Editor’s Note: Entrepreneur’s “20 Questions” series features established, along with up-and-coming entrepreneurs and asks them a series of questions about what makes them tick, their everyday success strategies and advice they have for aspiring founders.
What if you could actually lead a life of extraordinary? You could have it all: the career, family and the balance to stay sane.
Jessica Dilullo Herrin, CEO and founder of jewelry company Stella & Dot, thinks you can. Her multimillion-dollar company not only offers women an online portal to trendy and affordable jewelry, scarves, clothing and more, but it also provides a flexible job opportunity. Acting as their own boss, women, or “stylists” sell the jewelry line through a number of different channels -- parties, online and one-on-one events -- and make a commission off the sales.
Now with more than 60,000 sellers and expanding outside of the jewelry vertical, Herrin’s hard work has finally paid off.
“This business was started in my living room, and I didn’t have a paycheck for six years,” she says.
The ambition to create such an opportunity was sparked after Herrin left her job to follow her husband as he began a new job in Texas and started building a family. Taking a middle-management job at Dell, she started to brainstorm a business model where women can have it all. Stella & Dot was born shortly after.
But before the days of Stella & Dot, Herrin had already launched a successful business: Weddingchannel.com.
The goal of the website was to offer everything in once place and make planning easier for the modern day bride. Once that became a success, Herrin felt her job was complete, and it was time to find a new venture.
With Stella & Dot now earning more than $300 million from the thousands of business owners in six countries, Herrin recently released a book, Find Your Extraordinary, which details her life, offers advice, secrets to success and depicts her business philosophy.
We caught up with Herrin and asked her 20 questions to figure out what makes her tick:
1. How do you start your day?
I start my day with two habits: meditation and exercise. I need strength in mind and body to be able to go do everything else my day requires, so I focus on self care. It’s like putting on my own oxygen mask. I know if I take care of myself then I’ll be able to take better care of everyone else.
2. How do you end your day?
I end the day tucking in my children, reading to them and spending time with them. Then I spend time with my husband before I go to sleep. I turn off all small devices and screens for at least a half an hour before I got to sleep.
3. What’s a book that changed your mind and why?
Positive Intelligence by Shirzad Chamine. It’s one of the knowledge sources that affirmed for me that a positive mind is a powerful thing -- not just for yourself but for your team and the people around you.
A positive mind isn’t something where you figure out how to have it and you’re set for good. It’s like personal hygiene; you’ve got to keep it up every day.
4. What’s a book you always recommend and why?
Again, I would say Positive Intelligence. In this book, he pulls together decades of research from to show people how to shift their negative thinking into empowering ways of thinking, acting and feeling. After I read it, I was convinced that Shirzad was the real deal, and his approach and techniques really worked.
The gist of positive psychology is this: The more you train your brain to be positive, the happier you feel. For me, this has translated into taking time to quiet my brain every day to recharge and refocus.
5. What’s a strategy to keep focused?
My business is rooted in a mission I really believe in and that’s the key to entrepreneurial venture.
Stella & Dot started mission first and created the flexibility for women fulfilling not only their financial needs but also helping build confidence. That is why I’m focused. Focus isn’t something you force yourself into.
6. When you were a kid what did you want to be when you grew up?
An entrepreneur. I’ve always been a person that looked around the world and saw the way I wanted things to be instead of the way they were. I had this irresistible desire to go change them, and I think entrepreneurs are change makers. They’re dreamers and doers.
7. What did you learn from the worst boss you ever had?
I’ve had so many. The first boss I had was my manager at Baskin Robbins. He told me I had to go on a date with him, and if I didn’t, he’d make me mop the floors. I quit. That first boss showed me that you have to stand up for yourself.
Being a women in business there’s been many times I needed to walk away from certain situations. I’ve learned what to do and what not to do.
8. Who has influenced you most when it comes to how you approach your work?
My father. I was raised by my dad who was a single dad and had the ultimate spirit of an entrepreneur. My father had a paper route since he was in the fourth grade to help put food on the table. He put himself through college, got a Master’s degree and has reinvented his career many times over as a home builder, a computer software and developer.He is always excited to be there, willing to work hard, never believed he needed a pedigree or validation to go do something. He just cracked a book and taught himself. That’s really something I learned from him.
9. What’s a trip that changed you?
Going to Nicaragua and building a school with the Stella and Dot Foundation. The most profound impact was the level of poverty. It was so much beyond what we experience in our daily life. We stayed with a local family, with nine people in one room and no dad.
We were joking at the job site because every single meal was beans and rice. So there you are, still joking and complaining about beans and rice, while you’re living with people who that feel so fortunate just to eat beans and rice. You look at yourself and realize how lucky you are.
Then, there was this one day when someone found an egg, and we were like “Oh my God, you found an egg! Where’d you get the eggs?” We all went looking throughout the village trying to find the egg. It never materialized. But it was a life lesson.
I live in a place that no matter what problems I have in business or in life, I open up my refrigerator here’s a dozen eggs. The reality is we are so fortunate. If you’re born in the United States, you’ve won the lottery.
10. What inspires you?
Making an impact on women in the workplace. We can talk about the obstacles women face in the workplace, but I also like to remind myself how we’ve won the lottery when we look at the women actually working and entering the workforce. I am so lucky to be here, and it's such a privilege to be in this place and time.
I can use my experience I've learned as an entrepreneur and continue to push forth women into the workplace, and hope they find true success -- success that brings them happiness.
11. What was your first business idea and what did you do with it?
My first idea for a company was an online wedding gift registry. The idea was actually a business school project I worked on along with my co-founder, Jenny Lefcourt. As we worked on the project, we realized we actually felt more passionate about pursuing our company than we did about pursuing business school. We decided to drop out of the MBA program to pursue our new venture. We called it Della & James, and it’s the company that eventually became WeddingChannel.com. After a long, winding road (that I think of as more valuable than an MBA would have been), we got funding, partnered with major players like Macy's and Crate & Barrel, and revolutionized the way people shop for and celebrate weddings. Later, we sold the company to the Knot for $90 million.
I am most proud that our original idea, the one that continues today as a strong part of the business, is a service that millions of people use and love. Not bad for a warm-up round.
12. What was an early job that taught you something important or useful?
I worked at a retail-clothing shop and would see how employees would stop working when the manager left. I would then compare it to other places where there were commissions for the salespeople and incentives for them to better the company. I learned how to train, treat and motivate employees.
13. What’s the best advice you ever took?
If I wanted to run a large company, I should go work at one. An adviser told me that after I left WeddingChannel, and I took a job at Dell. It ended up being critical for my personal growth. The experience taught me how to be a leader, not just as an entrepreneur.
14. What's the worst piece of advice you ever got?
Don’t drop out of business school. I did and had I not, I would’ve never started the company that led to all of this.
15. What’s a productivity tip you swear by?
Time block. I control my calendar, so other people don’t control it. I rigorously look at my calendar and make sure the most important things are getting done.
16. Is there an app or tool you use in a surprising way to get things done or stay on track?
I use the Sleep Well App, an app that helps sleep and insomnia through hypnosis, all the time to help me sleep and meditate before I go to bed.
17. What does work-life balance mean to you?
It means living your life in accordance with your values. I practice work-life integration and being what’s right in your life.
18. How do you prevent burnout?
I have a rigorous routine of self care and practice mental and physical fitness to be strong for my work. I take care of myself with exercise every day.
19. When you’re faced with a creativity block, what’s your strategy for innovating?
It’s the same thing. I go for a run. It puts me into a creative state. Everything that seems so complex suddenly clears.
20. What are you learning now?
The company’s growing, and this stage of the business is different. It requires different things, like internal talents development and corporate learning. We’re spending time learning, so we can make a system that’s right for the company and works more efficiently.