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Bobbi Brown Talks Career Development, Parenting and Taking Chances Beauty entrepreneur Bobbi Brown headlined Yelp's second annual Women in Business Summit, joined by Yelp Small Business Expert Emily Washcovick. We dive deeper into their conversation that focused on her career journey and spreading entrepreneurial wisdom with attendees.

By Emily Washcovick

Opinions expressed by Entrepreneur contributors are their own.

Bobbi Brown

Bobbi Brown built her makeup empire—for the first time—in the nineties, at a time when shades often had to be heavily mixed to match skin tones and bigger looks were favored over subtle. Her namesake brand, Bobbi Brown Cosmetics, was acquired by Estée Lauder in 1995, but Bobbi stayed closely involved as chief creative officer until 2016.

After signing a 25-year non-compete contract, she passed the time by pursuing a series of entrepreneurial undertakings, from becoming a regular on the Today Show to launching a boutique hotel in her hometown of Montclair, New Jersey.

In 2020, on the day her non-compete expired, she launched Jones Road Beauty, a minimalist makeup brand focused on clean ingredients. The brand is the culmination of her decades of entrepreneurship and beauty wisdom and a physical representation of her personal values. "It's about being comfortable in your skin and looking better. To me, that's what makeup is," Bobbi said. "Makeup is not to be fabulous, [to be] someone else and change you. It's being yourself."

In the early entrepreneurial days, Bobbi was inspired by a lack of shade availability in the industry and went out on a limb, jumping right into meeting with chemists to transition her vision into physical products.

"I could have said, 'Okay, here's an opportunity. Let me go home and write a business plan. Let me try to get financing. Let me…' I did none of those things," Bobbi said. "I didn't know what a business plan was. I didn't know what marketing was. I dove in and just made a lipstick. I saw an opportunity, I dove in, and I did it. And that's probably the difference of how a lot of people look at building their own business today."

Launching Bobbi Brown Cosmetics

The brand started off selling directly to consumers using a mail order system, but after running into the right people, Bobbi was able to scale up more quickly than expected. The first big growth step happened at lunch with a friend who happened to be a writer for Glamour magazine. "They said, 'Can I write about [your brand] in Glamour magazine?' and I'm like, 'Why would you want to?'" Bobbi said. The impromptu meet-up turned into a feature, which led to an immediate influx in calls and attention for the business.

You never know who might be interested in your work—voluntarily sharing what you've been up to allows external actors (like media, investors, or customers) the opportunity to support you. Bobbi later attended a party in Manhattan, where she met a Bergdorf Goodman Cosmetics employee. "I told her about this line of lipstick and, you know, it was not as easy as snapping my fingers, but that's how I got into Bergdorf Goodman," Bobbi said. While these interactions were not initially strategic, Bobbi's willingness to say "yes" and consistently put herself—and, thus, her brand—out there majorly paid off.

But not all of Bobbi's entrepreneurial journey fell into place so simply. Following your dreams is the ultimate goal, but it's not quite as easy as just quitting your current job to pursue your passion. It's important to evaluate your financial situation and have a realistic plan that doesn't ignore the realities, and necessities, of life.

"You have to buy milk. You have to pay the rent," Bobbi says, "A lot of people are pretty much stuck in these high paid corporate jobs because of finances. So then, what do you do? Do what you love on the side—see if there's a way something could work." If your side hustle suddenly becomes an economic possibility, Bobbi said, then you know when you can shift to putting more of your time and energy into it. Some aspiring entrepreneurs end up quitting their day job to pick up temporary evening jobs, that way they can devote more time to their passion without risking their financial wellness.

There will always be naysayers, so being able to look inward and motivate yourself amid negativity goes a long way when you're working as an entrepreneur. "There's always someone that says, 'The world doesn't need another makeup line,' or 'You're too old. No one's going to be interested,'" Bobbi said. "I heard everything. You listen, and you move on. It's just noise, and it's not your noise—it's their noise."

Juggling parenting and business

The work-life balance conversation is always trending because it's one of the most difficult parts of career and personal development to achieve, especially for mothers. With entrepreneurship being such a demanding path, Bobbi faced her fair share of challenges as she raised her three children an hour outside Manhattan.

She didn't do it alone, and shared that choosing a life partner is one of the most important decisions you make, both for your personal and professional life. "From the beginning, it was really tough. If I didn't have my husband, who was an incredibly supportive husband, when the kids got sick, when they had to do something, it would've been impossible to do," Bobbi said.

It goes to say, there's no shame in asking for help. In fact, if she could go back in time, she would have asked for more. Sometimes parents need to be selfish in taking what they need and being a little bit easier on themselves—getting everything done is far too much for any singular person. "Susan Sarandon, when I was doing her makeup, said to me, 'Go hire someone for the weekends, not to play with your kids, but to be at home and clean your house and get your house in order,' and I didn't listen to that," Bobbi said. "And that's one of the things I regret. I sent my kids with my husband and I cleaned and I grocery shopped, and, by the way, I didn't get any awards! Try to figure out how you could spend more time with your kids."

As she grew older, Bobbi was able to start "hacking" parenthood—figuring out the tricks and shortcuts to complete what she needed to do and still feel fulfilled and successful as a mother. "I made sure I was staffed up at home, whatever it meant," Bobbi said. "I always figured out how to make things work. I think it's being an entrepreneur, not just of business, but of my life."

It's a constant juggle—after all, there are a finite number of hours in a day. Entrepreneurship requires you to prioritize, take risks, and learn as you go. You have to know what is most important to you because it's easy to get lost in the shuffle of business and being busy. "Your time and energy is precious—know what's worth it and quit the things that aren't," Bobbi said.

"I had an eyeglass line that was successful for a while, and then it wasn't. I [said to myself], 'Okay, this isn't working right now. I'm not going to do it.' Luckily, I had other things to keep myself occupied, but I don't look at those things as a failure. I look at them as an opportunity to learn what is not working and what I can't do."

Emily Washcovick

Small Business Expert at Yelp

As Yelp’s Small Business Expert, Emily is meticulously focused on helping local business owners succeed and grow. Her expertise lies in customer engagement, reputation management, and all things digital marketing. Through speaking engagements and thought leadership, Emily shares industry insights that entrepreneurs in any business category can leverage for the growth and well-being of their businesses. She is also the host of Behind the Review, a podcast from Yelp and Entrepreneur Media, where each episode features conversations with a business owner and a reviewer about the story and lessons behind their interactions.

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