At POSSIBLE 2025, Bobbi Brown took the stage not as a legacy name, but as a modern founder still building. While most in the audience knew her as the creator of a billion-dollar beauty brand, this conversation led by 3C Ventures CEO Michael Kassan offered something more: a live masterclass on how to evolve, stay relevant, and scale with purpose.

Now five years into her second brand, Jones Road, and with a growing business portfolio that includes wellness products, a hotel, and content studios, Brown isn’t just maintaining relevance, she’s redefining it.

Before building product, Brown built clarity about what she believed, how she wanted to make people feel, and how she’d show up. That clarity has powered both of her brands.

Authenticity wasn’t a differentiator. It was the product. Whether she was teaching on The Today Show or launching Miracle Balm on TikTok, the message stayed consistent: makeup should enhance what’s already there, not cover it up.

She learned early that when she showed up as herself not as the idealized version she thought she should be things clicked. That idea informed every decision, from hiring to product development to how she trains store staff today.

When Brown exited her first brand, she faced a four-and-a-half-year non-compete. Instead of sitting still, she counted down. The moment that restriction lifted, October 2020, she launched Jones Road. The decision, she admitted, went against conventional wisdom. It was a week before the U.S. election, the middle of a pandemic. Everyone told her to wait. She did it anyway.

That instinct, honed over decades, allowed her to build with speed and precision. Jones Road didn’t follow traditional beauty distribution. It launched DTC. No department stores. No planograms. Full control over customer experience and creative. Five years in, it’s grown from ecomm-first to a physical presence, including ten retail locations and international demand.

Brown is clear about her culture. She hires people she enjoys working with. People who don’t flinch when she says she doesn’t like something. People who care more about the mission than the title.

That culture extends to the retail floor. At Jones Road stores, the expectation is simple: the team must be warm, kind, and honest. They teach, not sell. They help customers find lip colors that match their lips. Blush that mirrors their real cheeks. Simplicity over spin.

It’s a people-first approach that scales only when values stay tight and teams are built to reflect them.

Brown doesn’t see TikTok or Instagram as ad platforms. She sees them as education channels. Her goal isn’t virality, it’s clarity. When customers didn’t understand how to use her top product, Miracle Balm, she didn’t rewrite the packaging. She shot a video. It went viral, but more importantly, it helped people get it.

This was the same playbook she used on QVC and The Today Show not to sell, but to teach. That mindset is what makes Jones Road’s content stand out in a sea of trends: it doesn’t try to entertain. It tries to help.

When Kassan asked how Brown stays creative, she offered the most honest answer of the day: she gets bored easily. So she keeps trying new things.

From launching a content studio to building a hotel to publishing her tenth book, Brown doesn’t claim to have a master plan. She just follows her instincts and makes room for new ideas to take root.

Importantly, she doesn’t fear failure. When something doesn’t work, she pivots. And she hires people around her who are okay with that ambiguity because it’s where the magic happens.

The session ended with a reflection on impact. Brown’s proudest moments aren’t the launches or the valuations. They’re the comments from women who said her teenage beauty book helped them accept their freckles. Or that her tutorial helped them wear makeup for the first time in years.

Those are the stories that last. And those are the stories that define brand equity, not just for a quarter, but for a generation.

Independently Created. Not affiliated with POSSIBLE.

ClickZ is a ClickZ Media publication in the Events division