Spencer Rascoff’s career is a masterclass in navigating crises. After co-founding the travel site Hotwire, the 9/11 tragedy devastated the travel industry. Spencer helped steer the company through this crisis, leading to its $685 million sale to Expedia. He then co-founded Zillow, guiding it through the 2008 housing crash and growing it to a $20 billion market cap. His third venture, Pacaso, a luxury vacation home co-ownership platform, launched just before the pandemic. Despite initial fears about shared spaces, the crisis increased demand for second homes, helping Pacaso achieve unicorn status. In this episode, Spencer shares with Ilana his hard-earned insights on navigating the highs and lows of startup life and turning crises into opportunities.

Spencer Rascoff is a serial entrepreneur, investor, and business executive best known for co-founding Hotwire, Zillow, and Pacaso. As the founder of 75 & Sunny Ventures, he mentors and invests in startups, aiming to democratize access to business opportunities and innovation.

In this episode, Ilana and Spencer will discuss:

(00:00) Introduction 

(02:03) His Early Exposure to Entrepreneurship

(04:13) Building Strong Work Ethic in High School

(06:07) Spencer’s Path from Banking to Startups

(07:21) Founding Hotwire and the Impact of 9/11

(09:47) The Hard Truths of Building Startups

(11:47) What It Takes to Keep Going During a Startup Crisis

(13:58) How Zillow’s ‘Zestimate’ Led to Its Explosive Launch

(17:52) Balancing Speed and Quality in Product Launches

(20:50) Zillow’s Mobile-First Strategy That Won the Market

(25:35) How Zillow Thrived During the 2008 Mortgage Crisis

(28:40) Leading Zillow with Empathy and Teamwork

(32:49) Why Spencer Left Zillow at Its Peak

(33:58) The Fast Rise of Pacaso Amid Pandemic Fears

(37:29) How Pacaso Is Opening Up to Retail Investors

(38:20) Spencer’s Mission to Build Accessible Ventures

(41:53) The Secret to His Success

Spencer Rascoff is a serial entrepreneur, investor, and business executive best known for co-founding Hotwire, Zillow, and Pacaso. He served as CEO of Zillow, leading the company through the 2008 housing crisis and growing it to 4,500 employees and $3 billion in revenue. In 2015, Spencer co-wrote and published his first book, Zillow Talk: Rewriting the Rules of Real Estate, and in 2017, he was named the Most Powerful Person in Residential Real Estate by the Swanepoel Power 200. As the founder of 75 & Sunny Ventures, he mentors and invests in startups, aiming to democratize access to business opportunities and innovation.

Connect with Spencer:

Spencer’s Website: www.heylibby.ai/spencerrascoff 

Spencer’s LinkedIn: linkedin.com/in/spencerrascoff 

Spencer’s Twitter: x.com/spencerrascoff 

Leap Academy:

Ready to make the LEAP in your career? There is a NEW way for professionals to Advance Their Careers & Make 5-6 figures of EXTRA INCOME in Record Time.

Check out our free training today at leapacademy.com/training