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Series 66
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Textbook
Introduction
1. Investment vehicle characteristics
1.1 Equity
1.1.1 Common stock
1.1.2 Trading & the market
1.1.3 Stock splits & dividends
1.1.4 ADRs & foreign investments
1.1.5 Preferred stock
1.1.6 Preferred stock features
1.1.7 Convertible preferred stock
1.1.8 Restricted & control stock
1.1.9 Tax implications
1.1.10 Fundamental analysis
1.1.11 Technical analysis
1.1.12 Cash dividends
1.1.13 Common stock suitability
1.1.14 Preferred stock suitability
1.2 Fixed income
1.3 Pooled investments
1.4 Derivatives
1.5 Alternative investments
1.6 Insurance
1.7 Other assets
2. Recommendations & strategies
3. Economic factors & business information
4. Laws & regulations
Wrapping up
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1.1.9 Tax implications
Achievable Series 66
1. Investment vehicle characteristics
1.1. Equity

Tax implications

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Investors have two main ways to earn a return on stock:

  • Dividends
  • Capital gains

Stock taxation focuses on these two sources of return. You’ll want to understand how each is taxed and what the Internal Revenue Service (IRS) may require you to report and pay.

Dividends

A cash dividend is income received from common or preferred stock. Investors can also receive dividends from funds (e.g., mutual funds) that pass through income earned by the fund’s portfolio.

Dividends are generally taxed at lower rates than many other types of income. The key distinction is whether the dividend is qualified or non-qualified.

Qualified dividends:

  • Taxable at 15% for most investors

  • Taxable at 20% for investors at the highest income tax brackets

Non-qualified dividends:

  • Taxable up to 37% (based on income tax bracket)

Dividends are qualified when the issuer meets certain requirements and the investor holds the shares for a required holding period (you don’t need the specific rules here). Most dividends investors receive are qualified.

Qualified dividends are taxed at 15% for most people, while investors in the two highest income tax brackets pay 20%. Your reported income affects your marginal tax bracket (covered below): as income increases, the tax bracket generally increases. Only a small portion of taxpayers fall into the highest brackets.

A common example of non-qualified dividends is income from real estate investment trusts (REITs) (covered later). Because this income can be taxed at higher ordinary income rates, REITs often need to offer higher returns to attract investors. Non-qualified dividends are taxable up to 37%, depending on the investor’s tax bracket.

Sidenote
Progressive vs regressive taxes

The United States currently uses a progressive tax system for federal income taxes. That means higher income generally leads to a higher tax rate. You don’t need the bracket details, but the lowest federal income tax bracket is 10% (for low reported income), and the highest is 37% (for high reported income).

Estate and gift taxes are also progressive. An estate is the assets owned by a deceased person, which are eventually distributed to heirs and beneficiaries. For tax year 2026, the federal government taxes estates valued above $15 million, and gift taxes are only due on gifts valued above $19,000. In a progressive system, smaller amounts are taxed at lower rates (or not taxed at all).

A regressive tax system applies the same tax rate regardless of income level. Sales tax is a common example: whether you’re a billionaire or have no reported income, you pay the same percentage tax on items you buy. Excise tax (a tax on a specific good, like cigarettes) is also regressive.

Corporate investors can receive additional tax benefits compared with individual investors. Under the corporate dividend exclusion rule, corporations can exclude (and therefore avoid paying taxes on) a portion of dividends they receive:

Corporations can avoid paying taxes on:

  • 50% of dividends if owning less than 20% of the issuer’s common stock
  • 65% of dividends if owning 20% or more of the issuer’s common stock

Corporations often maintain brokerage accounts to invest excess cash, which can result in owning shares of other companies. For example, assume General Electric (GE) owns a small portion of Coca-Cola (KO) stock. If Coca-Cola pays GE a $100,000 dividend, GE will only pay taxes on $50,000. If GE owned 20% or more of Coca-Cola, it would only pay taxes on $35,000 of the $100,000 dividend payment (a 65% exclusion).

Dividends are reported annually on tax form 1099-DIV. Brokerage firms send this form to customers and to the IRS. The form shows the amount of dividends received and whether they were qualified or non-qualified.

Timing matters: for a dividend to appear on a given year’s 1099-DIV, it must be paid in that year. If a dividend was declared in 2022 but paid in 2023, it’s reported on the 2023 1099-DIV.

Capital gains & losses

A capital gain occurs when an investor sells a security for more than its original cost. The phrase “buy low, sell high” refers to earning capital gains. If a security is sold for less than its cost, the result is a capital loss.

A gain or loss is realized when the position is closed (long securities are sold, or short securities are bought back). To determine the gain or loss, investors compare cost basis to sales proceeds.

  • Cost basis is the total amount paid to buy the security, including any commission.
  • Sales proceeds is the total amount received when selling the security, minus any commission.

In other words, cost basis is what you paid in, and sales proceeds is what you took out. Here’s an example:

An investor purchases shares of ABC stock at $50 while paying a $2 per share commission. Several months later, the stock is sold for $70 while paying another $2 per share commission. What is the cost basis, sales proceeds, and capital gain or loss?

Can you figure it out?

(spoiler)

Cost basis = $52

The cost basis equals the purchase price ($50) plus commission ($2), which is the total amount paid to buy the investment.

Sales proceeds = $68

Sales proceeds equal the sale price ($70) minus commission ($2), which is the total amount received from selling the investment.

The capital gain or loss = $16 capital gain

Subtract cost basis from sales proceeds ($68 - $52) to find the gain or loss. A positive number is a capital gain; a negative number is a capital loss.

Capital gains can be long-term or short-term, depending on how long the security was held.

Long-term capital gains apply to securities held for longer than one year. Technically, the holding period must be one year and one day to qualify as long-term. Long-term capital gains are taxed similarly to qualified dividends: 0%, 15%, or 20%, depending on annual income.

Short-term capital gains apply to securities held for one year or less. Short-term gains are taxed at the investor’s ordinary income tax rate, which can be as high as 37% (similar to non-qualified dividends).

Capital gains and losses are reported on form 1099-B (B stands for brokerage proceeds). Each year, brokerage firms report customers’ gains and losses to the IRS. If the investor has more gains than losses (a net capital gain), taxes are owed. A net capital loss can be used as a deduction.

Sidenote
Selling specific shares

When you sell shares accumulated across multiple purchases, choosing which shares you’re selling can affect the reported gain or loss. Assume an investor dollar cost averages purchases over three years:

Year Purchase amount Price per share Shares purchased
2020 $10,000 $20 500
2021 $10,000 $25 400
2022 $10,000 $16 625

Unless otherwise specified, shares are sold on a first-in, first-out (FIFO) basis by default, meaning the oldest shares are sold first. Suppose the investor sells 800 of their 1,525 shares at $30 per share using FIFO. They would be selling:

  • 500 shares purchased at $20/share
  • 300 shares purchased at $25/share

Next, find the total cost of the 800 shares sold:

  • 500 shares cost $10,000 in 2020
  • 300 shares cost $7,500 (300 shares x $25 per share) in 2021

Total cost = $17,500 ($10,000 + $7,500), which gives an average cost basis of:

  • 800 shares purchased at $21.88 ($17,500 / 800 shares)

Selling at $30 per share produces an overall $8.12 per share gain ($30.00 sales proceeds - $21.88 cost basis).

The investor could instead sell shares on a last-in, first-out (LIFO) basis, which sells the newest shares first. Using the same sale of 800 shares at $30 per share, LIFO would sell:

  • 625 shares purchased at $16/share
  • 175 shares purchased at $25/share

Now find the total cost:

  • 625 shares cost $10,000 in 2022
  • 175 shares cost $4,375 (175 shares x $25 per share) in 2021

Total cost = $14,375 ($10,000 + $4,375), which gives an average cost basis of:

  • 800 shares purchased at $17.97 ($14,375 / 800 shares)

Selling at $30 per share produces an overall $12.03 per share gain ($30.00 sales proceeds - $17.97 cost basis).

Finally, the investor can use specific share identification, where the investor identifies exactly which shares are being sold. To minimize taxes, the investor typically sells the highest-cost shares first. Using this method, they would sell:

  • 400 shares purchased at $25/share
  • 400 shares purchased at $20/share

Now find the total cost:

  • 400 shares cost $10,000 in 2021
  • 400 shares cost $8,000 (400 shares x $20 per share) in 2020

Total cost = $18,000 ($10,000 + $8,000), which gives an average cost basis of:

  • 800 shares purchased at $22.50 ($18,000 / 800 shares)

Selling at $30 per share produces an overall $7.50 per share gain ($30.00 sales proceeds - $22.50 cost basis). Here’s a comparison:

Method Gain per share
FIFO $8.12
LIFO $12.03
Specific share $7.50

Of the three methods, specific share identification is the most tax efficient because it produces the lowest reported gain. Remember: the lower the reported gain, the less tax the investor pays. Specific share identification allows investors to reduce their tax liability to the lowest possible level.

Key points

Cash dividends

  • Taxable income received from common or preferred stock
  • Tax rates:
    • Qualified = 15% or 20%
    • Non-qualified = up to 37%
  • Reported on tax form 1099-DIV

Progressive tax systems

  • Higher taxes if more money involved
  • Examples:
    • Income taxes
    • Estate taxes
    • Gift taxes

Regressive tax systems

  • Flat tax rates
  • Examples:
    • Sales taxes
    • Excise taxes

Corporate dividend exclusion rule

  • Corporations avoid paying taxes on dividends
  • 50% exemption if owning less than 20% issuer’s common stock
  • 65% exemption if owning 20% or more of the issuer’s common stock

Capital gain

  • Securities sold for more than the basis
  • Reported on tax form 1099-B

Share selection methods for sales

  • FIFO
  • LIFO
  • Specific share identification
    • Is the best method to reduce taxation

Capital loss

  • Securities sold for less than the basis
  • Reported on tax form 1099-B

Long-term capital gain

  • Gain on security held more than 1 year
  • Tax rate: 15% or 20%

Short-term capital gain

  • Gain on security held for 1 year or less
  • Tax rate: up to 37% (income tax bracket)

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