EP 2: Tax Planning Opportunities and Pitfalls for Business Owners in 2024 With Matt Holmes, CPA

Are you a business owner approaching retirement or just starting to think about a future sale?

In this episode of Retirement Planning Simplified, Joe sits down with Matt Holmes, partner at Homes Riseleys CPA, to uncover the biggest mistakes business owners make when it comes to succession planning and selling their business and how to avoid them. He explains new tax rules for 2024 and how they can affect business sales, including updates to the capital gains exemption, AMT, and anti-avoidance legislation. 

Matt brings decades of tax and structuring experience to this conversation covering everything from tax-saving strategies to real-life horror stories of owners who waited too long to plan. 

Here’s what you’re in for:

00:00 Common Mistakes in Business Value Creation

04:26 Importance of Planning for Unexpected Sales

07:28 Successful Business Transitions

11:07 Structuring and Tax Advisory for Business Owners

20:34 Nuances of Selling to Family vs. Third Parties

25:30 New Rules and Legislation for 2024

32:48 Conclusion

 

ABOUT MATT HOLMES

Matt Holmes is a seasoned tax advisor with over 25 years of experience helping small to medium-sized business owners achieve their goals through tailored business, tax, and accounting strategies. A Chartered Accountant and graduate of Ryerson University, Matt specializes in corporate reorganizations, estate planning, and succession strategies for owner-managed businesses across industries like healthcare, real estate, and tech. His expertise lies in tax minimization and wealth maximization, particularly during business transitions, sales, and generational transfers.

You can reach out to Matt through:
LinkedIn:https://www.linkedin.com/in/matt-holmes-15294b14

Website: https://www.holmescpa.ca (Company)

 

ABOUT JOE  CURRY

Joe Curry is the host of Business and Exit Planning Simplified and the owner and lead financial planner at Matthews + Associates in Peterborough, Ontario. A Certified Financial Planner and Certified Exit Planning Advisor, Joe is passionate about helping business owners maximize value, plan successful exits, and find purpose beyond their business. His mission is to ensure clients retire with confidence—financially secure and personally fulfilled.

You can reach out to Joe through:

LinkedIn: https://www.linkedin.com/in/curryjoe

Website: https://www.retirementplanningsimplified.ca/

  https://www.facebook.com/RetirementPlanningSimplified/

               https://matthewsandassociates.ca/ 

 

ABOUT BUSINESS AND EXIT PLANNING SIMPLIFIED

The Business and Exit Planning Simplified podcast offers clear, actionable guidance to help business owners maximize value, plan successful exits, and achieve financial freedom. Hosted by Joe Curry, a Certified Financial Planner and Certified Exit Planning Advisor, each episode delivers expert insights, real-life case studies, and practical strategies tailored for service-based entrepreneurs approaching retirement. The podcast empowers listeners to transition with clarity, confidence, and a renewed sense of purpose.

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Disclaimer:

Opinions expressed are those of Joseph Curry, a registrant of Aligned Capital Partners Inc. (ACPI), and may not necessarily be those of ACPI. This video is for informational purposes only and not intended to be personalized investment advice. The views expressed are opinions of Joseph Curry and may not necessarily be those of ACPI. Content is prepared for general circulation and information contained does not constitute an offer or solicitation to buy or sell any investment fund, security or other product or service.