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When it comes to selling a business, timing is everything – but it’s not just about the market. Often, the most powerful motivators for a sale come from within. Whether it’s a desire for change, a sense that your business is peaking in value, or a personal milestone like financial independence, internal factors can play a major role in guiding your decision. In this blog, we explore some of the most common internal reasons why entrepreneurs consider selling – and why in 2025. With shifting tax laws and evolving buyer expectations, it might be time to act.
1) You’re feeling restless
Do you find yourself asking “what’s next”? According to an RBC Small Business Poll, 65% of current or aspiring business owners in Canada say that they “peaked” in their career – and that starting or owning a business was the logical next step to continue growing professionally. This highlights a strong desire to move from one goal to the next[1].
Over time, our personalities and interests evolve. Maintaining the same level of commitment and passion over the long-term is difficult. It’s natural to want to explore new opportunities, and to feel the need to seek out new challenges. Trust your gut – if you feel that it’s time for a change, it just might be.
2) Your business has value today
You’ve poured all your blood, sweat, and tears into the business, and it’s finally financially where you want it to be. Sure, you may want to breathe a sigh of relief, but you may also want to consider striking while the iron is hot. An opportunity to gain liquidity is always worth considering, and it would be best to consult with your trusted Zeifmans advisor before making any potentially risky moves.
It’s also worth noting that in today’s market, buyers are becoming more selective. In many sectors, valuation multiples are under pressure in 2025 due to rising capital costs and a more cautious approach from investors. Companies without strong profitability or intellectual property protections may face tougher negotiations. Preparing your business for sale – ensuring robust financials, clear customer acquisition metrics, and tax-efficient corporate structures – has never been more important.
3) You have a buyer in mind
If you’ve put the time in to grow your business and establish sturdy systems run by great teams, you may find yourself in a position where a buyer presents themselves under favourable circumstances. If an interested party aligns with your own personal timing or is willing to conduct a purchase in a way that is more beneficial to you from a tax perspective (for instance, purchasing shares instead of assets), it is worth considering the option of selling.
4) You’ve achieved long-term financial security
For many entrepreneurs, the goal of starting a business is to create a stable financial future for themselves and their families. However, many entrepreneurs receive so much joy and meaning from the work itself that they lose sight of this original goal and continue to work several years beyond achieving financial stability. Work can make life sweet, but so too can retirement. If you have built up a state of wealth that could carry you into the future, you may consider selling your company in order to step into a more laid-back lifestyle and begin your next chapter.
5) A shifting tax landscape
Taxation is an integral facet of any sale scenario. As of 2025, Canada’s capital gains tax rules are in a state of flux. The 2024 Federal Budget proposed an increase in the capital gains inclusion rate from 50% to 66.67% for individuals on gains above $250,000, and for most corporations and trusts. However, this change has not yet become law. The federal government has stated that legislation to implement the new rate will be introduced “in due course,” and the most recent update confirms the new rate will not take effect before January 1, 2026 – at the earliest. Until then, the CRA will continue applying the current 50% inclusion rate [2].
This uncertainty highlights the importance of proactive tax planning. Strategies such as utilizing the lifetime capital gains exemption or implementing an estate freeze may be more relevant than ever. If you believe that tax rates may rise or planning opportunities may narrow in the future, it could be prudent to act now. Be sure to consult with a tax advisor, who can help tailor a strategy to your unique circumstances and provide the most up-to-date guidance.
Seeking guidance on a sale
Ultimately, your decision to sell will depend on your other options as well. What will you do if you don’t sell your company? Will you keep the business? Will you find someone to replace you? Will you shut the business down? What will the after-tax result of a sale be? Keep in mind that if the deal is not properly structured, a higher sale price may not result in more money in your pocket after taxes.
Measuring the attractiveness of a sale depends on a number of factors that combine like puzzle pieces to create a full picture. That’s why it’s helpful to speak with a knowledgeable advisor, who can assist you in gaining perspective on your options and weighing the cost/benefit of a sale. The team at Zeifmans has decades of experience assisting entrepreneurs as they navigate their biggest business decisions throughout the course of the business life cycle – from inception through to sale. If you’re wondering whether now might be the time to sell your startup, contact one of our professionals today at info@zeifmans.ca to get the conversation started.
[1] RBC, “RBC Small Business Poll reveals Canadians are turning to entrepreneurship for financial security and career autonomy” RBC Small Business Poll reveals Canadians are turning to entrepreneurship for financial security and career autonomy – My Money Matters
[2] Government of Canada, “Government of Canada announces deferral in implementation of change to capital gains inclusion rate” Government of Canada announces deferral in implementation of change to capital gains inclusion rate – Canada.ca
