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EP317 Navigating Tax Complexities for a Cash-Rich Business Exit

The Cash Rich Exit Podcast

Release Date: 03/25/2025

EP 334  Purpose, People, and the Art of Letting Go show art EP 334 Purpose, People, and the Art of Letting Go

The Cash Rich Exit Podcast

In part two of this insightful two-part conversation, host Colleen O’Connell-Campbell reconnects with Elizabeth Kilvert, founder of ‘The Unrefined Olive’, to go deeper into how she built, grew, and ultimately exited a purpose-driven business.   Elizabeth shares her candid reflections on:   Transitioning from founder to seller - and how she knew the timing was right. The emotional side of stepping away from a business built around community and values. How staying connected to purpose helped her navigate both growth and exit with integrity. What she learned about...

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EP333 From Olives to Ownership - Finding Purpose in Entrepreneurship show art EP333 From Olives to Ownership - Finding Purpose in Entrepreneurship

The Cash Rich Exit Podcast

In this episode, Colleen O’Connell-Campbell sits down with , 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...

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EP332 Unlocking Legacy and Liquidity - Exit Strategies for $5M-$50M Businesses show art EP332 Unlocking Legacy and Liquidity - Exit Strategies for $5M-$50M Businesses

The Cash Rich Exit Podcast

💡 Episode Summary In this episode, host sits down with - Managing Director at Shaughnessy Group and a seasoned corporate finance and M&A expert. Karl brings decades of experience helping mid-sized, often family-owned Canadian businesses (with revenues between $5 million and $50 million) navigate their most important transition: the sale of their company.   They explore what makes this “overlooked middle” of the market so unique, why selling isn’t like selling your house, and how strategic planning years in advance can unlock both legacy and liquidity. Karl also shares...

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EP331 Be the Owner, Not the Renter - Building Brands That Last show art EP331 Be the Owner, Not the Renter - Building Brands That Last

The Cash Rich Exit Podcast

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...

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EP330 Building, Selling, and Thriving Beyond Business show art EP330 Building, Selling, and Thriving Beyond Business

The Cash Rich Exit Podcast

Serial entrepreneur Ed Hansen joins host Colleen O’Connell-Campbell on the Cash Rich Exit Podcast to share his decades-long journey founding, scaling, and selling multiple businesses - including Hanson Lawn and Gardens and . In this episode, Ed reveals how mindset, adaptability, and a focus on relationships have shaped his entrepreneurial path.   Key takeaways: The early entrepreneurial spark - from cutting grass to building a multi-million-dollar company. Buying vs. selling a business - why every transaction is unique and how to make sure both sides win Building for a future exit...

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EP 329 Strategic Partnerships and Real Estate Insights show art EP 329 Strategic Partnerships and Real Estate Insights

The Cash Rich Exit Podcast

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...

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EP328 Intentionality, Identity, and the Exit Journey show art EP328 Intentionality, Identity, and the Exit Journey

The Cash Rich Exit Podcast

What happens when your exit strategy is about more than just money? In this episode, host Colleen O’Connell-Campbell talks to April Harbottle, a highly experienced M&A advisor and business transition specialist. April has spent years helping small and mid sized business owners unlock the value of their companies and transition successfully, whether through exits or by scaling with new partnerships.   Together, they explore how values, identity, and leadership evolution shape the founder journey - especially when it's time to let go.   🔍 Key Highlights   Start with an...

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EP327 Rethinking Succession - Why Employee Ownership Might Be your Legacy Move show art EP327 Rethinking Succession - Why Employee Ownership Might Be your Legacy Move

The Cash Rich Exit Podcast

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 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...

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EP326 Identity, Reinvention and Entrepreneurial Grit show art EP326 Identity, Reinvention and Entrepreneurial Grit

The Cash Rich Exit Podcast

In this candid and energizing episode of ‘The Cash Rich Exit Podcast’, host sits down with author, educator, and tech entrepreneur . From academia to publishing to leading a fast-scaling SaaS platform, Lindy shares her story of transformation and what it really takes to walk away from one professional identity to build another.   Together, they dig into what motivates bold career pivots, the value of knowing your numbers (and knowing your worth), and how to preserve optionality - especially as a woman founder in Canada.   🔑 Key Highlights   Why letting go of sunk cost...

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EP325 A Scenic Exit - How Peter Deitz Turned an Eight-Year Journey into Shared Prosperity show art EP325 A Scenic Exit - How Peter Deitz Turned an Eight-Year Journey into Shared Prosperity

The Cash Rich Exit Podcast

In this episode, host 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...

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More Episodes

Taxes may not be the most exciting topic, but mastering tax planning is crucial for entrepreneurs aiming for a cash-rich business exit. In this insightful episode, host Colleen O’Connell-Campbell sits down with Mike Nazarov, a seasoned tax partner at KPMG Canada, to decode Canadian tax updates and share essential strategies for structuring your Canadian-controlled private corporation.

 

Here's what you can expect from this episode: 

 

🔑 Practical insights into the recent capital gains inclusion rate changes in Canada. 

📈 Tips for optimizing your business structure for maximum tax efficiency. 

🏢 Understanding the vital role of proactive tax planning in business transitions. 

💼 Why your corporate structure should evolve alongside your business goals.

 📆 Guidance on how frequently you should review and update your tax strategy.

 

Mike shares actionable advice to help you navigate the complexities of tax planning, ensuring you're positioned for success whether your exit strategy involves selling to a third party, transitioning to family, or planning for unexpected events.

 

Don't miss Mike's fun, frank advice on building your business "A-Team" - the essential experts every entrepreneur needs in their corner.

 

🎧 If you enjoyed this conversation, please leave a 5-star rating and review - it helps us continue to bring valuable insights directly to entrepreneurs like you!


Let's stay connected! Reach out to Colleen O’Connell-Campbell on LinkedIn for personalized guidance and to explore a 1:1 Wealth Gap Analysis to get you on track for your own cash-rich exit.

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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.