Welcome back to The Room Podcast. We kick off Season 7 with Spencer Rascoff, co-founder and previous CEO of Zillow. Spencer walks us through how he and the team came up with the idea for Zillow and the unforgettable “Zestimate” feature. Prior to Zillow, Spencer had been the founder of Hotwire, which sold to Expedia for $685 million. Currently, Spencer is an active angel investor in more than 100 companies and is incubating several more through his startup studio and venture capital firm, 75 & Sunny. He serves as executive chair of dot.LA, a news site covering the Los Angeles tech scene and he is co-founder and board chair of Pacaso, the company pioneering a new way to own a second home.

In our conversation today, we explore insights and themes such as the art of a killer feature, like the Zestimate, managing team morale and execution amidst a macroeconomic downturn, and why the future of real estate is fractional.

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5:05 - Where did Spencer grow up and how did that change his view of the world?
6:33 - Did Spencer always want to be a founder?
7:38 - What was the public opinion of the internet when Spencer was at Harvard?
11:23 - What did Spencer learn about being an entrepreneur from his experience at Harvard?
13:23 - What was the aha moment that sparked the launch of Zillow?
15:51 - How did Spencer and the team hone in on the specific product feature for Zillow?
19:04 - Did Big Data play any role in the start of Zillow? What was the data stack at the time?
21:15 - Who was the first external investor to say yes to investing in Zillow?
21:53 - What is the best case board dynamic?
26:04 - How did Spencer balance internal and external stakeholder management through his founding journey?
29:52 - What advice would Spencer give to entrepreneurs navigating “the early stages of our recession?”
31:49 - What is Spencer hoping to accomplish with Pacaso and “fractional ownership” of property?
34:08 - What is the user journey of purchasing a Pacaso home?
35:09 - What is one sector that Spencer believes is undervalued at the moment?
35:33 - Who is a woman that has had a profound impact on Spencer and his career?

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