The QB Nobody Hired
You can't see the whole terrain from the valley floor.
A little while back I was having a glass of wine with a founder I know. Successful guy — runs several companies, sharp operator, the kind of person who makes complicated things look manageable.
He was telling me about some exciting things happening in his business. He’s working on restructuring his HoldCo — building out a proper structure with a corporation to hold assets and a separate management corp to run operations. Smart moves. The kind of planning that sets a business up properly for what comes next.
As he was walking me through all the moving parts, something shifted in the conversation.
He started listing the people involved. The lawyers and accountants tied to his active companies. The different lawyer handling his personal side. The separate accountant for his personal finances. The private banker. Running from one to the next, making sure each one had what they needed, translating between them, keeping the whole thing moving.
He paused mid-sentence.
“I’m basically the CFO of my own personal life, aren’t I.”
It wasn’t really a question.
The thing is, he’s not unusual. Most founders I sit with are running the same play — they’ve built a capable team around them, everyone is doing good work, but nobody has been given the job of looking at the whole picture. So by default, that job falls to the founder.
And it’s expensive. Not just in dollars — though the missed opportunities and gaps between advisors have a real cost — but in time and mental energy that should be going somewhere else.
Think about what it actually takes to coordinate a HoldCo restructure across two sets of lawyers and two sets of accountants who don’t regularly talk to each other. Someone has to understand what each one is working on, make sure the decisions on one side don’t create problems on the other, and keep the whole thing moving toward the same destination. That’s a real job. It takes real time.
For a founder whose time is worth what his time is worth, that’s a significant cost that never shows up on an invoice.
The family office model exists precisely because at a certain level of wealth, this coordination problem becomes obvious enough that someone builds a solution for it. You hire a CFO for your personal financial life — someone whose entire job is to make sure the pieces are talking to each other.
Most founders aren’t at the threshold where a traditional family office makes sense. But the problem is identical. The complexity is real. And the cost of being your own quarterback — in time, in missed opportunities, in decisions made in isolation — compounds quietly in the background whether you’re paying attention to it or not.
A question worth sitting with this week:
How much of your time last month went to coordinating the people who are supposed to be managing your financial life?
If the number is more than zero, it’s worth asking whether that’s the best use of what you’ve built.
— Trevor