Randi Zuckerberg: Silicon Valley Girl

Sibling relationships have been fraught and competitive since the dawn of time.

Cain and Abel, the Bible’s very first siblings, set the gold standard for rivalry when Cain slew Abel in a field. Things barely improved from there: Jacob stole his brother Esau’s birthright; Joseph’s brothers left him for dead in a pit; Leah wedded and bedded her sister’s beloved — hardly the portrait of Hebraic family harmony.

Randi Zuckerberg has had the opposite experience. After graduating from Harvard in 2003, to a $32,000-a-year job as a Fox News show production assistant, her brother Mark, founder of Facebook, later offered her a plum job as the company’s head of marketing, practically anointing her a Silicon Valley star.

Talk about a lucky break: Today, she is an Internet entrepreneur, the founder of Zuckerberg Media, the author of the book “Dot Complicated” and a related lifestyle Web site, as well as a wife, mother and multimillionaire.

She never saw it coming. Back in 2005, according to Zuckerberg family myth, younger brother Mark was concerned his sister was heading toward a “dead end” and decided to fly her from New York to Silicon Valley to visit Facebook’s offices. By the end of the trip, he made her an offer: Sloppily scrawled on a single sheet of paper, he wrote two numbers, a salary and a number of stock options. With stunning bravado, his sister — the eldest of four — crossed out the stock options and doubled her salary. Mark kindly insisted on his original offer.

The rest is family, Facebook and, arguably, national history.

“I really did experience the American Dream — in the cheesiest, cheesiest way,” Zuckerberg told me last week when I met her at the Beverly Hills Hotel. The outspoken and animated 32-year-old was visiting Los Angeles to speak to a Jewish Federation women’s luncheon for big donors — which was appropriate, since she recently became one.

A decade ago, she was just “a poor, entry-level” working girl barely in touch with her roots who jumped at the chance to go on a Birthright trip with her then-boyfriend (now, husband) because it was free. “We didn’t have that much money, so we thought, ‘Let’s go to Israel! For free! How awesome.’ ” She was equally loosey-goosey about her brother’s life-changing job offer. “I couldn’t envision that life existed outside of Manhattan,” she told the crowd of 500 women. “I was not about to move to a suburb of California to work on my brother’s stupid little project.”

Confident in the spotlight and a natural on stage, Zuckerberg worked wonders on this crowd, most of whom were agape over her sprightly sense of humor (“I would like to point out that I actually graduated from Harvard, unlike another member of my immediate family,” she quipped), even if it makes her sound a little jejune. And she won over even more fans with her singing voice, concluding her appearance with a rendition of Debbie Friedman’s “L’Chi Lach.”

Zuckerberg’s entertaining exuberance has sometimes done her a disservice. Early on at Facebook, she ran into trouble when a few videos showcasing her inner actress (in one, she wore a pink feather boa over a bathing suit and lip-synched “Chapel of Love”) went viral on the Internet and embarrassed the company. The press piled on, encouraging an image of Zuckerberg as a brassy, out-of-touch sorority girl.

Since then, she has become much more conscientious about her public image — and her politics.

Several years ago, when she attended the World Economic Forum in Davos, Switzerland, as a correspondent for Facebook, Israeli President Shimon Peres invited her to sing at Israel’s official Shabbat dinner. After performing “Yerushalayim Shel Zahav” before a room full of international dignitaries — “everyone from your dreams,” she recalled giddily, including Israeli Prime Minister Benjamin Netanyahu and Nobel Prize winner Elie Wiesel — Zuckerberg realized that “I had just taken a very public stand for Israel and for the Jewish community.”

A backlash ensued. Some critiques were so withering, Zuckerberg decided to “decline the honor” when Peres invited her to repeat her performance the following year. In a world where you are what you post, and Google can aggregate your hits and misses on a single page, Zuckerberg concluded, “You only get one identity.” 

Yet, just within the last several years, Zuckerberg has undergone two transformations that have altered her public persona: She quit her job at Facebook and gave birth to a son.

“Having a son changed my relationship to Judaism and Israel,” the Reform-raised Zuckerberg said. When she married her husband, who grew up Conservadox in South Africa, they tacitly agreed to practice “his and hers Judaism,” which translated to: “I’ll sneak some shrimp when we go out, and we won’t talk about it.”

“But that doesn’t work with a son,” she admitted. “We needed a shared value system” — and, as they had both happily shared Birthright, Israel seemed like a good place to start.

Last year, Zuckerberg invited 16 Silicon Valley CEOs to accompany her on a high-tech tour of their counterparts in Tel Aviv.

“After that, I became a Super Jew,” she said. She earned vociferous applause when she told the Federation crowd that she had returned to Davos last January and performed again at Israel’s Shabbat dinner. She also let slip she had applied for the Wexner Heritage Program. “I think I find out tomorrow,” she said entirely un-self-consciously. “If anyone wants to put in a call …”

Zuckerberg is also beginning to think strategically about her giving. Until recently, she admits, she was thoughtlessly plunking down money for tables at charity dinners without any sense of purpose. “I realized, ‘Wow! I’m being very charitable across a lot of things, but I have no mission.’ ” She started a donor-advised fund with The Jewish Community Federation of San Francisco and explained that, for now, all her giving is focused on the Jewish community and Israel.

She’s serious about making her own mark — away from Mark.

“I had an incredible time working at Facebook,” she said. “But I definitely felt like I was living inside a really big shadow. And the only way I was going to stand a fighting chance of making my own name in the world was to tear the Band-Aid off.”

She admitted, however, that she misses it. “I think I’m still on a bit of a journey discovering who I am — and that’s the fun of life.”