What does “scaling” really mean for you?

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.