For many fashion lovers, the name Rebecca Minkoff brings back memories of the handbag they once saved up for. Her Morning After Bag, introduced in 2005, helped establish the designer’s place in the accessories world. More than two decades later, her perspective on entrepreneurship extends well beyond fashion.
In 2018, Minkoff co-founded Female Founder Collective with Ali Wyatt. Through the organization and its initiative The Cabinette, she’s helping other entrepreneurs tackle familiar questions: When is it time to delegate? How do you maintain a brand’s identity as consumer expectations shift? And who do you turn to when you’re the person everyone else relies on?
Those challenges were central to the recent Ascent Summit at the Santa Monica Proper Hotel, where founders and executives gathered for programming focused on leadership, growth, and technology. Below, Minkoff shares the lessons she’s carrying forward, and what she hopes other founders take away from Ascent.
From your own experience building Rebecca Minkoff, what was one of the hardest parts of evolving from founder to leader?
One of the hardest lessons was realizing that the skills that make you a great founder aren’t necessarily the same skills that make you a great leader. In the beginning, you’re involved in everything. You’re making every decision, solving every problem, and your instincts are driving the business forward. But as you scale, that level of involvement can actually become the thing holding the company back. I had to learn that leadership wasn’t about having all the answers or being involved in every decision. It was about building a team I trusted, empowering people to take ownership, and creating a vision that everyone could execute against. At a certain point, you have to stop being the person who does everything and become the person who makes everything possible. That’s a difficult transition for any founder, especially when you’ve built something so personal.
You’ve now experienced entrepreneurship both as the founder of your own fashion brand and through working with thousands of other women founders. What is something you understand about building a business now that you wish you had known earlier?
I wish I had understood earlier that building a successful business isn’t just about having a great product or a great idea. It’s about building the infrastructure, relationships, and leadership around that idea that allow it to grow. When I started Rebecca Minkoff, so much of entrepreneurship was figuring things out as you went. There wasn’t necessarily a playbook, and there certainly weren’t the kinds of communities and resources available to women founders that we’re building today. Through Female Founder Collective, I’ve had the opportunity to connect with thousands of women at different stages of building their businesses, and one thing has become incredibly clear: The challenges evolve as your business grows, but the need for the right people around you never goes away. I think founders sometimes feel like they have to prove they can do everything themselves. What I’ve learned is that the most successful founders aren’t the ones who have all the answers. They’re the ones who know when to ask for help, when to bring in expertise, and how to surround themselves with people who challenge them to think bigger.
Fashion and consumer behavior move incredibly quickly now. How do you evolve a brand without losing the identity that made people connect with it in the first place?
You have to understand the difference between what’s core to your brand and what’s simply the way you’ve always done things. Fashion is constantly evolving. Consumer expectations change, new platforms emerge, and the way people discover and engage with brands looks completely different today than it did when I launched Rebecca Minkoff. But while the way you communicate with your customer should evolve, the reason your brand exists shouldn’t change every time there’s a new trend. For me, it’s always been about understanding our customer, what she values, and how we can continue showing up for her as her life evolves. The strongest brands don’t chase relevance. They evolve in ways that make them continually relevant to the people they serve. That requires listening to your customer, being willing to experiment, and knowing which parts of your identity are nonnegotiable.
How does a founder know when it’s time to stop being involved in every decision and start trusting other people to lead parts of the business?
I think one of the clearest signs is when you realize that everything is waiting on you. If every decision needs your approval, every problem lands on your desk, and your team can’t move forward without you, you’ve become the bottleneck. And I think that’s something a lot of founders struggle with because, in the early days, being involved in everything is exactly what helped you succeed. But scaling requires a different mindset. You have to hire people who are better than you at certain things, give them real ownership, and accept that they may approach decisions differently than you would. That doesn’t mean letting go of your vision. It means creating the conditions for other people to help bring that vision to life. You know you’re becoming a stronger leader when the business can make great decisions without you being in every room or on every call.
Several sessions at this year’s summit focused on emerging technology. Where do you think technology can genuinely help founders grow, and where is human judgment still irreplaceable?
I think we’re at an incredibly exciting moment for entrepreneurship because technology, and AI in particular, is giving founders access to capabilities that previously required much larger teams, budgets, and resources. Whether it’s understanding customer behavior, improving operations, analyzing data, or accelerating content development, these tools can help founders work smarter and make more informed decisions. One of the reasons we incorporated hands-on AI programming with Google at this year’s Ascent Summit was because we wanted founders to move beyond talking about AI and actually understand how to apply it to their businesses. But technology is only as valuable as the judgment behind it. AI can help you identify patterns, move faster, and create efficiencies. What it can’t replace is your understanding of your customer, your creative instincts, your values, or the relationships you’ve built. Technology should give founders more capacity to lead, not replace the things that make them great leaders. The opportunity is to use these tools to free yourself from the work that consumes your time so you can focus more energy on the decisions that actually move your business forward.
Community has become such a major part of brand building. What do you think separates a real brand community from simply having a large social following?
A following is about how many people are paying attention. A community is about how many people actually feel connected. You can have millions of followers, but that doesn’t necessarily mean you’ve built trust, loyalty, or a meaningful relationship with your audience. A real community is built when people feel seen, understood, and part of something bigger than a transaction. With Rebecca Minkoff, I’ve always believed that our relationship with our customer should extend beyond the product. And with Female Founder Collective, we’ve taken that philosophy even further by building a space where women aren’t just connecting with our organization, they’re connecting with and supporting one another. That’s when community becomes incredibly powerful: when the relationships and value extend beyond the brand itself. A following gives you reach. A community gives you relationships, loyalty, and staying power. And in today’s consumer landscape, I think that distinction is more important than ever.
For the women leaving Ascent and going back to running their companies, what is the one conversation or lesson from these two days that you hope stays with them?
I hope they leave knowing that they don’t have to navigate the next stage of growth alone. One of the reasons Ali and I created The Cabinette, and why we brought this group together for Ascent, is because there’s a real gap in support for women who have already built successful businesses but are now navigating an entirely different set of challenges. At this stage, the questions aren’t necessarily about how to start. They’re about how to scale sustainably, how to evolve as a leader, how to build the right teams, and how to make decisions that will shape the next decade of your business. We heard from women who have built extraordinary companies, but what I hope resonated most weren’t just their successes. It was their willingness to talk openly about the hard decisions, the pivots, the mistakes, and everything that happens behind the scenes. Success doesn’t mean you’ve figured everything out. It means you’ve learned how to keep evolving. If every woman leaves here with one new relationship, one idea she’s ready to implement, and the confidence to make a decision she’s been putting off, then we’ve done what we set out to do. Because the real value of Ascent isn’t just what happens in these two days. It’s what these women go back and build because of them.
Photo Courtesy: Infinity Creative Agency
