“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 that 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 seen, and it’s driven my passion,” Wacksman said. “It’s what led me to Zillow and it’s honestly what keeps me at Zillow.”
Zillow declined to share additional comment to Fortune.
One of the most pivotal moments for the $17 billion real-estate marketplace came shortly after Wacksman joined the business as the VP of marketing and product: Apple was finally taking websites mobile with apps for the iPhone.
“I wasn’t hired to [help the company go mobile], I was hired to work on the product and marketing efforts. But mobile was new, and I said yes,” Wacksman said. “And in many ways, my career was just 15 years of saying yes to the next thing.”
Reflecting on his time at Zillow and the many other ‘yes’ moments he’s committed to, Wacksman said he’s learned to embrace opportunity. There will be times that projects fall through or unexpected challenges come into the fold, but the experiences make for a better leader.
“You’ll throw yourself into something and it’ll work, or you’ll throw yourself into something and it won’t work,” Wacksman said. “You’ll have to pivot, but you’ll have learned something.”
