Achieve Your Goals with Hal Elrod
Episode 575: How to Go From Broke to a $100 Million With Rebecca Minkoff
Date: February 26, 2025
Episode Overview
In this episode, Hal Elrod sits down with renowned fashion designer, entrepreneur, and author Rebecca Minkoff. The conversation traces Rebecca’s remarkable journey from being broke and in debt to building a $100 million fashion brand—then losing 70% of it during the pandemic, only to rebuild and refocus on what matters most. The discussion explores grit, fearlessness, business pivots, the realities of entrepreneurship, and the importance of defining success beyond profit. Rebecca also talks about her updated book, Fearless: The New Rules for Unlocking Creativity, Courage, and Success, her brief stint on The Real Housewives of New York, and actionable advice for aspiring founders.
Key Discussion Points & Insights
Early Failures, Crucial Turning Points, and the Birth of a Brand
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Facing Failure and Family Support
- Rebecca recounts struggling to make her first clothing line profitable, and going to her father in 2004 for help—asking for both advice and money. Her father refuses more financial support and suggests she call her brother Yuri for help. This pivotal moment leads her brother to join the business, marking the beginnings of the Rebecca Minkoff brand (05:48–06:35).
“He said, call your brother. He might be able to help you and streamline your finances... That was kind of the beginning of today, what we call the Rebecca Minkoff brand, because my brother…signed on board.”
—Rebecca Minkoff (06:13)
- Rebecca recounts struggling to make her first clothing line profitable, and going to her father in 2004 for help—asking for both advice and money. Her father refuses more financial support and suggests she call her brother Yuri for help. This pivotal moment leads her brother to join the business, marking the beginnings of the Rebecca Minkoff brand (05:48–06:35).
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The Breakthrough with the Morning After Bag
- Struggling as a clothing designer, Rebecca creates a handbag (the "Morning After Bag") upon request from an actress for a film. The design, price, and name, combined with a pivotal feature in the Daily Candy email newsletter, lead to a wildfire of demand.
“It was just this powerful moment of right style, right price, right story, and it just—it flew.”
—Rebecca Minkoff (08:37)
- Struggling as a clothing designer, Rebecca creates a handbag (the "Morning After Bag") upon request from an actress for a film. The design, price, and name, combined with a pivotal feature in the Daily Candy email newsletter, lead to a wildfire of demand.
Growth, Adapting to Industry Trends, and Scaling Challenges
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Transition to Accessories and Scaling Challenges
- By the second year working with her brother, the company pivots away from clothing to focus solely on bags, riding the wave of initial success. The relentless pressure to create more new products ramps up with the rise of social media and e-commerce (10:15–11:13).
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Rapid Growth and the Profitability Trap
- Pre-COVID, Rebecca Minkoff is a $100 million business, but with thin or nonexistent profits—reflecting a then-popular industry mindset of “growth over profit.”
“I know what it’s like to be at over 100 million and not making money, and I’d rather be half of that and, like, okay, we’re making a profit.”
—Rebecca Minkoff (11:56)
- Pre-COVID, Rebecca Minkoff is a $100 million business, but with thin or nonexistent profits—reflecting a then-popular industry mindset of “growth over profit.”
Pandemic Crisis, Relentless Change, and Letting Go
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COVID-19: Sudden Collapse and Survival Mode
- In March 2020, every major retailer cancels orders, vaporizing 70% of their business virtually overnight. Rebecca opens up about lay-offs, deep pay cuts (she and her brother take 30% less), and surviving day-to-day.
“Every morning was, what did the website do yesterday? Okay, what do we think it’s going to do tomorrow?... The easy thing to do would have been to go out of business... The hard thing was, alright, let’s give it our all and go down in flames if that’s what’s going to happen.”
—Rebecca Minkoff (14:05)
- In March 2020, every major retailer cancels orders, vaporizing 70% of their business virtually overnight. Rebecca opens up about lay-offs, deep pay cuts (she and her brother take 30% less), and surviving day-to-day.
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Supply Chain Woes and Selling the Company
- Post-pandemic, severe supply chain shortages prevent them from producing inventory, triggering anxiety with their bank. In 2022, they sell almost the entire business to a strategic partner, keeping only a small equity stake. Rebecca remains as a paid employee.
“You survived COVID and then you’re like, oh great now supply chain issues are hitting us...”
—Rebecca Minkoff (16:21)
- Post-pandemic, severe supply chain shortages prevent them from producing inventory, triggering anxiety with their bank. In 2022, they sell almost the entire business to a strategic partner, keeping only a small equity stake. Rebecca remains as a paid employee.
Realities of Entrepreneurship
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Unpredictability and Facing Problems with Resilience
- Rebecca is candid about constant business drama and her practiced calm in the face of adversity:
“Someone’s like, you’re so calm. And I’m like, that’s because I’ve been through this like a million times. The only thing I know how to do is attempt to solve the problem.”
—Rebecca Minkoff (18:20)
- Rebecca is candid about constant business drama and her practiced calm in the face of adversity:
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Redefining Success and Mental Health
- Hal and Rebecca discuss detaching emotional well-being from business outcomes and finding joy in the present, amidst chaos or calm.
Fearless: The Book & The Mission
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Purpose and Lessons of ‘Fearless’
- Rebecca’s book, Fearless, was written by applying tested principles both when building and rebuilding her company—expanded in the new edition to explicitly address women and money.
“What is something I could add that I feel like women need—and they need to be talking about money... What did you invest in recently that paid you good dividends? Do you need life insurance?... Conversations that women definitely don’t have.”
—Rebecca Minkoff (21:07)
- Rebecca’s book, Fearless, was written by applying tested principles both when building and rebuilding her company—expanded in the new edition to explicitly address women and money.
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Core Rules and Message
- The book features 22 rules for unlocking creativity and courage, aimed at anyone (not just women) paralyzed by fear or big decisions. Real dangers today are rare; what stops us is fear masquerading as danger.
“These...are not rules that help you overcome the fear. It’s almost like, yeah, I have it, but I’m going to do it anyways.”
—Rebecca Minkoff (23:54)
- The book features 22 rules for unlocking creativity and courage, aimed at anyone (not just women) paralyzed by fear or big decisions. Real dangers today are rare; what stops us is fear masquerading as danger.
Family, Balance, and the Meaning of Success
- Life as a Mother of Four and Authenticity
- Rebecca emphasizes how her definition of success has shifted from business metrics to being mentally present with her family.
“If I’m with my kids, am I able to be present? And if I am, to me, that’s successful.”
—Rebecca Minkoff (32:21)
- Rebecca emphasizes how her definition of success has shifted from business metrics to being mentally present with her family.
The ‘Real Housewives’ Experiment
- Taking a Risk and Staying Authentic
- Rebecca takes a calculated risk by joining The Real Housewives of New York to connect with her core consumer but quickly discovers the show prioritizes drama over authenticity and opts not to return.
“I just committed to being me, and I was punished for it. So to answer your last question, I’m definitely not going back, because it wasn’t what I agreed to do.”
—Rebecca Minkoff (26:41) - She also critiques media distortions:
“A story I would tell that I thought was funny would be twisted by the media to be, like, weird or salacious... Oh, I will never believe a headline about anyone ever again.”
—Rebecca Minkoff (28:20)
- Rebecca takes a calculated risk by joining The Real Housewives of New York to connect with her core consumer but quickly discovers the show prioritizes drama over authenticity and opts not to return.
Hard-Earned Advice for Entrepreneurs
- What It Really Takes
- Rebecca cautions founders to love what they do so much that they’d persist even through relentless setbacks; recalibrate expectations for slow, sustainable growth; and value life balance over chasing massive exits.
“Not everyone needs to be a billion dollar company or a hundred million dollar company... What is wrong with a profitable, smaller, slower-growing business that provides for you and your family and a life that you want?”
—Rebecca Minkoff (30:24) - Hal adds the “fisherman parable” to underscore the importance of knowing what you’re actually working for in life (31:18–32:04).
- Rebecca cautions founders to love what they do so much that they’d persist even through relentless setbacks; recalibrate expectations for slow, sustainable growth; and value life balance over chasing massive exits.
Memorable Quotes
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On Persevering Through Hardship:
“The hard thing to do was, like, all right, let’s give it our all and go down in flames if that’s what's going to happen. Like, we owe it to ourselves. We’ve been in business for 15 years. We owe it to the team we have left.”
—Rebecca Minkoff (14:05) -
On Profit vs. Growth:
“We lost about 70% of our business during COVID... I know what it’s like to be at over 100 million and not making money, and I’d rather be half of that and, like, okay, we’re making a profit.”
—Rebecca Minkoff (11:35–11:56) -
On Staying Authentic in Media:
“I just committed to being me, and I was punished for it...I’m gonna be me. And if I’m penalized for it, that’s an energy and a values I don’t like.”
—Rebecca Minkoff (26:41) -
On Success and Presence:
“If I’m with my kids, am I able to be present? And if I am, to me, that's successful.”
—Rebecca Minkoff (32:21)
Notable Segments & Timestamps
- Introduction & Rebecca’s Backstory: (00:36–05:48)
- The Turning Point: Brother’s Involvement & 'Morning After Bag': (05:48–09:24)
- Dealing with Rapid Growth and Industry Changes: (09:51–11:46)
- COVID Collapse and Surviving as a Founder: (13:31–16:21)
- Selling the Business & Moving On: (16:21–18:20)
- Entrepreneurship Real Talk & Emotional Resilience: (18:20–19:30)
- About ‘Fearless’ and Financial Empowerment for Women: (20:02–23:54)
- Rebecca's Personal Life and Shifting Definition of Success: (21:30–22:28, 32:21–32:58)
- Real Housewives Experience: (24:18–28:19)
- Advice for Entrepreneurs & Redefining Ambition: (29:43–32:04)
- Defining Legacy and Closing Thoughts: (32:04–34:43)
- How to Find Rebecca & Her Work: (33:29–34:34)
Connect and Learn More
- Buy Fearless: The New Rules for Unlocking Creativity, Courage and Success wherever books are sold (Amazon, Barnes & Noble, Target, etc.).
- Follow Rebecca on Instagram: @beckyminkoff
- Listen to her podcast: Super Women with Rebecca Minkoff
- Find her company: Rebecca Minkoff
This episode is both a candid look at business highs and lows, and a guide to resilience and authenticity. Rebecca’s journey is a testament to daring, adaptation, and holding onto what matters—valuable lessons for goal-achievers everywhere.