Tell HN: 100% exemption for angel investors extended through 2011

For years (since 1993), section 1202 of the U.S. tax code has provided a partial exclusion of gain realized on the sale of "qualified small business stock" (QSB stock) that is held for more than 5 years.

The big glitches under the law as it has heretofore existed: (a) the exclusion was only partial (for many years, only 50% but higher for qualifying stock acquired in 2009 and in 2010 prior to September 27); and (b) a portion of any gain that was so excluded had to be added back as a preference for AMT purposes. Thus, this exclusion had more limited value over the years that it has now, during this current window.

The benefit of a "section 1202 exclusion" today is that 100% of the gain realized is excluded (subject to a cap as discussed below) and the exclusion applies for purposes of both the regular federal income tax and the alternative minimum tax.

Thus, if a taxpayer today acquires qualifying QSB stock, holds it for more than 5 years, and then sells it at a gain, the gain on that sale will be completely free of federal income tax.

Who is a qualified buyer of such stock? The exclusion may be claimed by any "taxpayer" who meets the statutory requirements. It is not limited to "investors" but includes anyone who buys stock in a qualifying corporation and otherwise meets the section-1202 tests. This would include founders.

The exclusion may not be claimed if the taxpayer is a corporation. However, and this is important for VCs, angel groups and others who might be organized as some form of partnership, the gain from the disposition of qualified small business stock by a partnership, an S corporation, or certain trusts that is taken into account by a partner, shareholder or participant in such entity is eligible for section-1202 exclusion if (a) all requirements of section 1202 are otherwise met, and (b) the partner, shareholder or other participant held his interest in the entity on the date the QSB stock was acquired and at all times thereafter until the stock's disposition. Bottom line on this piece: corporations can't benefit from a 1202 exclusion but some entities can - check with a competent tax adviser on this - as can individual investors and founders.

A "qualified small business" under section 1202 is a domestic C corporation. An S corporation will not qualify; nor will an LLC.

In addition, to be a "qualified small business," the gross assets of the entity through the date of the issuance of the stock in question cannot have exceeded $50 million without regard to liabilities.

The business must also be an "active business" - that is, it cannot be an investment company (entities will fail this test if more than 10% of the value of their net assets consists of stock or securities, other than those of a subsidiary, and will similarly fail if more than 10% of their assets consist of real property that is not used in the active conduct of a qualified trade or business).

Concerning such "qualified small businesses," then, what is "qualified small business stock"?

This can be any stock in a domestic C corporation. Not preferred stock only, as might be purchased by outside investors. It is any stock, including common stock that is purchased by founders and others in a typical startup.

It must be stock that is "originally issued" to the taxpayer during the applicable time period (in this case, on or after September 27, 2010 through the date of expiration of the window for 100% exclusion). This means newly issued from the corporation. It can't be bought in a resale deal. Nor can the corporation and the taxpayer play games by trading equivalents (e.g., by redeeming x amount of stock from the taxpayer and then issuing it again to him); thus, it is not QSB stock if the corporation purchases any such stock from the shareholder/taxpayer within two years before or after the issuance of the shares for which the exclusion is sought. Section 1202 treatment will also be denied if, within one year before or after the issuance, the corporation redeems more than 5% of the aggregate value of all its stock as measured at the beginning of such period (certain redemptions, such as on death, are disregarded for this purpose).

Finally, to qualify as QSB stock, the stock must be acquired by the taxpayer in exchange for money or other property (not including stock) or as compensation for services provided to the corporation (this was the rule historically under section 1202 but please confirm with a good CPA or tax lawyer to make sure this carries forward during the 100% exclusion window - I think it does but am not 100% sure - to be safe, pay cash). Nothing in the rules specifies that the amount paid has to exceed any particular sum and so the amounts typically contributed by founders should generally qualify.

The 1202 exclusion is capped. Specifically, a taxpayer can exclude qualifying gain up to the limit of the greater of $10 million or 10 times the taxpayer's basis in the stock. Even more, this is measured "per issuer," meaning that someone who holds QSB stock in multiple, unrelated entities and otherwise meets the rules in each case would be able to exclude a potentially very large amount of gain if multiple entities proved to be success cases.

To sum up: if you as a non-corporate taxpayer acquire QSB stock during this window and hold it for more than 5 years, you will be able to realize substantial gains on the eventual sale of any such stock free of federal income tax.

Now, this is a very complex tax area and so you should definitely check with a competent tax professional before making important decisions here. That said, from the narrow view of startup founders and investors (and setting aside public policy concerns about the wisdom of this sort of legislation), this is a pretty amazing opportunity for those who have plan to invest or build out their ventures for the long term. With a whole year to plan for it (assuming this is finalized as anticipated), many interesting possibilities exist. Think of the above as suggestive, of things to consider in weighing options for such planning.

If you are like my company, and you have some small amount of convertible debt, and you are ramen-profitable but don't have a valuation, there are many reasons why this may not be worthwhile.

I'll leave it to Grellas to explain... note that this was prior to the extension of the law:

The “qualifying small business” (QSB) stock rules let anyone who invests in qualifying stock (meaning stock in a C corp) by December 31 of this year, and who subsequently holds such stock for at least 5 years, avoid any capital gains tax and also any AMT on the eventual sale of that stock...

... Pricing the stock also has implications for the grant of future equity incentives to other key people and so you need to consider not only pricing but also issues such as having to do a 409A valuation the next time you grant options to anyone in the company.

... The company would need to authorize their conversion in the absence of a qualified funding and will need to authorize a form of preferred stock into which they can convert. It is possible, of course, to have the notes convert into common stock but this puts a very high value on the common and makes it difficult to grant future incentive stock to key people without pricing it at a high level (the law allows as much as a 5 to 1 pricing differential between preferred and common and so, if preferred stock is used instead of common, you can still make future incentive grants at 1/5th the price of the preferred).

This led me to conclude that it's not worthwhile to convert, and George confirmed:

I think it is marginal for the company and its noteholders at this point and makes sense only if there is a fairly strong sense that people will hold for 5 more years. It would inject at least several thousand in costs (at least $10K, with some $5K to $7K out of pocket as a lump sum, if a 409A appraisal should be needed to price option grants and the like) and would add tax complications in terms of stock pricing in the short term – and so, yes, I would say you should likely skip it.

That said, if you are looking to invest in a great start-up and this tax break is meaningful to you, shoot me an email, and I'll send you my pitch :)

Previous discussion here: http://news.ycombinator.com/item?id=1972515 and http://news.ycombinator.com/item?id=1555363 and probably several others

Good news, but yeah, would love to see exactly the bill that you are referring to. Thanks!

Not a lawyer or accountant, but a very quick look says partnership/s-corp/homeowner (ha!) capital gains taxed at 0% extended 2 years if bought before end 2012, realized before end 2016. Options would count, I believe, but ask an expert. 100% exclusion from taxable income from startup investments made in 2011, but must be configured as an LLC. Also, mortgage interest and first-time homebuyer tax credits extended one more year. Some employment-based tax credits extended too, which might help fledgling startups a little.

It's lot of money just in terms of the tax incentives, as well as various benefit extensions and so on...from a financial planning standpoint it's like stimulus 2.0, $958 billion of red ink. Some economists are saying it's worth 0.5-1% more GDP growth next year. I worry it may be fiscal madness, but perhaps I'll be eating my words in 2 years' time.

Here's the text: http://tinyurl.com/2fc9ore (section 760) But there's not much to it.

http://www.gpo.gov/fdsys/pkg/BILLS-111hr4853enr/pdf/BILLS-11...

SEC. 760. TEMPORARY EXCLUSION OF 100 PERCENT OF GAIN ON CERTAIN SMALL BUSINESS STOCK. (a) IN GENERAL.—Paragraph (4) of section 1202(a) is amended— (1) by striking ‘‘January 1, 2011’’ and inserting ‘‘January 1, 2012’’, and (2) by inserting ‘‘AND 2011’’ after ‘‘2010’’ in the heading thereof. (b) EFFECTIVE DATE.—The amendments made by this section shall apply to stock acquired after December 31, 2010