C-Suite to Main Street: A Masterclass in Leading with Fearless Vision

Every entrepreneur comes face-to-face with fear during their business journey, whether it’s the fear of failure, the fear of making the wrong call, or the fear of losing what they’ve built. In these moments, the key to moving forward is staying true to your values and finding courage in the face of high-pressure situations. 

In this installment of CO—’s C-Suite to Main Street series, Vice President and Editor-in-Chief Jeanette Mulvey sat down with renowned fashion entrepreneur Rebecca Minkoff, author of “Fearless,” and Co-Founder of the Female Founder Collective, to discuss what it really looks like to lead and make decisions with fearless vision.

Start with values alignment

Minkoff’s decades-long career has been defined by taking chances and knowing where to draw lines. Every business owner has to make some compromises along the way, but when a certain path clashes with your identity and values, your decision should be non-negotiable. 

Minkoff recalled pushing back when a major retailer wanted a laptop case printed with “nerd alert,” which she felt carried the wrong message. 

“[I said], ‘To me, we all need a computer and that’s [a] negative connotation … [so] I’m not doing it,’” she told CO—. 

The decision was overridden, but ultimately, Minkoff’s instinct was right and the product didn’t sell. The lesson? 

“When no means no … I'm really firm on that and I hold to it,” she said. “I make sure it doesn't happen.”

[Read more: How Reflecting on Purpose and Values Benefits Small Business Owners] 

Don’t confuse big numbers with success

Minkoff said the real work of growing a successful business is operational discipline, especially around profitability. She admitted that, despite earning $115 million a year and having products in 900 retail stores at its height, the company was actually losing money.

“It looks like a big success to have a big old number … but … the stress of [losing money] takes away all the joy of being able to [say], ‘Woo, a hundred million!’” said Minkoff.

That perspective shaped a major strategic shift: intentionally shrinking the business down to about $70 million by cutting low-margin channels and reducing sales. The result was a healthier business built for profit, not artificial success based on numbers.

When COVID hit in 2020, Minkoff’s wholesale department store orders were all canceled, and the business shrank again to just direct-to-consumer e-commerce sales. Now, instead of obsessing over what big retailers wanted the brand to produce, the team could focus on what their actual customers wanted. 

“We got so close to our customer and we knew what she wanted,” she said, whether that meant Zoom-friendly elevated sweatshirts or jewelry that fit a new lifestyle. 

“We were becoming beholden to all these places,” Minkoff added. “When the noise goes away and you go, ‘What are we to the customer? What are we as a brand standing for?’ — it’s such a point of strength, and that will lead you down the right path.”

[Read more: How to Predict and Meet Modern Customer Expectations] 

Redefine your ‘worst case’ scenario

For Minkoff, fearlessness isn’t about never being scared; it’s about redefining what “worst case” actually means. She described a turning point when, during a celebration dinner in Paris, she received a message that the bank might foreclose on her company. 

While this might seem like the worst thing that could happen to an entrepreneur, Minkoff had a sudden realization in that moment: Even if her company fails, the bank couldn’t take her family away from her, and she could start her career over with something new.

“From that moment on, I felt very free in approaching risk because to me, the worst thing that could happen is losing my family; everything else is figureoutable,” she said. “That has remained a stable pillar for me to this day.”

That same realism shows up in how she thinks about quitting or pivoting: “If you are no longer passionate about it and it does not bring you joy and it brings you stress … it’s not worth it,” she said. 

But she also rejected the simplistic advice to only follow your passion. Sometimes something can be worth continuing because it funds stability or future options. 

“We are businesses and we do have realities,” said Minkoff, advising entrepreneurs to try to find the “middle ground” between walking away and pushing forward for the sake of it. 

“[Ask yourself], ‘Why did I start this? What was I trying to get out of it and how do I get that flame back?’” she said. “That's always a good way to see if you can get that passion back for it.”

Ultimately, Minkoff’s version of fearless vision is grounded, not flashy: do the work, protect what’s core to your brand’s values, and don’t let outside validation define success.

CO— aims to bring you inspiration from leading respected experts. However, before making any business decision, you should consult a professional who can advise you based on your individual situation.