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What Women Can Learn About Business From Playing High Stakes Poker

2016 Wired Business Conference2016 Wired Business Conference
CEO of Crisis Text Line Nancy LublinBrian Ach Getty Images for Wired

Forget playing politics. Nancy Lublin says she learned many of her most valued business lessons playing poker.

Speaking on a panel hosted by Sotheby’s on Tuesday night, the founder of Dress for Success and Crisis Text Line and former CEO of Do Something recalled spending the evenings of her mid-20s playing the game at “underground clubs” in New York City. Putting her money on the line—and staring down the men across the table—was an invaluable lesson, she says.

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“There’s something about learning to value your own hand, learning how to play your position at the table,” Lublin told moderator Jennifer Reingold, Fortune editor-at-large. Even more critical for women: “Learn how to fold, say goodbye to that hand, and move on. We hold on to stuff.”

Serial entrepreneur and angel investor Caterina Fake echoed the importance of letting go of professional mistakes or disappointments. She has no problem brushing off rejection when meeting with venture capitalists, she says, “If you diss me, I fold and I’m out—I’m on to the next one.” That strategy seems to have worked out for her: While fundraising for Etsy, where she was chairman of the board, she says male VCs often characterized the startup as “a bunch of chicks sitting around knitting.” The company went public in 2015 and currently has a market cap of more than $1.5 billion.


Fake, who is perhaps best-known as the co-founder of Flickr, also encouraged the audience to make the best of those moments—be it in a VC meeting, an interview, or anywhere else—when you’re the only woman or person of color in the room. “I feel powerful in my difference,” she said.

Laurie Segall, senior technology correspondent for CNN, says that she often finds herself in that situation covering Silicon Valley. She recalled one instance where a VC mistook her as a founder rather than a journalist—and assumed that she must have created a wedding app, or something equally “girlie.”

One foolproof way to make those rooms more diverse, noted fellow panelist Candice Anderson, executive director of Cool Culture, is to start your own thing. Anderson’s organization, which provides families with young children with access to the arts, is entirely run and staffed by women—the majority of whom are women of color.

Investing in women’s companies is another way to change the game, said Lublin. “Some of the wealthiest women in Silicon Valley—I won’t mention any names—their capital is not being released,” said the founder. “The women who have made a lot of money need to start spending it.”