Women Upstarts Who Took On Silicon Valley

For Discussion

Motivational Speech (4:55)

Venture capitalist Sonja Hoel Perkins has developed many sayings to describe how she works. One is: “We win, not whine.” Another: “Obstacles are my allies.”

1. What do you think the sayings convey about Sonja as a professional? How about as a woman? Are they different?
2. What saying(s) would you use to describe how you operate professionally?

The Power Duo (5:52)

Sonja talks about recruiting Abe Kleinfeld for a CEO position to help a struggling company. The two developed a strong relationship and continue to work together today.

1. What key characteristics have helped the duo succeed?
2. Do you think this is a “typical” funder/executive relationship? Why or why not?

(Un)Representative? (10:43)

Author Julian Guthrie wanted to share the untold stories of women in the male-dominated and little-understood venture capital industry. She selected four different women to feature in her book.

1. What criteria did she use to select them? Do you think this was an effective way to tell the story? What does Julian miss by focusing on these four?
2. What common themes emerged for the women that helped them succeed in Silicon Valley?

The Money Behind the Men (13:03)

Laurie Yoler talks about the early days of Tesla and Julian Guthrie briefly describes Magdalena Yesil’s role as the first investor in Salesforce.

1. What names do you typically associate with Tesla and Salesforce? What roles do those people hold?
2. Are you surprised by Laurie and Magdalena’s stories? Why or why not?

Tips, Tricks, and Tantrums (17:24)

Sonja Hoel Perkins describes her professional “tricks” for getting along with male CEOs, her role as a VC, and her venture investment strategy. Abe offers his perspective on working with her.

1. What aspects of Sonja’s behavior and strategies would you characterize as “female”? Is there another way to describe them?
2. What are the strengths and weaknesses of her approach in each of these areas?

The First Woman (28:47)

Abe Kleinfeld offers his theories about why there aren’t more women in the tech world.

1. What reasons does Abe give for why there aren’t more women professionals in Silicon Valley? Do you agree? Why or why not?
2. What do you think of Abe’s story about hiring a woman? How else might Abe have solved the problem? Is this an effective strategy for other companies to model?

On the Board (38:16)

Sonja Hoel Perkins and Abe Kleinfeld both have ideas about how to handle company board meetings but from different perspectives: Abe as a man and a CEO; Sonja as a woman and an investor.

1. If Sonja were a man, would her strategy to ask the CEO how s/he is feeling after a board meeting be effective? Would your answer be different if the CEO is a man or a woman?
2. If Abe were a woman CEO, would his strategy to openly share bad news with the board be effective? Why or why not?

Trailblazers and Trojan Horses (42:52)

Julian Guthrie discusses the different ways men and women succeed.

1. How does Julian describe the way that women succeed in a male-dominated industry? Can you relate to these strategies?
2. Are the strategies dependent on age or stage of career? How might they differ for young professionals or someone who has been in a field for a number of years?

Time for Regret (51:21)

Sonja Hoel Perkins says that her biggest mistake was to worry too much about consensus. She and Julian talk about barriers to women in tech and other industries and the need for diversity.

1. Sonja’s regret seems to reflect a dissatisfaction with a trait or role perceived as female. Yet, how does she also explain how it can be a positive?
2. How do you feel about the state of women professionals? What problems or solutions that Sonja and Julian discuss stand out? What do you think the future brings?