Cash Flow Positive

Winter Is Coming for Short-Term Rentals: How to Get More Bookings During Slow Season Winter is approaching, and for most short-term rental owners, that means fewer bookings, increased competition, and a tougher battle to keep occupancy up. But the hosts who prepare now could have a major advantage over those who wait until their calendars are empty. In this episode of Cash Flow Positive , Kenny Be...

Seller Financing Isn't Cheap: The Mistakes That Could Cost You Thousands Seller financing sounds like a great opportunity. No traditional bank, flexible loan terms, and potentially lower interest rates. But what happens when those attractive terms hide a property that's overpriced? In this episode of Cash Flow Positive , Kenny Bedwell breaks down the opportunities and risks of seller financing, ex...

Airbnb's New Rules: How to Protect Yourself Legally as a Host Airbnb's latest policy changes have short-term rental hosts asking some serious questions. While everyone seems focused on the new rules around guest chores, there's a much bigger issue that could put hosts at risk: restrictions on rental agreements and guest verification. In this episode of Cash Flow Positive , Kenny Bedwell sits down...

Why would a successful short-term rental investor start buying long-term rentals again? In this episode of Cash Flow Positive , Kenny Bedwell shares why he's expanding his long-term rental portfolio, including a new quadplex under contract near Buffalo, New York, and how his investment strategy has evolved as his portfolio has grown. Kenny isn't walking away from short-term rentals. Instead, he's...

Interest Rates Are High. Should You Still Buy Short-Term Rentals? Higher interest rates are making short-term rental deals harder to find, but that doesn't mean opportunities have disappeared. In this episode of Cash Flow Positive , Kenny Bedwell breaks down how rising borrowing costs are affecting returns, why buying now and hoping to refinance later can be risky, and how investors can protect th...

I Bought a 14-Room Hotel: What I Wasn't Prepared For Kenny Bedwell finally has his 14-room boutique hotel in downtown New Orleans open to guests. But getting there was anything but simple. In this episode of Cash Flow Positive , Kenny pulls back the curtain on the project and shares the challenges, mistakes, delays, and unexpected lessons that came with buying and renovating a historic hotel in th...

How Much Cash Do You Really Need to Buy an STR? How much cash do you actually need to buy a short-term rental? It’s a question Kenny Bedwell gets all the time, and the answer has changed dramatically as the STR industry has become more competitive. In this episode of Cash Flow Positive , Kenny breaks down what it really takes to invest in a short-term rental today, why STRs have become a much more...

Stop Asking Me What the Best STR Markets Are “What are the best markets to invest in?” It’s one of the most common questions Kenny Bedwell gets asked. But as the short-term rental industry has become more professional and competitive, that question has become much harder to answer. In this episode of Cash Flow Positive , Kenny explains why there is no single list of “best markets” that works for e...

Stop Adding Amenities. Build a Better Moat. If your short-term rental isn't getting enough bookings, your first instinct might be to add something new. A pickleball court. A hot tub. An Xbox. An espresso machine. Whatever the competition seems to have. But what if that's the wrong question? In this episode of Cash Flow Positive , Kenny Bedwell breaks down why constantly adding amenities isn't nece...

Data Over Hype: How to Make Smarter STR Investment Decisions As the short-term rental industry matures, competition is increasing not just among property owners, but among the vendors, influencers, services, and businesses built around the industry. In this episode, Kenny Bedwell takes a closer look at what happens when markets stabilise and competition increases, and why that can lead to more hyp...

How the Pros Get Real Estate Deals Done Faster One of the biggest things holding real estate investors back isn't a lack of good deals. It's analysis paralysis. In this episode, Kenny Bedwell breaks down how experienced investors approach offers differently and why making an offer doesn't have to mean making a hard commitment. Instead, the offer is the beginning of the due diligence process, givin...

Why I’m Not Buying More Airbnbs Right Now What if buying another Airbnb isn’t actually the best move for your portfolio? In this episode, Kenny Bedwell explains why he has paused his Airbnb acquisitions after years of building and growing his short term rental portfolio. But that doesn’t mean he’s done buying Airbnbs. Instead, Kenny breaks down why successful investing is about knowing what your p...

What are the real foundations of a successful real estate investment? There’s a lot of conflicting advice online about what matters most when investing in real estate. Some investors swear by cash flow, others chase appreciation, and others focus heavily on tax savings. But according to Kenny Bedwell, the answer isn’t as simple as picking one. In this episode, Kenny goes back to the fundamentals a...

Should Tax Savings Drive Your Next Airbnb Investment? With bonus depreciation back at 100%, many investors are once again rushing into short-term rentals to reduce their tax bills. But is chasing tax savings enough to make a property a good investment? In this episode, Kenny Bedwell and Ryan Bakke, CPA, discuss how investor behavior has changed since the return of full bonus depreciation. They exp...

How do you grow an Airbnb from barely breaking even to one of the most wish listed properties in your state? Janelle Gallucci joins Kenny Bedwell to share how she transformed a struggling Lake Tahoe Airbnb into one of the highest performing properties in Nevada. Starting with a property that barely covered its mortgage, she reveals the strategies that helped grow annual revenue from $25,000 to $16...

What does it actually take to become one of the highest earning Airbnb properties in your market? In this episode, Kenny Bedwell shares the strategies behind one of Kentucky's top performing short term rentals and explains why success is about much more than adding expensive amenities. From choosing the right market to understanding exactly who your property is designed for, he walks through the f...

This episode outlines how AI can be utilized within a short-term rental (STR) business, based on insights from Kenny Bedwell. Core Philosophy on AI AI as a Tool: AI is an evolving tool that requires a competent human driver to function effectively. Address Bottlenecks: Rather than building "cool" tech for the sake of it, use AI to solve specific business problems, bottlenecks, or time-consuming ma...

To analyze short-term rental (STR) deals in 2026, it is essential to recognize the professionalization of the industry, which requires higher standards for design, amenities, and overall property quality. Key strategies for effective deal analysis include: Move Beyond Geographic Analysis: Analyzing revenue solely based on a property's immediate geographic radius or comparable listings is often sho...

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...