April 19, 2025

Lessons - Winning in the Modern Workplace as a Female Founder | Rebecca Minkoff - Fashion Icon & CEO

Lessons - Winning in the Modern Workplace as a Female Founder | Rebecca Minkoff - Fashion Icon & CEO
Success Story with Scott Clary
Lessons - Winning in the Modern Workplace as a Female Founder | Rebecca Minkoff - Fashion Icon & CEO
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In this "Lessons" episode, Rebecca Minkoff shares the realities of building and leading as a female founder in today’s workplace. She highlights the financial and emotional challenges of running a small business, advocating for candid conversations, realistic expectations, and sustainable growth. Rebecca emphasizes that profitability should come before aggressive fundraising, especially given that only 3% of women founders receive venture capital. Through her experiences and the Female Founder Collective, she champions a community-driven, education-focused approach to entrepreneurship—one that prioritizes support, practicality, and redefining success beyond just raising capital.


➡️ Show Links

https://successstorypodcast.com

YouTube: https://youtu.be/yBrQcnuknTs

Apple: https://podcasts.apple.com/us/podcast/rebecca-minkoff-entrepreneur-podcaster-best-selling/id1484783544

Spotify: https://open.spotify.com/episode/5nGxkflMJwbuBacZRBQlW4?si=22ec86d0aacd4b83


➡️ Watch the Podcast on YouTube

https://www.youtube.com/c/scottdclary



Transcript

In this lessons episode, examine the hurdles and triumphs of women-led startups. Learn why a mere 3% VC rate doesn't dictate their potential. Learn how bootstrap success stories like Pink Lilian Monique Rodriguez defy fundraising norms and learn why choosing control and profitability over aggressive fundraising paves the way for lasting success. It's actually, I think when something like that happens, we forget how recent history is, and we forget how shitty circumstances were, like not that long ago, like with people that were still, you know, still working, it's not like these people are retired, like they dealt with a lot of shit in their career. And it's just, it's, it's very sad because I've actually heard this, I've heard this, and it's very, it's, um, it's unfortunate. I've heard that from women, sometimes they get the least career help and mentorship from other women. And that seems to just be such a toxic unfortunate circumstance, but I think that you just described it perfectly. We have to put ourselves in the shoes of what some of these individuals went through throughout their career to really understand why they're so stressed in their work environment and why they act or react a certain way. But I mean, honestly, like the, the way to counteract that is to just have these conversations and to do more of what you're doing and to interview more incredible women leaders and talk about how they've created this workspace and work environment. It's just amazing for everybody. I think that's really how you, you win and you modernize and you and you be better. And, and you know what, you're still going to make people on satisfied. You know, I remember, um, this was in 20. It was definitely pre-COVID. I'd let's just say it was 2018. I sat all the moms in my office down. I said, what do you need to succeed? And I was a gas at some of the requests because they were, they were like, all right, I was like, this is too crazy. Like it was like, I want you to pay me when I'm not working from home. When I have to stay home and I want you to pay for my kids daycare, if my nanny is sick, if you want me to come work. And I was like, I love all these ideas. But like, I am not the government. And I can't pay your nanny or for your daycare. If you chose, if you elected a child, like, I, you know, I can, well, it's tough, too, because there's a lot of expenses associated. Now, then in that case, somebody could go work for like a massive, you know, billion dollar publicly traded, even trillion dollar publicly traded company that maybe has those benefits. But I, there also has to be a balance between what the company can afford and keep the lights on and how to serve the people that work for you. And that's always like, I mean, you want to talk about entrepreneurial headaches and stresses. I mean, that's one for sure. Oh my god, it's huge. I mean, even with my other company female founder collective, you know, we're a really tiny team and at first, we wanted to extend a very long maternity leave for our employees. And then I looked at my co-op and I said, I want to do this. But we can't afford first for one of our seven employees to be out for four months. Like, we just can't, you know, so we have to scale it back and when we get bigger, we can look at, you know, making it longer. But I think people forget, again, like you said, size of company and the reality of what a company can afford to do at its size and stage. I think that that, you know, something that I've thought of and this is not just for women and maternity leave in particular, but having these super candid conversations when you, when you're hiring people so that you both know where you want to go and you both know if you can support each other. And I think that this extends, definitely extends way beyond women because now people aren't staying in careers 20 years anymore. And like my suggestion is make contracts for two years and then help them figure out where they want to get two years from now and just commit to each other for minimum two years. And if they want to go different job title more, you know, bigger salary, whatever it is different company, you commit for the two years to each other, then you help as a business. So do you help them get to where they want to go? So there's no bullshit. There's no quiet quitting. There's no all this garbage that comes with these lack of candor. That's really I think the thing. Anyway, not what I was going to say as a counterpoint is, you know, when my first employee quit, I felt like it was the same feeling as being broken up with because I was like, but we're a family. We're going to do this forever together. And even in the last year, like I had been, you know, saying to my CEO, I was like, there's eight key people. We have to hold on to the eight. They can never leave. This is our team. And one resigned and one and got promoted and moved somewhere. And then we started, you know, getting in fresh eyes, fresh talent. And now I'm like, when you resign, like, great, it's an opera. Now I look at as an opportunity, like you get to go on, we get someone who's excited and enthusiastic. And it's made it a lot easier to be that nimble and they're like, great, okay, good. Next, let's find an awesome person. And, you know, recently we had a ton of new team members join and the energy is intoxicating. And it's like, oh, that's all we needed. We just need new blood. And so it's not a scary thing as it used to be. I want to talk just one more. I want to talk about all the work you're doing with, with the podcast was super woman with the female founder collective. But before we go into that, I just want to, I mean, you've taken a whole bunch of risks through your career. This is like the last point on kind of like the origin story in the come up. If you could highlight one risk or one shit, almost hit the fan moment when you were building that really stood out outside of those 10,000 bags because that definitely is a, it's a, but that's not a risk that went well. It would be a risk that you took that went well. I talk about it often, but we were the first brand to talk to our customer. There was no other brand in 2006 talking directly to their customer. Everything back then was through boutique or through a store and magazines. And that was it. Social media was just beginning. Facebook was still closed to college campuses. So if you go back to that landscape, the fact that I was online talking and DMing on like the purse forum to her, um, taking, you know, crowd sourcing, maybe that wasn't a term. You know, I'd literally be like, they'd be like, we love that purple leather you use, but can we have it with the pink zipper? And I'd be like, great. I need 60 of you to come into an order and I'll go uptown and I'll buy the leather and I'll, you know, run your credit cards personally and do it. And they were all like, we're all in. And so I think that the amount of shit we got for talking to our customer, you like, our biggest retailers at the time, sacks, Nordstrom, Bloomingdale's, Neiman Marcus, we're like, you can't talk to your customer. Like that's beneath you. Like the designer needs to stay above it all in their ivory tower untouchable. And you look like desperate talking to her. And I was like, I think, you know, my brother and I, who's my co-founder, we think we think this is a good thing. And like go with us here. And they're like, we're not going with you. You know, we're even working with influencers. Again, we were told, like, why are you working with these sea list people? There's a lot of like a elitism and I guess it's fashion design. It's a, I mean, listen, there's still a layer that shall not be penetrated by the likes of me. There, there was a lot of elitism. There was a lot of rules. And we just didn't, A, we didn't have a choice. And B, we just felt like this was, this was the future was talking to your customer, engaging with content creators and really building a more democratic community, I guess. I love that. I think that's such a smart. And it's so funny how you perceive that as a risk because I, I, I look at that as the least risky thing you could possibly do for your business. I look at that as almost like the de facto when you're a startup. Well, yeah. Yeah. That's kind of like the playbook. 20 years ago, it wasn't. It's very interesting. Okay. Um, female founder collective, you have over, I mean, when I did some research, 9,000 members, do you have more than that now? It's obviously. We, yeah. So we, we've structured the community in two ways. We have a free membership for those who can't quite afford yet to pay. So that's about 25,000 people take participate in that. Okay. And then the 9,000, yes, is like our private community that we have where we're going real deep on education. So my co founder, Ali and I really felt that the missing link for a lot of founders is all the nitty gritty ugly shit of business. And can we get women that have done it and succeeded to teach these like modules to other women. So whether it's in person zooms, you know, and then the community itself where you can go ask anyone anything, you know, what's the best AI to use or, you know, what's the best CRM platform? And you can really go deep with other women who are probably going to give you a much better recommendation than, you know, searching for yourself. What, what is the, the, the sort of the one universal problem, concern repeated post that comes up again and again and again and again. And it's it's all, it's all women founders. So what's happening that you, you just want to put out to any woman who's building something incredible right now that you see, repeat it. I see that due to the last, I'd say maybe five to 10 years of raising money, right. Now you see women are also raising money. The, the, we all know the percentages, 3% of women get funding. But I'm of the mindset that not every business should or needs funding. And there's too much this desire to be like, I raised this and therefore I'm a success. No, you're not. You just raised money. You're now beholden to investors. You sold a big chunk of your company way too early. And there's this obsession with building without figuring out profitability. And trust me, we were there. We were in the raise, raise, raise, build doesn't matter. And then when sentiment changes and investors are like, are you profitable? Oh, we need to be profitable. Cool. That's going to take us five, you know, five, 10 years to figure out like build your business to be profitable from the beginning. You know, like there's nothing wrong with slower instead of your growth or build your business to have a balance of like profitability and allow you lifestyle, right? Mobility. And instead, I'm meeting too many women are like, I'm trying to raise, I'm trying to raise and building. And I'm just like, I'm frankly, I'm just like, I think, I think they're all just looking at what they saw the last five, 10 years is that's the only way to build a business. Well, I think you could actually fall into a trap. So if you know the numbers of how many women actually successfully raised, which are horrible, and those numbers shouldn't be the numbers that they are, but they are the numbers that they are. So say it's, I was actually at this conversation with with with Julia Borstein. And it was again, it's like two, three, it was like really bad. It's almost like when you hear the number, you're like, no, no, that can't be right. But when if I was a woman entrepreneur and I was looking at that number, and I also tied into the Silicon Valley, everybody's raising, I would give up before I started because not only do I have, you know, it's not only like a 99% failure rate, but I have a two or three percent chance to go raise money and everybody's raising money. So what, so you have to like shift the lens, shift the paradigm of entrepreneurship. So you understand, okay, it's super fucking shitty that these are the numbers. But there's other ways to build businesses that I would actually say not just women should adopt, all entrepreneurs should adopt. But I think that again, if you go into it and you look at those numbers, I don't want, I don't want great women entrepreneurs to give up before they even start just because they're getting in their own head. Yeah, I'm not saying you should give up, but I, you know, the amount of women I meet, like, I'm making clothing for tall women and I'm raising money. I'm like, no one's going to invest in that. That's not a, that's not a huge hockey stick of scale, you know, open a great boutique, open a great e-commerce site, sell on TikTok shops, you know, small batch. And I've had the pleasure and honor of meeting so many women who are on again on my podcast, but they've done, you know, pink lily, over 100 million in sales, never's taken a dime, you know, I think there's some really exceptional Monique Rodriguez, one of the largest women of color exits in history. Like she didn't, she didn't take money or try and raise to scale. And by the time money came to her, she was so valuable and profitable that her multiples are like mind-blowning. Have you had Nancy twine on? I've got to make an intro. Oh, you have had. Okay, she lives in Florida now. So I know she's like, she's, she's a girl crush on her. She's awesome. She's absolutely awesome. No, when, when you just started talking through some of the people and you show you, you'll have to give me the third name, I threw out there. Thanks for tuning in. If you found this valuable, don't forget to hit that subscribe button so you never miss an episode. And if you want to dive deeper into this conversation, check out the links in the description to watch the full episode. See you in the next one.