MR Round Table: Female Entrepreneurship

The Writers | March 18, 2016

Three CEOs on the good, the bad and the advice

In honor of Love Your Career Month on Man Repeller, Leandra sat down with two fellow female entrepreneurs in the industry  — Maggie Winter, CEO of AYR, and Emily Weiss, Founder and CEO of Into The Gloss & Glossier — to real-talk about running growing companies.

Maggie Winter: Emily’s the first person I spoke to when we were spinning out of Bonobos, AYR’s former parent company, and setting AYR up as an independent company.

Emily Weiss: Which was only like a month ago.

Maggie: I know, and now it’s real.

Leandra Medine: Did she give really great advice?

Maggie: Yeah and it was honest. It was perfect.

Leandra: Yeah, I find that you give valuable advice.

Emily: I give advice very unfiltered and I feel like sometimes it would behoove me to put a little filter on it.

Maggie: Well, I think this is why you have the followings you do — it’s like having your best friend advise you, and whether it’s on a question like, “Which concealer is most important?,” or,”How should I finance this company?,” it’s cool to be able to go to somebody that you trust.

Emily: But with advice comes great responsibility. Because if you give someone advice about what they should do and then they do it and they don’t like it, you’re kind of the person who told them to do it. So I think that’s why therapists don’t actually tell you what to do, they just help you find the answer.

Leandra: Is that a common thing? I stopped seeing my therapist because I was like, “He’s not putting enough action plans in place with me.”

Emily: Yeah, they’re not like a life coach. Well, I don’t know who tells you what to do. I guess that’s your mother. A therapist is supposed to help you find your own conclusion. I just don’t think a therapist is ever going to be like, “Listen, it’s time for you to quit your job and start your own company.”

Leandra: That’s actually a perfect segue into how I wanted to start this conversation because I feel like there is a very common misrepresentation in culture right now — specifically among millennial women — that in order to be successful you have to…

Emily: Do your own thing?

Leandra: Yeah, you have to be a founder, an entrepreneur. The reality is, you can live a very fulfilling life working for someone else. But, there’s an escalating stigma around being a woman who hasn’t tried to do her own thing at least once because we’re living through the “Lean In” moment.

I want to hear your opinions on: number one, your own career trajectories and the hard stuff about your paths, and what advice you would give to someone graduating high school or college right now and trying to figure out what the right move is for them.

Maggie: So, speaking as the oldest millennial at the table, I came to the founder and entrepreneurial role totally Benjamin Button-style backwards. I’ve always followed what I love the most, what I’m most curious about, what I’m most passionate about, what I’m most interested in, and it’s led me here. I feel really fortunate to have been an employee first and to have been a member of a team for ten years before I was in the position to lead a team.

You can have entrepreneurial roles within a big organization. One of the things that I did when I was at J.Crew — which is obviously a big company — is spend time with startup and turnaround businesses within that organization. When Madewell was a new business, and when we were launching the kid’s business for the outlets, new divisions, new brands, it was a great way to learn with a lot of support. It was a nice balance of freedom and support. I think there is probably an impulse to go straight for the total freedom and want to haul yourself off the cliff, but it really is about instinct, validity and experience. And for me, having had the experience because I learned from people who’d been doing the job longer than I’d been alive was a wonderful education.

Leandra: What was the career trajectory? You graduated college, went to J.Crew…

Maggie: Yeah, I graduated college and I didn’t know what I wanted to do. I’d studied English, art history and film. I read a lot of great books and watched movies and looked at paintings and it was awesome, but I had no idea what I wanted to do and I was super jealous of the kids who were in engineering and nursing and business school because they were getting recruited and had jobs lined up. All I knew was that I wanted to live in New York City. I grew up in the smallest town in Pennsylvania — in Hershey, Pennsylvania. And I knew I wanted to live in New York.

I had a friend who worked at J.Crew, she passed my resume along. I interviewed with Mickey Drexler — at the time he interviewed every person he hired. Can you imagine that being your first job interview? And I got a job as an assistant merchant. I had no idea for the first six months doing the job if my job was to get my boss coffee or someday learn how to do what Mickey does. I had no idea. I ended up loving it because it was a wonderful place to work. It was also a job that is half art, half science, and a business where you learn by doing. I stayed there for almost eight years.

Then I met Andy Dunn, who founded Bonobos, and he had the chance to create a new line, a new brand, AYR. And that was the most incredible opportunity ever. At that point, I felt like it would be dumb not to take that chance.

Leandra: Did you imagine yourself running your own company?

Maggie: Two things I always knew I wanted to do were start a brand and lead a company. I didn’t imagine at the time that those would be at the same time or at the same company. But yeah, you always connect the dots backward and then it makes sense, right?

Leandra: You know what’s funny? For as much as I beat myself up over how much better of a “CEO” I should be, when I was younger, I never saw myself working for anyone else. I always saw myself building something new. I think I’m realizing right now that that’s not an instinct that should be taken for granted.

Maggie: Did you have like the ultimate lemonade stand when you were little? Or were you always creating things or telling stories?

Emily: I did.

Leandra: You had a lemonade stand?

Emily: No, I had a company called Clay Creations and More.

Leandra: Was it clay jewelry?

Emily: Yeah, it was clay jewelry and I printed my own business cards with stamps. I made the whole suite of stationary to accompany my business. I was more excited about the stationary than I was about the Clay Creations.

We sold out at the craft fair. I think my mom bought all of it, but we sold out.

And I wanted to open a store. I grew up in Connecticut and I wanted to open the coolest store in Wilton, Connecticut because there weren’t any. We didn’t even have a Starbucks or a movie theater in our town. It was very, very small. The towns around mine did — like Westport and Greenwich, all of these great towns were stylish. And I was like, “Come on!” So I wanted to open a great store that would carry Tocca and all those great brands of the early 2000s.

Leandra: You thought it was fashion for you, initially.

Emily: Yeah, but I always really liked art first and foremost. So like, making the clay jewelry — I think it was always a combination of creative, almost like art direction, in addition to the product. Because if you think back to the Clay Creations days, I wasn’t just making earrings, I was literally creating this whole presentation, the display. I’m really into the branding.

Maggie: Oh yeah. Clay Creations was a brand.

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Emily: Yeah. It was a brand. It was more than just the jewelry. I’ve always been really interested in story telling, not just the shoot and not just the clothes that are in the picture, but really the whole concept behind a shoot. When I graduated NYU, I got a job soon after assisting Elissa Santisi, who was Style Director of American Vogue at the time, and that was such incredible training in the art of story telling but also how it relates to business because we had budgets. And I was in charge of them. And me, the remedial mathlete in high school, was suddenly in charge of presenting Anna Wintour with a budget that was trying to fit a six page accessories shoot into thirty three thousand dollars, but needing to fly people to California, and rent baby animals for the shoot, and find a vintage Mercedes convertible for free. It was a lot of trying to fit square pegs into round holes to make the numbers work to execute a creative concept.

We always came in pretty much on budget. A budget is a budget and I’ve always really believed that. I believed that with my wedding, I believe that with my current business. We don’t fuck around with numbers. And I think that’s because money scares me so I just want to make sure there’s enough of it and that I respect it.

The training I received while assisting Elissa helped me understand how business gets done. It’s not just fun and games, it’s not just playing with clothes, it’s about having parameters. I have so much respect for the way Vogue works because they run a tight ship. Everyone knows what’s expected of them. You do your job well, it’s hard work, but it’s a great business. They’ve really created a great brand and great business, so it was a great environment to work in for two or three years with Elissa. And it really shaped the beginnings of Into The Gloss, which I started while I was her assistant.

Leandra: Did you always know you were going to launch a product?

Emily: You know, I forget. I have the worst memory so some days I say yes, and some days I say no. It’s not that I always knew we were going to launch a product, but the way that I’ve always thought about Into The Gloss and Glossier is that it’s a project and the medium shifts but the thesis or goal has always been the same. It’s just changing mediums and taking different shapes.

But the goal has always been to help women take ownership and authorship of their beauty routines, and to show women that you have enough information to make your own decision about not just your style, but about your beauty routine, your skin, your hair, you know? You don’t need a stranger to tell you about your own face. And I think Into The Gloss was the first phase of that, really, because it’s information. The first step was really, “Let’s start this dialogue. Let’s start this alternative way of looking at beauty and consuming beauty content and positioning beauty. Let’s do that first.”

Leandra: The medium through which you consume is changing but the thesis remains the same, which I think is very true of Man Repeller and true of all media companies. And I think that Glossier is in many ways still a media company.

Emily: Absolutely. Yeah, we’re a very content and context-driven brand.

Leandra: Right. Content definitely, but even more so community. The magic combination and what people are realizing is that it’s community and commerce that make sense together. It’s not really content and commerce. You could have a college-age girl writing a review of a product sitting behind a desk in a sterile office with no soul or you could be out there experiencing, building, and doing that honestly. Like you said  — with great advice comes great responsibility.

Emily: And I think that the best brands — if you think about the way brands have been built, especially luxury brands — want to redefine luxury. I think that luxury at one time meant, “We’re a brand that knows way better than you do and creates a beautiful product,” right? And that will never change. Luxury in terms of product quality is forever. But what is not forever is this approach of, “We will create something because we know best and we will not talk to you and we will sort of talk at you and throw this thing that we’ve created over a fence to you and you will consume it. But we almost don’t want to know who you are, or what you think about it.”

With Glossier, we’re really looking to democratize beauty by saying: You can have this really premium product, but it doesn’t have to look or feel intimidating. It’s going to be an amazing quality and just as great quality as many products, or better, but at a price that you can actually buy it again. You can use it every day and not be stressed out. You know?

I say this a lot, but we don’t want to just make people feel involved. They just are involved. We want your feedback, we want to see what you’re doing with the products, we want to invite you to our office. And even last night, we had an opening of our Phase 2 showroom that is going to be open to the public this weekend. And I met a couple of girls from the community — from our customers.

One came up to me, and something she said that I thought was so interesting was, “I was thinking about coming to this event tonight and I was thinking, ‘Should I dress up? Should I go home after work and shower? Should I put on high heels?”’ And she was like, “I didn’t because I just felt like, no, I don’t have to do any of those things. I’m just going to come from work and be exactly who I am from work and everyone else is probably going to do the same.” And then she said, “I was right. I came here and everyone was coming from work, everyone’s chill and happy to be here. You don’t have to dress up and become someone else to fit into a Glossier party.” I thought that was really interesting that she got that, and she was right. She was like, “I’m accepted, just after work.”

Maggie: There’s a new girl out there.

Leandra: Totally, I was going to say that with the turn of a new generation comes a new series of intolerances. One of them is inauthenticity. There needs to be connection between the person and the thing and because so many more women are working, there’s this sort of chameleonic peg in relation to how a woman’s life happens. Phoebe Philo of Céline really tapped into that for an upper echelon and in many ways, AYR is doing that for the rest of us.

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Maggie: Yes exactly. Céline is incredible, but to be the accessible Céline, where’s that? This girl, by the way, there’s nothing she can’t do. She’s not limited in any way, not by a label or a logo. She doesn’t want to be dictated to, she doesn’t want to be transacted to. And I think that’s where it’s exciting for brands like AYR and Glossier because we intuitively understand how she lives.

Leandra: We’re her.

Maggie: And it’s not about occasion-specific dressing and it’s not about dressing for anybody but yourself. And dressing is a reflection of the lifestyle she’s leading. It’s a crazy 18-hour day, she’s always going, she’s always on. One of the things I hear over and over from AYR’s customer is, “I’m not a fashion person.” Meanwhile, she knows Dries, she knows Jil Sander. She knows Phoebe Philo, she is aware of all of this, she just has real purpose and interests and passions in her life and doesn’t define herself by one label.

Leandra: Well, that insecurity, the “I’m not a fashion person,” is a wall that Man Repeller is breaking. Don’t feel embarrassed that you’re interested in Phoebe Philo just because you’re also a paralegal — that’s backward.

Maggie: Exactly. The most interesting people in the world are people who aren’t all one thing. And I think that is hands down our brand’s biggest inspiration and it’s why we started this company: we felt like there wasn’t a go-to uniform for this next generation “Girl Boss.” And “Girl Boss” doesn’t necessarily have to mean female CEO by the way, it’s the spirit of, “You can do anything.”

Leandra: What’s interesting about both of your companies — and about Man Repeller, and the reason why this conversation is especially compelling to me — is that we’re hitting these women from three different directions but are ultimately saying a very similar thing, which is just: be who you are.

Emily: Can I just add that for us, our mission, essentially, is that it’s more than just who you are, it’s being proud of who you are. You know, really feeling a sense of pride about your journey. It’s one step past acceptance, you know?

Leandra: For me, pride is inferred by being comfortable in who you are, but that’s obviously an important point to make explicitly. So, what advice are you giving to this girl if she is running through that eighteen-hour day and hates her job and can’t quite figure out what to do next? Or to the girl who is really, really confused because of the concept of optionality? She could literally be doing forty-five different things in the span of one second while sitting at a desk.

Emily: It’s also like how people say that when it comes to marriage and dating, especially in New York (I hear this often — I haven’t necessarily experienced this), you are constantly looking for the next best thing.

Leandra: Totally!

Emily: That definitely happens with work. I haven’t experienced it — I created this company that I have been doing since I was 25-years-old, and when I am thinking of the next best thing it’s always for Glossier, not for Emily. But, I think that it happens and it’s destructive and it’s the millennial curse.

Leandra: Do you think that it’s just a millennial thing and not necessarily a New York thing?

Emily: It could be both. You know you can go to New York and “make it” and do anything you want. But I think what is so important is learning and training. I recently learned how to ski. And I was on the lift with this man in Great Barrington, Massachusetts. I was looking down at all the skiers and I kept seeing all these little kids. Really tiny kids, in front of me at the chairlift. Scooting along, three feet high. I asked, “How old are these kids? How old do you have to be to start skiing?” And I think he said, “Four or five.” And I said, “What’s the earliest you’ve seen?” And he said, “Three, three and a half, but that’s really wrong because their brains don’t get what they’re doing. They’re on the skis, slipping and sliding around and that might help them not be afraid of snow or whatever, but they’re not going to be able to ski.”

The brain is not fully developed enough yet to be able to learn how to properly ski. That was interesting in the context of — you know — how I think about my career. I needed those three or four years out of school to really learn how businesses work and get that first hand experience before I was able to start my own thing in the right way. And who even knows if I started my own thing in the right way? Who knows where we would be if I’d had five more years of experience.

Leandra: Well, isn’t the other thing that there is no such thing as “the right way,” really?

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Emily: There’s no such thing as “the right way,” but there is really something to be said for experience. And I think it’s overlooked. Life experience, becoming older and wiser and learning.

Maggie: The other thing that you learn is that regardless of your role on the team, what you do is super important to your happiness, but who you do it with is equally important. Surrounding yourself with people who you can learn from, who are better at things that you are weaker at, who you love being around and who you trust and respect — regardless of what you do — is the most important part of the equation.

Leandra: Well, it’s another form of marriage.

Maggie: Yeah! We are talking about founding businesses and being entrepreneurs, but it’s nothing without a team. And that is something else you learn when you’ve had a few different roles first.

Leandra: I think on the topic of choice, I was having a conversation with Ricky Van Veen — the founder of College Humor — on Tuesday, who recently got married, so I asked him about the most salient difference.

He was like, “Well, when we get into an argument, there’s no such thing as, I am going to walk out of here; this argument could end the relationship — you are forced to become more solutions oriented.”

And I sympathized with it and had never articulated it that way, but realized that this is actually a really interesting point on the topic of choice. Because even though the underlying message of,, “You can be who you want to be and you have all the choice in the world” is a strong one — it’s supposed to empower us to feel like we can do whatever we want to do and like if we’re in bad situations, we can absolutely get out. But it can also be quite paralyzing, because you will duck out more quickly if you aren’t comfortable in a situation instead putting in the work. Rolling up your sleeves and being like, “I have no choice but to figure this out.”

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Maggie: I think that’s the second part of it. It’s, “You can do anything. But you have to do it.”

My parents raised me with that sensibility. “You can have whatever you want, but you gotta get it for yourself.” There is definitely — in the millennial context — a heavy tendency toward the innovation side of the spectrum. But the discipline side is the side that makes the difference between a great idea and a great business.

Leandra: And a great execution.

Maggie: Exactly. There’s a spectrum of discipline and innovation, whether it’s old school to new school, and we see it in all of our industries. You’ve got to have both. It’s so refreshing and exciting to see that there are people out there going, “No, there’s a better way to do this. This is totally fractured and broken and there’s a new consumer who wasn’t there when we were starting our careers and we get her, so let’s make something for her.” And that’s great! But actually making it is difficult. And when we first started talking about this, Emily, I remember the advice that you gave me a few months ago was, “It is really hard. It’s hard.”

Emily: [Laughs] That’s not advice.

Maggie: Exactly! That’s just fact! But it’s true.

Emily: It’s sort of like birth. That’s how I think about a creative process. There’s a great Ted Talk that Elizabeth Gilbert, author of Eat, Pray, Love, did on the origin of the word “genius.” Now we say that “a person is a genius,” but that’s not actually the origin of the word, she explained.

“Genius” is based on the word “genie,” which in Greek mythology was a tiny fairy that would hook onto individuals at different times in their life and give them a stroke of genius. It’s not a permanent characteristic, you’re not a genius forever. You are a genius maybe once or twice in your life. It was literally up to a fairy. It was a gift.

Maggie: I think one of the things that people who have done this will tell you is that it’s a wild ride. The highs and lows that you experience are unlike anything else you’ve experienced in life. I am not an adrenaline junky looking to throw myself off of a cliff and take a risk but business is about taking calculated risks at the right times.

With the skiing analogy, if you are too little, you don’t really know what you’re doing. If you’re too old, you’re afraid to fall and you’re never going to actually be able to learn because you tense up and you can’t move your body the way it’s meant to move. And I feel like we’re holding onto this moment where there’s an opportunity. We have enough experience, we have enough support around us, to go into the unknown. And make something that didn’t exist. I couldn’t have done this 10 years ago and I don’t think that 10 years from now would be the right time either.

Leandra: Yeah! We’re like avocados. There’s a short window whereby we’re good to eat.

Maggie: That’s perfect. Genius just struck.

Leandra: I hope that’s not my genius striking.

I know that the people who are reading this story are going to want pointed advice.

Emily: We have now hired 40 people who work at Glossier. So I feel like I am always getting a little bit better at hiring. I always look for something a little bit different, not just in people’s roles but in an interaction. And I look for people who go above and beyond. There’s a job description for any job, hopefully, and you can go to work every day and look at your job description at the end of every day and say, “Okay, did I do this and this and this today? Okay yes, I have done all of these things.” But there is a thoughtfulness that I think is required that separates exceptional and really top talent people out. And that is the next layer above everything you do: it’s the connecting of the dots that happens from doing all that stuff. You know what I mean? There’s an added layer of thoughtfulness that I look for in people.

Leandra: Piecing the threads together.

Emily: It should be relatively easy at a performance review to look and say, “Okay, did you do this, this and this?” But somehow your manager could still be unimpressed. It’s like, “Okay, you did all those things, but what did you come up with? What learnings or innovations or critical thinking have you done above all of those things that has propelled our company forward?”

Because when you’re a team of 40 people in a small business, every person counts. There’s no one person who is more important. The advice that I would give for anyone who is just graduating or going into the work force is to become someone who really matters, wherever you are. And if you’re not allowed to do that — meaning if the job doesn’t let you do that critical thinking — then after you have aced all of your job requirements — because that is the first step, you have to crawl before you walk — and you are still not in a place where you can do more, then go find that place where you can do more. But I think you should be that person who does more. And who is really thoughtful. That’s important.

Maggie: Absolutely. I think there are a lot of traits that make you valuable and good at what you do: accuracy, accountability, anticipation, adaptability. But the most important thing is resourcefulness. So whether you are an analytical mind or not, being able to figure stuff out makes you indispensable. And that’s what you’re talking about: making yourself indispensable.

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The other thing, and I wish someone had told me this when I was jealous of the kids in nursing school or business school or engineering, is that the world needs whatever you are into. Whatever you’re obsessed with, there is someone else out there who needs that. Believe very much in what you are good at. Focus on what you are good at. Don’t try to be the best at everything. Being well rounded isn’t the most important thing. Obviously you don’t want to be an asshole but focus on what you’re best at.

What you enjoy doing is usually a good indicator of that because being good at something feels good and that fuels that feeling of productiveness. So find what you are best at and somebody who needs it and gain experience. Be open and surround yourself with good people, and find people you can learn from.

The best people in my career — and I feel this about the AYR team for sure — they are people who are not just going to teach you how to do your job well, but people who are also going to teach you how to be a good person. Integrity matters. Pick partners and employees and bosses who are going to teach you about life. Work and life are one thing. We were talking about this new generation where everything is completely unlimited. There’s no work/life balance. It’s not like I go to my career and I wear this outfit and then I leave and change into my other clothes. It’s all one thing.

Leandra: That’s why for me, having your personal goals and your business goals align is fiercely important.

Emily: I think you also touched on something really important, which is that your career is really long. And the world is very small and reputation is really important. The easiest way to have a great reputation is to be respected and to be nice. You can’t control whether or not people like you — it’s so futile and it’s not about being well-liked — it’s about being well respected because you do a great job while being a nice person. If you are a nice person and you are polite and you do a great job, that’s a winning combination.

We should also keep in mind that this is a very New York-centric conversation. There are women and readers who do have to wear uniforms to work and don’t have opportunities to critically think beyond what they are doing because their job is very specific. We are fortunate to live in a city where the opportunities are endless and upwardly mobile; throughout the country and the world, that is often not the case. Sometimes you have to just do a job. And that’s why it’s important to work with people you like and be nice and hardworking. But I don’t think that necessarily changes your feelings about yourself, personally. You can still enjoy brands like AYR, or Glossier products, or read Man Repeller and feel content that you are doing a good job at work.

Leandra: Before we wrap this conversation, I feel like a lot of our talk revolved around the lessons and glory of being an entrepreneur and working hard. But what is keeping you up at night? What is making getting out of bed difficult? When you are super overwhelmed, why is that?

Emily: I mean, specifically right now, I am worried about our supply chain and running out of inventory. It’s a good problem and a bad problem. But how I overcome that is trusting the fact that we have a killer team in place who is worrying about it probably even longer hours than I am worrying about it. And so I trust in them and delegate to them, knowing that they’re working on it. I think the hardest part at this stage of where our company is at — and it changes, but when you are just starting a company, the peaks and valleys occur much more rapidly. The further along the company is, there starts to be a little more distance. Maggie, you are probably having a heart attack at least four times a day at this point.

Maggie: You can’t underestimate how hard it is and if it were easy everyone would do it. I have so much respect now for other founders, entrepreneurs, CEOs, parents, leaders, teachers, people who are responsible for the well being of a group of people. I have so much respect now for my own parents because you want to protect your team as much as you can and be like an umbrella or shield. And when there is no person ahead of you…my whole career I’ve had somebody ahead of me to absorb the shock and clear the path and lead the way, and we don’t have that now. There is glory to it, but it’s also scary as hell.

Emily: And isolating. There’s that phrase, “lonely at the top.”

Maggie: Right. The thing that has been keeping me up is that I am one person, we’ve got a seven person team and there are all these things on the team that I am not an expert at. There are all these elements to the business where I know somebody knows better than I do. Building the team out was such a priority. That’s the other thing: you have to know that it feels like it’s all your responsibility, but it’s not. Burden shared is a lesson and you find people who are good at other things. There’s a spectrum of skill sets and as long as there are two people for every problem, you can figure it out. This is where the resourcefulness comes into play.

Leandra: It’s transformative…

Emily: Totally transformative. Absolutely transformative. And I don’t think I had fully comprehended the idea of team before last year. I don’t know why, we have been very small before. And to have that group — we are able to do anything.

Maggie: Yeah. I think one of the things you realize pretty quickly when you have been responsible for financing a company and building a team and running a P&L [profit and loss sheet], is that the goal is the privilege to continue to do it.

Emily: Yup. It’s like earning your right to go to the next level.

Maggie: It’s like Miley said, “It’s the climb.” It’s not the exit, or the one accomplishment. You keep going.

Emily: I totally agree. And you can’t keep going until you have that team and that infrastructure.

Maggie: Andy [Dunn, of Bonobos] gave me advice once, he said, “Try to imagine yourself as a grandmother looking back on yourself now at this moment in your life. It feels overwhelming, but when you look back this is a moment in time.” And it’s so hard to do that. It’s so hard to imagine looking forward and looking back.

Leandra: When we are inside a moment we don’t realize that just like everything else, it’s temporary.

I try to think of the hard parts as the most difficult bouts of exercise in a class. I’m on the fifteenth burpee and there are still thirty to go but they are going to end. Just get through them. You will be a much better person for it. It will be uncomfortable, but you will not die.

And if you’re the kind of person who tends to spiral, it’s really important to notice the neurosis setting in. And then manipulate yourself into this belief — and by the way it’s not a belief, it’s a reality — that everything is temporary. Nothing is a life sentence except for life itself. It’s a comforting thought.

Check out Emily’s modern beauty website Glossier and Maggie’s clothing website AYR. You can also follow both @glossier and @ayr, too.

Leandra is wearing a Rosie Assoulin jacket, Comme des Garçons shirt and Sonia Rykiel jeans. Emily is wearing a Saks Potts t-shirt (similar here) and vintage Levi’s 501 jeans. Maggie is wearing an AYR coat, cami and jeans; Photographed by Krista Anna Lewis; quote slides collaged/illustrated by Emily Zirimis. 

man-repeller-bar-female-entrepreneurs

  • I agree, there is such thing as perfect avocado slot 🙂

    There could also exist a … comfort curve: you risk, you suffer, you work and worry too much, all of it for a few years if necessary, but after some time, some steadfastness, some reliable success, ease of thinking and acting, some comfort and certain lightness of it all need to come up, not just as a reward, but also because our bodies and minds probably need relief and some really nice treatment by HRH Reality after all this time. I don’t know that I would stand it if nothing felt better now than in the beginning and I didn’t feel a certain comfort in doing my job (am not pretending that freelancer is the same as real entrepreneur but I have certainly come a long way, so …).

    • Kimberly Sickels

      When I saw the draft of 4558 dollars,,,rd I accept that my friend’s brother was like really generating cash in his free time with his PC. . His aunt’s neighbor has done this for only 10 months and by now repaid the loan on their home and bought a new Car .

      To Know More Click Here
      uj…

    • Jessica Davis

      When I looked at the draft of 5936 dollars, I have faith that brother of my friend was like really generating cash in his free time with his PC…uo His aunt’s neighbor has done this for only 11 months and by now repaid the loan on their home and bought a new Car. Look here for details.

      For Details Click Here
      bt..

  • Cool girls!

  • That avocado theory keeps on giving and giving!! I need to read this over when I’m not at work, but I very much enjoyed this round table. The be who you are and be comfortable with it mantra will never get old. Thanks for creating three worlds where you can be reminded of that each day. oh and Emily, if you’re reading this, my glossier concealer/lipstick got delivered to me today. I look awesome so thank you!

  • Amelia Diamond

    I LOVE ALL YA’LL WORDS OF WISDOME

  • Living Paula Blog

    I loved this interview. Thank you for sharing.

    Paula- http://www.livingpaula.com

  • bestie

    wow. this couldn’t have come at a better time for me. thanks for all the food for thought! such inspiring words–such inspiring women.

  • Suz

    Hi thanks for the convo and also the jobs/career theme I’m definitely needing it rn (my mum recently sent me this book…) but I have a very important unrelated Q- what brand/style are Leandra’s sunnies?

    • Leandra Medine

      Haha hi! They are Garett Leight and called “Brooks”

  • I LOVE reading about girl bosses. It’s inspirational. I did want to throw in a quick quip about experience, though. The three of you ladies gained quality experience. But as a millennial, I have quite often come across older people that continue telling me “experience is quality” and they’re better because they have “more experience”. But I think quality is experience, and not the other way around. I know people who are so much less competent than I but are seen as more important for their years of “experience”. And I think women, and young people in general, can’t fall for that trick. Because some of us will have awesome mentors that teach us and we are the types of people that want to learn. But others won’t have that, and will instead be made to feel lesser.

    Maybe I’m ranting, but I just wanted to throw that out there. Because as someone who does aspire to being her own boss, I’ve been made to feel less experienced even though I clearly knew how to do things better.

  • EP

    Hello wise women. I have an engineering degree and I am currently an editor for a trade publication in my industry. I, like many others, am a multifaceted human who can get down reading a scientific journal article, a Man Repeller blog post, or a political opinion piece. Although I enjoy many aspects of my job, I am certain I would be happier and find more success working in fashion or retail. Any advice for someone with a nontraditional background whose credentials can’t be written as bullet points on a resume?

    • Leandra Medine

      why don’t you send this very comment around to the places you want to work? If you don’t know where you want to work id recommend writing a list of like, 5 role model companies you’d feel proud to be part of and then harass them all. We hired our head of audience development after she found out our office address, write a letter and sent her resume in an envelope

      • MM

        Good advice. However, you can harass all you want but, unless you have the necessary qualifications or know someone, the likelihood of getting your foot in the door is super slim. I bet, if your Head of Audience and Development lacked the experience/strong credentials, you probably wouldn’t have hired her. Unfortunately, it seems no company has the time to train or provide much guidance. I’m in my early 30’s living the experience struggle. P.S. Congrats on prompting a lurker (me) to engage in the conversation.

  • Efua Odafen

    What a discussion!!! This is one of the most fulfilling reads this month. Inspiration woman goals.

  • Kylie

    Incredibly inspiring and encouraging. Such great content. ??

  • Stefani D

    Would have loved this in a podcast!

  • I.AM.IN.LOVE.WITH.YOU.
    ALL.OF.YOU.

  • Charlotte Delon

    this was such a great, motivating read! I graduated back in 2014 and definitely put the pressure on myself to be a founder or entrepreneur and this post has given me a new perspective on work. thanks MR!

  • Kate

    i really loved the beginning bit about how (even tho y’all are a bunch of ceos/founders) not everyone necessarily has to create something like that and can be happy working for someone else. i liken it to something one of my fav profs said when i started my master’s program and was sure i was eventually going to get my phd: “don’t get a phd unless you have a burning research question that can’t be answered without one.” (i.e., start a company that does something you think none other does) of course, this advice is now useless because my program is almost finished and i DO have a research question that i’d need to get a phd to fully answer the way i’d like so…….

  • Jen

    This was so inspirational! I l run a super small business and it’s nice to hear such successful and inspiring people have the same feelings as me. I also love that I can hear your voice through your questions.

    p.s.- I recently discovered that after an avocado is at it’s perfect ripeness, you can stick it in the fridge and it was stay like that. Perfect avocados all week! Seriously blew my mind since I can’t live without them!

  • Chi Huang

    Super inspirational! I even printed it out…..

  • Lovey Fleming
  • <3 <3 <3

  • this is AWESOME! “But the discipline side is the side that makes the difference between a great idea and a great business” This direct quote permeates the tone of the entire roundtable. You each have great ideas with also versatile talents but the key component is the discipline to execute. Bravo.

  • Savannah

    What a good read! Interesting and inspirational not just for aspirational entrepeneurs. I also believe that to really stand out at a company as an employee, your job doesn’t really end when you leave the office. I’m currently an intern at a large fashion company and had the pleasure to listen to the managing director of LVMH at my university a while ago. He touched on this briefly and said it basically comes down to being completely obsessed about what you do. Makes sense, when you’re obsessed about something that extra step will always come naturally. Anyway, you guys write about it better than I do, thanks!

  • Yeeaaaaaah these conversations are the best. Thank you for posting them! Terri x

    https://thecactusmag.wordpress.com/

  • Sooo good! I keep for myself the sentence “The magic combination and what people are realizing is that it’s community and commerce that make sense together”.

    This Career Month at Man Repeller is great…

    http://www.mgluxurymarket.com

  • my favorite parts that I would email to everyone even though I need to hear it just as much as everyone else:

    *******
    Maggie: “You can do anything. But you have to do it.”

    My parents raised me with that sensibility. “You can have whatever you want, but you gotta get it for yourself.” There is a heavy tendency toward the innovation side of the spectrum. But the discipline side is the side that makes the difference between a great idea and a great business.

    Leandra: And a great execution.

    Maggie: Exactly. There’s a spectrum of discipline and innovation, whether it’s old school to new school, and we see it in all of our industries. You’ve got to have both.
    *******
    Emily: I think you also touched on something really important, which is that your career is really long. And the world is very small and reputation is really important. The easiest way to have a great reputation is to be respected and to be nice. You can’t control whether or not people like you — it’s so futile and it’s not about being well-liked — it’s about being well respected because you do a great job while being a nice person. If you are a nice person and you are polite and you do a great job, that’s a winning combination.

    *******

    Maggie: Yeah. I think one of the things you realize pretty quickly when you have been responsible for financing a company and building a team and running a P&L [profit and loss sheet], is that the goal is the privilege to continue to do it.

    Emily: Yup. It’s like earning your right to go to the next level.

    Maggie: It’s like Miley said, “It’s the climb.” It’s not the exit, or the one accomplishment. You keep going.

    Emily: I totally agree. And you can’t keep going until you have that team and that infrastructure.

    ********
    Leandra: And if you’re the kind of person who tends to spiral, it’s really important to notice the neurosis setting in. And then manipulate yourself into this belief — and by the way it’s not a belief, it’s a reality — that everything is temporary. Nothing is a life sentence except for life itself. It’s a comforting thought.

  • Roxi Fernandez

    loved this. and loved the graphics!!!

  • “Well, when we get into an argument, there’s no such thing as, I am going to walk out of here; this argument could end the relationship — you are forced to become more solutions oriented.”
    My favorite part. So true. When you’re the boss, it’s about problem solving.
    Some people assume all women are too emotional to make logical decisions in moments of stress. We’re proving them wrong. 😉

  • Leslie Scott

    So so good! Going to print out and get out the old yellow highlighter! As a stay-at-home mom who is struggling creatively with being the CEO of our home (and not using her two degrees), this was the first article that I’ve read by real ‘girl bosses’ that has resonated with me. Didn’t address any of my struggles directly but somehow did at the same time?? Anyway, lots to take away and think about – thanks!

  • Vickee

    Every time I read a round table, I always leave incredibly inspired and ambitious 🙂 Thank you MR!

  • Thanks all for sharing your experiences and honesty!

  • Priscila Menezes Siqueira

    MR Round table: new podcast!!!

  • The Keep Collection

    Dear boss ladies,

    I have just started a clothing company & online journal of my own (www.thekeepcollection.com) at the crazy infantile age of 25, & I cite all of you as inspirations, so this is a dream roundtable for me. There’s little I identify with more than: “the goal is the privilege to continue to do it” (thanks, Maggie!). This will be a great resource for me on the hard days & the great days, and I want to thank you all for it.

    Kudos for doing what you do & letting us all in on it. xo

    Susannah Emerson
    CEO/Creator, The Keep Collection