Tax-loss harvesting is a way that some people attempt to trim their tax bills

Learn about loopholes in the American tax code, which involve everything from cat food to death to heavy machinery.

Study up on capital gains basics

Common capital gains tax tips include making sure you have money set aside for your capital gains tax burden and considering making estimated payments throughout the year.

Long- and short-term capital gains have different tax implications

Short-term gains (assets held for one year or less) are taxed like regular income, at rates up to 37%. Meanwhile, long-term gains (assets held over a year) are capped at 20%, offering significant savings for high earners.

Most Americans take the standard tax deduction

A tax deductible is an expense that a taxpayer or business can subtract from adjusted gross income, reducing their taxable income and therefore reducing the amount of taxes owed. Governments often use tax deductibles as a way to reward people who do things that are considered beneficial to society, like charitable donations.

Watch a breakdown of tax breaks most Americans don't know about

Programs like healthcare savings accounts or flexible spending accounts are tax-free accounts that are designed to help lower healthcare costs. However, many Americans don't use them and don't understand how they work.

Calculate your capital gains tax bill

If mental math is not your forte, a handy tool can help you figure out what you owe at tax time. Find the purchase and sales price of an asset, your taxable income, your tax filing status, and the length of time you held said asset, and you'll get your total for Uncle Sam.

Learn how tax credits are applied to income taxes

Tax credits are directly subtracted from the amount of money taxpayers owe on their annual income. Unlike tax deductions, credits reduce the owed amount while deductions reduce how much income is taxable. There are different types of tax credits that are either fully or partially paid out.

Short-term capital gains are gains on sales made in less than a year

In 2024, a single filer making anywhere between $200,001 and $243,725 per year would pay a 15% tax on long-term capital gains. But when it comes to short-term capital gains, they’d be taxed at the same rate as their regular income, which, in their case, is 32%.

Some policymakers take issue with long-term capital gains being taxed at a preferential rate compared to income from paid work

The concept of taxing unrealized capital gains—when an asset’s value increases but has yet to be sold—has been increasingly debated. Other policymakers in recent years have supported lowering the highest long-term capital gains tax rate and are generally opposed to levying taxes on unrealized capital gains.

Financial rules that many FIRE followers live by include guidelines around tax efficiency and more

Many FIRE proponents follow specific financial rules, like the 4% rule, in order to achieve FIRE. They also take steps to create an efficient tax strategy and take advantage of compound interest.

Read why the information Americans have about our tax system might be misleading

For many, filing taxes can be complicated and overwhelming. Some argue that the tax system obscures certain aspects of the US tax code, making it difficult for taxpayers to accurately assess potential reforms.

Shorting is a high-risk and expensive investment strategy that hedge funds specialize in

Most investors buy stocks with the expectation that those stocks will be worth more tomorrow than they are today. Short selling, known as “shorting,” a stock is the opposite: The investor is betting the stock will drop in value.

Half of the richest people in the US are finding ways around death taxes

One of the main purposes of the federal estate tax is to crack down on generational wealth, so wealth isn't concentrated among a select few. However, the ultra-rich have found ways around paying these taxes. This ProPublica article investigates the practices used by half of the 100 richest people in the US to avoid death taxes.

How the wealthy are preparing for an estate tax clip

In 2017, the federal government passed a tax bill that raised the estate tax threshold for individuals and married couples. However, this exemption was temporary and is set to expire at the end of 2025. This Bloomberg Tax podcast episode explains what wealthy individuals are doing to protect their estates before the tax change. Listen here.

The IRS may look at your social media if you're being audited

While some people cheat on their taxes, others evade paying them altogether. This article details methods the Internal Revenue Service uses to catch these people in the act, such as scanning social media, computer data analysis, and whistleblowers.

ETFs and mutual funds are both taxed on capital gains and on dividends.

If the estate tax is repealed, more expensive alternatives might come in its place

The federal estate tax has been up for political debate for decades. Many want to get rid of it altogether. If repealed other tax options, like capital gains taxes, could have people paying more in taxes than before.

Americans spend an average of $200 on tax preparation services like TurboTax and H&R Block

In 2025, about half of Americans were able to file taxes directly with the IRS for free. It was the second year of the agency's new program, which cuts out intermediaries. Though tax preparation has been free for many Americans, critics say tax companies upsell customers.

Gifting money is one way to avoid death taxes

Gifting money while you're alive is one way people avoid estate and inheritance taxes. There is a yearly cap on how much you can give to a person before that money is taxed—but there isn't a cap on how many people you can give money to in a year.

Trusts offer ways to reduce the taxes beneficiaries pay on assets in one’s estate

People of different socioeconomic classes often decide to establish a trust to avoid certain taxes. When someone dies and leaves assets to beneficiaries in a will, those beneficiaries must pay specific taxes a trust's beneficiaries avoid. It all depends on the type of trust.

Alternative investments carry unique tax implications

The specifics depend on the type of alternative asset, as well as how long you hold it for, and your income.

How to put on a hedge

These days, hedging your portfolio isn’t just for hedge fund managers. An explainer from Robinhood delves into what a hedged position actually is, why traders put on hedges, and how you, too, can work to guard your holdings against a market downturn. The idea is to derive gains from your portfolio when markets are trending up, down, or sideways.

In 1931-32, JP Morgan Jr. paid no income taxes due to his company’s losses

This legally reduced his taxable income under existing laws. Similarly, the Rockefellers leveraged charitable foundations to minimize taxes, allowing them to preserve wealth while directing funds to their preferred causes.

Reinvested dividends are not a way to dodge paying capital gains taxes

When an investor holds stock in a company that pays a dividend—a portion of its profits directly returned to shareholders as monthly or quarterly payments—they can choose to hold that dividend in cash, spend it, or reinvest it into more shares of that company’s stock.

How to owe nothing on your federal tax return

Do you know you can avoid owing the IRS money come tax season by making changes to your W-4? For context, a W-4 is the form you fill out when you first start a new job. It tells your new company how much money to withhold from each paycheck for taxes. Find out how to avoid writing a check to the IRS each April in this article.

Asset location is the type of account an asset is placed in

Investors are likely familiar with “asset allocation,” creating an ideal mix of different asset types in an individual's portfolio. But asset location matters just as much for investors who are conscious of how much they owe in capital gains taxes.

Read about 'skiplagging,' a money-saving travel hack.

Warren Buffett paid a lower effective tax rate than his secretary

While wages and salaries are taxed progressively at rates up to 37%, long-term investments are taxed at lower rates: 0%, 15%, or 20%. For wealthy individuals like Buffett, whose income mainly comes from investments, this means paying a lower effective tax rate than someone earning a salary.

Why the rich don't pay taxes like you do

The system behind the US income tax isn't as straightforward as it looks. You earn money. Taxes get taken out. Case closed … right? Not exactly. In this episode of "1440 Explores," we break down how the US tax system actually works, from confusing deductions and misunderstood tax brackets to why the wealthiest Americans often end up paying a very different tax than everyone else.

Many hedge funds use short selling as an alternative investment strategy to offset risk

Hedge funds typically use a "long-short" investment strategy—where funds diversify by investing in a mix of long positions and short positions—to balance risk and maximize profits. Including short positions gives hedge funds some protection against downturns in the market, although the strategy can have uncapped losses for investors.

HSAs are triple-tax advantaged—offering tax-free contributions, investments, and withdrawals

One of the reasons HSAs are so popular is the plan's triple-tax advantage. All contributions to an HSA happen pretax, funds in the HSA can be invested in stocks, bonds, or exchange-traded funds, and withdrawals to cover medical expenses are tax-free.

Some wedding expenses might be tax-deductible, depending on the situation

For instance, donating your wedding flowers to a homeless shelter or other nonprofit organization may make them tax-deductible. Some other expenses that may be tax-deductible in specific instances include historical venues, wedding gowns, and more. Find out more about which wedding expenses could be tax-deductible via this article.

Some experts and investors think short selling—a strategy in which investors bet that a stock will drop in value—helps keep the market healthy.

HSAs are frequently criticized for exacerbating inequality in healthcare access

Health savings accounts offer large tax advantages, but require personal contributions. Some argue that the tax advantages benefit wealthy individuals more than anyone else and that HSAs don't do much to help people who can't afford to regularly contribute to one. As a result, HSAs only decrease costs for those who can comfortably invest in them, and health inequalities between high-income and low-income individuals are exacerbated.

Check out a list of 15 red flags that might result in an IRS audit

The Internal Revenue Service has audited less than 1% of all individual tax returns. If you're still worried about being audited, know that some people are more likely to be audited than others, such as people who make a lot of money and those who take large charitable deductions.

Read about a dating simulation game that helps prepare your income taxes

For the 2022 tax year, prank-playing creative studio MSCHF created a dating simulation game that helped taxpayers prepare their income taxes. In "Tax Heaven 3000," players interact with anime love interest Iris (it's like IRS), and run through a series of questions that complete their taxes. Iris also warns the player to stay away from tax-preparation companies like TurboTax.

Backdoor Roth IRAs are loopholes used to access the tax advantages of a Roth IRA for individuals who otherwise make too much money to qualify for one

Backdoor IRAs work by investing money into a traditional IRA, and then converting that traditional IRA to a Roth IRA.

What it's like to do your own taxes for the first time

Most Americans across the country have one thing in common: They hate doing their taxes. Many use an accountant or an online service like TurboTax to avoid doing taxes themselves. In this video, two journalists decide to do their taxes on their own for the first time.

The highest 2024 federal income tax bracket covered income upward of $731,201 for married couples filing jointly

To understand what you would owe on short-term capital gains and to visualize the favorability of long-term tax rates, you need to know how your traditional income is taxed at the federal level. A breakdown explores the different brackets for 2024, separated by filing status.

Bear raiding is a manipulative tactic to bring a stock price down—and part of why short selling can be controversial

Bear raids occur when short sellers use manipulative tactics—like spreading false rumors or coordinating trades—to artificially drive down a stock's price and profit from short positions. Although bear raids are an illegal form of market manipulation, they can spook investors, prompting large selloffs of shares and causing a company's value to plummet. As a result, investors may be hesitant to invest in the company in the future, creating a feedback loop of stock downturn.

Explore a guide to 529 college savings plans

Investors put after-tax dollars into these education-earmarked accounts, and like a 401(k) or IRA, they invest them into stocks, bonds, or funds. When it comes time to withdraw, investors do not pay any taxes on distributions. However, the money must be used for approved expenses like college tuition, textbooks, and trade schools.

Smart tips for making the most of your 401(k)

There’s a lot of advice about handling a 401(k), but it can be mired in disclaimers and legalese. Come prepared to your financial advisor or accountant by watching this informative take on how to properly use a 401(k), from consolidating plans to some of the most common errors.

Mutual fund investors typically must pay a variety of different types of taxes associated with their investment, unless the funds are within tax-advantaged accounts like a 401(k) or IRA.

Traditional IRAs are tax-deferred—meaning you’ll pay taxes when you withdraw funds during retirement, rather than before you invest in the IRA

You can typically deduct traditional IRA contributions from your taxes. To invest in a Roth IRA, on the other hand, you must contribute money that has already been taxed.

Retail investors are getting burned by long/short strategies

In the US, many retail investors lack the SEC-mandated status (a high enough net worth, income, and other factors) to directly invest in hedge funds. The regulator considers hedge funds too risky for the masses. Hedge fund-like strategies have emerged as a workaround, despite potential pitfalls.

Certain trusts can bypass estate taxes—but the terms can't be changed

Putting money and other financial assets in an irrevocable trust is one way to avoid estate taxes. There are some cons to this trust, like the fact that you can't change the terms of the trust or assets in the trust after they're set. But a big pro is that any financial assets in an irrevocable trust aren't considered part of your estate, meaning they aren't subject to death taxes.

If you miss the April 15 tax deadline, you could be subject to penalties

This does not apply if you file for an extension. Otherwise, you could face failure to file penalties no matter how late you file your taxes—whether it's April 16 or May 16. The penalty is 5% of the tax due for each month (or part of a month) that your return is late, minus any taxes paid on time and available credits. If you file more than 60 days late, you could owe a minimum penalty of either $525 or 100% of the unpaid tax—whichever is less.

Many states offer a tax deduction for investing in their 529 plans

Different states offer different types of 529 plans (prepaid and savings), and they can require different minimum contributions. While some states offer tax deductions for residents who invest in their state’s plan, investors can choose to use a different state’s plan instead.

Health savings accounts are designed to alleviate upfront costs for high-deductible health plans.

Death taxes are placed on a deceased person's estate

Death taxes can include liquid cash, property, stocks, or other financial assets they owned. There are two main types of death taxes in the US: the estate tax and inheritance tax. Death taxes are levied at the federal and state level, but are targeted towards the rich.