Navigating Culture and Change at TaskRabbit

This chapter chronicles the transition from a large corporate environment to the innovative startup culture of TaskRabbit. It emphasizes the challenges of cultural integration, communication strategies, and successful leadership transitions that fostered a collaborative and resilient team dynamic.

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Stacy Brown-Philpot is a unique voice in Silicon Valley. She began her career as a public accountant and worked at Goldman Sachs before landing at Google.

She was the COO and then the CEO of TaskRabbit, which she saw through its sale to Ikea. Today, she’s on a number of corporate boards including HP, Nordstrom, StockX, Noom, and Black Girls CODE. She’s also a founding member of the SoftBank Opportunity Fund, which invests in Black, Latinx, and Native American founders.

Throughout, she’s been a consistent advocate for building cultures where people can bring all aspects of their rich and varied lives to work. The importance of setting out what you want to be and fully committing to it is the wisdom she’s held her entire life: “My grandmother's always telling me, if you don't stand for something, you fall for anything.”

In our conversation, we touched on Google’s rise and its eventual tumble from its “don’t be evil” ethos, what it was like to pioneer the sharing economy at Task Rabbit and the pivots the company went through along the way, and why selling the company to Ikea was dependent on its mission because “they weren't going to buy anything just to buy it. They needed to buy something that they believed in because they're only a part of something that they believe in.”

Stacy’s model of compassionate leadership is inspiring, as is the fun she’s had executing it for the last few decades, even when things were bumpy. She had a lot to say about both, as well as: