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. The AI platform was sold separately to a Calgary-based company - effectively a double sale. The core business was rolled into the acquirer's larger virtual assistant platform. Bobbie had stepped down from CEO to president in May 2025, with her COO becoming successor CEO. The successor stayed with the company through and after the acquisition. Bobbie's role during due diligence was primarily support - being available for the team mentally, emotionally, and strategically, while the finance team and executive team drove the process. Founder fatigue and decision fatigue were real and significant. Bobbie emphasizes that founders need to talk about this more openly, and that boards and investors need to be supportive during those low periods rather than adding pressure. Retention of employees during due diligence was one of the hardest parts. Bobbie's culture at Virtual Gurus was built on honesty and transparency, and not being able to tell her leadership team about the acquisition felt deeply uncomfortable. Post-exit, Bobbie has retired her parents (her mother was her first angel investor, contributing her last $20,000), bought a new home, and is investing time and capital into the next generation. She is now an angel investor in five businesses - all founded by people from underserved communities, including Indigenous and LGBTQ+ entrepreneurs. She has launched Tapwe (Cree for "truth"), a platform to support underserved founders with financial literacy, mentorship, AI-powered matching, and startup scaling resources. A documentary is in production. Her newsletter, The Fire Report, scaled to 4,000 subscribers almost immediately. She is also doing regular paid advisory sessions each week through her website. Bobbie's story is a reminder that a cash-rich exit can be deeply values-driven, inclusive, and barrier-breaking - and still set you up for whatever comes next. If today's episode has you thinking about your own journey, whether you are at the kitchen table, scaling fast, or quietly eyeing your exit, book a one-on-one Wealth Gap Analysis with Colleen O'Connell-Campbell via LinkedIn or email Please leave a five-star rating and review to help more founders find this show. *** The Cash Rich Exit Podcast is brought to you by O'Connell-Campbell Wealth Management at RBC Dominion Securities. All opinions expressed by the host, Colleen O'Connell-Campbell, and podcast guests are solely their own opinions and do not reflect the opinion of RBC Dominion Securities. This podcast is for informational purposes only before taking any action based on information in this podcast you should consult with a qualified professional. Colleen O'Connell-Campbell is a Wealth Advisor at RBC Dominion Securities, a member of the Canadian Investor Protection Fund.




