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- From High Income Tech Director to Full Time STR Investor & CEO of Crafted Stays - Gil Chan
From High Income Tech Director to Full Time STR Investor & CEO of Crafted Stays - Gil Chan
Summary
Gil Chan shares his experiences as a short-term rental host with properties in the Smoky Mountains and Branson, Missouri. He emphasizes the importance of heavily investing in platforms like Airbnb, VRBO, and Booking.com during the initial years and starting to build a direct booking engine in year two, while also discussing marketing tactics and tax advantages.
More from Growth & Marketing

Countries are simplifying visa processes to attract Indian tourists, a rapidly growing outbound tourism market. France is offering visa-free airport transit and simplifying visa procedures for students, while Armenia allows visa-free entry for Indian passport holders with valid permits. These developments could indirectly boost STR demand in these destinations.
Airbnb introduces Reserve Now, Pay Later, allowing guests worldwide with moderate or flexible cancellation policies to book without immediate payment. This flexibility, already successful in the U.S., targets group trips and budget-conscious travelers, driven by new data showing demand for flexible payment options in Asia Pacific. This innovation complements existing payment options to boost bookings.
This Skift article highlights Airbnb's experimental airport pickup service, raising speculation about potential future ventures. The platform's expansion beyond accommodations may signal a broader move into travel services, possibly including flights. This could significantly impact the STR landscape by integrating transportation and lodging.
Curated by Learn STR by GoStudioM



