Create & Cultivate 100: Entrepreneur: Lisa Sugar

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Lisa Sugar is as OG as a digital pop culture trailblazer can be.

As founder and president of POPSUGAR, the eponymous global media empire she started with her husband “when social media wasn’t a thing and the iPhone wasn’t invented yet,” Sugar oversees the business side of company she built from the ground up.

With a global audience of over 400 million and 3.1 billion views, POPSUGAR is an addictive information destination for the digital generation, spanning entertainment, fashion, beauty, fitness, food and parenting. “I took a risk and started something completely different on my own,” says the former ad exec, noting that managing excel spreadsheets and budgets were not her calling.

For more on how this internet maven made it, read on below.

Name: Lisa Sugar

Instagram: @lisapopsugar

You were an internet trailblazer. A pop culture digital pioneer. What was it like in the early days?

It was a blur of writing, writing, writing — digging for the next story and writing some more. I became so addicted to how fast I could write and finding something first. I had to force myself to take breaks. I also knew I needed to stay in touch with my readers to maintain momentum and I was addicted to the feedback and the thrill of cultivating an engaged community. We spent so much time in the comments and creating forums for our most passionate and active users. Everything was so new and there was no playbook yet!

We had to test and try new things all the time and figure out what our audience responded to the most and do more of it. We had such an amazing time finding stellar talent. There are so many creative people who are passionate about learning more about their fields and becoming experts. I also loved partnering with similar sites and working together in ways that were considered totally taboo by traditional companies. We had to exude our passion for what we were creating at POPSUGAR so investors, employees or partners would feel confident and take the risk to work with us! Oh, I also had my first daughter, Katie, in the midst of the first year launching POPSUGAR. It was a family affair — I started the company with my husband, Brian, and some very close friends joined us early on. We were such a tight group — we still are. Katie was born literally on our first official day of team training. Those first few years, she was in the office with us every day. POPSUGAR was a creative explosion we were all caught up in.

What from your past prepared for such a massive undertaking?

So many experiences from growing up prepared me to become a leader. Most impactful was seeing how much my father loved his job and how well he treated every person in his office. He greeted the mail room attendees, the receptionists and his assistants with the same smiles, hugs or handshakes as he did his partners or his own bosses. I loved seeing that. I was an avid soccer player growing up and loved team sports. I learned not only to play at the top of your game but also how crucial it is to encourage others and to collaborate. I also married young and moved across the country three months after to a place where I knew no one but my husband. Starting life over was a challenge. Not only did I make new friends that are like family, but I was also able to get my self-confidence strong enough to take a risk to start POPSUGAR with Brian. We became a husband-wife team who could tackle anything together.

Did you have a feeling it would be huge?

I had a feeling we were on to something when I saw the audience grow so quickly. Within a year of starting POPSUGAR, I had 1 million readers, and that felt incredible! That said, if you had told me when we started that I was founding a company with 360 employees and a global audience of 300M, I’m not sure I would have believed you ;)

What are the common challenges you've seen among female business owners and entrepreneurs?

Being an entrepreneur is extra challenging for a woman, so it’s important to not go at it alone. In my case, I built POPSUGAR with my husband, Brian, but for others just starting, it’s about finding support through a community that includes anyone you think may be helpful. Don’t be afraid to ask for help, recommendations and connections from those you think would be interested or helpful. Another obvious challenge is the everyday juggle of family and work. When you find a job you love so much, you want to spend time investing it in, but you also love your family more than anything imaginable. That is a tough push-pull that never goes away, and unfortunately, it also is the basis for the larger gender bias that exists around the world. We all need to be more conscious of it. I am personally very tuned in to the challenges of balancing a family and a career, and at POPSUGAR, we have worked hard at making the transition back to work as easy as possible. In my life, and in many women’s lives, balance is important but often hard to achieve. I find it helps to be very present wherever you are at any given time.

"Being an entrepreneur is extra challenging for a woman, so it’s important to not go at it alone."

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Where do your drive and passion come from?

Our audience and fans and my family continue to drive me to keep going, whether it’s challenging us to reevaluate our content, to think differently, or to get excited about a new product or site launch. The beauty of being such a young company is our jobs have grown and changed so much over the years that every day seems like it’s a new job. I want to make sure it’s also just as much fun and fulfilling for our new hires as it is to those who have been with us for the entire 11 years.

When you run into a career obstacle, what drives you forward?

So much of the media industry involves change. I learned early on you need to keep moving forward and innovating to survive. When we started, social media wasn’t a thing and the iPhone wasn’t even invented yet. Now, new platforms and mobile are an extremely important outlet for us. We can reach millions of more people thanks to them. It also means we have to think about how to budget more efficiently or adapt content for various audiences. As much as we’ve grown and changed, one thing I draw the line at is our voice and tone. I protect our supportive and kind POV. That's built into POPSUGAR’s DNA and it’s here to stay.

What is your biggest pet peeve?

I am the person who would give you a look of death if you were tapping your pen in class. I can’t stand annoying small noises when I am trying hard to concentrate.

What are your biggest fears about running a business?

Maintaining our success, of course, is always on my mind. Brian and I have so many people and their families depending on our continued growth. From there, fostering an atmosphere where people can thrive and are really be happy is a perpetual thought. I want to make sure kindness is part of everyone’s experience at POPSUGAR and I’m vigilant about banishing any whiff of a Mean Girls culture from taking hold. :)

What's something you'd like people to know about your job that they probably don’t?

What people don’t know is that I am a total beauty junkie! I love beauty products and have to test items for our Must Have subscription box and also for our upcoming beauty line, Beauty by POPSUGAR. It’s one of my favorite “work” demands :)

Every day there is someone in your shadow. How can we stay original when we are so saturated with other people's work?

We see ourselves as a family and I do my best to be really supportive of all of our entire staff. We’re successful because we let our great staff shine and find their unique voices. Every writer is original, and that’s why people keep coming back to us. If our competitors are imitating us, it’s a compliment, but we will continue to be first, purposeful and feel-good as always. Also, it’s extremely important to take the extra time to figure out the unique angle — what is the POPSUGAR POV for each story? We make sure our team works smarter to avoid going down the most obvious route.

What about your career makes you feel the most complete?

Our team! I love growing up with them. We started this company when I was 29. It’s been such a wild ride. It’s been so fulfilling to watch so many of our early staff members grow into tremendous, confident leaders. I love that. It makes me feel great. Our company mantra is “work hard, play nice,” and seeing that infuse every aspect of POPSUGAR makes me go to sleep with a smile on my face.

If you had to trade jobs with anyone else in the world, who would it be and why?

Oh, this is a fun but tough question. I love the idea of a day in the life of Victoria Beckham. To be able to design clothes, create a beauty line, be a mom to 4 adorable kids and a wife to David Beckham seems like a dream job ;) I’d say the same of Drew Barrymore too — wine, beauty line, clothing line, plus entertainment — seems like the best variety of ways to be creative. These women have worked hard and created their own paths in life to success. They continue to be creative in new ways and juggle new challenges each year.

You've said that one of the reasons you saw success was because you learned to speak up. At what point in your career did you find the confidence to really take charge and become the woman you are today?

I spent the early years of my career in advertising and it didn’t exactly foster a speak-up environment. I knew it wasn’t for me. Managing multimillion-dollar budgets in various Excel charts was not my calling. In my spare time, I was writing reviews, testing beauty products and taking any work breaks to search online and go down rabbit holes to be the first to know something new. Ultimately, it led me to speak up in a totally new way — through my writing by starting POPSUGAR. I took a risk and started something completely different on my own, and that was the first step toward truly finding my own voice. Since we started the company from scratch, I was comfortable speaking up and made sure all new employees felt the same way. It was always very collaborative. I’ve had to rend my voice as we’ve grown or my job has taken me down new roads to do more keynotes, panels, and presentations to complete strangers. This was scary at first, but I find the more I do it, the more I feel confident in who I have become today.

What's the best advice you've ever been given? Or your favorite piece of #realtalk?

The best advice I’ve ever received was from my dad when I was little: he told me to do what I love. It sounds so simple, but it’s not and sadly most of us don’t. His advice has never failed me.

What song do you sing in the shower when you’ve had a bad day?

Ha, I’m not much of a sing-in-the-shower girl, but I am happy to always blast music in my kitchen or working out. If I’m having a bad day, I’d probably throw on “Freedom!90” by George Michael, Rihanna’s “Must Be Love on the Brain” and/or “May I Have This Dance” by Francis and the Lights featuring Chance the Rapper.