Qualified Small Business Stock and ChatGPT

Qualified Small Business Stock (QSBS) is a critical topic that most founders are unaware of.

Instead of writing my own blog post about what it is and why it is important, I asked ChatGPT:

describe what qualified small business stock and why it is financially beneficial to people that have equity that qualifies as qsbs

And the answer:

Qualified small business stock (QSBS) is a type of investment in the equity of a small business that offers certain tax benefits to the investor. QSBS is generally defined as stock in a domestic C corporation that is acquired at its original issue, directly or through an underwriter, and that satisfies certain requirements regarding the corporation’s active business, gross assets, and length of time the stock is held.

One of the main financial benefits of QSBS is that it allows investors to exclude a portion of the gain from the sale of the stock from their taxable income. For example, if an investor buys QSBS at a cost of $100,000 and sells it later for $200,000, they may be able to exclude up to $100,000 of the gain from their taxable income. This can result in significant savings on taxes and make the investment more financially attractive.

Another potential benefit of QSBS is that it may qualify for a lower capital gains tax rate. Under certain circumstances, the gain from the sale of QSBS may be taxed at a maximum rate of 28% rather than the higher rates that apply to other types of capital gains. This can further reduce the tax burden on the investment and increase the potential return on the investment.

Overall, QSBS can be a financially beneficial investment for people who have equity that qualifies as QSBS, as it offers potential tax savings and may be eligible for a lower capital gains tax rate.

It missed an important point about how much tax exclusion you can benefit from so I followed up with:

What is the total amount of money an investor can exclude from the gain of the sale if the equity is treated as qualified small business stock?

And the answer:

The total amount of gain that an investor can exclude from the sale of qualified small business stock (QSBS) depends on several factors, including the amount of the gain, the length of time the stock was held, and the amount of the exclusion that was previously claimed on the stock.

Generally, an investor can exclude up to 50% of the gain from the sale of QSBS if the stock was held for more than five years. This means that if an investor buys QSBS at a cost of $100,000 and sells it later for $200,000, they may be able to exclude up to $100,000 of the gain from their taxable income.

However, the amount of the exclusion may be limited if the investor has previously claimed an exclusion on the same QSBS. In this case, the exclusion is limited to the greater of 10% of the stock’s adjusted basis (i.e., the cost of the stock plus any improvements made to it) or $10 million. For example, if an investor previously claimed an exclusion of $5 million on the same QSBS and the stock’s adjusted basis is $100,000, the exclusion would be limited to $10,000 (10% of the adjusted basis).

In summary, the amount of gain that can be excluded from the sale of QSBS depends on several factors and can vary depending on the specific circumstances of the investment.

Lastly, I needed an image for this post. So I asked Dall-e-2:

create an expressive oil painting of a dog in a suit, smiling, depicted as an explosion of a money flying all around them

The results:

So there are two really important and unrelated points here:

  1. If you are a founder or early-stage employee, you should internalize QSBS and speak with your accountant about it.
  2. It’s worth spending some time with OpenAI and ChatGPT. It’s wild and only took me 5 minutes to create this post.

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