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Zillow Group CEO Spencer Rascoff interviews theBoardlist founder Sukhinder Singh Cassidy for his ‘Office Hours’ podcast at the 2017 GeekWire Summit in Seattle. (Photo by Dan DeLong for GeekWire)

As the co-founder of Hotwire and CEO of Zillow Group, with stints at companies like TPG Capital and Expedia, Spencer Rascoff has had a successful career by many standards.

That’s why it was interesting to hear him talk about his keys to success on a recent podcast hosted by Business Insider reporter Alyson Shontell aptly named “Success! How I Did It.”

Rascoff, who co-founded travel booking website Hotwire in 1999 and was the original chief marketing officer at real estate giant Zillow Group in 2005, shared several stories about his career path during the 30-minute conversation. For example:

  • Rascoff was a nationally-ranked chess player while in grade school — “I played every weekend hardcore,” he noted.
  • Rascoff grew up in an affluent environment and didn’t experience much grit. That changed when his 17-year-old brother died in a car accident just before graduating high school. “When you lose your brother at an early age, all of a sudden you’re sort of jolted into just a different world,” he said. “Those last couple of years of high school, I kind of felt like I had to really overachieve, and I worked really hard and am still working really hard 25 years later.”
  • Hotwire faced serious adversity two years after launching. There was the dot-com bubble and the 9/11 tragedy kept many people from traveling. To make matters worse, the 9/11 hijackers used Hotwire to buy tickets to Bangor, Maine, before they flew from Bangor to Logan International. Rascoff also lost a family friend on the plane that went down in Pennsylvania; he also traveled on the United 93 Newark to San Francisco flight just a few days before. Hotwire went through big layoffs, but the core team stuck together and “worked our butts off to make Hotwire successful,” Rascoff said. It sold to Expedia for $700 million two years later.
  • Rascoff faced similar struggles when Zillow went through layoffs during the 2008 housing crash. “It was the same thing: It was cut deep and recommit the remaining employees to the mission,” he said. “In both cases, the adversity that Hotwire and Zillow faced, there was a silver lining, it turns out. It made both companies much stronger as a result, and I don’t think Zillow would have been as successful today had it not been for the adversity that we faced in ’07 and ’08.”
  • Now that Rascoff runs a $7 billion company in Zillow, he’s had to change his leadership style. “You have to take seriously this reflection that for every person at the company, you need to think about, ‘Is that the right person for the next two years in the role?'” he said.
Zillow CEO Spencer Rascoff and Facebook COO Sheryl Sandberg
Zillow CEO Spencer Rascoff and Facebook COO Sheryl Sandberg. (Zillow Photo)

Asked about his success and advice for others, here’s what Rascoff had to say:

“I’ve always looked 10 years my senior and tried to find somebody at my company to think about if I want that person’s life, their whole life.

Usually, younger people earlier in their career look at a senior person and they look at their compensation, and I’m advising not to do that. If you’re an associate in the marketing department, look at the VP of marketing and say, ‘Do I want her or his work-life balance, respect in the community, intellectual stimulation of their job, title’ — sure, compensation, yes, but sort of the whole package.

That’s the path you’re on. You could wake up in the blink of an eye and end up in that world — if you don’t like that trajectory, then find some other path.

The other advice I’d give is something that [Facebook COO] Sheryl Sandberg has been very articulate and eloquent about, which is this whole ‘Your career as a jungle gym not a career ladder.’ It’s something that I found in my career. So what does that really mean? It means that you’re on a particular path and then willing to go off to the side. So in my case, for example, I was running supplier relations — relations with the hotel industry — and then I moved over to a marketing role where I really had no experience or background, and then I moved over to a finance role where yet again I had no direct experience. And so it was kind of like one step to the side to take two steps forward, one step back to take three steps forward, and charting this very kind of circuitous route, which is unique to this generation.

Our parents and our grandparents had a much simpler career path — just sort of do the time and you’ll get promoted eventually. That’s not the way it works now. So you have to build your own career path and be willing to take some steps to the side in order to take steps up.”

You can listen to the full conversation at Business Insider.

Editor’s note: This story was updated to reflect Rascoff’s role at Zillow Group. 

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