You’ve been running the business for decades, and it’s been a hard slog.

You survived the ups and downs, including COVID, and lately the discussions have started about a possible sale.

It’s time, the family says.

It’s time, you tell yourself.

 

Things start happening: private equity firms knock on your door and express interest, or you engage with business brokers and M&A specialists.

Then it starts to become real: indicative term sheets, mandates.

You may never have thought about your business in these terms before. For all those years, it was what you did every day, and what paid for all the good things in your life.

But now it’s different. It’s an EBITDA multiple, or the present value of future flows. For you and your family, it’s potentially a large chunk of liquidity.

 

When push comes to shove and documents are there to be signed that actually move the prospect of a business sale forward, something is holding you back.

It’s hard to put your finger on.

The terms and the numbers all stack up.

Commercially, it makes sense.

Everyone you discuss it with agrees.

Yet something is holding you back.

And that doesn’t make sense.

 

Questions and doubts come to you:

– What will I do every day after the business is sold?

– Will the future owner look after things – the staff, the customers, the brand – the way I did?

– How will I invest the proceeds of the sale? I’ve never invested in that way before.

 

While these questions have something of a business lens, they come from a very different place – one that is not well considered when approaching business exit.

When making a business ‘exit ready’, we naturally think of the operational, financial and structural dimensions. But we don’t think about the emotional.

But starting a business is like having a child: we create it, it’s a part of us, and we watch it grow from business infancy to business maturity. Saying goodbye when we exit is hard enough; uncertainty about what the future holds makes it even harder.

 

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Over twenty years ago, I decided that I didn’t want to be an ‘owner-operator’ until the day I died (like my father). I set about steadily withdrawing from the business operationally, and establishing an advisory board so I could shift to ‘owner-investor’.

About ten years ago, I started building what has now become my third career as a family enterprise advisor.

Now, with the operating business only taking about 10% of my time, and the advisory business my primary focus, the thought of exiting the operating business carries no fear. My next chapter is written.

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Not everyone has the approach, the foresight and the time to plan their next stage of life.

My lived experience growing up in a business family and taking my own journey led me to become an advisor and help others experiencing similar challenges.

 

The greatest barrier to exit from your business might be the fear of uncertainty as to what comes next for you.

Rather than let those barriers hold you back, deal with the uncertainty and create the future you want for you and your family.

 

Conversation Starters:

How do you balance the needs of your business and your family?

What is the marginal benefit of remaining an owner-operator for another X years?

What does your next chapter of life look like?

 

Further Reading:

Family-Owned Business: Saying ‘Time to Go’
3 Challenges To Consider When Transitioning Your Family Business To A Third Party
4 Things About Investing in a Family Business
How to Successfully Transition a Family-Owned Business, According to The Colony Group
Is Succession In Founders’ Economic Interest?
Who Will Inherit the Family Business? Often, It’s Private Equity
‘My father’s succession planning took two decades – now I help other wealthy families’
How to Bring an Outside CEO into the Family Business
Workers Stick with Family Businesses for Generations, Family Business Study Finds
The Benefits Of Turning A Family Business Into The Business Of Family
Should You Treat Your Family Business Investment Like You Treat Your Stock Portfolio?

Your children are all equal, right?

But what does that mean in practice?

Consider some real-world examples:

You want to pay for your children’s university education. One does an arts degree, while another starts with a psychology degree, then does a master’s and now wants to do a PhD. How much do they each get for this?

You want to help each of your children buy a house – their primary residence. If things were ‘equal’, you might gift them each the same amount of money for this purpose.

But what if they live in different places with very different cost of housing? How many large homes with gardens can you buy in a nice suburb of Dallas for the same price as an apartment in central Paris?

What if they both live in the same suburb, but there is ten years age difference between them? What a house cost ten years ago would not get very much today!

Time is a very important ‘unequaliser’. One patriarch discussed with me the annual income supplement he gives his four children. From age 25, they each get a set amount each year. But there are eight years between eldest and youngest. I asked him if he indexes the amount for inflation. Now he does.

But even then, is it really equal?

What if the kids have different needs when it comes to housing? This is a great segue into a discussion about generation skipping. If your three children have zero, five, and two children respectively, do you split things ‘equally’ between them?

What if a family member has a medical condition? The family pays their expenses, but should other family members be financially equalised? It sounds absurd, but … (little surprises me anymore).

What if there’s a family business and some children are employed and some are not? Crafting good policies in that context is enough for a whole other article!

 

The bottom line is that equal means different things to different people.

And all our children are different, even if they are identical twins!

 

OK, so perhaps let’s aim for ‘fair’ instead?

That might make more sense. A ‘fair’ family policy might include supporting education costs, housing, medical, and an income supplement. The specific amounts distributed would still be a function of personal choice (what to study, where to live, how many children to have), and of some things that are outside anyone’s control (e.g. medical).

But … they would NOT be equal.

 

Fair is not equal, and equal is not fair.

 

What to do, then?

1. Accept the fact that children are different, and that you can’t direct equal outcomes for them.
2. Consider an approach of equal opportunity
3. Pursue fair and equal process.

That means family members participate in the process of determining policies like these. That gives them all a voice and the ability to debate tricky issues like the ones I’ve touched on (and more).

If they have a seat at the table where policy is set, then they can have a sense of ownership and buy-in of the policy. They can understand how hard this stuff is for parents.

Giving stakeholders a say in policies that affect them goes a long way.

 

Conversation Starters:

Who wrote your family’s distribution policy?

What elements of the policy continue to be a source of … discussion?

In what ways are your children different?

 

Further Reading:

New Study Finds Rich Boomers Are Stressed About Handing Down Fortunes To Their Kids
Passing on great wealth to our children spells the end of society. Just ask Aristotle
Fair should not be equal in a family-owned business
Boomers are planning their succession. Here’s the hardest question they face, according to a veteran generational wealth expert
The Rich Need to Navigate ‘Fairness Versus Equality’ Among Children
The Family Playbook: Preparing for the First Outside CEO
Opinion | A Good Life: My friends are inheriting piles of money and retiring early. I am not. How do I deal?

I can’t count the number of families who come to me with “we want to do things differently”.

Often, it relates to conflict in the previous/current generation that they want to avoid in current/future generations.

This is why the ‘mapping/discovery’ process is so important as part of onboarding a family.

It’s a bit like the way a doctor takes a medical history.

They might talk about conflict that only happened in their generation, but if you start to delve further back, there are often repeating patterns.

It doesn’t surprise me.

George Santayana famously said: “Those who cannot remember the past are condemned to repeat it.”

 

There are two elements to family conflict: fact and narrative.

The facts around a conflict can rarely be truly discovered. The truth is somewhere in between “our story” and “their story”. This isn’t a forensic judicial examination anyway.

What is more important is the narrative: how the conflict influenced the stories the family tells about itself. That in turn drives it engages with the world around it, and its wealth culture.

 

Family conflict is rarely about the commercials. It has its roots in basic family issues like fairness, favouritism, jealousy, and rivalry.

Seeking a commercial solution to an emotional problem isn’t going to work.

At best, it might patch things up temporarily, but it won’t address the root causes.

 

The same principle applies when considering repeating patterns.

If the pattern is viewed superficially – say in commercial terms – it won’t be understood.

The family may choose to change how things are done commercially, but that won’t address what’s really going on beneath the surface.

 

To break intergenerational patterns, families need to:

• Treat family members as humans, not saints. Growing up, we view our role-model and successful ancestors as infallible heroes. They aren’t. They are human just like us. Part of growing up and individuating is recognising that about our parents.
• Tell stories with honesty – warts and all. The saying goes “The older I get, the better I was”, but we all know everyone had ups and downs. Acknowledging that makes the stories more real, and better prepares us for what the world is really like.
• Be forward looking: what can we learn? There is little value in using stories to form judgement about the past. Rather, use them as a learning tool. How might we approach a similar situation? How might we do it better?

 

Albert Einstein said, “We can’t solve problems by using the same kind of thinking that created them.”

The first step to breaking intergenerational cycles is self-awareness.

A deep perspective on the past, plus a space for real communication about that can lead to a brighter future for the whole family.

 

PS Families of faith might find my Genesis of Legacy program of interest.

 

 

Conversation Starters:

What are the stories you tell of historical family conflict?

How have these stories influenced how things are done in your family?

 

Further Reading:

It’s ludicrous to blame Baby Boomers like me for the troubles faced by Millennials
How to help clients pass wealth down to next generation
Almost half of the ultra-rich haven’t figured out how to pass on their wealth, research finds
What happens to your brain when you become a billionaire
How to handle a sudden financial windfall
The Secret To Sustaining Intergenerational Wealth
Mastering intergenerational wealth transfer conversations with clients

I grew up in a family that had everything—except time.

My father was a Holocaust survivor who built a successful textile business from nothing. He worked tirelessly, overcoming unimaginable trauma with sheer determination. But my father refused to call himself a victim. He was a relentless optimist, focused on building a future. 

But that future came at a cost. 

I watched my father pace the factory floor, overseeing every decision. The business owned him, not the other way around. 

When I was old enough, I worked alongside him, feeling the weight of expectations—both my family’s and society’s. We were a prominent name in Melbourne, Australia, and with that came whispers, assumptions, and pressure. 

At first, I followed the script: I pursued a promising career in software development, then left the nine-to-five world to launch my own business. 

I craved independence, control, and success on my own terms. Over the years, I built multiple ventures, navigating the highs and lows of entrepreneurship. I learned what it meant to win—and to lose. 

Through all of this, one truth became clear: Time is the one asset you can’t earn back. 

 

Money, businesses, investments—these can be rebuild. But lost time with family, lost moments with community, lost opportunities for joy—these are gone forever. 

 

And yet, modern life conspires to steal time from us. We are slaves to technology, endlessly connected but never truly present. We confuse busyness with productivity, work with purpose. 

Then I saw something else: I had always known the solution. It had been in front of me my whole life.

I was raised in the Orthodox Jewish tradition of observing the Sabbath. For one day every week, I disconnected completely. No phone. No laptop. No work. Just time—time with family, with community, with myself. 

As a child, I found it restrictive. As an adult, I realized it was freedom.

The family charter or constitution is an essential governance tool.

How your family’s charter is written is as important as what’s in it.

 

I discovered this when the shoe was on the other foot – as my wife and I went shopping for a family enterprise advisor.

As much as I knew what our family needed, it could not be me: the role needs to be someone independent and external.

So we embarked on a process to choose someone suitable.

 

We interviewed a large MFO (multifamily office), a boutique MFO, a mid-tier accounting firm, and a specialist (like me).

After our discussion with the mid-tier accounting firm, I coined the term “McCharter”.

That was what they were offering: a process whereby family members would complete some surveys and forms and then – bing! – they would produce our family’s charter!

Wow! How convenient would that be?!

But alas, a document produced – no, manufactured – in that way is more akin to a Big Mac is exactly what a family does not want. Charters like this can do more harm than good.

 

Some people ask: what good is a family charter? It’s not legally binding.

 

But here is the key: the power of family charters is because they are not legally binding.

 

Whenever there is a legally binding construct, e.g. taxes, structures, what do we do? Pay expensive lawyers to do whatever needed to work around them!

 

If your family charter is a set of legally binding rules on the family, then family members may view them like the tax system: a regime imposed from a higher power where the mission is to pay as little tax as possible.

Is that how you want your family to run?

That approach is a lot like “ruling from the grave”, which rarely ends well.

 

A good family charter

• does not sit in the drawer with all the other contracts and agreements.
• is not handed to the family by the patriarch or matriarch like Moses coming down the mountain with the Ten Commandments.
• is not created by an accounting firm as the product of a questionnaire.

 

The process of creating a family charter is as important as the outcome.

The discussions the family has about what’s important: values, purpose.

The debates over proposed rules – asking why over and over to understand and then agree upon said rules.

These discussions need all stakeholders present.

They all need a voice, and to know that their voice is being heard.

And this can’t be done in a hurry.

 

A process like that will result in a charter with which everyone has buy-in.

It is not binding legally.

It’s far stronger than that: it’s binding by consensus.

It’s binding because the family agrees to be bound by it.

It’s binding because the family itself wrote the rules.

 

You can’t get that with a McCharter.

 

Conversation Starters:

What are the rules in your family?

Who set those rules?

How can the rules be changed?

Are they documented? How?

 

Further Reading:

A road map to designing an effective family meeting
You guard the soft side of the family business with a statute
Dentons identifies critical risk areas in annual family office survey report
Evolving governance: the role of structure in third-generation family businesses