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Dive into a collection of past posts and rediscover timeless content.
Why Do Treasury Bills Have a 0% Coupon?

Sep 28, 2026

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17 min read

Why Do Treasury Bills Have a 0% Coupon?

Treasury bills say “0% coupon,” yet investors can still earn a positive return. Here's the simple little pricing trick that makes it work, and why the number on the coupon can be so misleading.

Penny Brief
Penny Brief
Why Does Everything Feel Expensive If Americans Are Still Shopping?

Sep 28, 2026

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7 min read

Why Does Everything Feel Expensive If Americans Are Still Shopping?

The most interesting businesses right now aren't always the ones making headlines. From American Express and Fiserv to AI infrastructure and SpaceX, here's what today's business moves can teach us about finding companies with real staying power.

Penny Brief
Penny Brief
Why Own a Bond Fund When Cash Is Paying More?

Sep 27, 2026

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17 min read

Why Own a Bond Fund When Cash Is Paying More?

Cash is paying 3%+. Your bond fund just lost money. So why not dump the bonds? The answer gets interesting once you look beyond today's yield.

Penny Brief
Penny Brief
Target-Date Funds: Do You Really Need Anything Else?

Sep 27, 2026

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9 min read

Target-Date Funds: Do You Really Need Anything Else?

A 401(k), Roth IRA, HSA and brokerage account can look like four different portfolios. They aren't. Here's the surprisingly simple way to see what you actually own.

Penny Brief
Penny Brief
Why Two Teachers With the Same Salary Can Retire With Radically Different Amounts

Sep 27, 2026

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16 min read

Why Two Teachers With the Same Salary Can Retire With Radically Different Amounts

Two teachers can earn the same salary, work in the same school, and have the same pension. One can still retire with hundreds of thousands more. Here’s where the money goes.

Penny Brief
Penny Brief
Should Teachers Use a 403(b)? What Teachers Need to Know

Sep 27, 2026

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14 min read

Should Teachers Use a 403(b)? What Teachers Need to Know

Your school offers a 403(b). But should you actually use it? The answer depends on what's hiding inside the plan: fees, investments, tax options, annuities and a few teacher-specific rules most people never hear about.

Penny Brief
Penny Brief
Moving Abroad With $2 Million: U.S. Taxes, Exit Tax & Expatriation Rules

Sep 27, 2026

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23 min read

Moving Abroad With $2 Million: U.S. Taxes, Exit Tax & Expatriation Rules

Moving abroad with $2 million sounds simple. The tax reality is not. Here’s what changes when a wealthy American moves overseas, keeps U.S. stocks, opens foreign accounts, or gives up U.S. citizenship.

Penny Brief
Penny Brief
Can You Move Stablecoins Abroad Without Paying Tax?

Sep 27, 2026

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27 min read

Can You Move Stablecoins Abroad Without Paying Tax?

Stablecoins look like digital dollars, but the IRS generally treats them as property. Here's when moving USDC or USDT abroad is just a transfer, and when selling, swapping, spending or gifting it can trigger tax consequences.

Penny Brief
Penny Brief
Why Does Your Moving Date Matter for Taxes?

Sep 27, 2026

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23 min read

Why Does Your Moving Date Matter for Taxes?

Moving abroad isn't just about choosing the right country. The exact date you leave, become a tax resident, open accounts or sell investments can change which tax rules apply.

Penny Brief
Penny Brief
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