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.

Hiring contractors is hard enough… hiring them out of state can feel terrifying.

In this value-packed episode of Cashflow Positive, Kenny sits down with Jen Josey, real estate investor, coach, mastermind leader, and construction expert, to break down exactly how to find, vet, manage, and protect yourself when working with contractors in markets where you don’t live.

Jen shares the six critical documents every investor should use, the insider process for finding investor-friendly contractors (hint: it’s not Google), how to structure payment schedules that protect your budget, and the legal tools that saved her from a lawsuit.

If you plan to renovate a property outside your local market, this conversation may literally save you thousands.

[00:00] Meet guest Jen Josey and her path from teacher → corporate → real estate

[00:01:20] How Jen replaced her corporate income in 8 months

[00:01:55] What Jen is working on today: coaching, STRs, investing, and running multiple companies

[00:03:00] Current STR portfolio: beach condo, Boone cabin, and plans for a micro-resort

[00:05:00] What Jen looks for: smaller STRs, pet-friendly, waterfront, couples-focused

[00:06:25] How she evaluates markets in NC, VA, and SC

[00:08:10] Kenny’s lead-in to contractor horror stories and out-of-state projects

[00:09:00] Jen’s #1 starting point: investor Facebook groups (and how to post correctly)

[00:09:45] Step 2: local REIAs (why they matter and what quality they attract)

[00:10:40] Window replacement sticker shock: a real example ($7K for three windows)

[00:12:00] Never pay large deposits upfront—and what to do instead

[00:12:45] The exact six critical documents every investor should use

[00:13:35] The “lien waiver” that saved Jen from being sued

[00:14:10] The contract: deadlines, penalties, warranties, and holding contractors accountable

[00:15:40] Insurance + indemnification: adding yourself to a contractor’s policy

[00:16:20] Building your scope of work from the inspection report

[00:16:55] Paying your inspector to verify contractor work

[00:17:40] The proper way to structure a payment schedule (why the final payment is the largest)

[00:18:55] W-9 requirements for anyone paid over $600

[00:19:20] Contractors who refuse to sign contracts—why you should walk away

[00:20:05] Kenny’s theater room story and how a missing change order cost him

[00:21:55] How to prevent “death by $500 change orders”

[00:23:15] How hard money lenders help enforce accountability

[00:24:00] What makes someone an investor-friendly contractor

[00:27:00] Jen’s secret weapon: “pimping out” contractors to keep prices low

[00:29:00] Code of Conduct on job sites (English + Spanish)

[00:33:00] The two most important people on your STR team: cleaners + handyman

[00:34:25] Paying your handyman well to secure long-term loyalty

[00:35:00] Jen’s final tip for cash flowing positive: deliver unforgettable guest experiences

[00:37:00] Why theme ≠ experience (Kenny’s Taylor Swift pillow story)

[00:39:20] Where to follow Jen and how to get her contractor documents

Jen Josey is a real estate investor, coach, podcaster, and founder of the Real Estate Investor Growth Network (REIGN). After leaving her corporate job, Jen built a diverse portfolio across long-term rentals, short-term rentals, flips, and new construction. She runs multiple companies under the Joli brand, including construction, brokerage, and investment arms, and coaches investors nationwide on buying and renovating out of state.

She is also the host of the Real Estate Investor Growth Network Podcast and leads a mastermind for active investors.

🔗

Ever felt blindsided by skyrocketing costs and endless delays when renovating a property out of state? You are not alone, and you do not have to fall victim to contractor nightmares again.

In this no-fluff solo episode, Kenny Bedwell (the relentless numbers-driven voice behind Cash Flow Positive) drops a real talk blueprint for working with out-of-state contractors on STR investments, so you keep your profits high and your headaches low. Pulling from raw experience and data-backed practical steps, he reveals the biggest blunders investors make, how to negotiate with confidence, and exactly what you must ask (and never say!) before handing over your dollars.

Don’t get burned by rookie mistakes or overpriced quotes. Listen now for the counterintuitive tactics, time-saving hacks, and inside knowledge you will not get anywhere else. Delay and you risk expensive lessons—press play for power, profit, and peace of mind.

[00:00] – Why most investors get “out-of-state” pricing—and how to avoid the trap

[00:02:28] – The one detail about yourself you must hide when calling contractors

[00:05:08] – Project management nightmares: overlapping crews, costly delays, and what nobody tells you

[00:08:00] – Inside Kenny Bedwell’s painful 6-month permit saga (and the holding costs almost everyone forgets)

[00:10:40] – Social media as a referral jungle: How to decode real reviews from angry rants

[00:16:08] – The invisible 10–15% overage rule and why your budget always lies

[00:18:00] – The supply scam: How to keep contractors from secretly padding their profits

[00:22:05] – The exact moment you should call contractors (Miss it, and it’ll cost you thousands!)

• The Home Depot
• Lowe’s Home Improvement
• Angi (formerly Angie’s List)
• Better Business Bureau

• 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.

$200,000 used to feel like a powerhouse investing budget… but in today’s short-term rental landscape, it doesn’t go nearly as far as it used to.

In this solo episode, Kenny Bedwell breaks down the hard truth: $200K is the new $100K.

Competitive STR markets have leveled up, amenities have escalated, and investor expectations have shifted. Kenny walks through why $200K no longer guarantees entry into the big-boy markets (Smokies, Bradenton, Asheville, Bourbon Trail), what buyers consistently misunderstand about down payments vs. true budget, and how to think like a strategic investor rather than a pre-approval chaser.

He also unpacks the 20% Rule, the reality of amenity wars, why your biggest moat is future thinking, and the path newer investors should take when they have less than $200K to deploy.

If you want to make your money actually work and stop getting crushed by competition, this episode is your roadmap.

[00:00] Why $200K doesn’t stretch like it used to

[00:01:20] The psychological trap of buying based on pre-approval

[00:02:10] The 20% Rule: what your true budget actually is

[00:03:20] Why a $500K home can require $200K to do it right

[00:04:40] Competitive markets and the real cost of keeping up

[00:06:00] When big brokerage agents start pushing a market… it’s already too late

[00:07:20] Why chasing what worked last year won’t work now

[00:08:10] Downsizing: why a killer 2–3 bedroom beats an underfunded 6-bedroom

[00:09:20] The amenity war: pickleball courts, splash pads, heated pools, full design

[00:10:50] Real estate finance lesson: why abnormal returns disappear

[00:11:40] Today ≠ 2021: why $200K no longer buys performance

[00:12:25] How to pick markets with lower barriers of entry

[00:13:10] What “drivable markets” really are and why they outperform

[00:14:35] How to read metropolitan travel patterns for hidden gems

[00:15:40] Why most investors are psychologically wired to overleverage

[00:16:20] The only way to compete with bigger players

[00:17:50] Planning for future competition, not past comps

[00:18:30] Kenny’s Walkins Glen example: $350K → $144K gross

[00:19:30] Why futuristic thinking builds moats

[00:20:10] The Autopilot app story (Nancy Pelosi portfolio tracking)

[00:22:15] Understanding how investor flood-ins flatten returns

[00:23:20] How to pick properties that will hold up against new competition

[00:24:30] If you want a moat, you must create it

[00:25:10] Kenny’s offer to break down “moat categories” in a future episode

[00:25:50] How to message Kenny directly with questions

• Autopilot App (stock trading tool tracking politician trades)

• 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.

Most people get into real estate for freedom, but what happens when the money isn’t enough?

In this powerful episode of Cashflow Positive, host Kenny Bedwell sits down with Caleb David, a commercial real estate broker, investor, and longtime nonprofit leader whose story goes far beyond deals, commissions, and spreadsheets.

Caleb opens up about his early years growing up in a strict environment, his burnout in the nonprofit world, and the leap of faith that brought him into commercial real estate. He also shares candidly about nearly going bankrupt, rebuilding from scratch twice in the same year, and discovering what it really means to live a life of purpose.

The deeper theme of this episode: Real estate might bring wealth… But purpose and service bring fulfillment.

Caleb’s work with Crazy Love Africa, his time in Ethiopia, his worldview shaped by humanitarian work, and his approach to “creating space and building community” give listeners a new way to think about success, impact, and the life they’re building.

This conversation is grounding, challenging, and wildly inspiring.

[00:00] Meet Caleb, from conservative upbringing to nonprofit burnout

[00:01:50] The leap into commercial real estate and surviving on commission

[00:03:00] Becoming Rookie of the Year during a recovering market

[00:04:20] Why Caleb doesn’t specialize and how sectors overlap (retail, industrial, STR + commercial combos)

[00:05:10] COVID’s impact on the industrial + retail markets

[00:06:20] How STR investors can begin learning commercial real estate

[00:07:00] The value of curious brokers, not “know-it-alls”

[00:09:20] Why empathy belongs in real estate

[00:10:30] The theme of “creating space, building community”

[00:11:00] Looking beyond money — purpose, faith, and fulfillment

[00:12:10] Caleb’s global nonprofit work in Ethiopia and the Middle East

[00:14:15] The dangers of “savior mentality” when giving

[00:15:40] Introducing When Helping Hurts (book)

[00:16:25] Supporting women with HIV in Uganda through Crazy Love Africa

[00:17:25] Microgrants: $500 that changes a family’s future

[00:18:10] Fair-trade crafts made by women artisans

[00:19:00] How giving time can matter more than giving money

[00:20:00] Letting go of ego + redefining impact

[00:21:30] How to find nonprofits that align with your values

[00:23:45] Using 990 forms to evaluate nonprofit transparency

[00:25:50] How Caleb balances business, service, and personal well-being

[00:27:00] Why rest makes you more productive

[00:28:20] Healing from trauma and overcoming near-bankruptcy

[00:30:10] Taking “the next right step” in real estate and life

[00:33:15] Caleb’s final advice to ambitious professionals

[00:34:20] How to connect with Caleb + where to learn more

Caleb David is a commercial real estate broker, investor, podcaster, and humanitarian based in Colorado. With a background that spans 20+ years in the nonprofit sector, global humanitarian work in Ethiopia and the Middle East, and nearly a decade in commercial brokerage, Caleb brings a rare blend of business expertise and deep-purpose leadership.

Today, he serves clients across the Colorado market through Keller Williams Commercial while also serving on the board of Crazy Love Africa, an organization supporting women and children impacted by HIV in Uganda. His mission: create space, build community, and leave a meaningful impact both locally and globally.

🔗 LinkedIn | Instagram |

Innovation isn’t just about building something new; it’s about building something better.

In this episode of Cash Flow Positive, host Kenny Bedwell sits down with Juliano Silva, a full-time short-term rental investor and designer who’s built a portfolio of standout “signature properties” across multiple U.S. markets. From his early beginnings renting out a spare bedroom in Minnesota to creating high-performing STRs in Florida, Juliano shares how data, creativity, and intention fuel his approach to innovation.

They discuss the art of designing properties that can’t be copied, why standing out takes more than adding a pickleball court, and how to create guest experiences that drive both profitability and longevity. Juliano also opens up about building his own construction and design team, the value of experimentation, and how he protects his creative work while staying one step ahead of imitators.

If you’ve ever wondered how to make your STR truly unforgettable, this conversation is your blueprint.

[00:00] Meet Juliano Silva – From web developer to full-time STR investor

[00:01:30] The accidental first Airbnb: renting a bedroom in Minneapolis

[00:03:40] Early lessons in regulation and risk

[00:05:00] Transitioning from long-term rentals to short-term opportunities

[00:07:00] How COVID opened the door to their first real STR in Sarasota

[00:09:00] Turning a distressed property into a six-figure rental

[00:10:00] Building an in-house design and renovation team from scratch

[00:11:30] From experimentation to intentionality – creating “signature properties”

[00:14:20] The first pickleball court in Sarasota-Bradenton

[00:15:30] Using Google Trends and data to innovate amenities

[00:17:30] Why copycats will never win and how to stay ahead through originality

[00:19:00] Innovation as a mindset, not just a feature

[00:21:00] Designing for brand identity and guest retention

[00:23:00] Balancing appreciation and cash flow in every investment

[00:24:20] How Juliano protects his designs (and his energy)

[00:27:00] Drawing inspiration from international design and hospitality

[00:29:30] Innovating the guest experience with continuity and theme

[00:32:00] The E.R.O. Formula: Acquisition, Experience, Revenue, Operations

[00:37:00] Innovation as problem-solving like early check-in strategies

[00:39:30] Competing through service, not just price

[00:43:00] Juliano’s top advice: “When they zig, you zag.”

[00:45:00] Staying true to your fundamentals and cash flowing positive

Juliano Silva is a full-time real estate investor, designer, and founder of Behind Every Stay, a newsletter and consulting platform that helps investors create profitable, guest-loved short-term rentals. Based in California with properties across Florida, Minnesota, and North Carolina, Juliano has spent more than a decade in real estate, transitioning from long-term rentals to building data-driven, experience-focused STRs he calls “signature properties.” His approach blends creativity, analytics, and brand identity, helping investors think beyond amenities and build lasting value through intentional design and innovation.

🔗 LinkedIn | Website | Facebook | Instagram | X | Behind Every Stay...