In this punchy solo episode, Kenny Bedwell, founder of STR Insights and host of Cash Flow Positive, exposes the most overhyped “STR swear words” in the business, metrics that sound good but can destroy your bottom line if you chase them blindly. You’ll learn why occupancy rate, guest ratings, and even jaw-dropping gross revenue can cost you time, money, and deal flow if you don’t dig deeper.

Don’t gamble your freedom or future on surface numbers. Listen now to dodge expensive pitfalls, outsmart the sharks, and finally see REAL cash flow. Miss this episode, and you’ll risk overpaying for duds nobody else wants to touch.

Timestamped Highlights

• 00:02 – The “STR swear words” that make Kenny Bedwell furious (and should make you nervous)
• 02:26 – The real story behind high occupancy rates—why 100% bookings can be a trap
• 04:24 – The 46% rule: How a “low” occupancy rate led to insane ROI (and less headaches)
• 06:53 – The year-round bookings myth and why chasing monthly returns kills your annual gains
• 08:00 – A 4.89-star rating, $60K more profit—what everyone gets wrong about reviews
• 10:03 – Why high bookings and high ratings still don’t guarantee cash flow (and what to demand instead)
• 13:23 – Gross revenue exposed: How sellers weaponize the most misleading metric in STR
• 16:13 – $5K “brag posts” vs. $2K net: The social media profit illusion you must avoid

Mentioned Resources

• VRBO
• Airbnb
• Facebook
• Profit & Loss statements (PNL)
• Booking Lead Time (industry trend)
• “Superhost” and Airbnb algorithm factors

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.

In this urgent solo episode, Kenny Bedwell breaks open the truth behind Airbnb’s blockbuster reversal on host fees, the quiet switch nobody was supposed to notice, but every smart investor needs to understand today.

You’ll discover what’s really behind the fee flip, how it impacts your property’s ranking and bookings, and exactly how to adapt before the window slams shut. Don’t let another booking cycle pass you by while others get ahead.

If you care about maximizing profit and avoiding algorithm disaster, you need these exclusive, data-backed strategies right now. Only Cash Flow Positive gives you the real numbers, the pitfalls, and the playbook to WIN before the changes vanish again!

Timestamped Highlights

• 00:00 – The wildest podcast cold open yet—did Airbnb really listen to this show?
• 01:45 – The “split fee” is BACK: What it means and why it matters for your profit
• 05:40 – Insider data: What happened to hosts’ bookings and income after the single fee switch
• 08:30 – Why Airbnb claims hosts get “more bookings” (and why that’s a vanity metric trap)
• 12:55 – The one move you must make in your property management system to cash in
• 17:00 – The truth about algorithm rankings and dropping your fees (what Airbnb won’t say)
• 18:40 – Top-performing properties vs. average: Who really survives policy chaos?
• 20:00 – Exactly how to prepare for June’s next pricing reset and outsmart 90% of hosts

Mentioned Resources

• VRBO (competitive shifts and booking volume)
• Airbnb Host Fee Structures (split fee vs single fee)
• Property Management Software (PMS)
• Emile Sakhel (industry revenue manager)

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.

In this can’t-miss episode, Kenny Bedwell gets brutally real with veteran broker and multi-cycle investor Ryan Cadwell, exploring why the majority of investors walk into deals blind, and what separates the survivors from the victims when markets shift. You’ll hear hard-won lessons from the Great Recession to today, the overlooked math that keeps you safe, and why your emotions are quietly sabotaging your wealth.

Stop playing checkers in a chess market. Listen now to learn the proven, data-backed playbook for winning with your exit before you ever buy. Miss this, and you’ll pay a premium for mistakes you could have avoided. Your future self is begging you not to skip these strategic insights, no fluff, zero hype, and exactly what the gurus won’t warn you about.

If you want to avoid painful losses, stop buying blind, and gain immediate edge in today’s market—this episode is your ticket. Listen now before your competition does.

Timestamped Highlights

• 00:00 – The raw mistake that nearly took down veteran investors in ‘08
• 05:12 – Why BlackRock’s latest moves are the market signal you can’t ignore
• 10:07 – How optimism bias and emotional attachment wreck your returns
• 14:19 – The 7 Whys Framework that exposes what investors really want
• 17:34 – If you LOVE a deal, why that’s your loudest red flag
• 20:17 – The data traps: Outdated numbers, ignored expenses, and the illusion of “free” vacation homes
• 25:54 – Rookie math that destroys deals and the exit-first equation that saves you
• 35:02 – The 10-minute investment journal habit that will transform your discipline (and profit)

About The Guest

Ryan Cadwell is a Certified Property Manager and Principal partner at Resolute RDM with nearly two decades of hands-on investment, development, and commercial consulting experience. Ryan’s roots go back to family rentals at age 12, spanning every market cycle from the Great Recession to post-COVID surges. He’s known for his surgical approach to due diligence, asset management, and the no-nonsense brokerage advice trusted by seasoned and rookie investors alike.

🔗 LinkedIn | Website

Mentioned Resources

• Investment Journaling (habit Ryan recommends)
• Reference to BlackRock’s market activity
• Capital expense planning/cost segregation (advanced tax and asset strategies)

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.

Host Kenny Bedwell, founder of STR Insights, reveals why most investors build backwards and sabotage their long-term wealth. This episode exposes why cash flow is not the secret, how to use data to scale faster, and the killer reason your “forever” property usually isn’t. Kenny tears down common myths, puts hard numbers behind every decision, and lays out a blueprint for achieving wealth beyond the next tax season.

Listen now and escape the newbie trap, avoid five-figure mistakes, and get the exclusive strategic insights trusted by top-performing STR investors. Your next level depends on understanding your exit, and no one else is telling you this.

Timestamped Highlights

[00:00] – Why today’s cash flow obsession is tricking investors out of real wealth

[00:38] – The “backwards builder” myth and how serial investors think differently

[02:58] – A jaw-dropping stat: Why 3–5 years is the true STR hold window

[04:20] – The ROI vs ROE showdown when selling trumps holding

[06:44] – The 1031 dilemma: Are you setting yourself up to be stuck?

[09:09] – The tax savings rabbit hole and why one year of relief kills your strategy

[11:09] – Kenny’s market-moving confession: What happens when a crowd follows your lead

[14:19] – How to spot the exact “sell trigger” (and double your portfolio wealth)

[19:02] – The trap of quantity over quality—how chasing properties makes you your own worst boss

Mentioned Resources

• 1031 Exchange strategy
• Return on Equity (ROE)
• Return on Investment (ROI)

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.

In this urgent, myth-busting episode, Kenny Bedwell sits down with revenue mastermind Emile Sakhel (Founder, Pricing by Mira) to expose the surprising ripple effects of Airbnb’s 15.5% host-only fee.

From real-world numbers to emotional guest decisions, you’ll learn exactly who’s winning and who’s losing after this game-changing shift. Discover proven tactics for protecting your net cash flow, avoiding “measurement mistakes,” and leveraging platform psychology before your next competitor.

Listen now to stop the silent drain on your profits. Avoid costly traps and get exclusive strategies you won’t hear from industry gurus or Facebook groups. This episode could mean the difference between cash flow victory and yearly regret.

Timestamped Highlights

[00:00] – Meet Emile Sakhel: The psychology (and math) of true STR profits

[00:02:37] – Airbnb’s shocking fee switch: The little-known 40% mistake sabotaging hosts

[00:04:14] – Why an 18.34% markup matters and the hidden math most hosts miss

[00:07:20] – The #1 mistake investors make when underwriting STR deals post-fee change

[00:10:09] – True or false: Did raising prices kill your ranking… or actually help?

[00:12:17] – Who’s quietly winning? The Vrbo surge nobody saw coming

[00:16:13] – Subscription secrets: How some hosts are crushing Airbnb margins on Vrbo

[00:23:17] – Price parity panic: Why guests (and algorithms) punish sloppy pricing

[00:31:19] – How to bulletproof your underwriting—get net right or get wrecked

About The Guest

Emile Sakhel is the founder of Pricing by Mira, a revenue management consultancy transforming how short-term rental operators pursue profit. Known for his deep-dive approach to revenue psychology, system building, and outperforming market RevPAR by up to 4x, Emile is a trusted educator and advisor for ambitious investors. He’s also the creator of My Revenue Academy, empowering hosts to master the art of pricing and platform strategy for themselves.

🔗 LinkedIn | Website | Facebook | Instagram

Mentioned Resources

1. My Revenue Academy
2. AirDNA
3. PriceLabs
4. RankBreeze
5. Vrbo (and “One Key” promo system)
6. DARM Conference (Data & Revenue Management)

Important Links

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.

In this data-charged episode, Kenny Bedwell breaks down the most misunderstood shift in recent STR history: Airbnb’s transfer of guest fees to hosts. If you’ve ever worried you’re charging the wrong nightly rate, or you’re blindsided by shrinking net returns despite steady bookings, you’re not alone.

With surgical clarity (and zero fluff), Kenny Bedwell reveals who actually won, who lost, and why only the savviest hosts survived. This isn’t another regurgitated news brief, it’s your exclusive masterclass on elasticity, ranking risk, and tactical pivots that could save (or sink) your STR portfolio.

Listen now to avoid sabotaging your own profits, act before your competition does, and get the unfiltered inside scoop you won’t find scrolling social or Reddit.

Timestamped Highlights

[00:00] The day everything changed: Airbnb’s shocking fee flip and what most hosts missed

[01:08] The chaos and confusion: Why hosts panicked over math and which ones got it right

[02:01] The 30/30/40 rule: Why most hosts failed to adjust and what it cost them

[05:57] The big economic reveal: Does the guest really care, or do hosts pay the highest price?

[07:09] The VRBO effect: How Airbnb’s move handed business to its rivals

[09:13] Secret algorithms: How fees, ranking, and property uniqueness now decide your fate

[11:14] Elastic vs. inelastic: Why “average” properties are at greatest risk in 2024

[15:20] How to future-proof your portfolio: Building your moat before the next big change

Mentioned Resources

1. VRBO (Vacation Rentals by Owner)
2. Ranking algorithm discussions on Airbnb

Important Links

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.

This episode will shake you out of indecision and challenge everything you thought you knew about market timing. Kenny Bedwell, founder of STR Insights, goes straight to the heart of opportunity cost, showing how hesitation can quietly devastate your wealth, your tax savings, and even your freedom.

Packed with frank, numbers-backed stories and actionable logic, Kenny breaks down why waiting for “the perfect market” is an investor’s biggest mistake and how missed months equal missed thousands. If you’re tired of guru hype and ready for practical data-driven education, tune in now. The longer you wait, the more you lose.

Listen today to avoid costly inaction and gain exclusive insight no algorithm or “expert” will give you. This episode is your wake-up call.

Timestamped Highlights

[00:00] – Why “timing the market” is just a myth (no crystal ball needed)

[00:02:42] – The shocking truth about real estate crashes and market cycles

[00:05:07] – The finite supply of “good deals” and how STR seasonality affects your shot

[00:07:18] – Real-life regret: Kenny’s confessions about not acting faster during COVID

[00:08:33] – How opportunity cost quietly steals your cash flow every missed month

[00:12:42] – Tale of two investors: Who wins and why taking action fuels exponential growth

[00:16:47] – “Ugly” puzzle properties: Why complexity signals massive upside

[00:22:17] – The secret to unlocking deals others fear (and how Kenny found a jackpot)

[00:23:30] – Kenny’s final brutal advice: Only act when you really have the means

Mentioned Resources

1. Goldman Sachs – Market rate forecast reference
2. Proper, Steadily – Insurance companies for STRs
3. Watkins Glen lottery system (STR permitting example)
4. Bonus depreciation (tax strategy for STR buyers)

Important Links

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.

Today, Kenny Bedwell pulls back the curtain on the STR Scale Summit and shares proven strategies, uncommon lessons, and hard truths from inside the event. If you crave more than generic advice, Kenny’s frank, numbers-driven breakdowns of scaling, partnerships, and real-world deal structures will give you exactly what you need.

This episode hits everything from micro resorts, boutique hotels, and creative financing, to why relationships—not just deal math—make or break your business. It’s the shortcut to avoid expensive mistakes, get access to exclusive insider tactics, and finally feel confident about scaling your STR game.

Listen now, because next year’s opportunities won’t wait, and this episode delivers practical, actionable takeaways you won’t get anywhere else.

Timestamped Highlights

[00:00] – STR Scale Summit recap: Will you be a victim of FOMO or grab your victory?

[00:01:24] – Why micro resorts are revolutionizing the cash flow game—economies of scale revealed

[00:03:15] – Inside boutique hotel investing: Real costs, real risks, and a live tour that shocked the crowd

[00:04:13] – The “whoopsie budget”—the surprising truth that blows up perfect spreadsheets

[00:05:47] – The 3 C’s of STR investing: Cute, Comfortable, Clean… and not over-amenitizing

[00:06:47] – Kenny’s “secret formula” for $100K+ cash flow properties—do you really know what to look for?

[00:07:25] – Raising capital, partnerships, and how not to get screwed—unfiltered deal structure lessons

[00:12:02] – Trust but verify: The hard rules for protecting yourself in partnerships

[00:13:08] – Why commercial lenders care about relationships more than your spreadsheets

[00:16:15] – The game-changing logistics every big investor now needs from Wayfair

[00:19:18] – Relationship ROI: Why “having a guy” beats hiring the big box company every time

Mentioned Resources

1. STR Scale Summit
2. Boutique hotel investing
3. Wayfair Professional account manager
4. BRRRR strategy
5. Commercial lending – Mark Sacco
6. 506(c) and 506(b) syndication structures

Important Links

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.

This episode, host Kenny Bedwell sits down with short-term rental powerhouse Stacey St. John, whose unique playbook has catapulted her from long-term investor to founder of a wildly impactful community and management empire. Together, they destroy myths about “minimum viable cleaning,” break down why most owners are still losing thousands, and share the real leverage hidden in systems, mindset, and (yes) the legendary “toilet test.”

If you’re serious about staying competitive, maximizing income, and avoiding industry shakeout, you need these exclusive upgrades now, not next season. Listen in for data-backed strategies that no other podcast is telling you about.

Timestamped Highlights

[00:00] – A wild Ohio-to-beach vacation trend exposes a hidden rental goldmine

[00:02:13] – COVID, eviction bans, and the shocking trigger for a rental pivot

[00:03:33] – Why oceanfront for under $100k changed everything (and you missed it…)

[00:05:08] – Accidentally creating a 66,000-member community and why it matters

[00:11:46] – The real numbers: How “clean team” upgrades spiked ratings and revenue

[00:15:34] – Cattle call cleaners, uncomfortable truths, and busting industry norms

[00:29:40] – The “toilet test” and secrets of inspection culture that make or break your reviews

[00:41:56] – Building a true team: How to transform cleaners into your STR profit weapon

Mentioned Resources

1. Female Short-Term Rental Investors Facebook Group
2. Cozy Getaways
3. Book: Live Big by Stacey St. John
4. Airbnb
5. VRBO

About the Guest

Stacey St. John is a data-driven short-term rental investor, educator, and founder of Female Short-Term Rental Investors, the largest women’s STR community with over 66,000 members. Based in Cincinnati and operating properties across Myrtle Beach and Ohio, Stacey is also CEO of Cozy Getaways, where her focus on quality, systems, and empowering women has set new industry benchmarks for guest experience and financial performance.

🔗 LinkedIn | Website | YouTube | Facebook | Instagram

Important Links

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.

In this eye-opening solo episode, Kenny Bedwell pulls back the curtain on a simple yet game-changing hack designed to bump your STR revenue by 15% (or more). Forget the tired advice about marketing and pricing. Kenny gets razor-specific about leveraging seasonality, booking lead time, and the psychology of Airbnb’s search algorithm so you can outshine saturated competition and start ranking higher, faster.

Don’t miss this episode if you’re done losing bookings to “average” listings or fighting the algorithm blind. Tune in now or risk staying buried while others claim the cash flow you deserve. This is an exclusive, numbers-driven tactic you won’t find in the usual STR playbooks!

Timestamped Highlights

[00:00] The #1 mistake hosts make that kills their revenue potential

[00:00:45] Why seasonality crushes static listing photos every time

[00:01:34] Booking lead time: the underrated, live metric that changes everything

[00:02:41] Natural disasters, “anomaly events,” and their surprising aftermath in STR bookings

[00:06:07] Want more bookings? Here’s how your photos can attract the right demand, fast

[00:07:49] The wrong photo at the wrong time: Are your snow pics scaring off summer travelers?

[00:11:01] What amenities to spotlight for instant desire in every season

[00:12:56] Christmas magic on Airbnb: the tiny photo tweak most hosts overlook

[00:14:56] How the Airbnb algorithm picks winners (and why early bookings are your lifeline)

[00:17:17] Are you overthinking seasonal photos? Kenny’s zero-fluff take on what “enough” really means

Mentioned Resources

1. Airbnb search algorithm strategies (in-episode explanation)
2. Watkins Glen property case study
3. Booking lead time analysis

Important Links

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.

In this solo episode, Kenny Bedwell gets brutally honest about the surprising ways investors lose money by overpaying, believing guru projections, and missing the “money on the buy” formula. He shreds industry misconceptions and unpacks the exact math and legal details behind ARV (After Repair Value), showing how cash flow and forced appreciation are the double-headed dragon of breakthrough investing.

Tune in now to sidestep costly mistakes, stop relying on rumors, and get exclusive, actionable clarity you won’t hear from brokers, TikTok gurus, or random Facebook groups. Listen before you make your next offer or risk losing your shot at financial freedom!

Timestamped Highlights

[00:00] – Why operating isn’t enough: The unseen risk of buying wrong

[00:01:29] – Do you really have to be a top operator, or is buying right the real unlock?

[00:03:02] – The two proven ways properties actually make money and where most get it wrong

[00:04:21] – ARV exposed: How emotional upgrades mislead you (and what counts as real value)

[00:05:35] – The appraisal rollercoaster: Millionaires or victims of ‘desk appraisals’?

[00:06:33] – Savvy investors spot the difference: How to cut through market myths

[00:10:14] – Buying at the top of the market—why every improvement becomes worthless

[00:13:31] – Legal bedroom drama: Why adding beds can blow up your deal

[00:16:49] – Pools, game rooms, and garages: What really moves the needle (and what’s a sunk cost)

[00:18:13] – Are you using the wrong comps? How one tweak can save or sink your entire investment

[00:24:25] – The price per square foot strategy: How real pros calculate ARV (step-by-step)

[00:25:30] – The 70% rule and double-headed approach: Protecting your cash flow and upside for 2026

Mentioned Resources

1. Price Per Square Foot
2. ARV (After Repair Value) Calculation
3. Legal bedroom requirements (egress window, heating, cooling, etc.)
4. Desk appraisal
5. 70% Rule
6. Cash flow and appreciation models

Important Links

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.

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.

Timestamped Highlights

[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

Mentioned Resources

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

About the Guest

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

Important Links

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.

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.

Timestamped Highlights

[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)

Mentioned Resources

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)

Important Links

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.

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.

Timestamped Highlights

[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

Mentioned Resources

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)

About the Guests

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

Important Links

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.

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.

Timestamped Highlights

[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

Mentioned Resources

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

Important Links

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.

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!

Timestamped Highlights

[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

About the Guest

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

Resources Mentioned

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

Important Links

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.

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!

Timestamped Highlights

[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

Mentioned Resources

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

Important Links

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.

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.

Timestamped Highlights

[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

Mentioned Resources

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

Important Links

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.

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.

Timestamped Highlights

[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

Mentioned Resources

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

Important Links

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.

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.

Timestamped Highlights

[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”

About the Guest

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

Resources Mentioned

1. AirDNA

Important Links

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.

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

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

Important Links

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.

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.

Timestamped Highlights

[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

About the Guest

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.

🔗 LinkedIn | Podcast | Website

Resources Mentioned

1. REIA (Real Estate Investor Association)
2. The Real Estate Investor Growth Network YouTube Channel (REIGN)

Mentioned Resources

1. The Home Depot
2. Lowe’s Home Improvement
3. Angi (formerly Angie’s List)
4. Better Business Bureau

Important Links

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.

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.

Timestamped Highlights

[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!)

Mentioned Resources

1. The Home Depot
2. Lowe’s Home Improvement
3. Angi (formerly Angie’s List)
4. Better Business Bureau

Important Links

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.

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.

Timestamped Highlights

[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

Mentioned Resources

1. Autopilot App (stock trading tool tracking politician trades)

Important Links

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.

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.

Timestamped Highlights

[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

About the Guest

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 | Facebook | Podcast | Website

Resources Mentioned

1. Crazy Love Africa – nonprofit supporting women & children in Uganda
2. Book: When Helping Hurts – teaches responsible, dignity-centered approaches to charity

Important Links

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.

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.

Timestamped Highlights

[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

About the Guest

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 Newsletter

Important Links

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.

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

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

Important Links

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.

In this episode of Cash Flow Positive, host Kenny Bedwell sits down with Tyler Gruskiewicz, a full-time real estate investor and entrepreneur from Louisville, Kentucky. Tyler shares his journey from leaving a W2 job to building a growing portfolio of STRs, boutique hotels, and vertically integrated businesses, including a cleaning company, renovation arm, and property management service, all designed to solve the pain points he faced as a host.

They dive into the mindset shifts needed to scale sustainably, the lessons learned from operational chaos, and the power of turning real problems into real opportunities. Tyler also reveals his latest project: transforming one of Kentucky’s oldest bed-and-breakfasts into a mission-driven property supporting veterans and children with speech challenges.

If you’ve ever felt “stuck” at the single-family level, this conversation will show you how to think and build bigger.

Timestamped Highlights

[00:00] Meet Tyler: From Ohio roots to full-time investor in Louisville

[01:00] Growing a 7-property STR portfolio + hotels in Florida and Missouri

[02:00] What vertical integration really looks like for real estate investors

[05:00] Faith Renovations and Signature Stays: turning problems into services

[07:00] How Tyler built cleaning, install, and property management teams

[08:30] The cleaning nightmare that pushed him to start his own company

[13:00] Why checks and balances matter in STR operations

[17:00] How one bad turnover led to a total systems overhaul

[21:00] Building culture, communication, and shared vision inside your team

[25:00] The importance of purpose-driven leadership

[29:00] Turning early check-ins into new revenue and guest satisfaction

[32:00] The story behind Kentucky’s oldest B&B—and how it became a mission

[36:00] Giving back to veterans and kids through real estate

[40:00] The takeaway: No one’s coming to save you—build the solution yourself

About the Guest

Tyler Gruskiewicz is a real estate investor known for owning several short-term rental properties in Kentucky with a proven track record in the short-term rental (STR) market. He has gained recognition through interviews and podcasts for his unique approach to growing wealth through STR investments, highlighting both the challenges and strategies for success in this niche real estate segment.​ In addition to his property investments, Gruskiewicz also owns and operates a renovation and cleaning company, leveraging his experience to support and scale his rental business. Recently, he expanded his real estate portfolio by purchasing a 29-door hotel in Branson, Missouri, indicating significant growth and diversification in his hospitality ventures.

🔗 LinkedIn | Website

Important Links

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.

In this episode of Cash Flow Positive, host Kenny Bedwell breaks down what it truly takes to grow beyond single-family short-term rentals and why the definition of “scaling” should be unique to every investor.

Kenny walks through his personal evolution from duplex house hacking to managing multi-unit portfolios, building a co-hosting business, and partnering with investors to acquire large-scale STRs and boutique hotels.

Along the way, he shares the mindset, strategies, and lessons that help hosts move from buying one property at a time to building a sustainable, scalable business model that fits their goals, not social media’s definition of success.

Timestamped Highlights

[00:00] Why “scaling” looks different for every STR owner

[00:01:00] Kenny’s early investing story, from house hacking to Airbnb

[00:04:45] How Buffalo, NY shaped his mindset on scaling and diversification

[00:06:30] Breaking through capital limitations with rental arbitrage

[00:09:00] The rise (and fall) of arbitrage and what works better now

[00:10:30] Scaling into co-hosting and property management

[00:11:45] The power of sharing your wins to attract partnerships

[00:13:40] How to start small but think like a business owner

[00:15:20] Diversifying across markets for long-term stability

[00:18:00] Leveraging other people’s money (OPM) to scale faster

[00:20:20] Building partnerships and equity deals with no capital invested

[00:22:00] Why hotels aren’t the only way to scale and how big STRs can outperform

[00:24:00] Choosing properties that match your goals, not trends

[00:25:15] The truth about hotel deals vs. high-performing STRs

[00:26:40] Redefining success and scaling on your own terms

[00:27:50] A look ahead: scaling through new business opportunities

Resources Mentioned

1. Launch Hosts by Kim Fitzpatrick - Example of scaling through services

Important Links

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.

In this episode of Cash Flow Positive, Kenny Bedwell digs into the “curse” of review-driven real estate—how guest expectations, property condition, and first impressions can quietly make or break your returns. He breaks down the two sides of STR investing (real estate + hospitality), shares real-world examples from his own portfolio, and explains why operations and guest experience are just as critical as deal analysis.

You’ll learn what details guests really notice, how to find properties that support great reviews from day one, and the simple fixes that turn complaints into five-star ratings.

If you want your short-term rental to outperform the market, hit play and start thinking like a guest, not just an investor.

Timestamped Highlights

[00:00] Why Kenny “hates” reviews 4and how they shape investor behavior

[01:00] The two-headed monster of STR investing: real estate + hospitality

[02:30] Why being a great host directly impacts revenue

[04:00] How property age and updates influence guest satisfaction

[06:00] Lessons from a historic 1860s home that became a five-star stay

[09:00] The hidden cost of ignoring capital expenditures

[10:40] When old systems (like HVAC) destroy the guest experience

[12:00] How unfinished basements and outdated designs kill reviews

[15:20] External factors: neighbors, privacy, roads, and power lines

[20:00] Designing for privacy, accessibility, and comfort

[23:00] How to impress guests from the moment they arrive

[25:00] The power of small touches, like Kenny’s ice cream bar idea

[27:00] Why first impressions make or break your ratings

[30:20] The link between five-star reviews and long-term revenue

Important Links

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.

If you’ve been chasing the next “get rich quick” shortcut in real estate… this episode is your reality check.

In this episode of Cash Flow Positive, Kenny Bedwell flips the script on fast money and exposes the truth about building real wealth through real estate. He shares insights from conversations with high-level investors: Those who buy $100M hotels and still play the long game and reveals why the biggest wins come from appreciation, tax strategy, and equity paydown, not just monthly cash flow.

You’ll learn the four true pillars of wealth in real estate, how to think like an investor instead of a speculator, and why repositioning your assets the right way can transform your portfolio faster than chasing short-term returns ever will.

Stop looking for overnight success. Press play now to learn how the smartest investors actually get rich with patience, data, and a long-term plan.

Timestamped Highlights

[00:00] Back from the flu and fired up about “get rich quick” myths

[01:30] The problem with chasing only cash flow

[03:35] Lessons from top-tier investors who buy $100M properties

[05:00] The four wealth pillars: cash flow, appreciation, tax savings, and equity paydown

[07:00] What “repositioning” really means and why it’s where wealth is built

[09:25] When cash flow should be your priority and when it shouldn’t

[10:30] Why high-income professionals invest differently (and what that means for you)

[12:30] How to calculate true ROI using total return, not just cash flow

[15:20] The mindset shift: stop chasing income, start building net worth

[18:30] Defining your investment goals before you buy your next STR

[21:15] How Kenny evaluates deals now and why forced appreciation beats “good enough”

Important Links

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.

In this episode of Cash Flow Positive, Kenny reveals a deal-finding strategy he’s seen quietly pay off in competitive short-term rental markets: targeting properties with extra square footage and converting them into higher bedroom counts. From Sedona to the Poconos, Kenny explains why “heads in beds” is the #1 revenue driver, how to legally add bedrooms to force appreciation, and why average-performing STRs will always lose out to top properties.

You’ll hear how to spot these overlooked opportunities, the math that makes them work, and why moving quickly under contract is often the difference between landing a deal and watching it slip away.

Don’t settle for average returns. Press play now to learn how Kenny turns overlooked listings into high-cash-flow, high-appreciation wins.

Important Links

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.

In this episode of Cash Flow Positive, Kenny Bedwell sits down with veteran mortgage broker and STR financing expert Matt Stout. With over 32 years of lending experience and thousands of deals funded, Matt pulls back the curtain on when refinancing actually makes sense. From dropping interest rates and shifting housing trends to creative ways to redeploy “dead equity” into higher cash-flowing properties, this episode delivers the unvarnished truth about refinancing in today’s market.

You’ll learn the right (and wrong) reasons to refinance, how to weigh costs versus cash flow, and why keeping versus selling a property can make or break your long-term wealth.

Don’t guess your way through one of the biggest financial decisions you’ll face as an investor. Press play now to get Kenny and Matt’s proven framework for knowing when to refinance and how to use it to build real generational wealth.

About the Guest

Matt Stout is “The STR Loan Guy” and founder of Consumers Financial, a mortgage brokerage licensed in 48 states. With over three decades in lending and a personal background in real estate investing, Matt specializes in STR and DSCR loans that help investors unlock equity and scale their portfolios. He’s known for creative lending strategies, hybrid loan solutions, and his straight-shooting approach to helping investors win deals.

🔗 STR Loan Guy Website | YouTube – STR Loan Guy | Facebook | TikTok @thestrloanguy

Important Links

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.

In this episode of the Cash Flow Positive Podcast, host Kenny Bedwell is joined by Erin Wegrzyn, a real estate consultant with STR Insights, to explore exactly that scenario. Together, they break down how to choose the right markets, set realistic expectations, and avoid the “amenities arms race” that eats into cash flow.

Erin shares her journey from long-term rental investor to short-term rental specialist and why her strategy has shifted toward properties that both cash flow and create memories for her family. Kenny and Erin discuss how to research markets, stay ahead of competitors, and build a property that can grow with the market over time, without burning out or over-renovating.

If you've enjoyed this episode of the Cash Flow Positive podcast, be sure to leave a review and subscribe today! Listen now and enjoy!

Key takeaways:

1. How to choose markets without spreading yourself too thin
2. Why being “one of one” in a market is a huge advantage
3. How to avoid competing in an endless amenities war
4. What to look for in properties that allow for future upgrades
5. Why following where large investors are putting money can reveal emerging markets
6. The best way to build a reliable local team of contractors and cleaners
7. Why you should visit and experience a market before you invest there
8. And much more...

Guest Bio:

Erin Wegrzyn is a real estate consultant with STR Insights, where she helps investors analyze markets and identify profitable short-term rental opportunities. Based in Kentucky, she brings firsthand experience as an investor and a deep understanding of market trends, property selection, and building reliable local teams. Erin is passionate about helping clients choose properties that cash flow, grow in value, and fit their lifestyle goals.

Important Links

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.

Disclaimer:

The views, information, or opinions expressed during this podcast are solely those of the individuals involved and do not necessarily represent those of the Cash Flow Positive podcast or its affiliates. The content provided is for informational and entertainment purposes only and is not intended to be a substitute for professional advice. We make no representations as to the accuracy, completeness, suitability, or validity of any information on this podcast and will not be liable for any errors, omissions, or delays in this information or any losses, injuries, or damages arising from its display or use. Listeners should consult with a professional for specific advice tailored to their situation. By accessing this podcast, you acknowledge that any reliance on the content is at your own risk.

In this episode of Cash Flow Positive, Kenny Bedwell pulls back the curtain on exactly how he’d put that money to work in short-term rentals. He breaks down why your financing strategy can make or break a deal, the five cost buckets most investors forget about, and why setting your ROI goal up front is non-negotiable.

You’ll hear Kenny think through real markets, from Florida beaches to Shenandoah cabins, and explain how to spot which ones fit your budget and which ones will bleed you dry.

Don’t guess your way into a $250K mistake. Hit play now to hear Kenny’s no-fluff, data-backed roadmap and get clarity on where your money will actually cash flow.

Timestamped Highlights

[00:00] How a $250K windfall changes your investing strategy overnight

[02:14] The financing trap that torpedoes deals before they close

[04:18] The five hidden costs every STR investor must budget for

[07:36] Kenny’s minimum ROI goals—and why cash flow beats percentages

[10:53] The “process of elimination” method for picking your markets

[14:25] Why Bradenton, FL, might work—and the brutal barrier to entry

[21:00] Shenandoah’s low-barrier charm vs. beach market competition

[24:38] How lakefronts in Michigan and urban rentals in Cincinnati stack up

Resources

1. STR Insights software
2. Top Markets Report (via STR Insights website)
3. Dave Ramsey podcast (benchmark reference)
4. Zillow & Redfin (for market comps)

Important Links

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.

In this episode of the Cash Flow Positive Podcast, Kenny Bedwell sits down with Rachel Gniady, full-time real estate investor and STR Insights consultant, to talk about how the new 15.5% host fee is reshaping underwriting, deal selection, and long-term strategy.

Rachel shares how she is being even more conservative with revenue estimates, why she is rejecting deals that don’t have a wide enough margin, and why being “one of one” in a market is more important than ever. Together, Kenny and Rachel dive into moats, market trends, appraisals, and the importance of thinking like an investor first, even as competition heats up and the “middle” of the STR market gets squeezed.

Want to keep spotting high-margin STR deals even as fees climb? Listen now and sharpen your strategy. If you've enjoyed this episode of the Cash Flow Positive podcast, be sure to leave a review and subscribe today! Listen now and enjoy!

Key takeaways:

1. Why Airbnb’s fee change demands more conservative underwriting
2. How to evaluate properties with a “good, better, best” revenue approach
3. Why being unique in your market protects your profits
4. The dangers of chasing trends and how to know when to walk away
5. Why comps, cost basis, and appraisals matter more than ever
6. How to protect yourself in today’s “Wild West” real estate market
7. Why stability can beat higher short-term returns in the long run
8. The importance of making offers quickly and confidently
9. And much more...

Guest Bio:

Rachel Gniady is a full-time real estate investor and consultant for STR Insights, where she has helped over 50 clients close deals and build profitable short-term rental portfolios. Based in New Orleans, she has nearly 20 years of experience buying, improving, and selling properties.

Resources:

Part 2: Finding High ROI STR Deals with No Money with Rachel Gniady

Connect with Rachel on LinkedIn

Important Links

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.

Disclaimer:

The views, information, or opinions expressed during this podcast are solely those of the individuals involved and do not necessarily represent those of the Cash Flow Positive podcast or its affiliates. The content provided is for informational and entertainment purposes only and is not intended to be a substitute for professional advice. We make no representations as to the accuracy, completeness, suitability, or validity of any information on this podcast and will not be liable for any errors, omissions, or delays in this information or any losses, injuries, or damages arising from its display or use. Listeners should consult with a professional for specific advice tailored to their situation. By accessing this podcast, you acknowledge that any reliance on the content is at your own risk.

In this episode of the Cash Flow Positive podcast, Kenny Bedwell breaks down the shift from a split-fee model to a single-host fee of 15.5%. He explains what this really means for your payouts, why simply raising your rate isn’t the answer, and how the wrong pricing strategy could tank your rankings and bookings.

Kenny walks through the math behind the change, why some hosts will be hit harder than others, and what you can do to protect your bottom line. From understanding price elasticity to planning ahead with discounts and direct bookings, this episode is packed with insights and strategies you won’t want to miss.

Don’t let Airbnb’s new fee structure cut into your earnings. Tune in to learn the smart strategies that keep your payouts strong.

If you've enjoyed this episode of the Cash Flow Positive podcast, be sure to leave a review and subscribe today! Listen now and enjoy!

Key takeaways:

1. Why raising your prices could hurt your rankings
2. How pricing without a strategy leaves you vulnerable to underpriced competitors
3. Why cookie-cutter properties are more exposed than unique listings
4. The exact percentage increase needed to maintain your current payouts
5. Why timing your price adjustments can affect your Airbnb search rankings
6. How to think about cause and effect when responding to platform changes
7. And much more...

Important Links

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.

Disclaimer:

The views, information, or opinions expressed during this podcast are solely those of the individuals involved and do not necessarily represent those of the Cash Flow Positive podcast or its affiliates. The content provided is for informational and entertainment purposes only and is not intended to be a substitute for professional advice. We make no representations as to the accuracy, completeness, suitability, or validity of any information on this podcast and will not be liable for any errors, omissions, or delays in this information or any losses, injuries, or damages arising from its display or use. Listeners should consult with a professional for specific advice tailored to their situation. By accessing this podcast, you acknowledge that any reliance on the content is at your own risk.

In this episode of the Cash Flow Positive podcast, Kenny Bedwell continues his deep dive into the reasons most people miss out on profitable real estate deals. Building on Part 1’s discussion of vision and creating a moat, Kenny highlights three more critical factors that separate average investors from top performers: acting fast, knowing your guest avatar, and truly understanding what makes a property special in its market.

Through real-world examples, Kenny shows why hesitation, personal bias, and limited knowledge often cost investors life-changing opportunities. This episode is a practical roadmap to spotting hidden value and moving with confidence when great deals appear.

If you've enjoyed this episode of the Cash Flow Positive podcast, be sure to leave a review and subscribe today! Listen now and enjoy!

Key takeaways:

1. Why hesitation and “analysis paralysis” cause investors to miss out on deals
2. The importance of acting fast while protecting yourself with contingencies
3. How top investors use due diligence periods to secure multiple opportunities
4. Why buying for personal preference instead of guest demand leads to missed deals
5. How understanding your “guest avatar” reveals what drives revenue in each market
6. Why many investors fail simply because they don’t know what to look for
7. How to elevate a property’s value by adding design, decor, and amenities
8. The difference between a natural moat and a completed moat — and how to build one
9. And much more...

Important Links

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.

Disclaimer:

The views, information, or opinions expressed during this podcast are solely those of the individuals involved and do not necessarily represent those of the Cash Flow Positive podcast or its affiliates. The content provided is for informational and entertainment purposes only and is not intended to be a substitute for professional advice. We make no representations as to the accuracy, completeness, suitability, or validity of any information on this podcast and will not be liable for any errors, omissions, or delays in this information or any losses, injuries, or damages arising from its display or use. Listeners should consult with a professional for specific advice tailored to their situation. By accessing this podcast, you acknowledge that any reliance on the content is at your own risk.

In this episode of the Cash Flow Positive Podcast, Kenny Bedwell breaks down the number one reason most people miss out on great real estate deals: a lack of vision. Using real-world examples, including a six-bedroom Montana property overlooked by more than ten investors, Kenny illustrates how the best opportunities often require foresight, creativity, and the willingness to see potential where others only see problems.

From the concept of building a “moat” that sets your property apart, to understanding why people default to safe, turnkey investments, Kenny shows how successful investors think differently. Discover how one investor turned a rejected Montana property into a top-performing STR.

If you've enjoyed this episode of the Cash Flow Positive podcast, be sure to leave a review and subscribe today! Listen now and enjoy!

Key takeaways:

1. Why most investors fail to recognize the potential in overlooked properties
2. The importance of having vision when evaluating deals
3. How to identify and build a “moat” that separates your property from the competition
4. Why great deals often come in the form of outdated or overlooked homes
5. How one investor turned a rejected Montana property into a cash-flowing success story
6. Why copying turnkey models is short-term thinking, and how long-term strategies create real wealth
7. And much more...

Important Links

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.

Disclaimer:

The views, information, or opinions expressed during this podcast are solely those of the individuals involved and do not necessarily represent those of the Cash Flow Positive podcast or its affiliates. The content provided is for informational and entertainment purposes only and is not intended to be a substitute for professional advice. We make no representations as to the accuracy, completeness, suitability, or validity of any information on this podcast and will not be liable for any errors, omissions, or delays in this information or any losses, injuries, or damages arising from its display or use. Listeners should consult with a professional for specific advice tailored to their situation. By accessing this podcast, you acknowledge that any reliance on the content is at your own risk.

Kyle shares his hands-on approach to finding undervalued properties, forcing appreciation, and navigating the emotional roller coaster of major renovation projects. From choosing the right markets to building reliable teams, Kyle explains how smart planning and execution can eliminate risk and create life-changing financial wins.

Want to know how pros turn rundown homes into cash-flow machines? Hear the infinite return model explained step by step in this episode. Don’t just buy another property—discover the strategy that pays you back in full and keeps paying you forever.

If you've enjoyed this episode of the Cash Flow Positive podcast, be sure to leave a review and subscribe today! Listen now and enjoy!

Key takeaways:

1. Why having “boots on the ground” is invaluable for successful real estate projects
2. How to budget realistically and prepare for surprises in renovation projects
3. The emotional side of investing and why big returns require taking calculated risks
4. Why eliminating risk comes down to working with the right people and running the right numbers.
5. How to find the best markets for forcing equity and long-term gains.
6. Kyle’s coaching insights on what makes the infinite return model sustainable.
7. And much more...

Guest Bio:

Kyle Powers is a Top Producing Agent from Manhattan, Kansas, ranking in the top 5% of Realtors with over 400 homes sold in just 8 years. Beyond sales, he invests in long-term and short-term rentals, house flips, and co-founded The Elevated Realtors, where he trains agents to scale their businesses.

Resources:

Connect with Kyle on LinkedIn

Connect with Kenny on LinkedIn

Follow Kenny on Instagram

Important Links

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.

Disclaimer:

The views, information, or opinions expressed during this podcast are solely those of the individuals involved and do not necessarily represent those of the Cash Flow Positive podcast or its affiliates. The content provided is for informational and entertainment purposes only and is not intended to be a substitute for professional advice. We make no representations as to the accuracy, completeness, suitability, or validity of any information on this podcast and will not be liable for any errors, omissions, or delays in this information or any losses, injuries, or damages arising from its display or use. Listeners should consult with a professional for specific advice tailored to their situation. By accessing this podcast, you acknowledge that any reliance on the content is at your own risk

Kenny explains how this strategy works in both short-term rentals and larger projects, including his own experience renovating a hotel in New Orleans. From understanding appraisals and refinancing to leveraging other people’s money, this episode offers practical insights into achieving truly infinite returns in real estate.

Don’t just buy another property. Learn the strategy that can give you returns with no money left in the deal. If you've enjoyed this episode of the Cash Flow Positive podcast, be sure to leave a review and subscribe today! Listen now and enjoy!

Key takeaways:

1. What the infinite return model is and why it matters in real estate investing
2. How to force appreciation through renovations or strategic value-add projects
3. The role of appraisals, refinancing, and financing options in pulling money back out of a deal
4. Why short-term rentals are uniquely positioned for infinite returns
5. How building or renovating with short-term rentals in mind creates long-term advantages
6. Kenny’s real-world hotel investment example and how it demonstrates this model in action
7. And much more...

Important Links

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.

Disclaimer:

The views, information, or opinions expressed during this podcast are solely those of the individuals involved and do not necessarily represent those of the Cash Flow Positive podcast or its affiliates. The content provided is for informational and entertainment purposes only and is not intended to be a substitute for professional advice. We make no representations as to the accuracy, completeness, suitability, or validity of any information on this podcast and will not be liable for any errors, omissions, or delays in this information or any losses, injuries, or damages arising from its display or use. Listeners should consult with a professional for specific advice tailored to their situation. By accessing this podcast, you acknowledge that any reliance on the content is at your own risk.

Kenny explains why unique property characteristics, “Wow” spaces, and smart upgrades can make your listing nearly impossible for competitors to match. He also discusses how to identify undervalued opportunities, keep expenses down, and plan for long-term profitability, all while staying laser-focused on guest experience.

If you've enjoyed this episode of the Cash Flow Positive podcast, be sure to leave a review and subscribe today! Listen now and enjoy!

Key takeaways:

1. Why the most successful properties have attributes that competitors can’t easily replicate
2. How to identify and enhance unique characteristics in your property
3. The role of “Wow” spaces in boosting bookings and enhancing guest satisfaction
4. Why keeping expenses low is just as powerful as finding undervalued deals
5. How Kenny applies his own “Crusher Competition” strategy to make his Airbnbs unbeatable
6. And much more...

Resources:

The Strategy That Makes My Airbnbs Impossible to Compete With

Important Links

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.

Disclaimer:

The views, information, or opinions expressed during this podcast are solely those of the individuals involved and do not necessarily represent those of the Cash Flow Positive podcast or its affiliates. The content provided is for informational and entertainment purposes only and is not intended to be a substitute for professional advice. We make no representations as to the accuracy, completeness, suitability, or validity of any information on this podcast and will not be liable for any errors, omissions, or delays in this information or any losses, injuries, or damages arising from its display or use. Listeners should consult with a professional for specific advice tailored to their situation. By accessing this podcast, you acknowledge that any reliance on the content is at your own risk.

In this episode of the Cash Flow Positive podcast, Kenny Bedwell shares hard-earned insights from his latest experiences in the field and on stage at the STR Wealth Conference. Drawing from real client case studies, personal portfolio wins, and lessons learned from analyzing hundreds of STRs, Kenny emphasizes one core principle: if you want to stand out, you need to do what 95% of people won’t, or can’t do.

Whether it’s investing in an unconventional niche, buying undervalued properties with built-in equity, or avoiding oversaturated markets that everyone’s rushing into, this episode offers a blueprint for smarter decision-making. Kenny doesn’t just talk numbers, he dives deep into mindset, strategy, and the critical difference between copying a great idea and creating one.

You will walk away with a sharper understanding of what makes an STR truly resilient and why now, more than ever, real estate investing requires bold moves and creative thinking. If you’ve been sitting on the sidelines or unsure where to focus your next property search, this episode will give you the urgency and clarity to act.

If you've enjoyed this episode of the Cash Flow Positive podcast, be sure to leave a review and subscribe today! Listen now and enjoy!

Key takeaways:

1. Why you shouldn’t wait until fall to start searching for STR properties
2. The 95% rule and how to apply it to your next investment
3. What it really means to have a moat and how to create one
4. How to spot undervalued properties with instant equity
5. Why copying a good deal isn’t the same as creating one
6. What investors are getting wrong in oversaturated markets
7. The biggest mistake Kenny sees when hosts chase cash flow alone
8. How to structure your next deal to survive any dip in revenue
9. And much more...

Important Links

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.

Disclaimer:

The views, information, or opinions expressed during this podcast are solely those of the individuals involved and do not necessarily represent those of the Cash Flow Positive podcast or its affiliates. The content provided is for informational and entertainment purposes only and is not intended to be a substitute for professional advice. We make no representations as to the accuracy, completeness, suitability, or validity of any information on this podcast and will not be liable for any errors, omissions, or delays in this information or any losses, injuries, or damages arising from its display or use. Listeners should consult with a professional for specific advice tailored to their situation. By accessing this podcast, you acknowledge that any reliance on the content is at your own risk.

Madeline shares her insights from both the agent and investor perspective, offering practical advice on preparing a property for listing, managing guest experience during the transition, and understanding the realities of today’s saturated market. From the importance of budgeting and inspections to the value of patience and honesty, this conversation is a candid and informative guide for anyone considering selling an STR.

If you've enjoyed this episode of the Cash Flow Positive podcast, be sure to leave a review and subscribe today! Listen now and enjoy!

Key takeaways:

1. Why budgeting upfront for guest experience can make or break your STR’s performance
2. How to coach your clients for STR success before listing
3. Why a bad cleaner can hurt your reviews—and your ability to sell
4. The importance of routine inspections and functional appliances
5. Why pre-listing inspections are crucial in today’s competitive market
6. When it might be wiser to take a loss and move on
7. How to make executive decisions based on your unique situation
8. The value of leaning on local resources and being adaptable
9. Why honesty—from yourself and your agent—is key to success
10. Why patience is a necessary mindset in a slow market
11. And much more...

Guest Bio:

Madeline Blum is a real estate agent and short-term rental investor with properties in multiple markets, including the Smoky Mountains, North Carolina, the Bourbon Trail, and Panama City Beach. With experience on both sides of the deal, she brings a strategic, investor-savvy approach to buying, selling, and managing STRs—always focused on creating long-term value and delivering exceptional service.

Resources:

Follow Madeline on Instagram

Follow Madeline on Facebook

Important Links

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.

Disclaimer:

The views, information, or opinions expressed during this podcast are solely those of the individuals involved and do not necessarily represent those of the Cash Flow Positive podcast or its affiliates. The content provided is for informational and entertainment purposes only and is not intended to be a substitute for professional advice. We make no representations as to the accuracy, completeness, suitability, or validity of any information on this podcast and will not be liable for any errors, omissions, or delays in this information or any losses, injuries, or damages arising from its display or use. Listeners should consult with a professional for specific advice tailored to their situation. By accessing this podcast, you acknowledge that any reliance on the content is at your own risk.

You’ll learn what documents to gather, how to estimate your property’s value, what buyers are really looking for, and how to present your property in the most attractive light. Kenny also explains common mistakes to avoid, like underestimating how much your property is worth or ignoring the emotional aspects of the sale.

Thinking of selling your short-term rental? Don’t list it before you listen to this episode. Kenny breaks down how to prep your STR like a pro—from documents and value estimates to buyer psychology and profit strategy. Whether you’re weeks or years away from a sale, this episode will help you exit smart.

If you've enjoyed this episode of the Cash Flow Positive podcast, be sure to leave a review and subscribe today! Listen now and enjoy!

Key takeaways:

1. The importance of keeping your data clean and organized
2. How to estimate your property’s value based on market context
3. What information to include in a property packet for buyers
4. Why making your listing “look like a business” boosts its appeal
5. The emotional side of selling a property and how to prepare for it
6. Common pitfalls sellers face when trying to exit
7. How to communicate the true potential of your STR to investors
8. And much more...

Important Links

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.

Disclaimer:

The views, information, or opinions expressed during this podcast are solely those of the individuals involved and do not necessarily represent those of the Cash Flow Positive podcast or its affiliates. The content provided is for informational and entertainment purposes only and is not intended to be a substitute for professional advice. We make no representations as to the accuracy, completeness, suitability, or validity of any information on this podcast and will not be liable for any errors, omissions, or delays in this information or any losses, injuries, or damages arising from its display or use. Listeners should consult with a professional for specific advice tailored to their situation. By accessing this podcast, you acknowledge that any reliance on the content is at your own risk.

Beata shares her insights on how to approach STR design with both strategy and creativity. She explains how functionality, guest experience, and budget-conscious decisions can come together to elevate your listing above the competition. The conversation covers everything from curating standout features and maximizing ROI to managing vendors and understanding what guests really want.

Whether you're just starting out or looking to refresh your existing rental, Beata’s practical tips and candid advice will help you rethink what it takes to build a high-performing property. Learn the subtle tweaks and smart differentiators that actually move the needle, and start creating unforgettable guest experiences that don’t break the bank.

If you've enjoyed this episode of the Cash Flow Positive podcast, be sure to leave a review and subscribe today! Listen now and enjoy!

Key takeaways:

1. The value of being different in the STR market
2. How to compete without investing in expensive amenities
3. Ways to create comfort and immersive experiences on a budget
4. Tips for identifying what your market is missing—and offering that
5. Why unexpected guest features can create memorable stays
6. How to evaluate competitors and strategically stand apart
7. The mindset shift required to break away from industry trends
8. How to create your own playbook in the short-term rental space
9. And much more...

Guest Bio:

Beata Lorinc is a North Carolina licensed Realtor, the owner of a boutique luxury full-service property management firm, and a trusted consultant for busy professionals. With a sharp eye for potential, she specializes in transforming ordinary homes into high-performing short-term rentals. Drawing from over a decade of experience at Procter & Gamble in supply chain and customer service—combined with years of hands-on success in property design, vendor management, and guest relations—Beata delivers strategic solutions that help hosts thrive in a competitive market.

Resources:

TheBoutiquePM.com

Important Links

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.

Disclaimer:

The views, information, or opinions expressed during this podcast are solely those of the individuals involved and do not necessarily represent those of the Cash Flow Positive podcast or its affiliates. The content provided is for informational and entertainment purposes only and is not intended to be a substitute for professional advice. We make no representations as to the accuracy, completeness, suitability, or validity of any information on this podcast and will not be liable for any errors, omissions, or delays in this information or any losses, injuries, or damages arising from its display or use. Listeners should consult with a professional for specific advice tailored to their situation. By accessing this podcast, you acknowledge that any reliance on the content is at your own risk.

Drawing from his own experience and industry data, Kenny explains why success in STR doesn’t always mean high capital investment. Instead, it starts with understanding your goals, the dynamics of your market, and how guests make decisions. He walks listeners through the difference between traditional vacation rental markets and emerging STR-friendly areas, revealing how location, expectations, and regulations can influence your strategy more than a hot tub or a game room ever could.

Whether you’re just entering the STR game or reassessing your investment strategy, this episode will help you focus your efforts—and your budget—where it matters most.

If you've enjoyed this episode of the Cash Flow Positive podcast, be sure to leave a review and subscribe today! Listen now and enjoy!

Key takeaways:

1. What super amenities are—and when they actually matter
2. The key question to ask before investing in an STR
3. Why guest expectations are lower in some markets (and how that can help you)
4. How to identify whether your market demands extra investment
5. The risks and rewards of operating in regulation-prone areas
6. Why location may be more important than luxury
7. And much more...

Important Links

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.

Disclaimer:

The views, information, or opinions expressed during this podcast are solely those of the individuals involved and do not necessarily represent those of the Cash Flow Positive podcast or its affiliates. The content provided is for informational and entertainment purposes only and is not intended to be a substitute for professional advice. We make no representations as to the accuracy, completeness, suitability, or validity of any information on this podcast and will not be liable for any errors, omissions, or delays in this information or any losses, injuries, or damages arising from its display or use. Listeners should consult with a professional for specific advice tailored to their situation. By accessing this podcast, you acknowledge that any reliance on the content is at your own risk.

From bonus depreciation strategies to qualifying for deductions, Ryan explains how to navigate evolving tax laws while building a resilient investment portfolio. Whether you're investing in short-term rentals, midterm stays, or traditional long-term properties, this conversation is packed with insights to help you make smarter financial moves.

You’ll also hear Ryan's perspective on how government incentives are structured to stimulate the economy and why timing is everything when structuring your deals. Curious how the new tax bill could impact your real estate strategy?

Before you lock in your next deal, hit play on this episode with CPA Ryan Bakke. You’ll walk away with smarter ways to approach depreciation, deductions, and portfolio planning in today’s shifting economy.

If you've enjoyed this episode of the Cash Flow Positive podcast, be sure to leave a review and subscribe today! Listen now and enjoy!

Key takeaways:

1. How government tax policy is designed to drive economic growth
2. What types of real estate properties qualify for bonus depreciation
3. The key question you need to ask before deducting depreciation against your income
4. Why planning ahead is critical despite future legal uncertainties
5. How waiting to act on deals could cost you more and limit your negotiating power
6. Which tax updates indirectly impact short-term rental operators
7. And much more...

Guest Bio:

Ryan Bakke is a licensed CPA and the founder of Tax Strategy 365, where he helps real estate investors build generational wealth using the tax code. A Trinity Christian College graduate in Accounting and Finance, Ryan began his career at Deloitte, where he led tax technology initiatives for major investment banks. He’s also a former high-level athlete and passionate Christian servant leader.

Resources:

Connect with Ryan on LinkedIn

Apply for 2025 tax strategy

The Ryan Bakke Podcast

Join the Tax Strategies For Real Estate Investors Group on Facebook

Important Links

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.

Disclaimer:

The views, information, or opinions expressed during this podcast are solely those of the individuals involved and do not necessarily represent those of the Cash Flow Positive podcast or its affiliates. The content provided is for informational and entertainment purposes only and is not intended to be a substitute for professional advice. We make no representations as to the accuracy, completeness, suitability, or validity of any information on this podcast and will not be liable for any errors, omissions, or delays in this information or any losses, injuries, or damages arising from its display or use. Listeners should consult with a professional for specific advice tailored to their situation. By accessing this podcast, you acknowledge that any reliance on the content is at your own risk.

In this episode of the Cash Flow Positive podcast, Kenny Bedwell sits down with design expert and STR consultant Becky Jones to unpack how design, comfort, and guest experience all connect to your bottom line.

Becky explains how she balances aesthetics with function to attract better guests, command higher nightly rates, and reduce property issues. From managing remodels to optimizing guest comfort, this episode is packed with actionable advice to make your short-term rental more profitable—and less stressful.

If you've enjoyed this episode of the Cash Flow Positive podcast, be sure to leave a review and subscribe today! Listen now and enjoy!

In This Episode You'll Learn:

1. How to approach design with a photo-first mindset to increase bookings
2. Why well-designed rooms can raise your nightly rate and reduce guest complaints
3. The real impact of design on guest behavior—and your stress level
4. Why high-end finishes attract higher quality guests
5. How market research and guest avatars influence design decisions
6. What to watch for when coordinating design with remodeling timelines
7. Why spending more upfront can actually save you time and money later
8. And much more...

Guest Bio:

Becky Jones is an interior designer specializing in designing short-term rentals that are functional, beautiful, and profitable, and founder of Becky Jones Branding. Known for her visual-first approach and guest-centric design strategies, Becky helps STR owners elevate their properties through thoughtful upgrades that enhance comfort, increase profitability, and create memorable guest experiences.

Resources:

BeckyJonesBranding.com

Follow Becky on Instagram

Follow Becky on Facebook

Important Links

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.

Disclaimer:

The views, information, or opinions expressed during this podcast are solely those of the individuals involved and do not necessarily represent those of the Cash Flow Positive podcast or its affiliates. The content provided is for informational and entertainment purposes only and is not intended to be a substitute for professional advice. We make no representations as to the accuracy, completeness, suitability, or validity of any information on this podcast and will not be liable for any errors, omissions, or delays in this information or any losses, injuries, or damages arising from its display or use. Listeners should consult with a professional for specific advice tailored to their situation. By accessing this podcast, you acknowledge that any reliance on the content is at your own risk.

In this solo episode of Cash Flow Positive, Kenny Bedwell reveals why the speed of your short-term rental launch is one of the most critical—and commonly overlooked—factors in maximizing profit. He shares a personal story of how delays during the design process cost him thousands in holding fees and lost revenue, and walks listeners through how to avoid making the same mistake.

Kenny breaks down the real financial impact of slow timelines, how to vet designers for efficiency and market alignment, and why identifying your guest avatar should come before any décor decisions. You’ll also learn how to communicate clearly with designers, set firm expectations, and ensure your property is not just beautiful, but bookable.

Whether you're launching your first STR or scaling a portfolio, this episode will shift the way you think about design, timelines, and how to protect your bottom line from the start.

Ready to turn design delays into revenue wins? Subscribe now and discover more strategies that make your STR cash flow faster. If you've enjoyed this episode of the Cash Flow Positive podcast, be sure to leave a review. Listen now and enjoy!

In This Episode You'll Learn:

1. Why launching quickly is crucial to maximizing STR profitability
2. How holding costs during the design phase can hurt your returns
3. What to ask your designer before hiring them
4. Why timelines, clarity, and accountability matter more than you think
5. How to ensure your designer incorporates what actually attracts guests to your area
6. The danger of creating generic, forgettable spaces that appeal to no one
7. How to ensure your designer reflects what actually draws guests to your area
8. And much more…

Important Links

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.

Disclaimer:

The views, information, or opinions expressed during this podcast are solely those of the individuals involved and do not necessarily represent those of the Cash Flow Positive podcast or its affiliates. The content provided is for informational and entertainment purposes only and is not intended to be a substitute for professional advice. We make no representations as to the accuracy, completeness, suitability, or validity of any information on this podcast and will not be liable for any errors, omissions, or delays in this information or any losses, injuries, or damages arising from its display or use. Listeners should consult with a professional for specific advice tailored to their situation. By accessing this podcast, you acknowledge that any reliance on the content is at your own risk.

In this episode of the Cash Flow Positive podcast, Kenny Bedwell welcomes Merritt, founder of Merit Badge Property Management, to dive into the business of creating standout STRs through interactive amenities, ROI-driven design, and a deep understanding of what guests actually want. From his no-nonsense approach to systems and team leadership to the design decisions that impact bookings, Merit shares a wealth of practical insights for property owners and managers alike.

Whether you’re co-hosting a few properties or scaling a management business, this conversation will inspire you to think bigger and design smarter.

If you've enjoyed this episode of the Cash Flow Positive podcast, be sure to leave a review and subscribe today! Listen now and enjoy!

In This Episode You'll Learn:

1. Why design and amenities must go beyond aesthetics to actually drive revenue
2. How to evaluate your property as an experience, not just a place to stay
3. What makes a listing “sticky” and how that affects your nightly rate
4. Why most designers miss the mark on interactive ROI
5. How Merit approaches team management with outcomes—not micromanagement
6. The importance of systems in building a scalable STR business
7. How to identify design strengths and expand creatively without losing cohesion
8. And much more...

Guest Bio:

Merritt Haris is the founder of Merit Badge Property Management, where he helps short-term rental owners increase revenue and create unforgettable guest experiences through strategic design and streamlined operations. Known for his bold mindset and system-driven approach, Merit is passionate about empowering clients and team members alike to live their “best life” while building a thriving STR business.

Resources:

Merit Badge Property Management

Follow Merit on Facebook

Follow Merit on Instagram

Follow Merit on TikTok

Important Links

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.

Disclaimer:

The views, information, or opinions expressed during this podcast are solely those of the individuals involved and do not necessarily represent those of the Cash Flow Positive podcast or its affiliates. The content provided is for informational and entertainment purposes only and is not intended to be a substitute for professional advice. We make no representations as to the accuracy, completeness, suitability, or validity of any information on this podcast and will not be liable for any errors, omissions, or delays in this information or any losses, injuries, or damages arising from its display or use. Listeners should consult with a professional for specific advice tailored to their situation. By accessing this podcast, you acknowledge that any reliance on the content is at your own risk.