Challenges of founders letting go
Almost every family we serve built their wealth by controlling a portfolio of operating businesses or real estate. They did not inherit it, get lucky, or do it as a minority investor. They steered the ship through storms, closed deals, kept clients and negotiated with investors, and they saw the direct result of that effort compound over time.
Control is what made them wealthy. So it is natural for a founder worth $100M to want to stay in the driver's seat, and handing any of it over to someone else is not an enjoyable process.
What holding on looks like
Before most families build any structure, the wealth creator sits in the middle with direct lines out to five to seven advisors who do not speak with each other more than once a year. Everything runs through one person.
I have been on retainer with a $175M family for over three years, and they have been time broke the entire time. We ran a search and found an excellent executive assistant, and they never made the hire. They still listen to their own voicemails and answer their own email. They will likely become billionaires over the next decade, and they have far more chaos and friction than they need.
Holding on rarely looks like a fight. It looks like a founder still doing work someone else should be doing.
Operator mode and owner mode
When I interviewed Tony Robbins for billionaires.com, he described two ways to operate: operator mode and owner mode. In operator mode he worked harder at $10M in revenue than he does now as an owner in more than 100 companies.
I know more than 100 doctors and dentists who work as many hours as the $100M and $1B families we serve, and probably harder. They are in operator mode, and you cannot scale that way. It is not about how many hours you work. It is about time leverage, and using the specialty skills of people who are much better than you at specific things.
It is who, not how. That idea comes from Dan Sullivan and his book Who Not How. I was in his highest level program, at $50,000 a year, for years. For many problems you do not need to spend 400 hours figuring out how. You need to figure out who. Ask yourself what you could automate, delegate or eliminate to free up your time for what you add the most value to.
In our own business, I architect the work and our team carries out the hundreds of hours it takes to get done. We have hired over 100 people on Upwork, and we have full-time team members in the Philippines and Colombia running our deal origination process. That is the evolution from working in a business, to working on your business, to working on your businesses. It is also how a family office operates.
Holding on to the wrong people
The most costly mistake Tony named was staying too long with people who are not right. That has probably cost our company millions of dollars in revenue. We held on to bad salespeople way too long, and they were toxic to our culture. We have gotten much better at it. You cannot be a high velocity company if you are hanging on to the wrong people.
When control meets the next generation
Control runs through the family too. I know family members who do not talk to each other because the brother was not trusted with the money, and then they lost most of it. Many families come to me trying to solve the same headache: they want control, and they need to pass wealth on to the next generation.
One family with $850M came to me because the second generation was taking over and only one person had been appointed to manage all of it. That one person was hiring and firing fund managers, trading stocks and bonds, running reporting and coordinating real estate. Handing everything to a single successor rebuilds the same bottleneck one generation later.
What to put in place before you step back
How I am doing this with my own daughters
I grew up in the Boy Scouts reciting the Boy Scout Law. I realized my girls did not have anything like that, so we wrote our own family values. They hang above our kitchen table, and the girls earn fun tickets when they live them. If I did it again, I would choose five values instead of a dozen, so they are faster for kids to memorize.
I bring my children into our office and tell them stories about what is happening in the business and how it got to where it is. I try to bring one of my daughters to each of our summits. Members can bring a son or daughter to our events at no cost, because they will learn things there they will not learn at school.
My dad used to frame it this way about work in general. When you waste the money, you are wasting the years of their life it took to build it. He raised $1 billion for non-profits before I ever started this, so I heard it from someone who had spent the years.
It is more important to pass on your values to your kids than your money. If you pass on just the money, you might ruin them and take away their motivation. If you pass on just the values, they may make the money. If you pass on both, they may lose the money, but they can make it back.
