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November 14, 2025

50 Year Mortgages: The Worst Financial Idea Ever?

More debt, more interest, less wealth. Let’s break down the math.

November 12, 2025

How dividend stocks can (and can’t) build your financial freedom.

Dividends feel rewarding. but for high-income earners, they can quietly drag down long-term returns.

November 11, 2025

Real estate feels different right now

The flashy stuff is slowing down. The fundamentals are starting to shine again.

November 10, 2025

Should you invest or pay off debt first?

Here’s how I weigh the math, emotion, and behavior behind the decision.

November 9, 2025

Sorta Random Sunday: Remembering Nick Mangold and the Meaning of Sports

Nick Mangold’s life and legacy are a reminder of why sports matter far beyond the scoreboard.

November 7, 2025

Why I Don’t Panic When the Market “Drops”

Most of what we fear as investors are “shallow risks.” Here’s why they don’t matter.

November 5, 2025

Our 2025 passive income just hit $398,000. Here’s how.

5 years ago, I couldn't imagine that our leveraged income covers 100% of our expenses.

November 3, 2025

Stop Leaving a “Tip” for the IRS in Retirement

Roth conversions help you decide when you pay taxes to keep more of what you earn.

November 2, 2025

Sorta Random Sunday: Why Jump Through all the Hoops?

What do all the “hoops” to jump through in life actually measure?

October 31, 2025

When Will I Truly Reach FIRE?

After 5 years on the path, I ran the numbers…

October 30, 2025

The Case for GSI Disability Insurance, Even if you’re Perfectly Healthy

GSI isn’t a backup plan. It’s often the best first choice for residents and fellows.

October 29, 2025

The P/E Ratio: Financial Signal or Just Noise?

Here’s how to interpret one of Wall Street’s favorite numbers, without letting it derail your investing plan.