Guest: Spencer Rascoff, co-founder and former CEO of Zillow + co-founder and general partner at 75 & Sunny

When terrorists attacked the US on 9/11, Hotwire co-founder Spencer Rascoff and his colleagues had to put their own trauma aside and “spring into action” — the travel site had sold tens of millions of dollars’ worth of non-refundable flights and hotel rooms and customers who wouldn’t be traveling wanted their money back. Now a visiting professor at Harvard Business School, Spencer teaches this case to his students because this dilemma was not unique to 2001: “What the hell do you do when you’re running a company ... and all of a sudden, a pandemic happens? Or SVB shuts down?”

In this episode, Spencer and Joubin discuss Zestimates, context switching, Tom Brady, reinvention, Shaq, the live music business, beating pain, personal connection to tragedies, the structure of rounds, Juul, the qualities of success, Stewart Butterfield, Travis Kalanick, second homes, two-way doors, overstating risk, “Dad, I Have a Question,” management by walking around, and Carl Eschenbach.

In this episode, we cover:

Spencer’s post-Zillow life (00:57)
From player to coach (03:47)
“The Forrest Gump of technology” (08:21)
Joseph Rascoff and the Rolling Stones (10:56)
Teaching grit to kids (14:43)
Spencer’s brother (18:55)
Channeling pain into achievement (21:35)
Co-founding Hotwire (24:37)
The impact of 9/11 (27:51)
Re-capitalization and selling to Expedia (35:17)
“Let’s build a real estate website” (38:05)
Office Hours and founder-product fit (45:12)
How Pacaso works (53:22)
Career mirrors and leaving big companies (57:01)
Staying organized (01:04:20)
Dinner with the family (01:07:43)
What “grit” means to him (01:09:14)

Links:

#165 Former CEO and Co-Founder of Zillow, Spencer Rascoff: Real Estate Voyeurism

Grit