Orlando juggles busy practice with children’s online success

It all started with his son Johnny Orlando’s innocent Justin Bieber cover on YouTube.

Now — millions of views later — Toronto critical injury lawyer Dale Orlando is balancing his busy law practice with the schedules of his social-media savvy son, and his other children, as they manage burgeoning entertainment careers.

“It’s been the summer of Johnny,” says Orlando, co-managing partner of McLeish Orlando LLP, who recently returned from a tour with his 13-year-old son Johnny throughout the United States.

Johnny Orlando has nearly 1.1 million YouTube subscribers and more than 1.8 million followers on Instagram. As a result of his growing online success as a social media influencer, the entire Orlando family — including the family dog, Bentley — also have massive social media followings. The online presence has led to a successful career involving non-disclosure agreements, product endorsements and paid appearances for Johnny and his siblings.

Work-life balance

For Orlando, whose law practice focuses on catastrophic personal injury claims, his children’s success has meant his own career has required a new definition of work-life balance.

He has learned to embrace his firm’s “paperless office” — working in an LA airport as productively as his colleagues in Toronto — and relying on the expertise of his excellent team of partners at McLeish Orlando.

So while Orlando aims to represent individuals and their families after a serious injury, he is also assisting his own children in the pursuit of their dreams.

“I’ve executed contracts for John and I’ve consulted with several entertainment lawyers,” he says. “I’ve always been a personal injury lawyer, so I’m slowly learning the nuances of the world of entertainment law.”

Four children

Johnny is one of Dale and Meredith Orlando’s four children. Madison, 20, is attending Western University, Darian, 18, is taking creative industries at Ryerson University, and Lauren is 11.

While Johnny and Lauren have amassed huge Instagram followings, the older children are also actively involved in their siblings’ success.

When Johnny was eight years old, Darian asked her parents if she could post a short YouTube video of her brother singing Mistletoe by Justin Bieber.

“We just thought it would be kind of cute and a way for us to email their grandparents and just say, ‘Hey, check out what the kids are up to,’” Orlando says.

They posted the video, and to the family’s surprise, it got around 2,000 views. So they followed it up with another Bieber cover of the song “Boyfriend.”

Before long, American Idol host Ryan Seacrest discovered Johnny’s song profiling it in a radio contest.

He introduced him as “a nine-year-old crooner from Toronto, Canada named Johnny Orlando,” Orlando says. “He got something like 50,000 views and Darian just kept it going. So when you look at Johnny, it’s all Darian.”

Darian helps write Johnny’s songs, manages his social media, tours with him, dresses him, acts as a vocal coach and sometimes performs with him on stage, says Orlando. Lauren sings and makes YouTube videos on her popular channel, LaurenLogs.

Boys of Summer tour

This summer, the family toured almost the entire month of July on the Boys of Summer tour. He also performed at Playlist Live with other YouTube stars in Washington, D.C.

Orlando says watching his son’s career unfold has been quite a ride. Johnny now gets recognized when he goes in public and he often must set aside extra time to pose for photos with his fans.

The goal for Darian and Johnny is to break into major pop star status, but Orlando knows it’s a tall order in a competitive landscape.

“If it doesn’t catch on, it’s still been a good learning experience for the kids,” he says. “They have certainly learned work ethic, and they have developed a confidence level, interacting with crowds and with adults.”

Every dollar earned is being saved for the children’s futures, Orlando adds.

“They’ve got the best business model in that their parents pay for all the expenses, and the kids get all the revenue,” he says with a laugh.

Managing a major law firm along with a busy family may not be easy, but Orlando has found a way to make it work as he continues to achieve success for his catastrophically injured clients — something he truly believes in.

System of teams

As McLeish Orlando has evolved, the firm has developed a system of teams, where partners work with each other on most files. Orlando works with Joseph Cescon and Salvatore Shaw.

“Whenever I open a file, I work on those files with one of my capable partners,” he says. “We have a two-partner system in my group, and a very rigid system of file development with regular file review meetings. I participate in those meetings but I’m able to step back and let the junior partners work with clerks and the rest of staff to do the development.”

Orlando attends trials, mediations and some discoveries while delegating wherever possible.

The firm focuses on catastrophic injury claims for people who have suffered injuries as a result of someone else’s negligence, whether that’s a motor vehicle crash, medical malpractice or product liability.

“I really enjoy working for people who need the benefit of the expertise that we bring,” he says. “I believe we do an exceptional job for our clients and work hard to ensure they get fair and reasonable compensation for the losses they’ve suffered.

“I like being the champion of the underdog, so to speak. Typically, we are fighting a large institutional client and I enjoy that challenge while seeing the impact that we have on our clients’ lives.”

 READ more in Precedent Magazine.