From Wall Street to Vacation Rentals: A Banker’s Exit Strategy

The transition began as a side hustle. While Chang worked as an M&A banker and his wife, Elizabeth, pursued a career in fashion at Kate Spade, the couple began listing apartments on Airbnb. By 2018, the income from these rentals—often netting $6,000 in monthly cash flow per unit—provided enough leverage to leave the high-stakes world of finance behind. The move was not without risk; the COVID-19 pandemic nearly shuttered their operation, forcing them to navigate significant financial strain before pivoting to property ownership in the Smoky Mountains.

Today, Chang operates a mentorship business, STR like the Best, which has guided over 100 clients through the complexities of real estate investment. While he acknowledges the intellectual loss of working alongside top-tier CEOs, the trade-off is measurable in time rather than capital. This summer, he is spending seven weeks in Taiwan with his children—a level of family involvement he asserts would have been impossible under the rigid scheduling of his former career. For Chang, the shift represents a reclamation of his calendar, moving from a role optimized for a firm's bottom line to one structured around personal freedom.