Part 1: Scaling beyond single family homes

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

• Launch Hosts by Kim Fitzpatrick - Example of scaling through services

Important Links

• Want us to find the deals for you? https://strinsights.com
• Get Top Markers for STRs (2025) https://www.strinsights.com/top-investable-short-term-rental-markets-2025-report
• 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 and Podcast Your Brand. Production and editing by Podcast Your Brand.