No Son of Mine Will Marry a Machine
Read time: 2½ minutes
Welcome to issue #044 of Unicorn Parents. Each week, I share practical insights and reflections to help you build a profitable business without missing the magic at home. If you’re serious about winning at work while raising great kids, you’ve come to the right place. This is a community built for ambitious parents who want both.
I was born in the early 80s.
Some call us Millennials.
Others call us the Oregon Trail generation.
I used to roll my eyes at generational labels. They felt arbitrary—lazy shortcuts for explaining human behavior.
Then recently, I watched how someone born in the late 90s approaches dating and relationships.
And I realized:
I don’t just not understand their logic.
I actively resist accepting it.
Dating purely for personal joy.
Radical “honesty” that leaves emotional wreckage behind.
Flirting freely—even simultaneously—because transparency absolves responsibility.
No shame. No obligation. No friction.
My instinctive reaction wasn’t curiosity.
It was rejection.
And that scared me.
Because suddenly, I could hear my parents’ voices echoing back at me.
“You can’t marry her. She’s not Korean.”
Fast-forward twenty years.
One day, my child might look at me and say:
“Dad, I want to marry my AI girlfriend.”
And I already know my gut response:
“No son of mine is going to marry a machine.”
But then comes the uncomfortable question:
How is that fundamentally different?
Every generation believes the next has lost the plot.
Every generation believes this time the line is being crossed.
And every generation is convinced their objections are rational, moral, and necessary.
Understanding vs. Respect
Here’s where things get tricky, especially for founders and parents.
I make big decisions weekly about founders I back.
Often, I don’t fully understand why they’re choosing the path they’re choosing.
But if I decide to support them, I don’t half-commit.
I don’t say:
“I’ll back you, as long as you make decisions that make sense to me.”
That’s not support.
That’s control.
And yet, how often do we do exactly that with our kids?
We expect autonomy for ourselves.
Grace for our mistakes.
Respect for our convictions.
But when our children make choices that don’t align with our logic, suddenly respect becomes conditional.
Education as Anxiety, Disguised as Love
As you know, I’m deeply involved in education.
Thousands of students apply to our programs every year.
I watch parents enroll six-year-olds into coding academies.
Stack résumés before personalities form.
Treat childhood like a pre-interview.
Why all this effort?
Harvard? Stanford?
Prestige? Security? Proof?
At some point, we have to ask:
Are we nurturing children—or manufacturing outcomes?
What gets compressed early often unwinds later.
Distorted childhoods don’t disappear.
They resurface (usually in adulthood) through burnout, identity confusion, or an inability to make independent judgments.
What Parents (and Entrepreneurs) Actually Owe
We don’t need to understand every decision our children make.
But we do need to do three harder things:
Enjoy our children for who they already are
Not who they might become if everything goes perfectly.Respect their decisions—even when they violate our internal logic
Respect doesn’t require agreement. It requires restraint.Prepare them for judgment, not outcomes
The world they inherit will not reward obedience.
It will reward discernment.
As parents—and as entrepreneurs—we can’t outsource this responsibility to systems that were never designed for human flourishing.
Education systems optimize for sorting.
Markets optimize for efficiency.
Algorithms optimize for engagement.
None of them optimize for wisdom.
That part is still on us.
Maybe the real task of parenting isn’t preventing our kids from making choices we don’t understand.
Maybe it’s ensuring that when they do,
they’re grounded enough to live with the consequences
and loved enough to come home if they need to.