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[12:00] How unfinished basements and outdated designs kill reviews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