When Winning Isn’t Winning
Read time: 3 minutes
Welcome to issue #050 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.
“Lion vs Tiger…who wins?”
That was the question at our dinner table last night.
My sons are barely five.
And somehow it escalated into:
“I’m the winner!”
“No, I’M the winner!”
What is it with our obsession with comparing?
I never taught them that.
If anything, my wife and I are super-intentional.
We’re careful about what they eat.
What they watch
What they’re exposed to.
(My wife didn’t let them watch Disney movies until recently. Yes, borderline heresy.)
I’m more in the “let them explore anything as long as they’re not in danger” camp.
We don’t preach competition.
Yet somehow…
They are wildly competitive.
Where did that come from?
Godzilla vs King Kong.
Freddy vs Jason.
Alien vs Predator.
Humanity loves a showdown.
But we don’t just love battles.
We love winning.
And apparently, so do toddlers.
When they win, their whole body lights up.
Chest out.
Voice louder.
Smile wider.
Winning feels like validation.
Some uncomfortable questions:
Is conditioning useless?
Are our kids just executing whatever was coded into their DNA?
Is all this careful parenting just… cosmetic?
Not quite.
But here’s what I’m realizing:
Nature loads the instinct.
Nurture directs it.
The desire to compete?
That’s probably wired in.
Evolution favored those who survived, built, hunted, protected, and outperformed.
Comparison is ancient.
But what do we do with that instinct? That’s parenting.
But this isn’t just about toddlers.
It’s about founders.
What does “winning” mean in startups?"
Getting funded?
Not really.
I’ve seen founders raise big rounds…
… and quietly lose control of their companies.
Does winning mean hitting revenue goals?
Again, not really.
I’ve seen eight-figure businesses implode because the founders were exhausted, resentful, or morally compromised.
Valuation?
Press?
Exit?
External wins are loud.
But they’re fragile.
Real winning might look like:
• Building something you’re proud of
• Keeping your integrity when pressure mounts
• Paying your team on time
• Going home able to look your spouse in the eye
• Not becoming someone you despise in the process
They don’t trend on LinkedIn.
But they compound.
Our kids shout, “I’m the winner!” because winning feels like identity.
Founders aren’t that different.
“We closed the round.”
“We’re beating our competitors.”
“We hit our target.”
The ecosystem trains us to define winning narrowly.
Money raised.
Growth rate.
Public applause.
But nurture (i.e., intentional formation) asks a better question:
“What kind of winner are you becoming?”
Because some win the round, only to lose their soul.
Some win in the market and lose their marriage.
Some win the valuation and lose their health.
So no, conditioning isn’t useless.
It’s decisive.
The goal isn’t to eliminate competition.
It’s to expand the definition of winning.
For our kids.
And for ourselves.
Competition, shaped poorly, becomes:
• insecurity
• comparison spirals
• zero-sum thinking
Shaped wisely, it becomes:
• resilience
• excellence
• internal standards
• long-game thinking
If my boys grow up obsessed with beating others, I failed.
If they grow up obsessed with becoming better than yesterday (more disciplined, more generous, more grounded), we’re on the right track.
Same for founders.
The best founders I know?
They’re competitive.
But not desperate.
They don’t need others to lose in order to feel like they’re winning.
They play long games.
And long games require a different definition of victory.
Nature may give our kids fire.
But nurture decides what that fire fuels.
We’re not raising kids to win trophies.
We’re raising them to win at life.
When our employees can be successful and thrive without us, then we know we have created a successful business. The same could be said about raising our children. Its bitter sweet, but its good.