Wealth Habits
Archive
Search
Subscribe
Wealth Habits
Search
Gabriel Kaplan

Financial Planner (CFP® & CPA) | Stock Compensation Nerd | Tax Optimization Aficionado | Portfolio Architect Specialist Dad x 2 + Husband | Made in Sweden | Shaped in Uruguay | Embraced by New York.

Roth IRA or 529: Which One Should Come First?

Sep 15, 2026

Roth IRA or 529: Which One Should Come First?

Parents fund the 529 first out of guilt and the Roth IRA second out of habit. That order is backwards, and your kids will thank you for it later.

Read more
arrow-right
Every September, Wall Street Braces for a Selloff That Rarely Comes

Sep 8, 2026

Every September, Wall Street Braces for a Selloff That Rarely Comes

The data says September is the worst month for the market

Read more
arrow-right
The HSA: The Best Retirement Account Nobody Uses Right

Sep 1, 2026

The HSA: The Best Retirement Account Nobody Uses Right

It functions as a retirement account wearing a disguise, and almost nobody plays it that way.

Read more
arrow-right
If You Die Without a Plan, the State Decides Who Gets Everything

Aug 25, 2026

If You Die Without a Plan, the State Decides Who Gets Everything

It decides who raises your kids, too, and the judge has never met them.

Read more
arrow-right
The 4% Rule Was Built for 1994, and Retirements Now Stretch Past 30 Years

Aug 18, 2026

The 4% Rule Was Built for 1994, and Retirements Now Stretch Past 30 Years

Bengen published this rule three decades ago, and even he doesn't use it anymore.

Read more
arrow-right
Rent vs. Buy: Why Your Mortgage Calculator Is Lying to You

Aug 11, 2026

Rent vs. Buy: Why Your Mortgage Calculator Is Lying to You

The monthly payment is the smallest number in this decision. Taxes, maintenance, and closing costs add up to $30,000 most people never see coming.

Read more
arrow-right
What a Trump Account Actually Does for Your Kid

Aug 4, 2026

What a Trump Account Actually Does for Your Kid

Free money for some, a real head start for almost everyone else.

Read more
arrow-right
When Does It Make Sense to Work With a Financial Advisor?

Jul 28, 2026

When Does It Make Sense to Work With a Financial Advisor?

The honest answer nobody in the industry will give you.

Read more
arrow-right
What Your 401(k) Balance Doesn't Tell You About Retirement

Jul 21, 2026

What Your 401(k) Balance Doesn't Tell You About Retirement

The number on your statement is not your retirement income.

Read more
arrow-right
Your Credit Score Is a Lie, and a Lever

Jul 14, 2026

Your Credit Score Is a Lie, and a Lever

The number that controls your financial life was designed by lenders, for lenders. Here's how to turn it against them.

Read more
arrow-right
The Two-Income Trap: Why Earning More Together Can Leave You Broker Than Before

Jul 7, 2026

The Two-Income Trap: Why Earning More Together Can Leave You Broker Than Before

Two incomes should feel like a safety net. For most couples, it becomes a tighter leash.

Read more
arrow-right
The Real Cost of Lifestyle Creep

Jun 23, 2026

The Real Cost of Lifestyle Creep

Why More Money Isn't Making You Wealthier

Read more
arrow-right
What Is Tax-Loss Harvesting & Are You Leaving Money On The Table

Jun 16, 2026

What Is Tax-Loss Harvesting & Are You Leaving Money On The Table

The IRS Built You a Lifeline. Most Investors Never Reach for it.

Read more
arrow-right
How to Talk to Your Kids About Money Without Raising Entitled Adults

Jun 9, 2026

How to Talk to Your Kids About Money Without Raising Entitled Adults

The Conversation Most Parents Avoid Is the One That Changes Everything

Read more
arrow-right
Should You Pay Off Your Mortgage Early or Invest the Difference?

Jun 2, 2026

Should You Pay Off Your Mortgage Early or Invest the Difference?

The Answer Nobody Wants to Hear Because It Depends on How Well You Sleep at Night

Read more
arrow-right
The Hidden Costs of Waiting to Invest

May 26, 2026

The Hidden Costs of Waiting to Invest

The most expensive decision most high earners make isn't a bad investment. It's the years they spent not making one.

Read more
arrow-right
What To Do With A Windfall: Bonus, Inheritance, or Stock Vesting

May 19, 2026

What To Do With A Windfall: Bonus, Inheritance, or Stock Vesting

Money that arrives all at once leaves just as fast, unless you've decided what it's for.

Read more
arrow-right
How Much Life Insurance Do You Actually Need?

May 12, 2026

How Much Life Insurance Do You Actually Need?

Most people guess, and the guess is usually wrong in one of two expensive directions.

Read more
arrow-right
What Is a Backdoor Roth IRA, and Should You Use One?

May 5, 2026

What Is a Backdoor Roth IRA, and Should You Use One?

The tax loophole the IRS never closed, and the people quietly walking through it every year.

Read more
arrow-right
What are the pros and cons of a 401k to IRA rollover?

Apr 28, 2026

What are the pros and cons of a 401k to IRA rollover?

While rolling over is usually right, here's four scenarios where it just isn't.

Read more
arrow-right
Charitable Giving Isn’t the Tax Strategy You Think It Is

Apr 27, 2026

Charitable Giving Isn’t the Tax Strategy You Think It Is

The tax benefit you think you’re getting usually isn’t there

Read more
arrow-right
Do I Save On Taxes By Giving To Charity?

Apr 21, 2026

Do I Save On Taxes By Giving To Charity?

Most donors assume the generous scenario. Most donors are wrong.

Read more
arrow-right
Do You Have A Tax Strategy?

Apr 14, 2026

Do You Have A Tax Strategy?

By the time you're sitting across from your CPA, the game is largely over.

Read more
arrow-right
Trump Accounts and Market Rebound

Apr 11, 2026

Trump Accounts and Market Rebound

Early Signs of Momentum in Planning & Portfolios

Read more
arrow-right
Resilience in Uncertainty

Mar 12, 2026

Resilience in Uncertainty

Emergency Funds and The Oil & AI Shocks

Read more
arrow-right
Load more

Quick Links

Subscribe
Archive
Tags

Subscription

Signup
Login

Socials