The business sale blueprint: Planning beyond the sale price

But the sale price is only part of the story. Without the right planning, even a great sale can leave you with unexpected taxes, lifestyle questions, or a disconnect between the success you’ve built and the legacy you want to leave behind. 

Selling your business is a major milestone. It’s a chance to turn years of hard work and sacrifice into long-term security for you and your family.

But while most business owners focus on what they’ll get for the business, few think about what comes next.

The truth is: the sale price is only part of the story. Without the right planning, even a great sale can leave you with unexpected taxes, lifestyle questions, or a disconnect between the success you’ve built and the legacy you want to leave behind.

We help business owners turn their sale into more than just a transaction. We help them turn it into a plan for the future.

Why planning before the sale matters

The best outcomes don’t happen by chance. They come from planning early, before the sale is even on the table.

Here’s why:

• Many owners don’t know what they actually need from the sale to fund their post-sale lifestyle, and many haven’t even determined what they will require on a monthly or yearly basis for retirement spending, travel, and support for family.
• Taxes can eat up to 25 to 30% of your sale proceeds if you’re not prepared.
• Once the sale is complete, it’s often too late to make important changes.
   

Pre-sale modeling gives you clarity. It helps you understand:

• What your business is worth today.
• What you’ll need to live the life you want.
• How different deal structures impact your tax bill and future income.
   

In a study from the Exit Planning Institute, 76% of owners who sold their business regretted it within a year – not because of the sale price, but because they hadn’t planned what would come next.¹

A blueprint for success: What to plan for before and after the sale

1. Pre-sale financial modeling: What’s enough?

Start with a simple question: Do I have enough to retire and live the life I want?

We work with you to create a full financial projection based on your goals: travel, time with family, philanthropy, and more. This helps define the amount you actually need to walk away with.

And sometimes, it shows you that you can slow down and step back sooner than you thought.

2. Tax planning: Keep more of what you’ve built

A well-structured sale can reduce your tax bill dramatically. That means more money in your pocket to use, give, or grow.

We work closely with your tax advisor to model how commonly used tax planning strategies can impact your financial future. By integrating these strategies into your long-term projection, we help you clearly see how decisions made today will shape your post-sale income, lifestyle, and legacy.

Some of the strategies we help model in collaboration with your tax advisor include:

• Use of the Lifetime capital gains exemption for Canadian business owners (up to $1.25 million as of June 25, 2024).²
• Freezing shares and introducing a family trust before the sale, which fixes the value of your business’ shares as of a certain date, and passes any future growth onto your family members.
   

In addition to modelling these structures, we also provide support on:

• Splitting income with a spouse or adult children.
• Philanthropic giving to offset capital gains.
   

These strategies can significantly affect your long-term outcome – but only if they’re accurately reflected in your plan. That’s where we come in.

It’s also important to note that every business is different. The earlier we start working with your tax advisor to integrate these strategies into your plan, the more options you’ll have – and the more confident you’ll feel in your decisions.

3. Post-sale lifestyle planning: What’s next?

Most business owners aren’t just worried about money. They’re thinking about purpose.

You’ve poured your heart, soul, and hard work into your business, and after you sell it, it’s natural to feel uncertain about what’s next. What will you do with your time? How will you stay connected to your community or industry?

We help you answer these questions with intention. Whether it’s launching a new venture, mentoring other business owners, spending time with family, or giving back, we help you define your next chapter.

4. Wealth transition: Creating a legacy that lasts

For many business owners, the sale isn’t just about themselves. It’s about the next generation.

You may want to:

• Support your kids and grandkids.
• Help them buy homes or start businesses.
• Teach them how to be good stewards of wealth.
• Give back to the causes you care about.
   

We help families think through these decisions with care. That might include:

• Setting up family meetings to talk about values and vision.
• Creating Donor-Advised Funds for strategic giving.
• Building multi-generational trusts to protect and preserve family wealth.
   

Why us?

We have decades of experience working with business owners. Many of our clients are first-generation entrepreneurs who built their wealth through hard work and smart decisions. We work hard to honour that legacy by helping them make the most of it, not just in the sale, but in the years that follow.

We collaborate closely with your accountants, legal team, and family – bringing everything together in one integrated plan.

Because your life’s work deserves more than a sale. It deserves a future.

Ready to get started?

Whether you’re thinking about selling next year or five years from now, it’s never too early to start planning.

Let’s talk about what matters most to you – and build a blueprint that goes beyond the price tag.

Your future starts with a conversation. Let’s talk.

Sources

Emotional considerations for transitions. April 1, 2018. Exit Planning Institute. https://blog.exit-planning-institute.org/emotional-considerations-transitions.  

Capital Gains – 2024. February 28, 2025. Government of Canada. https://www.canada.ca/en/revenue-agency/services/forms-publications/publications/t4037/capital-gains.html.