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

Summary

Podcast Summary: Success Story with Scott D. Clary
Episode: Lessons - Winning in the Modern Workplace as a Female Founder | Rebecca Minkoff - Fashion Icon & CEO
Release Date: April 19, 2025

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Introduction

In this compelling episode of the Success Story Podcast, hosted by Scott D. Clary, the focus centers on the unique challenges and triumphs of female founders in today’s entrepreneurial landscape. Although initially advertised as featuring fashion icon and CEO Rebecca Minkoff, the episode prominently features Monique Rodriguez, founder of Pink Lily and the Female Founder Collective, alongside guest Cathy. Together, they delve into the hurdles faced by women-led startups, the importance of mentorship, strategic business decisions, and alternative paths to success beyond traditional fundraising.

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Key Discussions

1. Challenges Faced by Female Founders

Monique Rodriguez opens the conversation by addressing the systemic challenges women encounter in the business world. She emphasizes the scarcity of mentorship and career support for women, attributing it to lingering elitism within industries like fashion.

“Sometimes they get the least career help and mentorship from other women. And that seems to just be such a toxic, unfortunate circumstance.”
[04:00] – Cathy

Monique highlights how traditional corporate structures often marginalize female entrepreneurs, making it difficult for them to thrive without adequate support systems.

2. Work Environment and Stress Management

Cathy adds her perspective on the high-stress environments that female founders often navigate, urging the necessity of empathy and understanding.

“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.”
[03:50] – Cathy

Both guests agree that fostering open dialogues and supporting one another through candid conversations can mitigate workplace stress and promote a healthier work environment.

3. Balancing Business Needs with Employee Support

The discussion shifts to the delicate balance between accommodating employee needs and maintaining business viability. Monique shares her experiences with managing maternity leave policies.

“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 the size of company and the reality of what a company can afford to do at its size and stage.”
[05:26] – Monique Rodriguez

Cathy suggests a pragmatic approach to hiring and retention, advocating for clear, contractual agreements that benefit both the employee and the company.

“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.”
[06:01] – Cathy

4. Entrepreneurship Headaches and Stress

Monique discusses the emotional toll of losing team members, equating it to personal relationships.

“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.”
[06:48] – Monique Rodriguez

However, she emphasizes the importance of viewing such changes as opportunities for fresh talent and renewed energy within the team.

“It's an opportunity… we get someone who's excited, enthusiastic, and it's made it a lot easier to be that nimble.”
[07:20] – Monique Rodriguez

5. Risks Taken in Building the Business

Monique recounts a pivotal risk she took by being one of the first brands to engage directly with customers online, defying conventional norms of the time.

“We were the first brand to talk to our customer. There was no other brand in 2006 talking directly to their customer.”
[08:21] – Monique Rodriguez

This strategic move allowed Pink Lily to build a loyal customer base and gather invaluable feedback, setting them apart from competitors reliant solely on traditional retail channels.

“I'd run your credit cards personally and do it. And they were all like, we're all in.”
[08:35] – Monique Rodriguez

6. Female Founder Collective

Monique elaborates on the structure and mission of the Female Founder Collective, a dual-tier community aimed at empowering women entrepreneurs through education and peer support.

“We have a free membership for those who can't quite afford yet to pay. So that's about 25,000 people to participate in that.”
[14:36] – Monique Rodriguez

The private community offers in-depth educational modules and a platform for women to seek advice and share resources, fostering a supportive network for business growth.

7. Funding for Female Founders

A significant portion of the discussion addresses the daunting statistics of female founders securing venture capital, with only 3% securing VC funding. Monique critiques the prevailing mindset of incessant fundraising, advocating for profitability and sustainable growth instead.

“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.”
[15:54] – Monique Rodriguez

She highlights successful bootstrap stories like Pink Lily and Monica Rodriguez's own ventures, demonstrating that alternative funding strategies can lead to substantial profitability without relinquishing control to external investors.

“Pink Lily Over 100 million in sales never has taken a dime. You know, I think there's some really exceptional examples out there.”
[18:15] – Monique Rodriguez

Cathy echoes the need to shift the entrepreneurial paradigm, encouraging women to consider different pathways to success that do not rely solely on traditional fundraising.

“You have to like shift the lens, shift the paradigm of entrepreneurship so you understand... there's nothing wrong with slower and steadier growth.”
[17:00] – Cathy

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Notable Quotes with Timestamps

• “Sometimes they get the least career help and mentorship from other women.”
  – Cathy [04:00]

• “We have to put ourselves in the shoes of what some of these individuals went through throughout their career.”
  – Cathy [03:50]

• “We have to scale it back and when we get bigger, we can look at making it longer.”
  – Monique Rodriguez [05:26]

• “Make contracts for two years and then help them figure out where they want to get two years from now.”
  – Cathy [06:01]

• “When my first employee quit, I felt like it was the same feeling as being broken up with.”
  – Monique Rodriguez [06:48]

• “We were the first brand to talk to our customer.”
  – Monique Rodriguez [08:21]

• “There's too much this desire to be like, I raised this and therefore I'm a success.”
  – Monique Rodriguez [15:54]

• “Pink Lily Over 100 million in sales never has taken a dime.”
  – Monique Rodriguez [18:15]

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Conclusion

This episode offers a profound exploration of the intersection between gender and entrepreneurship. Monique Rodriguez and Cathy provide invaluable insights into the realities faced by female founders, emphasizing the importance of mentorship, sustainable business practices, and innovative funding strategies. By sharing personal anecdotes and advocating for supportive communities like the Female Founder Collective, the conversation empowers women to redefine success on their own terms. Listeners are encouraged to embrace alternative growth models, prioritize profitability, and build resilient businesses that align with their values and lifestyles.

The episode serves as a motivational blueprint for aspiring female entrepreneurs, highlighting that success is attainable through perseverance, strategic decision-making, and fostering robust support networks.

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Additional Resources

• Female Founder Collective: A supportive community offering both free and premium memberships for women entrepreneurs.
• Pink Lily: A successful female-led brand that exemplifies bootstrapped growth and profitability without external funding.

For more insights and in-depth discussions, visit www.successstorypodcast.com.

Transcript

[Scott]

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[Cathy]

It's actually, I think it's. 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. 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. That's just amazing for everybody. I think that's really how you. You win and you modernize and you. And you be better and.

[Monique Rodriguez]

And you know what? You're still gonna make people unsatisfied. You know, I remember this was in 20. It was definitely pre. Covid. 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 aghast 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 dayc. My nanny is sick if you want me to come work. And it. 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. If you chose, if you elected to have a child, like, I, you know, I can.

[Cathy]

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, a massive, you know, billion dollar publicly traded, even trillion dollar publicly traded company that maybe has those benefits. But 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 a, I mean, you want to talk about entrepreneurial headaches and stresses. I mean, that's one for sure.

[Monique Rodriguez]

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 founder, I said, I want to do this, but we can't afford for, 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.

[Cathy]

I think that actually, you know, something that I've, 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 leader, you help them get to where they want to go. So there's no bullshit, there's no quiet quitting. There's all this garbage that comes with these lack, lack of candor. That's really, I think, the thing. Anyway.

[Monique Rodriguez]

No, 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 were going to do this forever. And even in the last year, like I had been, you know, saying to my CEOs, 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 got promoted, moved somewhere and I. 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 opportunity. Now I look at as an opportunity. Like, you get to go on. We get someone who's excited, enthusiastic, and it's made it a lot easier to be that nimble and like, great. Okay, good. Next, let's find an awesome person. And you know, recently we, we've had a ton of two new team members join and the energy is, is intoxicating. And it's like, oh, that's all we needed. We just needed new blood. And so it's not as scary, I think, as it used to be.

[Cathy]

I want to talk just one more. I want to talk about all the work you're doing with, with the podcast with Superwoman, 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 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. What would be a risk that you took that went well?

[Monique Rodriguez]

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 a 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 worm to her taking, you know, crowdsourcing, 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 commit to 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, like our biggest retailers at the time, Saks, Nordstrom, Bloomingdale's, Neiman Marcus, were 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 is my co founder, like we, 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, or even working with influencers again. We were told like why are you working with these C list people?

[Scott]

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[Cathy]

There's a lot of like elitism and I, I guess it's fashion design.

[Monique Rodriguez]

It's, it's a, I mean there's listen, there's still a layer that shall not be penetrated by the likes of me. But 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.

[Cathy]

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 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, now, yeah, yeah, it's kind of like the playbook.

[Monique Rodriguez]

Years ago, it wasn't.

[Cathy]

It's very interesting. Okay, 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.

[Monique Rodriguez]

Yeah. So we've, 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 to 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, Allie and I really felt that the missing link for a lot of founders is all the nitty gritty, pretty ugly 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, much better recommendation than, you know, searching for it yourself.

[Cathy]

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.

[Monique Rodriguez]

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 percentage is 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' 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 needed 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 and steadier 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, I'm frankly, I'm just like, I think, I think they're all just looking at what they saw the last five to 10 years as that's the only way to build a business.

[Cathy]

Well, I think you could actually fall into a trap. So if you know the numbers of, 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 Boorstein 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, 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 2 or 3% 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 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.

[Monique Rodriguez]

Yeah, I'm not saying you should give up, but, 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, they've done, you know, Pink Lily Over 100 million in sales never has 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 blowing.

[Cathy]

Have you had Nancy Twine on I gotta make an intro. Oh, you have had. Okay. She lives in Florida now, so I know she's like, she's, she's.

[Monique Rodriguez]

I have such a girl crush on her.

[Cathy]

She's awesome. She's absolutely awesome. No, when, when you just started talking through some of the people on your.

[Monique Rodriguez]

Show, I was gonna name her. She was gonna be the third name I threw out there.

[Cathy]

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.

[Scott]

Hey everyone, Scott here. I just want to take a second and say thanks for listening to the podcast over the past couple years. Obviously this wouldn't be possible without each and every one of you. I have a favor to ask, so I would love to get some more information about you and why you listen to the podcast and why you listen to the show and why you tune in every week. And I have put together a short survey and we are using this to help us sort of inform what type of content we want to create and the direction of the podcast going forward. This information is not shared with anyone else, so this is just for us internally and I put together a link so scottdclary.com survey where you can go and you can fill in some information so we can know what kind of content you love. Also, for the first 100 people that respond to the survey, you will be entered into a draw for a hundred dollar Amazon gift card. So we'll be giving out one of those to the first people that respond. It should not take more than two minutes of your time to fill out the whole survey. It's really not that long and it will help you shape the future of the podc. So I really appreciate each and every one of you and thank you for listening. I just want to take a second and thank Cornbread Hemp for supporting today's episode. Now, Cornbread Hemp CBD gummies have been this really nice addition to my wellness toolkit. I don't use them every day, just when I want to unwind after those extra busy weeks, but they're perfect for those moments when you want to take the edge off and just find your balance. Really just shut off from work. And what makes them special is how Cornbread Hemp crafts them. They only use a flour of USDA organic hemp plants. That's the best part for the purest most potent experience. No fillers, no artificial fluff, just clean full spectrum goodness in delicious watermelon, berry and peach flavor. I keep them in my nightstand for those moments when I just need a little extra help relaxing. And I love how transparent they are too. Every batch is third party lab tested so you know exactly what you're getting and they put together a special offer for all success Story podcast listeners. All listeners can save 30% off their first order. Just head to cornbread hemp.com success and use code success at checkout. That's cornbreadhemp.com success code success for 30% off your first order of these amazing gummies.