#165 Former CEO & Co-Founder of Zillow, Spencer Rascoff: Real Estate Voyeurism
Nov 20, 2023
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Spencer Rascoff, former CEO of Zillow, discusses his post-Zillow life, teaching grit to kids, the impact of 9/11 on his business, creating a discount travel company, and the importance of having a career mirror.
Planning for the future trajectory of one's career is essential, considering aspects like job satisfaction, compensation, and relationships.
Transitioning from a CEO to an investor and mentor can offer a fulfilling chapter by supporting and guiding other founders.
Personal growth and determination can arise from experiencing loss and going through challenging situations.
Deep dives
Importance of Being Intentional About Future Goals
It is crucial to carefully consider and plan for the future trajectory of one's career, including aspects such as job satisfaction, compensation, title, lifestyle, and relationships.
Transition from CEO to Investor and Coach
Following a successful career as a CEO, the transition to becoming an investor and mentor can provide a new and fulfilling chapter, offering opportunities to support and guide other founders in their own entrepreneurial journeys.
Lessons Learned Through Adversity and Grief
Experiencing the loss of a loved one and going through challenging situations, such as the 9/11 tragedy, can serve as a catalyst for personal growth, determination, and achievement.
Founding and Scaling Zillow
The founding of Zillow involved identifying and addressing personal pain points, such as the need for accessible and accurate real estate information. The company's growth was driven by a focus on traffic acquisition, a unique product offering (e.g., the Zestimate), and the ability to attract and retain a talented team.
Founder Product Fit and Passion for the Problem
One key insight from the podcast is the importance of founder product fit and having a passion for the problem you are solving. The guest shares examples of successful founders who were deeply connected to the problems they were addressing. This connection fueled their obsession and drive to create innovative solutions. The guest also suggests that founder product fit can be developed over time, either by diving into a problem and realizing its potential or by recognizing how a certain mission aligns with personal values. Ultimately, having a deep passion for the problem being solved plays a crucial role in a founder's ability to overcome challenges and build successful ventures.
Context Switching and Career Reflection
The podcast episode delves into the challenges of context switching and the mental taxation it brings. The guest shares how having multiple companies and projects requires constant shifting of focus and decision-making across different areas. This can be exhaustive, and the guest compares it to running into different rooms with completely different situations. However, the guest emphasizes the importance of being intentional about career decisions and evaluating the long-term consequences. The guest encourages individuals to consider their future aspirations and evaluate whether they want to emulate the senior positions in their desired career path to make informed choices and avoid waking up in a role they may not want.
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.
