Zillow’s CEO says his friends were shocked when he quit a cushy Microsoft job—but Steve Jobs led to his success at the $10.5 billion real estate firm

April 19, 2026 - 02:56

In a move that stunned his inner circle, Jeremy Wacksman walked away from a secure, high-paying career at Microsoft in 2009. He left to join Zillow, then a fledgling and struggling online real estate platform in the throats of a historic housing market collapse. To his friends, it seemed an inexplicable risk.

Wacksman recently reflected on that pivotal decision, crediting an unexpected source for the courage to leap: the late Apple co-founder, Steve Jobs. He recalled Jobs's famous Stanford commencement speech, particularly the exhortation to "stay hungry, stay foolish." That philosophy resonated deeply, convincing Wacksman that the greater risk was in staying put in a comfortable role, potentially missing the chance to build something transformative.

His gamble paid off spectacularly. Wacksman, now Zillow's CEO, helped steer the company through its turbulent early days into a dominant force. Under his leadership, Zillow has evolved far beyond simple listings into a comprehensive real estate marketplace, influencing how millions buy, sell, and finance homes. The company's current market valuation stands as a testament to that early, faith-driven decision, proving that sometimes the most foolish-seeming path leads to the most substantial success.