Cash Flow Positive Part 2: The #1 strategy to increasing occupancy
Are you feeling stuck with underwhelming bookings, even with a great short-term rental? Wondering how savvy investors transform high-mortgage properties into unstoppable cash flow machines without risky over-investment or luck?
In this bold, results-focused episode, Kenny Bedwell sits down with data-driven real estate strategist Jess Broyles, who reveals the real-world playbook that turned ordinary homes into 6-figure yielders.
Get ready for an unfiltered breakdown of advanced multi-listing tactics, practical tools to maximize occupancy, and Jess’s boots-on-the-ground math for keeping quality guests (and profits) coming, year-round. They dive deep into mindset shifts, fatal mistakes, when to spend (and when not to), and market research that actually pays off.
Do NOT let another empty night erode your returns. Listen now to grab exclusive, actionable insights only found here and beat the saturated STR market before the next booking season hits.
Timestamped Highlights
[00:00] The math teacher turned STR powerhouse—how rage at bad rentals lit the fuse
[00:06:44] Why “saving space for amenities” is a game-changing investment secret
[00:13:24] The bold credit card move that jumpstarted Jess’s property empire
[00:17:59] Multi-listing magic: How to 7x your calendar with a single property
[00:19:02] Letting go of pride—how renting a 2-bedroom in a mansion brings surprising wins
[00:22:01] The shocking threshold where discounting destroys guest quality
[00:25:47] How “lock-off” room strategies turn one house into multiple money makers
[00:30:00] Real numbers: The strategy that made $160k more—same houses, zero hype
[00:36:05] Ready to renovate? How spending less on kitchens, more on what matters, trumps “amenity creep”
About the Guest
Jess Broyles is a seasoned short-term rental investor, strategist, and consultant with STR Insights. With six years in the STR game and a background in math education, she specializes in revenue management and creative property optimization. Jess’s distinct perspective turns average homes, even in challenging markets, into six-figure cash-flow properties through data-driven strategy and hands-on ingenuity.
Resources Mentioned
Important Links
- Want us to find the deals for you? https://strinsights.com
- Get Top Markers for STRs (2025) - https://rebrand.ly/28b1df
- 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. Production and editing by Podcast Your Brand.