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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.

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.

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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

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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.

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Do You Have a Tax Strategy?

Apr 18, 2026

Do You Have a Tax Strategy?

The difference between compliance and tax planning

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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.

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Trump Accounts and Market Rebound

Apr 11, 2026

Trump Accounts and Market Rebound

Early Signs of Momentum in Planning & Portfolios

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Resilience in Uncertainty

Mar 12, 2026

Resilience in Uncertainty

Emergency Funds and The Oil & AI Shocks

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The Emergency Fund

Mar 7, 2026

The Emergency Fund

Why Cash is Your "Psychological Hedge"

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Creating a Roadmap to Financial Independence

Jan 27, 2026

Creating a Roadmap to Financial Independence

Why High-Income Professionals Need a Different Roadmap than Reddit Told You

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The Wealthy Aren't Frugal

Jan 20, 2026

The Wealthy Aren't Frugal

They're Something Else Entirely

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Your Employee Benefits Package Is Worth More Than You Think

Jan 13, 2026

Your Employee Benefits Package Is Worth More Than You Think

And You're Probably Leaving Half of It on the Table

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Can We Afford to Have Another Kid?

Jan 5, 2026

Can We Afford to Have Another Kid?

Why the Spreadsheet Can't Answer Your Hardest Question

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Should I contribute to the Roth 401(k) or the Traditional 401(k)?

Jul 23, 2025

Should I contribute to the Roth 401(k) or the Traditional 401(k)?

Traditional vs. Roth 401(k): Balancing today’s tax relief against tomorrow’s tax‐free withdrawals.

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Estate Planning: The Asset Transfer Hierarchy

Jul 9, 2025

Estate Planning: The Asset Transfer Hierarchy

The method of distributing assets after death follows a hierarchy

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Qualified Small Business Stock (QSBS)

Jul 1, 2025

Qualified Small Business Stock (QSBS)

A concise introduction on how to leverage QSBS

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Year-End Checklist: Top 20 Financial Moves Before December 31

Nov 27, 2024

Year-End Checklist: Top 20 Financial Moves Before December 31

Key deadlines for many personal finance and tax planning strategies

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Should you invest in low volatility equity ETFs?

Nov 26, 2024

Should you invest in low volatility equity ETFs?

There is a place for low volatility ETFs.

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What should I do with my next saved dollar? Where should I be saving?

Nov 19, 2024

What should I do with my next saved dollar? Where should I be saving?

Using a savings waterfall strategy helps you organize your money so you can focus on your top financial goals. It ensures you're using your resources wisely and building long-term financial stability.

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Child Care Tax Credit 101: What Every Parent Needs to Know for Tax Season

Oct 1, 2024

Child Care Tax Credit 101: What Every Parent Needs to Know for Tax Season

Explore the Child Care Tax Credit essentials for parents, including eligibility, claiming, and maximizing benefits.

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20 Investment Lessons From The First Half Of My Career

Sep 5, 2024

20 Investment Lessons From The First Half Of My Career

Insights and Strategies Gained From Two Decades in the Market

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Consumers: Are they finally cracking?

May 29, 2024

Consumers: Are they finally cracking?

Markets, Insights, and Innovation

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Is the Russell 2000 the best small-cap index?

Apr 27, 2024

Is the Russell 2000 the best small-cap index?

S&P 600 vs Russell 2000 Comparison

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Sticky Inflation Complicates Fed's Rate Cut Plans

Apr 17, 2024

Sticky Inflation Complicates Fed's Rate Cut Plans

Wall Street's interest rate predictions fell flat.

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Market & Economic Observations | Portfolio Changes | Operations Update

Nov 8, 2023

Market & Economic Observations | Portfolio Changes | Operations Update

2023 2nd Half Update

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Year-End Checkup

Oct 18, 2023

Year-End Checkup

Let's Review & Plan

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