3 Ways to Make Money in Company Stock
If your company offers you the opportunity to invest in its stock, it could come with some significant tax benefits and growth prospects.


Most employees are familiar with the company match on their 401(k) if it’s available to them, and many employers do the matching with company stock.
For example, if the employee puts in 6% or more of their salary into their company plan, the employer may match the first 3% dollar for dollar with company stock and the second 3% with 50 cents on the dollar.
However, there are three other lesser-known strategies involving company stock that can give employees significant tax benefits and/or the ability to buy the stock at huge discounts.

Sign up for Kiplinger’s Free E-Newsletters
Profit and prosper with the best of expert advice on investing, taxes, retirement, personal finance and more - straight to your e-mail.
Profit and prosper with the best of expert advice - straight to your e-mail.
Employee Stock Purchase Plans
Unless your company stock has poor fundamentals, it's pretty hard to beat a 15% return on your money before you even get started. This is because in most cases, employee stock purchase plans allow employees to buy their own company stock at a 15% discount from its current price.
Here is the catch: Assuming the stock goes up, the dollar amount of the discount will be taxed as less tax-favorable ordinary income, instead of being taxed as a long-term capital gain when the stock is later sold. The good news is that buying the stock at a 15% discount usually more than makes up for the higher tax rate.
Net Unrealized Appreciation
Remember also that at retirement, or when you leave a company, there is a unique tax break available for company stock held in a pretax company retirement plan. You are allowed to move the company stock in-kind, to a non-IRA brokerage account, instead of rolling it over to an IRA. This allows you to continue deferring tax on all the growth of that stock that occurred while in the company plan, until it is sold.
What's more, when you sell the stock, this growth, which is called net unrealized appreciation, will be taxed at the more favorable long-term capital gain tax rates, which are lower than the ordinary income tax rates you normally pay on withdrawals from company retirement plans or IRAs. This strategy can result in significant tax savings.
Keep in mind the original amount you paid for the stock inside your company plan will become taxable immediately as ordinary income, and a 10% early payment penalty tax will be incurred if you're not 55 or older when you withdraw the company stock.
Stock Options
Company stock can also be acquired by employees at huge discounts if their company offers stock options.
The most common type is the non-qualified stock option. This is where the employer offers the employee the opportunity to buy shares of the company stock at a pre-set price.
If the stock rises above that price, the employee still has the advantage of purchasing the stock at the preset lower price and putting the difference in his or her pocket.
For example, Jeff was given an option in year one to purchase 500 shares of ABC stock at the current market price of $50 a share. In year two he exercised part of his options and purchased 250 shares for $12,500 (250×$50). The fair market value of the shares at the time of the purchase was $18,750 (250 x $75). Jeff now has a $6,250 gain because he was able to buy the stock at a discount by exercising his stock options ($18,750-$12,500).
Whether Jeff sells the stock right away or not, this $6,250 gain is taxable as ordinary income in the year the stock was purchased.
If possible, it’s a good idea to exercise non-qualified stock options in years where you expect your income to be lower so you can trigger the tax in a lower bracket.
An "incentive stock option" works the same way, except the employee does not recognize income or capital gains until the stock is sold; therefore they have the advantage of tax deferral. Also, if those shares are held for at least two years from the date the option was granted and at least one year from exercise, the tax on the sale will be payable as a more tax-favorable long-term capital gain.
Keep in mind, that it can be a real temptation to invest too heavily in your own company's stock, because of either tax advantages or discounts.
This always has to be weighed against the risk of having too much concentration in one stock, subjecting you to substantial losses if your company goes bankrupt.
The employees at Enron, WorldCom and other firms that went under unfortunately learned the consequences of this the hard way.
Profit and prosper with the best of Kiplinger's advice on investing, taxes, retirement, personal finance and much more. Delivered daily. Enter your email in the box and click Sign Me Up.

-
Dow Dives 542 Points on Soft Jobs Data: Stock Market Today
The last day of a busy week ends with the first greater-than-1% move in either direction in more than a month.
-
Already Hit Your 401(k) Limit in 2025? Here's What to Do Next
Maxed out your 401(k) contributions, but still want to tuck away money for retirement? Here are seven ways you can take advantage of being a super saver.
-
How Much Income Will an Indexed Annuity Get You? An Annuities Expert Lays Out the Numbers
Guaranteed lifetime income sounds great, but how much will it be? Several factors determine your future payout on indexed annuities with an income rider.
-
Financial Fact vs Fiction: Why Inflation Is Lower, But Prices Are Not
Do you think bonds protect you from stock losses? Are you confident your assets will go to your intended heirs if all you have is a will? Think again — and read on for other myths that could be leading you astray.
-
I'm a Personal Finance Expert: Here's the Truth About Using AI to Plan Your Retirement
AI can be a useful tool, but it often gets important financial information wrong. It also can't emulate the empathy, judgment and personal connection you can get with a human being.
-
You Don't Have to Be Wealthy to Need a Wealth Manager
Navigating complex financial decisions is hard on your own, no matter how much money you have. A wealth manager can provide comprehensive financial planning, investment management, risk management and more.
-
Despite Tariffs, These Investment Experts Are Bullish on European Equities
European equities were one of the better-performing investments during the first half of 2025. They could be a good long-term prospect for U.S. investors needing to diversify, according to these investment managers.
-
How Do You Know You Are Ready for a Gray Divorce? 15 Yes-or-No Questions
As more people 50 and older get divorced, many splits are initiated by women who want a new path. Answer these 15 questions to see if you might need to think about how you should move forward.
-
'Buy Now, Pay Later' for Everyday Spending? This Financial Pro Thinks It's Risky
'Buy Now, Pay Later' apps can get you out of a jam when you need money quickly. But using them regularly for small purchases could create problems.
-
Five Things to Consider Before Rolling Your 401(k) into a Roth IRA
Converting at least some of an old 401(k) to a Roth IRA can offer long-term tax benefits and retirement flexibility, especially if you anticipate being in a higher tax bracket later or wish to leave a tax-free legacy.