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  • Writer's pictureLangston Tolbert

How Entrepreneurs Can Save Millions: Qualified Small Business Stock (QSBS)


In the world of taxes and finance, there's a hidden gem known as Qualified Small Business Stock (QSBS). It is a many times unbeknownst and often overlooked weapon that has the potential to save entrepreneurs millions in capital gains taxes. In this blog post, we're going to break down QSBS, show you how it can benefit C-Corp business owners, and give you some practical insights on making the most of this tax-saving strategy.

Navigating the Tax Landscape for C Corps

First things first, let's talk about C Corporations (C Corps). C Corps are often not tax advantageous compared to other entities because they are subject to "double taxation." Unlike simpler structures like LLCs and S-Corps, C Corps are seen as separate taxable entities. This means they're taxed at both the corporate and individual levels, (i.e., double taxation).

The Game-Changer - Qualified Small Business Stock (QSBS)

Now, here's where the magic happens. QSBS, found in Section 1202 of the Internal Revenue Code, is like a superpower for C-Corp owners. This tax-saving strategy lets regular folks who own small businesses and startups exclude a portion or even all of their gains when they sell QSBS they've held for over five years. But that's not all - these gains also get a free pass from the net investment income tax. And if you reinvest the proceeds into more QSBS, you can delay the tax bill.

To qualify as QSBS, the stock must meet two main criteria:

  • You've got to get it straight from the corporation when it's first issued, in exchange for money, property (with a few exceptions), or services.

  • The corporation's total assets at the time it's issued must not exceed $50 million.

The Sweet Tax Benefits of QSBS

QSBS isn't just another tax rule; it's a game-changer. It offers two significant tax perks for stockholders:

  1. Gain Exclusion: When you sell QSBS after holding it for more than five years, you can potentially exclude some or all of the profit from your taxable income, although there are some limits to keep in mind.

  2. Tax-Free Rollover: If you're into keeping your money in play, reinvesting the proceeds from selling QSBS into more QSBS can be a tax-free rollover of your gains.

For investors, QSBS can shield up to 100% of the gain from selling QSBS held for more than five years. The amount you can exclude is either $10 million or 10 times your initial investment, whichever is greater.

How Entrepreneurs Can Save Millions w/ QSBS - A Real-Life Scenario

Let's bring this down to earth with an example on how entrepreneurs can use this strategy to save millions. Imagine you're "A," an entrepreneur who grabs stock in "X Corporation" for $1 million and sells it for $20 million after five years. Since X Corporation's stock qualifies as QSBS, you can exclude $10 million from your gain. Even if your profit is $19 million, there's a limit, and it's set at $10 million. The basis used to calculate this limit may differ from what you use to figure out your gain, adding a bit of complexity.

The Fine Print - Limitations and Considerations

Before you dive headfirst into QSBS, it's important to know the fine print. There are factors like how you transfer stock, exercise stock options, and contribute property that can impact how QSBS applies to your situation. And here's a little secret: QSBS is only for C-Corps; LLCs and similar structures don't get a seat at this table.


Qualified Small Business Stock is like a golden ticket for entrepreneurs looking to cut down on their tax bills. By getting the hang of the rules and requirements, C-Corp owners can potentially save big bucks in capital gains taxes. If you want to explore this strategy further or uncover more tax-saving tricks, it might be a good idea to chat with a tax professional.

[Important Note: Always consult with a tax expert or legal advisor to get personalized guidance on using QSBS.]


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