November 25, 2025

I Walked Away From My W-2 at 47 (Here’s What Happened) | Jeremy DeGrasse

44 minutes

Ever wonder what it really takes to walk away from a steady W2 and reinvent your life in real estate and short-term rentals?

In this episode, host Jason Muth sits down with Jeremy De Grasse for an honest, inside look at how they each stepped out of corporate careers and built thriving businesses in the stunning Adirondacks. Together, they dive into the lessons learned the hard way, the juggling act of family and entrepreneurship, the importance of scaling with intention, and how tools like Host Buddy can transform your operations.

If you’re dreaming about your own career shift or looking to grow your rental portfolio, their candid conversation is packed with inspiration, insights, and real-world advice to help you shape your next chapter.

Things we discussed in this episode:

Transitioning from W2 jobs to running real estate/short-term rental businesses.
Challenges and strategies of scaling a business in your 40s versus hustle culture in younger environments.
Inspiration and lessons from the Adirondacks and Lake Placid for property ownership and building.
The partnership between Jeremy and his wife Nicole in operating Drifter Stays, dividing outward and operational responsibilities.
Importance of balancing business ambitions with family life and personal legacy.
Letting go of clients and properties that don’t fit the business’s goals to maintain reputation and reduce stress.
The significance of intentionality and system-building as the business grows.
Adoption and testing of AI-driven tools like Host Buddy for automating guest communications.
The journey and challenges involved in hiring virtual assistants to support business operations.
Practical advice for mid-career professionals on making a successful transition to a new venture.

Get in touch with Spencer:

Instagram - ⁠⁠⁠https://www.instagram.com/drifterstays/

Facebook - ⁠⁠⁠⁠⁠https://www.facebook.com/drifterstays

Website - ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://www.drifterstays.com/

#SmartStayShow #realestate #realestateinvestor #realestateagent #RealEstateInvesting #ShortTermRentals #CareerChange #EntrepreneurLife #MidlifeReinvention
#BusinessGrowth #PropertyManagement #FamilyBusiness #AIAutomation #WorkLifeBalance

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By Airbnb Superhost Jason Muth + Rory Gill

4.9

4040 ratings