M.M.LaFleur: Sarah LaFleur

When she was working corporate jobs in New York City, Sarah LaFleur hated getting dressed in the morning; the choices in her closet felt overwhelming, many items didn't fit right or wore out too quickly. So in 2011 she launched a line of clothing for working women that would be simple, elegant, and well-tailored. She had no experience in fashion but partnered with a top-line designer, Miyako Nakamura, to create M. M. LaFleur. Today it's a multi-million dollar company with loyal customers from Capitol Hill to Silicon Valley. PLUS in our post-script "How You Built That," Taylor Mali explains how he created Metaphor Dice, which ease the pain of writing the first line of a poem. See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

Speaker names marked ? are inferred from speaking time and the show’s known hosts — they are not voice-verified.

• 0:00Guy Raz?

  So really quick before we start the show, we are coming back to Seattle and to San Francisco for two How I Built This live shows. Details on the guests will be announced very soon, in the next few days. It's so exciting, it's hard for me not to tell you. But if you want to find out more about it, please follow us on Twitter or keep checking nprpresents.org to find out more. Tickets will go on sale later this week.

• 0:26Speaker 01

  We still continue to do trunk shows. We had revenue goals for the month, and so if we weren't meeting our revenue goals, then we would, you know, set up a trunk show, stat.

• 0:35Guy Raz?

  Right.

• 0:35Speaker 01

  But online, it was just a totally different story. We could not sell our dresses.

• 0:40Guy Raz?

  I have to assume your cash reserves are getting close to running out.

• 0:44Speaker 01

  Not only did we run out, it actually went into the negatives. Our bank account, I think at one point, said like negative 2,000 or something, and I didn't know you could draw down beyond zero. So that was a wake-up call.

• 1:02Guy Raz?

  From NPR, it's How I Built This, a show about innovators, entrepreneurs, idealists, and the stories behind the movements they built.

• 1:13Guy Raz?

  I'm Guy Raz, and on the show today, how a relentless morning routine inspired Sarah LaFleur to build a simpler wardrobe for women, a multimillion-dollar brand called MM LaFleur.

• 1:31Guy Raz?

  Back in 2004, an American psychologist named Barry Schwartz published a book called The Paradox of Choice. Barry's argument, and we've talked about it before on the show, is pretty straightforward. He concluded that having lots and lots of choices has actually made us more anxious and less happy. I mean, think about it. Do you ever get anxious at Chipotle or In-N-Out Burger? I'm guessing you don't, because they have very few choices: burger, cheeseburger, double cheeseburger, taco, burrito, bowl, quesadilla. You get my point, right? Having fewer choices actually decreases anxiety.

• 2:08Guy Raz?

  Now imagine waking up every morning and agonizing over what to wear. You go to your closet and you either hate everything in it, or you can't decide what would look good. And I suspect this is not a thought experiment for many of you. In fact, this was how Sarah LaFleur started her day every morning as she went off to her corporate job at a firm in New York. And Sarah wasn't alone. The research is pretty clear. On average, women spend a lot more time getting ready in the morning than men. So Sarah decided to try and tackle this problem by tackling the closet, essentially by coming up with a line of clothing that was simple and elegant, without too many options, that

• 2:49Guy Raz?

  would speed up the morning routine, clothes that were well-made, looked great and professional, at a more reasonable price. But like so many of the founders I've talked to, Sarah had this ambitious plan and not the slightest idea, initially, of how she was going to carry it out. For starters, she knew nothing about the fashion industry. She had no idea how to make a dress or a pair of slacks. She just knew what she liked. But since she launched MM LaFleur, it's grown into a business closing in on $100 million in annual sales. And a lot of the company's designs are inspired by Sarah's childhood in Asia. Her dad was an American diplomat, and for most of Sarah's childhood, the family lived

• 3:33Guy Raz?

  in Japan, where her mother was from. And Sarah grew up speaking both English and Japanese.

• 3:39Speaker 01

  It was tough. The term that people use in Japan to describe biracial kids is "half." I guess we say that too, half-Japanese, half-American. But my parents always said, "You're not half, you're double. You're both Japanese, and you're also American." And so I think they were really insistent on that fact. But I think on a day-to-day basis, like I remember when I was in Tokyo, I really didn't want to use my last name LaFleur. In Japan, your last name really signifies whether you are Japanese or not, so much so that Korean-Japanese people or Chinese-Japanese people, they will change their last name to signify that they are truly Japanese. And so I kind of hid my American last name. And then I would say simultaneously, when I came to the US, I had the opposite experience, especially around college.

• 4:23Speaker 01

  I went to a school that was incredibly preppy, and that prep culture I'd never seen before in Japan.

• 4:28Guy Raz?

  Tell me about your mom. Did she work?

• 4:32Speaker 01

  Yeah, she did. And I mean, really, a huge inspiration. I mean, I would say the reason I started my business in many ways goes back to my mom. She is Japanese, raised in Japan, and, you know, very, very unusual person for someone of her generation. She worked throughout her life, continues to work today. She loves her job. She runs a business selling travel jewelry out of Tokyo, which she started because I think in many ways, it's tough being a diplomat's wife. You have to move every three to four years. And I think the common assumption is that the wife usually gives up her career so that she can, you know, be the diplomat's wife, host receptions, et cetera. But she couldn't, she always says, I can't wait for Monday, which, you know, your kids are like, what?

• 5:17Speaker 01

  Excuse me? Like, how about us on the weekends? But she just, she loved going to work. And I think that was a real inspiration for me and my sister. You know, we never assumed that we would not get jobs. That was the only thing we assumed.

• 5:31Guy Raz?

  So, I mean, looking at your mom as, as this kind of inspiration for how to be an entrepreneur, did you, I mean, I can't imagine as a kid, you thought, I'm going to be an entrepreneur? Or, or did you? I mean,

• 5:43Speaker 01

  Oh, God, no.

• 5:44Guy Raz?

  Yeah.

• 5:45Speaker 01

  No, not at all. I mean, she didn't hide how hard it was, trying to start the business with her friends, having her friends leave the business all of a sudden, out of nowhere. Financial struggles, just hard, personal conversations that she was having with her business partners. And I remember as a kid, I would come down in the middle of the night to grab a glass of water, and I would see my mom sitting in the armchair with a light above her head, sipping whiskey on the rocks. And I just remember thinking, wow, it is hard.

• 6:20Guy Raz?

  So, when it came time for you to go to college, you went to Harvard's. I mean, you must have been, you know, a pretty good student.

• 6:28Speaker 01

  Yes and no. I think I never fancied myself to be this super smart person. I knew I was a really hard worker. And my mom always used to say, you know, this is in Japanese, "Doryokukan no sarachan," which means like, you're the kid who tries hard. And so, I, my mom meant that in an encouraging way, but I never in my mind thought like, well, you know, I'm going to be the smartest person in the room. I've actually, I've probably never thought that in my life. I just knew that whatever I wanted to do, it would have to be through sheer willpower, sheer determination.

• 6:58Guy Raz?

  Yeah. I mean, when you graduated, what did you think you were gonna do with your life? Did you think, okay, I'll get a job and go work somewhere and figure it out?

• 7:08Speaker 01

  I should take a step back and say, like, basically, from the time I was in high school, I wanted to become a refugee camp officer. I wanted to be a logistics officer. And I started researching refugee issues, got really, really passionate about it. And then I thought, gosh, that's what I want to go do. And so the summer between my junior and senior year, I had this opportunity to go volunteer at a refugee camp in Zambia.

• 7:33Guy Raz?

  Wait, you did this while you were still a student?

• 7:35Speaker 01

  Yeah, yeah, yeah, yeah. You know, I think if I can point to one life-changing experience that I've had, that would definitely, that would be the one. I mean, this refugee camp was, I think, like, 10 hours from Lusaka, which is the capital of Zambia. So we would drive to the small town that was two hours away, and I would buy random pieces of furniture there, and then we would, you know, paint this building that we fixed. I mean, it was, it was basic stuff. It was, it was basic stuff. But I think I also, I think simultaneously, I realized the powerlessness of it, of myself, really being in that space. I would have people come up to me, just as I was, you know, walking back to the dorm where we were staying, and he would say, I have AIDS, my, my wife has died, I have

• 8:20Speaker 01

  one kid who's dying, is there any way you could help me? I mean, this, you know, and this would just happen on a daily, if not hourly, basis. And it just fundamentally changes the way you see life. And I went with this nonprofit organization, and one day, the leader asked me, okay, so we are, we're short on money, and so we're gonna have to make a trade-off. We can either continue to buy lunch, or we can continue to spend on fuel. And I was looking at him, being like, wait, we have to choose between lunch and fuel? What kind of a choice is that? Like, how are we supposed to work like that? And then I came back on campus, senior year, I had all these friends who were coming back from their investment banking internships with $5,000, $10,000 signing bonuses.

• 9:05Speaker 01

  And I just, like, couldn't believe the, like, you know, that was more than the money I had raised all summer. And it sparked some sort of curiosity, I think, for me. And then a mentor that I had, who I'd been with at the camp at the time, she was someone who had worked in investment banking, and she said to me, you know, Sarah, it's, it's never a bad idea to go learn how to work with the big boys. Kind of hate that expression, big boys.

• 9:30Guy Raz?

  Yeah, yeah.

• 9:31Speaker 01

  But I knew what you meant. And the money, I just couldn't believe that you could sign a piece of paper and you could have $5,000 in your checking account.

• 9:39Guy Raz?

  Yeah, and I guess you sort of got drawn into that because after college you went into consulting, right? You went to work at Bain.

• 9:48Speaker 01

  Yeah.

• 9:48Guy Raz?

  And what did you do there?

• 9:50Speaker 01

  I was what was called an associate consultant. And you are working on a case, which if you are at a company like Bain, it's usually for a Fortune 500 company. And you are trying to solve a problem that the company presents to you, which might range from, you know, anything from we're trying to enter a new market, how should we do that, to we have to cut costs, how should we do that?

• 10:14Guy Raz?

  Yeah, I mean, a lot of the, you know, a significant percentage of people who've been on the show, I'd say more than 10%, worked in consulting for a couple of years, early in their careers, where you're basically paid to learn everything about a business in order to give them advice for how to be more efficient or to run a better operation.

• 10:33Speaker 01

  Yes.

• 10:34Guy Raz?

  And then oftentimes, these, you know, people who were in consulting are sitting around saying, wait a minute, I think I could do that better. And they go on and they start a business. But it is actually really useful. I mean, it's super helpful in kind of training you and giving you expertise in an industry that you otherwise would have known nothing about.

• 10:53Speaker 01

  It's so true. You know, I mean, I didn't know how to do really basic things. Like, I didn't know how to write a business email. I didn't know how to do PowerPoint. That's like, that's a life skill. But they whipped me into shape. So it really, I think, set a certain standard for me that I knew I had to meet if I wanted to be taken seriously.

• 11:14Guy Raz?

  So you, I guess you stayed at Bain for about three years, which is, I think, the sort of the average length of time, unless, you know, for people who decide that they want to make a career out of it.

• 11:24Speaker 01

  Yeah, that's right.

• 11:25Guy Raz?

  And you got this opportunity to go to work in South Africa. You must have been 25 or 26. What did you, what did you do there?

• 11:34Speaker 01

  I worked for a nonprofit called Technoserv. So that was started by a bunch of former McKinsey partners. And the idea was that South Africa had a really, really interesting challenge. Having gone through apartheid, you have this dual economy. You have the white economy and essentially the black economy, and the two operate incredibly differently. And the question was, how can we get the black South African farmers to plug into this incredibly successful supermarket economy? That was what I was working on. And so I ended up spending over a year with them, I guess.

• 12:11Guy Raz?

  And, I mean, was the idea just to be there for about a year and then do something else?

• 12:17Speaker 01

  No, actually, this was the moment where I, you know, I kind of, I think that was the moment where I discovered nonprofit wasn't for me. It wasn't the mission of the work. The mission of the work is so important, and I find it to be worth getting out of bed four in the morning. But my personality was wholly unsuited for it.

• 12:36Guy Raz?

  Yeah.

• 12:37Speaker 01

  I think what irked me was the amount of delicacy and diplomacy that's really needed to push projects through in the nonprofit sector. It's a really admirable skill, and you need to have it to be successful in that world. And it was not something that I naturally had.

• 12:54Guy Raz?

  Yeah, I mean, it's interesting, because you are the child of a diplomat and had aspirations to work in refugee camps. But the combination of where you were in life and your sort of wanting to move quickly just wasn't the right fit at the time for that job.

• 13:11Speaker 01

  Yeah.

• 13:12Guy Raz?

  2011, you come back to the United States, and you go to New York and get a job at a private equity firm.

• 13:19Speaker 01

  Yes, yeah. So you can see how I ping pong in my career. You know, that was actually what a lot of my colleagues at Bain ended up doing. They were either going to business school, or they're going to private equity. And I had gotten rejected from business school. I was on the waitlist. I was just, I didn't really have a clear reason for why I wanted to go to business school. Maybe they saw through that, or maybe, you know, I just wasn't a good enough candidate. But either way, I was on the waitlist. And then they released, I think, the final candidates in August, and they said, no, thank you.

• 13:52Guy Raz?

  And just to pause for a second. I mean, today, obviously, this is, for a variety of reasons, a badge of honor. But back then, were you embarrassed by that?

• 13:59Speaker 01

  Oh, my gosh, totally. I mean, I- I don't even know if it's a badge of honor now. A lot of people are like, oh, you got a Harvard MBA, right? And I'm like, no, no, just, I just went to college. So, yeah, I didn't get in. I don't, yes, and now I think I'm more comfortable talking about it, but I wasn't for a really long time.

• 14:21Guy Raz?

  All right, so you go, you get a job with a private equity firm. It's called Starwood Capital. And this is going to be like the beginning of your, you know, the next phase of your career. I mean, you're still in your 20s at this point. And private equity is intense and you're looking for companies to invest in. And it must have been exciting. And you get to New York and what was it like?

• 14:44Speaker 01

  Well, I will start by saying it was, it was, this might be weird after saying that my dream was to work at nonprofit to say this was my other dream job, but it really was. I thought what they were doing was fascinating. And when I got the job, I took it. And I started, gosh, January of 2013. And I thought this was going to be my dream job.

• 15:04Guy Raz?

  So this is January of 2013?

• 15:05Speaker 01

  Oh, January 20, I'm sorry, January 2011.

• 15:08Guy Raz?

  Sorry, so January 2011, you get to New York and you were just there for four months, which seems, seems like something happened. It just seems unusual. What, what hap, why? Why were you there for such a short time? Why'd you leave?

• 15:23Speaker 01

  You know, I, I loved the job, but the short of it was that it was a terrible cultural fit for me. I was one of two female investment professionals, I think, out of dozens, if not hundreds. The company culture was hyper masculine, aggressive, swaggering, which all looks very cool on TV. And I'm sure there was a part of me that idolized it too. But the truth is, it was terrible for me. I was, I think I professionally performed just fine, but internally, I mean, I started hyperventilating at work. I developed a weird tic. It was just very clear, I think, from week one, I was like, oh, I made a mistake.

• 16:02Guy Raz?

  What was the breaking point? Because four months is, you know, it's a short time. And there must have been something that happened that you, you just said, I can't come back here anymore.

• 16:13Speaker 01

  The breaking point was me just like crying uncontrollably and calling my friend being like, "I don't want to go to work tomorrow." I just, I generally felt like a loser. I mean, here I was, I spent three years at Bain and I moved to South Africa thinking that's gonna, that's gonna be my thing. And then, you know, after a year I decide, okay, it's not for me, so let me, let me give this thing a try. And I'm, I'm there for four months. Like, the narrative I had written for myself was that I was a loser. And so, it was, it was really, it was just a devastating time for me.

• 16:45Guy Raz?

  When you told them you were leaving, were they shocked?

• 16:48Speaker 01

  I think my boss was surprised. I think private equity is filled with a bunch of people who are incredibly determined and want to climb the ladder. And here I was saying like, "I've been here four months and I'm out." And I remember the first thing he said to me was, "Don't you want to become vice president here?" And I was like, "That's honestly the last thing I want to do." And so, you, you start to have real moments of doubt about who you are as a person. And,

• 17:13Guy Raz?

  Yeah.

• 17:13Speaker 01

  Up until that point, you're always like, "Sarah who goes to college, you know, Sarah who works at Bain, Sarah who blah." So much of my personal identity was tied up in the job that I had. And so, to go from Sarah who works in private equity, who flies on private jets to Paris, to Sarah who doesn't have a job and is worried about how she's gonna pay her COBRA payment next month, that was a, that was a sucker.

• 17:38Guy Raz?

  So, at this point, you're like 27, 28 maybe?

• 17:42Speaker 01

  Yeah, 27, I think.

• 17:44Guy Raz?

  And you would rather leave without a plan than to stay?

• 17:47Speaker 01

  Yes. And I would say, "would" is a, that's a strong word. Like, I felt like I had no choice but to leave without a plan. I just needed to get out. So, I still remember that feeling when I like took the Metro North on my last day back into the city. You can see out in front, the rail way in front of you. And I just remember thinking, "Oh, my gosh, freedom. I'm, I'm free again." And so, yeah, I, I left without a plan. I like cried for a month. I had started seeing my psychiatrist about a few months into, a couple of months into that job because I was, you know, I was a nervous wreck.

• 18:22Guy Raz?

  Yeah.

• 18:23Speaker 01

  And so, I, you know, I was spending a lot of time actually in her office. I think I was probably going like two, maybe sometimes even three times a week, just to feel normal again.

• 18:32Guy Raz?

  Yeah.

• 18:32Speaker 01

  And that was around the time. I had always had this idea for starting A clothing company for working women.

• 18:40Guy Raz?

  Wait, you always had this idea?

• 18:43Speaker 01

  Yeah, well, I should say always, as in like when I was working management consulting, because I could never find good clothes. And so, actually, I remember at my HBS interview, they ask you, what do you want to do with your life? And so I said, I want to go work in refugee camps. And they were like, OK, well, if there's, if you had to go do something else, what would it be? And I said, well, you know, I really think someone should go start a workwear company for women, because clothing out there is just terrible. And I remember the interviewer laughed, and she was like, tell me more about that. I think a lot of women can relate to that. So I had always had that idea, I guess, since working at Bain and since needing those clothes myself, but...

• 19:17Guy Raz?

  This is this idea?

• 19:18Speaker 01

  Yeah, idea.

• 19:19Guy Raz?

  Like, we all have ideas, right?

• 19:20Speaker 01

  Exactly, exactly.

• 19:22Guy Raz?

  Somebody needs to make a better pickle, or I shouldn't say it.

• 19:25Speaker 01

  Correct.

• 19:26Guy Raz?

  Very great pickles, but whatever it is, we all have these things. And this was your thing. It was like, but it wasn't really a serious, like, you weren't sitting down at night and weekends, writing a business plan for a clothing company?

• 19:37Speaker 01

  No, I mean, I was just like, what, fashion? Like, I'm not even interested in fashion. I just, I was like, but however, I am a consumer of clothes.

• 19:46Guy Raz?

  Yeah.

• 19:46Speaker 01

  I have to wear clothes every day. I care about looking good and gaining the respect of my peers and my clients, so I'm going to put effort into it. But, God, it is so hard.

• 19:56Guy Raz?

  Yeah. But, so this is like, the spring of 2011. You quit your job, and now you've got time, which, sort of, like, one, if we're like watching one movie on this, you've got time, and then you get, you know, you're excited, and you think, now I can start this business. But there's another movie, which is, you're going to see therapists. I have to assume that you were experiencing some depression from, you know, leaving that job. That can be a hard time to get motivated, to feel like, right? Did you just take some time to just kind of be sad and depressed? Or were you thinking, I'm going to jump into this next idea?

• 20:36Speaker 01

  I remember being terribly sad and depressed and unwell. And I also remember thinking, I need to get moving, or else I'm going to get stuck.

• 20:48Speaker 01

  And so I only remember this because I remember the dates that I signed certain contracts. I signed for a WeWork office starting May 1, back when WeWork was still very small. I think they had like two buildings in New York. And then I officially registered as a LLC June 1 in Delaware. So I just, I have records of those contracts, which makes me think like, okay, there was a part of me that, that kept

• 21:14Guy Raz?

  Kept pushing.

• 21:15Speaker 01

  Pushing myself, yes. But then I also remember going on a run and stopping in the middle of the run because I had to like cry for 30 minutes. And I think that was mid-July, right? So it was, it was kind of a, it was a parallel process. It wasn't like, okay, now I'm done being sad and I'm gonna go start my company. It was, I was working through both things at the same time.

• 21:34Guy Raz?

  So as you started to, as the kind of the gears in your head started to turn more and more about this idea of professional clothing for women, did you have a sort of a solid vision of what that would be? Or was it still kind of abstract in the spring of 2011?

• 21:50Speaker 01

  You know, surprisingly, my, my vision for the product was very clear. My mom, before she started her jewelry business, had worked in high-end fashion. And so I think through her, I got to see and touch a lot of these beautiful pieces of high-end clothing that she would bring home, not because she bought them, but you know, as samples or as gifts. And I think she dressed also in that way incredibly tailored and polished. And I think my big question when I was starting this business was, why aren't there clothes like this for regular working women? You know, the clothes that I was shopping for at the time, it was always ill-fitting. It would rip a lot easily. I would always have to get it tailored. It just, it would wrinkle easily.

• 22:35Speaker 01

  I mean, there were so many things that were wrong with it and I was spending so much money trying to dress professionally for work. So I knew exactly the kind of clothing that I wanted to create, which is really like, I wanted to sell dresses that would sell for $2,000 for a fraction of the price. And I wanted to work with a luxury designer because I wanted my customers, I wanted regular working women to wear luxury quality clothing.

• 22:57Guy Raz?

  So you, so you register an LLC and I mean, what, like if I said to somebody, all right, let's go start a clothing company. Like I would have no idea what to do. Okay, I register the LLC and then, and then what? First of all, You need money, right? So, how much money did you have at the time to start this thing?

• 23:16Speaker 01

  Very little. I had about $35,000 saved up, which is not very little, but you know, in the context of starting a business, it does not get you very far.

• 23:25Guy Raz?

  Right. But you had saved this money over the course of your time at Bain and this private equity firm?

• 23:30Speaker 01

  My entire life, yeah. It was like the piggy bank that I had kept.

• 23:34Guy Raz?

  Yeah. And what like, what's $35,000 going to, gonna do? I mean, it's gonna last?

• 23:41Speaker 01

  Yeah, it doesn't, it doesn't go very far, which was the short story. My parents also lent me $35,000, so they said, okay.

• 23:47Guy Raz?

  So you got $70,000?

• 23:48Speaker 01

  Yep, so I started with $70,000.

• 23:50Guy Raz?

  And by the way, the idea was to see how far you could go and then eventually fundraise? Or did you think, I'm gonna go for fundraising right away?

• 24:00Speaker 01

  Yeah, it was, it was, I mean, I didn't, I couldn't even think about fundraising. Like, I knew through The Grapevine, you know, the Bonobos founders, Warby Parker founders, both worked at Bain. And so I think, I mean, in some ways, they served as great role models. You, you, you kind of saw from afar that maybe it was possible to fundraise. And so I think in those initial days, it really, it wasn't like, this is the business plan, let's go raise some money, let's go start this business. It was like, does anyone know anything about making clothes? Because if you do, I'd like to talk to you.

• 24:30Guy Raz?

  Yeah, I mean, when, you know, we've had conversations with founders who, at this point, the first thing they do is start to reach out to anybody who will talk to them. They, you know, they'll send like cold emails and cold call people for advice. And is that, is that who you, who you are? Like, is that your personality? Is that what you did?

• 24:50Speaker 01

  I would say it was more organic. Again, I didn't know anybody who worked in fashion. So I remembered that there was a woman who was a couple of years ahead of me at college. She had gone to RISD to study interior design and I think textiles in interior design. And I was like, well, that's, that's one step closer to fashion. So I reached out to her and I was like, hey, do you know anybody who works in fashion? And she was like, actually, I do know one person from RISD who went into fashion, so let me put you in touch with her. So she was the one fashion designer that I I knew, and she put me in touch with her five headhunters in fashion, most of whom had no time for me. You know, they were like, what, Bain? Like, never heard of it, don't care. Like, please come back when you're serious. I've got Calvin Klein on the other line.

• 25:34Guy Raz?

  Yeah.

• 25:34Speaker 01

  But one of those five headhunters decided to take a chance on me. He, you know, said, let me see if I can help you out.

• 25:41Guy Raz?

  Help you out with what?

• 25:43Speaker 01

  Recruiting, recruiting.

• 25:44Guy Raz?

  So, oh, so this headhunter said, let me see if I can help you find somebody to join you.

• 25:49Speaker 01

  Find somebody as a co-founder.

• 25:50Guy Raz?

  Because you could not, you felt like you couldn't do this by yourself. You didn't have the understanding or the knowledge of the industry.

• 25:56Speaker 01

  Yeah, that's right. And I think it's not only that I couldn't do it, I didn't want to do it. You know, I wanted to design the most beautiful dresses in the world. And I have not trained as a designer.

• 26:07Guy Raz?

  Yeah.

• 26:07Speaker 01

  And so it was really important to me that I had a high-end fashion designer. I had other designers who said, you know, why don't you just, you can do it yourself. Like, you can just copy these designs, you know, add a sleeve, you know, add whatever and sell it. And I was like, no, no, that's, that is not what I want to do. I don't, I don't want to create more of what is already out there. I want to fundamentally actually create something different.

• 26:29Guy Raz?

  So there's this guy, he's a headhunter, and he agrees to kind of help you out. And he identifies somebody who's a fashion designer, you know, who you should meet. Her name is Miyako Nakamura. Who was she? What was she doing at the time?

• 26:44Speaker 01

  Miyako, at the time, I think, had just left Zac Posen. She was their head designer. She was known in the fashion industry. And, you know, she, we were just in totally different worlds. I think that was actually my other kind of surprising moment. You know, I thought I understood what New York was about. But it was one of those moments where I was like, wow, I literally don't know anybody in the fashion world. And yet, like, the capital of fashion is New York City. The garment district is in New York City. And, and our circles did not overlap at all.

• 27:12Guy Raz?

  So, so you meet Miyako, and what's your pitch to her? Like, you say, hey, I'm, I'm starting this company. I want to make really beautiful, you know, clothing for professional women that is, you know, relatively affordable. Was that how you described it to her?

• 27:29Speaker 01

  Yeah, basically. She was like, what? You know, she, the way she described it to me, she says, I thought everything in the world that needed to be designed had already been designed. And I think she herself, at that time, was going through a kind of career crisis where She didn't really understand the point of design anymore because she thought it's all, it's all already been done. Like, why bother?

• 27:52Guy Raz?

  So this is what I'm curious about. You meet Miyako. She had been the lead fashion designer for Zac Posen, a major fashion brand, you know, designer brand. You've got $70,000 in seed money between you and the loan you took. You have zero experience. Obviously, you're intelligent, but no experience in fashion. You've got this kind of harebrained idea to start a company. And that's pretty much in a WeWork hot desk. Like, why? Why would she say, "Yeah, sure, I'll go work with you"? I'm just, yeah, why would she agree to do this?

• 28:29Speaker 01

  Well, I'm just irresistible in person. No, I'm totally joking. Every investor that I've ever spoken to, I mean, frankly, like, anybody I have ever spoken to about this in any sort of detail, their follow-up question is usually, like, "What was she thinking? And why would she come and work for you?" Totally fair question. You know, I don't want to answer for her, but I think for her, it was, it just, it was so different. It was so unlike anything else that had ever been proposed to her. This idea of designing for a group of women that she didn't even really know about, working women. This idea that, she always says, "I never actually seen my clothes on a real person." That means a non-model. "I've never actually seen my clothes on the street." You know, she designed

• 29:14Speaker 01

  Oscar gowns. I think she designed a gown once for Natalie Portman. You know, that was kind of the world she was moving in. But she said, "There was no practical element to the beautiful designs that I was making." And I think that was, that was a big question mark for her.

• 29:29Guy Raz?

  I mean, that, I understand, the creative side of it, right? But you couldn't even offer her, like, a steady income. You know, you could offer her a partnership, but like, she was gonna be, she was not gonna have an income for who knows how long.

• 29:43Speaker 01

  Yeah, I mean, I think... I mean, all of your questions are fair. I'm sure this could have played out very differently. I think the only way to describe it is that we had some sort of connection. You know, I was actually going to go with a different designer. I had met someone else who had been the head designer of another very famous brand. And I actually wasn't even going to meet Miyako. I told the headhunter, you know, I really like this other person. Like, she feels like the right person. Like, you know, I don't really even care to meet with another candidate. And he was like, no, no, just meet with her because I think you guys are going to really hit it off. And even when we first met, and I, you know, I was telling her about the kind of women I wanted her to design for, I said, you know, don't you know those women? They, they walk to work in their flats and they have their heels in their bag.

• 30:27Speaker 01

  And once they get into the elevator, they change out into their heels. And she was like, no, I've never met anyone like that. And I was like, wait, what world do you operate in? She was like, everyone I know walks to work in heels and stays in their heels all day. But at that point, like, I didn't even know what was involved in designing clothing. I share this story just to level set just how elementary my understanding of clothing manufacturing was. I remember Miyako, early on, said to me, we're going to need to find a pattern maker. And I was like, oh, no, no, don't worry. We're not going to do any prints. We're only going to do solid colors.

• 31:04Speaker 01

  She started laughing in my face because a pattern maker, to the uninitiated in fashion manufacturing, is like the architect of the dress.

• 31:13Guy Raz?

  Yeah, the person who cuts out the shapes.

• 31:14Speaker 01

  Exactly, exactly. The person who designs on a white piece of paper how the different pieces of fabric are supposed to be laid out and cut. And I thought pattern, she meant like floral patterns or checkered patterns.

• 31:26Guy Raz?

  Or plaid.

• 31:26Speaker 01

  Yeah, exactly. I thought that's what a pattern maker was. So I was like, don't worry, we're just going to do like navy dresses. And so that is, that is how much I didn't know.

• 31:41Guy Raz?

  When we come back, how Sarah got a crash course in dressmaking, how she tried and failed to raise money, and how she and Miyako discovered what it means to have a bank account with a minus sign. Stay with us. I'm Guy Raz, and you're listening to How I Built This from NPR.

• 32:05Guy Raz?

  Hey, welcome back to How I Built This. I'm Guy Raz. So it's 2011, and Sarah's teamed up with a well-known designer named Miyako Nakamura. And they begin to imagine what a new line of clothing for professional women could look like.

• 32:20Speaker 01

  I'm embarrassed to say that I once bought 20 somewhat odd thousand dollars of clothing from a luxury department store, which really only amounted to like seven pieces because each one was so expensive, because I wanted to show Miyako the kind of clothes that I wanted her to design. And by the way, I did return it.

• 32:39Guy Raz?

  You returned them, yes?

• 32:40Speaker 01

  Yes, I did. But I was the scariest 24 hours of my life were the 24 hours where I had those seven dresses in my possession in my apartment. I was like, what if we have a fire? But I, you know, we, and then I just started showing her. I was like, you know, this style, it's so beautiful. It would actually be perfect for work. But it cost $25,000.

• 32:59Guy Raz?

  And describe the style, like clean lines, dark blacks, grays? Like, what did they look like?

• 33:06Speaker 01

  It was tailored, and I think most importantly, the fit was good. And when I say the fit was good, so I have since learned a lot about pattern making and fitting clothing. Most brands, if you're lucky, the designer will fit the garment on a real fit model once before it goes into production. If the fit on something you buy is off, it's probably because it wasn't fitted correctly, or it went into production before all of the errors were corrected. Luxury brands can afford to do three or four fittings to really perfect the fit. Whereas lower-priced brands, they might be fitting it once, or maybe never. They might just

• 33:47Speaker 01

  go straight to production. And, I mean, there are so many things that are involved in good fit, but that was really one thing that I wanted her to understand is the way your body feels when you're wearing a well-fitted garment, it's magical. And you just can't get that at most of the price points that are out there.

• 34:06Guy Raz?

  And who did you tell her to imagine she was designing for? Like, what?

• 34:08Speaker 01

  Oh, me.

• 34:10Guy Raz?

  And what was the job? Was a woman working, doing what?

• 34:14Speaker 01

  You know, we had always three tests. One was called the taxi test. So if you're climbing into a taxi, can you jump in without ripping your scheme?

• 34:23Guy Raz?

  Right.

• 34:23Speaker 01

  The other one was the bend over test, which is if you bend over, can the person sitting opposite from you see your cleavage or your bra?

• 34:32Guy Raz?

  Right.

• 34:33Speaker 01

  Because that's strike two. And then strike three was can you see underwear lines? Every morning while I was working at Bain or Private Equity, I would always turn around and check the mirror to make sure that my underwear lines weren't actually showing through whatever I was wearing. And those were the three tests. And so with every garment that we were making, I said, I just want you to make sure that those three bases are covered. And so I would just move around in every single garment that she made to make sure that it met those things.

• 35:01Guy Raz?

  And I guess this is a good place to kind of talk about confidence in a work environment, right? I mean, it sounds like you were looking to design something that would make women feel more confident in the workplace. Is that more or less right?

• 35:17Speaker 01

  Yeah, that's, I mean, you put it perfectly. I just didn't want women to have to worry. Working women have to worry enough

• 35:24Guy Raz?

  Yeah.

• 35:25Speaker 01

  about whatever it is that they're doing. The last thing I want them to worry about is the clothes that they're wearing. And I'm sure men can relate to this, too. When you leave home that morning and you're not quite confident in whatever it is you're wearing, like maybe your sweater has a hole in it, or maybe your pants are a little bit dirty, or maybe they're just not quite fitting, right? And it's always in the back of your mind a little bit. And I just wanted to do away with all that.

• 35:53Guy Raz?

  So once you had sort of the first prototypes or agreed upon designs, how did you get them made? Where did you get them made?

• 36:02Speaker 01

  In the garment district of Manhattan.

• 36:05Guy Raz?

  Right.

• 36:06Speaker 01

  I didn't realize the extent to which manufacturing is still very much alive in New York. And, you know, just when I was working at Bain, I was working right in Times Square. And I couldn't believe that, you know, these factories were literally two blocks, three blocks south of me. And you open the elevators and it is just rows and rows of sewing machines. And I just didn't even know this industry existed. But that is where we made our first run of dresses. And I make it sound easy, but it wasn't at all. Most factories are not willing to work with a no name because, I mean, small designers come and go. And so I didn't realize, like, I was like, well, I'm willing to pay you money. And they were like, it doesn't matter if you're willing to pay us money. Like, we need sustainable businesses.

• 36:48Speaker 01

  So if you're not going to be around in a year, which was true of most fashion brands, then we don't want to start this partnership. And so, you know, we had to beg our first factory to make the dresses for us. And at this stage, they were just samples. We weren't even doing factory runs. But I think Miyako's experience was everything. So they trusted us because Miyako was doing it, you know, and I was just the woman who signed the checks.

• 37:14Guy Raz?

  And so you got a factory to agree to make you just a few samples of each item?

• 37:19Speaker 01

  Yeah, that's right. So, you know, the other thing that's scaring retail businesses is inventory. And because we only had $70,000, I didn't want to tie up my cash in inventory. And so we decided that we would do trunk shows. And we would bring samples and we would bring one of every size and we would have people try them on. And based on that, we would place orders.

• 37:39Guy Raz?

  Right. And a trunk show is literally like bringing a trunk and going to someone's apartment or some small space and hopefully people will show up, inviting people to come.

• 37:49Speaker 01

  That is correct. I think we did, gosh, a dozen or so in the first year. And it was hard work. You know, you're lugging around suitcases. I was lugging around fabric, rolls of fabric on my shoulder through the garment district. It's a very physically intensive experience.

• 38:07Guy Raz?

  And who did you invite to the trunk shows? How did you even get people to show up?

• 38:11Speaker 01

  Friends and former colleagues.

• 38:13Guy Raz?

  Coming to where?

• 38:14Speaker 01

  We rented this hotel suite. We turned the bathroom into a dressing room, the shower stall into a dressing room. I think we created one more makeshift one. And the first two trunk shows, I think legitimately, it was really just my friends and friends of friends coming to be supportive. But I think by the third trunk show, I hardly knew anybody there. And what started happening was women would be telling each other at the workplace. We had zero money to spend on marketing. So it wasn't like we were inviting editors or taking out ads or any of that. It was women just telling other women. Remember, there was a group of women from Goldman at our third trunk show. And I was like, how did you hear about us? And they were like, oh, well, Jenny saw so and so wearing this dress. And she asked her where she got it. And here we are.

• 38:59Speaker 01

  And most products that people make, you rely on editors, magazines, ads to spread the word. It's essential for your business. And I think one thing I didn't quite realize, women, they're not looking to fashion magazines to tell them what to where to work. They're turning to each other. They're asking each other, where'd you get that? Where'd you shop for that? And so that was hugely beneficial in the early days.

• 39:23Guy Raz?

  And so you and Miyako would just be at these trunk shows describing the clothing? Or was it just you?

• 39:29Speaker 01

  Yeah, no. So it was me, my other co-founder, Nuri, who is someone I worked with at Bain.

• 39:36Guy Raz?

  You brought her on because you needed somebody with a different skill set?

• 39:41Speaker 01

  No, it was actually the opposite of Miyako. I needed someone who could do what I was doing because at that point, I was getting stretched too thin. I should also share probably at that point, I wasn't taking a salary. I was tutoring to make ends meet. So usually every day from, I would wake up and then I would work. I would be running around the factory, the pattern maker, the factory, the pattern maker. And then from 4:00 to 7:00 p.m., my apartment would turn into a tutoring facility. And I would be teaching the SATs or 5th grade math or 7th grade English.

• 40:15Guy Raz?

  Wow.

• 40:15Speaker 01

  And then I would start working on my business again in the evening. I mean, I just had no time to attend to everything that I needed to. And Nuri was someone who I worked with. She was actually the first person I managed at Bain. And so I said, I want to take this company to the next level. Do you want to come? And she said, sure. And she... She also didn't have a salary. I couldn't pay her salary, so she started tutoring, too. And that's how the two of us made ends meet.

• 40:42Guy Raz?

  All right. So in 2012, you're doing trunk shows and you're getting some people to show up. But I mean, you can't sustain a business doing trunk shows, right? And I have to imagine that you guys were not making any money in that first year.

• 40:59Speaker 01

  You know, I think it was after we did our first set of trunk shows. And by the way, we sold out. I mean, that was, we had made about $50,000 at that point. And we said, okay, this is a quote unquote, "proof of concept." We're gonna go raise money now.

• 41:12Guy Raz?

  So already in 2012, that's where you said, all right, now is time to go out and raise money.

• 41:17Speaker 01

  Yeah, that's right. I was like, you know what? Not only do we have product, we have made money now. So this raising money thing, it's gonna be a piece of cake.

• 41:26Guy Raz?

  I mean, you hadn't really made money because your money was, you had expenses and you had to pay for the fabric.

• 41:31Speaker 01

  Yeah, we had generated revenue. You know, I think it was in the fundraising world, they talk about pre-revenue companies and post-revenue companies. And so I was like, well, we are a post-revenue company. And, okay, we said, you know, I don't know, do we want to raise a million dollars, $2 million?

• 41:48Guy Raz?

  And so who did you, who did you reach out to?

• 41:51Speaker 01

  We started with friends and family. This is a trick that I pass on to other entrepreneurs who are trying to raise money in the very early stages. Because a lot of people, I think women especially, tell me they feel bad about asking for money. They feel nervous, what if I lose their money, et cetera, et cetera. And what I tell them is, rich people get asked for money all the time.

• 42:11Guy Raz?

  Yeah.

• 42:12Speaker 01

  It's you and 500 other people asking for their money. And one phrase that I developed, which I started using in all my emails, is, "If you or anyone you know might be interested, please let me know." I think the "you or anyone else you know" gave the other person an elegant out if they weren't interested. You know, they could say like, yes, I'll think about who I know. Or if they're interested, they'll say like, actually, I'm interested. Or they really might connect you with someone else.

• 42:39Guy Raz?

  Were you able to raise any money in that, in 2012?

• 42:43Speaker 01

  I raised, so contrary to, you know, what we thought we wanted to do, which was like, I don't know, $1 million, $2 million? We raised $400,000 and it took me nine months.

• 42:55Guy Raz?

  So then, what, you continue to do these trunk shows? Because that's not gonna, right, that's not gonna cut it. You're talking about other companies like Bonobos and Warby Parker and...

• 43:05Guy Raz?

  These are e-commerce companies, right? They've got websites where people can order stuff, so.

• 43:11Speaker 01

  Yeah, that's right. And around this time, this direct-to-consumer was becoming a thing. And so online was where it was at. And I think I foolishly had this notion that if you launch a website, your customers come and they shop and you become millionaires.

• 43:24Guy Raz?

  Yeah.

• 43:25Speaker 01

  Of course, I think we have all learned since then that that is not the case. But at the time, there was such a media frenzy around these new DTC businesses. And I just thought, like, wow, it's so easy. Like, let's launch a site. And so we did. Can never forget this, 3:00 AM of January 1, 2013. That was the official launch of our e-commerce site, mmmlafleur.com.

• 43:48Guy Raz?

  And the name MM, I mean, obviously, Lafleur is your last name. Where did that come from?

• 43:53Speaker 01

  Oh, it's my mom's nickname. Her nickname is Meme, which is a child's way of saying eyes in Japanese. And she has really big eyes, and so that was her nickname. And initially, actually, it was called Meme Lafleur. But Meme in French means nana. So after a while, I realized, like, nana flower doesn't actually have the best ring to it. Like, maybe we should change that. And so we took the initials of Meme, which is MM, and made it Mmmlafleur.

• 44:19Guy Raz?

  All right, so 2013, you launched the e-commerce site. And it was the same kind of model? People would order something and then you would have it made in the factory?

• 44:28Speaker 01

  No. At that point, we did decide to hold inventory.

• 44:31Guy Raz?

  How many did you have made?

• 44:32Speaker 01

  Let's see. We probably did a run of 50 for each, because I think that was the minimum. So we probably have 350 dresses.

• 44:38Guy Raz?

  So 350 dresses.

• 44:39Speaker 01

  All sitting in my apartment.

• 44:40Guy Raz?

  All sitting in your apartment. You put up the website, sit back, you're like, waiting for the orders to come in, and?

• 44:46Speaker 01

  And crickets. Crickets is the short of it.

• 44:51Guy Raz?

  Like, no one is clicking on the website and?

• 44:55Speaker 01

  Like, I don't know. Maybe we get like 10, 15 orders on the day of launch. And then afterwards, we get like three. Two, I'm sure there were days with zero. I mean, it was painful.

• 45:08Guy Raz?

  And those three or two, it might be $200 or $400.

• 45:12Speaker 01

  Correct.

• 45:12Guy Raz?

  And you thought, just putting up a website, people would find you.

• 45:16Speaker 01

  Yes, that was my very naive assumption.

• 45:20Guy Raz?

  And presumably, you didn't have money to do a lot of marketing.

• 45:24Speaker 01

  No, I mean, yes, we, it was really, still continued to do trunk shows. We had revenue goals for the month, and so if we weren't meeting our revenue goals, then we would, you know, set up a trunk show, stat, and try to make some money off of that. And the trunk shows, actually, were always quite lucrative. You know, we knew that when our customers actually tried on the clothes in person, they loved them. So often, women were buying multiple dresses. But online, it was just a totally different story. We could not sell our dresses.

• 45:55Guy Raz?

  So I read that in that first year, 2013, you did $300,000 in sales, which on one level, sounds really impressive, but on another level, for an apparel business where the costs and expenses are high, I mean, that's not, that's not a whole, was that, did you meet your goal, your targets?

• 46:12Speaker 01

  No, we did not. I think, actually, that for the first year, my goal was like a million. So we felt quite short of that. And in 2013, we had hired three other people.

• 46:23Guy Raz?

  And presumably, you couldn't pay them a whole lot.

• 46:26Speaker 01

  No, you know, we were paying ourselves very, very little. And we've only raised $400,000 at that point. So, you know, we're watching the cash dwindle.

• 46:36Guy Raz?

  All right, so that first year, you're doing a third of what you were hoping to do. You get into 2014, and I have to assume your cash reserves are getting close to running out.

• 46:47Speaker 01

  Not only did we run out, it actually went into the negatives. Our bank account, I think, at one point, said like negative 2,000 or something. And I didn't know you could draw down beyond zero. So that was a wake-up call. And I had to go out and fundraise again.

• 47:02Guy Raz?

  Same people, same seed folks?

• 47:04Speaker 01

  No, no, no. I knew I couldn't go back to them because we haven't done what we said we wanted to do on the cash that we had raised at that point. So I had to go out and fundraise again. And the most amazing part of this story is

• 47:21Speaker 01

  Meeting Bob.

• 47:21Guy Raz?

  And who's Bob?

• 47:23Speaker 01

  Bob Deutsch. Bob was a CFO at these two insurance companies. I had gone to meet my husband's friend's father, who was a very successful entrepreneur, for some advice. Secretly, I'm also hoping maybe he'll invest. But he said, you know, you've got to meet with my former CFO, Bob. Bob and I have started two companies together. They sold both incredibly successful. And I go and meet Bob and I say, hey, Bob, I'm just having a really hard time trying to raise money. Can you please give me some guidance? And he said, well, you know, the first thing we should think about is, how much should your company be valued at? And how much do you want to give up? And I was like, I'm willing to have my company valued at anything just to keep the business going.

• 48:08Guy Raz?

  Yeah, right. Just keep it afloat. Yeah.

• 48:09Speaker 01

  Exactly. And he's like, no, no, like, step one, let's go do this. And so he essentially gives me a homework assignment.

• 48:15Guy Raz?

  A homework assignment to help you figure out what you think the company's worth?

• 48:18Speaker 01

  Yep. And how much I should be raising. And I go back to Bob and he says, this is really interesting. Like, these are the facts that you need to go out with when you go and talk to these VCs. None of the VC conversations actually go anywhere. But armed with this information, I'm able to say, my company, we've already generated revenue. Similar companies, when they were at my size, were raising this amount of money at this valuation. Can we talk?

• 48:46Guy Raz?

  So what did you value the company at at the time?

• 48:48Speaker 01

  Oh, gosh, it was 6 million, maybe?

• 48:51Guy Raz?

  When you are out of money and you've got to raise money and Bob is helping you kind of develop a pitch and you went to VCs, and what was their response when you pitched them on this company?

• 49:07Speaker 01

  Their response was the same response that I would basically hear for the next three to four years, which is, congratulations. It looks like you started a real great niche business for yourself.

• 49:18Guy Raz?

  But we're not interested, was basically, yeah.

• 49:20Speaker 01

  Oh, yes. Yeah. Niche business is essentially, it's code word for... This is small potatoes. And I'm thinking to myself, like, what about working women is such a niche business? There are 30 million women aged 25 to 45 who work in some sort of corporate environment. And these women spend, on average, for women making 75K and up, $4,000 a year on clothes to wear to work. And so that's roughly a $100 to $120 billion market. To me, nothing about that was niche.

• 49:50Guy Raz?

  But were you, I mean, were you mostly pitching to men?

• 49:54Speaker 01

  Yes, yes.

• 49:55Guy Raz?

  And not to, I don't want to pile on you, but I have to assume they didn't quite, you know, they were not going to be able to relate to this. This is, maybe they didn't fully understand the opportunity?

• 50:04Speaker 01

  Yeah, there was a lot of that. I'm sure you've heard this from your other founders, but there was a lot of, oh, I'm going to have my wife, who is a stay-at-home mom, try it. Nothing against her, but she's been at home for 30 years and probably has different needs for what she wants to wear every single day. Or, you know, I'll have my 17-year-old daughter try it. Just kind of lumping in all women into the same category. The most honest thing I heard was, I had an investor call me after we did the pitch, and he said to me, we really like you, we really think there's a lot to like about the business, but it's just so early, and we're four guys sitting around the room, and we just can't get a gut feel on the product.

• 50:47Speaker 01

  I've repeated that elsewhere, and people are like, oh, my God, I can't believe he said that, how sexist. But to me, it was a relief. That was the first time where someone said to me, like, it's actually not you, it's us not being able to understand the product. But then, I think, the part that I didn't share was that Bob, after seeing me go through a couple of these VC meetings, I think he's seeing how determined I am to raise this money, he says, you know what, I'm willing to write a check. Which I honestly, at that point, wasn't expecting, because he's more coaching me through this process. And he was like, you know, I'm willing to invest 50, maybe $100,000, which is a lot of money for us at that time.

• 51:31Speaker 01

  And he says to me, and are you interested in raising maybe a little bit more money from me and my friends? And I said, you know, absolutely. And he says, OK, give me 24 hours. And so 24 hours later, Bob calls me and he says, "Okay, Sarah, I've put together $400,000 for you."

• 51:49Guy Raz?

  Wow.

• 51:50Speaker 01

  That is the quickest any single investor has put together around like that for me. And I think Bob has these very close connections with other business people, well-established business people, and they do deals together all the time. I think they pass each other deals and they move together, they talk to each other, they invest together. And I just never saw that with any of my other female angel investors.

• 52:20Guy Raz?

  Here's a question now, right?

• 52:22Speaker 01

  Yeah.

• 52:22Guy Raz?

  Because I think a lot of people who start businesses, this is a challenge, right? You've got to balance your independence and your vision and what you, you know, the ownership you want to retain, but you needed money.

• 52:34Speaker 01

  Yes.

• 52:35Guy Raz?

  So I have to assume at this point, you were willing to pretty much give up what you need to give up to keep the business afloat.

• 52:42Speaker 01

  Yes, it's so true. And I think you're actually, you're pointing to something really important there. And I catch myself doing this too now, and I really try to stop myself from doing it, which is telling other entrepreneurs, like, "Don't just take anyone's money," or "Be really careful who you take money from." That's all well and good when you've got cash in the bank.

• 53:01Guy Raz?

  Yeah.

• 53:02Speaker 01

  When you don't, it's really unhelpful advice because it's true, you really want to make sure who you take money from, but you also just want to keep your company alive.

• 53:11Guy Raz?

  So you had, you were in that position in 2014, which means that, you know, you had to be willing to give up, you know, quite a bit of your, of this company that you started.

• 53:22Speaker 01

  Yeah, that's right. You know, I think that's where, I mean, meeting Bob, and he ended up being a phenomenal partner. But Bob could have also been someone terrible. He could have really screwed me over.

• 53:31Guy Raz?

  Yeah, because everyone's seen Shark Tank where they're like, "I'll give you $25,000 for 70% of the company."

• 53:38Speaker 01

  I, you know, I was just like, I can't watch that show anymore because every time I'm like, "Walk away, walk away." But, um, yeah, $75,000 when you've got negative $2,000 in the bank is pretty precious.

• 53:50Guy Raz?

  It's a lot. Yeah, it's, all right. So you get this money. 2014, you're saved from extinction. But meantime, you've got a website and no one's going to it. And you've got inventory piling up, which is not a good place to be in because at some point, designs are going to change, your tastes are going to change, and you're going to end up shredding all that stuff.

• 54:10Speaker 01

  Yes. You know, we had moved into a really humble office in the garment district on 35th Street. It was above a methadone clinic. And I would just walk into this tiny room and I would see it flowing to the ceiling in inventory. And I would think to myself, oh, my God, we are going to die under a mountain of dresses. And I think that was the point where I was like, I saw the dresses and I said, what if we just sent our existing customers an email asking them if we could send them a box of dresses? Because we somehow have to physically move these dresses out of here. And so we sent our, I think we had like 1,000 customers on our mailing list at that time. And we said, we'll send you a box of products that we think you'll like. And if you like them, you can keep them.

• 54:54Speaker 01

  If you don't, you can return them. And so that was the pitch.

• 54:57Guy Raz?

  So this was more like now, like, we're going to send you a box of stuff and what you want, you keep and you pay for, and what you don't want, you return to us.

• 55:05Speaker 01

  Yeah. And 18% of customers responded to that email saying, sure, send me something. I don't have time. It would be so great if you chose it for me. And we ended up sending those 180 boxes out and making more money in that one week than we ever had in any month leading up to it.

• 55:26Guy Raz?

  I mean, that model was starting to be out there, right? There was literally a company called Trunk Club and Stitch Fix and some of these companies that we know. And you guys were not doing that? You weren't picking outfits for people, sending them and letting them pick and then send stuff back?

• 55:41Speaker 01

  No, we were not. I think we... We just thought, it was actually, it was interesting because even when I suggested this initially to my team, there were a lot of, when I say a lot of people, there were four people who said, like, oh, no, I would never want someone else to pick out what it is that I should wear. Like, I want to choose for myself. Why would I want someone else to pick for me? And, you know, I kind of had to say, Annie, Annie was my CMO. Annie and I were in the camp of, you know, we're not fashion lovers. Like, if someone else who understands fashion better than we do told us what we should be wearing, like, that's actually a pretty amazing service. So, we launched this, I guess you could call

• 56:24Speaker 01

  it a beta, in February. And operationally, it was a total nightmare. I mean, we sent the wrong size to people. Some people were like, why did you send this to me? I don't understand. There were a lot of those things. But the numbers really spoke for themselves. There was more demand for that service than we had ever seen.

• 56:44Guy Raz?

  I'm trying to figure, I mean, how did you even know what to send to people?

• 56:48Speaker 01

  For a good number of those 1,000 customers, we had met them through trunk shows. And so they had already purchased something with us.

• 56:53Guy Raz?

  Right. So, you had some data about them.

• 56:55Speaker 01

  We had some data about what they had picked, and we knew their size. And then, actually, that was a really brilliant moment by Annie, who said, you know, I wonder if we should try this with new customers. And so, she said, you know, why don't we email a group of people who've never shopped with us before and ask them to fill out some basic information about themselves? And based on that, why don't we tell them we're going to send a box of dresses to you?

• 57:17Guy Raz?

  And you called them bento boxes, right?

• 57:19Speaker 01

  Yeah, we did. We didn't call them bentos back then. But when we launched it in its official form later that year in the fall, we called them bentos.

• 57:27Guy Raz?

  And that really actually started to move the needle, right? Like, you actually started to see real revenue coming in that seemed to point in the right direction.

• 57:38Speaker 01

  Yeah, that was a moment that Silicon Valley calls finding your product market fit. We launched it in its official form, October 2014. We suddenly went from not being able to pay rent to tripling our revenue, you know, oftentimes, month over month.

• 57:54Guy Raz?

  And by the end of that year, 2014, did you, do you remember what your revenue was?

• 58:00Speaker 01

  Yeah, it was 8 million. But we had made more than half of that in the last 12 weeks of the year.

• 58:06Guy Raz?

  Wow. So, I mean, obviously...

• 58:10Guy Raz?

  That model, right, like the choosing and sending people clothing was working. But it still doesn't explain to me why it would just like explode in the last 12 weeks of the year.

• 58:22Speaker 01

  Yeah, I mean, I think when you walk into a clothing store, price is maybe one of 10 things that you're considering when you decide you want to buy that thing. Do you like the feel? Do you like how it fits on you? Do you like how the salesperson is selling it to you? Whereas when you're shopping online, first of all, it's really hard to tell what products actually look like. And when you see this like really simple black dress, it's not going to jump out at you. And you're thinking like, am I really going to spend $195 on a pair of black pants? And I think what Bento did in many ways is it took that decision paralysis away because we were getting our products into our customers' hands.

• 59:03Speaker 01

  And only once they tried it on were they really understanding why these pants cost $195. And then they start to say, oh, OK, I get it. I get why this costs $250. I get why it's worth it. But it is really hard to make that case online in e-commerce. And I think things have changed a lot since then. People are buying $2,000 Peloton bikes online. So I think that that sentiment has shifted a lot. But back in 2014, it was a really tough sell.

• 59:33Guy Raz?

  So I want to touch on a slightly sensitive topic, which is cost, right?

• 59:39Speaker 01

  Yeah.

• 59:40Guy Raz?

  Some people might look at your clothing and say, you know, I get it, it's not designer, it's not Chanel, but still, you know,

• 59:46Speaker 01

  Sure.

• 59:47Guy Raz?

  $240 for a dress or $225 for a pair of trousers. What am I getting out of this that I can't get from Zara or H and M?

• 59:59Speaker 01

  Yeah, we hear that all the time. And we were actually briefly, briefly talking to a department store, a luxury department store, and they said to us, you could sell these dresses for $700. That's what we would sell it for. And we said, exactly, but the point is we sell it for 200, 250. That's the point. But it's little details that I think most fashion designers wouldn't care about. And I think that's really, that's really where we set ourselves apart and try to justify the price point. Does it have pockets? Can you zip it up yourself easily? We're always checking to make sure that you can zip up yourself because you might be traveling by yourself and be in a hotel room by yourself. You know, does it, does it feel comfortable on the skin because you're going to be spending

• 1:00:43Speaker 01

  14 hours in it? It's my incredibly practical nature, wanting machine washability and wrinkle resistance and comfort in everything that I wear. And then Miyako really saying, I've spent 20 years training to deliver the best designs in the world, so let me figure out how I can do that for, for working women. And I think the place where those two things meet, that's Amelie Flair.

• 1:01:08Guy Raz?

  All right. So as you really started to, to see traction, presumably your, your biggest market was in New York and then, and then where, where were you also, like, what other markets were you seeing traction in, you know, by 2014, 2015?

• 1:01:24Speaker 01

  New York was always number one, still is number one. But we saw ourselves growing in two other markets, which was DC.

• 1:01:30Guy Raz?

  Right.

• 1:01:31Speaker 01

  And then the other one being San Francisco. And DC was fascinating. You know, we have a lot of Congresswomen, a couple of senators who wear our clothes and staffers too. You know, I was on Capitol Hill a few months ago and walked into the congressional building and immediately saw a number of our customers.

• 1:01:50Guy Raz?

  Wow.

• 1:01:51Speaker 01

  And then on the other end, we were seeing customers in San Francisco, which became our, our third largest market. And these women were saying to us, you know, I don't actually want to go to work in jeans and a hoodie. I make money. I want to wear nice clothes. And at the same time, if I dress too nicely, people think I'm interviewing.

• 1:02:06Guy Raz?

  Yeah.

• 1:02:07Speaker 01

  And in some ways, the dress code is even more nebulous. Can you help me figure out what to wear? And so Miyako actually started working on what we're calling Power Casual, a Power Casual line for them, where it's, it's much more relaxed. It's a lot of pant based, knit based offerings, but it's a, a more dressed up version of the, the jeans and the hoodie. And so we have a really loyal fan base out in San Francisco as well.

• 1:02:29Guy Raz?

  So once you started to get like members of Congress wearing your clothing and women in DC and San Francisco, and did it at that point become easier to raise more money?

• 1:02:41Speaker 01

  I don't think it had anything to do with who was wearing it. You know, what we started to see was traction in revenue. Four years into it, around 2017, a VC investor approached us and he said, hey, we're just interested in learning more about you. Can you tell us? And I think at that point, I had a big chip on my shoulder because we had had total failure trying to raise from VCs.

• 1:03:04Guy Raz?

  You're four years in and you had not raised any money from VCs at that point?

• 1:03:08Speaker 01

  Yeah, that's right.

• 1:03:08Guy Raz?

  Wow.

• 1:03:10Speaker 01

  And so I was like, you know, we're gonna do this without VCs. Like, that's just the way it's gonna be. But then we met with this investor who was just really wonderful and his wife was a customer. He said to me, you know, I know nothing about women's clothing, but I'm a good student and I'm willing to learn, so will you teach me? And just came at it so differently, which really got me thinking about VCs in a different way up until that point.

• 1:03:35Guy Raz?

  And so they did invest at that point?

• 1:03:37Speaker 01

  Yeah, they did.

• 1:03:38Guy Raz?

  Because up until that point, the first four years, all your money came from friends, family, and then like family investment firms or not, right? And, you know, I'm sure that was frustrating that VCs were not throwing money away. I have to imagine that that was a huge advantage because VC money can be a real double edged sword, as we've learned from previous guests on the show.

• 1:04:02Speaker 01

  Yes.

• 1:04:04Speaker 01

  You know, I got to hold on to a lot more of my company because we couldn't raise for a while. But the result was, you know, we were, I think, in a position where we could better absorb those financial resources. So there wasn't risk of other investors coming on and saying like, wait a minute, wait a minute, like, you gotta change your product because this isn't working.

• 1:04:29Guy Raz?

  I'm assuming that your financials are not public because you're not a public company. But the last number I saw was for 2017 where you did 70 million in revenue. I have to assume it's higher now.

• 1:04:44Guy Raz?

  Do you, at this point now, do you know how much money you've raised in total?

• 1:04:48Speaker 01

  Yes, I do. Yes, I do. We don't disclose it and it's so funny because I'm... I think there's a real, there's a real dark side to talking about how much money you've raised. And I think what happens often in startup culture is that that is what you become known for. Oh, you're a gee.

• 1:05:05Guy Raz?

  That's your legitimacy, your badge of legitimacy, how much you've, and that's your status, right?

• 1:05:09Speaker 01

  Exactly, exactly.

• 1:05:11Guy Raz?

  And it sounds like you, you were, you believed in that for a while, like when these VCs weren't giving you money, maybe you thought that they, that money would give you this veneer of legitimacy.

• 1:05:20Speaker 01

  Oh, for sure. It's a, if you can't tell already, there's, this is like a constant process of self doubt and me thinking that I'm a loser and trying to, you know, navigate throughout this process and not being able to raise from VCs repeatedly when other GTC companies are raising money. It just makes you question a lot. But I think the result is like what I did was I ended up just spending a lot of time with my customers.

• 1:05:47Guy Raz?

  Yeah.

• 1:05:47Speaker 01

  Internally, we call our customer Samantha, but you know, where is Samantha working? How do we make her happy? How do we make, make products that she really loves? And so by the time we took in that money, that precedent was already set, like investors, you know, while I am so grateful for them and very thankful for them, they don't direct the future of the company.

• 1:06:05Guy Raz?

  When you think about how hard it was to convince people that this was going to be more than a niche business, right?

• 1:06:14Speaker 01

  Yeah.

• 1:06:14Guy Raz?

  And, you know, and you're a business school reject, and I say that with utmost respect.

• 1:06:21Speaker 01

  I wear it proudly, yes.

• 1:06:23Guy Raz?

  You should wear it proudly, yeah. Do you, I don't know, does part of you kind of feel like, see, I told you so?

• 1:06:29Speaker 01

  I feel that way, the I told you so, when it comes to working women not being a niche category. I feel very strongly about that. But in terms of, you know, feeling like I'm the business school reject no longer, no, not, not really. I think.

• 1:06:47Speaker 01

  You know, I feel like I'm always being tested. I've never really had this moment where I've thought like, I've showed you. I feel like I'm... The startup world has a way of always putting you back in your place.

• 1:07:00Guy Raz?

  Yeah, sure.

• 1:07:01Speaker 01

  Yeah, I think that's the way I would describe it.

• 1:07:03Guy Raz?

  I mean, you know, this is a company that's doing now, let's say, close to maybe more, maybe less than $100 million. Do you now, are you able to kind of just take a breath and say, all right, we've made it, like, nothing to worry about anymore? Or do you still have anxiety about, you know, are there things that still keep you up at night?

• 1:07:25Speaker 01

  Oh, of course. I mean, the whiskey on the rocks in the middle of the night, that never ends. I feel like I'm running a different company every two years. And this stage of the business brings a whole different set of challenges that the first two years did. You know, I will qualify that by saying, the first two years were by heart, by far the hardest two years of, I think, my life. It was just incredibly lonely, incredibly hard getting this business off the ground.

• 1:07:54Guy Raz?

  When you think about your journey, how much do you think about that, you know, this all coming as a result of your hard work and skill and versus luck?

• 1:08:03Speaker 01

  Oh, it's 99% luck. I always go back to that experience I had in Zambia. It is mostly luck. Being born to the right parents at the right time, even just like watching how different my mom's journey was as a female entrepreneur in Japan versus me, born, you know, 37 years later, and the benefits and the funding I am able to get in a way that I know that she was never able to. That is all luck. And yes, a lot of hard work, too.

• 1:08:35Guy Raz?

  That's Sarah LaFleur. She's the co-founder and CEO of MM LaFleur. And by the way, a word of caution, try not to confuse her with the other Sarah LaFleur. One of the weird things that happened when I was doing research, the first thing that came up was a Canadian actress named Sarah LaFleur.

• 1:08:52Speaker 01

  Oh, I know. I feel like I have to just reach out to her because...

• 1:08:56Guy Raz?

  Yeah, you have to.

• 1:08:56Speaker 01

  I have gotten scripts sent to me.

• 1:08:57Guy Raz?

  I'm sure. Can you do voice work for LaFleur? I read her bio. I know all about her now, too. You were on How I Built This.

• 1:09:05Speaker 01

  You should. You're like, the work is done.

• 1:09:18Guy Raz?

  And please do stick around because in just a moment, we're going to hear from you about the things you're building. Hey, thanks so much for sticking around because it's time now for how you built that.

• 1:09:28Speaker 02

  My name is Taylor Moly. I live in Brooklyn, New York, and I invented a product called Metaphor Dice.

• 1:09:34Guy Raz?

  Taylor created Metaphor Dice after decades of working in schools and in writing workshops, teaching young people how to write poetry.

• 1:09:42Speaker 02

  The complaint that most students have when they're told, "Today, we're going to write a poem," is, "I don't know what to write about."

• 1:09:48Guy Raz?

  So Taylor would try all these different strategies, like, you know, tell them to start with a simple metaphor and build out from that. But a lot of times, he would just get a blank look. But then, about four years ago.

• 1:10:01Speaker 02

  I had this girl in my class who called herself more of a math-science person. And I said, "Well, that's OK, because a metaphor is really just an equation between an idea and a thing." And she was like, "Oh, I think I actually could do that."

• 1:10:17Guy Raz?

  So Taylor gave her a menu of different nouns and adjectives she could use to get started.

• 1:10:22Speaker 02

  And she came up with, "My father is a broken mirror."

• 1:10:27Guy Raz?

  And he can still remember the poem she wrote.

• 1:10:30Speaker 02

  "He's been shattered into 1,000 pieces, but even in the smallest, sharpest pieces, I can still recognize my own reflection."

• 1:10:39Guy Raz?

  The intensity of this poem stayed with Taylor for days. And he started to wonder.

• 1:10:44Speaker 02

  Why isn't there a way to help students write poetry just by generating a whole lot of metaphors really fast?

• 1:10:52Guy Raz?

  So Taylor started to brainstorm ideas, and he eventually came up with two. The first idea was to make dice printed with nouns and adjectives. You'd roll the dice, and whichever words turned up would help you build the poem. The second idea was a smartphone app, which would do the same thing, only digitally. But since Taylor had no idea what to do next, he called up a former student named Oliver, who happened to have an MBA, and asked if he'd become his business partner.

• 1:11:20Speaker 02

  We had a lunch, and I sort of pitched him the physical dice, and I pitched him the app. And he said, "You know, the world doesn't need another app."

• 1:11:29Guy Raz?

  Oliver basically said, "Go for the dice."

• 1:11:32Speaker 02

  He said, "Oh, you know what? You ought to start a Kickstarter campaign. So you've got to pick a number that's, you know, just within reach."

• 1:11:39Guy Raz?

  So he set his Kickstarter goal at $20,000. And within five days, his project was funded, which gave Taylor enough working capital to order the first 5,000 sets of dice from China.

• 1:11:51Speaker 02

  Do you want me to roll a couple?

• 1:11:54Guy Raz?

  OK, so here's how it works. You get 12 dice in all, in three different colors. The red dice are printed with concepts or ideas.

• 1:12:03Speaker 02

  The mind, hope, love.

• 1:12:06Guy Raz?

  The white dice have adjectives.

• 1:12:08Speaker 02

  Flawed, sad, glorified.

• 1:12:12Guy Raz?

  And the blue dice, more nouns.

• 1:12:14Speaker 02

  Songbird, curveball, thunderstorm.

• 1:12:17Guy Raz?

  You pick one die of each color, and you've got the building blocks for the first line of a poem.

• 1:12:24Speaker 02

  Love is a flawed thunderstorm. Your mother is an ill-gotten kiss. Social media is a flawed experiment. Well, that's not really a metaphor.

• 1:12:36Guy Raz?

  OK, so maybe some of the word combinations might work better than others. But Taylor says lots of teachers are now using these dice and have told them that their students really like them.

• 1:12:45Speaker 02

  Early on, I had a teacher say that usually the toughest part about writing a poem is getting started. But with metaphor dice, I find that it's harder to get the students to stop.

• 1:12:55Guy Raz?

  So far, Taylor and Oliver have sold about $80,000 worth of metaphor dice. They're on Amazon and even in some museums and game stores across the country. And by the way, even though they didn't want to make an app, metaphor dice is now an app, an app loaded with hundreds and hundreds of words, which means thousands and thousands

• 1:13:15Speaker 02

  A million.

• 1:13:15Guy Raz?

  of metaphors.

• 1:13:16Speaker 02

  A million possible metaphors. And it's a lot of fun.

• 1:13:21Guy Raz?

  That's Taylor Moly. If you want to find out more about metaphor dice or hear previous episodes, head to our podcast page, howibuiltthis.npr.org. And of course, if you want to tell us your story, go to build.npr.org.

• 1:13:36Guy Raz?

  And thanks so much for listening to the show this week. You can subscribe at Apple Podcasts or wherever you get your podcasts. And while you're there, please do give us a review. You can also write to us at [email protected]. And if you want to send a tweet, it's at howibuiltthis or at Guy Raz. Our show was produced this week by J.C. Howard with music composed by Ramtin Arablouei. Thanks also to Candace Lim, Julia Carney, Sequoia Carrillo, Neva Grant, and Jeff Rogers. Our intern is Raini Toll. I'm Guy Raz, and you've been listening to How I Built This.

• 1:14:17Guy Raz?

  This is NPR.

• 1:14:23Speaker 03

  The news is about more than what just happened. You need to know why it happened, who made it happen, how it's felt in the communities you care about. NPR's daily news podcast, Consider This, gives you all of that with context, backstory, and analysis on a single topic every weekday. It's not just information, it's what the news means. Consider This from NPR.