

EP#33 Jesse Stein | Can I Airbnb My Apartment?
May 8, 2025
Jesse Stein, Global Head of Real Estate at Airbnb, dives into the complex role of short-term rentals in the housing market. He discusses how Airbnb collaborates with apartment owners, enabling residents to offer their units for short stays. Jesse touches on the misconceptions surrounding short-term rentals and their potential positive impact on housing supply. The conversation also highlights Gen Z’s preference for amenity-rich rentals and addresses the pressing need for innovative housing solutions amidst rising rents.
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Jesse Stein's Sports Journey
- Jesse Stein shares his journey from a D1 punter at Florida State to a brief NFL stint on Hard Knocks.
- His NFL career was short but a fulfilling childhood dream, eventually leading him to real estate.
Airbnb Ban Fails Housing Goals
- Overregulating Airbnb won't lower rents or increase long-term housing supply.
- More housing supply, not bans, is the true solution to housing crises.
Partnering With Apartments for STR
- Allow renters to list units on Airbnb part-time with clear rules and shared revenue.
- This partnership creates transparency, control, and a new amenity that attracts residents.