The elevator ride lasted 30 seconds. It changed Jessica Herrin's life, and eventually helped 50,000+ women build their own businesses.

What started with trunk shows in her living room grew into Stella & Dot, a platform that empowered women to build businesses on their own terms. If you've ever wondered how to turn passion into profit while staying true to your values, Jessica's reinvention story holds the blueprint. In today's newsletter, I'll share:

Enjoy this trunk story…LG

At 15, Jessica Herrin went to work. Not just for money, but for independence. Like many of us entrepreneur types, she felt the pull between playing it safe and betting on herself. Instead of buying trendy clothes, she invested $2,000 in a personalized children's book venture.

The returns were not life-changing, but the lesson was. She realized she loved putting her energy into things that could grow.

By the time she was in college, Jessica was looking at life through her father's lens: crack a book, learn it yourself, take control. That grit carried her from community college to Stanford University. In the 1990s, Silicon Valley was an explosion of possibility, and Jessica was in the middle of it.

The Silicon Valley Hustle

She landed roles at Trilogy in Austin, then Nielsen NetRatings in Santa Clara, where she led product marketing for a pioneer in internet measurement before Nielsen acquired it. But her ambition was already pulling her toward entrepreneurship.

In 1997, she enrolled in Stanford's MBA program. Within a year, she dropped out to co-found Della & James, which became WeddingChannel.com. Jessica and her co-founders raised capital from Kleiner Perkins, Amazon, and Federated, built an innovative gift registry platform, and eventually sold the business to The Knot.

On paper, she was a success. In reality, she was running 100-hour weeks and felt disconnected from her purpose.

The Oprah Moment

A few years into WeddingChannel, Jessica appeared on Oprah with her co-founder in a segment about passion and business. After the show, her inbox overflowed with messages from women asking, "How can I start my own business?"

Jessica did not have an answer she could stand behind. Her path required venture capital, round-the-clock work, and sacrifices that did not feel sustainable. If you've ever felt torn between ambition and authenticity, you know this feeling. It was not a roadmap she could recommend to a busy mom seeking flexibility. That disconnect stayed with her.

After selling the company, she did something unexpected: she joined Dell. A mentor had told her:

"If you want to run a large company, go work at one."

At Dell, she managed teams across sales, product, and e-commerce. It was the corporate education she had never received in Silicon Valley.

Still, the entrepreneurial itch did not fade. In 2003, pregnant with her first child, Jessica was already thinking about what she called the modern woman's dilemma: how to earn a livable income without sacrificing family and balance.

That question looped in her mind. How do I help these women?

The Elevator Epiphany

Then came the elevator ride that changed everything.

On a business trip to Dallas, Jessica stepped into an elevator full of Mary Kay consultants buzzing from their annual sales conference. Their joy was palpable. It was not just about the makeup they sold. It was about community, recognition, and the empowerment of owning a business.

As she later put it, the excitement was contagious, and the purpose was bigger than product. That is when it hit her.

"I could launch a social-selling company for women of my own generation, something more modern and hip. I decided to modernize flexible entrepreneurship with high style, high tech, and high touch. My vision was to create a new kind of company that would offer today's busy woman a career alternative.

"I wanted to help solve the modern woman's dilemma and democratize entrepreneurship."

Building the Dream in Her Living Room

She did not start with a product. She started with a purpose. Design a business that serves the independent owner first. Make it fit around life's rhythms instead of demanding everything. Give women the choice to set their hours, earn real money, and be proud of the brand they represent.

She began experimenting at home in Austin. Nights and weekends, while still at Dell and pregnant, she turned a room into a workshop filled with beads, clasps, and stones. She tested products, hosted trunk shows, and walked in the shoes of the very women she hoped to empower.

The Stella & Dot Revolution

She sought mentors with experience scaling direct sales, including a partner from Kleiner Perkins and the former CEO of Home Interiors & Gifts. She brought in a top jewelry designer to refine the product line and later partnered with Stanford alum Blythe Harris, who had launched Banana Republic's jewelry collection and became Chief Creative Officer.

Together, Jessica and Blythe renamed the company Stella & Dot, after their grandmothers. Stella represented Jessica's grit and drive. Dot represented Blythe's sense of style and creativity. The name honored the women who shaped them and symbolized the women they hoped to empower.

With Stella & Dot, Jessica reframed direct sales into social selling. Stylists did more than sell jewelry. They built relationships, asked about upcoming weddings, parties, and milestones, and helped women feel confident for those moments.

The starter kit cost $199 and came with $350 in jewelry, lowering the barrier to entrepreneurship. Stylists earned 25 to 30 percent commissions, plus team-based bonuses if they chose to recruit others.

The results were transformative. By combining high-quality fashion accessories with e-commerce, social media, and community-driven sales, Stella & Dot created a flexible platform that scaled quickly. Teachers used it for summer income. Lawyers sold part-time on weekends. Some stylists made a few hundred dollars a month. Top earners built six-figure businesses.

Jessica had cracked the code. She reinvented entrepreneurship for the modern woman. And she did it on her own terms.

She often describes Stella & Dot not just as a business, but as a culture. A place where success is defined not only by revenue, but by happiness and balance. A company designed so she could be both CEO and mom, wife and leader, without apology.

The business grew beyond her early expectations. By 2006, Stella & Dot had crossed $1 million in sales. Within a few years, it had empowered tens of thousands of independent business owners.

Today, more than 50,000 stylists have generated over $500 million in revenue, hosted hundreds of thousands of trunk shows across six countries, and contributed more than $10 million to charitable causes.

Jessica Herrin’s journey is stellar example of how founders can use story to inspire, attract, and scale. From creating a business rooted in her own needs, to rallying brand champions, to framing obstacles as opportunities, her approach shows how powerful storytelling can be as both a strategy and a mindset. Here are three lessons to take from her story.

A Dale Carnegie study found that engaged teams are 12% more productive, companies with high engagement outperform others by up to 202%, and strong culture slashes turnover. Jessica Herrin proved this with Stella & Dot by empowering stylists to feel connected and proud.

Storytelling was the key, it created emotional bonds that turned sellers into loyal ambassadors. When people feel part of the story, they work harder, stay longer, and spread the word.

In this video, Jessica Herrin at the Mass Women’s Conference, Jessica embodies the very lessons from her founder journey: knowing your audience, creating champions, and turning problems into solutions.

With passion and optimism, she shares how “naive optimism” fueled her persistence, how resilience carried her through constant obstacles, and how authenticity built emotional connection. A reminder that storytelling is not just about sharing success, but about showing the grit, hope, and humanity behind it.