The Cash Rich Exit Podcast

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.

What happens when four moms start making labels in a Hamilton basement and, 14 years later, get a call from a global industry giant? In this episode, host Colleen O'Connell-Campbell sits down with Julie Cole, one of the four co-founders of Mabel's Labels, to trace the full arc: from masking tape and permanent marker frustrations in the early 2000s, to building a fiercely loved e-commerce brand, to a reported $12 million acquisition by Avery Labels that closed in under six months. What makes Julie's story unique is the fact that she is still at Mabel's Labels a decade later, now as Senior Director of Public Relations, championing the brand she helped build. The conversation covers what buyers actually look for, why keeping your house in order is non-negotiable, how four co-founders (who were also family) navigated decisions without destroying relationships, and why selling your business does not have to mean falling out of love with it. Key Takeaways: Mabel's Labels was founded approximately 23 years ago by Julie Cole, her sister, and two university friends who married into the family. It started in a Hamilton basement solving a simple problem - kids were losing their gear, and there was no good labelling solution beyond masking tape and marker. The four co-founders divided responsibilities by department (production, IT and finance, marketing, PR), which worked well early on but eventually created silos. Each founder became protective of their team's priorities, and the business reached a point where it needed one person overseeing the whole operation rather than four co-CEOs pulling in different directions. Managing a co-founding team that is also family requires deliberate effort. The founders brought in a coach to navigate difficult growth decisions and to separate business disagreements from personal relationships - a practice Julie compares to Midday Squares' weekly "family therapy" sessions. The acquisition by Avery Labels (a publicly traded company) happened fast - the initial call came in July, and the deal closed on New Year's Eve of the same year. Julie emphasizes this timeline is not normal and should not be expected. Due diligence is where you can lose money. A letter of intent might come in at one number, but if the buyer finds problems, the offer shrinks. Julie's advice: keep your housekeeping in order from the start, not just when a deal appears. The exit process is a full-time job. Having four co-founders meant one could focus on the transaction while the others kept the business running - a luxury solo founders do not have. Julie has seen entrepreneurs take their eye off operations during a sale, get left at the altar, and end up with a year of lost sales and deal fatigue. Because Avery is publicly traded, the founders could not tell their staff about the potential acquisition. They told the team it was a tax audit - which felt terrible given their culture of transparency - but was necessary for regulatory compliance. Once the deal was announced, the founders led with reassurance: no one was losing their job, the brand was staying, and the team would be supported through the transition. Two co-founders left immediately after the sale, one stayed as general manager for a couple of years, and Julie has remained for 10 years. She now reports to a former direct report who became GM - and is fully at peace with that dynamic. Her role is to be the brand's voice, its public face, and its connection to the community. The brand's longevity is built on community. Julie was one of the original "mom bloggers", has attended Mom 2.0 conferences for 18 years, and has continuously followed her audience from blogs to Facebook to Instagram to Reddit. Mabel's Labels looks like a low-tech product but is a high-tech, e-commerce-driven business that has adapted to every platform shift for over two decades. Julie is also the author of 'Like a Mother: Birthing Businesses, Babies, and a Life Beyond Labels', a bestseller covering her parenting and entrepreneurial journey. Julie Cole's story is a reminder that a cash-rich exit does not have to be the end - sometimes it is the start of the next chapter in the same business. If her story has you thinking about your own entrepreneurial journey, book a one-on-one Wealth Gap Analysis with Colleen O'Connell-Campbell. Reach out on LinkedIn or email Could you leave a five-star rating and review please? It helps more founders find the 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.

In this episode of 'The Cash-Rich Exit Podcast', host Colleen O'Connell-Campbell welcomes back serial entrepreneur and M&A advisor Scott Duke, founder of Business Succession Group. Scott talks about his latest innovation - The Value Acceleration Calculator (VAC) - a practical, data-informed tool to assess sellability, estimate value, and identify key levers to increase enterprise value over time. This conversation covers: Why 80% of businesses never sell, and why most founders never realize the enterprise value they hoped for. How the VAC can score your business' sellability and identify where risk lives inside your operations. The three levers every founder must understand: revenue, profit efficiency, and multiples - and how each affects your future exit. Key Highlights Most businesses aren't sellable in their current state. Scott explains that many founders assume every business can be sold at some price - when in fact, buyers will simply walk away if the future cash flow risk is too high. Sellability comes down to risk reduction. The most critical factor? Dependence on the owner. If a founder is the primary relationship-holder, salesperson, or decision bottleneck - buyers see future cash flow uncertainty. Future cash flow is everything. Buyers don't buy past success - they buy the probability of future earnings repeating. Historical financials are just the rearview mirror. Three levers drive valuation: Revenue EBITDA efficiency ("how many pennies you keep per dollar") Multiple Scott emphasizes that many owners obsess over revenue (the "vanity number") rather than profitability and valuation mechanics. Energy matters. A founder's personal capacity to implement change can determine whether the strategy should be: a buildup to sale, or a multi-year harvest of cash flow instead. You can request the Value Acceleration Calculator by contacting Colleen O'Connell-Campbell directly via Linkedin If this episode sparked your curiosity about: increasing enterprise value reducing exit risk preparing for a sale in 3-10 years or planning a personal Cash-Rich Exit Reach out to Colleen O'Connell-Campbell for a 1:1 Wealth Gap Analysis. And don't forget to follow and rate the podcast - five stars appreciated! *** 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.

In this episode, Colleen O'Connell-Campbell sits down with Elizabeth Kilvert, the founder and owner of The Unrefined Olive, an award-winning olive-oil and balsamic tasting bar in Ottawa. Elizabeth shares how she transitioned from a career in environmental policy to running a thriving retail business rooted in quality, sustainability, and community connection. She and Colleen unpack the realities of small-business ownership - from managing risk and growth to understanding what a "cash-rich" exit looks like when your brand is deeply personal. Key Highlights From public service to entrepreneurship: How Elizabeth took a leap from government to business ownership and built a loyal following from scratch. Lessons in resilience: The role of adaptability and creativity when facing economic changes, global supply-chain shifts, and market pressures. Community over competition: Why Elizabeth believes relationships - not just revenue - define a business's long-term success. Defining legacy as a founder: What it means to build something that reflects your values, supports local economies, and still allows you to plan for the next chapter. Preparing for transition: Elizabeth's reflections on creating optionality - how to design a business that can run, evolve, or sell on your own terms. 🎧 Tune In To Learn How to apply a mission-driven lens to small-business ownership Why emotional connection can still align with financial value What founders can do early to create transferable, resilient businesses If you're an entrepreneur who wants to grow your company with both heart and value, this episode is for you. 💬 Connect with Colleen If you're a Canadian business owner planning your own cash rich exit, it's never too early to start. Connect with host Colleen O'Connell-Campbell on LinkedIn Request a complimentary Wealth Gap Analysis to see where you stand on your exit timeline 🎧 Subscribe and Share If you enjoy this conversation, please: ⭐ Leave a 5-star review 🔁 Share the episode with a business owner who needs to hear it 🎙 Follow The Cash Rich Exit Podcast for more insights from founders, investors, and exit experts

In this episode of the Cash Rich Exit Podcast, Colleen O'Connell-Campbell welcomes Joanna Track, serial entrepreneur, strategist, and founder of Good Eggs & Co. Joanna has launched and exited multiple businesses - including Sweet Spot, eLuxe, and The Bullet - and now leads Good Eggs & Co., a consultancy focused on content and context marketing. Known for her candid, no-nonsense approach, Joanna shares what she's learned about building brands with staying power, navigating exits, and avoiding common pitfalls that entrepreneurs face. Key Highlights: Redefining success in an exit: why an exit doesn't always equal success, and how legacy plays a role. From Sweet Spot to The Bullet: Joanna's journey of launching and scaling digital-first businesses in Canada, often ahead of the curve. The capital gap for women entrepreneurs: reflections on raising millions in funding and the systemic challenges women still face. Don't build on rented land: Joanna's hard-won philosophy on creating assets you own (like email lists and websites) versus relying on platforms you don't control. Content with context: why brands need to serve before they sell, focus on the long game, and create authentic, relatable voices. Personal brand vs. business brand: why people buy from people, and how leaders can use thought leadership to strengthen both. Growth mindset: why Joanna shifted from saying she wanted to keep Good Eggs small, to embracing its rapid growth trajectory. Fun, frank advice: be yourself, be authentic, and test - because the biggest risk is never putting your ideas into the world. Whether you're scaling, selling, or starting fresh, Joanna's story offers lessons in resilience, ownership, and building a brand that thrives beyond you. If Joanna's insights sparked ideas for your own business or exit strategy, connect with host Colleen O'Connell-Campbell on LinkedIn or to schedule your complimentary Wealth Gap Analysis. *** 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.

In this episode of The Cash Rich Exit Podcast, host Colleen O'Connell-Campbell sits down with Ashley Hopkins, President & CEO of Paradigm Commercial Group, and Sarah Vandenbelt, Broker of Record & Founder of Paradigm Commercial Real Estate. Together, they share how their unexpected journeys into real estate led to a powerful partnership under the Paradigm brand. We discuss: The winding career paths that brought them into real estate. Why building strategic partnerships and strong networks is critical in a male-dominated industry. How property management is more than collecting rent - it's finance, legal, emergency planning, and community-building rolled into one. The importance of due diligence and long-term planning in both investing and property ownership. Practical insights for business owners who want to use real estate strategically - whether as an operating base or an investment vehicle. How adaptability, collaboration, and leveraging trusted relationships drive success in real estate. Their stories highlight what's possible when business owners align passion with purpose, and when professionals join forces to provide full-service real estate solutions tailored to client needs. Fun Frank Advice: Ashley: "Don't take no for an answer. An obstacle is just an opportunity in disguise. Keep pushing, keep looking for resources, and surround yourself with the right people." Sarah: "Don't wait until you feel ready. Bet on yourself, take the leap, and trust that you'll figure it out." Connect with Ashley & Sarah 🌐 paradigmcommercial.ca **** 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.

With over $2 trillion in business assets at stake and 91% of Canadian business owners without a succession plan, we're facing a real crisis. In this episode, host Colleen O'Connell-Campbell chats with Charlie Iscoe, whose venture - CommonShares - is flipping the script on business exits. Charlie brings Wall Street investment experience and a mission to keep Canadian businesses local by transitioning ownership to employees. He explains how their model allows retiring owners to receive fair market value while protecting their teams and communities. If you're a founder who says, "I'll deal with it eventually" - this episode is your wake-up call. 🔑 Key Highlights The succession gap in Canada: 91% of business owners have no plan in place. The CommonShares model: Founders get paid a fair price, and ownership transitions gradually to employees. Why it matters: Preserves legacy, protects jobs, and keeps Canadian companies Canadian. Types of businesses they acquire: Light manufacturing, professional services (architecture, engineering, accounting), property services, etc. The people factor: How a bench of 100+ operators helps ensure continuity post-exit. What founders can do now: Start documenting what matters - financial goals, legacy values, level of future involvement. 💬 Fun, Frank Advice from Charlie "If you're listening to this, it's probably because you've built something remarkable. So don't let your exit be an afterthought. Take time. Get it right. This isn't just a transaction - it's your legacy." Want to explore your own succession plan? Colleen offers a complimentary 1:1 Wealth Gap Analysis - to bridge the gap between your business success and personal financial freedom. 👉 Connect on LinkedIn - Colleen O'Connell-Campbell - or email to book your session. 📝 Enjoying the podcast? Help us grow! Leave a 5-star rating and a short review. Every review helps more entrepreneurs find us. *** 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.

In this episode, host Colleen O'Connell-Campbell chats with Peter Deitz, social entrepreneur and founder of Canada's first-ever employee ownership trust (EOT) transition at Grantbook. Peter shares how his scenic, eight-year exit journey created space for new ventures, empowered employees, and protected the company's B Corp values. The episode is a roadmap for any founder looking to exit with both financial return and community impact. 🔑 Key Highlights The Long Game: Peter's exit took 8 years - twice the time he spent actively running the business. He stayed in a governance role and planned a patient, values-aligned transition. First in Canada: Grantbook became the first Canadian company to officially transition to an Employee Ownership Trust on Jan 1, 2025. This structure ensures lasting impact and local wealth-building. The Emotional Return on Exit: For Peter, legacy outweighed liquidity. He prioritized a fair price while choosing a structure that would protect jobs, uphold mission, and keep culture intact. Mistakes Made and Lessons Learned: He reflects candidly on tax structuring choices that impacted capital gains exemptions - and offers advice for others planning ahead. New Chapter with Unwrapit: Peter is now growing a digital gifting company, Unwrapit, which aligns social impact with user choice and sustainability. Fun, Frank Advice from Peter Deitz: "Start early. The longer the runway, the more control you have. And if you go the employee ownership route, you'll be met by very happy employees - and a thriving community." ☕ Curious if an Employee Ownership Trust might be your best path forward? Book a 1:1 Wealth Gap Analysis with Colleen O'Connell-Campbell and map out your strategy. 👉 Connect via LinkedIn or email to get started. ⭐ Enjoyed this episode? Please leave us a 5-star review. Your feedback helps more founders discover how to exit on their own terms. *** 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.