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

The 2008 financial crisis burned bad memories into the back of Americans’ brains: employees being laid off in droves, families struggling to put food on their tables, and a housing market in peril. 

But Zillow’s CEO, Jeremy Wacksman, says the time was the start of a new beginning. Less than one year later, he ditched his job as a marketing and product manager at Microsoft Xbox to join the real estate startup, despite nervous looks from his friends. 

“Back in early 2009, for those that remember, [it] was not a fantastic real estate market,” Wacksman told Fortune in a 2025 Leadership Next podcast episode. 

“I remember talking to friends and family [that] I was going to leave a job at Microsoft…And they were like, ‘Why are you going to go work for this money-losing real estate startup? Real estate’s a terrible market.’”

The Gen Xer explained his marketing degree is what got him the job at Microsoft—but also, what inspired him to ultimately leave. 

“Building a product and then getting that product ever-present in the user’s mind, that’s been the common theme I’ve see...