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!
Cash Flow Positive
Claim This Podcastby Kenny Bedwell
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Podcast Overview
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!
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Publishing Since
4/23/2024
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Recent Episodes
May 26, 2026
This Mistake Just Cost Me THOUSANDS
Host Kenny Bedwell shares costly renovation mistakes made while managing an 1848 boutique hotel remotely, offering lessons on avoiding budget blowouts and contractor chaos.
May 5, 2026
Two Secrets to Scaling a Successful Portfolio
<p>Are you stuck grinding but never really escaping?</p><p>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. </p><p>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.</p><p>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. </p><p>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.</p><p></p><p></p><h2><strong>Timestamped Highlights</strong></h2><ul><li>00:00 – What most investors get wrong about “scaling up”</li><li>01:58 – The single conversation that shattered my old plan</li><li>03:49 – The moment I made triple rent… and everything changed</li><li>05:25 – The ugly reality of juggling W2, family, and side hustles</li><li>08:23 – The corporate drama that forced my hand</li><li>10:22 – Why time, not money, is your real shortcut to freedom</li><li>14:42 – Why “bold” isn’t gambling and how I protect against disaster</li><li>16:40 – The uncomfortable moves that led to explosive cash flow</li></ul><br/><p></p><p></p><h2><strong>Mentioned Resources</strong></h2><ul><li><u><a href="http://airbnb.com" rel="noopener noreferrer" target="_blank">Airbnb</a></u></li><li><u><a href="https://www.biggerpockets.com/" rel="noopener noreferrer" target="_blank">BiggerPockets</a></u></li></ul><br/><p></p><p></p><h2><strong>Important Links</strong></h2><ul><li>Want us to find the deals for you? <u><a href="https://rebrand.ly/4b6a0d" rel="noopener noreferrer" target="_blank">https://strinsights.com</a></u> </li><li>Get Top Markers for STRs (2025) - <u><a href="https://rebrand.ly/28b1df" rel="noopener noreferrer" target="_blank">https://rebrand.ly/28b1df</a></u> </li><li><u><a href="https://rebrand.ly/313fe7" rel="noopener noreferrer" target="_blank">Instagram – @kenny_bedwell</a></u></li><li><u><a href="https://rebrand.ly/01b56a" rel="noopener noreferrer" target="_blank">YouTube – Cash Flow Positive</a></u></li><li><u><a href="https://rebrand.ly/0a2f2c" rel="noopener noreferrer" target="_blank">LinkedIn – Kenneth Bedwell</a></u></li></ul><br/><p></p><p></p><p>Cash Flow Positive is an original podcast hosted by Kenny Bedwell. Brought to you by STR Insights. Production and editing by <u><a href="https://rebrand.ly/pybkb2026" rel="noopener noreferrer" target="_blank">Podcast Your Brand</a></u>.</p>
April 28, 2026
Who Is ACTUALLY Booking Your Property?
<p>Are your short-term rentals sitting empty while your competitors rake in bookings? You might be targeting the wrong guest without even knowing it. </p><p>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.</p><p>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.</p><p>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.</p><p></p><p></p><h2><strong>Timestamped Highlights</strong></h2><ul><li>00:02 – Dad shirts are back… but is your STR guest strategy stuck in winter?</li><li>00:44 – The secret reason you keep attracting the “wrong” guests (and how to fix it)</li><li>03:03 – Why budget buyers will ignore your amenities—and the pricing trap most hosts fall into</li><li>07:32 – Value seekers, Costco logic, and the most common STR buyer (are you missing easy profits here?)</li><li>10:46 – The convenience persona: Why location, reviews, and guarantees can replace discounts</li><li>13:17 – Experience seekers exposed: Social media-worthy guests—and the Instagram marketing mistake</li><li>16:55 – Luxury buyer drama: When high expectations drive guests to cancel… and why “luxury” is more than just a word</li><li>20:29 – Occasion seekers and the money left on the table when you ignore group dynamics</li></ul><br/><p></p><p></p><h2><strong>Mentioned Resources</strong></h2><ul><li><u><a href="https://www.airbnb.com/stays/luxury" rel="noopener noreferrer" target="_blank">Airbnb Luxe</a></u></li><li><u><a href="https://www.costco.com/" rel="noopener noreferrer" target="_blank">Costco</a></u>, <u><a href="https://www.samsclub.com/" rel="noopener noreferrer" target="_blank">Sam’s Club</a></u>, <u><a href="https://www.dollartree.com/" rel="noopener noreferrer" target="_blank">Dollar Tree</a></u> (buyer mindset examples)</li><li><u><a href="http://instagram.com" rel="noopener noreferrer" target="_blank">Instagram</a></u> (direct booking for experience stays)</li><li><u><a href="https://www.marriott.com/" rel="noopener noreferrer" target="_blank">Marriott</a></u>, <u><a href="https://sheraton.marriott.com/" rel="noopener noreferrer" target="_blank">Sheraton</a></u> (hotel chains, buyer persona contrasts)</li></ul><br/><p></p><p></p><h2><strong>Important Links</strong></h2><ul><li>Want us to find the deals for you? <u><a href="https://rebrand.ly/4b6a0d" rel="noopener noreferrer" target="_blank">https://strinsights.com</a></u> </li><li>Get Top Markers for STRs (2025) - <u><a href="https://rebrand.ly/28b1df" rel="noopener noreferrer" target="_blank">https://rebrand.ly/28b1df</a></u> </li><li><u><a href="https://rebrand.ly/313fe7" rel="noopener noreferrer" target="_blank">Instagram – @kenny_bedwell</a></u></li><li><u><a href="https://rebrand.ly/01b56a" rel="noopener noreferrer" target="_blank">YouTube – Cash Flow Positive</a></u></li><li><u><a href="https://rebrand.ly/0a2f2c" rel="noopener noreferrer" target="_blank">LinkedIn – Kenneth Bedwell</a></u></li></ul><br/><p></p><p></p><p>Cash Flow Positive is an original podcast hosted by Kenny Bedwell. Brought to you by STR Insights. Production and editing by <u><a href="https://rebrand.ly/pybkb2026" rel="noopener noreferrer" target="_blank">Podcast Your Brand</a></u>.</p>
172 total episodes available with 30 transcripts
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Frequently asked questions
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- What is Cash Flow Positive?
- How often does this podcast release new episodes?
This podcast updates daily.
- Where can I listen to this podcast?
This podcast is available on 8 platforms including Apple Podcasts, Spotify, and more. You can also use the RSS feed directly.
- Does this podcast accept guests?
No, this podcast does not typically feature guests.
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