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Highland Private Office

The 18-Year Investment Horizon

Why we build wealth differently for parents

Evan Ross
Evan Ross
@evanrossfl
Evan Ross  -  Investing

The math changes when you have kids.

Most financial advice assumes you will work until 65, then retire. But if you have a 5-year-old, your real timeline is not “until retirement.” It is “until they don’t need you anymore.”

That is roughly 13 years of influence left. Maybe 18 if you are lucky.

Why standard financial advice doesn't work for parents

Most wealth strategies optimize for a 40-year timeline. You have 15. They assume linear income growth, but kids create step-function costs - daycare, school, activities, college - that hit in waves, not gradually. And they treat wealth as an endpoint instead of what it actually is for a parent: a tool to buy time.

What we do differently at Highland

1 Compressed Timelines

We build for liquidity events in 5–10 years, not 30. Because you need optionality while your kids are young, not when they are grown.

2 Business Acquisition as Leverage

Buying cash-flowing businesses lets you own your time before traditional retirement age. One $500K net business replaces a W-2 income and buys you mornings with your kids.

3 Presence > Portfolio

We optimize for what we call “high-presence returns” - investments that create time and mental bandwidth, not just compound interest.

Because the best thing you can give your kids is not a bigger inheritance.

It is a parent who is actually there.


Where I work

I advise founders through Highland Private Office and help businesses implement AI through Naveron.

Highland Private Office → Naveron AI →