Cash Flow Positive

Kenny Bedwell
  • 5.0 (66)
  • 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. 2d ago

    How to Leverage Other People's Money to Buy Deals

    What if the only thing standing between you and rapid portfolio growth isn’t money, but mindset and strategy? Kenny Bedwell drills into the raw realities of leveraging Other People’s Money (OPM) to explode your short-term rental business, exposing what actually works and what will quietly kill your progress. Whether you have time but no capital, or capital with no time, he details the only partnership structures that protect you, your investors, and your reputation in this cutthroat market. If you’re tired of inching forward one property at a time, this episode is your unfair advantage. Miss this, and you risk years of wasted effort or worse, destroyed trust. Listen now to claim your spot among the 5% who do deals with true confidence and never look back. This level of transparency and actionable detail is only here. Timestamped Highlights00:54 – The brutal reality of scaling fast with limited capital03:07 – Why asking for investor money scares most, and how to get over it06:16 – Top 20% status: Why simply owning ONE STR puts you way ahead09:19 – How investors decide who to trust (it’s not just about the deal)10:59 – The game-changing 3-part partnership framework revealed13:31 – The equity mistake 90% of new executors make16:43 – The unheard-of way to split tax savings and keep everyone happy18:54 – The critical conversation most partnerships skip (at their peril)20:28 – Why time or money isn’t your issue—your circle is Mentioned ResourcesAirbnb506B & 506C syndications“Analysis paralysis”Passive investing Important LinksWant us to find the deals for you? https://strinsights.com Get Top Markers for STRs (2025) - https://rebrand.ly/28b1df Instagram – @kenny_bedwellYouTube – Cash Flow PositiveLinkedIn – Kenneth Bedwell Cash Flow Positive is an original podcast hosted by Kenny Bedwell. Brought to you by STR Insights. Production and editing by Podcast Your Brand.

    23 min

  2. Jun 16

    3 Amenities That Transformed Our Revenue

    What if the three things holding back your short-term rental revenue are hiding in plain sight? Kenny Bedwell, data-driven investor and STR educator, breaks down the amenities most investors miss, ones that are scientifically proven to spike your bookings and cash flow fast. Forget the gimmicks and “guru” advice. In this brutally practical episode, you’ll hear real numbers, tactical breakdowns, and the overlooked upgrades that have delivered six-figure jumps for Kenny Bedwell and his clients. You will miss out on the bookings your comps are snatching up right now if you ignore these simple moves. Listen in and get the honest playbook for immediate results. No fluff. No hype. Just the uncommon upgrades that separate winning properties from the pack, only on Cash Flow Positive. Timestamped Highlights00:15 – The three revenue-slaying amenities every STR owner misses01:46 – Are you making this six-figure mistake with your amenities?04:39 – How a heated pool turned winter dead zones into year-round cash08:17 – Container pool case study. From $150K to $244K in a single year10:21 – The no-glamour upgrade that quietly adds $15K to your bottom line13:16 – Why full bathrooms are the untapped ROI secret in most markets20:08 – The lighting hack delivering 500 percent returns (not string lights)25:12 – One color tweak to your property lighting that boosts revenue 30 percent Mentioned ResourcesAirbnbChatGPT Important LinksWant us to find the deals for you? https://strinsights.com Get Top Markers for STRs (2025) - https://rebrand.ly/28b1df Instagram – @kenny_bedwellYouTube – Cash Flow PositiveLinkedIn – Kenneth Bedwell Cash Flow Positive is an original podcast hosted by Kenny Bedwell. Brought to you by STR Insights. Production and editing by Podcast Your Brand.

    30 min

  3. Jun 9

    Airbnb 2026 Summer Outlook

    Are you prepared for the Airbnb landscape to feel brutally different this summer? Kenny Bedwell, founder of STR Insights and numbers-driven host of Cash Flow Positive, pulls back the curtain on the truth behind short-term rental trends and the shifting power moves that will make or break your returns in 2026. In this hard-hitting episode, Kenny Bedwell reveals why stabilization is here, what “professionalization” actually means for hosts, and how oversaturation is crushing easy wins. You’ll hear the rare data and stories behind $10K bookings, competitive vendor wars, and why flashy isn’t always smart. Learn exactly where experienced investors are pivoting and what the herd of copycats is missing. Miss this episode, and you risk falling behind in the new normal leaving real profits and lasting success for someone else. Listen now for the brutal, numbers-first roadmap you won’t find in overhyped trend recaps. Timestamped Highlights00:18 – The subtle factor that will quietly decide who survives in STRs02:00 – A $10K summer booking that exposes the game-changing power of peak season04:29 – Why even expensive gas and rising costs are not slowing down travel demand06:24 – The unexpected data that proves market stabilization is here07:50 – Professionalization crushes returns for lazy investors (and creates opportunity)10:38 – The overlooked negotiating trick you should use with every vendor now12:36 – What most investors miss when evaluating their competition each summer16:08 – How “commercialized amenities” quietly future-proof your rental (with real examples)19:00 – Why tired strategies are failing and what separates investors with infinite returns21:30 – The costly mistake of chasing trends instead of compounding long-term value Mentioned ResourcesAirbnbCan MonkeyHost BuddySheratonMarriott Important LinksWant us to find the deals for you? https://strinsights.com Get Top Markers for STRs (2025) - https://rebrand.ly/28b1df Instagram – @kenny_bedwellYouTube – Cash Flow PositiveLinkedIn – Kenneth Bedwell Cash Flow Positive is an original podcast hosted by Kenny Bedwell. Brought to you by STR Insights. Production and editing by Podcast Your Brand.

    24 min

  4. May 26

    This Mistake Just Cost Me THOUSANDS

    Ever lost thousands simply by trusting the wrong process or the wrong person? Kenny Bedwell returns from a break not just with fresh life perspective but with the hard-won, painful truths of renovating an 1848 boutique hotel from hundreds of miles away. This episode dives deep into the exact mistakes that cost him actual cash, and even more valuable time from contractor sequencing chaos to shipments gone missing to why “project management by Zoom” is a surefire road to blown budgets. If you own or plan to own any STR, now’s the time to learn how to lead projects to the finish line without bleeding money. Skip this one, and you risk repeating the most expensive rookie mistakes in the book. Listen now for practical, brutally honest strategies you’re not getting anywhere else. Timestamped Highlights00:11 – The real cost of learning by fire on big renovation deals01:47 – The one-day trip that revealed everything broken about remote project management03:14 – Why showing up in person sparks a momentum shift with contractors05:25 – How a simple shipping oversight vanished $2,000 overnight06:10 – Where even pros screw up sequencing and lose weeks08:08 – The shocking truth about contractor incentives (and why they don’t care)09:25 – The proven fix that instantly cuts through project chaos12:10 – Why virtual management almost always leads to costly delays15:44 – Life-after-loss: Exact steps to prevent these disasters in your next STR project Mentioned ResourcesWayfair consolidated delivery serviceAmazon (referenced for shipping) Important LinksWant us to find the deals for you? https://strinsights.com Get Top Markers for STRs (2025) - https://rebrand.ly/28b1df Instagram – @kenny_bedwellYouTube – Cash Flow PositiveLinkedIn – Kenneth Bedwell Cash Flow Positive is an original podcast hosted by Kenny Bedwell. Brought to you by STR Insights. Production and editing by Podcast Your Brand.

    17 min

  5. May 5

    Two Secrets to Scaling a Successful Portfolio

    Are you stuck grinding but never really escaping? In this punchy solo episode, Kenny Bedwell drops the curtain on the two proven secrets that transformed his own portfolio, and he does not sugarcoat the realities. With sharp stories of scrappy beginnings, W2 frustration, and the gut-check moment that forced him to choose between comfort and growth, Kenny Bedwell dives deep into the real reasons investors stall out. Listen in if you’re ready to challenge the “just buy another unit” mentality, discover why time (not money) is your biggest bottleneck, and learn exactly what stops even high-income professionals from breaking through. Miss this episode and you’re gambling with years of wasted effort, stretching your goals into a never-arriving someday. Hit play now for straight answers you truly won’t find recycled elsewhere. Timestamped Highlights00:00 – What most investors get wrong about “scaling up”01:58 – The single conversation that shattered my old plan03:49 – The moment I made triple rent… and everything changed05:25 – The ugly reality of juggling W2, family, and side hustles08:23 – The corporate drama that forced my hand10:22 – Why time, not money, is your real shortcut to freedom14:42 – Why “bold” isn’t gambling and how I protect against disaster16:40 – The uncomfortable moves that led to explosive cash flow Mentioned ResourcesAirbnbBiggerPockets Important LinksWant us to find the deals for you? https://strinsights.com Get Top Markers for STRs (2025) - https://rebrand.ly/28b1df Instagram – @kenny_bedwellYouTube – Cash Flow PositiveLinkedIn – Kenneth Bedwell Cash Flow Positive is an original podcast hosted by Kenny Bedwell. Brought to you by STR Insights. Production and editing by Podcast Your Brand.

    24 min

  6. Apr 28

    Who Is ACTUALLY Booking Your Property?

    Are your short-term rentals sitting empty while your competitors rake in bookings? You might be targeting the wrong guest without even knowing it. In this tough-love, numbers-driven solo episode, Kenny Bedwell, founder of STR Insights, reveals the six REAL buyer personas that drive every booking decision and why most hosts get it dead wrong. Cut through the industry fluff: This episode breaks down how each persona thinks, what drives their decisions, and how seasonality radically shifts who you’re really marketing to. Whether you’re struggling to fill high-end properties, want to squeeze more out of the low season, or just avoid attracting guests who tank your reviews, this episode gives you direct, actionable insight you simply won’t find on other STR podcasts. Stop the guesswork. Listen right now to protect your cash flow, outsmart your competition, and attract the guests you actually want. These frameworks are exclusive, urgent, and can change your booking game overnight. Timestamped Highlights00:02 – Dad shirts are back… but is your STR guest strategy stuck in winter?00:44 – The secret reason you keep attracting the “wrong” guests (and how to fix it)03:03 – Why budget buyers will ignore your amenities—and the pricing trap most hosts fall into07:32 – Value seekers, Costco logic, and the most common STR buyer (are you missing easy profits here?)10:46 – The convenience persona: Why location, reviews, and guarantees can replace discounts13:17 – Experience seekers exposed: Social media-worthy guests—and the Instagram marketing mistake16:55 – Luxury buyer drama: When high expectations drive guests to cancel… and why “luxury” is more than just a word20:29 – Occasion seekers and the money left on the table when you ignore group dynamics Mentioned ResourcesAirbnb LuxeCostco, Sam’s Club, Dollar Tree (buyer mindset examples)Instagram (direct booking for experience stays)Marriott, Sheraton (hotel chains, buyer persona contrasts) Important LinksWant us to find the deals for you? https://strinsights.com Get Top Markers for STRs (2025) - https://rebrand.ly/28b1df Instagram – @kenny_bedwellYouTube – Cash Flow PositiveLinkedIn – Kenneth Bedwell Cash Flow Positive is an original podcast hosted by Kenny Bedwell. Brought to you by STR Insights. Production and editing by Podcast Your Brand.

    27 min

  7. Apr 21

    STR Vanity Metrics to Avoid

    Are you obsessed with high booking rates, glowing reviews, or six-figure revenue? What if those metrics are secretly keeping you broke and blind to your property’s true potential? In this punchy solo episode, Kenny Bedwell, founder of STR Insights and host of Cash Flow Positive, exposes the most overhyped “STR swear words” in the business, metrics that sound good but can destroy your bottom line if you chase them blindly. You’ll learn why occupancy rate, guest ratings, and even jaw-dropping gross revenue can cost you time, money, and deal flow if you don’t dig deeper. Don’t gamble your freedom or future on surface numbers. Listen now to dodge expensive pitfalls, outsmart the sharks, and finally see REAL cash flow. Miss this episode, and you’ll risk overpaying for duds nobody else wants to touch. Timestamped Highlights00:02 – The “STR swear words” that make Kenny Bedwell furious (and should make you nervous)02:26 – The real story behind high occupancy rates—why 100% bookings can be a trap04:24 – The 46% rule: How a “low” occupancy rate led to insane ROI (and less headaches)06:53 – The year-round bookings myth and why chasing monthly returns kills your annual gains08:00 – A 4.89-star rating, $60K more profit—what everyone gets wrong about reviews10:03 – Why high bookings and high ratings still don’t guarantee cash flow (and what to demand instead)13:23 – Gross revenue exposed: How sellers weaponize the most misleading metric in STR16:13 – $5K “brag posts” vs. $2K net: The social media profit illusion you must avoid Mentioned ResourcesVRBOAirbnbFacebookProfit & Loss statements (PNL)Booking Lead Time (industry trend)“Superhost” and Airbnb algorithm factors Important LinksWant us to find the deals for you? https://strinsights.comGet Top Markers for STRs (2025) - https://rebrand.ly/28b1dfInstagram – @kenny_bedwellYouTube – Cash Flow PositiveLinkedIn – Kenneth Bedwell Cash Flow Positive is an original podcast hosted by Kenny Bedwell. Brought to you by STR Insights. Production and editing by Podcast Your Brand.

    23 min

  8. Apr 18

    BIG NEWS: Airbnb listened to this podcast!

    Are your Airbnb profits slipping and you don’t know why? Imagine waking up to a revenue model change that could make or break your short-term rental business. In this urgent solo episode, Kenny Bedwell breaks open the truth behind Airbnb’s blockbuster reversal on host fees, the quiet switch nobody was supposed to notice, but every smart investor needs to understand today. You’ll discover what’s really behind the fee flip, how it impacts your property’s ranking and bookings, and exactly how to adapt before the window slams shut. Don’t let another booking cycle pass you by while others get ahead. If you care about maximizing profit and avoiding algorithm disaster, you need these exclusive, data-backed strategies right now. Only Cash Flow Positive gives you the real numbers, the pitfalls, and the playbook to WIN before the changes vanish again! Timestamped Highlights00:00 – The wildest podcast cold open yet—did Airbnb really listen to this show?01:45 – The “split fee” is BACK: What it means and why it matters for your profit05:40 – Insider data: What happened to hosts’ bookings and income after the single fee switch08:30 – Why Airbnb claims hosts get “more bookings” (and why that’s a vanity metric trap)12:55 – The one move you must make in your property management system to cash in17:00 – The truth about algorithm rankings and dropping your fees (what Airbnb won’t say)18:40 – Top-performing properties vs. average: Who really survives policy chaos?20:00 – Exactly how to prepare for June’s next pricing reset and outsmart 90% of hosts Mentioned ResourcesVRBO (competitive shifts and booking volume)Airbnb Host Fee Structures (split fee vs single fee)Property Management Software (PMS)Emile Sakhel (industry revenue manager) Important LinksWant us to find the deals for you? https://strinsights.com Get Top Markers for STRs (2025) - https://rebrand.ly/28b1df Instagram – @kenny_bedwellYouTube – Cash Flow PositiveLinkedIn – Kenneth Bedwell Cash Flow Positive is an original podcast hosted by Kenny Bedwell. Brought to you by STR Insights. Production and editing by Podcast Your Brand.

    20 min
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5
out of 5
66 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
    174
  • Rating
    Clean
  • Copyright
    © Kenny Bedwell
  • Show Website
    Cash Flow Positive

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