Cash Flow Positive

What if your “unique” short-term rental is actually invisible… and costing you thousands? Steph Weber joins Kenny Bedwell to unpack the brutal disconnect between what most STR and boutique hotel owners think is a brand, and what truly drives guest loyalty, market differentiation, and higher ADR. From confusing “luxury” with actual value to the real reason guests rebook through Airbnb, you’ll learn...

Are you quietly losing thousands by ignoring your rental’s brand? In this punchy solo episode, Kenny Bedwell cuts through the noise and exposes why branding is not just logos or pretty fonts. Right now, as Airbnb changes the rules again and hosts are questioning their dependence on big platforms, building your own brand is your only edge. You’ll get a direct, step-by-step breakdown of Kenny’s thre...

Are your Airbnb investments sabotaging your wealth before you even realize it? In this episode, Kenny Bedwell delivers a blunt reality check for tax-savvy short-term rental investors chasing bonus depreciation and “easy” write-offs. He exposes the #1 mistake even experienced buyers keep repeating: letting potential tax savings override every other investing principle. You’ll hear why treating your...

What if the only thing standing between you and rapid portfolio growth isn’t money, but mindset and strategy? Kenny Bedwell drills into the raw realities of leveraging Other People’s Money (OPM) to explode your short-term rental business, exposing what actually works and what will quietly kill your progress. Whether you have time but no capital, or capital with no time, he details the only partner...

What if the three things holding back your short-term rental revenue are hiding in plain sight? Kenny Bedwell, data-driven investor and STR educator, breaks down the amenities most investors miss, ones that are scientifically proven to spike your bookings and cash flow fast. Forget the gimmicks and “guru” advice. In this brutally practical episode, you’ll hear real numbers, tactical breakdowns, an...

Are you prepared for the Airbnb landscape to feel brutally different this summer? Kenny Bedwell, founder of STR Insights and numbers-driven host of Cash Flow Positive, pulls back the curtain on the truth behind short-term rental trends and the shifting power moves that will make or break your returns in 2026. In this hard-hitting episode, Kenny Bedwell reveals why stabilization is here, what “prof...

Ever lost thousands simply by trusting the wrong process or the wrong person? Kenny Bedwell returns from a break not just with fresh life perspective but with the hard-won, painful truths of renovating an 1848 boutique hotel from hundreds of miles away. This episode dives deep into the exact mistakes that cost him actual cash, and even more valuable time from contractor sequencing chaos to shipmen...

Are you stuck grinding but never really escaping? In this punchy solo episode, Kenny Bedwell drops the curtain on the two proven secrets that transformed his own portfolio, and he does not sugarcoat the realities. With sharp stories of scrappy beginnings, W2 frustration, and the gut-check moment that forced him to choose between comfort and growth, Kenny Bedwell dives deep into the real reasons in...

Are your short-term rentals sitting empty while your competitors rake in bookings? You might be targeting the wrong guest without even knowing it. In this tough-love, numbers-driven solo episode, Kenny Bedwell, founder of STR Insights, reveals the six REAL buyer personas that drive every booking decision and why most hosts get it dead wrong. Cut through the industry fluff: This episode breaks down...

Are you obsessed with high booking rates, glowing reviews, or six-figure revenue? What if those metrics are secretly keeping you broke and blind to your property’s true potential? 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 i...

Are your Airbnb profits slipping and you don’t know why? Imagine waking up to a revenue model change that could make or break your short-term rental business. 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 re...

Ever wondered why real estate investors lose big while others exit with effortless wins? 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 t...

Are you racing to buy more properties but never stopping to ask, “What’s my end game?” If you want true financial freedom from short-term rentals—not just another job—you need a proven, numbers-driven exit plan. 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 us...

Is your short-term rental income safe, or is the new Airbnb fee model slashing profits behind your back? Most hosts have no idea how much they’re really losing or why Vrbo is suddenly on the rise. 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...

Are you leaving hidden cash on the table after Airbnb’s dramatic fee overhaul or, worse, losing it without knowing? 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,...

in a short-term rental? 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...

Ever wonder why some real estate investors explode their portfolios while others fumble with endless spreadsheets? 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 stru...

Ever worry that one bad cleaning review could shatter your STR returns or even threaten your bookings? Imagine systematically boosting your ratings, delighting guests, and generating reliable cash flow, all simply by revolutionizing your approach to quality and teams. This episode, host Kenny Bedwell sits down with short-term rental powerhouse Stacey St. John, whose unique playbook has catapulted...

Are your short-term rental photos quietly costing you thousands in lost revenue? Most hosts lock in their listing photos and hope for the best, but what if a single, data-backed tweak could drive a double-digit leap in bookings? 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 ti...

Are you tired of the hype, confusion, and conflicting advice dominating short-term rental investing? What if the real secret to real estate freedom isn’t just how you operate, but how you buy? 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 indust...

Are you stuck waiting for the “big crash” to finally buy your dream short-term rental? What if that crash already came…and left you behind? In this radically honest episode of Cash Flow Positive, host Kenny Bedwell brings on industry powerhouse Avery Carl for an unfiltered look at the post-pandemic real estate landscape. Avery Carl pulls from 10+ years and 5,000+ deals to reveal why smart investor...

Are you sick of recycled guru advice and worried about making the wrong move in today’s wild STR market? Kenny Bedwell cuts through the noise with brutal honesty and stark data, giving you the freedom to say no to hype and yes to cash-flow-positive deals. In this punchy solo episode, he dives into the real state of the industry for 2026: how incentives twist advice you hear, why copycat “hotspots”...

When’s the last time your calendar made you real money? Most hosts set their pricing, cross their fingers, and hope the bookings roll in… all while leaving thousands on the table and letting holidays sabotage their revenue. In this actionable episode, Kenny Bedwell sits down with powerhouse educators Annette Grant and Sarah Karakaian from Thanks for Visiting to unpack how “mom and pop” operators c...

Are you hustling for cash flow but secretly terrified of buying the wrong property? What if you’re obsessing over the wrong number… and it’s killing your returns? In this punchy, numbers-driven solo, Kenny Bedwell (founder, STR Insights) reveals the overlooked metric that separates the real STR winners from the wannabes: ARV (After Repair Value). He breaks down why focusing only on cash flow or gr...

Are you really leveling up or just running in circles with your real estate deals? If you’ve ever raced through a 1031 exchange, felt stuck chasing “passive” income that never arrives, or lost sleep over looming capital gains taxes, this episode is your game-changer. Host Kenny Bedwell sits down with Brett Swarts, renowned capital gains tax strategist, for a blunt, numbers-driven masterclass on us...