I’m so excited to share this conversation with you because today, we’re diving deep into the rebrand of Entreprenista—and not just the pretty new visuals. We’re talking about the messy, real, behind-the-scenes journey with cofounder Stephanie Cartin, and how it all came together. If you’ve ever wondered whether a rebrand is “worth it,” this episode is for you.
Stephanie joined me to share how they knew it was time to level up the brand, even though everything was already working. Because sometimes? Good isn’t enough when your brand no longer reflects the power of what you’ve built.
Stephanie is the cofounder of Entreprenista—a media company and thriving membership community dedicated to helping women founders and leaders grow, scale, and actually enjoy building their businesses. And she’s right, we’d just been chatting about how hard it is to build a business without sleep, without support, and without a crew of fellow founders to lean on. That’s what Entreprenista is all about.
So naturally, I had to ask: if everything was going great, why go through the effort of a full rebrand?
Stephanie explained that the idea to rebrand wasn’t sudden—they always knew investing in the brand would be necessary. But like a lot of us, she and her cofounder Courtney took the “just get started” approach at the beginning. When Entreprenista first launched, it was only a podcast. They quickly threw together a logo and got moving, using their internal Socialfly team to help. At the time, there wasn’t deep strategy or meaning behind the branding. It was about speed and scrappiness.
Growing the Entreprenista Vision
Eventually, Courtney stayed focused on Socialfly (which they sold last year), and Stephanie began building Entreprenista into a full-fledged business and community. At that point, she was still flying solo, focused on delivering value to members, not building a full brand identity. “Design’s not my area of expertise,” she told me. “I always bring on other people to do that.”
Looking back, she said she wishes she’d invested in branding sooner—but she also knows that if she’d waited until it was “perfect,” they might’ve never launched. And honestly, I totally agree. People often ask me when they need a logo or website, and I’m always like, listen, I know I’m a designer, but you do not need those things to launch. Get started. Then build.
That said, once they did rebrand, the impact was huge.
Timing The Rebrand Right
Stephanie said it was a major undertaking. When Jesse, their head of marketing and creative, joined in 2023, she had all these ideas for refreshing the brand. But they were in the middle of planning their big awards event, and rebranding just wasn’t possible yet. So they created a roadmap for the right timing. When they finally tackled it, they had years of feedback and community growth to guide the process—and it all clicked.
What I loved hearing was how intentional they were about planning it out. I’ve worked with so many clients who try to squeeze a rebrand in during a move or while finishing a certification—and they’re always overwhelmed. Stephanie’s team thought ahead: what’s on our plate, what’s coming up, and how can we actually give this project the attention it deserves?
At the same time, Stephanie admitted she was often the bottleneck. “I just wanted to change one thing. Or tweak a color. Or swap a font.” (Yep—relatable.) But she also said her strength is taking things from good to great. Her team is insanely talented, and the final touches she added made it feel like something she could be proud of for years to come.
I asked her if anything carried over from the old brand, and she said yes—especially their focus on showcasing the community. That’s always been central to Entreprenista. The content, the imagery, the messaging—it’s never been about Stephanie or Courtney. It’s about the women in the community. They wanted a brand that made them shine.
They also didn’t completely throw out the old logo. They gave it a facelift, added supporting colors to make things pop, and kept the brand recognizable while elevating it to reflect where Entreprenista is now.
It’s Never Just a Logo
Of course, the process wasn’t without its challenges. Stephanie talked about how overwhelming it was to update everything: emails, social templates, headers, forms, merch, you name it. Jesse made a master checklist to prioritize what needed to be updated right away versus what could wait—and that helped them keep moving without panicking. “Not everything has to be done on day one,” Stephanie reminded me. “This is an evolution.”
(And yes, if you’re in this process too, I do have a rebrand checklist—it’s linked in the show notes.)
We both laughed about how things slip through the cracks—like how I updated my brand last year, but only noticed a Stripe link still had my old colors when I logged in months later. Priorities, right?
When I asked what part of the rebrand she’s most proud of, Stephanie lit up. She told me she gets chills every time she looks at the website or Instagram. “It’s everything I dreamed our brand could be,” she said. Not just because it looks good, but because it finally reflects the energy, talent, and vibrance of the community they’ve built. Now, when members are featured, they’re excited to share it. Brand partners are impressed. And Stephanie? She’s genuinely proud to share it every day.
Built for the Entreprenista Community
What really stood out to me was how member feedback shaped not just the visuals, but the actual structure of the new site. They built features the community had been asking for—like the Entreprenista Approved marketplace, where members can be featured and booked directly, and the Expert Council, which gives members a platform to publish thought leadership content.
These additions weren’t just icing on the cake. They were solutions to real needs their members had voiced—and a powerful way to make the rebrand feel like a true upgrade across the board.
Advice for Your Own Rebrand
So, of course, I had to ask: what advice does Stephanie have for others thinking about a rebrand?
Her answer: start with the why. Don’t just do it because you’re tired of your logo or want something “prettier.” Know what you’re trying to accomplish. Are you repositioning your brand? Reaching a new audience? Launching new offers? Your “why” will keep you grounded when the process starts to feel overwhelming (and it will).
This whole convo was such a fun and inspiring reminder that branding isn’t just about aesthetics—it’s about creating something that reflects the impact you’re already making. And when your brand finally feels like your business? That’s when the magic happens.
Where to Learn More
You can check out the full rebrand at entreprenista.com, and if you want to join the community, I’ve got a special $500 off code for you! Just use “JESSCREATIVES” 🙂
Thanks again to Stephanie for being such an open book about the process—and for building a brand that lifts so many other women up along the way.
