Cofounder and Chief Creative Officer of Loeffler Randall

21:08And I remember there were weeks where we would have like one bag would be doing like a million dollars in sales. I mean, they had a lot of stores.

21:15Jessie Randall:Wild times. Yeah. Okay. So then at a certain point in your banana days, you and your husband were talking about starting your own company, but I read that you didn't actually know that it was going to be footwear. And to your point earlier, you had not done a lot of footwear. So why did you start talking about having your own business? Why did you land on shoes to start? It sounds silly to say, but our wedding was such a production and it wasn't like a fancy wedding. I mean, we didn't have any money to spend on this wedding, but there was a lot of like custom pieces of the wedding. There was a lot of like letter pressing and like custom favors.

21:51And this is like way before Pinterest, you know? And I think we both felt like, wow, if we could produce this, you know, my husband's a real entrepreneur, I would say much more so than me. And I always say that if I didn't have him, I would be like hand-making shoes in my kitchen. Like I like personally being the person making things. I love the craft and I'm not looking to sort of like take over the world. I like to create beautiful things that I can wear and that other people can where, but he's like really the entrepreneur. And so I think we just started to think we had come from that ad agency, which was very entrepreneurial.

22:30And we started to think like, maybe we could do this, but we didn't know what we were going to do. I remember at one point we were like, maybe it's going to be cleaning products. And then I was like, I hate cleaning. You know, I just very quickly realized like, this is going to be so full on that what we end up doing, we have to be so passionate about it. And so we started to think like, oh, maybe it should just be handbags because that's what I've been doing. But I was so burnt out on handbags at that point. And I have always loved shoes. I'm obsessed with shoes. Every weekend was about like, let me find some vintage shoes that I can wear.

23:10I didn't like the kinds of shoes that were available to me on the market. It was a time when footwear was very quote unquote sexy. And I didn't think that that kind of thing actually was sexy. That wasn't sexy to me, like a super high heel, a super pointy toe. This was not my aesthetic at all. I was wearing a lot of 80s boots with like a straight shaft or like an 80s flat or 80s pump with like a low heel. That's what I loved. And And so anyway, Brian was like, we're just going to have to do shoes. This is like your obsession. And I remember saying, well, we can't do shoes because shoes are so technical and I've never done shoes.

23:51And that's what everyone would say at Banana because they had footwear there and everyone would be like, oh, it's so technical. And then I don't know how I got the guts to say that I could do this, but I did learn that there's this thing called a modelista at the factories and their job is to make sure that things fit. they're the pattern maker. They're the one making the technical refinements. I started to realize, you know, I'm good at construction. I have an understanding of how things work, but like for the really technical things, there is someone who's, that's their job. And I don't necessarily have to have that be me.

24:26So that was a huge unlock. And I took a shoe course, like you made your own pair of shoes, but they were like handmade. There was no equipment, but I really learned a lot about construction and, you know, I started basically sculpting toe shapes out of Sculpey and like drying it in my toaster oven to get the toe shape I wanted. And that's how I ended up getting the toe shape sent to the factory in Italy to show them what I wanted the toe shape to look like. So it was very scrappy. This is amazing.

24:59Jessie Randall:Okay. So walk me through, like, how did you make your first collection? And at what point did you have enough save that you could give this a go and walk from Banana? Or did you do both at the same time? So I was working so much at Banana, I didn't feel that I could do both at the same time. And so I was saving up a lot of money for my living expenses. So basically what happened was I started designing some ideas. and there was a woman that I had met at Banana and there's this thing called an agent that you needed to have that would like take you around to the factories. She introduced me to this agent.

25:38We went over to Italy and the first factory we went to had made my shoe. They had it on a pedestal. They had made it in the exact material that I had specked it in. And I burst into tears. And it was the beginning of this partnership that we had with them for many years where we just started collaborating together. And I made a very, very tiny collection. I think there were maybe five styles in my first collection. So it was teeny tiny, but it was a dream come true.

26:12Jessie Randall:Okay. Wait, tell me about that first collection, five styles. How did you think about distribution? How did you think about selling? And do you remember what the styles were? We had this woman who had been brought into a banana. Her name is Diana Broussard. She actually has a shop in the West Village and she's an amazing designer. But she was brought in as this very high level consultant across all of accessories. And she had her own shoe line at the time. And I remember one day Bergdorf Goodman came in to see her footwear. And I'm looking at the very junior buyer and we look at each other and we realize we know each other.

26:47This girl and I were dating best friends when we were in high school. And it was just the craziest thing. I had not seen this person in like 10 years or something. And she was like, what are you doing here? And I was like, well, you know, I'm starting my own shoe line and I'm trying to learn how to, you know, have an appointment. And she's like, well, when you get the line together, come see me at Bergdorf's, just bring it up to Bergdorf's. And I was like, oh my gosh, yes, I will. Meanwhile, I had a friend that knew Stephen Allen. Stephen Allen was like the best showroom I felt like. And we brought like just very rudimentary prototypes.

27:24And he was like, I want to represent it. Wow. Yeah. That was huge for us. So I think we sold 3000 pairs of shoes our first season. Whoa. But as you know, it's not even about your first season. It's about your second season and your first season has to sell out. And so I remember like, I wouldn't even give my mom a pair of shoes. I was like, you have to go to Bergdorf and buy them because I need the sell through. And so we did have a good sell through, which was great.

27:54Jessie Randall:That's amazing. Okay. So how did you start thinking through growth and next season? And do you have enough ideas to keep going? Walk me through all of those important early details. Yeah. The second season, I felt a lot of pressure. How do we keep going with this? And again, it was just me. Brian was still working full-time in advertising. How did you explain the brand and the point of view in those early days? I remember one of the first press articles that was written about us was called Sweet and Low Down. I don't really identify with the word sweet, but it was these shoes that were lower heel heights.

28:33It did have like a sweeter toe shape that wasn't so pointy as so many others were at the time. It was like this very specific, like rounded almond toe shape of the pump. And then we had a really big hit product with our Matilde boot, which was like this low wedge boot that because I'm not a merchant, I introduced in the spring, which was like really dumb. but like that boot really put us on the map.

29:02Jessie Randall:So let's talk about those early years. You won a CFDA award. You added categories as well. So in addition to shoes, you also added handbags and ready to wear, and you ended up doing like$10 million in sales. That's crazy. We didn't even realize like how crazy that was. And I won the Swarovski award two weeks before I gave birth to my twins. It was one of those things where it's just like, I never would have even thought that that could have happened to me. It's amazing. Talk to me about some of the early hits. So the Boo early hit, like what did you learn from the hits and some of the maybe misses in terms of how you were thinking about product development, category expansion, et cetera?

29:48Yeah. So I think like our two biggest hit products were that pump that I had designed. It was called the Harriet pump after my grandmother, kind of like an eighties pump. And then this boot that was like a flat boot had a very small wedge heel. What I learned from the boot was that it's really nice to do something that has a small twist. It's not just like a totally vintage shape. Putting the wedge on it was something that I hadn't seen before. You know, always try to have some little point of differentiation, something that is pushing it a little bit from what other people have seen.

30:30Jessie Randall:So at what point did you start building out the team and how did you feel about that? It doesn't seem like you had a great deal of management experience? No, I don't think I'd ever been anyone's boss ever. Yeah. That's like probably one of the biggest mistakes that we made was that I just didn't know how to go from me doing everything to bringing in other people. It was really hard for me on the design side to bring in other people. And so basically I was doing all of the design of the footwear myself and I was pregnant with these twins. And both of my twins went to the NICU, but my daughter ended up staying there for a month.

31:13And then I didn't get a maternity leave. I literally went back to work full time, even though I had just had twins, because it was our livelihood. And that's one of the things that I think is not the smartest idea about going into business with your spouse is that all your eggs are in one basket.

31:29Jessie Randall:So it was tricky, but I think just by necessity, I had to start hiring some people. And I think there were fits and starts. Some people were a really good fit. Some people weren't the best fit. And I think I had to learn how to manage people. It's really hard. And then how long was the company up and running before your husband came in to work on the business side of things? I mean, I know he was obviously always involved, but he still had his day job for a while. Yeah. I remember one day he just showed up at the office and was like, oh, I work here now. And I was like, excuse me? He was like, yeah, I just quit my job today, which is very my husband.

32:11He's like very impulsive. And I was like, oh, that's really interesting. Most people would like discuss that with their spouse before they did that. But he just like quit one day and was like, I work here now. And you know, he's worked here ever since. So it worked out. Thank God.

32:25Jessie Randall:What advice would you give people about working with your spouse? What do you think makes it work? Well, it's hard. My first boss, Margaret, she had had her own handbag company before she started working at Banana. And so she had given me this really good advice. She was like, if you start a company, you have to start it with a partner and the person has to have the opposite skill sets that you have. And then she said, and the second piece of advice is you have to sell something that comes in sizes because she had had this handbag company and she was like, you know, if a store comes in, they're going to buy three bags from me.

33:04She's like, but if I was selling jeans, they would have to buy three size runs from me. So these were both very formative pieces of advice that I really took to heart. And I do think that that's one of the things that kind of works about me and Brian is that we're so different and we have really different skill sets. You know, I always say like, he's all gas. I'm all break. I come from a place of like fear and like, wait a minute, slow down. And he's always the one that's like pushing us forward. And it's very annoying for me. But I think, again, like I would be hand making the shoes if it wasn't for him.

33:43And he would probably be bankrupt if it wasn't for me. You know, it's a nice like yin and yang, I guess. He's the kind of person where he will not take no for an answer. He will ask someone to work with him 50 times. And if they say no 50 times, he'll just call them the 51st time. I'm the kind of person where if like someone even like remotely rejects me, I will never approach them again. We're really different skills. And obviously, you know, he had been a banker, like his first job out of college. And so he's like a math genius. He's very good at numbers. I think what's been good is that we do really separate things.

34:23He does not get involved in the design of the company. And I do not get involved in like the legal, the financial, like it's really, really separated what we do. The one thing that we do kind of overlap is the marketing. And so that's what we always fight about. Cool. but we also have a rule we had this advisor and he had to be the referee in many fights between me and my husband and he just was like brian you're not going to talk about work on the weekends or after work and my husband would talk about work 24 hours a day he's a workaholic and so i will remind brian of that i'll be like you know rodney says we're not going to talk about this But like, it's just been really wonderful, like having another leader in the company now that really sits between me and Brian.

35:13And that has just been so wonderful, because I think we both respect her so much. And she's so brilliant. That's amazing.

35:21Jessie Randall:Also amazing, your brand recently celebrated its 20th anniversary. Who What Wear will be 20 this fall. Wow, congratulations. It's kind of crazy, and to you, it's wild looking back on like I too started out as like a baby editor at Elle. I did not have a great deal of experience when we started a company. It's crazy that we're here all these years later. I am so impressed by the fact that you have spent those 20 years growing successfully and in an authentic way and that you didn't even open a brick and mortar until 2021. Is that true? Yeah, we had the brilliant idea to sign our first retail lease in January of 2020.

36:07Fun. So that was like not a good luck moment.

36:12Jessie Randall:But you now have four storefronts. Yeah, we have four and we're opening our fifth. It's been so fun. Like we had had a ready to wear line early on in the business. And then I ended up having this very, very dangerous pregnancy with my third kid. And it was kind of like a make or break moment for that ready to wear line. And I was just like, I can't do this. We stopped doing the ready to wear piece of the line. But I always said like, I don't want to have a store unless it's like a full expression of the brand. I find that shoe stores are a little serious and like a little boring. And so I said to Brian, like, I really want there to be clothing there to sort of create the whole world of like flagship moment.

36:56Yeah. And so we had to get this ready to wear up and running before I was willing to think about opening this store. And we were scared to open. I mean, again, we're like a small family business. I was personally guaranteeing these leases. I mean, it's really scary. And like, I don't have like a family member that could rescue me. I'm always like, I hope I don't end up in debtor's prison. You know, like it's scary. So I was too scared to do it for a while, but then of course decided to do it right before COVID, which was so stupid. But how would you have known? I know. And COVID was so terrible.

37:36But having the store and knowing that we had to pay that rent for 10 years or whatever the lease was, it was sort of this thing forcing us this carrot to keep going. We had to. And it was kind of a happy and creative thing because we were designing the space. And even though it was such a scary time, it kind of helped get us through. But what happened was we ended up having this shoe that was the biggest hit of our entire life of this company, which was this wedding shoe. It was really gaining traction going into COVID. We had had like our biggest year ever because of this shoe. And then, you know, the whole world goes on pause.

38:20And, you know, we had a really tough time. It was really dicey. And then coming out of COVID, I mean, our business tripled because there was like this backlog of three years of weddings. Yeah. You know, I always say it's so rare to get a hit product. I think I've had two really hit products in the 20 years. One was the boot. One was this pleated bow shoe. Everyone's like, okay, come up with the next one. I'm like, this is like a miracle when it happens. And so it was crazy.

38:50Jessie Randall:So today, in addition to your own stores and additional one opening, your products are sold by hundreds of retailers, including places like Net-A-Porter, Moda Operandi. You have a thriving ready-to-wear business, the Bridal Boutique. You've expanded your accessories to include jewelry and belts and hats and more. You also are my fellow sub stacker. You launched a sub stack last year, which I enjoy so much. I love your packing stories in particular. You do an amazing job. But as you look back on 20 years of running your brand, what piece of it are you most proud of? Because you've done so much so well.

39:36Thank you. That's so sweet. What am I proud of? One thing I always say is I just sort of like always felt like intense mom guilt that I was a working mom. And one time I was like really frustrated and I was like, you know, I'm done. And my daughter started crying and she was like, but we're so proud of what you do. And so like, that is the most important thing to me is that I do think that my kids are proud of it. And while they've witnessed probably a lot of fighting and a lot of like stress, they have witnessed their parents like working really hard towards a shared goal all these years. So I would say like, that's what I'm really proud of.

40:20I'm also proud of that. I love the product that we make because I think when you have a company and there's so many people whose livelihood relies on me, you know, like all our factory partners, all the people that work here. These things like they have to sell in order to support all the people that this company supports. And it's a lot of pressure. And sometimes you can be like led down the wrong path. Buyers will come in and they want something that isn't really you. And Brian's like, I got to keep the lights on here, you know? But I'm really proud that I've like really stuck to my guns. There's definitely been times where I've like maybe veered a little off course or put something out.

41:00I felt like I had to because I was being told to do it, but I really do feel like everything in the line is something that I'm proud of. It's something that I would wear myself and that I love wearing myself. So I think that's what I'm most proud of. And I am sort of proud of my sub stack because - You should be. Thank you. I mean, it's small, but it's just been like this really wonderful community. As you know, it's a lot of work, but I felt so welcomed there. It's a creative outlet for me. I put a lot of time and effort into that thing.

41:33Jessie Randall:But it's like, it's such an interesting thing because I think part of the reason it's rewarding is because it's very vulnerable at this stage in our careers to be writing as ourselves and like putting ourselves out there in this way. It's intimate. It is. I've been hiding behind the who, what, where byline for 20 years. It's different in that way. It's really different. But I have to say, I mean, knock on wood, I have found the community on Substack to be really supportive. Feels like the old internet. Yeah, exactly. Like I have been feeling less and less interested in Instagram. It's not like a happy place for me.

42:12Jessie Randall:Oh, you don't enjoy being a video creator? Exactly. Yeah. It can be like this really negative place. Where you don't even see the people you want to see. Yeah, exactly. And I just feel like when I've gone over to Substack, it is more intimate. And these people are really electing to engage with the content that I put there. Whereas on Instagram, it's so pay to play, I feel like that who knows who's seeing it. And if you get 80 likes on a post on Substack, I'm like so psyched. But then when I get that many likes on Instagram, I'm like, oh, nobody liked that. That's a failure. Yeah. And I feel like there's just so much more substance on Subsec too.

42:58It has the visual element, which I'm such a visual person and I love like beautiful things, but it also, there's a lot of like intelligence and thought that goes behind it as well. So I'm a big fan of it. I've really enjoyed it, but it's yet another thing that I'm like always on my phone about. Yep. It's hard to get away from the phone. I get it.

43:17Jessie Randall:Okay. We have three final questions that we ask all of our guests. So the first one is about mistakes because we all make them in the course of our career, but I don't think that women always talk about them as much. We tend to, as a society, talk about the highlight reel. And I think it's important to talk about the mistakes because it reminds everyone that you can screw up and come back and it's going to be okay. So I'm hoping that you can tell me about a mistake that you've made at any point in your career and what you've learned from it? I mean, we would have to have hours and hours to talk about all the mistakes I've made.

43:51I really feel like as an entrepreneur, I wonder if you feel this way too, but I feel like it's sort of a mirror that gets held up to you and you're going to see your greatest strengths and you're going to like get confronted by every single thing that sucks about you. You know, it's like every weakness you have, every thing that isn't the greatest about you is going to kind of be illuminated for you in these various situations. So I think I've had that. You know, there's been very specific things. Like I always tell the story of we came out with our boot in rubber as a rain boot, but we forgot to put a tread on it.

44:31Oh no. Yeah. Yeah. We spent$80 ,000 in equipment because it's so expensive to make rubber boots. and we had announced it. There had been like a full page of it. I remember in Teen Vogue and like every editor was getting a pair and then they like came in and we were like,

44:48Jessie Randall:we didn't put a trend on it. So we had to recall all of them. Yeah. Fall risks. That always stands out to me. But then I think like an even bigger one is like some of the things I've talked about before where like just realizing that it's not a failure when you need help and that it's actually quite an accomplishment when a business becomes bigger than what your skill set can really manage. That's a good thing. It's not a sign of weakness. And it's really important to have people come in that can help you. I think that took me a long time to learn. So a lot of the folks who listen to this podcast are in their first lives and they want to make a pivot, whether that's in the same industry but a different aspect or in a totally new industry as someone who has successfully made a pivot.

45:37Jessie Randall:What advice would you give someone who's standing on the precipice of making that change, but just hasn't done it quite yet? I think it's really scary. I would just like acknowledge it's really scary and it's really brave to even be thinking about doing it. I think one thing that really switched my perspective was when I realized no one's going to do this for you. I mean, I really believed in myself. Of course, I was like insecure like everyone else, but I had this like core belief that I was meant to do something that I really loved. And I felt like frustrated in my twenties. Cause I was like, I know there's so much potential in me, but I can't figure out what it is.

46:16I can't figure out how I'm going to be successful. Like, how am I going to prove to the world that I have value? you. And so I would just say, you know, no one's going to come along and pluck me, Jesse Randall out and make your life happen for you. And I think we're kind of been taught like, oh, you know, I'm going to get this job and then someone's going to give me a promotion. It's like, you're going to have to make every single thing basically happen for yourself with some luck and some connections and all of this. But like, I felt like that was a big realization for me is like, it's not going to happen unless I just sit there and do it.

46:54Jessie Randall:Sometimes I wonder if part of this is the way that we socialize girls and the way that young women succeed in school, where in school, if you do the work, you are rewarded and someone will pluck you out and say like, look at how great this person did this. And we spend all of this time in that scenario. And then all of a sudden, it's like, and now go do it on your own because no one's coming to save you or rescue you or anything. I wonder about that sometimes. And maybe it's too easy of a concept, but we spend all of this time trying to be good girls in school and being rewarded by some larger authority that we tend to think that that's how it will work.

47:38Jessie Randall:And it's not. Yeah. I remember when I was working at Banana, I was an assistant designer. My dream was to become an associate designer. And I had this friend who was kind of a mentor to me. She was like more senior in the company. And I was like, I really want to be an associate designer. Like it means so much to me. Like, I think I'm ready. And she's like, what is an associate designer? And she's like, okay, you're an associate designer. She's like, this is such an absurd thing. If you think you're an associate designer, you're an associate designer. It's so dumb. Like it doesn't matter. It's about what you're putting out into the world.

48:16And like, you don't need this external validation of someone telling you, you are this. Yeah. It's sort of like, you are what you put into it.

48:26Jessie Randall:You are. Yeah. Okay. Last question, favorite question. If you could get in a time machine and go back in time and give your younger self some advice, what would you say? Oh, so many things. I would probably say it's going to work out. There's just been so much fear, I think, because I tend to be an anxious person anyway. And I do find that there's going to be good times and there's going to be bad times. It's not normal for it to always be good times. It's not normal for it to always be bad times. That's why sometimes when it's the good times, I start to get anxious because I'm like, oh, I know the bad times coming.

49:06But it is very cyclical. And I think just don't be so hard on myself, I guess I would say. We all are so hard on ourselves. We hold ourselves to these crazy standards. I think especially if you are a manager of people, I have found that really hard. I am the youngest person in my family and I enter a room assuming I'm the little one. It's like, not anymore. But in my home life, I'm the adult. And then at my company, I'm the adult. And sometimes you want to be baby. I've never felt that I am an adult. I'm still confused about a lot of things. I think everybody is. That's another piece of advice is that even people that seem to have it figured out, they're human.

49:52They don't have it figured out and give yourself a break.

49:55Jessie Randall:And when they think they do, they're usually served something from the universe to let them know that's not the case. The universe has a sense of humor like that. Well, Jesse, Thank you so much. This was such a pleasure as an owner of many of your shoes and other items. I have just loved watching you from afar for all of these years. Thank you so much for taking the time to sit down with me. This was an absolute pleasure. Oh, this was such a dream for me. Thank you so much.

50:29Jessie Randall:that was Leffler Randall co-founder and chief creative officer Jesse Randall for more inspiring interviews with women like Jesse head on over to secondlifepod.com where we have so many more for you to peruse if you like today's show please subscribe on Apple Podcasts or Spotify or wherever you get your podcasts. And don't forget to rate and review us. We love seeing you spread the word on social. And now you can tag us in your posts. We are at second life pod on Instagram, Twitter, and Facebook. We always want to know who you're interested in hearing from on the show. So send in your requests to hello at second life pod.com, or you can DM us on Instagram.

51:11Jessie Randall:I'm at Hillary Kerr. The show is at second life pod. Our DMs are always open. I'm Hilary Kerr, and you've been listening to Second Life. This episode was produced by Hilary Kerr, Summer Hammeris, and Natalie Thurman. Our production assistant is Raven Yamamoto. Our audio engineers are at Treehouse Recording in Los Angeles, California, and our music is by Jonathan Leahy.