Cash Flow Positive Part 1: The #1 strategy to increasing occupancy
Who says you have to settle for empty nights and slow seasons in your short-term rental business?
Today, Kenny Bedwell, the data-driven founder of SCR Insights and host of Cashflow Positive, uncovers the single most overlooked tactic for filling your calendar year-round. Whether you’re brand new or a seasoned investor tired of watching rival listings rack up bookings, you’re about to learn how to outsmart the algorithm, target untapped guest avatars, and supercharge your occupancy without slashing prices or adding another hot tub.
Forget the usual "add amenities and hope" advice. Kenny Bedwell shares raw stories, market case studies, and step-by-step strategies for duplicating and syncing your listings, hacking bedroom counts, and designing your calendar to capture both big groups and last-minute couples. If you want practical, counterintuitive tactics with real revenue impact, press play and get ready to rethink your entire listing game.
Timestamped Highlights
[00:01:00] – Understanding amenities: Differentiating what boosts ADR vs. occupancy
[00:03:00] – The real #1 occupancy strategy: Duplicating listings and adjusting bedroom/guest count
[00:04:22] – Buffalo duplex playbook: Parent-child listing method for seasonality
[00:06:02] – The calendar hack—setting advance notice to maximize bookings in both units
[00:09:00] – Blue Ridge, GA case study: How listing a three-bedroom as a two-bedroom crushes the competition
[00:11:45] – Airbnb algorithm secrets: How your listing size controls visibility and booking rate
[00:13:24] – Application for single-family homes—catching snowbirds, couples, and off-season guests
[00:17:36] – Side-by-side and duplex strategy: What guest avatars really want (and when you lose money)
[00:19:20] – The essential gathering area: Why big bookings may flop without this overlooked space
[00:21:38] – Experiment, critique, and pivot—how to "round the wheel" and not just reinvent it
[00:23:01] – Invitation to STR Scale Summit: Get the connections and knowledge to scale fast
Mentioned Resources
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.