Are you stuck waiting for the “big crash” to finally buy your dream short-term rental? What if that crash already came…and left you behind?

In this radically honest episode of Cash Flow Positive, host Kenny Bedwell brings on industry powerhouse Avery Carl for an unfiltered look at the post-pandemic real estate landscape. Avery Carl pulls from 10+ years and 5,000+ deals to reveal why smart investors are thriving while others are paralyzed by analysis, hype, and old strategies that simply don’t work anymore. If you want no-BS answers on timing the market, dealing with stubborn sellers, navigating high-interest rates, and finally making offers that actually win, you’ll find them here.

Don’t miss this straight-shooting, numbers-backed conversation with actionable takeaways for buyers AND sellers. Listen now to avoid the pain of missing out (again), capitalize on this rare window, and sidestep the false promises dominating today’s real estate noise. The market’s moving fast, and this episode is your roadmap to real victory.

[00:00] Startling confessions: Why the crash you’re waiting for already happened

[00:02:31] The brutal math on home prices—what truly stops them from falling

[00:03:39] Are you “catching a falling knife?” The secret cost of waiting for perfection

[00:07:51] How the offer game has totally changed (and hacks for today’s market)

[00:11:04] Real talk for sellers: Tough love, tough comps, and the biggest mistakes to avoid in 2024

[00:17:16] Stop buying ugly houses: Emotional pitfalls and winning tricks for higher resale value

[00:20:25] Beach access, views, and “turds with sprinkles”—what REALLY draws cash flow (and what kills it)

[00:26:48] The amenities arms race: At what point does “over-improving” backfire?

[00:33:36] Who’s buying next? The ignored risk that threatens every STR investor’s exit

1. Smarter Short Term Rentals – Facebook group
2. STR Scale Summit
3. BRRRR Strategy by David Greene
4. BiggerPockets

Avery Carl is the CEO and Founder of The Short Term Shop, the nation’s largest short-term rental-specific real estate brokerage. With more than 5,000 vacation rental transactions and 250+ personal investment doors, she’s a leading voice on how to think—AND act—smart in today’s unpredictable market. Avery’s blunt, data-backed advice and “own what works” mentality make her a must-follow for anyone serious about building wealth through real estate.

🔗 LinkedIn | Website

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 sick of recycled guru advice and worried about making the wrong move in today’s wild STR market?

Kenny Bedwell cuts through the noise with brutal honesty and stark data, giving you the freedom to say no to hype and yes to cash-flow-positive deals.

In this punchy solo episode, he dives into the real state of the industry for 2026: how incentives twist advice you hear, why copycat “hotspots” will cost you big, and the practical innovations it takes to own your future profits. From dissecting shady vendor deals to revealing why being different is safer than ever, Kenny Bedwell arms you with rare, actionable insights.

Don’t get taken for a ride. Listen now to dodge avoidable disasters and seize proven, data-driven strategies you won’t find in the TikTok echo chamber. This is your unfair advantage, before the market leaves you behind.

[00:00] — The explosive problem with industry advice everyone ignores

[00:01:06] — Why “I just want to help” usually hides a dollar sign

[00:04:13] — The hidden motives that can quietly sink your next deal

[00:05:50] — Who’s selling short-term rental hope… and who’s selling hype?

[00:07:16] — The low-rate loan trap: what most investors miss before it’s too late

[00:10:04] — Realtor myths exposed: why those “best markets” rarely are

[00:11:01] — Overhyped markets vs. overlooked goldmines: what really works in 2026

[00:17:02] — The real shortcut to stand-out STR success (hint: it’s not more decor)

1. DSCR loans / second home loans
2. Airdna (indirect mention: short-term rental data providers)
3. STR Scale Summit
4. STR Wealth Con
5. ChatGPT (tool for creative brainstorming)
6. Wayfair (STR furnishing and amenity sourcing, referenced in context)

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.

When’s the last time your calendar made you real money? Most hosts set their pricing, cross their fingers, and hope the bookings roll in… all while leaving thousands on the table and letting holidays sabotage their revenue.

In this actionable episode, Kenny Bedwell sits down with powerhouse educators Annette Grant and Sarah Karakaian from Thanks for Visiting to unpack how “mom and pop” operators can finally run their rentals like strategic businesses.

Packed with real-world tactics, this episode exposes costly blind spots in operations, team structure, and revenue management you can fix now. You’ll get proven approaches for transforming your calendar into a cash-generating asset, especially with high-risk holiday traps looming in 2026.

Listen now to skip overwhelm, outmaneuver your market, and grab the edge most hosts will miss. Wait, and you risk another year of margin-sucking mistakes… These battle-tested strategies are the difference between surviving and thriving, and you won’t hear them anywhere else.

[00:00] “You’re not running a business…you’re bleeding money”—the surprising mindset shift every STR host needs

[00:05:37] How to build your dream STR team (hint: it’s way more than a cleaner and remote lock)

[00:12:40] Panic pricing exposed! Why most hosts sabotage their revenue—and the wild fix you need

[00:16:05] The “Nashville hack” for algorithm dominance—how to rewrite your listings like a pro and win more visibility

[00:18:16] The untapped event strategy: Why a board game convention can outperform the Arnold Fitness event and what it teaches about true demand

[00:19:35] Squeeze every dollar from existing bookings—transforming “dead space” in your calendar into pure profit

[00:26:33] 2026’s high-risk holidays decoded: How a Friday July 4th or Christmas can kill (or skyrocket) your revenue if you’re not prepared

[00:32:36] Why revenue managers alone won’t save you—and the critical questions smart owners must ask to beat the competition

1. Thanks for Visiting Bootcamp
2. PriceLabs Market Dashboard
3. Airbnb
4. VRBO
5. Dynamic Pricing Tools (e.g., PriceLabs)
6. Arnold Fitness Expo
7. Board Game Convention (Columbus, OH)

Sarah Karakaian and Annette Grant are co-founders of Thanks for Visiting, the revered short-term rental education brand helping thousands of hosts maximize profit and hospitality through operations excellence. As STR investors, property managers, and top trainers, they’ve coached hosts across the US to ditch hobby status, treat their rentals like real businesses, and outperform the market with data-driven, proven methods.

🔗 Website | Instagram | YouTube | LinkedIn: Sarah Karakaian | LinkedIn: Annette Grant

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 hustling for cash flow but secretly terrified of buying the wrong property? What if you’re obsessing over the wrong number… and it’s killing your returns?

In this punchy, numbers-driven solo, Kenny Bedwell (founder, STR Insights) reveals the overlooked metric that separates the real STR winners from the wannabes: ARV (After Repair Value).

He breaks down why focusing only on cash flow or gross revenue is the most common — and expensive — mistake investors make, especially as the market shifts in 2026 and beyond. Learn how the savviest investors lock in instant equity, create options, and bulletproof their portfolios… while everyone else chases hype.

Don’t wait. Listen now to avoid the pain of a dud deal and embrace an approach that gives you more freedom, flexibility, and long-term wealth. There’s no fluff here, just the data-driven truth no one else will say out loud.

[00:00] The #1 investor mistake that’s rarely talked about—are you making it?

[00:02:18] Why cash flow worship could backfire: brutal deal math exposed

[00:03:45] The California trap: when betting on appreciation costs you real money

[00:06:30] The $450k blunder: how over-improving can destroy your exit options

[00:10:17] The illusion of “winning”—when high gross revenue is secretly a loss

[00:14:21] Why 2026 will punish investors who ignore forced appreciation

[00:17:01] Case study: how to engineer instant equity and triple your exits

[00:24:47] Scouting for gold: how to spot ARV spreads in crowded markets

[00:29:47] The real goal: buying so well, operations become nearly stress-free

1. PriceLabs
2. Airbnb (smart pricing)
3. Hunter, New York (market example)

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 really leveling up or just running in circles with your real estate deals? If you’ve ever raced through a 1031 exchange, felt stuck chasing “passive” income that never arrives, or lost sleep over looming capital gains taxes, this episode is your game-changer.

Host Kenny Bedwell sits down with Brett Swarts, renowned capital gains tax strategist, for a blunt, numbers-driven masterclass on using Deferred Sales Trusts (DSTs) to crush the limitations of traditional 1031 exchanges and unleash truly passive income. Together, they dismantle common myths, reveal jaw-dropping case studies, and map out the step-by-step moves to reclaim your time, freedom, and cash flow.

Stop letting taxes and deadlines push you into the wrong deals. Listen now to discover how DSTs can hand you ultimate flexibility and real peace of mind. This exclusive episode is packed with proven strategies and insider tactics you won’t find anywhere else. Tune in now before you overpay for your next deal!

[00:00] – The moment that launched Brett’s obsession with beating capital gains taxes

[00:04:07] – Why “chasing 1031s” is making investors poor (and what to do first instead)

[00:07:45] – The “no-shoes, no-shirt, no problem” blueprint for replacing active headaches with true passive income

[00:09:19] – The killer move: How to actually “sell high, buy low” (and why 1031 jail kills your returns)

[00:12:39] – When you must set up your DST (miss this window and the tax man wins)

[00:15:31] – The shocking truth about 1031 “boot,” negotiation power, and not overpaying

[00:21:45] – Passive income math: The exact steps to multiplying your cash flow (with no toilets, trash, or termites)

[00:29:44] – How to reinvest, defer, and build wealth—without the dreaded time crunch

Brett Swarts is the founder and lead trustee at Capital Gains Tax Solutions. A nationally recognized expert in capital gains tax deferral strategies, Brett Swarts specializes in helping high net worth investors unlock growth, time freedom, and generational wealth through Deferred Sales Trusts. His practical approach has made him a trusted advisor to real estate entrepreneurs, business sellers, and anyone ready to escape the tax treadmill for truly passive income.

🔗 LinkedIn | Website

1. Building a Capital Gains Tax Exit Plan (book by Brett Swarts)
2. Build it to Billions and Give More (podcast by Brett Swarts)
3. Cash Flow Quadrant (concept from Rich Dad Poor Dad)
4. Marcus & Millichap
5. Point Loma Nazarene University
6. William Jessup University

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 scared of losing tens of thousands to the IRS on your next property sale? Wondering if a 1031 exchange is really the secret weapon for building unstoppable cash flow… or just a headache waiting to happen?

This episode, Kenny Bedwell, no-fluff educator and the data-driven mind behind STR Insights, breaks down exactly how to prepare for a 1031 exchange the right way—using numbers, timelines, and real investor mistakes. From crushing the fear of tax bills to unlocking hidden strategies for short-term rental success, Kenny’s frank approach is full of hard truths and simple steps.

Listen now to sidestep costly errors, dodge timeline traps, and discover insider tactics you won’t hear anywhere else. Miss this episode, and you risk making one of the most expensive mistakes in real estate. Tune in while the stakes are high and every dollar counts!

[00:00] The hidden 1031 pitfalls that even experienced investors miss

[00:01:14] Why “waiting until closing” could wreck your 1031 dreams

[00:02:12] The shocking impact of capital gains—the numbers that matter now

[00:03:16] How to use the IRS rules to your advantage (and avoid a nightmare)

[00:05:13] The #1 reason most investors lose money on STR furnishings

[00:07:37] The uncommon truth about 1031 down payments and boot traps

[00:11:03] Kenny’s proven equity audit method: Should you sell or wait?

[00:14:04] Mapping your cash flow and equity for a powerful portfolio move

[00:16:50] When you should start hunting for your next market (spoiler: it’s not what you think)

[00:20:46] The 60-day strategy no one is teaching for stress-free 1031 shopping

[00:22:03] The risky world of reverse 1031 exchanges—what you must know

1. STR Scale Summit (event)
2. STR Insights software
3. IRS Section 1031 (1031 exchange rules)
4. QI / 1031 Intermediary services
5. Return on Equity (ROE) audit

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 terrified of sinking your cash into a dying market or worse, following the herd off a financial cliff? In this masterclass episode, Kenny Bedwell rips the lid off his 2026 Top STR Markets Report, arming you with the real numbers, raw pitfalls, and hidden opportunities no one else will dare mention.

You’ll hear the unbiased, hard-hitting truth: where data says to buy, where strict regulations ruin even the prettiest towns, and razor-sharp strategies to squeeze maximum ROI in a landscape rocked by new rules and unpredictability. Kenny reveals not only the top 10 investable markets, but exactly why they’re worth your attention (and why some previous darlings are falling off).

Do not wait. Miss this, and you’re risking real money, real time, and watching your freedom slip away, while others secure the deals that change their financial destiny. This episode gives you numbers, biases called out, and actionable steps you won’t get anywhere else.

[00:01] – Why most “top STR market” lists are wrong (and what everyone’s missing)

[00:10] – The wild, thrilling impact of new regulations and market shakeups—this year’s biggest surprises revealed

[00:23] – Kenny’s ultra-candid red light, green light analysis: Where you really should be scared (and where to pounce)

[00:46] – The shocking climb of Mohican State Park and the overlooked cash cows in rural regions

[01:13] – Dirty little secrets behind high-grossing mountain and lake towns (and why access and permits matter more than hype)

[01:38] – Are you sitting on cash? Kenny reveals the uncommon ways budget transforms your deal-finding lens (with 4 ROI-driven categories)

[01:57] – How to beat city restrictions with region plays and advanced location hunting—no more bureaucratic land mines

[02:15] – The final, blunt warning: What happens if you listen to influencers over the data... and why you can’t skip this download

1. STR Scale Summit (event)
2. Airdna (STR market data)
3. BiggerPockets
4. Interview reference: "Part 2: How to make over $500k on one STR with Jeff Usner” episode, August/September 2024

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 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

1. AirDNA

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.

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

1. Hospitable
2. OwnerRez
3. Airbnb
4. VRBO

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.