While traveling home from a family vacation, Juliette Brindak, age 10 at the time, entertained herself by drawing pictures of her 5-year-old sister Olivia and her friends, whom she referred to as “the cool girls.”

Those drawings would become the inspiration for Miss O and Friends, a website that Brindak launched in 2005, and where, today, some 1 million girls go each month to find a sense of community on its thriving message boards.

On Miss O and Friends, girls “socialize, play, create, exchange ideas and compare experiences,” through games, articles and more, says Brindak. The site also offers programs that let girls enter fashion design contests and gain internship opportunities.

“Our main goal is to provide a safe place online to empower girls, so they can realize that they aren’t alone, and that they don’t have to grow up too fast,” she says.

That formula made for a flourishing website during its first few years — until 2014 when a major site renovation brought major trouble. Amid a mismanaged transition, Miss O and Friends’ traffic plummeted from a peak of 3 million monthly visitors to one-third that number.

“It was definitely frustrating, but I was confident those views would go back up,” Brindak says.

Shooting for the Stars

Brindak, who is now 28 and a recent newlywed who has recently taken the name Juliette Brindak Blake, remembers all too well how it felt to be young and vulnerable.

A wish to assuage those feelings are at the heart of her business. Her startup story begins with those “cool girl” drawings, which her mother Hermine saved for years and then, as a surprise, blew up into life-size decorations for Olivia’s 8th birthday party. At the party, Brindak, who was 13 by that point, noticed the girls voicing quite uncool insecurities. “It was hard to see my 8-year-old sister talk about getting fat, and to see her friends worried about eating a cupcake because they didn’t want to gain weight.”

Motivated to make a change, she decided to take advantage of the then-booming popularity of the internet and launch a website for girls ages 8 to 14. Her parents became co-founders, with her mother bringing design skills, while Brindak’s father, Paul, put his business background to use, helping the company get formally established and hiring web developers for the site.

Three years of work later, the Miss O and Friends website was fully functional and ready for launch in April of 2005 — making Brindak an entrepreneur at age 16.

She grew the business, which is based in Philadelphia and makes money by showing advertisements, with help from her family. When Procter & Gamble invested in the company in 2008, it was valued at $15 million. By 2011, the site had 3 million monthly visitors and ranked as the third-largest website for young girls, according to data from Alexa.

In addition to regular visitors, Miss O and Friends now has 800,000 subscribers, all of whom are able to interact on its Girl2Girl wall, a forum where girls can ask each other questions and share advice, and access other content to help them grapple with the struggles of growing up.

To ensure a safe experience for its entire audience, the website adheres to rules set out in the Children’s Online Privacy Protection Act (COPPA), which protects the privacy of children under 13. As a result, the company does not use social media platforms that don’t use age verification, which means it is not on Twitter and a number of other larger social sites.

Miss O and Friends’ dedication to protecting its users has resonated particularly with the mothers of its target audience — so much so that Brindak launched Moms with Girls  in 2012. It’s a sister mommy blog that features articles on parenting, food, health and fashion for mothers of young girls.

“The responses from both moms and girls make me feel like I’m changing lives, and that’s all I want to do,” she says.

Growing Pains

But just as Brindak’s business hit its peak — and as she was graduating from Washington University — a big change threatened to undo her hard work.

In 2013, she decided to upgrade Miss O and Friends’ underlying web software, known as a content management system. Maintaining the original website was a “pain,” she says, because it required regular software updates. So she decided to switch to WordPress.

But the upgrade didn’t go well, to put it mildly, and the site shed  visitors. “We wanted to update our site to make it better, but I think we were making too many changes at once for our users,” she says. “We knew it was going to take a lot of time and money to do it, and that deadlines would be pushed, but we didn’t realize how much longer it would actually take.”

The renovations took almost 2 years to complete. It was a painful lesson for Brindak, who says she learned the importance of measuring “time” in all her decisions. She also learned that while bringing in new ideas a business can lose track of its clientele.

On set of “Hyperlinked,” a new offering from Miss O and Friends, with Tati McQuay, Jenna Simmons, Mckenzie Mack, Mariangeli Collado and Lexi Drew, members of girl band L2M.

Despite the setback, she’s proud of her bold choice, believing it made for a better product in the long run. “Every business and website can always be better, and our goal is to continue to have the Miss O site to evolve to have the best and most relevant user experience.”

Introducing New Ideas

Indeed, Brindak continues to pursue new ideas for Miss O and Friends. Her latest project is a video series called “Hyperlinked,” which will air on YouTube Red and the YouTube Kids app this spring. The show will bring to life the story of how Miss O and Friends was created with some help from the girls of L2M, a “tween” singing group. The first episode will be available for free, but to watch the remaining nine episodes, viewers will have to subscribe to the Miss O channel.

Brindak has hit her stride with the venture, she says, and is now enjoying the entrepreneurial life with her partner and beloved Beagle, Louis. Despite the ups and downs, she remains dedicated to her mission: helping girls through a difficult and formative time in their lives.

She says the web video series will be a good step in the right direction, providing something her audience has been requesting for years. “I try to listen and stay up-to-date with what girls want, since I’m no longer a tween,” she says. “It’s important for me to understand their needs.” She also hopes the show will be a hit that wins back more of her fans.