Chatting with Randi Zuckerberg about female entrepreneurship and her new show “Quit Your Day Job”

Randi Zuckerberg is one busy woman. A Harvard-grad, powerhouse in the business world, she is well-known for helping pave the way for female professionals — specifically in the areas of entrepreneurship and tech. Some of her notable work includes investing in (and advising) multiple women-led startup companies, founding and serving as CEO of production company Zuckerberg Media, writing three books, hosting a weekly business-focused radio show on SiriusXM. Oh, she also played Regina in Broadway’s Rock of Ages in 2014, and is currently a Tony Awards voter. If that’s not enough, she’s a wife and a mother to two boys.

Randi is also one of four investors/panelists on the upcoming show Quit Your Day Job, which premieres on Oxygen tonight. Quit Your Day Job focuses not only on helping fund the business dreams of young entrepreneurs across the country (many of them women), but also mentoring them throughout the process.

We were lucky enough to chat with Randi about her new show, as well as some other projects she has in the works.

HelloGiggles (HG): Tell us a bit about your new series Quit Your Day Job? What is the message and how do you think it stands apart from similar shows?

Randi Zuckerberg (RZ): Right now, entrepreneurship is really having a great moment in pop culture. Entrepreneurs are being seen as “rock stars,” and it’s really thrilling to see that echoed on TV. But what’s really been missing for me is a lot of the shows are still reinforcing the same stereotype of what an entrepreneur looks like. So the fact that [the show is on] Oxygen — a multicultural, young women’s television network — to me, that’s where the game starts changing.

When you show women of all ethnicities, women who come from all different financial and economic backgrounds, that they can be entrepreneurs and that they can get investment, and you then show them that the investors also look different from what they [likely] thought — three out of the four investors on our panel are women — that’s when we really start changing the conservation about what entrepreneurs and investors look like in America. That’s why I’m so excited about this show. I think it really stands apart from the other [similar] shows you might see on TV.

HG: It seems you guys are really there throughout the entire process of development with these entrepreneurs, it’s very hands on. It really adds a personal level that I haven’t seen in similar shows before.

RZ: Absolutely! And what’s so important to starting a company is pouring your blood, sweat, and soul into it, so it’s really hard to sum up an entrepreneur from a 30-second pitch. That’s why I think it’s so important on our show that, first, we took the time to get to know each of the entrepreneurs — we met their families, we saw where they work. We spent a lot of time with them as we evaluated them.

I think it’s also really important that the way we invest in the company is that we’re either all in as an investment panel, or all out — it wasn’t like we were jockeying with each other for better deals, and humiliating or undercutting the entrepreneur. We wanted them to know we all believe in them.

HG: You said in a video on the show’s website that it’s so important for an entrepreneur to sell themselves just as much as, if not more than, the product they’re pitching. What types of business pitches really get your attention?

RZ: It really varies. I’m open to all industries; I don’t want to be closed-minded, like some of the other investors I see who only invest in things they know. But one thing an entrepreneur can do, if they want to come in and wow me, is to show me data. Don’t just come into the room and say, you know, “I really want this, and I’m gonna work really hard.” That’s nice and it makes me want to give you some stickers, but it doesn’t make me want to write you a really big check. [laughs] I want to see data.

I also want to get a taste for who you are as an entrepreneur. Even if you come in with a product I don’t love, if you make [an impression as a good entrepreneur], I’m going to write a check because I’m thinking, “This person is so smart that they’re going to figure out how to change their business to make it work.” On the flip side, you could have the best product in the world, but if you seem like you’re going to be really difficult to work with, I won’t invest. Because when I invest, I want us to be in business together for a long time and have a good relationship. For me it’s more important that the entrepreneur be someone I want to work with than the product being immediately sellable.

HG: What are the most common challenges you see women specifically facing in the world of entrepreneurship, and how would you advise them to handle these challenges? 

RZ: When men come into a room to pitch, they immediately start off by telling me how awesome they are. They tell me about their education, their qualifications, their accomplishments — they have no problem telling me how great they are. But I’ve never met a woman who’s walked into a room and told me [off the bat] anything she accomplished, or how great she is. Women don’t toot their own horns, and I think they suffer for it. I’m going to be blown away by the person who’s giving me all this data, so women don’t do themselves any favors by undercutting or not promoting themselves.


The other common thing I see, is that when men pick cofounders for companies, they tend to pick people who have skill sets that they’re lacking, whereas [I’ve noticed] women tend to pick someone that they’d want to hang out with, and can be friendly with. Because of this, so many times, they tend to duplicate their own skill set instead of gaining a complementary one. I think women need to [be OK with being] harder about choosing whom they go into business with.

HG: What advice would you give a woman who is unhappy in her day job and has a brilliant idea for a startup? What would you advise her first step be?

RZ: I think the first step is to start quietly tapping the market for [your idea]. Maybe there’s an opportunity to open an Etsy shop, or to do a small, private funding campaign. That way, you can see if this is something people are interested in, like if they’d preorder it. Then you can ask yourself, “Is there actually something here that I can quit my day job for?” The market will tell you what you need to hear. If there’s not demand for it, then that’s a great opportunity while you’re still employed in a stable situation to think about, “Okay, how do I change this? Do I need to come up with a new idea entirely?” Luckily, we live in a world where we can get lots of great market research quickly and cheaply.

HG: What inspired you, personally, to dive deep into the world of technology and social media? [Randi’s brother Mark is a name we all know from Facebook, so there is something in the blood.]

RZ: I love studying new trends in how people are communicating. And for me, what was so interesting about social media is that women are making up the vast majority of consumers over all social-media sites — even casual games on the phone, like Candy Crush — it’s so overwhelmingly women.

Yet at the same time, I would see very few women in leadership positions at these companies even though the majority of their customers were women! That’s something I felt very passionately about — that I really wanted to be a part of. Now, I spend a lot of time [in that sphere] — I lecture at colleges, to females who want to go into leadership and engineering. I spend a lot of time speaking with women business owners all over the world, because how can you truly run global companies that are reaching a female majority but have no women in leadership positions at those companies?

HG: We LOVE Dot, your children’s book about a tech-savvy little girl, and are so excited about the upcoming animated television series. Are you planning on writing anymore children’s books in the future – or maybe one aimed toward young adults?

RZ: Thank you! And yes, even though I have two sons, Dot is like my daughter. What I love about Dot is I’ve been in so many rooms where people ask, “Why aren’t there more women in tech? Why aren’t girls going into engineering?” I think it starts really early in pop culture — with young girls needing to see techy, entrepreneurial, savvy girls on TV, and in books. That’s why I’m so excited about [the TV show] Dot. We’re feverishly writing 52 episodes, and it’s airing this September on NBC’s Sprout. It’s exciting for young girls to see a little girl in a cute dress who’s, you know, flying drones and building things!


Hopefully there will be more children-focused things in my future, but between Quit Your Day Job and Dot, there’s definitely a lot on my plate right now. But I’m so excited to be working on both of these projects within the NBC family because I think they both tackle the same [idea] of inspiring more women to get into business, but in different ways. Quit Your Day Job is trying to inspire that young millennial woman to become an entrepreneur, while Dot is trying to reach them when they’re 5 or 6 years old.

HG: So you’re an entrepreneur, a CEO, a radio-show host, an editor-in-chief, a tech mogul, an actress, an author, and a wife and mother. How do you find time to do it all, and what advice would you give to women who want to pursue a similar lifestyle?

RZ: It’s funny, I feel like now that I look back on everything it’s a little exhausting. But luckily, it’s kind of like when you’re a first-time marathon runner — you don’t really know what lies ahead, you just have to push through it all. I think for me, I’m just so lucky to be surrounded by the best of the best people helping me and supporting me in all my projects, like NBC and [Jim Henson Productions] to do Dot. There’s no way I’d be able to do all these projects without an incredible support network.

But I also love to have my hands in everything and kind of control everything! So trusting the people around me is definitely something I’ve really had to learn how to do to take on all these projects.

Quit Your Day Job premieres on Oxygen Wednesday, March 30, at 10 p.m. ET/9 p.m. CT.

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