Most people believe the wealthy have access to some secret playbook. Something hidden. Something exclusive.
But the truth is far less glamorous and far more practical.
The wealthiest families don’t win because they hustle harder, take bigger risks, or invent the next unicorn.
They win because they understand something most people never learn:
Prosperity is philosophical before it’s tactical.
It’s generational before it’s transactional.
If you want prosperity, you must first understand the philosophy of building and stewarding wealth before applying ‘tactics’ for earning more dollars.
“Generational before it’s transactional” means you have to teach your kids (and their kids) this stewardship and philosophy before you teach them how to make money.
And here’s the hard truth: if you fail to grow up emotionally, you’ll never grow up financially.
That’s not theory.
It’s my direct life experience.
Just this week, I was driving with my son, and out of nowhere he asked, “Dad… are you proud of me?”
I told him:
“You have one of the biggest hearts I’ve ever seen. I love who you are. Now I just want you to find and focus on what fulfills you, know what you want, to live your purpose.”
See…
Old money talks about purpose. New money talks about purchases.
Old money builds identity. New money buys identity.
If you want to become wealthy, you must first behave like the wealthy.
Even if you don’t have wealth yet, this is where the game truly begins.
What follows are 10 principles I’ve learned from working with billionaires, losing everything in my 20s, rebuilding, and now helping entrepreneurs create lasting wealth.
Some will challenge what you’ve been taught. Others will feel uncomfortably boring.
But if you apply them, you won’t just make money. You’ll keep it, grow it, and pass it on.
Let’s go.
1. Wealthy Families Don’t Rely on Wages, They Rely on Purpose and Assets
Wages are taxed. Heavily.
Assets aren’t… at least not in the same way.
New money tries to earn more.
Old money tries to own more.
That’s a tax lesson, but it’s also a life lesson.
Because once you stop trying to prove yourself with income, you can start building wealth with intention.
When my son opened up to me about being bullied years ago by kids from an ultra-wealthy family, it was heart wrenching.
He didn’t even tell us until he came home from school one day having been pushed so far we could see him shaking.
I remember thinking:
“All this money, but they never taught their kids how to treat another human being.”
My son now quietly helps kids online who are dealing with bullying because he turned pain into purpose.
That’s real wealth.
And it’s something no amount of money will ever teach you.
Old money done wrong breeds entitlement or worse. If you’ve seen shows like Succession, it shows the worst of the worst.
Old money done right breeds stewardship. They don’t make as many movies or shows about the good, because it isn’t as dramatic. It can be kinda boring. Old money can be that way. Stay the course, have patience, focus on what you know, and live well (but privately.)
2. Inflation Punishes Savers and Rewards Owners. But Only If You Avoid the New Money Trap
Inflation makes savers poor and owners wealthy.
But here’s the nuance no one talks about:
New money thinks ownership means complexity.
Old money knows ownership means simplicity.
In my 20s, I owned over 100 real estate properties, two oil and gas deals, invested in two IPOs, started a hard-money lending fund, a mortgage company, a P&C insurance agency all because I thought saying “yes” to everything was the path to wealth.
It wasn’t.
And in my book Money Unmasked, I share more about this exact trap.
See, Old Money is about focus. It is about what you understand, what you do well, and what works more than speculation.
Go deeper. Not wider.
Wealth isn’t built by stacking distractions.
Wealth is built by stacking boring, predictable wins.
Like the family office that owns Maverik gas stations.
Their growth strategy is having really nice bathrooms. Bigger ceilings. Better lighting.
More convenience.
Not sexy… at all.
But wildly profitable.
New money gets bored and looks for the next “hot” thing.
Old money just gets plain wealthy, and stays that way.
3. Wealthy Families Use Infrastructure as Their Engine (Not Hustle)
When my mentor met Phil Romano (creator of Fuddruckers and Romano’s Macaroni Grill), he told him the difference between millionaires and billionaires:
“I will never start a company without the right operator. You hustle. I build teams.”
New money says, “I’ll do it myself.”
Old money says, “Who has already mastered this?”
Phil told my mentor:
“You’re a multimillionaire because you work your ass off. I’m a billionaire because I find people who work their ass off.”
That’s the difference.
And it’s why, despite all my early success, I found myself in a 45,000-square-foot office that won architectural awards and drained cash.
A beautiful monument to ego and insecurity.
That’s new money.
Old money would have said:
Scale what works. Ignore the rest.
4. Old Money Protects Before It Grows
When I was asked to speak to 20 billionaires a few years ago, I had the opportunity to attend the entire time and saw something fascinating:
Even though they had plenty of money, they were still raising capital.
They all had their area of expertise that made them most of their money.
They kept the money due to their focus on risk management.
As I reveal in What Would the Rockefellers Do?, protection always comes before growth.
They focus on saving tax and managing risk.
One tax strategist I work with manages risk for nearly every billionaire in Canada.
Half our calls are literally: “How do we protect this? Shield that? Structure this entity? Limit that exposure?”
It’s boring.
It’s meticulous.
It’s foundational.
Which is why it works.
5. Old Money Builds Identity and Boundaries. New Money Seeks Validation.
Old money has boundaries.
New money wants to be liked.
New money lends money to friends who never pay them back.
Old money says, “I don’t lend money.”
New money buys status symbols.
Old money buys stewardship.
New money flexes.
Old money focuses.
I lived the new money way in my 20s.
I bought a black-on-black Bentley.
I did a photoshoot on the Salt Flats with it.
I made the cover of a magazine.
And you know how many clients it got me?
Zero.
But you know what it did get me?
A moment where I yelled at my wife because she spilled a soda in the car.
She looked at me and said, “Is this who you are now?”
Ouch. Yep I had become “that guy”. I cringe now whenever I think about it, but it was an important lesson to learn. If you want the full story, check out my new YouTube video on this: “I Let Money Warp Me. Here are the Warning Signs (Be a Millionaire and stay YOU)”
6. Old Money Doesn’t Ascend by Accident
Old money succeeds because it’s intentional.
They build:
- Family constitutions
- Investment policies
- Clear boundaries
- Succession rules
- Roles, responsibilities, and rituals
- Space for money conversations
If a wealthy family has four generations still intact, I promise you it wasn’t luck.
They practiced stewardship by design.
When I help clients build their Family Constitution, you can watch their whole energy shift.
It’s the moment wealth becomes identity instead of anxiety.
New money plays to win.
Old money plays to last.
7. Wealthy Families Operate From High Purpose, Low Need
When you have high need, you operate from low power.
Most entrepreneurs live in high-need mode.
They need the client. They need the deal. They need the partnership. They need the validation.
Old money operates from purpose.
They only say yes when it’s aligned.
This is what happens when you reach economic independence. The moment you’re no longer living on your P&L, but on your balance sheet. When there is enough cash flow from assets to cover your expenses.
What assets do you have that create cash flow? This is about assets that do the work when you aren’t working.
It’s not about the net worth.
It’s about the clarity. The cash flow.
Once you’re financially independent, you can swing for the fences in your vision. You have more choice. More freedom.
8. The Wealthy Follow the Same Formula But They Don’t Rush It
MAKE.
KEEP.
GROW.
MULTIPLY.
Poor people focus mostly on “make.”
Middle class emphasized cutting back to “keep.”
New money focuses on speculation to “grow.”
But wealthy families know it’s sequential.
Make → Keep → Grow →Multiply.
You can’t skip a step.
Invest in yourself to make more money. Increase your financial IQ so you can keep more of what you make without cutting back (saving on tax, interest, and inefficiency). Then discover your Investor DNA to become a better investor and grow your money. When you have all three working in your favor, you multiply results. You become the consummate value creator.
When I made millions in my 20s but skipped “keep,” I lost everything.
When I started investing in everything except my own expertise, I multiplied losses, not wealth.
9. Wealthy Families Are Boring on Purpose
This is hard to hear, but here’s the truth:
Wealth is boring.
Rich looks exciting.
A wealthy family will buy:
- Land
- Cash-flow properties
- Utility companies
- Waste management businesses
- Boring insurance portfolios
- Private equity with proven operators
New money will buy:
- Lamborghinis
- NFTs
- NFTs of Lamborghinis
- AI startups
- Exotic deals
- Private capital schemes
- The coolest-sounding investment at the party
Wealthy families accumulate assets you never see.
New money purchases symbols you never stop noticing.
One is sustainable. The other is exhausting.
10. Wealth Isn’t a Number. It’s an Identity
True wealth isn’t measured in dollars.
It’s measured in:
- How grounded you are
- How aligned you are
- How present you are
- How clear you are
- How purposeful you are
- How protected you are
- How well your family communicates
- How much you know who you really are
The world is full of rich people who are miserable (rich in stuff, but poor in cash flow).
And full of wealthy families who you might walk by on the street without knowing it.
The difference isn’t money.
It’s mindset, philosophy, clarity, boundaries, structure, and purpose.
When you tap into that, you won’t just build wealth.
You’ll keep it.
Grow it.
Enjoy it.
And pass it on.
That’s the game.
And now it’s yours.
Want to Accelerate Your Journey to True Wealth?
Our last Masterclass was a hit. We got amazing feedback. I had a blast sharing my message with passion. And we even built a fun, collaborative community with VIP members in a private WhatsApp group.
Tickets are on sale now for just $97 and we’re going to help you go from money chaos to financial clarity.
Thanks for reading, and hope to see you there.
