Dot Mom

Randi Zuckerberg doesn’t pretend to do everything well—at least not all at once, not every single day. Though the mom-of-two’s professional undertakings are seemingly limitless—entrepreneur, author, radio host, investor, TV personality—she’s realistic about the fact that trying (or even pretending) to juggle all of her obligations simultaneously is, ultimately, impossible.

“People always—especially with women—are like: ‘How do you balance it all?’ And then, I don’t know, maybe you’re supposed to come up with some fake answer,” she says as her assistant applies her makeup prior to our photo shoot. “I just think it’s impossible, in a 24-hour-period, to do everything well, and if you put that kind of pressure on yourself you’re just going to burn out.”

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Photos by Michael Jurick Photography. Hair and makeup by Jesus Gonzalez. Styled by Mia Weber. On Randi Zuckerberg: Cynthia Rowley dress; Isharya bracelets; her own Kate Spade New York shoes

Zuckerberg, 34, has referred to her preferred time-management technique as being “well-lopsided”: “I get up every morning and I think: ‘Okay, what are two or three things I’m going to do really well today?’ And some days that’s be a great mom, and I’m going to get a lot of sleep, and take care of myself. And some days it’s like, I’m going to work really, really hard today…and as long as that balances out over time, then that becomes a sustainable life where you get closer to having it all.”

Professionally, Zuckerberg has created a multifaceted career that allows her to pursue her interest in how technology and social media impact our lives. After getting her start in tech working as the director of marketing at Facebook from 2005-2011—yes, her younger brother is that Mark—Zuckerberg left to found her own marketing and production company, Zuckerberg Media, whose clients have included Condé Nast and PayPal. In addition to authoring two books that explore the impact of tech on our social culture—the bestselling dot Complicated, for adults, and Dot., for children—she also founded, an online community dedicated to the topic, and hosts a weekly “Dot Complicated radio show on SiriusXM Business Radio. TV is her next frontier: Dot. has been produced by the Jim Henson Company and will air on NBCU Sprout this coming fall. Later this March, Zuckerberg will star as one of four investors and mentors on Oxygen’s new entrepreneurial docuseries “Quit Your Day Job.”

When we meet for our interview and photo shoot in mid-January, just a few days after Winter Storm Jonas dumped 2+ feet of snow on the city, Zuckerberg is in the midst of her busy season, giving keynotes at the various tech conferences that run through the winter and spring. Despite the currently frenetic pace of her schedule, Zuckerberg is engaged and fully present, offering a cheery picture of the “well-lopsided life.” Large Starbucks coffee in hand, she jumps into the shoot wholeheartedly, gamely trying on dresses, sharing advice with our photographer about managing his daughter’s screen time, and singing and dancing along to the “Hamilton” soundtrack.

No matter where Zuckerberg’s busy professional life takes her, she always tries to make it home for the weekend to spend time with her sons—Asher, 4, and Simi, 1—and husband Brent Tworetzky, who works as the executive vice president of product at the XO Group.

While the family is relatively new to New York City—they moved from Palo Alto, CA, this past summer—Zuckerberg is a Westchester native and spent time living in the city and working in advertising after earning her undergraduate degree at Harvard. And in fact, she says she’s always considered herself a New Yorker. Ultimately, a confluence of factors drew her back to the city: As Asher approached school-age, she and Tworetzky started to seriously consider where they wanted to begin their children’s education. And when Zuckerberg was asked by the producers of Broadway’s “Rock of Ages” to perform in the show in 2014, after speaking at a TEDx Broadway event, she realized that the city offered too many appealing opportunities to turn down.

“I think that was the real decision-maker for us because I thought: ‘Wow, what an amazing city this is that you can be in tech, and business, and singing on Broadway, and [have] all of this culture and all of this art and business right at your fingertips in the same place,’” she says. “You just don’t get that anywhere else in the country.”

The New York that Zuckerberg knows now as a mom is vastly different from the one she left as a recent college grad beginning her career.

“When I left New York, I was 24 years old and I was falling in love and I was living in Midtown… I’m not at the bars until 2am anymore,” she says, laughing. Now, from the vantage point of her family’s home near Central Park, Zuckerberg has been pleasantly surprised as she notices the many family-friendly aspects of the city. In particular, she’s loved sampling the many sophisticated children’s theater options, and makes an effort to catch a show with her sons every couple of weeks.

“I’ve seen so many kids’ shows for 2-6-year-olds that won Drama Desk awards, and really avant garde things for children,” she marvels.

Her children, too, have been adjusting smoothly to city life. Asher is working on memorizing the subway system, and has even taken to the less-than-glamorous aspects of NYC living.

“One day he saw a cockroach, and he told me it was the best day of his life because he had never seen a bug so big before,” Zuckerberg says. “It’s kind of healthy to see the world through the wonderment of a 4-year-old, and I’ve developed, I think, even more of an appreciation of some of the [annoying] things about New York through his eyes.”

Meanwhile, Zuckerberg says Simi “definitely got the memo that he’s a second child! Our entire life I feel like is optimized around Asher, and Simi just goes along with it very cheerfully,” she says.

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Photo by Michael Jurick Photography. On Randi Zuckerberg: Betsey Johnson dress; J.Crew necklace; Isharya bracelets; her own Kate Spade New York shoes.

As she speaks and writes professionally about the role of technology in our lives, Zuckerberg maintains her own carefully constructed set of tech rules at home. “You have to earn [tech] through a mixture of good behavior [and] doing chores,” she says. “And when tech is earned, we try to have it be kind of educational.” Ironically, Zuckerberg grew up in a very low-tech household—her parents “didn’t believe in TV for children,” she says. “I feel in some ways that they did me a favor, but I also feel in other ways there is a giant, kind of two-decade long gap in my knowledge of pop culture.” She advises parents to seek a healthy balance.

“I think it’s different for every family, but I think you don’t want to take all tech away from your children because these are the skills they’re going to need to be successful in life,” she explains. “All of their other friends, their peers, are going to have access to these gadgets, so if your children are not exposed to these devices, and are not learning, they’re behind from day one.” However, she counsels that parents should take care to follow the same tech rules that they set for their children. “They’re learning from a combination of watching their friends and watching you,” she says.

Zuckerberg is particularly conscious of the example that she is setting for her two boys as she forges a career that merges all of her interests. Growing up, both of her parents were doctors, but Zuckerberg’s mother felt social pressure to quit her job at the hospital, and eventually decided to stay home and take care of her four children. “When [my mom] was raising us, she got a lot of flak from other moms for working because that was not really a thing that you did back in the ‘80s as a woman,” she recalls. “And to fast forward 20, 30 years later and see how different the world is now—I go to drop off my son at preschool and all the moms are heading onto the subway to their jobs… I feel really lucky because I know my mom’s career was really important to her, and I feel really sad that society pressured her into giving it up. And I think it’s especially important for young boys to see their moms being productive and contributing.” The representation of women in technology is another issue that Zuckerberg is deeply passionate about, and she treasures her public speaking engagements as opportunities to inspire and connect with women who want to go into the field.

“I love a lot of the public speaking that I’m doing now,” she says. “I feel like it marries my two biggest passions in life, which are inspiring women and young leaders to get into technology, and theater and performance.”

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Photo by Michael Jurick Photography.

Zuckerberg began carving out this professional niche while at Facebook, citing her work on the site’s political coverage as some of her proudest achievements. During the 2008 presidential election, she helped launch the Facebook Politics app in partnership with ABC News, and covered Barack Obama’s inauguration for a Facebook integration with CNN. In 2011, she was nominated for an Emmy for her coverage of the 2010 midterm elections, which blended TV reporting and social media. “I think we really changed the game for politics…I think candidates were not thinking about social media as the way to reach audiences and engage with constituents,” she says. “Fast forward, I mean entire elections are won and lost on social media. So I feel proud to have worked on a team that made such an impact in politics and on the country.”

During Zuckerberg’s six-year tenure at Facebook she became drawn to social media’s capacity to serve as an influential platform of expression for anyone with internet access. “For me, that’s always been my big passion with technology, is giving a voice to people who haven’t had a voice before. Every project I did at Facebook I felt most proud of, whether it was giving a voice to women, giving a voice to people who don’t have freedom of speech in their own country, giving a voice to people who politicians generally overlook because they don’t write huge checks—that is what’s so thrilling to me about technology.”

Zuckerberg will bring her passion for empowerment to television starting March 30 on “Quit Your Day Job.” Alongside three other successful investors, she’ll listen as hopeful millennial entrepreneurs pitch their passion projects, and mentor the promising contestants—assisting in everything from making introductions to helping design a prototype. However, Zuckerberg points out that the show will differ from “Shark Tank” and other entrepreneurship reality shows in that all four cast members must decide together which products they will back.

“If a start-up came to me that was cool, I would never try to undercut my friends to get the deal,” Zuckerberg explains. “I would call up eight of my women friends and I would say: ‘This startup is so cool, we should all invest together…’ [On ‘Quit Your Day Job’], we’re either all in or all out. So there’s no jockeying, one upping each other for deals, we either all agree or we don’t invest. And I think that’s much more in line with how women actually do business.”

As she helps others kick-start their dreams on “Quit Your Day Job,” and inspires women to pursue careers in technology through her speaking engagements, it’s evident that Zuckerberg’s own career has come full circle. Though she’s now the one granting opportunity in the tech and business realms, there are still goals she’d like to pursue in the world of theater. She says she wants to get involved with a theatrical board in the city, or even one day produce a Broadway show.

“I think if you had asked me when I was 4 years old what I wanted to do with my life I would have said: ‘I want to sing on Broadway.’ And if you had kept asking me up until the moment that I actually had to make a realistic choice about my life, I probably would have kept saying that,” she says. “I always loved this world of getting onstage and being someone different, and kind of entertaining people. I don’t know, I’ve always loved to be in the business of joy, I guess.” She continues: “I think that’s part of what drew me to Facebook and what has drawn me to a lot of things about technology.”