When Robert Ostfield took over music and pop culture portal andPOP.com, it was a tiny operation run by a couple of ambitious university students. In fact, Ostfield himself had just graduated from Ryerson University’s Ted Rogers School of Management when he became CEO of the company.

Today, andPOP is one of Canada’s leading entertainment portals for teens and young adults. The site books exclusive interviews with some of the hottest names in the music industry – we’re talking Lady Gaga, Justin Bieber, Selena Gomez, Jason Derulo and Ellie Goulding, among many others. What’s even more impressive: the brand’s videos have scored more than 21 million views on YouTube alone.

Ostfield, who now oversees multiple websites as managing director for Channel Zero Digital, whose parent company has owned andPOP since 2012, says his success couldn’t have happened without two key ingredients: hustle and help.

“I think I’ve always been a little bit of a hustler and just a natural sales guy,” he told The CJN. “And I’ve always admired sales people. You read profiles of successful entrepreneurs and get inspired, and of course you want to imitate that kind of success.”

During his university years, Ostfield was a member of Jewish fraternity AEPi. That’s how he met andPOP founder Michael Levine, who introduced him to the website and co-founder Adam Gonshor. Ostfield quickly became involved with the business side of the site, eventually taking it over once he graduated. The young entrepreneur made one very important change by adding more video content.

“I saw how I was consuming media and how at the time, going back 10 years ago, the world wasn’t set up to address that need,” he said. “So I just genuinely saw an opportunity and thought I could develop the expertise and the know-how in order to exploit that opportunity.”

At that point, he was already getting access to celebrities. He thought: why not create video content instead of just written profiles? “There’s value in the access, but if you can really produce everything into compelling video content, there’s double the value or triple the value,” he said.

The emphasis on videos made andPOP stand out at the time. “That’s how we became an official YouTube partner very early on. It’s that we had high-quality video content with celebrities.”

The editorial approach also made the brand stick out from some of its larger competitors.

“Because we were online and because we were a small operation, we could do whatever we wanted,” Ostfield said. “So we could ask a boy band about picking up girls and doing drugs and getting drunk. The MuchMusics, the Kiss 92.5s won’t and can’t talk about that. But we’re online. We can do whatever we want.”

The site continued to build its credibility by sealing partnerships that made the brand more valuable. Over the years, some of those partners have included AOL Canada, XM Radio, Yahoo Canada and even Esso.

“Really that made the record industry look at us as a major, legitimate player,” Ostfield said. “So when they’re creating their press schedule for Lady Gaga they say, ‘Yeah we gotta do MuchMusic, we gotta do Kiss 92.5, but andPOP really gives us a wide distribution – we gotta be on there, too.’”

He said andPOP’s easy-to-work-with team has made the site popular with publicists and music execs. He also attributes a good part of andPOP’s success to the great mentors he’s counted on, including Jordan Banks, managing director of Facebook Canada.

“The best thing he taught me was, ‘Be nice to people on your way up because you’ll meet them on your way down.’”

Banks, who’s also Facebook’s global head of vertical strategy, joined andPOP as an investor and board member in 2010. Later, Canadian Music Industry Hall of Fame member Gary Slaight also invested in the company. Ostfield singles out two other individuals as close advisers and friends: Google’s Neil Shankman and entrepreneur Jamie Grossman. “If I’ve had success, a lot of that has to do with the fact that I’ve had a lot of help,” he said.

The site expanded in 2011 by raising some money and acquiring ChartAttack.com. “The old Chart Attack would talk about Billy Talent and Nickelback,” Ostfield said. “Our Chart Attack talks about Arcade Fire and Broken Social Scene – it’s kind of that Queen Street West indie alternative crowd.”  

Just like with andPOP, Ostfield started putting an emphasis on video content with Chart Attack, and the site’s popularity has since grown significantly. He also makes sure his staff, interns and contributors are all in the same age group as his audience (i.e., teens and 20-somethings).

“We think it’s a mutually beneficial opportunity, because for one, they allow us to really be authentic and talk about the right things that our audience cares about,” he said. “And at the same time, they’re getting amazing opportunities running this brand… So we think it’s a win-win.”

In 2012, Channel Zero – the largest independent broadcaster in Canada – acquired a controlling interest in andPOP Inc. “Both parties recognized that there was an interesting marriage that could happen here and Channel Zero Digital was formed,” Ostfield explained.

In his new role as managing director, Ostfield oversees all of Channel Zero’s main digital properties, including CHCH.com. He continues to manage andPOP and Chart Attack, and he also represents Sony’s Crackle.com brand in Canada.

Needless to say Ostfield’s a busy guy, but he always makes time to help others.

“You get what you give and I’d like to try to help the next generation of entrepreneurs by giving them the same kind of support that I have received,” he said.

After more than 10 years in the business, the entrepreneur is still living by his motto: hustle and help.