What on earth is wrong with not paying taxes legally? What taxes does anyone pay other than those that they must pay?
If the government wants a tax to be paid they need to make it simple and unconditional. If there are loopholes or ways to legally avoid it, they will be discovered and people will take advantage of them.
What is legal and what is moral are two circles in a venn diagram.
In a good and just society there is a large overlap between them, and in others there is less overlap.
But it's impossible to build a legal system where there is a 100% overlap, and it would most likely be a broken society in other ways.
I totally agree with your second paragraph, that the government needs to remove loopholes and other ways for people to weasel out of contributing to society. But there will always be some corruption and a lot of money to be earned by only taking from our shared resources and never contributing back.
Sometimes law is analogised to software; in this analogy, loopholes are bugs.
One who exploits a bug is a hacker. An example of a life-hack is to arrange things to have lower taxation than those who wrote the laws were expecting.
But just as bugs in software are not meant to be exploited even though they can be, there are many loopholes in laws that are not meant to be exploited even though they can be.
Unless the law has a generic catch-all for tax minimisation schemes*, such minimisation may be legal, and yet frowned upon because it wasn't meant to be legal. Or even if it was meant to be legal, but you're rich and the general public thinks you're being unreasonable.
* I think the UK does? Or at least that's what it looked like HMRC was saying last time I was able to file my own taxes there…
That's what the issue is: there are loopholes, and far too many of them. The fact that some people get to deduct costs or have access to tax avoidance loopholes that most people don't have access to, is wrong. And governments don't do enough to fix this.
you could make an argument that in order to optimise your taxes, you have to be quite wealthy to begin with (hiring a tax guy, etc.) - otherwise you don't have any time left in the day to run your business.
so in practice, the little guy winds up just paying the 'sticker price' so to speak, while the big guy has pros who can make their big profits even bigger.
> What on earth is wrong with not paying taxes legally?
The issue is who is able to avoid paying taxes. The ability to reduce tax burden is largely possessed by people that make significantly more than the median income, so if you rephrase your question as “What is wrong with low- and median-earners subsidizing the wealthy?” then you’ll see people’s problem with it.
The actual functioning of everyday society and quality of everyday life are based on moral grounds. Legal grounds are a backstop, not a hand rail.
Those who exchange moral indulgences, clinging to legal grounds, are naturally and inevitably bound to accept the moral consequences. It's not just your Sunday school teacher making frowny faces at you: It's being afraid of armed robbery at every step because you have squeezed every bit of wiggle room out of every one elses' lives.
> What on earth is wrong with not paying taxes legally?
The primary anger is at the tax code.
> If the government wants a tax to be paid they need to make it simple and unconditional.
That’s the point. Making people aware of how the tax code is structured and how people take advantage of it is key to building support to change the tax code to what the people want.
If person A lobbies a self-serving loophole into the tax code, it's reasonable for person B to object.
> If there are loopholes or ways to legally avoid it, they will be discovered and people will take advantage of them.
Most loopholes take a certain amount of time and effort to exploit, so they only break even if you are above a certain income level. You don't "write ↑ ↑ ↓ ↓ ← → ← → B A on your 1040, collect $200." That's never how it works. It always takes effort to set up the necessary "excuses," this effort can be expressed as a dollar amount, and your dollar savings typically apply in proportion to your overall income, so a given loophole works AMAZINGLY WELL if you are ultra rich, ok if you are super rich, meh if you are rich, and it has negative expected value if you are not rich.
This is true for many things in life. Look for things expressed as a rate rather than a dollar amount. Then ask "what if the dollar amount that multiplied the rate was really big?"
Because all the poor people have zero room for creativity because it is designed to be so. The loop holes aren't accidental they are put their on behalf of all the rich people. Users taking advantage of them are part of a systemic swindle on behalf of the rich. Participating in such is therefore both fairly expected and still wrong.
You cannot make them "unconditional" without totally constraining all political freedom. The laws are rules that society imposes on itself. We all expect each other to operate within those bounds fairly, anyone who does not operate like that should be subject to digressional democratic liquidation. That is, forced bankruptcy with a simple majority.
If you're seriously asking why discussions like this exist...
One thing - and this may not be your intent - that often happens is that people will disingenuously use "nobody should do more than they have to" as sleight of hand to point in the direction of "oh it's the law that's bad" with no intent of actually encouraging fixing the tax code.
Another thing is that there's often a big difference between the letter and spirit of a law, since the laws are made by imperfect humans and other humans have FAR more cumulative people-hours available after the law is passed to find holes. There is likely no such thing as a "simple and unconditional" tax law that can't be worked around in ways its authors did not intend. And here this may seem circular - "then the government should patch the hole" - but of course that would be great and yet it is something the government is rarely incentivized to do when people with money give them that money to influence them to not want to.
Taxes are one of those funny defector games, that win you a free shave at the neck when you win to much. You not paying legaly gals the honest suckers who do into funny witchhunts, that when they come around make you wish you did.
> This is the Qualified Small Business Stock Tax Exclusion. Basically as long as you wait 5 years before selling the business, you won’t be taxed on the first $10 million dollars. This isn’t some loophole, this is exactly what it was intended for so that people are encouraged to take risks.
First this doesn't work for a Sub S only a 'C' corp.
Second, this wouldn't work in many cases when someone only wants to acquire the assets of the business and not the actual corporation in order to avoid liability going forward.
Note that typically the buyer would decide the issue (sure you with your 'small' business could say 'has to be corp' but that would potentially limit companies that would want to buy)
My point is the OP makes a broad statement "Business owners have the most flexibility of everyone to not pay their taxes. I personally think these things are questionable but its what I have seen others do over the last few years and what has been recommended to me by every top accounting firm in New York." and the benefit (like anything else is specific as far as the exact situation).
Edit: Want to make clear the liability is more than the money liabilities it's also potential lawsuits that hold over to the company acquiring.
If I understood correctly, it's "how not to pay taxes when selling your company".
At least some of the advice requires preparation years ahead. What happens if the company does not become as valuable as you expect it to, or at all? Or way more valuable, for that matter?
The headline is a bit clickbait-y. If your business turns a profit, it’s quite challenging to not legally pay taxes on the profits. Not to mention taxes owed on a salary you pay yourself.
If your business just has losses, I suppose it’s true you can eventually find someone else to sell to who apparently wants to spend a lot of money to buy your money-losing business?
Most investors know how to read a financial statements, selling such a business isn't the hard part. The hard part is keeping the IRS from coming after you for claiming it's a business and not a "hobby."
Step 0. In America, be rich to receive all of the legalized tax dodges to pay less than ordinary workers.
Also note that US citizens who leave the country and pay foreign income taxes elsewhere still have to pay federal income taxes just like the only other country that does this, Eritrea. The only way out is to renounce citizenship and be doxed in the Federal Register, pay lots of legal costs, and risk arbitrary demands for $10k fines for "not paying back taxes" and also being denied entry should it be determined for it was "economic reasons" any point in the future.
The problem with your article is that it’s extremely difficult to turn a company into a >$10 million asset value company for the founder and outside of the silicon valley VC world a company that doesn’t generate any net income isn’t worth $10 million. It’s not that simple to conjure up a $10 milliion company out of thin air.
So in the real world choosing QSBS stock results in electing into double taxation, so if you are starting a company to that will make net income that company is going to
Also, just to clarify, the article says save $10 million in tax in at least one place, but what you really mean is $10 million in capital gains taxable income, so really it is saving about 2.38 million in Federal tax (20% plus NIIT) plus the state if the state recognizes QSBS.
In my experience, most people benefit from QSBS after building a company for 10-15 years and selling for $3-7 million.
Similar mechanisms exist in the U.K. - entrepreneur’s relief/BADR allows you to pay a flat 10% on the full or partial sale of a business you founded, up to £1M - was £10M until 2020. You can of course do similar shenanigans with family to use their allowances too.
You can also of course emigrate to Portugal under the NHR scheme and between the fifth and seventh year sell whatever you fancy and not be liable for CGT anywhere.
1) be rich (or even better filthy rich)
2) go to PWC/EY/etc, pay them handsomely, let them work their magic
3) they got offices all over the planet and are updated on every single legislation/regulation around the planet
4) they (PWC/EY/..) make sure you use the very best ways, tailor-made to not pay taxes. This could mean thwt you need to move and live to some random village in Switzerland (IKEA dude, the writer of the Alchemist (Paulo Coelho)).
5) never pay taxes
If you read what I wrote, it doesn't even need to actually be 5 years if the person does some creative stuff with options which I have personally seen.
They don't have an additional capital gains tax, but they still tax you on capital gains. In fact they even tax you specifically on capital gains from savings and investments, but using a fixed assumed percentage gain irrespective of whether your actual gains were lower or higher than that percentage. And they are also going to change that law by 2028 so that it works like any normal capital gains tax. So if you can 10x an investment in the next 2.5 years you might save a bit, but after that it hits you like everywhere else.
If you are a US citizen then US tax will apply to you wherever you are. People form other countries switch off their home tax if they do not meet residency requirements.
There is no capital gains or wealth tax at all in New Zealand, but only for domestic investments. For offshore investments there is a deemed return that you treat as income, so if your wealth is tied up in illiquid stock then it can be dire.
is the author writing this article from the future? Peter Thiel is 57 years old (2025).
‘Peter Thiel famously bought his Paypal shares (which were valued at a few cents when he founded the company) into his Roth IRA account. When he turned 65, he was able to access the billions that the Paypal equity was worth with 0 tax on it.’
This advice is generally good. Used to give variations of this when I was still at a firm.
The most important one if you really want to avoid paying taxes on the sale of your business is to move to Puerto Rico and establish domicile there before discussions for a sale have commenced.
I don't understand how Thiel was able to buy his PayPal shares using a Roth. I thought you aren't allowed use your Roth to invest in a company you work for.
Can someone who knows more than me explain where I am wrong?
[+] [-] SoftTalker|8 months ago|reply
If the government wants a tax to be paid they need to make it simple and unconditional. If there are loopholes or ways to legally avoid it, they will be discovered and people will take advantage of them.
[+] [-] capitol_|8 months ago|reply
In a good and just society there is a large overlap between them, and in others there is less overlap.
But it's impossible to build a legal system where there is a 100% overlap, and it would most likely be a broken society in other ways.
I totally agree with your second paragraph, that the government needs to remove loopholes and other ways for people to weasel out of contributing to society. But there will always be some corruption and a lot of money to be earned by only taking from our shared resources and never contributing back.
[+] [-] ben_w|8 months ago|reply
One who exploits a bug is a hacker. An example of a life-hack is to arrange things to have lower taxation than those who wrote the laws were expecting.
But just as bugs in software are not meant to be exploited even though they can be, there are many loopholes in laws that are not meant to be exploited even though they can be.
Unless the law has a generic catch-all for tax minimisation schemes*, such minimisation may be legal, and yet frowned upon because it wasn't meant to be legal. Or even if it was meant to be legal, but you're rich and the general public thinks you're being unreasonable.
* I think the UK does? Or at least that's what it looked like HMRC was saying last time I was able to file my own taxes there…
[+] [-] mcv|8 months ago|reply
[+] [-] webdevver|8 months ago|reply
you could make an argument that in order to optimise your taxes, you have to be quite wealthy to begin with (hiring a tax guy, etc.) - otherwise you don't have any time left in the day to run your business.
so in practice, the little guy winds up just paying the 'sticker price' so to speak, while the big guy has pros who can make their big profits even bigger.
[+] [-] lokar|8 months ago|reply
[+] [-] jrflowers|8 months ago|reply
The issue is who is able to avoid paying taxes. The ability to reduce tax burden is largely possessed by people that make significantly more than the median income, so if you rephrase your question as “What is wrong with low- and median-earners subsidizing the wealthy?” then you’ll see people’s problem with it.
[+] [-] chillingeffect|8 months ago|reply
Those who exchange moral indulgences, clinging to legal grounds, are naturally and inevitably bound to accept the moral consequences. It's not just your Sunday school teacher making frowny faces at you: It's being afraid of armed robbery at every step because you have squeezed every bit of wiggle room out of every one elses' lives.
[+] [-] Aurornis|8 months ago|reply
The primary anger is at the tax code.
> If the government wants a tax to be paid they need to make it simple and unconditional.
That’s the point. Making people aware of how the tax code is structured and how people take advantage of it is key to building support to change the tax code to what the people want.
[+] [-] mystified5016|8 months ago|reply
The ultra-rich get tax loopholes and the rest of us have to make up for it with increased taxes and decreased government services.
[+] [-] smallmancontrov|8 months ago|reply
> If there are loopholes or ways to legally avoid it, they will be discovered and people will take advantage of them.
Most loopholes take a certain amount of time and effort to exploit, so they only break even if you are above a certain income level. You don't "write ↑ ↑ ↓ ↓ ← → ← → B A on your 1040, collect $200." That's never how it works. It always takes effort to set up the necessary "excuses," this effort can be expressed as a dollar amount, and your dollar savings typically apply in proportion to your overall income, so a given loophole works AMAZINGLY WELL if you are ultra rich, ok if you are super rich, meh if you are rich, and it has negative expected value if you are not rich.
This is true for many things in life. Look for things expressed as a rate rather than a dollar amount. Then ask "what if the dollar amount that multiplied the rate was really big?"
[+] [-] michaelmrose|8 months ago|reply
[+] [-] unknown|8 months ago|reply
[deleted]
[+] [-] barbazoo|8 months ago|reply
> It is incredibly simple to spin up an LLC or C corp and expense all kinds of things. Employees don’t get this benefit.
[+] [-] delusional|8 months ago|reply
[+] [-] majormajor|8 months ago|reply
One thing - and this may not be your intent - that often happens is that people will disingenuously use "nobody should do more than they have to" as sleight of hand to point in the direction of "oh it's the law that's bad" with no intent of actually encouraging fixing the tax code.
Another thing is that there's often a big difference between the letter and spirit of a law, since the laws are made by imperfect humans and other humans have FAR more cumulative people-hours available after the law is passed to find holes. There is likely no such thing as a "simple and unconditional" tax law that can't be worked around in ways its authors did not intend. And here this may seem circular - "then the government should patch the hole" - but of course that would be great and yet it is something the government is rarely incentivized to do when people with money give them that money to influence them to not want to.
[+] [-] ashoeafoot|8 months ago|reply
[+] [-] unknown|8 months ago|reply
[deleted]
[+] [-] gist|8 months ago|reply
First this doesn't work for a Sub S only a 'C' corp.
https://carta.com/learn/startups/tax-planning/qsbs/
Second, this wouldn't work in many cases when someone only wants to acquire the assets of the business and not the actual corporation in order to avoid liability going forward.
https://www.brickbusinesslaw.com/blog/should-i-buy-the-compa...
Note that typically the buyer would decide the issue (sure you with your 'small' business could say 'has to be corp' but that would potentially limit companies that would want to buy)
My point is the OP makes a broad statement "Business owners have the most flexibility of everyone to not pay their taxes. I personally think these things are questionable but its what I have seen others do over the last few years and what has been recommended to me by every top accounting firm in New York." and the benefit (like anything else is specific as far as the exact situation).
Edit: Want to make clear the liability is more than the money liabilities it's also potential lawsuits that hold over to the company acquiring.
[+] [-] lucianbr|8 months ago|reply
At least some of the advice requires preparation years ahead. What happens if the company does not become as valuable as you expect it to, or at all? Or way more valuable, for that matter?
[+] [-] coredog64|8 months ago|reply
[+] [-] trollbridge|8 months ago|reply
If your business just has losses, I suppose it’s true you can eventually find someone else to sell to who apparently wants to spend a lot of money to buy your money-losing business?
[+] [-] jimhi|8 months ago|reply
[+] [-] coliveira|8 months ago|reply
> pay taxes on the profits
There are techniques to show zero profits, or to get tax breaks on these profits. Some of the most successful companies do this.
> taxes owed on a salary you pay yourself.
You don't need to pay anything to yourself. Some of the richest founders proudly say they receive a $1 salary.
[+] [-] msgodel|8 months ago|reply
[+] [-] swat535|8 months ago|reply
[+] [-] burnt-resistor|8 months ago|reply
Also note that US citizens who leave the country and pay foreign income taxes elsewhere still have to pay federal income taxes just like the only other country that does this, Eritrea. The only way out is to renounce citizenship and be doxed in the Federal Register, pay lots of legal costs, and risk arbitrary demands for $10k fines for "not paying back taxes" and also being denied entry should it be determined for it was "economic reasons" any point in the future.
[+] [-] daft_pink|8 months ago|reply
So in the real world choosing QSBS stock results in electing into double taxation, so if you are starting a company to that will make net income that company is going to
Also, just to clarify, the article says save $10 million in tax in at least one place, but what you really mean is $10 million in capital gains taxable income, so really it is saving about 2.38 million in Federal tax (20% plus NIIT) plus the state if the state recognizes QSBS.
In my experience, most people benefit from QSBS after building a company for 10-15 years and selling for $3-7 million.
[+] [-] madaxe_again|8 months ago|reply
You can also of course emigrate to Portugal under the NHR scheme and between the fifth and seventh year sell whatever you fancy and not be liable for CGT anywhere.
[+] [-] HenryBemis|8 months ago|reply
[+] [-] sailfast|8 months ago|reply
The quieter and larger the exemption the better.
[+] [-] eli|8 months ago|reply
[+] [-] analyte123|8 months ago|reply
[+] [-] jimhi|8 months ago|reply
[+] [-] giarc|8 months ago|reply
https://www.mintz.com/insights-center/viewpoints/2906/2025-0...
[+] [-] jimhi|8 months ago|reply
[+] [-] bgnn|8 months ago|reply
[+] [-] sigmoid10|8 months ago|reply
[+] [-] lancewiggs|8 months ago|reply
There is no capital gains or wealth tax at all in New Zealand, but only for domestic investments. For offshore investments there is a deemed return that you treat as income, so if your wealth is tied up in illiquid stock then it can be dire.
[+] [-] tecleandor|8 months ago|reply
[+] [-] niklasbabel|8 months ago|reply
‘Peter Thiel famously bought his Paypal shares (which were valued at a few cents when he founded the company) into his Roth IRA account. When he turned 65, he was able to access the billions that the Paypal equity was worth with 0 tax on it.’
[+] [-] IAmBroom|8 months ago|reply
~100% of the posters use "loopholes" to refer to tax exemptions they feel are bad, and should be eliminated.
and
~100% of the posters believe some tax exemptions are good. These are not "loopholes".
Not in this thread: any objective rule by which these two ideas may be differentiated.
[+] [-] gamblor956|8 months ago|reply
The most important one if you really want to avoid paying taxes on the sale of your business is to move to Puerto Rico and establish domicile there before discussions for a sale have commenced.
[+] [-] readthenotes1|8 months ago|reply
Pretty sure it's 59.5, as long as the principal has been in 5 years.
[+] [-] HWR_14|8 months ago|reply
Can someone who knows more than me explain where I am wrong?
[+] [-] gamblor956|8 months ago|reply
[+] [-] jimhi|8 months ago|reply
[+] [-] v5v3|8 months ago|reply
https://youtu.be/YAJCvt9tOYE
(The donors to the politicians use these loopholes, so why would a politician end it...)
[+] [-] idontwantthis|8 months ago|reply
[+] [-] rob_c|8 months ago|reply