EP322: 7 Ways to Raise Kids Who Aren’t Spoiled, Entitled, or Expect the World to Owe Them

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Let’s have some real talk today.

As entrepreneurs, investors, and builders of big dreams, many of us are out here building incredible legacies — and yes, that often includes wealth.

But here’s what we’ve seen, time and time again (and maybe you have too):

You can build the fortune…

You can build the life…

But if you’re not intentional about it, your kids can still grow up thinking life is owed to them. 😦😦

That is not the legacy you want to leave.

This episode isn’t about how we’ve built a $400 million portfolio (though that’s part of my story).

And it’s not about making money — because most of us reading this? Money isn’t the problem.

The real issue is this:

How do you make sure your kids don’t grow up soft, spoiled, and ungrateful?

We want to share seven things that will help you do just that — and help protect your legacy, your wealth, and most importantly… your kids’ future.

NO. 1 Stop Protecting Them From Discomfort

Let us tell you something: entitlement is taught, not born.

Every time your child feels frustrated and you rescue them instead of letting them navigate the hard feelings? You’re unintentionally teaching them that frustration should be avoided and comfort should be guaranteed.

We learned this first-hand growing up.

Our family went through seasons of wealth and seasons of struggle — and honestly, it was the struggles that taught me resilience.

Without them, we might have believed comfort was normal and setbacks were personal.

Want to raise resilient kids?

Let them feel disappointment.

Let them navigate frustration.

Resist the urge to swoop in every time life gets a little bumpy.

NO. 2 Stop Giving Without Teaching

It’s easy to think that giving our kids “everything we didn’t have” is love.

But when giving lacks teaching, it backfires.

We know parents who include their kids in everything — business strategy meetings, conferences, masterminds.

You better believe those kids aren’t asking for handouts. They’re pitching business ideas and learning how money works.

If your kids only know how to spend money, they’ll never know how to steward it.

Don’t just give them things.

➡️ Give them context.

➡️ Give them conversations.

➡️ Give them responsibilities.

NO. 3 Stop Hiding the Struggle

If your kids don’t know what it took to build what you’ve built, they won’t know what it takes to sustain it.

So many well-meaning parents try to shield their kids from the messy parts — the business setbacks, the layoffs, the hard choices.

But here’s the truth: when kids only see the highlight reel, they assume life is always like that.

And then when life hands them a curveball? They crumble.

Tell your kids the full story.

Let them see that success is never guaranteed.

Help them understand that every dollar has a backstory.

NO. 4 Stop Thinking Legacy Is Just Legal

We’re going to say something that might sting: an airtight estate plan is not the same as a legacy.

You don’t pass on values through a trust.

You pass them on through conversation, modeling, and presence.

Have you written down the values you want to pass on?

Do your kids know the story behind your business and your family’s wealth?

If not — start there. A well-fed bank account with no soul behind it is a recipe for disaster.

NO. 5 Stop Treating Philanthropy Like a Tax Strategy

Real giving is felt, not just funded.

If you want your kids to grow up grounded and grateful, philanthropy can’t just be something that happens in your CPA’s office.

Bring your kids with you to serve.

Let them see — and experience — lives that are different from theirs.

When kids see need up close, it changes how they view their own abundance.

It shifts wealth from a mirror of their identity… to a tool for doing good in the world.

NO. 6 Stop Avoiding Money Talks

One of the biggest mistakes we see wealthy parents make is refusing to talk openly about money.

They think, “If they don’t know how much we have, they won’t get spoiled.”

Nope.

Silence breeds misunderstanding.

If you’re not having money conversations, your kids will fill in the gaps — often with fear, shame, or entitlement.

Instead, invite them into age-appropriate discussions. Let them listen to investor calls. Show them what it looks like to steward wealth with wisdom.

Money doesn’t corrupt kids.

Silence does.

NO. 7 Stop Believing You Have Time

This one hits close to home.

We always think we’ll do the family values talk next summer.

We’ll bring them into the business after the next deal closes.

We’ll teach them financial literacy when they’re older.

But here’s the hard truth: your kids are learning now — with or without you.

Every day they’re absorbing lessons about money, power, and worth… often from TikTok, YouTube, or their peers.

You don’t need to have the perfect words.

You just need to start. Today.

Final Thoughts

We’ll leave you with this:

We recently heard about an ultra-wealthy family who had to hire a six-figure specialist to “fix” their grown kids’ entitlement issues. By then? It was too late.

The key isn’t fixing later — it’s training earlier.

Start now.

Even if you’re still figuring it out yourself.

Even if it feels imperfect.

Because the most powerful part of your legacy won’t be the dollars in your trust…

It will be the values in your kids’ hearts.

You’ve built the wealth. Now build the wisdom.

And if you want to know how we built millions by starting before we were ready?  Then, we’ll see you in the next video. 🎥