Craig Rashkow: Family Values with Professional Excellence
From Keynotes by Casago by Steve Schwab
August 29, 2025 · 16 min · Episode 21
About this episode
Craig Rashkow discusses his transition to managing Vacasa markets under the Casago franchise model and shares insights on improving homeowner and guest experiences.
Transforming Vacation Home Management with Craig Rashkow: Introducing the Casago Franchise Model In this episode of Keynotes, host Steve Schwab speaks with Craig Rashkow, a seasoned professional in the hospitality industry, about his recent transition to managing several Vacasa markets under the Casago franchise model. Craig shares his journey from working in operational roles to entering the vacation rental industry with Sonder and Roofstock. Emphasizing local support and personalized service, Craig discusses his vision for improving homeowner and guest experiences through better technology and operational practices. He also highlights the importance of community and interpersonal relationships in successful property management. Listen in to learn about the operational changes and improvements Craig plans to implement as part of the Casago team. Reach out to Craig at *1-312-504-3462* or *craig.rashkow@roofstock.com* 00:00 Welcome to Keynotes with Steve Schwab 00:54 Meet Craig: A Journey in Hospitality 01:56 Transition to Casago: What Homeowners Need to Know 03:42 Building Strong Local Teams 05:31 Craig's Personal Touch: Family and Music 07:03 Operational Improvements for…
People in this episode
Host: Steve Schwab
Guest: Craig Rashkow
Topics covered
- Vacation Home Management
- Franchise Model
- Hospitality Industry
- Operational Improvements
- Community Relationships
- Technology in Property Management
Keywords
- vacation rentals
- property management
- franchise
- hospitality
- local support
- operational practices
- community
- technology
Mentioned in this episode
Organizations: Casago, Vacasa, Sonder, Roofstock
Places: Chicago
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