Randi Zuckerberg glides into the bar like a cool breeze, publicist and stylist in tow. She's smiling, fresh-faced, and gracious, which is astounding, given the unseasonable heat outside and the epic schedule she cleared to meet me.
After a six-year stint at her brother's company (a little outfit called Facebook), rising from marketing manager to director of consumer marketing, Zuckerberg, 33, is back in the New York City area, near where she grew up. "I said to my husband, we either need to do it, or we just need to admit that we're never moving back to New York and that we're comfortable in the California sun," says Zuckerberg. The pull of the East Coast, it turned out, was stronger than the sun.
For good reason. Silicon Valley had lost its luster for Zuckerberg. In her view, its startup culture is not kind to high-achieving women who also have outside creative pursuits, as she does.
"I found it very difficult, as a woman, to be able to have a side interest in Silicon Valley," says Zuckerberg. "I felt that it was cool if my male colleagues were DJ'ing or hiking or going skiing on weekends. But as a woman, I felt it was almost this kind of 'Well, we've let you in the boys' club to work here, so nothing else need take your focus away.' "
But one suspects the scrutiny she faced from the gossipy Silicon Valley tech press during her tenure at Facebook had more to do with that last name than with her gender. And, when pressed, she admits she played a part in the dynamic. While working her way up the company's executive ranks, she tended to express herself exuberantly and publicly. She posted parody videos on YouTube (under the pseudonym Randi Jayne), got onstage to sing at major industry events at which she was representing the company, played in the Facebook house band, Feedbomb, and generally behaved like an energetic, theatrically inclined twentysomething taking advantage of the brightest of spotlights. "It's important to be authentic to who you are and put yourself out there," says Zuckerberg.
It's apparent the Valley prefers its execs to be Jobsian or Muskian--not Taylor Swiftian. So, like many others who experimented with these shiny new social media tools--back when we could still believe that no one at work would ever see us doing that--Zuckerberg learned a hard lesson about not putting too much of your authentic self out there, especially if you are an authentic Facebook executive.
"Having that last name opened so many doors for me," says Zuckerberg. "But it also forced me to learn a lot of lessons about how the world works. At age 24 or 25, I was really coming into my own at Facebook, but I might have had a buffer of a few more years to learn those lessons at a different company or in a different industry." She quit Facebook in 2011. "I also knew that I was never gonna be 'Randi Zuckerberg--her own thing' as long as I worked there," she says.
Shortly after the birth of her first son, Asher (now 4), when she says she was feeling "like a bit of a superhero, and also, you're a little bit crazy from hormones," she decided to start her own business. She didn't know what, but she knew it would merge her love of the theater, creativity, and technology.
In 2013, she launched Zuckerberg Media, a marketing firm and production company. (Clients include PayPal and Condé Nast.) Since then, she's written two books, Dot Complicated, a guide to managing online life, and Dot, an illustrated children's book. Dot has been optioned by the Jim Henson Company for an animated TV series, of which she is an executive producer. She has a SiriusXM Business Radio show, and she's also been shooting a new reality series on the Oxygen Network called Create Your Day Job.
Oh, and did we mention her lead role in a Broadway musical?
In January 2013, Zuckerberg gave a TEDx Broadway speech at the New World Stages in New York about how the Great White Way could leverage social media to broaden its reach and sales. The producers from the hit musical Rock of Ages saw her talk and decided to bring her in to consult for the show. But when they Googled her, they found an old video of Zuckerberg tearing it up with Feedbomb. Instead of consulting, they invited her to perform a lead part in the show for a limited run.
The day the producers called with their offer, "I thought Ashton Kutcher was going to jump out and be like, 'You've been punk'd!' " says Zuckerberg. "I got the call on Thursday and I moved to New York to start rehearsals the next Monday."
Why the rush? Turns out that Zuckerberg got some other news that same day.
"That was also the day I found out I was pregnant with our second son," she says of Simi, now 1.
After talking it over with her husband, Brent Tworetzky, they agreed she couldn't pass up the opportunity to make her lifelong dream come true. "It was almost like this Pandora's box opened in my soul," she says, "because I had kind of tried to smoosh down [my creativity] for too many years in order to be taken seriously in Silicon Valley. Suddenly I thought, 'Screw that. Life is way too short to shelve what makes you happy just to please a few people who will probably never be pleased by you anyway.'"
Tworetzky took over full-time parenting duties, and Zuckerberg flew east for rehearsals and her 30-show run, which extended from March into April 2014. She managed Zuckerberg Media remotely, but her stint in the city convinced her it was time to relocate permanently. The family moved to New York in July 2015. Tworetzky is now an executive at XO Group, publishers of The Knot.com and other media properties.
In other words, since getting back to New York, Zuckerberg has settled into her role as creative soul, putting her full, authentic self out there, in all media--in fact, as many media as she can find--for all to see. Damn the press. And for the record, being a Zuckerberg didn't win her the Broadway role by itself. She actually has a very pretty singing voice. You can hear it for yourself, thanks to YouTube.
"I'm glad that I made those videos and stuck with my creative interests and put myself out there," says Zuckerberg. "There's no way I would have been able to circle back to doing everything I love with the theater if I hadn't laid that foundation 10 years ago."