Bobbi Brown on How She Developed Her Signature Natural Makeup Style

There are not many entrepreneurs who can say they started one of the most influential beauty brands in America—Bobbi Brown has started two. In 1991, she launched Bobbi Brown Cosmetics, a company which ushered in a new era of natural-looking makeup, defined the look of the ‘90s, and transformed the way women thought about their appearance. Now, 25 years after Bobbi Brown Cosmetics was acquired by Estée Lauder, Brown has launched another transformative beauty brand: Jones Road Beauty, a skincare-based cosmetics company that is redefining how we think about aging and natural beauty in the age of Instagram.

This is one of my favorite conversations I’ve ever had on this show because I’ve known Bobbi since I was young, and she lives in the New Jersey town where I grew up. We spoke frankly about how mothers and daughters talk about beauty, the perils of injections and plastic surgery, and what she learned from starting a second iconic beauty brand, this time in her 60s.

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Tune in every Thursday, and join us as we continue to explore the minds that shape our world. You can listen to the full episode above, and below are a handful of excerpts from our conversation that have been condensed and edited for clarity.

On developing her signature, natural-beauty style as a makeup artist

I wasn’t trying to be a disruptor. I was not trying for anything. I always kind of go with my natural gut, and I couldn’t do ugly makeup. I couldn’t do makeup that I didn’t think looked good, which was, at the time, really pale faces, contoured faces, over-lined lips, all this stuff. And I just started putting bronzer on their cheeks, and pinky blush… I wasn’t a painter. I was a beauty enhancer, right? And so I started realizing that there were certain photographers I probably shouldn’t work with and other people I should. So I started kind of finding my peeps, and my peeps were photographers like Bruce Weber and Patrick Demarchelier, who loved natural makeup. That loved this beauty, but didn’t want a painted person.

On how Bobbi Brown Cosmetics was started

I was working a ton. I was traveling, going on exciting editorial locations and striving to be the Vogue makeup artist. Seven years after entering the fashion industry, I got a Vogue cover. So that was a big deal. But at the same time, I met the love of my life, got engaged, moved to the suburbs, bought our first house, got a dog, and I just didn’t want to travel anymore because I just didn’t want to miss my husband. So I started doing more catalog work, which paid more money, but it wasn’t as exciting. And then my husband went to law school, so I needed to be home and I just started putting different things of importance in my life. I needed money, because my husband was in school, so I would take jobs, catalog stuff. And then I just started mixing makeup, which I always had to do, because there was nothing natural. And one day I went to a Kiehl’s Pharmacy on a shoot and I met the chemist. And he made these lipsticks. I’m like, ‘that’s amazing. You made these yourself?’ And he said, ‘yeah, I did.’ I said, ‘I’ve always wanted to make a lipstick that looks like lips.’ He said,’ I could do that for you.’ And I pulled out my taupe pencil and my creamy blush and whatever else and I said, ‘this is the color.’ He said, ‘all right.’ And he sent it to me and I said, ‘well, it’s a little this.’ So we sent it back a few times and then I finally got it. I’m like, ‘oh my God, this is what I’ve been dreaming about. I think people would like that.’ And then I realized not everyone has my color lips, right? Some people have pinker lips. Some people have, you know, browner lips. So, as a practical person, I said, ‘let me think of all the different colors that anyone could actually have the no-lipstick lipstick,’ which now I call nude. It’s a nude lipstick, but nude depending on your lip color. And then, when I got to it, he said, ‘you know, we could sell this.’ And I’m like, ‘yeah, we could sell this’ My models would buy it.’ And we made a business deal.

On the rising popularity of cosmetic surgery and medical procedures in beauty

I don’t think it’s a good trend. Botox became popular when I was in my 40s so I did it, and it was so bad. I couldn’t even believe it. One time I had an eyebrow that pointed up. Another time, I had an eye droop. I did it twice. Even though I was only in my 40s, it just didn’t match the rest of my face. So I said, ‘You know what? This is not for me. I’m not going to do it.’ And I’m so grateful because I see women who’ve been doing it their whole life and they look good, but something doesn’t look right. You know, things settle. Even if you don’t do it anymore, they settle differently. And for so many actresses, I understand how hard it is to be known for your beauty. And I’m not going to name names, but I look at them on TV, and I’m like, ‘Oh no. What happened? Oh no.’ And then I see these incredible women, and I just say, ‘Oh my God, you’re so beautiful… don’t take this the wrong way, you’ve had no work done.’ And they say, ‘Yeah, you could tell?’ I said,’ in a really good way.’ And I know some of them who have done little teeny, baby Botox and it looks fine, but guess what? In 5 or 10 years, if you keep doing it, it’s not going to look fine.

Write to Charlotte Alter at charlotte.alter@time.com.