EP349 From $300 to a Multi-Million Dollar Exit

Bobbie Racette started with $300 at her kitchen table. Nine years later, she became the first Indigenous woman in Canada to build, scale, and sell a tech startup. In this episode - the first time Bobbie has dug into the details of the sale on a podcast - host Colleen O'Connell-Campbell sits down with the founder of Virtual Gurus, an AI-powered inclusive talent marketplace that matched underrepresented talent with businesses including Mastercard, Telus, and BMO. Bobbie shares the full arc: bootstrapping to $1.8 million in revenue before raising a cent, hearing 170 no's before closing a seed round, scaling through three funding rounds during COVID, becoming the first Indigenous woman in Canada to close a Series A, navigating founder fatigue, stepping down as CEO before the exit, and ultimately selling to a U.S. private equity firm that rolled Virtual Gurus into North America's largest virtual assistant platform - with the AI sold separately to a Calgary company. This is a conversation about what it takes to build something from nothing, what it costs personally, and what comes next when the mission is bigger than the transaction.

Key Takeaways:

Bobbie created Virtual Gurus in 2016 after being laid off in oil and gas and unable to find a job. She is Cree Métis, queer, and covered in tattoos - and nobody would hire her. The business started as a way to create a job for herself and evolved into a platform providing remote work to marginalized talent across Canada and the U.S.

She bootstrapped to approximately $1.8 million in annual revenue before seeking external funding. The seed round took over two years and 170 investor rejections before closing at $1.25 million. The Series A, two years later, was significantly easier.

Virtual Gurus scaled past $40 million in revenue and closed three funding rounds during COVID. Total capital raised was $14-20 million.

The exit was not originally planned. For the first four years, Bobbie intended to keep the company as a legacy business. The shift came around 2022 when the scale of the operation began to outpace the original mission. The board recognized that an acquisition was likely the best path forward.

The company was simultaneously pursuing a Series B and fielding acquisition offers - a dual-track process. The data room was already built for the fundraise, which accelerated due diligence to approximately five months. The acquisition by a U.S. private equity firm closed in November 2025.

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