What if your next short-term rental deal isn’t failing because of the numbers… but because of your reviews?

In this episode of Cash Flow Positive, Kenny Bedwell digs into the “curse” of review-driven real estate—how guest expectations, property condition, and first impressions can quietly make or break your returns. He breaks down the two sides of STR investing (real estate + hospitality), shares real-world examples from his own portfolio, and explains why operations and guest experience are just as critical as deal analysis.

You’ll learn what details guests really notice, how to find properties that support great reviews from day one, and the simple fixes that turn complaints into five-star ratings.

If you want your short-term rental to outperform the market, hit play and start thinking like a guest, not just an investor.

[00:00] Why Kenny “hates” reviews 4and how they shape investor behavior

[01:00] The two-headed monster of STR investing: real estate + hospitality

[02:30] Why being a great host directly impacts revenue

[04:00] How property age and updates influence guest satisfaction

[06:00] Lessons from a historic 1860s home that became a five-star stay

[09:00] The hidden cost of ignoring capital expenditures

[10:40] When old systems (like HVAC) destroy the guest experience

[12:00] How unfinished basements and outdated designs kill reviews

[15:20] External factors: neighbors, privacy, roads, and power lines

[20:00] Designing for privacy, accessibility, and comfort

[23:00] How to impress guests from the moment they arrive

[25:00] The power of small touches, like Kenny’s ice cream bar idea

[27:00] Why first impressions make or break your ratings

[30:20] The link between five-star reviews and long-term revenue

• Want us to find the deals for you? https://strinsights.com
• Get Top Markers for STRs (2025) https://www.strinsights.com/top-investable-short-term-rental-markets-2025-report
• 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 and Podcast Your Brand. Production and editing by Podcast Your Brand

If you’ve been chasing the next “get rich quick” shortcut in real estate… this episode is your reality check.

In this episode of Cash Flow Positive, Kenny Bedwell flips the script on fast money and exposes the truth about building real wealth through real estate. He shares insights from conversations with high-level investors: Those who buy $100M hotels and still play the long game and reveals why the biggest wins come from appreciation, tax strategy, and equity paydown, not just monthly cash flow.

You’ll learn the four true pillars of wealth in real estate, how to think like an investor instead of a speculator, and why repositioning your assets the right way can transform your portfolio faster than chasing short-term returns ever will.

Stop looking for overnight success. Press play now to learn how the smartest investors actually get rich with patience, data, and a long-term plan.

[00:00] Back from the flu and fired up about “get rich quick” myths

[01:30] The problem with chasing only cash flow

[03:35] Lessons from top-tier investors who buy $100M properties

[05:00] The four wealth pillars: cash flow, appreciation, tax savings, and equity paydown

[07:00] What “repositioning” really means and why it’s where wealth is built

[09:25] When cash flow should be your priority and when it shouldn’t

[10:30] Why high-income professionals invest differently (and what that means for you)

[12:30] How to calculate true ROI using total return, not just cash flow

[15:20] The mindset shift: stop chasing income, start building net worth

[18:30] Defining your investment goals before you buy your next STR

[21:15] How Kenny evaluates deals now and why forced appreciation beats “good enough”

• Want us to find the deals for you? https://strinsights.com
• Get Top Markers for STRs (2025) https://www.strinsights.com/top-investable-short-term-rental-markets-2025-report
• 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 and Podcast Your Brand. Production and editing by Podcast Your Brand

Most investors look at bedroom counts at face value. Kenny Bedwell doesn’t.

In this episode of Cash Flow Positive, Kenny reveals a deal-finding strategy he’s seen quietly pay off in competitive short-term rental markets: targeting properties with extra square footage and converting them into higher bedroom counts. From Sedona to the Poconos, Kenny explains why “heads in beds” is the #1 revenue driver, how to legally add bedrooms to force appreciation, and why average-performing STRs will always lose out to top properties.

You’ll hear how to spot these overlooked opportunities, the math that makes them work, and why moving quickly under contract is often the difference between landing a deal and watching it slip away.

Don’t settle for average returns. Press play now to learn how Kenny turns overlooked listings into high-cash-flow, high-appreciation wins.

• Want us to find the deals for you? https://strinsights.com
• Get Top Markers for STRs (2025) https://www.strinsights.com/top-investable-short-term-rental-markets-2025-report
• 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 and Podcast Your Brand. Production and editing by Podcast Your Brand.

Is refinancing your short-term rental a smart move—or a trap that eats away your cash flow?

In this episode of Cash Flow Positive, Kenny Bedwell sits down with veteran mortgage broker and STR financing expert Matt Stout. With over 32 years of lending experience and thousands of deals funded, Matt pulls back the curtain on when refinancing actually makes sense. From dropping interest rates and shifting housing trends to creative ways to redeploy “dead equity” into higher cash-flowing properties, this episode delivers the unvarnished truth about refinancing in today’s market.

You’ll learn the right (and wrong) reasons to refinance, how to weigh costs versus cash flow, and why keeping versus selling a property can make or break your long-term wealth.

Don’t guess your way through one of the biggest financial decisions you’ll face as an investor. Press play now to get Kenny and Matt’s proven framework for knowing when to refinance and how to use it to build real generational wealth.

Matt Stout is “The STR Loan Guy” and founder of Consumers Financial, a mortgage brokerage licensed in 48 states. With over three decades in lending and a personal background in real estate investing, Matt specializes in STR and DSCR loans that help investors unlock equity and scale their portfolios. He’s known for creative lending strategies, hybrid loan solutions, and his straight-shooting approach to helping investors win deals.

🔗 STR Loan Guy Website | YouTube – STR Loan Guy | Facebook | TikTok @thestrloanguy

• Want us to find the deals for you? https://strinsights.com
• Get Top Markers for STRs (2025) https://www.strinsights.com/top-investable-short-term-rental-markets-2025-report
• 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 and Podcast Your Brand. Production and editing by Podcast Your Brand.

If someone handed you $250,000 in cash to invest in a short-term rental, where would you buy and what strategy would you use to make that money work?

In this episode of the Cash Flow Positive Podcast, host Kenny Bedwell is joined by Erin Wegrzyn, a real estate consultant with STR Insights, to explore exactly that scenario. Together, they break down how to choose the right markets, set realistic expectations, and avoid the “amenities arms race” that eats into cash flow.

Erin shares her journey from long-term rental investor to short-term rental specialist and why her strategy has shifted toward properties that both cash flow and create memories for her family. Kenny and Erin discuss how to research markets, stay ahead of competitors, and build a property that can grow with the market over time, without burning out or over-renovating.

If you've enjoyed this episode of the Cash Flow Positive podcast, be sure to leave a review and subscribe today! Listen now and enjoy!

Key takeaways:

• How to choose markets without spreading yourself too thin
• Why being “one of one” in a market is a huge advantage
• How to avoid competing in an endless amenities war
• What to look for in properties that allow for future upgrades
• Why following where large investors are putting money can reveal emerging markets
• The best way to build a reliable local team of contractors and cleaners
• Why you should visit and experience a market before you invest there
• And much more...

Guest Bio:

Erin Wegrzyn is a real estate consultant with STR Insights, where she helps investors analyze markets and identify profitable short-term rental opportunities. Based in Kentucky, she brings firsthand experience as an investor and a deep understanding of market trends, property selection, and building reliable local teams. Erin is passionate about helping clients choose properties that cash flow, grow in value, and fit their lifestyle goals.

Resources:

Connect with Kenny on LinkedIn

Follow Kenny on Instagram

Disclaimer:

The views, information, or opinions expressed during this podcast are solely those of the individuals involved and do not necessarily represent those of the Cash Flow Positive podcast or its affiliates. The content provided is for informational and entertainment purposes only and is not intended to be a substitute for professional advice. We make no representations as to the accuracy, completeness, suitability, or validity of any information on this podcast and will not be liable for any errors, omissions, or delays in this information or any losses, injuries, or damages arising from its display or use. Listeners should consult with a professional for specific advice tailored to their situation. By accessing this podcast, you acknowledge that any reliance on the content is at your own risk.

If $250,000 dropped into your lap today, would you actually know what to do with it?

In this episode of Cash Flow Positive, Kenny Bedwell pulls back the curtain on exactly how he’d put that money to work in short-term rentals. He breaks down why your financing strategy can make or break a deal, the five cost buckets most investors forget about, and why setting your ROI goal up front is non-negotiable.

You’ll hear Kenny think through real markets, from Florida beaches to Shenandoah cabins, and explain how to spot which ones fit your budget and which ones will bleed you dry.

Don’t guess your way into a $250K mistake. Hit play now to hear Kenny’s no-fluff, data-backed roadmap and get clarity on where your money will actually cash flow.

[00:00] How a $250K windfall changes your investing strategy overnight

[02:14] The financing trap that torpedoes deals before they close

[04:18] The five hidden costs every STR investor must budget for

[07:36] Kenny’s minimum ROI goals—and why cash flow beats percentages

[10:53] The “process of elimination” method for picking your markets

[14:25] Why Bradenton, FL, might work—and the brutal barrier to entry

[21:00] Shenandoah’s low-barrier charm vs. beach market competition

[24:38] How lakefronts in Michigan and urban rentals in Cincinnati stack up

• STR Insights software
• Top Markets Report (via STR Insights website)
• Dave Ramsey podcast (benchmark reference)
• Zillow & Redfin (for market comps)

Evergreen Links

• Want us to find the deals for you? https://strinsights.com
• Get Top Markers for STRs (2025) https://www.strinsights.com/top-investable-short-term-rental-markets-2025-report
• 📲 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 and Podcast Your Brand. Production and editing by Podcast Your Brand.

What does Airbnb’s latest fee increase mean for your bottom line, and how should it change the way you evaluate deals?

In this episode of the Cash Flow Positive Podcast, Kenny Bedwell sits down with Rachel Gniady, full-time real estate investor and STR Insights consultant, to talk about how the new 15.5% host fee is reshaping underwriting, deal selection, and long-term strategy.

Rachel shares how she is being even more conservative with revenue estimates, why she is rejecting deals that don’t have a wide enough margin, and why being “one of one” in a market is more important than ever. Together, Kenny and Rachel dive into moats, market trends, appraisals, and the importance of thinking like an investor first, even as competition heats up and the “middle” of the STR market gets squeezed.

Want to keep spotting high-margin STR deals even as fees climb? Listen now and sharpen your strategy. If you've enjoyed this episode of the Cash Flow Positive podcast, be sure to leave a review and subscribe today! Listen now and enjoy!

Key takeaways:

• Why Airbnb’s fee change demands more conservative underwriting
• How to evaluate properties with a “good, better, best” revenue approach
• Why being unique in your market protects your profits
• The dangers of chasing trends and how to know when to walk away
• Why comps, cost basis, and appraisals matter more than ever
• How to protect yourself in today’s “Wild West” real estate market
• Why stability can beat higher short-term returns in the long run
• The importance of making offers quickly and confidently
• And much more...

Guest Bio:

Rachel Gniady is a full-time real estate investor and consultant for STR Insights, where she has helped over 50 clients close deals and build profitable short-term rental portfolios. Based in New Orleans, she has nearly 20 years of experience buying, improving, and selling properties.

Resources:

Connect with Kenny on LinkedIn

Follow Kenny on Instagram

Part 2: Finding High ROI STR Deals with No Money with Rachel Gniady

Connect with Rachel on LinkedIn

Disclaimer:

The views, information, or opinions expressed during this podcast are solely those of the individuals involved and do not necessarily represent those of the Cash Flow Positive podcast or its affiliates. The content provided is for informational and entertainment purposes only and is not intended to be a substitute for professional advice. We make no representations as to the accuracy, completeness, suitability, or validity of any information on this podcast and will not be liable for any errors, omissions, or delays in this information or any losses, injuries, or damages arising from its display or use. Listeners should consult with a professional for specific advice tailored to their situation. By accessing this podcast, you acknowledge that any reliance on the content is at your own risk.

Airbnb has just announced a major change to its fee structure, and for hosts, the impact could be huge.

In this episode of the Cash Flow Positive podcast, Kenny Bedwell breaks down the shift from a split-fee model to a single-host fee of 15.5%. He explains what this really means for your payouts, why simply raising your rate isn’t the answer, and how the wrong pricing strategy could tank your rankings and bookings.

Kenny walks through the math behind the change, why some hosts will be hit harder than others, and what you can do to protect your bottom line. From understanding price elasticity to planning ahead with discounts and direct bookings, this episode is packed with insights and strategies you won’t want to miss.

Don’t let Airbnb’s new fee structure cut into your earnings. Tune in to learn the smart strategies that keep your payouts strong.

If you've enjoyed this episode of the Cash Flow Positive podcast, be sure to leave a review and subscribe today! Listen now and enjoy!

Key takeaways:

• Why raising your prices could hurt your rankings
• How pricing without a strategy leaves you vulnerable to underpriced competitors
• Why cookie-cutter properties are more exposed than unique listings
• The exact percentage increase needed to maintain your current payouts
• Why timing your price adjustments can affect your Airbnb search rankings
• How to think about cause and effect when responding to platform changes
• And much more...

Resources:

Connect with Kenny on LinkedIn

Follow Kenny on Instagram

Disclaimer:

The views, information, or opinions expressed during this podcast are solely those of the individuals involved and do not necessarily represent those of the Cash Flow Positive podcast or its affiliates. The content provided is for informational and entertainment purposes only and is not intended to be a substitute for professional advice. We make no representations as to the accuracy, completeness, suitability, or validity of any information on this podcast and will not be liable for any errors, omissions, or delays in this information or any losses, injuries, or damages arising from its display or use. Listeners should consult with a professional for specific advice tailored to their situation. By accessing this podcast, you acknowledge that any reliance on the content is at your own risk.