In this episode of the STR Data Lab, Jamie Lane interviews Hailie Anderson, founder of Airbnb Takeoff, about her journey in the short-term rental (STR) industry. Hailie, joining live from the Philippines, shares how she began her entrepreneurial journey at 19 during the COVID-19 pandemic. She graduated early from school and initially ran a content creation agency. Influenced by TikTok videos about rental arbitrage, she started her venture at 19, acquiring her first three units.

Fast forward to now at 22, she has expanded to 58 units. Hailie explains the rental arbitrage model, noting it as a legitimate business strategy that allows property management sans ownership. She discusses her approach, which includes cold calling and emailing landlords to gain leasing agreements. Hailie also elaborates on the challenges and misconceptions of rental arbitrage, emphasizing the importance of legal and ethical operations. She highlights the critical role of building reliable local teams and leveraging technology, including PMS, dynamic pricing, and guest verification software. Hailie’s tech stack includes various tools like Price Labs, Hostaway, and True V to streamline operations.

Moreover, she emphasizes the importance of understanding market differences and stresses on the entrepreneurial spirit of Gen Z, which she believes is characterized by boldness, a desire for fast ROI, and a passion for digital nomadism. Jamie and Hailie also debate the value of education from social media and the differences between Gen Z and older generations’ approaches to investment and risk.

Hailie concludes by sharing her future plans, which include possibly expanding her portfolio further, staying in hospitality, and investing in properties for long-term stability. She encourages listeners to start pursuing their passions, emphasizing that success often comes from learning, failing, and trying repeatedly.