Tom Murray, Managing Partner and Head of Insolvency at Friel Stafford, has sat across the table from business owners at every stage of the selling journey. And there is a pattern he believes does not get talked about enough: the decade you choose to sell in matters almost as much as the business itself.
Sell in your fifties and you are negotiating from strength. You probably have another ten or fifteen working years in you if the deal falls through, so you do not actually need this sale. Buyers can sense that. It buys you leverage on price, on deal structure, on how much of an earn-out you are willing to accept, and on how long you are prepared to stay on and hand things over properly.
Sell in your sixties and the maths starts to shift. You are still fit, still sharp, still capable of running things for a few more years. But buyers know your runway is shorter than it was, and both private equity houses and trade buyers will price that in. Family members in the business start asking when you plan to step back, and that question, asked often enough, erodes your negotiating position from the inside.
Sell in your seventies and more often than not you are selling because you have to, not because you chose the moment. Health becomes a live factor. Key relationships built over decades start to fray as you become less present. And in Ireland, the tax position turns against you. Since 1 January 2025, retirement relief on capital gains tax runs at full strength right through to age 69: up to €750,000 tax free on a sale to a third party, or up to €10 million on a transfer to a child, with value above that level qualifying for a deferral where the child retains the assets for 12 years. Turn 70 and those thresholds fall to €500,000 and €3 million respectively. That is a cliff edge, not a gentle slope, and I have spoken with owners who found it out the hard way.
None of this means you cannot sell well at 68, or even 74. Plenty of people do. But every year you delay past your fifties, you quietly trade away optionality. Fewer buyers will wait around for a longer handover. Banks get more cautious about backing a management buyout if your health or energy becomes a talking point in due diligence. And the tax rules eventually turn from friend to obstacle.
The other thing I see, particularly with Irish family and owner-managed businesses, is owners assuming that selling means a stranger walking through the door. It does not have to. A management buyout, where the team who already know the business take it forward with the right finance behind them, is often the smoothest deal to do, because both sides already trust one another. It keeps the culture, the staff and the client relationships intact. A trade sale to a strategic buyer is the other route, and for the right business it is absolutely the correct one. The two are not mutually exclusive either. We often run a process that tests both at once, so the owner is not locked into one path before knowing what the business is genuinely worth.
If you are in your fifties or early sixties and even loosely thinking about an exit, that is the moment to start planning, not the moment you finally decide to sell. Valuations, deal structures and successor readiness all take time to get right, and rushing them at 68 rarely ends well.
If any of this sounds like where you are, Tom Murray and the team at Friel Stafford are happy to talk it through. Simply get in touch.