Welcome to our latest episode! Today, we’re joined by Jason Muth, Co-Founder and Director of Customer Experience at Prideaway Stays. Jason is a 31x Airbnb Superhost, 29x Vrbo Premier Host, and a full-time entrepreneur who transitioned from a corporate media career to scaling a successful short-term rental and co-hosting business. His story is filled with insights on intentional growth, hospitality, and building a business that aligns with your lifestyle and values.

In this episode, Jason shares how one uncomfortable couch and an allergy to cats led to the purchase of his first short-term rental in 2016—and how that one home turned into five owned properties and a thriving co-hosting operation with 17 listings. He walks us through the lessons learned from a major property flood, why having the right insurance partner made all the difference, and how installing generators across his portfolio became a strategic move. Jason also unpacks the launch of Prideaway Stays, his Provincetown-focused management company that blends hospitality, niche branding, and community engagement.

If you’re curious about how to pivot into co-hosting, build a business that reflects your values, or simply hear how a seasoned host navigated the challenges of growth, this episode is for you. Tune in now to learn how Jason scaled from one rental to a robust hospitality brand—and what he wishes more short-term rental owners understood about success!

TIMESTAMPS

01:00 – Spring updates and business expansion

04:58 – Guest intro: Jason Muth

06:08 – How an uncomfortable couch sparked Jason’s first short-term rental

09:05 – From one rental to five: Jason’s early investment journey

13:28 – Transitioning from W-2 to full-time entrepreneur

17:00 – Using DSCR and vacation loans to scale

19:11 – Cost segregation and maximizing depreciation

22:01 – The guest-caused flood and $130K in damages

24:50 – Why proper insurance is worth every penny

29:14 – Installing generators across all properties

31:03 – Messaging guests and preparing for power outages

33:36 – Neighbor relationships and protecting the business

39:02 – Launching Prideaway Stays in Provincetown

42:55 – Why niche focus matters: Knowing your target guest

48:03 – Second homeowners vs. investors in New England markets

50:47 – Giving back and community partnerships at Prideaway

53:45 – Final thoughts and where to connect with Jason

Connect with the Guest:

Website: https://www.prideawaystays.com/

Linkedin: https://www.linkedin.com/in/jasonmuth/

Instagram: https://www.instagram.com/jasonmuth/

Facebook: https://www.facebook.com/jasonmuth/

Youtube: https://www.youtube.com/@smartstayshow

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