Part 1 – You MUST Innovate in the STR Space

Nov 11, 2025

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If your short-term rental looks the same as it did three years ago, you’re already falling behind.

In this episode of Cash Flow Positive, host Kenny Bedwell explains why innovation isn’t optional. It’s the only way to stay competitive in a rapidly evolving STR market. From hotel refresh cycles to new amenity trends, Kenny breaks down how to model what the pros do and apply it to your own properties.

He shares real examples of how top operators are staying ahead, from custom pickleball-court designs and splash pads to unique features like three-sided golf simulators and container pools, and why the hosts who think three to five years ahead always win.

Learn how to build your own “moat,” create long-term value, and keep your listings at the top of the market.

Timestamped Highlights

[00:00] Why every STR owner must think like a hotel brand

[00:01:00] The hotel renovation cycle and what it teaches hosts about innovation

[00:02:00] Sneak peek: Kenny’s live event in New Orleans (Feb 28 – Mar 1) on scaling beyond STRs

[00:04:30] The hidden power of staying ahead of your competition

[00:07:00] Thinking long-term three- to five-year reposition cycles

[00:08:30] Why copying others’ amenities is a race to the bottom

[00:09:40] The “Fab Five” amenities and how to make yours stand out

[00:12:45] How Kenny’s $40K three-sided golf simulator became a game-changer

[00:15:30] New trends: designer pickleball courts, splash pads, and beyond

[00:17:30] Building room for future upgrades into every property

[00:18:40] How one container pool added $60K in annual revenue

[00:20:35] When it’s smarter to innovate than to buy another property

[00:21:20] Lessons from hotel design and guest experience

[00:22:45] Practical ways to stay “top dog” in your market

Resources

Attend Kenny’s Live Scaling Event (Feb 28–Mar 1, New Orleans)

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 and Podcast Your Brand. Production and editing by Podcast Your Brand.