Physical Address
304 North Cardinal St.
Dorchester Center, MA 02124
Every now and then, a simple errand turns into an unexpected debate.
For me, it happened at the entrance of a grocery store.
You know the scene. You grab a cart, mentally preparing for rising food prices and a checkout total that somehow always exceeds your budget. But before you even make it past the automatic doors, there’s a folding table blocking your path. Someone’s selling cookies. Someone else is asking for donations. And recently, someone was asking for signatures.
On this particular day, I stopped.
The person at the table was collecting signatures for multiple causes—funding initiatives, social programs, policy reforms. I stood there longer than I intended to, flipping through pages and signing where I felt comfortable. Twenty-plus pages later, one topic caught my attention.
Taxing the rich. The so-called “1%.”
Now, I work in accounting and finance. Numbers aren’t just theoretical for me; they’re practical. They tell stories about incentives, structures, behavior, and unintended consequences. So when I saw the petition advocating higher taxes on the wealthy as a solution to economic inequality, I couldn’t help but engage.
I shared a few thoughts with the person at the table.
Not because I’m against fairness.
Not because I think inequality doesn’t matter.
But because I don’t believe taxing the rich is going to work the way people think it will.
Let me explain why.
1. The Wealthy Don’t Play by the Same Tax Rules You Do
One of the biggest misconceptions in the “tax the rich” conversation is that wealthy individuals earn income the same way most people do.
They don’t.
Most middle-class families rely on W-2 income. A salary. Maybe a bonus. Taxes are withheld automatically. There’s very little flexibility.
The wealthy, on the other hand, structure their income differently. They own businesses. They own equity. They own appreciating assets. Their money doesn’t come primarily from a paycheck—it comes from investments.
And that changes everything.
People with significant wealth hire top-tier accountants and tax attorneys. They don’t guess. They don’t use generic software. They use professionals who understand the tax code inside and out.
If tax rates go up, they don’t just shrug and pay more.
They restructure.
They defer income.
They move assets.
They change entity types.
They shift jurisdictions.
They use trusts.
The tax code is complex for a reason. And complexity favors those who can afford to navigate it strategically.
So when people say, “Just raise their taxes,” I often wonder—on what base? On which definition of income? And how long before that income legally shifts into a different category?
2. Tax Laws Are Written Within a System That Protects Capital
This may be uncomfortable to say, but tax systems are not neutral. They’re designed within political and economic structures that heavily involve capital holders.
Look at how different types of income are taxed:
- Earned income (salary)
- Capital gains
- Dividends
- Business income
- Real estate depreciation
The average worker earns a salary. That income is taxed at ordinary income rates.
But long-term capital gains? Often taxed at lower rates.
Qualified dividends? Lower rates.
Real estate? Depreciation shields taxable income.
The structure itself favors asset ownership over labor.
And that’s not accidental. Policymakers often argue that favorable treatment of investment income encourages economic growth. Whether you agree or disagree, the reality is that these provisions exist and have existed for decades.
When new tax legislation is introduced, it often includes carve-outs, exceptions, phase-ins, and technical definitions that leave room for strategic planning.
In other words, the system evolves—but it rarely closes every door.
3. The Wealthy Use Debt as a Wealth-Building Tool
Here’s something most people don’t realize: wealthy individuals often live off debt.
That sounds counterintuitive at first. But it’s a powerful strategy.
Let’s say someone owns millions in stock or real estate. Instead of selling those assets (which would trigger capital gains tax), they borrow against them.
Loans are not income.
Loans are not taxed.
If you have appreciating assets, you can use them as collateral. You access liquidity without creating a taxable event.
Meanwhile, the asset continues to grow.
This strategy—borrow, don’t sell—allows wealth to compound while minimizing taxes. It’s perfectly legal. It’s structured. It’s strategic.
So again, if the argument is that raising taxes on income will significantly impact the wealthy, you have to ask: how much of their lifestyle is actually funded by taxable income?
4. Most Wealth Isn’t Salary-Based
When people imagine “the rich,” they often picture someone earning a massive annual salary.
But the reality is that true wealth is built through ownership.
Ownership of:
- Businesses
- Stocks
- Real estate
- Private equity
- Intellectual property
These assets generate income in ways that are taxed differently—or sometimes deferred entirely.
If your wealth is tied up in assets that appreciate over time, you don’t necessarily need to realize income annually. You can let it grow. You can structure distributions strategically. You can time sales around favorable conditions.
Contrast that with the average worker who exchanges time for money and receives a paycheck every two weeks.
Raising income tax rates primarily affects earned income. But once you move into the world of asset-based wealth, the rules change.
5. Behavior Changes When Incentives Change
Tax policy doesn’t exist in a vacuum. It influences behavior.
If rates rise significantly, capital doesn’t just sit still. It moves. Businesses relocate. Investment strategies adjust. Compensation structures change.
We’ve seen this globally. High-tax environments sometimes lead to capital flight, residency changes, or shifts in corporate domicile.
That doesn’t mean taxes shouldn’t exist. It means there’s a practical limit to what taxation alone can accomplish without broader structural reform.
You can’t simply pass a law and expect behavior to remain static.
6. Petitions Feel Empowering—But Education Is More Powerful
Standing outside that grocery store, signing page after page, I realized something.
We’re quick to demand policy changes.
We’re slower to demand financial education.
Instead of asking, “How do we tax them more?” maybe more people should be asking, “How do I learn what they know?”
Why isn’t personal finance a mandatory subject in school?
Why do students graduate understanding trigonometry but not compound interest?
Why do most people learn about investing, taxes, and credit the hard way?
I didn’t truly understand personal finance until I was 27.
Twenty-seven.
That’s years of missed opportunity. Years of not fully understanding how money works, how assets compound, how tax strategy influences outcomes.
No one sat me down in high school and explained:
- The difference between earned income and passive income.
- How to read a tax return.
- What depreciation is.
- How to legally reduce taxable income.
- How to build credit strategically.
- How to think like an owner instead of an employee.
I had to learn it myself.
And that changed everything.
7. The Real Advantage Is Knowledge
If you truly want to close the wealth gap, education is a more sustainable solution than taxation alone.
Teach people:
- How to invest early.
- How to start and structure businesses.
- How to use tax-advantaged accounts.
- How to understand debt.
- How to read financial statements.
- How to think long-term.
The tax code is public information. The strategies aren’t secret. They’re just not widely taught.
Instead of standing outside grocery stores asking for signatures, imagine if we had tables teaching:
- How capital gains work.
- How to legally reduce your tax burden.
- How to buy your first rental property.
- How to build assets that generate income.
That’s empowerment.
8. Financial Literacy Changes Generations
One of the strongest thoughts I had after that grocery store interaction wasn’t about policy—it was about my son.
I will teach him what I had to learn late.
He will understand:
- Assets vs. liabilities.
- Cash flow.
- Tax brackets.
- Investment vehicles.
- Business structures.
Not because I want him to avoid contributing to society. But because I want him to understand the system he operates within.
The earlier you understand money, the more time works in your favor.
Compounding isn’t just about dollars—it’s about knowledge.
9. Taxing the Rich Is an Emotional Argument—But Wealth Is Structural
The frustration behind “tax the rich” is understandable. People see inequality. They see rising costs. They see corporate profits and stagnant wages.
But frustration doesn’t automatically equal effective policy.
Wealth isn’t primarily built through high salaries—it’s built through ownership, leverage, and strategic tax planning.
If you don’t understand those mechanisms, you’ll always feel like the system is unfair. And maybe parts of it are.
But reacting to that by demanding higher rates without understanding the structural design misses the deeper issue.
The rules of wealth-building are different from the rules of wage-earning.
And until more people understand that distinction, raising taxes won’t create the outcome many expect.
10. Learn the Loopholes Instead of Complaining About Them
Here’s the part that might be controversial.
Instead of focusing solely on closing loopholes, learn them.
Legally.
Understand:
- Retirement account advantages.
- Depreciation strategies.
- Entity structuring.
- Capital gains timing.
- Opportunity zones.
- Tax credits.
This isn’t about cheating the system. It’s about understanding it.
The wealthy don’t succeed because they hide money in mattresses. They succeed because they understand the language of money and law.
That language is learnable.
Final Thoughts
As I walked away from that grocery store, groceries in hand, I kept thinking about the disconnect.
We want fairness.
We want opportunity.
We want progress.
But policy alone won’t level the field.
Financial literacy might.
I’m not arguing that taxation has no role. Governments need revenue. Infrastructure, schools, defense, and public services require funding.
But believing that simply raising taxes on the top 1% will fundamentally change economic outcomes ignores how wealth is structured and protected.
The real shift happens when more people:
- Think like owners.
- Invest like owners.
- Understand taxes like owners.
I didn’t learn that until 27.
My son won’t have to wait that long.
And maybe that’s where change truly begins—not at a folding table outside a grocery store, but at a kitchen table teaching the next generation how money actually works.
