When I sold some shares in my company, it sure was nice to not pay any taxes thanks to QSBS. But it’s sort of an absurd handout to rich people — I have a hard time believing investment money would flee the US if early stage investors/founders had to pay long term cap gains on their first $10M of gains (after all, we’d still have carried interest to keep the VCs happy).
It’s also already really easy to multiply the limit, by gifting stock to your spouse, kids, or a trust — all of which can be done just before you sell and keep the benefit. So raising that limit just makes it more absurd.
Though, if you’re an employee at an early stage startup and you can afford it/stomach the risk, QSBS is a good reason to exercise your options early.
It is certainly a handout to rich people, but it does serve a purpose. If you have a choice to invest in a startup vs a more stable investment, the $10M (or now $15M) in tax free gains is a strong incentive to choose the startup investment over something else.
And at the end of the day, small businesses usually drive the most innovation, so getting rich people to direct their money into startups instead of big companies is good for the country as a whole.
This applies per person. When startup founders realize their stock is actually worth a lot they form trusts and each one gets QSBS. Each trust must be to a different person.
I personally know people who stack 5-10 trusts for as many family members as they can. This appears to give them 50% more tax-free money (10 to 15 million) per person in their trusts.
Don't forget QSBS benefits for investors. The exclusion limit is 10x invstment. If you invested $20 million (in a startup valued under $50 million), you could exclude up to $200 million in capital gains. It has to be a person, not a corporation who invests. I believe this would apply to the VCs, since you are getting money from a partnership fund. I could be wrong though.
So it applies to a situation when you hold stock of a company that's large enough to issue stock, but is, and has always been, small enough to never have more than $50M in assets, and you must hold the stock for at least 5 years.
Fairly common for startups that go through multiple rounds of funding.
If you invest during a seed round, chances are the funding is much less than $50M. Series A usually is much less than $50M too. Series B or C might put you over the limit, depending... but that doesn't disqualify the earlier purchases.
Meeting the holding period could be easy or hard, depending on what the company does. If it takes 5+ years between when it hits the $50M limit and when the shares are marketable, most holders will have a qualified disposition. If it's acquired and the merger terms aren't well tax managed, that may be a disposition for all holders and that sets the holding period. If it becomes marketable quickly, then some holders are likely to sell at least some shares before meeting the holding period... Avoiding capital gains tax is nice, but not nice enough to forgo realizing gains when experience has shown that stock prices can drop rapidly for a variety of reasons that may be hard to forsee.
The requirement was only that you acquired the stock when the company has less than $50M (now $75M) in assets. If the company now has $1B in assets, you still get the tax exclusion up to the limit on stock that was purchased back when the company was small.
It specifically advantages investment in small companies that then turn into large companies.
This also applies for options exercised before the company reaches $50M in assets. And then the gain from a valuation from $50M to say $1B is all excluded.
When I sold some shares in my company, it sure was nice to not pay any taxes thanks to QSBS. But it’s sort of an absurd handout to rich people — I have a hard time believing investment money would flee the US if early stage investors/founders had to pay long term cap gains on their first $10M of gains (after all, we’d still have carried interest to keep the VCs happy).
It’s also already really easy to multiply the limit, by gifting stock to your spouse, kids, or a trust — all of which can be done just before you sell and keep the benefit. So raising that limit just makes it more absurd.
Though, if you’re an employee at an early stage startup and you can afford it/stomach the risk, QSBS is a good reason to exercise your options early.
It is certainly a handout to rich people, but it does serve a purpose. If you have a choice to invest in a startup vs a more stable investment, the $10M (or now $15M) in tax free gains is a strong incentive to choose the startup investment over something else.
And at the end of the day, small businesses usually drive the most innovation, so getting rich people to direct their money into startups instead of big companies is good for the country as a whole.
This applies per person. When startup founders realize their stock is actually worth a lot they form trusts and each one gets QSBS. Each trust must be to a different person.
I personally know people who stack 5-10 trusts for as many family members as they can. This appears to give them 50% more tax-free money (10 to 15 million) per person in their trusts.
I actually just wrote about this in more detail last week: https://mrsteinberg.com/how-to-not-pay-your-taxes-legally-ap...
Don't forget QSBS benefits for investors. The exclusion limit is 10x invstment. If you invested $20 million (in a startup valued under $50 million), you could exclude up to $200 million in capital gains. It has to be a person, not a corporation who invests. I believe this would apply to the VCs, since you are getting money from a partnership fund. I could be wrong though.
'tight July 4 deadline (which is anticipated to slip further into the summer)'
Oops
So it applies to a situation when you hold stock of a company that's large enough to issue stock, but is, and has always been, small enough to never have more than $50M in assets, and you must hold the stock for at least 5 years.
How common is that?
Fairly common for startups that go through multiple rounds of funding.
If you invest during a seed round, chances are the funding is much less than $50M. Series A usually is much less than $50M too. Series B or C might put you over the limit, depending... but that doesn't disqualify the earlier purchases.
Meeting the holding period could be easy or hard, depending on what the company does. If it takes 5+ years between when it hits the $50M limit and when the shares are marketable, most holders will have a qualified disposition. If it's acquired and the merger terms aren't well tax managed, that may be a disposition for all holders and that sets the holding period. If it becomes marketable quickly, then some holders are likely to sell at least some shares before meeting the holding period... Avoiding capital gains tax is nice, but not nice enough to forgo realizing gains when experience has shown that stock prices can drop rapidly for a variety of reasons that may be hard to forsee.
The requirement was only that you acquired the stock when the company has less than $50M (now $75M) in assets. If the company now has $1B in assets, you still get the tax exclusion up to the limit on stock that was purchased back when the company was small.
It specifically advantages investment in small companies that then turn into large companies.
Real Assets != valuation. How much in assets do you think the average tech startup holds?
This also applies for options exercised before the company reaches $50M in assets. And then the gain from a valuation from $50M to say $1B is all excluded.
I think a lot of founders dont know about it.