Are you one tough market away from making or breaking your STR dreams? In this eye-opening solo episode, Kenny Bedwell delivers his no-BS, data-driven breakdown of 2025’s market shakeups and lays out urgent, can’t-miss predictions for 2026.

With competition at a boiling point and Airbnb’s pricing bombshell still sending shockwaves, Kenny Bedwell exposes where investors keep getting crushed, and who’s quietly winning big. From wild price slashes to the “big fish or die” investor mentality, this episode is packed with the kind of ruthless honesty and hard metrics you won’t get from any hype-driven guru.

Tune in now or risk fumbling the next 12 months. Discover the exclusive moves smart investors will make next, before the rest of the market catches on, and before average operators are left behind for good.

[00:00] – Why “average” properties are getting destroyed while 90th percentile performers quietly flourish

[00:03:51] – The mindset shift every STR buyer must make now to avoid draining cash flow

[00:06:26] – Markets you’d written off are making a shocking comeback—here’s why

[00:08:17] – Explosive legal shakeups: Are STRs still real estate or something else?

[00:10:33] – The Airbnb fee switch: How hosts are sabotaging themselves and tanking in search rankings

[00:13:10] – The real reason your smart price hikes backfired—and how to break the algorithm instead

[00:18:46] – The “turnkey trap”: Why offloading STRs is about to flood the market (and what smart buyers must do now)

[00:24:33] – Surprise winners & fallen stars: The brutally honest 2026 top markets preview

[00:26:31] – Kenny’s wild 2026 prediction: The coming Airbnb “pay to play” era

1. STR Scale Summit (event)
2. Top Markets Report (via STR Insights)
3. Airbnb Luxe
4. Airdna (STR market data)

1. Want us to find the deals for you? https://strinsights.com
2. Get Top Markers for STRs (2025) - https://rebrand.ly/28b1df
3. Instagram – @kenny_bedwell
4. YouTube – Cash Flow Positive
5. 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.

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.

[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”

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.

🔗 LinkedIn

• AirDNA

• 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.

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.

[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

• Hospitable
• OwnerRez
• Airbnb
• VRBO

• 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.