The Boss: Jill Smokler Turned Her Parenting Struggles Into a Successful Media Company

In The Boss, successful women share how they reached the top and the lessons they learned along the way.

In early 2008, I found myself in an unfamiliar town with three kids under four, a 100 pound dog and a husband who traveled three days a week for work. Needless to say, my house was Crazytown. It was loud, chaotic, messy and nothing like the magazine pictures I stared at or the families I saw on TV. I was drowning, while all the other moms I interacted with seemed to be blissfully skipping through motherhood. It must be me, I thought — I’m just not a natural mother.

Turns out, I was. And I am. But I never would have known that without Scary Mommy.

I started the blog on a whim one afternoon while the kids napped. I liked the idea of having a project of my own and I figured it would be a good way to document our days at home. It was free, easy and harmless. But then something happened that changed everything – I got my first random comment. Up until that point, I thought a blog was simply meant to house stories for friends and family, not for interacting with strangers on the world wide web. Why on earth would anyone want that?! But that comment led me to that reader’s blog, and from there I discovered a whole world of moms. And these moms, unlike any I’d met before, actually understood me! They struggled and shared the same frustrations. They yelled at their kids, burned dinner and sometimes daydreamed about running away to some fancy hotel for a few hours of peace and quiet. I wasn’t the only one — and the epiphany was life changing.

From that day on, I was addicted. I spent hours scouring the web to find new blogs to read. I posted something every day, even if it was just a short apology post for not writing more. I created a logo, bought the dotcom rights and attended every conference I could to learn more about starting a business. Slowly but surely, I built up the Scary Mommy community — a virtual village.

As the website grew, I added features to allow my readers to submit their own content, transforming the site from my personal journal into a community of imperfect parents. But it was definitely challenging. I was probably sleeping an hour or two a night. I was taking conference calls in the car while I was driving my kids to school. I eventually became so burnt out that I knew I needed to either sell the company or try to bring investors on, which is a daunting prospect.

In 2015, just seven years after starting the company, I sold Scary Mommy to Some Spider Studios, a media company headquartered in New York. These days, as editor-in-chief, I oversee the heart of the company – the content — while a staff of over 100 people do the rest of the work. It’s not easy leaving your baby in new hands, and I’ll admit the transition difficult at times. However, the tradeoff has been worth it – I’m no longer glued to my computer 24/7 and I’m a bit closer to finding that ever-elusive balance.

Scary Mommy has gone from publishing just a handful of pieces a week to 20 a day – a number I never could have conceived of a few years ago. We now have almost 6 million fans and followers across our social platforms. We have a booming branded team, video team and sales team. But I’m most proud of the fact that my very first employees all still work on the website.

I believe that the success of Scary Mommy is rooted in its authenticity. Had I set out to create a parenting business, it likely wouldn’t have focused on my shortcomings and failures – the very things that set Scary Mommy apart from every other site. Because it began with my personal stories, the tone of the site was very focused and defined. In a word, it was me. That’s probably the reason I’m never tired of all things Scary Mommy, even as we approach our 10-year anniversary.

That’s a good lesson to fellow entrepreneurs: Make sure you are passionate about whatever it is you’re doing. Otherwise, what’s the point? If you bring passion, honesty and authenticity to your budding business, people will respond. It’s really a magical combination.

Jill Smokler is a New York Times bestselling author and the founder of Scary Mommy.