Cash Flow Positive

Latest episodes

Showing 20 · updated from the feed

Seller Financing Isn’t Cheap Money

Seller Financing Isn't Cheap: The Mistakes That Could Cost You ThousandsSeller financing sounds like a great opportunity. No traditional bank, flexible loan terms, and po

Nov 5
29 min

Navigating the legal side of Airbnb's new terms and conditions

Airbnb's New Rules: How to Protect Yourself Legally as a HostAirbnb's latest policy changes have short-term rental hosts asking some serious questions. While everyone see

Oct 29
44 min

I’m Buying Long-Term Rentals Again—Here’s Why

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 hi

Oct 22
29 min

How 7%+ interest rates change my investing strategy

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 opportunit

Oct 15
29 min

I Bought a 14-Room Hotel. Here’s What I Wasn’t Prepared For

I Bought a 14-Room Hotel: What I Wasn't Prepared ForKenny Bedwell finally has his 14-room boutique hotel in downtown New Orleans open to guests. But getting there was any

Oct 8
22 min

How Much Cash Do You Really Need to Buy an STR?

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 an

Oct 1
26 min

Stop Asking, “What’s the Best Airbnb Market?”

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-te

Sep 24
25 min

You don't need another amenity. You need a moat.

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.

Sep 17
22 min

Data Over Hype - What to Watch Out For

Data Over Hype: How to Make Smarter STR Investment DecisionsAs the short-term rental industry matures, competition is increasing not just among property owners, but among

Sep 10
24 min

How the pros get deals done

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

Sep 3
27 min

I stopped buying Airbnbs! Here's why

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

Aug 25
22 min

The Foundations of Real Estate Investing

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. S

Aug 20
24 min

Common Mistakes Investors Are Making in 2026

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 t

Aug 6
45 min

Part 2: How to become the #1 wish listed property on Airbnb

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 transf

Jul 30
38 min

Part 1: How to become the #1 wish listed property on Airbnb

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 Kent

Jul 28
27 min

How I Use AI in My Airbnb Business

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

Jul 23
34 min

How I'm Analyzing Deals in 2026

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, amenit

Jul 16
30 min

Part 2: Build your brand

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 mo

Jul 9
43 min

Part 1: Build Your Brand

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

Jul 7
18 min

Every Tax Savvy Airbnb Investor Makes This HUGE Mistake

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 ren

Jun 30
24 min

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What listeners say

A curated, balanced selection of Apple Podcasts reviews.

Kenny is definitely one of the best in the industry, constantly working to improve things for not only his clients at STR Insights but also every investor he meets. He pushes all his partners and peers to raise the level of service for short term rental investors in a way that few others do. Love the podcast!

Tylercoon2010 · Apr 2025

Kenny is the master at breaking down the most important items for making you successful with your STR investment. Nobody has the breadth of knowledge he has as an operator and advisor or insight into so many markets. Thank you for sharing your knowledge Kenny!

MichaelK03 · Apr 2025

Kenny does a great job of providing valuable information for both beginners and seasoned STR investors alike!

Sabres Coach · Apr 2025

I love Kenny’s Podcast. He is data-driven, leads with real time market trends, and provides concise, actionable, and insightful content. If you’re new or just actually want to remain successful and relevant, you should have this podcast in your queue.

Luxury Rental Podcast · Apr 2025

We strive to present a balanced view by showing a diverse range of reviews from Apple Podcasts.