When Oorbee Roy picked up a skateboard at 43, she had no idea it would change her life. What started as a fun way to spend more time with her kids quickly turned into something bigger. She began sharing her journey on TikTok during the pandemic, hoping to spread some joy during a difficult time. “Everyone was depressed, and I just wanted to make people smile,” she says.
Also known as “Aunty Skates” on social media — Oorbee’s videos went viral, amassing over 100,000 followers in just four months. “I wasn’t working at the time, so I just kept going,” she says. But behind the viral success, Oorbee’s financial journey has been shaped by her upbringing, her family, and a series of hard-earned lessons about money and investing.
Balancing Family, Finances, and Investing
As a mother, Oorbee is focused on making sure her kids have a strong financial future. “Kids are king,” she says. “We have to invest for their future and make sure they have money for their education.” She learned the importance of long-term investing early on, thanks to a lesson from her parents that stuck with her for life.
“When I graduated from university and was still living at home, my parents started charging me rent,” she recalls. “But what I didn’t know was that they were actually investing that money for me. Later, they gave it back to me for a down payment on a house.” At the time, she admits she would have spent that money frivolously had they not saved it for her. “It was one of the best financial lessons they could have given me.”
Now, she’s passing down financial lessons to her own children. Her kids have Mydoh cards, a financial tool that allows them to manage their own allowance and learn about budgeting early on. She also makes it a point to have open conversations about money at home, something she believes many parents struggle with. “Most parents want to teach financial literacy, but we don’t always know how. We end up learning it ourselves in our thirties after messing up a few times.”
Finding the Right Financial Support
Despite those early lessons, Oorbee didn’t always feel confident about investing. She worked on Wall Street in her early career and was eager to take risks—until a financial advisor shut her down. “I once had an advisor tell me, ‘You don’t make enough money to take risks,’ and that completely turned me off from investing,” she says.
For years, she avoided the market, feeling like investing wasn’t for her. It wasn’t until she got married that she revisited the idea, but even then, she struggled to find an advisor she trusted. “The first advisor we met made us feel stupid, and I was turned off again,” she admits. “If you don’t vibe well with your advisor, it can really throw you off.”
Eventually, she and her husband found an RBC advisor who understood their goals and made them feel comfortable. “Now, our advisor is great—he never talks down to us, and he was actually the first person to jump at the idea of turning my TikTok skateboarding account into a business.”
For Oorbee, the key to a good advisor is trust, transparency, and a willingness to listen. She also reminds people that it’s okay to change advisors if the relationship isn’t working. “You don’t have to give them all your money right away. If something doesn’t feel right, you can always switch.”
Entrepreneurship and Financial Freedom
Becoming a full-time content creator brought a new level of financial uncertainty. “It’s a hustle to be an influencer,” Oorbee says. Unlike a traditional job, her income fluctuates, with most brand deals coming in the summer when skateboarding is in season. “There are months where I know I have to be lean. I have to tell my kids, ‘No, you’re not getting an expensive jacket and boots this year.’”
That unpredictability has forced her to be strategic with her money. She prioritizes investing in her RRSPand TFSA, knowing that they can offer tax benefits while helping her plan for the future.
But her financial goals go beyond just saving. “This year, my goal is to build more passive, regular income so I don’t have to rely so much on brand deals. That way, it’s more consistent and less stressful,” she says.
Lessons from an Immigrant Upbringing
Growing up in an immigrant household, Oorbee saw her parents struggle, and it shaped her mindset about money. “Our understanding of a dollar is so different from our kids’ experience today,” she says. That’s why she makes a point to include her children in financial conversations.
“I celebrated with my daughter how much I made last year,” she says. “I want them to see the hustle, to understand that making money takes effort.”
Despite her success, she still believes in living below her means. “I’m 50, and I’ve been driving the same Subaru for 12 years,” she says. “You don’t need to spend more just because you earn more.”
Looking Back: What She’d Tell Her Younger Self
If she could go back in time, Oorbee’s advice to her younger self would be simple: “It’s never too late to start investing.” She knows that her ability to take risks today—whether in business or in life—comes from having a financial cushion.
“You don’t have to be perfect. Just start, take small steps, and keep going,” she says.
It’s the same advice she gives to those learning to skateboard—and to anyone looking to build a more secure financial future.
