Key Takeaways
Just before Bobbi Brown signed along the dotted line to sell her namesake business to Estée Lauder in 1995, four years after the brand’s inception, for a reported $74.5 million, her husband, Steven Plofker, checked in with her about the aggressive 25-year non-compete. She told him not to worry. “I’m not going to want to work when I’m 60!”
So much for that.
As soon as the legendary makeup artist’s non-compete ended in 2020, she launched her cosmetic brand Jones Road. In September 2025, Brown published her memoir Still Bobbi, an intimate window into the iconic makeup artist’s life.
In her memoir, Brown shares how her family—from her Aunt Alice to her hardworking grandfather “Pappa Sam”—inspired her to become the powerhouse she is today. She takes readers through her Chicago upbringing, the excitement and struggles of starting a career in New York City, her tough decision to sell her business to a conglomerate, and the fun of starting something new with Jones Road.
Brown recently sat down with BeautyMatter Senior Editor Janna Mandell (both Brown and Mandell live in Montclair, NJ) to talk struggles, triumphs, leveraging chutzpah, and sage advice for new founders.
Janna Mandell: I absolutely loved your book. And if I were to pull advice from it, I would say it's all about your chutzpah and trusting your gut, right? There were a lot of times in your career when people wanted you to ignore your gut and go with the flow. Like in the nineties, when you tried to do natural makeup for shoots and people tried to talk you out of it, telling you to bring the drama. When you sold your business [to Estée Lauder], you had to tune out the noise and listen to your gut.
As you know, BeautyMatter is a business-to-business publication, and our readers include founders who may be struggling with their own brand narratives because they’re constantly surrounded by noise. What advice can you give them? How did you know to trust your intuition throughout your career?
Bobbi Brown: You know, honestly, noise gives me a headache. I would sit in meetings, and one smart person after another would tell me how things should be done and how they’ve been done in the past, and I'd always be zoning out because I was so bored. And while they're discussing whatever the issues were, I would be like, “Oh no, here's the solution…” I am very solution-oriented and practical.
When I was in a meeting, and someone told me to discontinue all the colors for dark skin because they're “low sellers,” it was clear to me that we needed to get more women of color as customers. The solution wasn’t to discontinue the colors but find more dollars to market to women of color. Things like that just make sense to me. And, it took me a while to be confident enough to say what was in my head.
JM: Ohhhhh… but you did.
BB: Oh, but I did, but I did with respect. I think a lot of people, particularly women, think that you have to be a son of a bitch and come off really strong, and it can be polarizing. So I'd rather kiss the enemy than fight the enemy. You just have to be smart. I’m also stubborn, but I'm really open. Like, if someone says, “Hey, have you ever thought of doing this?’ And I would say, “I don't think that’s right, but what if we did this?” You need brain clarity, chutzpah, and drive, but you also need common sense.
JM: Also, when it comes to being acquired or taking funding, I see a lot of new founders make the mistake of just jumping in headfirst. They hear they got into Sephora, and they don’t stop to think what it's going to cost to be on those gondolas and endcaps, what it’s going to cost for training and sampling. So, can you talk a little bit about how, as a founder, you can differentiate between the daydream and reality?
BB: Well, I'm someone who always prefers reality. Just give it to me straight. Even now, when someone comes to my office and says, “Here's the new formula. Let me show it to you,” I immediately start asking questions. “Guys, when is it due? How much time do we have?” I want all the facts first. As a founder, quote, unquote, businesswoman, though I never went to business school, I want you to tell me all the facts. Tell me if we have a week to make a decision or six months. And so it's the same thing when a new founder gets Sephora or Ulta. It’s fantastic, but what does it mean? What costs go with that, and what are the timelines? Do you have the right team? You [founders] have to know all those things.
And that's why businesses sometimes fail—because of the founder's inexperience. It’s exciting getting rounds A, B, and C of funding. But okay, now, what do you do with it? Who on your team has done this before? You have to ask these questions. And you can't just have people who are experienced. You also need a few creative sparks on your team, the ones that are more like Swiss Army knives. You need that combination.
JM: When it comes to Jones Road, what do you think are the biggest differentiators, let's say, from pre-acquisition Bobbi Brown to the first few years of Jones Road?
BB: So much in makeup has changed, particularly the amount of makeup [women wear]. Back then, the natural look still required a ton of makeup, and now I just don't think people need it. People look better with less and with a little bit more transparent coverage than full coverage.
JM: Okay, but tell us what you really think about the contouring look, and don’t hold back.
BB: I say it all the time. First of all, contour is really hard for the layman to do without looking like it's Ash Wednesday. Contouring sends a message that something's wrong with people's faces, and I don't believe there is. Everyone has something to really focus on, whether it's your eyes, lips, skin, or cheeks. So I always focused on a pop of color and a little bit of shine on my cheeks. And to this day, I think everyone has their own thing.
JM: Love it. Now, I hate to sound like a college interview here, but it's pertinent. If you could give your best piece of advice for a founder at a pivotal point where they're considering the potential of private equity or a VC investor, what would it be?
BB: Well, I'm going to also give advice to the person getting out of business school who wants to be a founder. I would say, get a job, right? Use what you know, use your education. You just got this great degree, so go work for a company for a year, learn everything you can before you start your own. And then you could start it while you're working. That's my number one.
But for founders who have those decisions to make [to take funding], it is exciting, but it’s important to know it’s a lot like dating. They're all going to tell you something different, and a lot of it is bullshit. Once you rush into a marriage, it’s like suddenly you're doing the laundry, and you’re miserable, and then they start looking for something “better.” You know, it all sounds good, but you have to push back a bit and trust your gut. Look at the financial aspects, but also ask the important questions. Is this someone whom I can go to and say, “I'm overwhelmed, I don't know what I'm doing. You need to teach me.”?There's nothing wrong with saying I don't know; that's how you learn. Part of it is being realistic, knowing the facts, and the other is trusting your gut. And you need to have the right people around you. That's the hard thing: finding the right people to help you make decisions.
JM: I feel like that's one thing that founders sometimes have a problem with. Stepping down from that CEO position and recognizing, “Hey, I'm going to get someone who has run a business before.”
BB: I think that's the reality of it. I think about all of my friends who have sold their companies to either strategics or VCs, and it just doesn't always work out. The majority does not work out right? But then, the positive is there's a payout. And some people end up buying their businesses back and do it all again, instead of starting something new. You know me, I like starting something new. It was fun starting from scratch, because I didn't have to focus on fixing a tired brand. And that's what's been fun. It’s been five years, and now we're looking to make some internal changes. We could use a few people of a certain age and experience in key positions. And you know what that looks like, when it's at the point where you're scaling, and you need the right people around you. And good luck finding the right fit. But that's part of the battle, and not everything works, right?
JM: That's part of the dating.
BB: Exactly.
JM: Bobbi, I know I’ve gone over the allotted time, so thank you for talking to me!
BB: If I see you at Whole Foods or one of those places, make sure you come over and say hi.
JM: Will do. Thank you!