How I Did It: Jessica Herrin, CEO and Founder of Stella & Dot

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I had the chance to chat with Jessica Herrin, a mother of two and founder/CEO of Stella & Dot, a socially based boutique jewelry and accessory sales company.

Herrin has sought to help reinvent and redefine the merchandising industry in a way that helps the modern woman balance life and work. Stella & Dot offers an exclusive line of independent artisan made accessories for women through their online store and in-home Trunk Shows.

Stella & Dot’s Trunk Shows provide a unique opportunity for women to create a flexible work schedule.

In this Q&A, Jessica reflects on how her vision matches up with her reality and the risk she took creating a business model where work-life balance is the driving factor of her success. How did you get the business started?

Jessica Herrin: I launched Stella & Dot out of my living room when I was inspired to reinvent what flexible entrepreneurship could look like for the modern woman, who wanted an alternative to the one career ladder at a 9-5. My mission was to think differently about how success could mean not only financial reward, but also happiness. Flexibility felt really key to what that looked like to me as a woman since, let’s face it, we’re the first on call with the ebb and flows. We have to have time to take care of the other aspects of life. Does your reality match up with your vision?

Jessica Herrin: What’s interesting is that I never wanted to pursue “part-time”. I wanted to pursue passion and worth. From that perspective it’s absolutely aligned with what I had hoped for. For me working full-time and even very full time, as a founder and CEO, means that I work on my terms and that makes all the difference.

I can decide we don’t have meetings at Stella & Dot at 6pm because that’s when everybody is home with their families. If I’ve been traveling for a week, then I come in a little later the next week. I set the culture and that culture is inherently aligned with my values. It’s something that let’s me be the wife and mother I want to be and the CEO at the same time. Is that a freedom you afford your employees as well?

Jessica Herrin: It is and it’s something I’m very passionate about. It would be really inauthentic to create flexibility for women on the outside and not do it on the inside. That being said it’s not always easy, but it’s worth it. I just got a message from my VP of strategy who just landed in Uganda on a sabbatical, spending the next eight weeks there to have a life adventure with her family. It’s not that it’s easy for us as a company to have people missing for that long, but the reality is that you have to understand what your true choices are. If you don’t allow people to live their best life they’ll opt out, and you’ll lose their talent for good.

I would rather compromise and find a way to make it work. I have found that internally people are so aligned with our mission that they’re at the ready to step in, be flexible, be agile and fill in for whoever needs flexibility in that moment. We’re all proud to be part of a company that thinks and acts that way. What was the most useful mistake you made starting your business?

Jessica Herrin: It’s hard to pick just one because I do believe that all extraordinary businesses involve sticking with something through all the many mistakes that happen every single day.

For me I would say our line of DIY jewelry was a mistake. When we started, Stella & Dot offered artisan made jewelry and a do-it-yourself customizable line. Ultimately the offering of choice was too much complexity for our business to handle and we had to narrow in on our focus. One could say that’s a mistake, but the byproduct was that I became an expert at jewelry making and production. So now I look at a complex piece of jewelry and say this needs half-hard wire because it will be stronger. My previous experience as a general manager gave me a handle in other areas, but in production, merchandizing and design my knowledge was lighter. Through this mistake I gained much greater depth and expertise in areas where I needed I hadn’t had as much experience. What is the mission statement/mantra that inspires you?

Jessica Herrin: There was a moment when I was deciding whether or not I was going to go out on my own and attempt to reinvent an industry. Which was daunting and crazy at the time, frankly. We had moved to Texas and I was working at Dell in their e-commerce department trying to broaden my experience as an executive. It seemed like such a different path, even though I had been an entrepreneur, to do something that was in independent sales.

I remember there was a sign on a friend’s cubicle with a Cecil Beaton quote that said, “Be daring, be different, be impractical; be anything that will assert integrity of purpose and imaginative vision against the play-it-safers, the creatures of the commonplace, the slaves of the ordinary.” I remember staring at that and thinking I will not be a ‘slave of the ordinary’. I want to be daring. I want to be different, even if it’s impractical. I want to do anything to assert the integrity of my vision. That was my early mantra to start the company. How do you find balance juggling all areas of your life?

Jessica Herrin: Time mastery is the key to living the life you want. No one who has ever done great things with their life has ever had more than twenty-four hours in a day. It’s simply a matter of how you choose to use them that determines the quality of your life. We all have the same scarce resource of time. What are a few tips you learned along the way?

Jessica Herrin: First of all, I think you have to understand what matters to you most and then make sure that you’re aligning your life and living it in accordance with your values. Time management is about asking yourself what matters and what does not. It’s a choice. You can’t try to do everything and have everything and be everything to everybody at all times. If you pursue that you’ll end up not being great at much and not having a deep meaningful anything. It’s about understanding and prioritizing your priorities and picking what really matters. It involves asking yourself those big questions.

Secondly, I look at the first hour of my day as a compass. I plan, reflect and determine what is going to be the best use of my time and serve my purpose. What am I going to do today?

Each day should start with some quiet reflection on ‘what do I need to get done?’ It helps make sure that you’re not squandering your time. Time enjoyed is not time wasted. I’m not advocating that every minute of your day be filled with some highly efficient activity, it just means that you should be mindful and set a course of action. Even if you’re allocating two hours a day to look at Pinterest because that restores creative energy, just understand that maybe if you chose to do an hour of Pinterest, then 30 minutes at the gym, and 30 minutes of work, you might be in a better place. I think tracking what you do with your time helps heighten your awareness.

Lastly I think it’s about learning to say ‘no’, especially for women. We are inherently pleasers and often times we don’t know how to say ‘no’ to other people and our time ends up getting away from us. It’s hard to do that because you want to say ‘yes’ to everything. I decided to only do school volunteer things in which my kids are physically present because I know I’m serving both purposes, volunteering for my community and spending time with my kids. With a full time job, I have to feel okay with the fact I’m not going to be the one to organize the class gift. I can’t feel guilty about it, but have to accept that these are my choices and be okay with it.

Everybody is juggling—there will always be more to do than can be done. The art is not to keep all the balls in the air, but to determine which ones are rubber and which ones are glass. If you learn to live comfortably and happy with things undone—as long as they’re rubber—you’ll be in good shape.


Stella & Dot CEO and Founder Jessica Herrin has proven just how one woman can go about styling her life with smarts, courage, and tenacity. After joining two successful tech startups out of college, she went to the Stanford Graduate School of Business, where, at the ripe age of 24, she co-founded the now world’s leading wedding site, Jessica’s been recognized for her business savvy even more than her style savvy – Oprah, The Wall Street Journal, New York Times and Forbes have saluted her for her vision. Taking Social Selling to the next level, Jessica’s been honored by Ernst & Young and Inc. 500 as a Top Entrepreneur. But Jessica is most proud of the recognition she gets from the women of Stella & Dot, who are mirroring her success in reinventing the home business opportunity for the modern woman. Because, as Jessica claims, “nine-to-five just doesn’t flatter.”

About the Author

author image in-house editor & writer, Daniel Jenks, hopes to inspire positive change in males, millennials, and anyone trying to make the world a better place to live. He is currently based in Los Angeles, CA.

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