Kerri at her flagship location in Westport, CT
Onstage, in conversation with Kerri Rosenthal, for Startup Westport’s inaugural Founder Series at the Content Studio of Westport, what unfolded was not just the story of an artist-turned-fashion designer, it was a masterclass in intentional growth.
Ten years ago, Kerri sold a single painting. Today, she leads a fully self-funded, multi category brand with 23 employees, national wholesale accounts, high-profile collaborations and a retail presence that includes Bloomingdale’s window displays. But what defines her success isn’t scale, it’s discipline.
Slow growth.
Smart growth.
Resilient growth.
Speaking candidly about the underbelly of entrepreneurship, the missteps, the bad hires, the pivots, the daily recalibrations, Kerri offered something rarer than inspiration: clarity. She has chosen to build without outside investors. She has chosen responsible expansion over rapid acceleration. And she has chosen to define success on her own terms.
Below, a refined look at our conversation.
Color meets the coast with KR Surfboards.
ON THE EARLY DAYS
Samantha Yanks: When you look back at the beginning, what did you understand about building a business — and what did you have to learn the hard way?
Kerri Rosenthal: In the beginning, I didn’t think of it as building a “business.” I was just making work and putting it out into the world. But once people started responding, I had to shift from artist to operator. That’s where the real education began.
The hardest lessons came through people. Hiring too quickly. Hiring out of urgency instead of alignment. I’ve had bad hires that cost time, money, and energy, but each one clarified what I value in a team. Culture matters. Integrity matters. Accountability matters. You can’t scale without them.
ON GROWTH WITHOUT INVESTORS
SY: You’ve built this brand without outside investment. Why was that important to you?
KR: Control. Longevity. Peace of mind.
When you take investors, you take on timelines that may not align with your own. I wanted the freedom to grow at a pace that felt sustainable, not explosive. I didn’t want to chase growth for optics. I wanted to build something I could keep.
Being self-funded forces discipline. You think carefully. You don’t overextend. You grow when the infrastructure can support it.
Art lives in every detail throughout the KR Flagship.
ON WHOLESALE AND BIG PARTNERSHIPS
SY: Your brand has expanded into major wholesale accounts and collaborations. How do you approach those opportunities?
KR: Responsibly.
It’s exciting to see your work in a larger arena but every partnership carries responsibility. You’re not just producing more product; you’re protecting your brand.
I ask: Does this align with who we are? Can we execute it well? Will it stretch us in a healthy way, or strain us?
If the answer isn’t clear, we wait.
ON DAILY PIVOTS
SY: What does entrepreneurship really look like behind the scenes?
KR: It’s constant recalibration.
Every day is a pivot. Something doesn’t arrive on time. A launch underperforms. A design resonates unexpectedly. You adjust. You learn. You keep moving.
There’s no straight line. Anyone who says there is isn’t being honest.
Layers of creativity and color through mini works of art. credits, Kyle Norton
ON KNOWING THE CUSTOMER
SY: What has been the through-line over the last decade?
KR: I know my customer.
I understand what she responds to, emotionally and visually. That clarity makes decisions easier. When you deeply understand who you’re speaking to, you don’t chase every trend. You refine your voice instead.
ON DEFINING SUCCESS
SY: Ten years in, how do you define success now?
KR: Sustainability. A strong team. Creative freedom.
Of course growth matters. Revenue matters. But I’m proud that we’ve built a company with 23 employees, real people whose livelihoods are tied to this brand, and we’ve done it thoughtfully.
Success is building something that lasts. Something you still want to show up for every day.
Kerri Rosenthal’s story is not about overnight scale or viral moments. It’s about measured expansion, creative conviction and the courage to say no.
In a landscape obsessed with speed, her approach feels almost radical.
Ten years in, and building for the long game.
181 Main St, Westport, CT
IG: @kerri.rosenthal