For many entrepreneurs, this is the hardest part
Download PDF VersionNine days after selling his company for £42 million, one entrepreneur found himself locked out of his own email account.
For nearly two decades, somebody else had dealt with these things. There had always been an assistant to call, an IT department to reset passwords, a finance director who knew where documents were. Now there was only him standing in the kitchen of his house in the Cotswolds, repeatedly typing the wrong password into a laptop while his wife asked whether he wanted a cup of tea.
“It was the first moment,” he told me later, “when I thought: oh wow, it’s actually over.”
“Suddenly there is nowhere they need to be on a Monday morning”
People who have never built businesses tend to imagine a company sale as a clean finish line: the founder exits, the money arrives, life improves. In reality, the period immediately after a liquidity event is often untidy and unnerving. Entrepreneurs who have spent many years being needed by everybody suddenly discover that there is nowhere they need to be on a Monday morning.
By the time completion arrives, most founders are exhausted. For months they have existed inside a world of lawyers, calls, and negotiations, while simultaneously running the business. I compare it to trying to perform open-heart surgery on yourself while running a marathon.
When the sale finally does go through and the cash comes in, entrepreneurs often describe feeling ejected out of the whole intense process and left on their own.
Many founders describe the period afterwards as one of dislocation. The structure that governed their adult life has disappeared almost overnight. One former software founder told me that, after selling his business, he continued waking at 5.15am every morning for six months despite having nowhere in particular to be.
Another entrepreneur told me that for months after selling his business he still reached for his phone every Sunday evening expecting a problem waiting for him on Monday morning. There never was.
This is usually the point at which the practical concerns begin to surface. How much can we actually spend? Should we move? What do we tell the children? Who can be trusted? What happens if something happens to me? How do I look after my partner and the children? What should I do next?
They are important questions, but they tend to arrive at precisely the wrong moment: when the entrepreneur is exhausted. It is the perfect moment to do something most entrepreneurs find deeply uncomfortable: stop.
I have worked with entrepreneurs for more than three decades and count myself among their ranks. While we are all different, there are several common denominators I have seen crop up frequently. Unsurprisingly entrepreneurs are driven, optimistic, willing to take on risk, and are used to momentum. Which is why sitting by a pool on holiday and reading a novel feels so unnatural. Yet a pause is often exactly what is needed.
“After a sale, for the first time in many years, there may be no obvious next step.”
Whether it is market volatility, a difficult negotiation, a late-stage wobble in the sale process, these are familiar challenges that may irritate, but rarely frighten an entrepreneur, provided there is a reason and a plan. What feels far more unnerving is the absence of a plan. And after a sale, for the first time in many years, there may be no obvious next step.
This is the point at which entrepreneurs have to resist doing what has always worked before. In business, action solves most problems. After a liquidity event, premature action often creates them. The family office, the philanthropy, the investments, the houses, the tax planning, the children’s futures, none of it needs to be decided immediately.
A holiday is not an escape from responsibility; it is often the first sensible act of it. Go away, sleep, and be with your family, and let the transaction leave your system. Then come back ready to begin the next job, which is not running the company anymore, it is becoming the CEO of the rest of your life.
It does not go more wrong than choosing the wrong team. Until now, the entrepreneur has usually been the expert in the room. Following a liquidity event, they find themselves navigating an entirely new discipline: managing significant personal wealth.
There are six common mistakes that can make the transition unnecessarily difficult.
One of the first questions entrepreneurs ask after a liquidity event is whether they have enough money. The thought process is usually straightforward. Have I looked after myself and my partner? Can we maintain the lifestyle we want? Will we ever need to worry about money again? In most cases, these questions can be answered relatively quickly. The analysis is done; the numbers are run and a plan put in place. What follows is often far more interesting.
Once entrepreneurs are comfortable that they and their partner will be financially secure, attention tends to shift towards the wider family. Questions around children, inheritance, and legacy begin to surface. How much is enough? What should the children know, and when should they know it? How do you create opportunity without removing ambition? How do you prepare the next generation to be responsible custodians of wealth?
These are more challenging questions because they relate to values, family, and purpose and there is no spreadsheet on earth that can answer them.
In my experience, concerns around children, legacy, and the next generation are among the strongest themes to emerge following a liquidity event. Entrepreneurs who have spent decades building businesses often find themselves turning their attention towards something entirely different: building a framework for the future of their family, which is where a clear process becomes invaluable.
The reason our 'CEO of the rest of your life' framework resonates so strongly with entrepreneurs is that it follows a structure they are already familiar with. Successful businesses are built around clear objectives, the right people, disciplined execution, and regular review. Life after a liquidity event requires the same level of thought.
At this stage, most entrepreneurs need somebody to help bring structure to what can feel like an overwhelming number of decisions. Tax advisers, lawyers, investment managers, and trustees all have important roles to play, but somebody needs to ensure they are working towards the same objectives.
That is where a family office can add real value, helping families translate aspirations into a coherent strategy and then ensuring it is implemented over time.
Through our four-stage bespoke approach, beginning with Discovery, moving through Design and Execution, and ending with ongoing Optimisation, we ensure individual decisions support your wider plan.
As CEO, you set the long-term direction and are responsible for all critical decisions. Our role is akin to COO or CFO, the disciplined engine that translates your vision into execution, providing the network, knowledge, and oversight to move you from where you are to where you intend to be. The result is a system that integrates your personal, familial, and financial aspirations and objectives under one roof.
“Building the business may have been the achievement that created the wealth. Becoming the CEO of the rest of your life is about making sure it serves the purpose for which it was created.”
For many entrepreneurs, selling the business feels like the finish line. In reality, it is often the beginning of a very different journey.
Once the deal is done and the excitement subsides, attention turns to the questions that matter most: how to look after your family, how to organise the wealth you have created, and what you want life to look like from here. This is where the focus shifts from building the business to shaping everything that comes after it.
CEO, Cavendish Family Office
