The Art of Pivoting: How TaskRabbit Reimagined the Gig Economy | Stacy Brown-Philpot (Google, TaskRabbit, HP, Nordstroms)

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:

• What “the greater good” really means

• Going from 50,000 people at Google to 60 at TaskRabbit

• The value of sharing meals

• The importance of celebrating things that happen outside of work at the office 

• Carrying forward a founder's legacy into a new era for the company

• Fomenting crisis to foster growth

• How constraints breed creativity

• Taking the chaff with the wheat, at work, as a parent, and anywhere else

• The role of the board 

• DEI

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Where to find Stacy Brown-Philpot

• X: https://x.com/sbp04 

• LinkedIn: https://www.linkedin.com/in/stacyphilpot/

Where to find Eric:

• Newsletter: ⁠⁠⁠⁠⁠https://ericries.carrd.co/⁠⁠⁠⁠⁠ 

• Podcast: ⁠⁠⁠⁠⁠https://ericriesshow.com/⁠⁠⁠⁠⁠ 

• X: ⁠⁠⁠⁠⁠https://twitter.com/ericries⁠⁠⁠⁠⁠ 

• LinkedIn: ⁠⁠⁠⁠⁠https://www.linkedin.com/in/eries/⁠⁠⁠⁠⁠ 

• YouTube: ⁠⁠⁠⁠⁠https://www.youtube.com/@theericriesshow⁠⁠⁠⁠⁠ 

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In This Episode We Cover:

(00:44) Meet Stacy Brown-Philpot

(05:11) The heyday of Google’s “don’t be evil” culture 

(08:01) Google’s IPO

(11:20) Stories from Google’s hyper-growth era

(13:44) The shift to backing away from idealism

(15:46) How the 2008 downturn changed Google’s DNA

(24:13) The difference between cultures at Goldman Sachs and Google

(29:43) Mistakes, apologies, and creativity

(31:18) Stacy’s transition from Google to TaskRabbit

(33:52) “the serendipity of what it means to be building something together”

(35:00) Navigating culture change at TaskRabbit

(42:31) Pivots at TaskRabbit

(46:08) Cutting categories and losing revenue for a longer-term goal

(47:35) Inside the TaskRabbit pivot war room

(48:59) Stacy’s stories of taking client and customer calls from her couch

(57:20) The Ikea acquisition and cultural alignment

(1:00:15) Ikea’s foundation ownership model and its “vertically integrated” mission

(1:01:27) Stacy’s reflections on her startup experience

(1:04:05) Stacy’s view of the board’s role in a company

(1:06:07) How she came to be on the board of HP and the companies that followed

(1:07:26) The pandemic at TaskRabbit and on the Nordstrom board 

(1:08:21) George Floyd 

(1:11:20) Stacy’s views on DEI, where we are now, and its cyclical nature

(1:14:45) Lighting round

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Eric may be an investor in the companies discussed.