In this episode of The Moment, Bobbie Racette, founder and CEO of Virtual Gurus, shared her journey from an unexpected layoff to building a company that’s changing the way businesses hire remote talent.

She sat down with our co-hosts Fatima Zaidi and Jason Maghanoy to discuss the candid moments behind her company. From 170 investor rejections to overcoming self-doubt, Bobbie’s story is a testament to resilience and the power of creating your own opportunities.

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Introducing Bobbie Racette and Virtual Gurus 

Bobbie started her career in oil and gas, but after being laid off in 2016, she found herself working at a coffee shop, unsure of what was next. 

It was there that she saw a gap in the market: businesses needed reliable virtual assistants, and there were plenty of skilled workers struggling to find flexible jobs. That idea became Virtual Gurus, a platform that connects businesses with remote talent from underrepresented communities.

As an Indigenous Métis Cree entrepreneur, Bobbie built Virtual Gurus with a focus on diversity and inclusion, ensuring that marginalized workers — particularly Indigenous, Black, and LGBTQ+ professionals — have access to meaningful work. Today, she’s not only leading a growing company but also serving on the boards of the Indigenous Prosperity Fund and the TELUS Friendly Future Foundation.

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Key takeaways from our conversation

Allowing rejection to fuel determination 

When Bobbie started pitching Virtual Gurus to investors, she was met with rejection — again and again. “The first 10, 20, 30 no’s… it hurt a lot,” she admitted. The repeated rejection made her question whether she could actually build the company she envisioned. But a conversation with her mother shifted her perspective. “She sat me down and said, ‘You can do anything you put your mind to. Don’t let them tell you no — let their no’s fuel your fire.’”

That fire turned frustration into determination. “At first, I felt defeated, but then it became a vengeance. I told myself, ‘I got this, and you can’t tell me no.’” All she needed was one yes. That yes finally came, and it changed everything. “Looking back, that phase was medicine for me. It made me a different person — stronger, more resilient.”

Bobbie also had to rethink her approach to investors. Initially, she was targeting traditional venture capitalists, but many didn’t align with her vision. “What I really needed were impact investors — people who understood that Virtual Gurus was about more than profit. It was about creating opportunities for underrepresented talent.” 

That realization led her to Raven Indigenous Capital, which became her lead investor. “I saw a Globe and Mail article about them investing in an Indigenous tech platform. I cold-emailed them immediately, and within five minutes, they were on the phone with me.”

For Bobbie, fundraising wasn’t just about securing capital — it was about finding investors who believed in her mission. Now, she’s using that experience to prove that diverse founders can build successful, high-growth companies — on their own terms.

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Don’t let fear hold you back

Fear and discomfort are often signals for growth — something Bobbie Racette learned firsthand. 

During a high-stakes accelerator demo day hosted by Arlene Dickinson, she was moments away from pitching to a room full of investors. But something didn’t feel right. “I just couldn’t do it,” she admitted. “The idea of standing up there, pouring my heart out, and asking for money — it just didn’t sit well with me.” Instead of pushing through, she made a split-second decision to leave.

While walking away could have been seen as a setback, Bobbie saw it as a turning point. “I knew I had to get over that fear,” she said. Determined, she entered a global startup competition in San Francisco, pitched in front of 8,000 people, and won. A week later, she competed at Startup Fest in Montreal and placed as a runner-up.

The experience taught her that fear isn’t a sign to stop — it’s a signal to adapt and re-strategize. 

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Facing imposter syndrome head on

In the early days of Virtual Gurus, Bobby struggled with imposter syndrome. Despite having built something promising, she didn’t believe she had the experience to lead it. Instead of stepping into the CEO role herself, she made an unconventional decision — she put out an ad on Kijiji looking for someone else to take the job.

She hired someone to lead the company, it became clear within six months that he wasn’t the right fit for the business. “At one point, he was talking about putting virtual assistants on drones,” she recalled. “And I was like, what? How does that work? That was the moment I realized this just wasn’t going to work.”

That realization forced Bobby to confront something bigger than just a misaligned hire. She had been looking for someone else to lead because she didn’t believe she could do it herself. But after seeing the wrong person in the role, she finally recognized the truth: “There was nobody better to do this than me. I needed to pull up my big girl pants and learn to do it.”

Determined to close the gap between where she was and where she needed to be, Bobby stepped back into the CEO role, enrolled at Harvard to develop her leadership skills, and led the company through a period of rapid growth. “During the pandemic, virtual groups experienced 600% year-over-year growth,” she explained. “And we just kept going and going.”

Looking back, Bobby doesn’t regret hiring someone else — she regrets doubting herself when she should have believed in her own abilities. But in many ways, that experience was necessary. It forced her to step into her role with confidence, and it solidified the lesson that sometimes, the only way to overcome imposter syndrome is to face it head-on.

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Listen to “How Virtual Gurus’ Bobbie Racette Handled 170 Rejections Before Securing an Investor”

To learn more about Bobbie and the candid moments behind Virtual Gurus, tune into the full episode wherever you get your podcasts.

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