Serena & Lily: Serena Dugan and Lily Kanter. They Built a $20M Brand—Then One Investor Almost Destroyed It Transcript from https://podmenti.com/t/7f6eacab6ef71519 needed working capital and so I ask a friend If They had any ideas of the valuation of this company. And they said no, but I'm gonna introduce you to a CFO at a private equity firm. So Serena and I went to pay them a visit. Just literally to get their opinion on the valuation. And in about Ten minutes into the meeting? The CFO went and got one of the general partners of the firm. He literally Patted us on the head. Like we were Dogs or puppies. Or children. He took a seat at the table and said You girls sure have been busy. Welcome to How I Built This, a show about innovators, entrepreneurs, idealists, and the stories behind the movements. They built. I'm Guy Roz, and on the show today, how a tiny baby boutique in Mill Valley, California grew into the luxury home goods brand. Serena and Lily. One of the hardest decisions that almost every entrepreneur faces is not what to build. It's how to pay for it. Because for a lot of companies, success actually creates new problems. The more customers you have, the more inventory you need. The more people you hire. And the more cash you burn. And suddenly, a company that seems like it should be printing money? is desperately short of it. That's exactly what happened to today's guests, Lily Cantor and Serena Dugan. In 2003, they started a company called Serena and Lily. selling beautifully designed baby bedding. And almost immediately they caught a huge break. Their first catalog landed in retailers' mailboxes at exactly the right moment. And within weeks they had close to a hundred thousand dollars in orders. There was just one problem. They hadn't actually made the products yet. Which meant they had customers, but No inventory. Demand, but no cash to fulfill it. As you'll hear, they found a pretty clever way through that first crisis, but it was only the beginning. Over the next decade, Serena and Lily expanded from baby bedding into furniture, home decor, wallpaper, lighting. eventually becoming one of the country's best known luxury home brands. But getting there required round after round of financing. And somewhere along the way. People writing the chec began to have very different ideas about what kind of company Serena Lily should be. What followed is one of the most instructive and maybe even cautionary stories we've told on this show about raising capital. Because not all money is the same. The wrong investor can cost you far more than equity. Anyway, to start at the beginning, Serena and Lily launched in Marin County, California in 2003. We'll hear from Serena Dugan a little later, but first to Lily. She grew up in Kansas City and studied accounting in college, and after a series of jobs in technology and retail, landed an executive role in Microsoft. It was the mid-1990s, just as the company was entering one of the most extraordinary periods of growth. Business history. D. dominated the desktop. I mean they were I'm not kidding you when I tell you they were print cash. They were printed cash on windows and office. Like no one's business because There was no cost to goods sold. They just gave the license serial number to Dell to All of their partners of their desktops and their laptops I mean they were compatible with every imaginable peripheral, whether it was you know, printers, mouse mice, you know, they were compatible. Yeah. So I always like to say they put the gas pedal on the right, they put the brake on the left. And they created an industry. You would stay there, I think, for about five years. Um a little over five years. And um you end up got pregnant with your first child, um and you um Decided to take I think initially to take time off, but you never went. back to Microsoft. I I left in two thousand. Yeah. And I did not go back to corporate America. Did you feel I'm I'm curious because you were I mean you were a young woman at the time and and you had this amazing run at Microsoft and probably You know, you were there at a time where you got options and shares. Did you feel like, okay, I can I can live off this for a long time, like what you know, what what I got in in compensation from from that experience. Oh my God, yes. I mean those were some wild years. I was there at a time where the stock split three times. And doubled every single time it split. I probably was there at one of the most exciting times of that Company stock. And I was lucky, I was in the right place at the right time. But Yeah, I thought we could live on that. For sure. Okay, so you You decide that you're not gonna go back. And you have you have your first Child, and tell me about how you What were you thinking about maybe doing at that point? You know. My mind works in a kind of crazy brain way, but I after having our first child, I got baby gifts. that were personalized with his name on'em, and they were very unusual. And I didn't feel like there was like an exquisite baby store that was highly curated. Now keep in mind I now have You know, at thirteen, fifteen, if you go back to my high school years, I I now practically have a twenty year career in the retail world. And so I just decided to open a baby store in downtown Mill Valley. The internet. was alive at this time. We're now talking about 2001. Um, so there was ways to you know fine things certainly not like today But Yeah. Alright, so you've got this business going. You're living in at that point you're living in Mill Valley, just north of San Francisco. But baby Things for for babies, right? And um and kids, yeah. And kids, okay. And cloth so it was like decor for was it clothing as well? We had a tiny department of apparel in the back. But mainly like It was decor. It wasn't like baby bottles and baby Pacifiers. Not a ton of gear. We did have bugaboo strollers. Bugaboo strollers, man, I remember those. That was like the That was the stroller. That was for Tesla of Stroller. That was the back of the channel. Yeah, no, we had mostly home decor. uh nurseries and kids rooms furniture bedding Accessories, gliders, rugs and We opened it in July of two thousand two. That's you and your husband, Mark. My husband absolutely helped me out a lot. July of two thousand two, we opened our baby and kids store called Mill Valley Baby. And by November of two thousand two. We moved down the street to a nearly three thousand square foot store. Uh. We were kind of bursting at the seams in four months. So this was like I can imagine you're thinking, This is amazing. Like this is really Taking off. This could be a concept. Like this could be I could open a location in San Francisco. I could open a location in Los Angeles. Or do you remember thinking that way? I mean given how no. No. I didn't think for one minute that I wanted to expand or scale what we had already done. Because so much of what we had done required my presence and you know independent specialty stores really require The owner operator. So no, there was no desire to scale. Mill Valley Baby and Kids. Okay. All right. I wanna pause and I wanna turn to you, Serena. because this is we're gonna get to where you know the two of you met. So you, from what I understand, were committed to becoming a psychologist. You went to college with the this was your This is what you were going to do with your life. Yes. Very much. But obviously you're not a psychologist today. You are an artist. What happened? How'd you veer off that path? So I graduated I took the requisite year off in Colorado. And Oddly, I started painting for the first time. I started painting. You never painted Before like So how did it enter my world? Uh I Was decorating my first House. And I would pick up shabby pieces of furniture and I I painted the furniture, so it was a table. It was Latex paint. So imagine an Ugly wood table. I painted it purple blue and painted houses along the perimeter that were. Cute. Yeah. I would have a lot of parties in those days and And I had a friend of a friend over to my house who managed an art gallery in downtown Denver. And she said, This is amazing. Can I sell it? If you can paint some other pieces, I'll show them in the gallery and I thought. Okay. And so I gave her pieces to show. They sold immediately. I painted more. They sold immediately. Wow. And meanwhile I'm applying to graduate programs in psychology. And I am just starting to feel this tickle. Of What am I not exploring because this is really fun. And I'm making money over here. And I thought well maybe I wanna go into graphic design. Got it. Okay, so you uh you wisely go to art school Um, and I guess after you graduate you you land in the Bay Area. Uh where or I guess what, you you open up your own design studio. Yes, I had to build it the old fashioned way, which is reaching out to interior designers. sharing my portfolio and we met an old friend of my husband's and she asked how I was doing and what I did for work and I told her what I did And she said, oh how interesting. I work for Pottery Barn Kids. And I know that they are looking for a decorative painter and the Kismet. Moment. And that is that these are the days of pottery barn kids being kind of the gold standard. And Baby and kids. Каталог, магазин. uh marketing brand, etcetera, in part because they develop this very loose fun, playful style of decorative painting on walls. And that it was me. It matched my style. So you would decorate things that they would photograph for their catalogs? Yeah, I would paint the walls. I partnered with the stylist and they knew what they had to shoot. I would look at the bedding, I'd say, okay, this is what I want to do on the walls. Everyone would clear out of the room. and the clock would tick because those photo shoots are expensive. And so I would have to speed paint a pattern on the wall or the section of the wall that would be photographed for the catalogs. Unbelievable the amount of money they would spend on a photo. For a catalogue. That's insane to me. Um that you right, but they want it hand painted wall. Okay, so yeah so you you've got this This design studio, and also doing pr presumably over time doing more work for In homes. Yes. I had started to really Create a specialty around baby and kids' rooms because of that um portfolio that I was building and the connection to a beloved brand. Um that was not exclusively the work that I was doing. Uh I was painting Foyers and powder rooms and And you were doing this by hand. You weren't printing stuff quite yet. Yeah, no I And this is actually where psychology and creativity really meet. I would go in. I would meet with you, guy. You'd say Uh we have this entryway. And we want something that feels like it reflects the family. And I would then go back, I would kind of get to know you. And I would meet you back in a couple weeks with visual samples of what I would like to do. On the wall. On the wall. All original patterns and Created bespoke. for your space. And your fellow that was hard to scale'cause it's just you. I wasn't thinking about scale. Right. Fair enough. Yeah. It was scalable only in the sense that I would start to hire people. I had as many as four people. getting base coats on or you know, helping me lay out the pattern or whatever, but all the brush work was me. Um I know that this is a bit of a a digression because you've you've got this business growing in in the Bay Area and um And this may have pr b pre dated some of the things we're talking about, but just going back to your personal Life, I know that your dad was tragically killed on nine eleven. Yes, he was. And at the time I was working for Pottery Born Kids. I was literally In painting overalls. And I was about to be picked up by my photo team. We were on our way to set. And I had a friend call me from LA. And he just said, You've got to turn on the T V there's Big stuff happening and He was frequently at the Pentagon. His primary client was the army, and He worked for but my family is all was all in DC And the questions were, has anyone talked to Dad? And you know, we we all Had the sense that he was at the Pentagon. And we said, Well we can't reach him because he's probably on the ground helping. Mm. Wow. Yeah. It's a d enormous tragedy and You know the loss plus trauma. Of a terrorist attack. commingled with the loss of a loved one. Mm. You know, it will always cut. Break through. For me. Yeah. Tell me a little bit about the business in it itself. I mean were you You know, by two thousand three, for example. Would you describe your business as still a pretty small business that was supporting you and you know enabling you to pay rent and do all those things? It was a great business. I it was growing, it provided reliable income. I always had a pack schedule. My goal was not Scale necessarily. It was simply to do what I love. and have a pipeline of work. And when I use the word pipeline, I think of my dad because we would talk every Sunday. He was my concicliary and he would always ask about my pipeline and he would wanna know that I was safe and building a business and you know I had pivoted from something very understandable and reliable and suddenly was a working artist. So pipeline was really important and his words kind of carried on for me and I was most worried about do I have enough coming in? And I always did. Yeah. All right. I wanna turn now to both of you and and start with you, Lily. So you you've got when we left off, you've got this thriving B baby business, baby store. And you um have have your second Kid, I guess, and you are You're out, obviously have your kid and you come back to the store and you notice some patterns that an artist drops off. Uh tell me about about what happened. Well, let's see, I had my second child I have to admit it was a fairly easy birth and I had him at two PM On a Thursday and it ten AM on a Friday. I was Ready to go. And I saw my OB and I said, I'm ready to go. He's like, You look like you're ready to go. Goodbye. So I literally left the hospital. And Yeah, I do what new mothers do and I want to do show and tell with my twenty hour old baby. I I bring them into Mill Valley Baby and Kids, and I've got my employees there. And the day before Sarina had stop by the store. And she left this Magnificent portfolio she had created the most beautiful piece of collateral. They were postcards of all of her work. In this Perfectly Die cut. flooded with pattern envelope like The packaging was magnificent. And she left it at the store the day before. And Serena, you left it you left this stuff at the store saying, Hey, maybe you want to refer me to your The people who shop in your store. Yeah, she's selling them baby bedding. And perhaps a crib. et cetera, she doesn't have the walls covered. And so it would give Lily the ability to provide a bespoke beautiful mural You know, or something on the walls. Okay. So Lily, you see these designs. These patterns. I was like Oh my God, she is so talented. I literally picked up my phone. And I call her And I'm like Hi. You left this most magnificent portfolio of your work at my store yesterday. I can't wait to meet you. And Serena's like Um Did you have a baby yesterday? I think that I said that ex those exact words. 'Cause you would gone into the store and I guess Asked for the I thought oh I'll I'll hear from her in a month. Maybe. And I think we met about a week later. I was probably under Was it under? Because Keep in mind the store is already set up. With a multiple number of cribs. And Bunk beds and twin beds, so it's already organized in room environments. And I th when I saw Serena's work, I immediately thought to myself, wow, I want people to walk in and say, I want my baby's nursery to look like that, or I want my kids' room to look like that. So I was like I love it. Let's do this. And she's like, awesome. And then she starts showing me her block printed textiles. That she was producing for interior designers, and this was all pretty custom at this point. And were you hand printing it with your Like with a block? Well, see, that's really the operative. question. So I had an assistant who was block printing and I swear I was losing money on every order. Yeah. Pretty perfect and contiguous yardage. Terrible business idea. I mean it's it's a it's an artisan business, right? This is like m you could only make a certain amount of these a month. Yeah. Yeah. I mean it wasn't a thought through business idea, it was a way of expressing myself. And the economics were really beside the point. Um, which is why I needed a lily in my life. Yeah. So Lily, you see you see these designs, um these textiles, and you're thinking These are really cool. We could Th there's something more to be done with this. Yes. Uh I wasn't all too thrilled at the time with the crib bedding options. At the time Keep in mind now we're in two thousand three. Mm-hmm. Moms were still using baby bumpers back then. Oh yeah, I remember those around the crib. Yeah. That that was a thing. But it's not a thing anymore. It's not. We had those all over the crib. I don't know. Yeah. Um I Saw her designs and I thought Those would be very beautiful. On a crib bumper, on a crib sheet. Yeah, I'll interject and say I had a thought about what a nursery should feel like. And nurseries. were not approached the way that felt right to me. And so design relates to a feeling, right? It doesn't matter if it's the bumper, if it's textiles, if it's artwork. What should it feel like? It should be more respectful than the choo choo trains and bunnies and ducks and pastel. It just The feeling was all wrong. And so, yes, I knew what the textiles should look like, and it started there. It always starts there, in my opinion, but it was a whole room. Notion. So together you're thinking, all right. There's maybe an opportunity here to do something, but let's talk for a moment about about the partnership because you meet And clearly you both Like each other. right away and you have this You both are aligned on a vision. But that happens I shouldn't say all the time, but that happens a lot, you know? I mean I've met people right away and I'm like, oh my god, I love this person and then you know You don't always know. So let's first talk about What you thought you knew. Lily W what was it? Okay, you loved Serena's designs, obviously. you're talking about maybe doing something together. But that Creating a business together's more than just like A project. Yeah. I Absolutely had amazing chemistry. With Serena. And You know, keep in mind her first project she's doing with me is she's gonna come in. And paint. The store. We we're spending a lot of time together now in the store, getting to know each other better. I remember learning about her father. I also had a tragic I I lost my father in a car accident when I was in my late twenties and I just feel like we we continued to bond. What I recognized in Lily that felt familiar. And like a good sign at each turn was This sense of limitless of possibility. And a drive. And that drive might be motivated by s you know, for me it's Mine is not logic based. And I recognize hers. is logic based and she had experience accounting and merchandising. That's why we partnered. Um You Lily, you had a business, you've got the Mill Valley baby. store, but this is gonna be a different business called Serena and Lily. And what tell me what How you you were gonna like Spin this out. as a separate standalone thing it was gonna how is it gonna what what what was your thinking around around how this business was gonna work? Like a side business? Uh yeah, absolutely. I spun it out immediately on Legal Zoom. As an LLC. Serena and Lily. And And and Serena's very dear friend is a branding marketing person and we kicked around a lot of names and She was really the one that came up with this idea of How ownable, you know. our names were. They were ownable at that time. They probably wouldn't be today. Who knows? So many people would come in and tell us they're Their girls' names were Serena and Lily. So Right. But yeah, that's that's kinda how it happened. We spun it out as a separate company. We're fifty fifty owners. I told Serena I'd put fifty thousand dollars into this business, we'd be equal partners. And you had that cash, presumably from your Microsoft options that you got during that time. Yeah. And the business would initially be Textiles. Let's let's just make textiles and and Start from there. Crib bedding. Forbidden, okay. So you are you've got designs and patterns, but from what I understand you're not the two of you. You're not like Let's go find a manufacturer and start producing rolls of textile and fabric, that was not what you were gonna do. You were gonna figure that out later, right? First you were gonna 'Cause you wouldn't really launch this until I think May of two thousand four. But in that six month period. when you start start the business. You were not manufacturing anything, right? No. Honestly, Guy, we we didn't know a damn thing about what we were doing. We Serena had a cut and sew person that could make us Samples to be used. In our photo shoot. We got the name of a a an agent that can help us in Los Angeles. Find A printing source that can print our fabric for us. So we literally, you know, talked him into Taking a risk that we were gonna be this multi multi-million dollar brand one day. And can you please just print us fiftin yards? of the following fifteen fabrics because we're doing our cut and sew photo samples. And They did it, and they took a risk on us. And we had the most incredible foto team and foto stylist. And we produced this beautiful look book. Okay. That that and we had the woman that was block printing Serena's fabrics, that was literally doing all that labor, her assistant, Maureen, she came over and started working full time. For Serena and Lily. And she I think they use the word screen scrape. She screenscraped the entire internet for every retailer. that would be the right place. To get our crib bedding into their store. And produce mailing labels for this first catalog. So this really you were gonna start with a catalogue. You're gonna mail a catalogue. to I guess a few hundred stores. around the country. Absolutely. We we kind of took a play out of Serena's playbook. Which was this gorgeous Die cut. Envelope. that was flooded with pattern with a gorgeous sticker That when you got this thing in the mail. You're like What the heck? Did I just get invited to the you know? The White House Gala? Like what is this thing, right? And you knew based on your Like your store. that that the the boutiques that would receive it, it they would look at this, they would see this right away. They did. I mean they opened it and they were like, wow. But something more exciting happened the weekend they received it. Okay, and this is w this is Memorial Day weekend, two thousand four, I guess. Yes. Okay, what what happens? Wendy Belize Hamo Who had a probably six hundred, possibly eight hundred independent specialty stores selling her Beautiful premium cribetting. literally faxed down her entire independent channel. Thanking them for their amazing patronage for the last X number of years. And she Said, I've decided to sell my brand or license my brand. Two babies are us. probably the biggest baby retailer in the country at the time. At the time. Yeah. So she basically said, I'm going mass. Thank you so much, but I'm done. Yeah. She's still around and uh obviously very talented, but this was she ha was known as as designing I guess the the best available designs for Cribs and blankets and things like that. That's correct. And she left this entire channel Without a Premium crib bedding. Company. So all of a sudden these retailers are like What are we gonna do? And at the same time they get your catalogue. I I I can't even make this up. It happened the same weekend. Wow. Let me come back in just a moment. How a desperate search for funding leads to a great deal. Until someone actually reads the fine print. Stay with us, I'm Guy Raz, and you're listening to How I Built This. Hey, welcome back to How I Built This. I'm Guy Raz. So It's two thousand four and Serena and Lily now have a wholesale business going. and they've just sent out a catalog of their premium baby linen to a bunch of specialty stores. And Our fax machine starts going and we're getting orders. It's like, oh my God, it's happening. It's happening. And they're coming over the fax machine. They don't know us, like we came out of nowhere. And they're ordering what are they ordering? Are they ordering baby sheets? Are they what is she? So at the time we sold everything as a three piece crib set, which was the bumper, the sheet, and the dust ruffle. And the dust ruffle. Yeah. It was very premium. Crib betting. And We had a minimum order requirement of four cribs. So it's basically a minimum order of a thousand dollars to open up. An account with us. And In a matter of a few weeks I just recall going. Oh my goodness, we have a hundred thousand dollars in orders. And then I think at Some point Serena and I went to a trade show the ABC Kids Expo, I believe, in Las Vegas. We had this Genius idea. Gorgeous like hat boxes. That had a window and We packaged up our crib bedding in these Gorgeous boxes. And stacked'em up in our trade booth. And I'm not joking when I tell you every single baby store stopped and said Wow, is that how it comes packaged? And we're like, Yeah. And they're like, I'll take four. You know, it was just hilarious. Like so we're just mounting the orders. For an inventory we do not have. And you were gonna get this printed in India. No, at this time we're still one hundred percent domestic. We found a cut and sew facility down in LA. And there was a There was a speed to market. That we were able to accomplish With a lot of scrapiness, scrappy thinking and scrappy vendors and so we were able to get this first production done in Los Angeles. But we didn't have the cash. Yeah, I mean so you you've got the orders but you don't have the cash. Yeah. Which is a which is a common problem, right? You've got this great hundred thousand dollars in orders. Yeah. But What do you do and you've gotta get get it to them. I mean, this is in uh I guess Memorial Day and you want to get it to them, I don't know I mean, we'd like to get it to him in the next like You know, two to three months. Okay, yeah. So We're like Hey, why don't we call all of them? Yeah. And let them know. That we are in a oversold situation with our initial production. And if they would like to guarantee Their order They would have to provide us a fifty percent Deposit on their order. And The oversold situation was that we actually had none. And Uh but they all basically s I don't remember one saying no. And so we raised our Working capital, if you will. From our channel. By asking people to deposit, right? Okay. So you get cash. And and how much you do you remember how much you I I guess fifty percent. So fifty thousand dollars. Yeah. But but keep in mind now I have scope creep going on with my initial investment. So I'm continuing to put money into the business to help us fund. I Always kept Serena as my fifty percent partner and we booked this This infusion, if you will, as a do to Lily Cantor, so that we had a A liability on our books, but not It was like a loan. It was alone. Yeah. I always felt like Without Serena we don't have Serena and Lily and without Lily we don't have Serena and Lily. So we we need to stay equal partners. So you You get these orders en en Were you the f the factory you were working with, were they cutting everything and packaging it up so you had like a Package of The dust ruffle, the the sheet and the bumper whatever cover in all in one package, like ready to go, ready to be shipped to the customer. Oh my God, that's such a painful story to even talk about. They sent us all the pieces and parts up to Mill Valley. We had this fabulous woman who worked for us in the early days who folded everything perfectly into our Magnificent hat boxes that we designed and developed. And We then shipped it into our first A hundred stores. And Unfortunately, those boxes most of them did not survive. The shipping effort. It was like Kind of a certified disaster. Because our gorgeous boxes Um didn't end up being so gorgeous when they arrived. They structurally could not be stacked, basically, or shipped. They were beautiful to look at and structurally unsound because of that beautiful. Acetate window that we put in front, which compromised the structure. We know a lot more about boxing and packaging now. It actually has to function, not just look beautiful. I don't think either of us took that into account. In the meantime, you know, as much as we were trying to get away from having to use vinyl. We had to fall back on the tried and true Packaging solution, uh, because the box solution was a disaster. We admitted defeat. Yeah. Yeah. All right, so so here here's what I'm curious about. By the end of two thousand five, you're gonna do about seven hundred fifty thousand dollars in sales, but but m the middle of that year you decide, Lily to sell the baby and kids store Um w why? I mean, was it not I mean because I imagine that was probably still bringing in maybe more money at that time than Serena and Lily, or maybe not, I don't know, but was it just you saw more potential in the this other thing you were doing? I I literally was so overwhelmed. I had another baby in between all of this. I had another baby in July of two thousand five. So I have three little boys. They're under four years old. I've got Mill Valley baby and kids that requires My time. And then I've got Serena and Lily taken off like uh rocket ship And I just remember going for a hike with my husband. In Octur of O Five. And I was like, Oh my God, something has to come off my plate. I just I can't do this anymore. And I said I think it's time to sell the store. And The next day I came into Mill Valley Baby. One of my very best clients who Any time she walked in the door, she she bought a lot of things. I mentioned the idea that I was trying to sell my store if she knew any Tiburon or Mill Valley moms that might want to buy the store. To call me. And She literally called like a few hours later. She called my store manager and she's like tell Lily I want to buy her store. Wow. So That was Pun. You know, we closed that deal in occ in december of O five. And got that monkey off my back. Alright, so you that is out uh that's off your plate, and now you are focused full time on Serena Lilly and you guys have Just give me a sense. I mean, uh Serena, you are Lily is is focused on like managing cash flow and and sort of dealing with operations and you are focused on design primarily, like making designs and coming up with different patterns and also Things that could go on. Yeah, you know, in those early days we were all pulled in to everything. If there was a crisis happening with one of our wholesale accounts, we were all brought in. While Lily was navigating around cash flow. and viability and she and I are both very similar in that we're like, Oh, here's an opportunity, we have to capture it. It's always a yes between the two of us. We don't we're both gas Neither one of us is break. So uh yeah, that was an exciting time, but my primary responsibility was design and creative. One thing that's interesting is that Is it pretty soon I think your retailers started to ask for for more stuff. Like like the stores that you were selling to, they wanted you To move from from baby bedding to to kids bedding or from from bedding to furniture, right? Is it is that right? Yes. We were doing kids. Betting Next, which was introduced in 2007. We wanted to grow up with baby. The parents were asking us to Help'em keep cause keep in mind like they had The look of our nursery. And they wanted to keep the look Bring in the big girl's bed or the big boys bed. And You know, our Our catalogs, as you pointed out, Guy. These photos are so expensive to produce. Yeah. You bring in a stylist. Serena did all the decorative painting on our photo shoots. And People started asking us for all the props. They would call our customer care. They wanted to know the The colour of paint That was on the walls. They wanted to know the rug. They wanted to know the lamp. They wanted They kept asking us to grow with the baby. Right. So that so that prompts you to start to think about moving That makes sense in that direction because customers are asking for it. I wanna I wanna ask about money. Right, because I guess I guess by the end of two thousand six you're doing a million and a half in sales. Great. still small, you are not probably able to pay yourselves much because most of that money is going to finance the business. And I guess around that time you decide you you need to raise some money. Uh first of all Is because this is a cash heavy business, right? You you have to have money on hand to make the stuff. So I'm a imagining that was one of the reasons. And was the other reason? Just to grow, to expand? Oh, absolutely. I mean the demand was creating This cash incinerator. You know, for lack of a better word. We needed working capital. And so We decided to do a friends and family. Round. I asked a friend If They had any ideas of the valuation of this company. And they said no, but I'm gonna introduce you to a CFO at a private equity firm and they hold on to some betting companies. They'll have a much better idea of the multiples and what to base your valuation on. So Serena and I went to pay them a visit. Just literally. to get their opinion on the valuation. And in about Ten minutes into the meeting. The CFO went and got one of the general partners of the firm. And brought'em in. He literally Patted us on the head. Like we were Dogs or puppies. Or children. He took a seat at the table and said, You girls sure have been busy. Yeah. And he said, I understand you're doing a friends and family round for one and a half million dollars. You want to raise one and a half million dollars. At that time that's what we wanted to raise. We saw that as the next one year he said We wanna make your life really easy. We're just gonna give you one check for that, so you don't have to go past the hat around to all your friends and family and you can get back to work. Wow, they were offering to just cover this. Cover. Okay. Sounds good. Sounds like it's a little bit more. Sounded amazing. And I mean Serena and I walked out of there going What just happened. But The but is the term sheet came in. And I met a woman who was a client at Mel Valley Baby who represented founders. That was she was a lawyer and she used to talk to me all the time and I really liked her and I called her up and I said, Do you mind having a look at this term sheet and giving me your opinion. And she called me back and she's like, I forbid you to t do this deal. You're not doing this deal. And I'm like Uh we need the money. She's like no they're asking for controlling interest in your company. for seventeen percent of your equity, you know. And she's like, No, you're not doing this deal. So I said to the associate over there, I said Our attorney wants you to strike this language, this language, this language. And the bottom line is they took out a lot of it. But When it came to closing the deal. He really wanted to know how much salary Sere now keep in mind we haven't taken a salary now for three and a half years. And I I I recall telling him we're gonna take hundred and fifty thousand dollar salaries. And he just had kind of a hissy fit. about it. He's like we you're not raising that much. You can't take that much in salaries. And my husband overheard the conversation because I had it on speakerphone. And when I hung up, he's like Honey? We're gonna take a second on the house. You're not doing that deal. A second mortgage. Yeah. Yeah. Yeah. But you didn't end up doing the second mortgage'cause you did decide to go to friends and family. That's correct. It was the middle of December. And we literally had to raise this money by the middle of January. Why? We had everything in production at this point for this two thousand seven launch, and everything had to be get paid for and brought in. And it was it was again paint and Furniture and we had probably a dozen. Kids bedding collections at this point. We had gliders, rugs. Lamps. Paint. We had expanded quite a Bit. On this next launch. And it needed to get paid for. All right, so you need you need the money fast. We need the money fast. And honestly, the partner knew that. He knew he kinda had us over a barrel. So you had to get it from friends and family. Million and a half dollars. The story is you got the money. But was it excited or were they ready? I mean sa it sounds like people wanted to be part of this, so Uh so it's probably not as hard as you thought it would be. It really was I mean Serena chased down every one of her friends and I would say half the money in from Serena's friends, half the money came in from my friends. And we raised the money in a 17 day sprint. So yes, we there was a lot of people that wanted to be a part of it. It was Pretty much every one of our family members. And a slew of friends. And Lily's Rabbi, you name it. Right. Okay. Yeah. And did you you were still primarily selling to Boutiques. And I imagine and and I you know, I know by the end of two thousand seven you hit four million in sales. But but you you don't have any ad budget, right? You're not I mean, this is all word of mouth. It's all boutics, it's people going into the boutiques. That was who you were selling to is it was entirely wholesale. One hundred percent wholesale. We had about six hundred to eight hundred stores. We had zero online. We didn't even have a shopping cart on our website. So there was no direct to consumer happening for us. Which, you know, in hindsight, building a wholesale business Is Far less capital intensive, so I don't regret that we started this business as a wholesale only. But yeah, we did not have e comm. I mean, this is like two thousand eight, so it's a financial crisis, and I imagine some of these boutiques are not gonna survive the financial crisis, right? I mean I mean so In a sense like It seems like going to t direct to consumer at this point was Like you kinda had to do that. given that you were so dependent on these Retailers. Caring your products. Yeah. I mean it was really interesting time. And it just so happened to be serendipitously at the time of the financial meltdown it wasn't like We didn't say oh my god there's a financial meltdown, we need to take control of our destiny. It was Oh, we need to take control of our destiny and Oh shit, there's a financial meltdown that literally Took out. Fift. of our wholesale channel. Wow. Shut down. So I mean talk about serendipitous timing. Because we also put together adult collections and adult bedding and started to present Adult bedrooms. And living rooms. And we put together a direct to consumer catalogue. And we sh sent out a test run of eighty five thousand books. I mean, this is two thousand and eight. landed differently than it does today. Yeah. And this would be okay, so the catalog, they get the catalogue and then you literally had a website where they would order from the And the business like I mean this is gonna have a huge impact on the I think the business d grows fifty percent. in the in the following year. The first year we were direct to consumer, we did five million dollars. The second year we were in direct to consumer, we did ten million. It doubled. That third year we were in direct to consumer, it went to twenty million. Like we had a five, ten, twenty. Spread. How are you dealing with a cash issue at this point? Because you can't get uh customers to pay Uh in advance. If it was made to order. Which our upholstery was Domestically was made to order. No. No, there was no chance. And keep in mind what years we're talking about. It was o eight, o nine. There was a complete financial meltdown happening. Nobody was touching. Consumer because It was contracting I mean I think some of the larger players like William Sinoma and R H, I mean, they were contracting in at the magnitude of like thirty percent contraction. Investing money. I did the Capitol dance across the United States. I I've lost track of how many people I pitched this company to. It was nearly impossible. In fact, Mavron, who was you know came from the money of Starbucks, they told us that if Starbucks had walked in their door right now, they wouldn't fund them. There was nobody there was nobody funding traditional brand. So you had to yeah, I mean I I I imagine like the cash issue starts to become really Stressful. That would be putting it lightly. Let me come back in just a moment. How one investor creates a problem that almost takes the company down. And why the solution is almost worse. Stay with us, I'm Guy Raz, and you're listening to how I built this. Hey, welcome back to How I Built This. I'm Guy Raz. So it's 2010, and by now Serena and Lily have raised a fair amount of money, and many of their funders now sit on the board. But Serena and Lily are about to realize that not all investors want the same thing. A lot of their backing comes from a traditional V C fund, but they still need more money. So they reach out to a new investor. We still because of this cash incinerator of this growing company we Brought in More of a private equity type of investor on the now this third major round. And so It was a family office, but they operated much more like what I would consider to be private equity, which meant They wanted Profitability. They wanted Slowing down the growth to be profitable. Th they didn't have the return expectation of say a venture firm from Sandhill Road. Right. They want you to grow, grow and this at the time that was the model. Grow, just grow, grow, grow. Because you were not profitable yet, I imagine No. And we had the venture firm who was just like We had a seventy percent cumulative average growth rate over a seven year period. And honestly, to Sandhill Road. Like we were a slow grower. They want like five hundred percent growth. Yeah. No, we were slow growers. Right. Okay, but this family office that was l telling you to slow down growth um and focus on profitability. I mean, could you have done that? Could you could could you say Was there a case to be made that you know what, let's do this, let me go to my other investors, my other my board members and say, Hey We gotta do this, we gotta conserve cash, we're gonna slow down growth, or was that just not an option? I think in hindsight. They were right. And I also think the answer kind of resides in the middle. I would say More people around the table were more in favor of the growth. It was more exciting for them to have a company that was growing like a weed. But I think it was their delivery. And the lack of chemistry that they created around our table. That they were no longer a fit. This was somebody who was who who wanted you to chase growth or wanted you to chase profitability? The latter. So Well tell me about your stress level at this time. I mean, you're you need cash, you're not getting more cash, or investors are like, We gave you cash. Some of them are saying keep growing, you're saying I need more cash. Some of them are saying slow down. And then conserve cash and meantime Are you sleeping at night at this point? No. No, it it it was very, very, very, very stressful times. I probably wasn't necessarily my best self at that time. I had three little children. It was a very exhausting Stressful time taking a lot of the joy Out of The beauty And this magnificent brand that we were creating. We realize that we have to remedy Are Lack of alliance around our table. We need to get This investor who's being incredibly prickly. Off of our capital. chart. Like we have to get him bought out. From what I Understand. threatened to sue you or he tried to sue you? He did sue us. He sued you, but what was his c what was he suing you for? Irreparable harm of his investment. Okay. And they were saying My investment is being harmed, and I'm gonna sue you for What were they asking for? We never got far enough into the lawsuit to really understand What they were suing us for besides the fact that it was time to get them bought out. What did you do? Did you Did you I mean I uh you know, when you're in a a situation with lawyers involved, they tell you do not talk to the person, don't get involved, you just let us handle it. It can be very frustrating. I've been Thankfully not in in lawsuits, but when I dealt with lawyer to lawyer stuff, it is frustrating because you're just hearing what they're telling you that the other lawyer told you from their client and you don't know Sometimes it just helps to just talk straight to the person, which is risky. Lawyers say don't do that. Sometimes it works. I actually got on a plane. I didn't call him. I I mean I I emailed and said, I wanna pay you a visit. I I went in person. To just sit down. And say This is gonna take us to the ground. Obviously you'd no longer believe in us, I think it's time that we get you bought out. But let's not like sue us to the ground. Like That doesn't serve anyone, including your investment. So Let's figure this out. You had to what did what were the terms? In your book you say fifty percent. Return. That's what you want. Okay. So you're pretty great,'cause it was about a year. Yeah. So you had to buy him out you had to buy his investment out. his his initial investment plus fifty percent return on that. Mm-hmm. So um that was gonna cost quite a bit of money. Presumably. Your existing board were the ones who were gonna have to furnish that money. Yeah. One our other major investor on Sand Hill Road. Came up. With the capital. They actually put the money into the company on top of our cap stack, on top of the capital chart. out of very heavy duty preference of A two X Preferred participating Very gnarly. Security. For anyone who knows how all of that works. And Got them bought out. But made it. Nearly impossible, actually impossible. to raise additional money for the company. Okay, this This situation to buy out this problematic investor. If they were gonna pay him out. double their investment back first. So whatever investment they put in Once the company sold or there was another round or whatever happened to go public. They would double their investment first. Plus their percentage. percentage of ownership, right? No. And they would get that before anyone else, including the founders or employees or any other investors saw anything in return. So they they had really preferential treatment and Did you protest? Did you say this is not? What we want, did you say I don't want to do this? Like Yes. Yes, we we we were like this is crazy. And our board chair at the time said we don't have a choice. This lawsuit and this investor are going to take the company under, so That's the choice you have right now. Is to take this investment and we were kind of at A place where we just had to Take it. Put our heads down and go build a company. the reality is like you got unlucky. You had an investor who just was gonna cause a problem And you had to solve that problem. I I wanna throw in there that There's good money and there's bad money. We learn that. Yeah. There is definitely a correlation. Between how badly you need the money And when you are raising money. what the terms are. So Agregious terms are more likely if you need the money. And they can read that. What was the valuation at the time? Over. Fifty? It was not. It was not over fifty at that time. Yeah. Alright, so you but you had no choice. You had to do this deal, and it meant that it was going to affect your I mean you could you know, it was gonna sort of I guess get Get rid of this problem. And you could move on, but was it g w were there gonna be any long term consequences from the deal? I mean I absolutely told our board chair I'll remember it. Just like it was yesterday, I said to him, We will never be able to raise another dollar for this company. couldn't raise the money because y no investor would raise money in a company with That that had an investor with terms like this. They would want the same terms. Yeah. And then uh the everybody would at that point would want the same terms. You know, and it was like, Wait a minute, what are we doing over here? You know, we're gonna end up with twenty cents at the end of this, and so are our friends and family are the people who believed in us. at the very beginning are gonna get twenty cents. So it's like Uh. I realized that it was time to restructure the company to figure out how to Get rid of the This insanity on our cap chart. And I knew that was gonna be the next major project. But at the time we were getting ready to launch a store in the Hamptons, there was a lot going on at that time that we just needed to get back to work. You just need to focus on work and then you would solve try and solve this problem or challenge on the cap table later. Maybe maybe you could you would find a b somebody who would just buy them out and something was just by the company, you know, or something. Like we were just at a place where We needed to solve Uh This Distraction. And Knowing now what I No now versus then. I probably would've Pounded my fist on the table a little bit harder. And said no. We're not taking that deal. And just take the risk that You could you could you know, you could fight this. other investor of the law and but just settle him down or s I don't know, you know. And so basically at that point. 'Cause I think by twenty ten you do you're doing twenty million in revenue and you're I mean, that's no joke. Now you're really I mean now you're approaching a medium sized business, right? And uh But what I'm trying to understand is if you can't Raise money. What do you you're back in the same situation? You don't have working capital. You're just growing. It's a Good and bad problem to have. But it's harder now because it's even No no one's gonna you don't wanna raise money from people who are gonna ha demand the same term. So what are you doing for Capital. Well, it just so happened in the next year or so. We got two acquisition offers. Sadly. They were nearly impossible to take. Because of the preference that was on the stack. And So much of the value of these acquisitions was in the earn out. Mm-hmm. And that's what, you know, Serena and I would sign up for And basically you were you were selling You might get a little bit of cash up front, but is it the earn out is where you would make your money. Exactly. But because of the terms of from these other investors and the and maybe the acquirer. There are not might not m there might not be much left. That's correct. And meanwhile our investors Want us to take the acquisition offer. Regardless of the egregious terms, including uh owning In perpetuity. Name, image, and likeness. In perpetuity. I mean, but you guys didn't have to take those you didn't have to take that acquisition offer because you still controlled. presumably controlled the the company. Listen, we The board could have voted. To sell the company. because they had enough votes around the table that were incentivized to sell the company. The problem Is that the Acquisitions were requiring Us. To sign three employment contracts. So we were kind of still had the leverage because we were like sure guys You could sell the company, but we're not signing three year. Right. Employment contract. So you can imagine how well that went over. Right. That wouldn't be as attractive to an acquirer if Serena and Lily were not involved. That's correct. And that that really honestly became the rub. And it also became a pretty serious rub. with our board. Did it c uh with tension. Yeah. Tension threats. Um The it was an ugly time simultaneous to our uh attempt to open our first store. So there were battles in the months leading up to a very big moment within the the company and the life of the brand. And you're building the plane as you're And you like get a store, you're opening a store. You open the first brick and mortar store in the Hamptons, which I think you do strategically make sense. I mean the Hamptons. It's a lot of money is there, a lot of high end shoppers, people who have homes in Manhattan. They're there on the weekends, they're There's word of mouth. that comes with being at the hand. Is that was that the reason why? Because you're in Mill Valley why wouldn't you open in San Francisco, for example, or or in I don't know In Los Angeles. I'll jump in on that one. Uh it wasn't important to us to put it in our own backyard first. We wanted it to have its greatest chance of success, and I don't know that Uh Marin or San Francisco Was that. And everything aligned to support its success. Did it work? That store? Oh yeah. Was it The right Choice for our first store. Probably not. But you know what? It put us on the map with every a major media New York So we had You know, some Unintended consequences as a result of where we planted our beachhead. Fact of the matter is, that was the first time. That any of us had seen any of our product collected somewhere. It lived in a warehouse. It lived in our imaginations. It lived on set when we were photographing a a A room. for the catalog, but we never had it spread out in front of us. And so we were able to articulate the brand mood and ethos so completely because of that location, because of Um how funky and fun that space was and It was essential. to building the brand that came after it. Okay. So you've got the you've got that store and mean time you've got acquisition offers and Some of them are challenging. But I guess one of them does come through that is Let's say good enough. It's a a family office and uh they uh offer to acquire Serena Lily and And and you guys Decide to go with that one. J had to accept it. Yeah, it's a majority shareholder Uh Acquisition in the sense of I'm gonna come in. And Clean up your cap chart. We're gonna buy everybody out. We're gonna we're gonna give a tender offer. We're not gonna force anyone out. Аніванку стай ім той. And honestly, it was a dream come true. And it And it happened as a result of opening our store in the Hamptons. Because That investor Saw it. And and so you presumably you explain the situation. And they uh and they're interested in in and helping and working with you. Yeah, we did a really like genius restructure. So anyone who wanted to leave at this time Was granted A price. And they could leave. Um they could sell their shares. They could sell their shares. Many of'em were making At that point. Over three X. And they could sell their shares. Or They could convert to common And they can ride along. in the car with us. Alright, so you um okay so you now and the commitment that you guys made was to you didn't wasn't gonna be a three year commitment, it was probably gonna be What a year two a year a little more? We are. All in. We were excited to get the Grow this thing. I don't know. I I like to refer to it as like a triple gainer on the balance beam and we landed on our feet. But don't you feel like that was the way it was gonna turn out? I n I as stressful and awful as it was, I just always knew that we were going to end up in a situation where we could do a triple gainer. On a balanced beam and land on our feet because this brand. was not done. No. We weren't done. It felt inevitable. Yeah. Аміню манієр з стрес і конфлікт. Did that just Take all of that away. That acquisition. And the terms of it,'cause you now you're back, you guys presumably are staying on, so you're common stock. holders now. Now it's sort of back A little bit back to where it was. Although now I'm assuming that that this this acquire owns the majority of the company. Yeah, it was definitely over fifty at that point. With their support. Really scale this to something even bigger. Yep. I will say that we opened up Mm-hmm. Magnificent stores. Um in the next year to eighteen months after this new infusion. And things were going great. And I have to be honest and tell you that I was Absolutely exhausted. Um, I ran this sprint. В тремс стрес. And I'm a scrappy Innovator. And now we were really becoming a grown up company. And there was a lot of meetings. That would prompt you to to I'm assuming to say I'm This is great. I'm gonna You know, once you guys are ready to replace me, I'm out. owner, the new um majority shareholder. I said listen. This brand needs someone who can really scale it. And I hadn't really spent enough time with my children at this point. And I wanted to spend more time with them, and so I kinda said I Like to Do a search. And find the CEO. Yeah. I mean it was just time. So you I think your last day is the l was the last day of the year of twenty fifteen. And I think Um Serena, you stayed on. In a in a consulting Well, Initially I stayed on in my in my role, but my role was redefined. And I lasted maybe six months. And then I left and had essentially a part time role. That was external. And at this point you both have completely stepped away from the company. Like I I think today neither of you own any shares anymore. Um and and both of you have started Your own new design businesses. But I'm curious, I mean when you guys See Serena Lily out in the world, right? Ha how do you feel about it? I mean I th I think it sounds like both of you are proud, but is it more complicated than that? I I mean I think of other founders whose names are on brands that you know that they're no longer part of and I don't know, it's th there's there's mixed feelings about it. Of course there are mixed feelings. I think that the Overriding sentiment is pride. First and foremost. Um there are many ways that this could have gone. We've all seen examples of uh founders exiting a brand and the brand deteriorating. I think that they um Have done an amazing job keeping it aspirational. I Дефні рекогніз. in the overall aesthetic, but I also know that that is part of the strategy. You know, you have to reach And appeal to more customers. In order to grow a brand. So I recognize that. Yeah. Billy. I'm with Serena a hundred percent. I feel a deep sense of pride. uh when I see the st the stores are gorgeous. Uh Every time I'm in a city that has a store I make it a point to introduce myself to the employees. And I really, you know, I hope we've built a heritage brand that will be around in a hundred years. When you when you think about the the journey you took and and I if you've heard my show you know that I always ask this, how much of of where you you got to do you attribute to the work and how much you think i is due to just luck and and um you know serendipity and and and all everything else. Um first to you, Serena. I don't believe that there's any such thing as luck that you don't participate in. I think There are so many examples of ways in which We did something unlikely. And some would say we were lucky to have So and so. uh come knock on our door. Um I would say we listen to our guts. We are positive. We are inviting and we invite in good things. Billy? Yeah. I mean I agree. I think that Part of success. In entrepreneurship is Resilience and Tremendous hard work. And the ability to pick yourself up. when honestly you've been knocked over. And I Can't emphasize enough the importance of that. to be successful. There was so many opportunities where we got knocked over and we just the resilience was And yes, we had some lucky breaks. Uh We happen to be at the right place at the right time, but Boy did we work hard. That's Lily Cantor and Serena Dugan. Co founders of Serena and Lily. By the way, an interesting biographical detail from Lily's past is Back when she went to college at Arizona State University, she worked at a men's clothing store with someone else who's been a guest on the show. The late designer Kate Spade. In fact, Lily worked with both Kate and her soon to be husband, Andy, at Carter's Men's Clothing in Phoenix. It was at a time, she says, when they were all pretty broke. Years later, Kate Spade wrote the Ford to a book written by Serena and Lily. Called nursery style. Hey, thanks so much for listening to the show this week. Please make sure to click the follow button on your podcast app so you never miss a new episode. And if you're interested in insights, ideas, and lessons from some of the world's greatest entrepreneurs, please do sign up for my newsletter at guyroz.com or on Substack. This episode was produced by JC Howard with music by Rantine Arabowie. It was edited by Neva Grant with research help from Catherine Cypher. Our audio engineers were Robert Rodriguez and Quasey Lee. Our production staff also includes Casey Herman, Chris Massini, Alex Chung, Carrie Thompson, Carla Estevez, Sam Paulson, John Isabella, and Elaine Coates. I'm Guy Raz, and you've been listening. How I built this.