11 Things Every Investor Should Know About Taxes

October 13, 2023

Taxes are an unavoidable reality for investors. While complex and often frustrating, having a solid grasp of the key tax implications for investments is critical, so you can make more informed decisions. The whole area of taxation is subject to change, so while we offer some general advice below, it is worth seeking bespoke advice from a tax accountant.

Here are some essential things every investor should know about taxes.

1. Capital Gains Tax

One of the most common taxes investors incur is capital gains tax. This applies when you sell an investment asset like stocks or bonds for a profit. The amount owed depends on how long you owned the asset before you decide to sell it.

  • Short-term capital gains - for assets held less than a year - are taxed at your ordinary income tax rate. This can be 10-37% depending on your total taxable income.
  • Long-term capital gains - for assets held over a year - are generally taxed at special rates of 0%, 15%, or 20% depending on your income. This favorable rate makes long-term investing worthwhile.

Knowing these differences can influence your investing and selling strategies. Holding assets over a year to get long-term gains treatment is usually wise if you have a choice.

2. Tax-Advantaged Retirement Accounts

Retirement accounts like 401(k)s and IRAs provide valuable tax perks for investors. The money you contribute lowers your taxable income now. It compounds tax-free over time and is only taxed when withdrawn in retirement.

Maximizing 401(k) and IRA contributions should be a priority for most investors. The upfront tax break plus tax-deferred growth over decades results in much larger retirement savings.

3. Investment Income Taxes

Investments like bonds and dividend-paying stocks generate regular investment income. This "unearned" income is taxed differently than salaries and wages:

  • Interest income is generally taxed at your ordinary income tax rate. Municipal and U.S. government bond interest is exempt.
  • Qualified stock dividends are taxed at favorable long-term capital gains rates.
  • Income distributions from mutual funds and ETFs are also taxed based on the composition of their underlying assets.

Tracking investment income and sales closely is important, as your marginal tax rate applies.

4. Wash Sale Rule

The IRS prohibits using wash sales to artificially generate tax losses on investments. A wash sale occurs when you sell an investment at a loss and buy it back within 30 days.

This rule prevents investors from deducting portfolio losses for tax purposes without fundamentally changing their position. It applies to substantially identical stocks or bonds.

5. Estate Taxes

Inherited assets receive a step-up in cost basis when the original owner dies. This means heirs only owe capital gains taxes on appreciation from when they receive the assets. The original owner's capital gains are essentially wiped away.

Estates worth over $12 million are subject to federal estate taxes of up to 40% as of 2023. Proper estate planning is necessary to minimize this burden on wealthy investors and their heirs.

6. Tax Loss Harvesting

Savvy investors conduct tax loss harvesting to lower their tax bills. This involves selling declining investments at a loss to offset capital gains or ordinary income. You can deduct up to $3,000 in net capital losses each year and carry over additional losses to future tax years.

Monitoring your portfolio for tax loss harvesting opportunities before year-end is prudent. The strategy aligns well with rebalancing and portfolio optimization.

7. Tax Preparation and Estimated Payments

Investing generates complex tax situations. Working with an experienced tax professional ensures you maximize deductions and avoid costly mistakes.

Depending on your situation, you may need to pay quarterly estimated taxes on investment income. Calculating these payments correctly avoids underpayment penalties.

8. Record-Keeping and Organization

Extensive investment records are essential for taxes. Keep detailed records of purchase dates, cost basis, sales proceeds, income received, fees paid, and other tax-related items.

Good organization makes tax preparation much smoother. Use brokerage statements, a ledger, or accounting software to have investment data handy.

9. State Income Taxes

Most states assess income tax on top of federal tax. Tax rates and rules vary significantly. Some states have no income tax, while California's top rate is 13.3% as of 2023.

Understand the income tax implications in your state, especially if you hold investments or conduct business across state lines. Retirees looking to move should consider state taxes.

10. Holding Periods

The aforementioned capital gains tax break for long-term (over one year) versus short-term holdings makes holding periods a key tax factor.

Savvy investors try to match holding periods with their investment strategy and objectives. Active traders fixate on short-term gains, while buy-and-hold investors benefit from long-term treatment.

11. Property Taxes

Property taxes deserve a section all of their own. They are levied by local governments and typically based on an assessed valuation of your real estate. Understanding how property taxes are calculated, when payments are due, and strategies to minimize the bite are essential for real estate investors, which is where tools like RE Cost Seg come in useful. Here are some key pointers:

  • Property tax rates vary drastically by state and county. Effective rates typically range from 0.5% - 2.5% of assessed value.
  • Assessment valuations trail actual market values. Prop 13 in California caps valuation growth at 2% annually until a sale.
  • Homestead exemptions, senior discounts, and other property tax relief may be available. Veterans, seniors, and disabled individuals often qualify for reductions.
  • Property tax bills are generally paid in arrears - e.g., 2023 taxes use 2022 assessments. Installment plans can ease the burden over the year.
  • Property tax deductions are itemized on federal returns and can offset rental income. Deductions are limited to $10,000 of state taxes as of 2023.
  • Understand how home improvements and renovations may impact assessed values for property taxes. Major upgrades can result in valuation hikes.
  • Appeal overly aggressive assessments if property tax bills spike. Provide comparable home values and be persistent if needed.
  • Property tax rates are a key consideration for real estate investing. High effective rates erode cash flow. Low rates enhance it.

The complex world of investing taxes can frustrate both novice and experienced investors, but taking the time to understand the key implications and strategies can save you a bundle while optimizing your overall returns. Consult experienced tax and financial advisors as needed and keep detailed records. With the right knowledge, investing and taxes can work together.


Carlos Diaz
I believe in making the impossible possible because there’s no fun in giving up. Travel, design, fashion and current trends in the field of industrial construction are topics that I enjoy writing about.

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