What I actually do with my three daughters
I am in this one myself, so I am not writing it as an advisor who read a study.
I started this business at 26 as my twelfth startup and the first one that worked. Nineteen years later I have three daughters and I am in the middle of the same thing you are. My father raised $1 billion for non-profits before I ever started, so I grew up watching it from the other side too.
Here is what I got wrong for years. I thought grooming the next generation meant teaching them the business. It does not. It means teaching them judgment, and the business is just the place they practice it.
The four things I actually do
1. I bring them into rooms full of adults who are not me.
I bring my daughters to our events. I am bringing my 12 year old to the Super Summit in December.
"Bringing my daughters to the events, having them hear from 100 speakers on stage at the Super Summit, they see that some are very well spoken. Some are obviously like a genius in their niche, but maybe not used to public speaking. Some are women who meet with them and get a cup of coffee, and they're laughing the whole time, having fun while meeting. And they don't have to see it just as strictly like they think of accounting."
That last line is the entire point and it took me years to understand it.
A kid whose only model of business is their parent has exactly one model. They think business is whatever their mom or dad is like, and if that does not match who they are, they conclude business is not for them. Twenty models in one day breaks that. Some are polished, some are awkward geniuses, some are laughing over coffee. The kid stops asking "am I like my dad" and starts asking "which of these am I."
It costs nothing. Bring them.
2. We study at breakfast.
"We study a physics textbook at breakfast, and I have them study a summary of two books. Be Useful by Arnold, and one of the top five chapters is burn your plan B. Don't have a plan B, just go deep on your plan A."
Physics at breakfast is not about physics. It is about doing something difficult before the day starts, together, as a normal thing. The content is close to irrelevant and the habit is the whole asset.
3. They get a scoreboard before they get a title.
The fastest way to break a capable kid is to give them a title the company knows they did not earn. Everybody in the building figures it out inside a week, including the kid. Give them something with a number attached that they either hit or miss in public, and let them miss it a few times.
4. Money stops at a line, and they know where it is.
Education paid. Emergencies covered. Up to $150,000 to $200,000 toward a first house. After that, nothing.
That is my answer, not the answer. Yours will be different and it should be. What matters is not the number. What matters is that they know the number now, rather than discovering it at the reading of a will, which is the worst possible moment to learn anything about money.
What usually actually happens
Number 5 is the one nobody solves and it is the cheapest to fix. Your kid needs somewhere to be wrong that is not your conference room. That is most of why I bring mine.
