1. Understand how Canadian businesses can prepare for generational wealth transition.
2. Gain practical tips on business succession, valuation, and managing complex family dynamics.
3. Reflect on the emotional side of entrepreneurship and how legacy planning shapes the future.

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• Canada’s business environment has undergone several changes in recent years.
• Entrepreneurs have faced challenges from the pandemic, supply chain disruptions, inflation, and staffing shortages.
• Despite uncertainty, Canadian businesses continue to show strength and adaptability.
• Iain Gallagher believes that resilience and optimism still define today’s entrepreneurs.

• More Canadians than ever aspire to start their own businesses.
• Younger entrepreneurs are blending creativity with technology to reshape traditional industries.
• Many are bringing fresh perspectives through lifestyle, wellness, and tech-driven ventures.
• Iain highlights the growing impact of immigrant entrepreneurs on Canada’s business growth.

• Today’s business owners must embrace technology from day one.
• Digital tools now drive marketing, sales, and operations, reducing costs and improving efficiency.
• Strong financial systems are vital to support decision-making and sustainable growth.
• Iain explains how modern entrepreneurs can scale faster by leveraging digital solutions.

• A large wave of Canadian business owners plans to retire within the next decade.
• This generational shift poses both risks and opportunities for the economy. It also presents personal challenges for some entrepreneurs.
• Iain emphasizes the need for families to have open discussions about business succession plans.
• Preparing early helps avoid rushed transitions and protects the value of the business.

[09:40] Iain: “What we really try and encourage our clients to do is have those conversations and really talk about what everyone's goal is and what's the best way of achieving that.”

• Even if a sale is years away, owners should start preparing now.
• Iain outlines three key steps: strengthen financial reporting, delegate management, and share client relationships.
• Letting go of control allows teams to grow and businesses to operate independently. 
• Many entrepreneurs misunderstand the true value of their business, making preparation even more critical.

[12:20] Iain: “As the business matures, grows, the number of people you have working for you increases. Owners really have to take a step back.”

• Strong financial systems, clear reporting, and solid management make a company more attractive and valuable to buyers.

• Selling a business is deeply personal for most entrepreneurs.
• Owners often see their company as part of their identity and community.
• Iain discusses the emotional attachment and the importance of defining success beyond price.
• Planning for employees’ future and preserving the founder’s legacy helps ease the emotional transition.

• A smooth business succession comes from preparation, clarity, and self-awareness.
• Owners must decide what they want their role to be after the sale.
• Iain compares selling a business to selling a home. Presentation and readiness matter to potential buyers.
• Making small operational and financial improvements can significantly boost value.

• The right advisors can make or break a transition.
• Iain stresses the importance of having accountants, lawyers, and M&A experts involved early.

[21:43] Iain: “We couldn't do what many entrepreneurs do, but similarly, they can't do what we do. So we really encourage people to get the right advisors around them and identify them early on, because again, never want to think of an entrepreneur, business owner, a family, being pushed into transactions when they're not prepared.”

• Long-term relationships with trusted advisors help owners make informed decisions.
• A strong advisory team ensures both the business and shareholders are ready when the opportunity to sell arises.

• Selling a business creates a new financial reality for entrepreneurs.
• Many owners need guidance to manage newfound wealth and plan for the next phase.
• Iain explains how collaboration with financial planners, tax experts, and family members can align goals.

• Carissa closes the episode by highlighting the dedication and resilience of Canadian business owners.
• Early planning and honest conversations can make every transition smoother and more meaningful.
• Each step, from preparation to letting go, helps shape a lasting legacy.
• Thoughtful decisions today can secure success for both current and future generations.

Connect with Carissa Lucreziano on LinkedIn.

Iain Gallagher is the Managing Director and Head of Mid-Market Investment Banking at CIBC. With more than 25 years of experience, he has helped Canadian entrepreneurs navigate business succession, sales, and transitions. He focuses on helping owners realize the full value of their companies. Iain also ensures that the legacy they’ve built is protected. His experience covers industries like manufacturing, distribution, technology, and services.

Known for his thoughtful approach, Iain understands the emotional side of every business transition. He also recognizes the financial complexity that comes with it. He works closely with families and founders to ensure each step of the process reflects their goals and long-term vision.  Through his leadership, he supports the next generation of Canadian business owners. He helps them plan with confidence, grow their businesses, and adapt to change.

Connect and learn more about Iain Gallagher on his LinkedIn.

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Have any questions? You can connect with me on LinkedIn or through CIBC’s Facebook,or Instagram.

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