One of the hardest decisions a business owner will ever face is knowing when it’s the right time to sell. For many, their business extends beyond merely a financial asset. It’s their identity, their legacy and often decades of effort and sacrifice. Yet every business eventually reaches a point where timing becomes critical: exit too early and you might leave value on the table; exit too late and risks or market shifts may erode hard-won gains.
Over the years, we have found that the reasons for selling, and therefore the timing, usually fall into three broad categories:
Personal drivers
Sometimes, the motivation to sell comes from life itself.
Age, health or the need to care for a loved one can suddenly make succession urgent. For others, it’s about legacy and the desire to see their creation live on beyond their direct involvement. At times, tensions between shareholders or family members make continuation challenging, while for others, it’s simply the pull of the next big adventure.
Business realities
Then there are moments when the business itself creates the need for change. Perhaps the owner no longer has the appetite to push for the next stage of growth. Or maybe capital is scarce and opportunities for expansion can’t be seized without external equity.
Sometimes, it’s about confidence, recognising that taking the ‘quantum leap’ to the next level requires skills or resources not currently within reach. External pressures also play their part such as tariffs, supply chain disruptions or disruptive technologies like AI that can shift the landscape quickly.
Market conditions
Thirdly, markets have their seasons. A spike in sector valuations can open a window of opportunity. Strategic players may be consolidating, or private equity firms may be rolling out ‘buy-and-build’ strategies. Or perhaps inbound interest arrives from a well-funded acquirer, creating the perfect chance to realise value.
The questions owners always ask
When it comes to timing, two questions almost always come up in conversations with business owners:
“What will I do with the proceeds?”
Replacing the income generated by a business isn’t easy. A diversified investment portfolio, while lower risk, will rarely match the returns of running your own business. That said, it does offer something many business owners haven’t experienced in years: peace of mind and reduced risk. For those seeking higher returns, post-sale wealth can also be channelled into private equity, private credit or even retained exposure by rolling some equity into the buyer’s vehicle. With the right advisers, it’s about designing a portfolio that balances risk, return and life goals.
“What will I do with my time?”
This one is harder. Many business owners are deeply passionate about what they’ve built. Selling can trigger an unexpected sense of loss, or even an identity crisis. Entrepreneurship is ‘sticky’ and it’s common for sellers to eventually re-enter the game, either by launching new ventures or backing others as mentors and investors. But finding purpose after an exit is not a financial decision. It’s an emotional journey that requires reflection well before the deal is signed.
Multiple shareholders, multiple agendas
Things can get even more complex when there are multiple shareholders involved. Personal goals may differ widely. One partner may want to cash out for retirement while another may want to double down for growth. These differences can lead to misaligned strategies and friction in the Board room.
At InterFinancial, we’ve developed a process called the Strategic Options Analysis to address exactly this issue. The process helps Boards and business owners to document each shareholder’s objectives, map out potential pathways (from sale to investment to M&A) and determine not just the ‘if’ but also the ‘when’. Just as importantly, it provides guidance on what can be done in the meantime to maximise value for all stakeholders.
Final thought
Timing an M&A exit is not about chasing the ‘perfect moment’. It’s more about understanding the intersection of personal readiness, business capability and market opportunity. And then, preparing meticulously to capture value when the stars align.
At InterFinancial, we’ve guided countless business owners through this journey. If you’d like to explore whether now is the right time or simply want to understand your options, reach out to Director Anuk Manchanda to start the conversation.
