell is the host of Cash Flow Positive and founder of STR Insights, a data platform helping short-term rental investors make smarter, data-driven decisions. After replacing his W-2 income through successful short-term rental investments, Kenny has continued expanding into long-term rentals and boutique hospitality. Through the podcast, he shares his experiences, lessons learned, and strategies for building sustainable wealth through real estate. Important LinksWant us to find the deals for you? https://strinsights.comSTR Scale Summit: https://strscalesummit.comInstagram: @kenny_bedwellYouTube: Cash Flow PositiveLinkedIn: Kenneth Bedwell Cash Flow Positive is an original podcast hosted by Kenny Bedwell.

  3. Oct 15

    How 7%+ interest rates change my investing strategy

    Interest Rates Are High. Should You Still Buy Short-Term Rentals?Higher interest rates are making short-term rental deals harder to find, but that doesn't mean opportunities have disappeared. In this episode of Cash Flow Positive, Kenny Bedwell breaks down how rising borrowing costs are affecting returns, why buying now and hoping to refinance later can be risky, and how investors can protect themselves by looking beyond cash flow alone. Kenny also explains the difference between real and fake forced appreciation, why improving a property's underlying residential value matters, and how the beginning of the year can create opportunities for investors willing to negotiate. Rather than sitting out the market because interest rates are high, learn how to evaluate individual deals, understand the risks, and adapt your strategy to the conditions in front of you. Key TakeawaysHow rising interest rates affect returns: Even a half-percentage-point increase can significantly reduce cash-on-cash returns and turn an attractive deal into a marginal one.Why you shouldn't rely on refinancing: Rates may eventually fall, but there's no guarantee of when. Buying a property that only works if you can refinance soon leaves you exposed if conditions don't improve.Why the deal matters more than the market: Instead of ruling out entire markets because of interest rates, focus on the numbers, the property's potential, and the risks involved.Cash flow isn't the whole picture: A property that depends entirely on rental income can become vulnerable when revenue drops unexpectedly. Having appreciation potential and multiple exit strategies provides more flexibility.Real vs. fake forced appreciation: Adding expensive short-term rental amenities doesn't necessarily increase a property's underlying residential value. Improvements such as adding bathrooms, increasing liveable square footage, and upgrading kitchens can offer more durable value.Think about your exit before you buy: Cash-out refinancing can increase debt and reduce cash flow. Consider what happens if revenue declines or you need to sell the property.Use seasonality to your advantage: January and February can present negotiation opportunities on properties that have been sitting on the market, although inventory may be more limited.Understand cause and effect: Higher interest rates can shrink the buyer pool and leave properties on the market longer. Investors who understand these dynamics can identify opportunities instead of automatically sitting out. About the HostKenny Bedwell is the host of Cash Flow Positive and founder of STR Insights, a data platform for short-term rental investors. Through data-driven investing and successful short-term rentals, Kenny has replaced his W-2 income with cash flow and shares practical insights to help other investors pursue similar financial freedom. Important LinksWant us to find the deals for you? https://strinsights.comInstagram: @kenny_bedwellYouTube: Cash Flow PositiveLinkedIn: Kenneth Bedwell Cash Flow Positive is an original podcast hosted by Kenny Bedwell.

  4. Oct 8

    I Bought a 14-Room Hotel. Here’s What I Wasn’t Prepared For

    I Bought a 14-Room Hotel: What I Wasn't Prepared ForKenny Bedwell finally has his 14-room boutique hotel in downtown New Orleans open to guests. But getting there was anything but simple. In this episode of Cash Flow Positive, Kenny pulls back the curtain on the project and shares the challenges, mistakes, delays, and unexpected lessons that came with buying and renovating a historic hotel in the Treme district, right across from the French Quarter. From navigating city permits and historic requirements to managing contractors, construction delays, holding costs, hotel operations, Wi-Fi infrastructure, guest safety, and the realities of running a property with staff, Kenny explains what he wasn't prepared for and what he would do differently next time. Key TakeawaysWhat it was really like buying and renovating a 14-room boutique hotel for $1.495 million and investing roughly $900,000 into the project.Why city permitting can become one of the biggest delays in a renovation project, particularly in historic areas.Why you can't completely hand off responsibility to your contractor. The person who cares most about the project is ultimately the person paying for it.How disconnected permitting and inspection processes created unexpected delays and additional work.Why you need to understand the entire approval process before construction begins, including what happens after the renovation is supposedly finished.The contractor lesson Kenny learned about incentives and deadlines, especially during the final stages of a large project.Why construction draw schedules can create an incentive problem when contractors have already received most of their payment but still have work left to finish.How bonuses and penalties could help keep contractors motivated and why Kenny plans to build clearer incentives into future renovation agreements.Why holding costs matter so much when a property isn't generating revenue yet. Kenny explains that the hotel was costing roughly $5,000 per week during the project.Why contracts need clear expectations, deadlines, responsibilities, and consequences before work begins.Why unexpected problems are inevitable during major renovations, especially when working on an old building.The importance of having both financial and mental preparation for construction surprises.Why a hotel is a completely different operational beast from a typical short-term rental.How a 14-room hotel can have more than 200 connected devices, making reliable Wi-Fi and connectivity critical to the guest experience and daily operation.Why hotel operations require much more planning and hands-on management, from staff and payroll to guest interactions and safety procedures.Why hotel guests and reviews create a different marketing challenge compared with operating an individual Airbnb.How hotel regulations can introduce requirements that STR investors may never encounter, including specific electrical and safety restrictions.Why anyone considering buying a hotel should study how to actually operate one, not just focus on the acquisition and potential revenue.The personal sacrifices involved in completing a major project, including Kenny's regular trips to New Orleans and the impact on his family and personal life.What Kenny learned about working with contractors, investors, partners, city officials, and local relationships.Why the project became a major personal growth experience, even beyond the financial and portfolio implications.The people who helped Kenny get the hotel across the finish line and why he credits the team rather than treating it as a solo accomplishment. 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 LinksLa Corte Hotel: Check out Kenny's 14-room boutique hotel in New Orleans. https://lacortehotel.com STR 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.

  5. Oct 1

    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.

  6. 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.

  7. 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.

  8. 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.

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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
    193
  • Rating
    Clean
  • Copyright
    © Kenny Bedwell
  • Show Website
    Cash Flow Positive

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