Twenty Years In, Still Fearless: How Rebecca Minkoff Redefines the Rules
Surrounded by fabric samples and vision boards in her studio, Rebecca Minkoff logs onto Zoom looking exactly as you’d expect: polished, composed, and unmistakably in charge. Dressed in her trademark cool- with long black hair, aviator glasses, and a presence that commands the room, even virtually- she’s every bit the powerhouse her reputation suggests. She is a force to be reckoned with, with a raw, no-nonsense attitude and decades of hard-won wisdom. Entrepreneur, podcast co-host, bestselling author, designer, mentor (and a Real Housewife of New York City), Rebecca is the definition of sustained modern success. And now, she’s on a mission to help other women achieve the same. Along with being the face of her namesake fashion brand, she recently released the book “Fearless,” where she breaks down ‘the new rules for unlocking creativity, courage, and success.’ On April 22nd, Rebecca joined NYWICI for a live fireside chat to unpack her extensive knowledge and insight from her journey of being a fashion outsider to the fearless founder of a global brand.
1. No Guts, No Glory, No Growth
On taking risks and mindset shifts
For Rebecca Minkoff, taking risks isn’t optional, but foundational. However, it’s the mindset that makes taking the risk effective, not reckless. She explained, “When I take the risk, I go in with the mindset of I’m either going to win and it’s going to be awesome, or I’m going to fail and I’m going to learn so much. I think you can also sit down and get tactical. When you’re building a business, every new shiny object can seem like an opportunity you should take. But the more you get laser-focused on opportunities that will give you an ROI (return on investment), the more it changes where to put your attention.”
This strategy paid off when a competitor copied Rebecca’s signature “Morning After” handbag design. Instead of confronting them, she redesigned the bag to a more convenient size, priced it under $200, and rode the wave of a trend just beginning to peak: the crossbody. Following the new launch, sales soared, and her business grew 548% over three years. Rebecca reflected, “We were nimble and used what was happening around us to our advantage.”
The Takeaway: Growth doesn’t come from complacency. Take calculated risks and prioritize opportunities that move you forward.
2. You Can’t Uber Your Career
On longevity, patience, and real success
In a world where immediate gratification is the norm, groceries can be ordered from the couch, and food delivery can be delivered to your door in an hour, it is easy to want the same for your career. Unfortunately, it doesn’t work that way, and according to Rebecca, that’s actually a good thing.
“If you adjust your time horizon to the long game, you make better decisions. Maybe I would have made different ones if I had known I’d be doing this for 20 years. I thought I’d be further along by year five. In reality, we weren’t profitable; I was making $23,000 a year and having the time of my life—but it wasn’t where I thought I’d be. Your career takes time. Longevity matters. There’s nothing fast about this.”
The Takeaway: You can’t achieve success quickly. Play the long game—real success takes time. Don’t rush it, and don’t forget to enjoy the view along the way.
3. If You’re Not Evolving, You’re Falling Behind
On adaptability and reinvention
As the Rebecca Minkoff brand approaches its 20th anniversary, it’s officially considered a legacy brand – a testament to its staying power. But longevity doesn’t grant permission to remain comfortable. Rebecca knows that better than anyone. Reinvention isn’t a milestone; it’s a mindset that she’s constantly practicing. She explained: “People say, ‘Wow, 20 years—amazing.’ But after 20 years, you have to reinvent. You have to ask, ‘How do I get the next generation excited?’ Gen Alpha is coming. It’s almost harder to be an older brand saying, ‘I’m still here—don’t you still want to talk about me?’”
Looking to her role models for inspiration, Rebecca told us, “I look at Madonna—she constantly reinvented herself, keeping her music fresh.”
Reinvention isn’t just how Minkoff runs her brand—it is central to her leadership. She constantly challenges herself and her team to step beyond their comfort zones, often asking, “Will I be able to learn and grow and get exposure to things that are outside of my wheelhouse? We don’t want anyone here to stay in their lane. We want everyone to veer off, learn, and collaborate. And we definitely don’t want quiet quitters.”
The Takeaway: Legacy isn’t built by holding on. It’s built by letting go and evolving into something new.
4. Fail. Reflect. Keep On Moving
On learning from failure
Failure is inevitable, but taking a moment to reflect is integral to truly learn from your mistakes and avoid repeating them in the future. Reflecting isn’t meant to be a punishment or assign blame. It is intended to be an analytical step back to see things from a big picture point of view and then move forward. Rebecca regularly does this, asking herself questions like, “what did I do wrong? Did I do something I need to change or not repeat?” She writes them down in a book, so she doesn’t forget. She added, “When you look at failure that way, it becomes less about being embarrassed or mortified—we’re going to fail all the time.”
As Rebecca joked, “I’m only still here because I didn’t give up—not because I’m more talented or smarter. I just kept getting back up every time I got punched. This journey is hard and full of challenges you never imagined. Once you accept that, you’re not surprised or disappointed. I don’t know anyone who’s had a fairy tale journey.”
The Takeaway: Your career is a marathon, not a sprint. Use failure as fuel, not a finish line.
5. Turn Mistakes into a Golden Ticket
On creative problem solving
Even Rebecca’s missteps are a masterclass in brand agility. For example, as her company expanded, she moved the manufacturing overseas to conserve costs. Unfortunately, an early quality control mishap during manufacturing led to the rollout of “hybrid” bags made with hardware mixed with competitor materials. Instead of panicking, she launched a “Willy Wonka”-style promotion, involving her customer base in a treasure hunt, that led to her selling the entire stock and salvaging relationships with retailers.
This experience taught Minkoff that transparency and creativity are imperative to overcoming obstacles.
She explained that when these kinds of things happen, it’s how you address them that matters. “Your instinct is, I want to crawl into a hole and never speak again. But usually, I find that if you go into action, you go into problem-solving mode, and don’t get too serious about it. As serious as it is, you’ll usually come up with a better solution.”
The Takeaway: Tackle problems head-on and turn them to your advantage.
6. Accountability is a Power Move
On leadership through humility
Rebecca Minkoff doesn’t just own her wins, but also owns her mistakes. Whether working with her team or customers, taking responsibility is the best way to lead. The way she sees it, the true mark of a leader is humility. “The more times a leader can say, ‘I’m wrong, I own it,’ the more respect you gain. You’re not expected to be perfect—you’re expected to be honest. When you show up and take responsibility, most people understand. It shows humility. It shows you’re not some egotistical person who thinks they know everything.”
The Takeaway: Mistakes are inevitable. Owning them earns more respect than pretending it didn’t happen.
7. Listen First – Create Second.
On customer-centered thinking
For Rebecca Minkoff, everything starts with knowing exactly who she’s designing for. Without deep, customer-centered thinking, she believes there’s no real way to tell if a product will sell. When researching, Rebecca wants to understand every aspect of her customer’s world. Then she works to figure out how her brand’s uniqueness will resonate them.
Getting those answers, she emphasized, doesn’t happen behind a screen. It happens by getting out there, meeting the customer, and asking questions to determine their needs.
According to Rebecca, those in-person conversations reveal more about her customer than any online survey ever could. This strategy helps her carry out the core mission: to be the brand that represents a woman’s firsts—her first job, her first raise, her first big moment.
She believes that every woman should be able to afford an incredible handbag that stands the test of time.
The Takeaway: Don’t assume—ask. Listening transforms a product (or career) into something that truly resonates.
8. “Coach Said to Fake Right. Break Left.”
On out-of-the-box thinking and innovation
The fashion industry has always been a competitive, saturated space. While large brands tend to monopolize the market, they also grow complacent – relying on what’s safe and comfortable. For small emerging brands though, standing out isn’t optional, it’s survival. Back in the mid-aughts, before social media shaped how we consume everything, Rebecca Minkoff saw an opening and took a gamble. Instead of following the traditional marketing playbook, she leaned on the emerging platforms that most of her competitors ignored. She explained, “We were outsiders. We didn’t have $40,000 for an ad in Vogue, which was how you reached customers then. It was scary—you’re looking at how things had always been done and what’s safe. But we didn’t have other options. Our only option was to embrace our customer directly,” That gamble paid off. While the industry clung to old rules, Rebecca built a loyal following by rewriting them.
The Takeaway: Breaking the mold often requires scrappiness. Use what you have, even if you have to get creative with the how.
9. If it Doesn’t Align, It’s Okay to Leave.
On boundaries, authenticity, and integrity
Rebecca Minkoff is unflinchingly honest about setbacks, including her rocky stint on Season 15 of The Real Housewives of New York City. What began as a promise to spotlight influential women entrepreneurs quickly dissolved into the all-too-familiar reality TV recipe: drama and backstabbing. Reflecting on her experience, she said, “That’s not who I am; it’s not what I stand for. I’m not going to cave to get airtime. I don’t need to fight with another woman about petty things. I don’t need to talk to a woman who knows nothing about business and explain to her why we do the business we do. I won’t talk ill of people behind their backs just to get more famous.”
Ultimately, she chose integrity over fame – but also doesn’t regret it. “Sometimes you learn, and sometimes you win. And this was both. I did a lot of personal growth and learning from it. At the end of the day, it cut both ways, but I choose to look at the positives that came from it.”
The Takeaway: Not every risk works out. If something doesn’t align with your values – or move you forward – it’s okay to walk away.
10. Women Rise by Building – Not Competing
On collaboration and empowering others
In 2018, Rebecca Minkoff co-founded the Female Founder Collective, now a 25,000+ member community built on the belief that everyone benefits when women help each other rise. The goal wasn’t just access to tools and advice—it was to create an ecosystem where women-led businesses could grow stronger together. That wake doesn’t come from competition – it comes from women sharing what they’ve learned, even the messy, unfiltered parts of growth. As Rebecca sees it, community creates power—and change happens when women speak up, show up, and support one another. “If you want change and it’s not happening in your company, I’m sorry – you’ll have to be the one to stick your neck out. Be the loud one in the room. That’s how you create a wider wake for more women to follow.”
For Minkoff, collaboration isn’t just a buzzword – it’s a business strategy.
She built platforms like The Female Founder Collective and The North (her other platform for non-founders) – to offer mentorship directly from women who’ve done the work, not advice crowdsourced from Google or AI. Because as Rebecca sees it, real progress isn’t just about your success – it’s about opening the door wider for the women in line.
The Takeaway: In Rebecca’s words, the only cheat code is: “Build your network, build your relationships, and keep them close.”
11. Faking it? So Did the Wizard of Oz – And That Didn’t Stop Him.
On imposter syndrome and self-doubt
No matter your career stage, we’ve all experienced imposter syndrome and self-doubt. One attendee asked Rebecca how she handles imposter syndrome, and her response was refreshingly blunt: “I think there’s a Wizard of Oz out there making up these terms to give people complexes they never would have. Imposter syndrome is one of them.” To Rebecca, feeling unqualified isn’t a flaw – it’s a sign you’re growing. She explained, “No one knows all the answers. If you lack a little self-confidence, that’s totally normal. You’re charting new territory. You just have to show up in those rooms, roll your shoulders back, and say, ‘Someone thought I belonged here—so let me own it.’” In other words, the discomfort is real – but so is growth. Whether introducing yourself, walking into an unfamiliar room, or learning to lead, the win comes from doing it anyway.
The Takeaway: Confidence isn’t a prerequisite – it’s a byproduct of showing up. Lean into the discomfort and claim your seat at the table.
Rebecca Minkoff’s journey is proof that success isn’t just about bold ideas – it’s about staying in the same, trusting your gut, and cultivating a community that will support you (and vice versa) along the way. Whether you are just starting out, or several years into your career, her message is clear: take the risk, own your voice, and don’t wait for permission.
A heartfelt thank you to Milena Kozhin for her incredible support and dedication—this program would not have been possible without her vision, connections, and unwavering commitment.
