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How long before someone comes up with a cryptographic approach to anonymizing bitcoin exchanges?

Perhaps exchange #1 could hold a database with bitcoin addresses and PGP-encrypted information about the bank accounts/mailing addresses of cryptocurrency holders.

Exchange #2 could hold the private keys of those bank/home details while receiving withdrawal requests and reimbursement for distributing bitcoin

The bitcoin holder can then request exchange #1 give a withdrawal request to exchange #2 in such a way that no exchange has enough information to connect a person to a bitcoin wallet.

Maybe I'm overthinking this; is there already a way that tech-savvy people can use Bitcoin in a way that's impossible to be tracked when converting to cash?

I mean, you can already use decentralized exchanges where you won't even have to give your name. I think for most people that are not doing anything illegal, there's no point in trying to evade taxes. The way I look at it, you either made lots of profits, so you'll have to explain where you got the money from anyways. Or you didn't make a lot of profit, why hide it? There won't be that much tax anyways.
> so you'll have to explain where you got the money from anyways

Explain to whom?

To your bank? Presumably if you made a lot of money, you'll be buying some houses and maybe some cars or creating your own businesses or something. If you transfer large amounts, it might get frozen if you can't explain the origin (kyc/aml).
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Assuming you're being facetious, I have always wondered where the line is. If I discover ten thousand dollars in cash in a hole in the ground and deposit it, will the IRS notice? Will the bank require some kind of information? What about if it's a hundred thousand?
The bank will have to report it to the IRS. They will cross-reference it with your taxes. They will also come talk to you if you have a pattern of doing it regularly. But you will probably not have an issue with it.
Yes, When large amounts of money are deposited into an account there is an automatic notice sent to the government. A One time event shouldn't be an issue however if you have multiple events of large deposits then it's going to trigger algorithms and the government is going to start asking where you got the money from and they'll perform an audit. If you attempt to bypass the system they have systems in place to detect that and will perform an audit. Just pay your taxes
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> Will the bank require some kind of information

Crypto doesn't go through the banking system. Miners for example can spend the mined crypto and for all practical purposes nobody will ever know.

Try depositing 50k at any US bank. Instant paperwork. Try depositing 10k. No questions asked.
Coinbase, for one. There's a whole process under the KYC/AML regulations if you want to deposit large amounts of crypto with a legit exchange.
I'm not from the US but my understanding is that even if you're doing illegal stuff there's still no point in trying to evade taxes, as IRS is not allowed to notify anyone about where you got the money from anyway.

"Illegal activities: Income from illegal activities, such as money from dealing illegal drugs, must be included in your income on Schedule 1 (Form 1040), line 8, or on Schedule C (Form 1040) if from your self-employment activity"

They thought of everything!

I think the point of this is less that the IRS won't report it to someone else, but that it adds tax evasion as a reason a criminal can be pursued.

You are probably thinking it's like where contact tracers or census workers or whatever aren't supposed to report illegal immigrants because it's more important that they get accurate info than report people to ICE. I don't think that's the case with the IRS, they're probably more than happy to let other agencies know about your illegal activity.

I got it from here (https://money.cnn.com/2013/02/28/news/economy/illegal-income...):

"If you tell the IRS you made $1 million from stealing money or dealing drugs, does the agency tip off the cops? Legally, it can't, unless a law-enforcement agency gets a court order granting it access to a specific taxpayer's return. The IRS isn't supposed to proactively alert other agencies about misdeeds unless terrorism is involved. In that case, it still needs a court order to disclose anything, but the IRS can initiate the legal process on its own."

I have no idea if it is still valid or not.

Definitely still valid. When I trained as a tax preparer for the VITA program (which involves training specified by the IRS), this was a key point of the training. We were also told that information from clients was confidential and we couldn't report to anyone outside the IRS that someone was earning money illegally. The software (paid for by the IRS) even had built-in workarounds for reporting income for someone with a fake SSN on their W-2 because they didn't have work authorization.

I did this for multiple years, and some of the volunteers had been doing tax prep for over a decade. The same clients came in year after year. If we couldn't guarantee that their tax information was safe from ICE, they would definitely have stopped coming.

It's called thorchain and it's on the way to the moon...
> Maybe I'm overthinking this

Definitely. What you’re describing would certainly be a conspiracy to violate all sorts of American laws and is punishable by a lot of time in jail. Add one more layer to your process and you qualify to be prosecuted via RICO laws!

Why do this on behalf of a bunch of random folks you’ve never met?

I'm sorry, but I don't understand the mindset here. Having created something whose only advantage is in money laundering and paying for illegal products, having created something that by its nature has and always will have massively wasteful consumption and externalities, you're now looking for a way to avoid paying the taxes that support society?
"Externalities" isn't the right word to use here; Bitcoin miners pay for the resources they use to mine Bitcoin.

But there is a positive externality associated with Bitcoin, in that it serves as a check and a balance against authoritarian governments, present and future.

Hence why it's important to ask these questions.

>"Externalities" isn't the right word to use here; Bitcoin miners pay for the resources they use to mine Bitcoin.

Yes it is, Bitcoin miners are overwhelmingly located in China and powered by highly carbon-intensive coal plants. The costs of those emissions are not borne by the transacting parties, because they are global and intergenerational. Regardless of whether Bitcoin miners pay for their coal-powered electricity, their revenue is effectively subsidised by externalities. The higher the demand for Bitcoin, the greater those externalities.

I don’t get it, are you proposing that alternative currencies like USD are completely carbon neutral and have no externalities?

Personally, I am not aware of any currency that does not have externalities, most currencies have a sizable body count from the wars required to preserve their value. Presumably, once Bitcoin is fully mined it may end up having the least externalities of any currency, past or present.

> Presumably, once Bitcoin is fully mined it may end up having the least externalities of any currency, past or present.

The "mining" is of "new" Bitcoin is utterly and completely irrelevant to the the power consumption. The power consumption is the goal, in order to verify that enough power has been sacrificed so that one is allowed to update the ledger. The "new" Bitcoin is an addition to the ledger without a corresponding subtraction, a creation of something from nothing, done as an incentive for transaction validators to spend such tremendous amounts of electricity. As that incentive goes away, transaction fees will increase in order to cover the cost of electricity.

At all times, cryptocurrency resource consumption must be proportional to the total value represented by that cryptocurrency. Anything less than proportional, and the network would be vulnerable to attack. This is independent of the particular mechanism used to incentivize the waste of resources.

Energy usage is absolutely an externality for almost exactly the reason you claimed it's not. The miners pay the electricity company but the electricity company's price doesn't take pollution into account.
No one is avoiding anything. It’s governments that are mistaken in thinking they have the authority to tax the private exchange of digital assets. Sure they can try, but at the end of the day decentralized anonymous currency and centralized taxing authority are fundamentally incompatible.
Almost the stupidest thing an investor can do is try to illegally evade taxes. It is pretty much all downside and no upside if you walk through the likely outcomes.

Either double theoretical, paper wealth or lose actual time to a jail. One of those is realer than the other.

Avoiding taxes is critical, but breaking the law is foolish.

That doesn't matter, you still need a way of turning 50 USD into crypto. You can either give a random stranger 50 USD on the street for X crypto - some kind of a black market fee or you give coinbase 50 USD via credit card and it's in your account immediately and a reputable company backing it.

The more "illegal"/gray crypto becomes the less it is worth, the worth (at least at todays scale) is due to the ease of use/popularity. It's super easy to buy 1 BTC right now, go back 5 years you basically needed to know someone who knew someone or be part of a forum and hope the other person didn't scam you.

I wish they had kept the like-kind treatment for crypto-to-crypto exchanges. Or that they had given very clear guidelines and rules on crypto taxation. Or that they had lowered crypto tax rates a little because it's highly risky anyways.

Nowadays, I see a lot of people just borrowing against their holdings to avoid triggering taxes, especially for long term holders who might be up 1000+%, there's really no point in cashing out, since a significant chunk will just go to the gov (especially if you're in California or New York).

There's "really no point" in cashing out returns of 1000%?

If I had put 100k in, my coins would be worth 1M. Even if my taxes were 30%, I'd be walking away with 730k. That's an astronomical gain.

A fine is a tax for doing bad.

A tax is a fine for doing well.

A tax is a subscription fee for the privileges of citizenship. There are many millions of people who would happily become "subscribers" in return for becoming US citizens.
Failing/refusing to pay a subscription fee does not, generally, result in you getting thrown in a cage with rapists and murderers.
> Failing/refusing to pay a subscription fee does not, generally, result in you getting thrown in a cage with rapists and murderers.

If you fail to pay the subscription fee for your gym, but break in to use the equipment anyway, it might.

To take the analogy a step further, a gym subscription is optional. Paying taxes is not.
> To take the analogy a step further, a gym subscription is optional. Paying taxes is not.

You're pushing the analogy too far. You're not an autarky, there's plenty of stuff you have to pay for that isn't optional (e.g. food, shelter, etc.).

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Sometimes local mobs force you to pay them protection money. If you don't pay, they will take your property or even commit violence against you, exactly like the state. If you do pay, they will provide valuable services to you such as making sure you don't get robbed. Do you feel it would be reasonable to call this a "subscription fee"?
Hmm,i wonder why i as a non immigrant don't qualify for this citizenship even after paying all taxes, including FICA
Do you use roads, sidewalks and other public infrastructure? If so you should pay into the system.
Do you earn your money from that system?

Salary taxation usually means you are earning your dollars by being part of a functioning society.

There are billions of people who would happily become "subscribers" to a US job market, even if the offer required that 50% of their income was ritually burned for no benefit to the “subscriber”.

Now capital gains are perhaps a different argument…

A tax is (a tax for doing bad) for doing well?

You may have a tautology to clean up there, bud.

If you try to apply the Peano Axioms on pithy aphorisms, you're gonna have a bad time.
At the expense of the pot calling the kettle black, this comment epitomizes behavior that I don't like to see on HN: the condescending and incorrect use of technical jargon in an internet argument that adds no new insight. In what way whatsoever are the natural numbers relevant to the post, let alone parent comment?

Please rethink signal-boosting off-topic comments in the future.

Sure, but you can borrow 730k and still hold on to the asset, why not do it?
Because if your coins go down to $100k, you're going to get margin called on your borrow. Given the volatility of crypto, you wouldnt want to borrow more than 10% of your funds.
Yes, you have to be carefully not to get margin-called, from what I've seen most people that have over 10M+$, tend to borrow up to 25-30% of their collateral's value (for example[1], this person borrowed 82M$ using 228M$ worth of collateral).

1: https://defiexplore.com/cdp/9167

There is no way to be "careful not to get margin-called", since crypto markets are heavily manipulated in order to force margin calls. Trading on margin on crypto markets is a fool's game.
Notice that borrowing != trading on margin, you can certainly buy back into the asset, but you can also do lots of other things with the money. You can be careful with your borrowing, like the example I gave, in that case, Bitcoin would need to drop by 50% before that person get's liquidated and even if that happens, they still have the 82M$ in cash.
>> You can be careful with your borrowing, like the example I gave, in that case, Bitcoin would need to drop by 50% before that person get's liquidated and even if that happens, they still have the 82M$ in cash.

Not quite...now you still owe capital gains tax on the forced liquidation price (minus cost basis)! So perhaps a large part of your $82M draw goes into taxes.

You're making me think that maybe I shouldn't have sold puts on DOGE, levered myself up 20x, and wait for it to go to the moon. There's no way I can lose!
At least in a bull market, it seems safe to assume that an asset like BTC or ETH will not suddenly decrease by over 50%.
It is definitely not safe to assume anything in the incredibly corrupt and manipulated cryptocurrency markets.
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Because you might lose that 730K, since you’re still exposed to a very volatile market.
The 730k is already in bank account, you'd only lose the collateral in case of liquidation, but that doesn't matter because your alternative was to sell it altogether.
You can’t use the 730k then but you are now accruing interest on it, so what’s the point in having it?
So I have 730k in bank account, but instead of using it, I borrow 730k and spend that money (how do you even decide "which" money you are spending anyways, it's all money) and pay interest on the loan? Why would I do that?
Not sure I understand what you mean, you only have 1 730k which you've borrowed. Interest rates are a drop in the bucket (~4%) compared to ~25-40% tax rates and that's ignoring asset appreciation (BTC averages ~300% YoY). If you use something like makerdao, you won't even have to pay a single cent of the debt back as long as you borrow conservatively and don't need your collateral back.
If you think that asset is going to go down, you'd rather just sell it than borrow against it, no?
Because there will be an annual interest rate to borrow and there is always margin call risk given the vol of crypto
>Nowadays, I see a lot of people just borrowing against their holdings to avoid triggering taxes

That seems excessively risky. Let's say you borrowed some USD using bitcoin as collateral, and bitcoin drops. Then what? Presumably you've already spent the money so now you're in debt and can't pay it off because your bitcoin holdings have dropped.

It'll get liquidated if it drops by say 30%, but that's what you would have paid in taxes anyways. You get the same amount of cash either way.
wouldn't you have to pay taxes on the 70% left over and you wouldn't have enough to service the debt?
Yes, so ideally, you wouldn't borrow so much to be margin called, it's over-collaterized, so you'll always have enough to service the debt.
Would you go 3x Margin Long on the S&P 500 and then take out a loan against that to buy things? Because that's basically what you are doing if you take out a long against your crypto holdings. I would be very, very careful about touching it.

This strategy, but applied to developing nation currencies and the dollar has ruined many an economy (ruble crisis, euro crisis, Asian currency crisis, etc). When your obligations are in a different currency than your assets, it's danger zone. People become blind to risk in a bull market - crypto can certainly drop 90+% and wipe out anything you have borrowed against it.

>It'll get liquidated if it drops by say 30%,

Doesn't this trigger a taxable event? If not it seems like it's pretty easy to bypass taxes by borrowing against your bitcoin and then liquidating it if it drops 1%. In addition to that, since it's a loan, you're theoretically stuck paying interest on it forever. Assuming 5% APR, you'd reach break-even in about 5 years.

Well if you use something like maker, you can keep the loan open for pretty much forever and not pay a single dime of interest as long as you don't want your collateral back and make sure to not get liquidated. Ideally, you borrow a little conservatively to avoid liquidation.
This whole thing only really works if you're a crypto bull. If you think crypto is here to stay and will go to the moon then yeah, there's no problem borrowing against it, since you expect its value to go up. However, if you're a crypto bear or want to derisk your holdings, this is a terrible idea because you still have exposure to the price of crypto. Selling on the other hand, eliminates your exposure entirely.
If you made 1000+% holding on to crypto (and not selling at any earlier point in time), you're presumably a crypto bull, right?

It eliminates your exposure at the cost of ~25-35% (depending on where you live and potentially up to ~45% if Biden's plan passes), so it only makes sense if you're certain that the market will drop by more than that.

>It eliminates your exposure at the cost of ~25-35%

No it doesn't. Eliminating the exposure would mean your net worth would stay the same regardless of whether it goes up or down. That's the case if you sold your bitcoins, but not if you took out a loan.

The super annoying thing about the Biden plan is that it retroactively affects stuff that happened this year that people weren't planning for. It should be a law that any changes to tax policy kick in the fiscal year after the law is passed.
That's not an annoying thing, that's the whole feature. The point is to prevent people from avoiding the tax - if the tax was announced and not applied retroactively, people would change their behavior to avoid it (or sell right before the tax was raised). That's precisely what you want to avoid to be fair to everyone.

The point of a tax is to redistribute the money a government thinks should be redistributed to account for externalities in the market (and support social / infrastructure programs).

Isn't that a bit defeatist? It's like admitting that people will find ways around it. It'll only work in the first year when it's introduced.
yeah but most taxes don't change from year to year. Moreover, if your year zero advantage is "the point" then, why isn't biden announcing the tax changes in november and ramming them through?

> The point of a tax is to redistribute the money a government thinks should be redistributed to account for externalities in the market

That is not the point of a tax. The point of a tax is to raise revenue for government programs. That includes bombing children on the other side of the world, financing explorations to space, bailing out boeing and goldman sachs, etc. Nowhere in tax law does it say "redistribute to account for externalities in the market". Just because you dream something ought to be so, does not make it so, now or ever.

Well, even more technically, the point of taxes (and QT) is to remove liquidity from the system when inflation gets overheated (since we can print money / have the FED monetize the deficit to pay for our spending if we need to).
Why would you be in crypto if you're a crypto bear?
Well, now you have to pay 28% in taxes on the liquidated value rather than 30% on the full value. You don't actually get the same amount.

If you had X, you would pay 0.3X in taxes - if you got liquidated at 0.7X, you pay (0.7X * ~0.28 = 0.2X in taxes). So in this case your net goes from 0.7X to 0.5X, not stays the same.

What you can do is get a hedge (short via futures or options) on your long position to flatten yourself against the market (or part of your position) - basically creating synthetic dollars, and then take out a loan against that. The only problem is margin maintenance on the futures position or rolling the option for however long you need the loan for (Likely you would do this option if you want to spread out liquidating your crypto over multiple years for more favorable tax treatment).

They are probably talking about on chain borrowing on Ethereum using Maker or Compound or one of many other similar contracts. In this case, if the price of crypto drops to the point that the amount you borrowed is more than the crypto you put up for collateral, you either need to put more crypto into your position to keep it collateralized, or the position will be liquidated, losing you the crypto and triggering the capital gains taxes you were trying to avoid.
> Nowadays, I see a lot of people just borrowing against their holdings

Perverse incentives setting us up for disaster. I don't really care about crypto until it becomes heavily leveraged, after which it's basically 2008 again.

Unfortunately, it's even worse on some exchanges that offer up to 125x leverage to people who might not even understand what they're doing properly. That's why you see flash crashes every once in a while, couple weeks back there was billions of dollars liquidated.
It’s unlikely ever to be a 2008 like event. Mortgages were considered safe investments so banks leveraged to invest.

No credible bank is going to leverage to speculate on crypto. They might create products to let their customers do it, but they’ll make sure their books have little exposure.

They are selling shovels; not panning for gold.

> Or that they had lowered crypto tax rates a little because it's highly risky anyways.

That'd be a fun principle applied to stocks. Pay less in capital gains as more leverage is employed. That's a wacky feedback loop to throw into any market.

I'm sure they'll come after them with the same fury they go after alleged billionaires paying $800 in taxes for a year.
The IRS stopped auditing those people a while ago, because they cost too much up front to audit and sue. It’s the middle tier where all the audits happen; rich enough to evade their taxes, but not so rich that they can afford good lawyers who make collecting difficult.
In general, the word isn't evade. In general, it's "plan" or "structure".

It's less worth pursuing the ultra wealthy because they implemented the actual tax algorithm and paid every penny the law actually requires -- often zero -- when the algorithm is executed flawlessly.

For the disciplined tax planners to pay more, the code has to be debugged and simplified to eliminate these unintended but fully accurate results.

Spoken like a true thief. "How can this be stolen? What is possession, really?"
That sounds like an excuse. The reality is that the government is controlled by rich crooks.
More a consequence of the IRS being systemically underfunded for decades. They simply do not have the money required to audit everyone, so they’re pursuing a strategy of maximizing the return per audit dollar spent.

Culturally, I’m sure that the IRS wants to catch every tax cheat; it’s just that they lack the resources to try.

Expecting billionaires to ever pay seems naive.

The amount you're threatening to tax them is literally the resources they have to mitigate that tax. If you want to tax them say 7 million, it's worth spending 6.5 million if it got that bill down to anything lower than 500K and if you ever had a way to hold them at gunpoint to get them to pay, they'd just move themselves and their HQ another country.

Taxes are only for the working class and the middle class.

There may be a fundamental disconnect between what the currencies are (or how they are used) and how they are taxed.

This issue of lots and being taxed as property:

>For example, say that someone sold bitcoins at $22,000 each in December 2020 and had coins bought 2016 for $600 and 2017 for $16,000. Selling the 2016 coins would mean a taxable gain of $21,400 each, while selling the 2017 coins would mean a gain of $6,000 each—a big difference.

This is not like a currency, where if I had a stack of Euros from an old holiday and then exchanged them for USD or even bought something with them, there is no concept of "lot" price in a currency. This US law definition appears to in effect destroy the fungibility property of cryptocurrencies by pinning the non-fungible identity of the coin to its spot price at the time of transaction. If US law doesn't treat it as currency, it's basically not currency.

I sat on the sidelines on cryptocurrency from the beginning because of specific scenarios like this because of these very inevitable problems. What they really are is an exotic asset for getting portfolio exposure to the trillions of dollars in black and grey market economic activity and associated volatility properties, but with only arms length participation. Basically a way to particpate in a distributed bank that launders money while turning a blind eye just like the real banks.

However, remote tech has changed work so much that if I were a betting man, I would be looking at real estate in non-extradition countries as thousands of new crypto millionaires weigh their options and just leave.

>This is not like a currency, where if I had a stack of Euros from an old holiday and then exchanged them for USD or even bought something with them, there is no concept of "lot" price in a currency.

But are they taxed? ie. if you sold your euros now, you'd probably realize a modest profit since USD went down recently. Are those gains tax-free?

Effectively yes they are tax free because there’s no easy way for irs to enforce. By law though you need to pay taxes on those gains. If you use a trading platform for trading, there’s probably a better chance of getting caught if you don’t pay taxes. There’s really nothing different here.
No, forex trading is taxed as capital gains, like any other asset.

It also opens up an interesting loophole for companies with cash streams in other currencies, if those currencies are falling in value relative to the dollar. They can cover their local costs in local currency but then convert profits to USD and declare a loss for a tax writeoff.

Can you reference the formal accounting and financial mechanisms under which this activity supposedly generates a tax write-off?

Specifically: a tax write-off that is not also an actual economic loss.

If instead of "selling" or "exchanging" those Euros, the purchasing power of those Euros may have changed as the result of inflation, PPP, used lamborghini prices, etc. The change in value depends on the change in value of what you have marked it to. Direct USD exchange, there's huge profits/loses because of the volatility of cryptocurrencies vs. USD.

But NFTs...these become a kind of volatility cold storage.

I'm not trying to mentally hack tax law, I'm suggesting that the law as described in an example by a journalist would show cryptocurrencies are not currencies, and now that the US is making enforcement a priority, they are collapsing the uncertainty bubble in which the whole market has operated.

The invention of cryptocurrencies was a tax revolt to begin with, and it probably makes more sense to look at policy through this lens than any other.

What you describe is how assets are typically taxed. And as far as I know, this includes currency you purchase and later sell for a profit.

It's called a cost basis.

Unless you are suggesting purchases made with Bitcoin (that aren't converted to fiat currency first) are taxed, which I'm not sure is the case.

But given the cash side is unenforcable because of this property of fungibility, it's more like casino chips where you pay taxes on them when you cash them in?
Well, you've recorded the cash transactions in a public ledger, so it may be more enforceable than one thinks.
>it's more like casino chips where you pay taxes on them when you cash them in?

I'm not sure whether the IRS would buy that argument. If you won $1M (in chips) at a poker tournament I doubt the IRS would let you report your winnings across 10 separate years to reduce your marginal rate. The tax is on income, which is earned when you won the tournament, not when you cash out the chips.

The IRS would however probably allow you to treat the entire thing as a zero-cost basis and pay extra tax to not have to deal with the paperwork. Depending on the scale of the profits and the scale of the paperwork, that might be worth it.
I believe this is the same as any other fungible assets, e.g. if I buy a share of Google for $1000 and then a year later buy another share of Google for $2000, then sell one share.
It sounds like it's more like RSUs or other stock grants, where your taxes vary based on when you received _those particular_ shares.
Where the disconnect is is between "currencies" and "cryptocurrencies". The latter are "currencies" basically in name only, and share almost none of the properties of the former.
> However, remote tech has changed work so much that if I were a betting man, I would be looking at real estate in non-extradition countries as thousands of new crypto millionaires weigh their options and just leave.

Taxes are there to support the infrastructure that powers a country. If someone opts to not pay their share of taxes and leave, they are also not using the infrastructure paid for by taxes. Effectively, if you want to drive on nice roads, have consistent access to clean water and power you can pay taxes.

The part that makes it force is that even if I were willing to go without those things, I can't _not_ pay taxes.
I think you're being disingenuous with this reply. You cannot physically live in a country and not use their infrastructure.

If you don't like ALL the things taxes are used for you are welcome to leave and go elsewhere.

> If you don't like ALL the things taxes are used for you are welcome to leave and go elsewhere.

Yes because customs and immigration will just welcome you with open arms.... /s

It is simple:

Country X isn't willingly keeping people because countries Y and Z won't welcome a person in. If you want to live in a country you have to abide by that country's rules. This includes paying taxes as defined by that country's tax laws.

Country X is effectively keeping people because the only place you can freely and legally enter and permanently reside in is Svalbard. Otherwise you have to immigrate illegally or with some prior arrangement.
What is your point beyond being argumentative and not providing any substantive value to the conversation. You're free to find a place and exercise their process for entering country legally. You're also welcome to leave and figure it out on your own. Regardless, whatever country you live in has rules. If its the US, you can change things with voting.

Beyond that, I see no value in the points you're making here.

I live in the U.S.

Even if I leave, if I stop using any of its infrastructure for the rest of my life, I'm expected to pay U.S. income taxes on my income. (Some, but not all, can be excluded.)

I genuinely can't get away from it.

And even if I could, you say that like there's some other place to go that doesn't impose its own taxes.

Just because every government has agreed they should ALL have the rights to take money from people who happened to be born there, it doesn't make it somehow not force.

Even if there is not a single thing I think government is uniquely qualified to do that could not be done better by private industry, government is still going to take money from me to do it its way rather than letting me come up with other ways to meet my needs, again, all based on the accident of where I was born.

It seems disingenuous to me to look at that reality and call it anything other than force.

Of course you can. You can go live in the woods and nobody will come look for taxes. Or, change countries.
My accountant calculates the cost basis for my USD/CAD exchanges in Xero. Pretty sure that’s a thing.

And if you were doing large volumes of cash exchanges as a business you’d be in trouble if you didn’t account for the cost basis.

Just pay your taxes. Really it isn't that hard. If you've maintained the asset for several years you get a tax break, there are sites out there that are designed to assist with the tracking of crypto currencies. Yes you may be able to bypass all the algorithms and systems that the US has in place to track this stuff but why? Just pay your damn taxes.
Actually it is pretty hard if you, y'know, buy stuff with a cryptocurrency, because every purchase is a taxable event! Also hard if you bought your crypto on a less well known and/or now-defunct exchange like Poloniex because the reports they generate are relatively hard to understand. My CPA couldn't understand the notation as there was no mention of USD and I had to break it down for them.

In comparison, paying taxes on stock gains is pretty easy because the brokerage generates a 1099 with all the calcs done for you.

What is this? "If you've maintained the asset for several years you get a tax break" Just capital gain?
There is both short term and long term capital gain taxes in the US. For some reason I was thinking you had to hold it for more than one year but apparently it's one. If you hold the asset for longer than a year the tax rate on it is either 0%, 15%, or 20% depending on your tax bracket
I bought bitcoins for two or three hundred bucks. Then price went a bit down, I got spooked and sold it at a loss.

So who's laughing now, IRS? Come a get me.

P.s. needless to say - sarcasm

Well, in your case you'd be able to claim that loss against the taxes you paid from other gains, right? So really, maybe the IRS owes you money. :D
It's only couple of $ so I'll let it slide this time
you laugh, but this happened to me, I reported a loss of a couple thousand bucks and now I'm petrified of an audit.
So I buy a small amount of crypto with every paycheck, and this year is the first year I had to report selling some of those transactions that had those tiny purchases as a cost basis. It's very annoying to do it manually, as you apparently are supposed to report every single one of those weeks, and calculate what portion is from which cost basis, etc. I was feeling very overwhelmed with the thought of doing it manually.

But I tried one of those bitcoin tax websites this year, and was pleasantly surprised how seamless they made it. After paying and importing my data I had the full tax forms in minutes.

Thankfully I didn't owe anything for it last year because it was a temporary panic sell during the big dip from the pandemic happened last March or April, so I basically broke even for taxes, but thankfully I came to my senses a week later and bought back in again, so I still got to fully benefit from the bull run this past year.

But yeah, it's not worth taking the risk of getting audited, imo. I still wish it weren't a taxable event just for switching which crypto you're in though, especially if it's on the same exchange, and only got taxed when you buy goods or services take it out to USD, but oh well.

> I still wish it weren't a taxable event just for switching which crypto you're in though, especially if it's on the same exchange, and only got taxed when you buy goods or services take it out to USD, but oh well.

You're describing section 1031 "like-kind" exchanges. Not available for crypto, and not available for stocks either, so it's not like crypto's getting unfair treatment here (compared to stocks). You have to do the same detailed reporting you describe for stocks.

I understand it's not available for crypto (and for stocks), I just wish that weren't the case.

Also if I have to report every single 401k purchase I ever made when I'm in my 70s when I finally cash some of it out, that's going to be a pain in the butt (I assume 401k is an exception to the rules). I basically treat my crypto purchases as another form of 401k right now (without the penalties).

With stocks, your broker just sends you a 1099 at the end of the year. It includes the cost basis of all the stock you sold that year and the date of purchase. If you sell a lot of stocks, you just get it as a CSV file and stick it into your tax software. This means paying for tax software, and probably a "higher-tier" version of it, but it's not much work.

The 401k works differently, as you noted. The money goes in pre-tax and then you pay income tax when you take it out. It's basically a way to defer your income, let it grow in the stock market, and pay taxes later. Roth IRA is a little similar--you pay income taxes before you put the money in, you let it grow, but you can take the money out tax-free (subject to conditions).

When you’re 70 you’re not going to buy a latte from your 401k. Instead you’ll transfer the money into a regular bank account (say once a month). At the end of the year you’ll get a tax form form that lists out all your 401k withdrawals.
Generally it seems the crypto tax complaints are from those who don't have any experience paying taxes from capital gains on stock sales or dividends.
if I buy and sell rubles, pounds, yen, euros, etc, do I have to pay tax on those? legit question. I've traveled a bit, but never 'exchanged' enough currency where I thought it was an issue.
The IRS wants their cut of your profits. So, if you buy $10 US worth of euros, spend half of them, the dollar tanks, and you exchange the remaining half back for $6 US, then you profited by $1 US and the IRS wants part of that one dollar.
What happens if you buy Bitcoin, it goes up, and you buy something directly with Bitcoin? Do you get taxed on those "gains?". Or only if the proceeds end up back in USD?
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Yes, the IRS expects you to pay taxes on the delta between the value of the coin when you bought it and the value of the good you exchanged it for.
Yes, you are taxed on these the same way stocks and crypto are taxed. It's called "forex" or the "foreign exchange market" and the relevant search terms to answer your question are "forex capital gains".

https://www.investopedia.com/articles/forex/09/forex-taxatio...

There are exceptions for small amounts of money used for personal reasons, I think it's $200. So if you travel to France, buy Euros, and then return to the US, and buy dollars with your leftover Euros, it won't be enough dollars to get taxed.

yeah, that's the scenario I was thinking of - even if it was more... like... a few thousand.

but today there's little reason to have too much cash for the average traveler, I'd think. I have a few Romanian lei in my wallet, but not enough to be taxable :)

Yes. I mean, if you're a professional currency trader, that's how they make their money. IRS really just cares about "income" though, doesn't really matter where it comes from: job, yard sale, crypto, selling drugs, whatever.

I'm not an expert at this, so I'm fairly curious to some similar edge cases like, what if you open an EU bank account, convert 100k USD to Euros. The Euro/USD gains a few basis points and then you buy a car. Are you taxed on the delta between when you bought the Euros and when you "sold" them? Is that any different than the (former) situation where you could buy 100k worth of bitcoin, then use the bitcoin to buy Tesla? Both are assets that appreciated vs USD. Stocks seem pretty simple, because you always have to convert back to USD, but what if you don't have to convert?

EDIT reply:...

Duh - forex - yeah - had folks in our Coworking space that were doing forex a few years back, and... I never connected that with what I was thinking. I was more thinking just... if I travel - if I buy some euros, then sell then when I get back and there's a profit (or loss) is that a taxable event? But... professional trading, yeah, seems obvious.

If they’re not “like-kind”, and if I’m not mistaken, that means at least you can do Tax-Loss Harvesting for highly correlated cryptos.
It gets even more unwieldy if you have one like Algo that pays staking rewards every day.
I've actually stopped staking for exactly this reason.

I don't have enough to stake for the rewards to be worth the time hassle of dealing with this.

I received an unsolicited airdrop which had a spot price of "$20k USD" because there was no liquidity. It's absolutely worthless.

Seems like illiquid airdrops are a good way to screw someone over in the eyes of the IRS, lol

I find it interesting how the IRS picks its targets. Facts shows the the most wealthy skip the most taxes. Yet the IRS has a hard time going after the most wealthy because they have the resources to fight it.

The more recent crop of folks that have made money in crypto don't tend to be among those ready to fight the IRS hard, they are softer targets. They are targeting the little guy on purpose.

That’s a disturbing trend in the U.S. that is getting worse as time goes on. It’s disturbingly true in criminal matters. If crime isn’t too egregious you can avoid just punishment by having the resources to tie up the DA’s office.
This is just how things work when there's so many laws and they're so broad that the scope of "prosecutable criminal behavior" exceeds enforcement resources.

Of course the DA's are gonna pick the easy wins with good optics and avoid hard targets and/or rocking the boat. That's just rational decision making.

You can either increase resources and create a police state or decrease the amount of prosecutable criminal behavior and have people complain that "there ought to be a law" about <pet issue goes here>.

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This is true, but it's philosophical. The IRS has finite resources, so it has a fundamental choice:

1. Maximize collections. This is what they're doing: spending their resources on cases with the best expected ROI. If you have $1T in net tax misses, chase the easiest 75% and expect a 90% collection rate.

2. Deter high absolute tax avoidance. This is what you're suggesting: spend their resources to make a statement, even if the ROI isn't there. If you have $1T in net tax misses, chase the hardest 25% and expect a 5% collection rate.

I don't think you're wrong, as there's value in deterrence (i.e., sue the hell out of rich tax evaders, and even if you lose, maybe the next one will be less likely to push it).

I'm really just advocating for a fair system. I have to wonder if a national sales tax isn't more fair than a national income tax - can we drastically reduce the need for collections?

Edit: really just wondering out loud, I don't have the answers here - our current system needs work

Fair for whom always needs to be discussed when talking about fairness. I personally like the sales tax idea, or even a flat tax - in the sense that everyone pays the same without all the loops holes, deductions, exemptions, that exist to gain corporate favor, buy votes, or push agendas.

The problem with both of those is it isn't fair for some, specifically folks in the lower income brackets.

I don't have all of the answers but our current system taxes labor at a higher rate than investments, which creates a 'trickle-up' effect because the most wealthy make most of their money from investments. Then enforcement tends to hurt the little guy more. There is not much fair about our current system, so lots of room for improvement.
Sales taxes are regressive. A 10% sales tax is more of a poor person's income than a wealthy person's income.

Flat tax is also funny. Because it doesn't mean getting rid of loopholes and deductions, it means taxing every dollar the same. Effectively raising the taxes on those making less. Right now we have a progressive tax rate. Where the first X dollars are taxed at A%, the next Y dollars at A+5%, and so on.

Deductions would still exist because at some point someone is going to make a good point that that money was just taxed. Or that the money went to the same goal as the tax would have. Deductions are there to find out what your taxable income is. It affects how much you owe because 10% of 900 is not the same as 10% of 1000.

High sales taxes tend to spur low-tax zones nearby. The wealthy can use these to get around taxes. For example, border runs for those who live near borders (because custom enforcement is often lax). Or doing purchases of highly expensive items in those low-tax zones and keeping them there -- such is already done now with high-value artworks and vehicles.
Sales tax is highly regressive because poor people spend most of their money staying alive, while rich people can save and reinvest their pre-tax money. You're just reinventing the current de facto regime, where rich people don't pay taxes on investments through "creative" acounting and poor people have their employer deduct their taxes from their income.

Realistically you need to have an enforcement agency with some teeth because the wealthiest people can afford to move their own money around and skirt the rules, while poor people will be transacting with third parties that have an interest in collecting and remitting taxes. The grocery store would rather be in compliance with tax law, whether it's sales tax or income tax, but your private investment office doesn't have the same incentives.

Rich people love sales taxes, since their spending is a very small percentage of their net worth.

For example, Bezos's $500M yacht might look expensive in absolute terms, but his net worth went up $74B last year. I'm sure that given the choice, he'd rather pay sales taxes than capital gains taxes.

That $74B isn't cash though, its in stock value. Jeff can hold that stock for a while and only pay long term capital gains. He can probably also make any W2 income like $1, giving him a 0% tax rate on those capital gains. Which means he'll pay more in sales tax than income tax, even under the current system.
The 0% on capital gains is nice, but as he's now single, it's only applicable for his first $40k of taxable income. So, if he can live on $40k in cap gains, and $1 of w-2, he can get off with no taxes. If he cashes in $1M in cap gains, most of that is taxed (about half at 15% and half at 20%, and most of it will also get the 3.8% net investment income tax)

I ignored deductions, including standard deduction. The point is the 0% capital gains rate isn't a magic loophole to channel billions through, it only has a small amount of room.

But you can take a dirt cheap loans due to low interest rates on your stock. The more stock value you have the cheaper interest rate you get. Therefore you don't need to sell your stock as long as it makes more than the <3% interest rate you're being charged. Even if it doesn't, it's still cheaper than paying taxes.
All of this complication is the problem. Jeff ends up getting benefits that most people don't get, at least not most younger people.

15% and/or 20% plus 3.8% is still less than the 22% to 32% range that a lot of people will fall into. And that 22-32% is on 100% of taxable income, there is no break on part of it.

Ok, but you're moving the goalposts a lot.

The government is clearly incentivising long term capital gains here. The nice thing is it's easier than ever to get into a brokerage account and buy sensible funds without paying a lot of fees. Robinhood may have started it, but fidelity and maybe others will let you buy fractional shares in etfs as long as you're putting in at least $1. Mutual funds have let you do fractional shares for a long time too, but minimums are higher and $1,000 to get into a vanguard target date fund might be too much for some people.

That is kinda the point, the current policy helps richer people, and older people that have amassed some investments, but for many and for most younger people there isn't much benefit. Why should the burden be shifted to labor? Wouldn't the investment plan work even better if everyone got the same tax break to say 15-20%? I mean people would have more to invest every year and so compounding works even better. It doesn't make sense to punish labor - its all income, why does the source matter?. Our current system shifts taxes to labor and stifles labor's ability to invest and realize gains.
The issue with a sales tax is that it taxes on consumption instead of income. Consumption needs (as opposed to wants) stop increasing somewhere at around ~100k/yr (adjust for location). A high earner is incentivized to save most of their money and become wealthy to avoid tax.

Assuming 15% sales tax, no income tax collection.

Someone who makes 100k per year and spends nearly all pays ~15k via this sales tax or 15%.

Someone who makes 500k per year and spends 100k pays ~15k via this sales tax or 3%.

Someone who makes 10mm per year and spends 1mm pays $150k via this sales tax or 1.5%.

The lower income person pays a much higher rate, because they have to.

But don't they have to spend it eventually?
You'd need to also tax gifts and inheritance at the same rate for that to work. Also, because of the time value of money, delaying tax on wealth allows you to grow it more effectively. Even if the money is eventually taxed at X%, you had years or decades for it to compound first while people who need to spend it now don't have that opportunity.
Not without an inheritance and gift tax of 100%, and not if they invest it.
Well, first, no, they don't. Gifts, inheritance, spending it via "charitable" organizations, or better yet spend in lower tax regions. We have multi-generational trust fund families.

Secondly, they can accumulate more wealth much faster than they can spend. Plus they can play with things on a longer time horizon and move internationally. Like, say once the sales tax drops.

National wealth tax on land (unimproved value only), public goods (electromagnetic spectrum, mineral drilling rights, carbon emissions), network effects (including brands, communication networks, and marketplaces), and IP (patents/copyrights/trademarks).

It's highly progressive: the average person owns zero of these things, and so would pay zero tax. It causes virtually no deadweight loss or economic distortion: the supply of these goods is heavily inelastic, in many cases totally inelastic, and so a tax will not disincentivize firms from producing more. And there's even a moral argument for it: these goods exist out there, in the natural realm, and so when somebody "owns" them it doesn't mean they created them through their own labor, it means that the government has granted them a monopoly to develop and use them, and the government should be compensated for enforcing that right.

Point 2 was the reason for the Wesley Snipes prosecution.
It's not as simple as that... The wealthy are, justly, disproportionally targeted by audits, 10x more likely to be audited if you make more than $10m vs less than $100k.

Vast ressources will not necessarily prevent you from being convicted of tax evasion cf. Charles Kushner who evaded low 5 figures in taxes while being a centimillionaire.

Do you have any proof to back up that "the rich are 10x more likely to be audited"? Not trying to call you out but I'd like to read it, that number seems extremely far fetched. My guess is everyone has a small percent chance to get audited every year (unless they find a obvious issue) and it's just a flip of a coin.

I imagine they have some kind of algorithm or MI to assist in finding discrepancies based on historical wins/loses.

I doubt it's as simple as I made 10 million, therefore I am going to get audited eventually.

It's actually the opposite as far as I know. There have been several well-researched articles in the last few years about this.

The automated flagging they use is tuned to find the common mundane violations, which tend to be by normal people with normal resources.

The tax strategies of the extremely wealthy are a good deal more sophisticated and don't lend themselves well to automated checks like these.

The mob would not miss such an opportunity!
Not a big surprise, the state doesnt want any competitors.
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Hate to be this guy all the time, but if your case is anything other than straightforward, and there are large amounts at stake, talk to a tax attorney (grain of salt: I am one).

Form websites and tutorials are all well and good, and will probably work out for more people than they don't, but you super don't want to screw up your taxes. When the bill comes due, it'll be years down the line, and for an unrecognizable sum.

Your state bar can put you in touch with one. Avoid folks marketing themselves as something like "tHe CrYpTo LaWyER."

Out of curiosity, what's your recommendation on how to differentiate a very competent tax lawyer from one that's merely good? Also, what's wrong with "crypto lawyer" people?
Domain-specific knowledge. You can't go point to point with even a marginally competent lawyer on the law (probably), but you know a lot about your issue. Can they hang? In the case of crypto, do their eyes glaze over if you refer to an altcoin? Do they use "bitcoin" and "blockchain" interchangeably? Use same process for whatever your issue is -- SaaS contracts, tech trans, etc.

The crypto lawyer folks are, by and large, claiming to be experts in a practice that is so new and so without firm guidance as to be practically the tax wild west. Right now we are in the metaphor stage, we're defining everything involved with cryptocurrency (from a tax perspective) with metaphors to other things: currency, stock, digital goods, etc. The cases that will be cited forever to define crypto for tax purposes are going to be litigated in the next few years, don't be one of them.

TLDR: Look for a tax attorney that knows the tech behind cryptocurrency well enough and doesn't make any promises or guarantees.

Edit: One additional point, merely competent attorneys won't be published in their field. If you're looking for an expert find someone who is contributing to the discussion in their area.

TL;DR: Find a good crypto lawyer
Yeah dont listen to this guy unless you want to spend 15 hours telling a licensed professional that digital assets have price charts and are extremely liquid for the needs of 99% of people and easily convertible to fiat, all while they keep deflecting to some old irrelevant headline that has nothing to do with you paying taxes on assets received and traded.

Find a lawyer that is advertising competency in this field, is willing to look at the nature of transactions instead of just assuming everything is capital gains or losses.

I’ve handheld many financial professionals on crypto topics over the last 5 years. It is a godsend that so many have moved to fill in a niche now.

None of this means anything. "Nature of the transaction" is not a thing. Like-kind exchanges no longer exist. Transacting in crypto, to buy something or to sell it, is a taxable transaction of a capital asset and results in a capital gain or capital loss.

As for the "licensed professional" dig, they're the only people who are going to represent you in front of the IRS when bad advice gets you in trouble. Do with that information what you will.

So FWIW, look out for ^ these guys too. Talk to your state or the federal bar taxation section.

This is uninspired, the nature of the transaction includes vesting schedules, 83(b) elections, 83(i) elections, donations to tax exempt organizations, and much much more. Nobody said anything about like-kind nonsense but for some reason thats the entire universe of your meta considerations.

Yeah, I’m not really responding to you at this point, everyone else that makes it this far in The thread, the point is clear: find someone inspired enough and willing enough to look at the nature of a transaction and its associated tax compliance even if they are unfamiliar with the assets used in the transaction but ideally are familiar with crypto assets being used instead of cash or securities. On this point, both of us are saying the same thing, except that the other person thinks that someone advertising domain expertise will give bad guidance. There is no way of gauging that from that assumption alone.

Lot of BS buzz words in this reply. IRS does not recognize crypto as cash. Please folks, disregard this inspired (read: bad) advice.
there wasnt a single buzz word or marketing term used.

you are obsessed with being right to attract business to your dinosaur accounting/legal firm thats losing business in a high growth sector, under the guise of better compliance and denigrating firms that you have no idea what they file

I think a lawyer without an extra computer science degree is utterly worthless in that case. Just too much technical knowledge required. Most lawyers can't tell a bit from a byte.
In your opinion, does the IRS give leniency towards people who make their best effort by either hiring a tax person, paying for software or both?

Cryptocurrency taxes are insanely awful, even if you're not talking big money. Just trying to be accurate is near impossible if you've moved your money around exchanges a few times & spent some on goods. Unless you have lots of money in Crypto it seems like trying to do honest taxes on it costs more than any money you would have made over the past few years.

IMO, not legal advice, the investigators are human beings. Good faith efforts to comply with the law will net you better results than avoidance. This is also reflected in the tax code which is replete with examples of higher fines for, say, undeclared income as against under-declared income.
As one who probably should hire an accountant more often than I do, I've underpaid the IRS a few times. Look, despite whatever image popular media might want to portray, the IRS just wants what's owed and not to anally violate you. You'll get a letter in the mail stating "here's how much you owed" (sidenote: then WTF didn't you tell me that to begin with? Could have saved both of us a lot of trouble.) You write the IRS a check, along with some extra for penalty, and you never hear from them again. My anecdata relate to stock trades, so kinda relevant to your question. Do the best you can (and really, hire an accountant), and it'll be fine.

Now, if one is blatantly practicing quasi-legal "tax avoidance" then you're on your own. But my experience, as a person who did the best they could and still screwed it up, is that the IRS is not nearly the scary monster it is made out to be.

Mostly agreed, with the exception that if you're construed to have been engaging in tax avoidance -- regardless of whether you are or not -- you'll just as soon be on your own.
This has always been my biggest fear. I don't purposely do it, but I worry that a mistake I make could be seen as large enough of a hassle to where all other parties would say you're on your own to fix & figure this out. Which could then cost a large amount of my time plus fees, which then correlates to lost revenue.
What are your thoughts on the various Crypto-tax services? For the first time in a while I'm going to have to deal with Crypto on my 2021 returns and my plan was to use on of the SaaS' out there for it. We are talking <100 (probably <40) trades max for my use-case and they seemed to be a good choice (as they import trades from major exchanges and spit out the needed IRS form) to use in addition to my normal tax preparing software.

Also, if it's not too much to ask, how should one handle crypto that they mined 6+ years ago, never declared (it was worth <$100 at the time of mining), and now want to cash out? My understanding is I was supposed to declare it as income way back then and now I would just pay capital gains (long term in my case) taxes on it. I'm happy to file some kind of an addendum but is it needed for <$100?

I have been dealing with a similar problem: Very old holdings that I first traded for back in 2013. It's unfeasible to record what I traded then since it goes through a trail of dead exchanges. I've been filing them as capital gains as I trade them now, dating their purchase time back to the year I originally traded for them(thus making them long-term), and their acquisition price as $0.

Marking acquisition price on trades to $0 is consistent with how I've seen the IRS behave in the past when I failed to report stock trades accurately($1mm volume = $1mm taxable when this occurs), and since the prices have increased 1000% in most instances(I buy and hold for years, and while I traded in 2017-2019, I did not trade at all in 2020) the initial cost is easy for me to write off.

I plan to use Cointracker's reports going forward.

This tracks. Being transparent if you're audited will be key. You're trying to keep track of things, and trying to pay what you owe based on the information you have.

Just as a heads up for other folks reading this, having a basis of $0 isn't the same as paying tax on the mined value at ordinary income rates (cap gains rate differs from ordinary income rates). Mined coins and bought coins are treated differently owing to how they're acquired.

Happy to help in general terms here.

Generally speaking, risk of audit and high fines and fees go up as the amounts you're dealing with go up. I don't know what kinds of values we're dealing with with 40-100 trades, so I'll just give you broad strokes. Having an accountant or a tax attorney review your numbers will, in almost all cases, cost you less than $1,000. If you're talking about $2,000 in income/gains, then obviously that's a non-starter and I'd just go the route you're considering (SaaS), having done good due diligence on the service as you seem to have. If, however, you're looking at $100k in OI or capital gains, I'd say a 1% investment to not owe all of your back taxes + potentially 100% or more in fines in 5-7 years when, potentially, you don't even have that money anymore.

As for your second question, I would just say there is no statute of limitations on undeclared income. The logic there is that you aren't incentivized to hide your income for 3 (or 7) years and then get off the hook, and it is difficult for the IRS or state taxing authorities to discover undeclared (as against under-declared) income -- i.e. how would they know about it? Thus, there is no amount of time that can pass such that you are truly free and clear.

You can file amended returns for ordinary income you failed to declare with Form 1040X: https://www.irs.gov/pub/irs-pdf/f1040x.pdf

Thank you for response, I really appreciate it. I’ll take a look at that form and get it filed out, I have no intention of hiding anything, I just didn’t know any better back in 2014.

As of now I’ve made zero trades but I want to pull out the max you can for long term capital gains without getting taxed by that ($40K) and I figured it’d probably spread out the cash-outs to even out the risk. I asked the person that manages my retirement fund about help with Crypto taxes and got the equivalent of a blank stare so I’ll probably need to look online for someone to hire since I don’t know how many people around me specialize in something like that.

Thank you again for your feedback.

EDIT: As shown in the replies below I misunderstood how long term capital gains were taxed. I though the brackets were based on how much you made off the trade, not based on your income. The $40K number I mention above doesn't have any significance for me in reality. If you make between $40K-$500K you pay 15% on long-term gains.

Happy to help. Best of luck, you’ve got the right approach.
> I want to pull out the max you can for long term capital gains without getting taxed by that ($40K)

Will this be your only income? If not, you'll still owe taxes. Capital gains aren't separate from the rest of your income; they're just taxed at different rates.

If this will be your only income, don't forget about the standard deduction. That gives you another $12.4K toward the 0% long-term capital gains rate, so $52.4K total.

And this is why I need to just pay someone else to handle this for me. I've read a bunch on this but I was under the (mistaken) assumption that the brackets for capital gains taxes were based on how much you made in gains (ie. up to $40K in /gains/ is taxed at 0%). Ok, well that sucks a little bit but really what that means is I'm going to get taxed at 15%, I knew 0% was too good to be true, even for long term capital gains.

EDIT: Thank you for calling that out, it will have saved me from an unpleasant surprise next April.

I highly recommend TokenTax. It's the only service that supported importing a cost basis report I already had from a different service.

Support at a few other places didn't even know what I was talking about, and didn't see the difference between uploading cost basis and simply reimporting old trades...

And I highly advise caution with TokenTax. I chose them because I had ~2k transactions on Deribit, and they promised they can digest them. They don't give out refunds specifically because their website claims they will work with you until you're satisfied.

Well, it was clear from the 5th minute they don't have "Deribit support", and I had many email exchanges with them spelling out in detail how their engine misunderstands my transactions (cost basis etc.). I gave them every opportunity to improve, and instead they eventually just ghosted me.

I understand it may be unrealistic to expect they will build this capability in three weeks. It's a shame they weren't able to level with me, and talk about the complexity of this. I ended up writing a taxable gains calculator for Deribit myself and would be happy to share it with them.

"And if Margaret pays for a car—or dinner for friends—with cryptocurrency, she likely owes tax on the transfer, much as if she paid for the car or the dinner with shares of Apple stock. The transfer is probably also taxable income to the recipient."

Does this mean crypto will never be able to compete with USD as a currency? Since it has this added tax on transfers?

This is probably a better read than WSJ - https://www.investopedia.com/tech/taxes-and-crypto/

Scroll down to personal purchases.

"Currently, tax code allows taxpayers to exclude up to $200 per transaction for foreign currency exchange rate gain, if the gain was derived from a personal purchase, like a cup of coffee. This is known as a de minimis election. But there is no “de minimis” clause that exempts small transactions, which can create a very tangled tax problem if one is constantly trading crypto and also using it to buy goods and services."

Of course keep reading & note the part where you can't deduct a loss either if you buy BTC at $60,000 & then it goes down to $50,000 because Elon Musk tweeted while you were buying a coffee or pair of jeans with your BTC.

The US government is incentivized to keep Bitcoin and others from going mainstream. Simply because removing the US dollar hegemony means the US can no longer continue to print money for deficit spending, and that sanctions would lose their teeth. I recall a TV show or movie where the Federal Reserve launched its own cryptocurrency, in which it was used for more surveillance. I could see that happening, I think the Chinese are already onto it.
The US government has nothing to fear from Bitcoin, despite grandiose conspiracy theories to the contrary.
Curious as well, especially with USDC and USDT. They are so convenient for sending arbitrarily large amounts of USD with instant settlement.
I'm glad the IRS is doing this, but I wish they would also go after wealthy people dodging taxes. The IRS has been deliberately underfunded to protect wealthy people, who have the resources to fight the IRS. Paying taxes should be celebrated, not vilified, and I hope Biden's proposal (https://www.cnbc.com/2021/05/05/bidens-80-billion-plan-to-be...) or something similar to that takes effect soon.
My random 2 cents.. It's super hard to get the very wealth $1 million plus to pay direct taxes. There are to many loop holes & they have to many opportunities available to avoid the taxes.

I think the best option is types of indirect taxes. I just don't have a great idea for this.

Despite Bitcoin being around for a decade, it's going to take computer experts, economists, and philosophers much more time to really start to understand what crypto actually is.

In my opinion, crypto is something very new in human history and most people still haven't really wrapped their minds around what it actually is. Most people are still calling it "crypto-currency" and I think that's a very bad label.

Crypto was invented as a digital currency and that's how most people conceptualize it, and the system taxes it as a security, but IMO it's better thought of as a technology platform. The biggest value of crypto isn't so much as a medium of exchange (though that's still very important) but as a distributed technology platform that enables things like smart contracts to run and the natural consequences of that like oracles.

I don't expect the current generation of politicians to understand what this means. Even a lot of very smart nerds are really just starting to understand what smart contracts can be used for and why that might be so important and the societal implications of oracles and other things like that.

To me, taxing every single crypto movement is as foolish and destructive as taxing every HTTP request would be during the formation of the Internet.

It’s not new at all. It’s the exact equivalent of tulip bulbs in the 1600s. We’ve totally seen this before.
I don't know why people keep bringing this up every time, tulip mania lasted from 1634 to 1637 (just 3 years), Bitcoin has been in existence since 2009 and it's pretty clear it's here to stay now.

Bitcoin's goal is to offer an alternative to government controlled currencies that's dependent on the whims of a few central bankers/politicians. It's not even remotely close.

As assets go up, the more people scream bubble or tulips.

As assets go down, the more people scream crash.

I've found these to be great signals of who to avoid getting investment advice from.

> I don't know why people keep bringing this up every time

The psychology of the people so dead-set against crypto is very fascinating to me, especially on a forward-thinking technology forum. You'd think that people here would be the first to recognize the potential good that comes from things like smart contracts or other unique applications of crypto.

We can't read minds of course, so this is just speculation from my own biased human perspective, but I think that people who are so virulently dead-set against crypto are IMO usually seething no-coiners who are mistakenly of the belief that they totally missed the boat on potential wealth and they're so butt-hurt about it that they want to prevent others from succeeding. Crab in a bucket mentality, so to speak.

In my opinion, what those folks would do well to understand is that we're still very early.

PS: Nothing personal against anybody is intended with the comments here, just want to comment on my opinion of peoples' general thought-processes, which is fascinating.

Bitcoin is something that was created out of thin air. There’s nothing backing it except what people believe it’s worth. There’s no inherent value.

Even baseball cards have an inherent value, ie, the cost of the paper that the card was created from. You can eat the card or you can burn it as tinder in the worst case. With a tulip bulb at least you can grow them and look at them You can also eat tulip bulbs.

With Bitcoin you literally have nothing because it’s completely virtual. So people are speculating over the value of something that is just a mathematical calculation.

Anything like that can change in a heartbeat. People can collectively decide that it has no worth and then you’re stuck with nothing. That’s what happened with tulip bulbs overnight. One week, people were buying houses with tulip bulbs and the next week they were worthless.

And yes, I know the argument behind USD and it being a fiat currency. But I don’t subscribe to it because it has critical mass.

We have seen the same thing over and over again in history with stuff like Bitcoin. Dotcom bust, housing bust, etc. I don’t believe Bitcoin will be anything different.

When Bitcoin is actively being used as a currency and not speculation then that’s when I will change my mind. Until then it’s a fad that will eventually go to zero. I believe the US government and other governments around the world will ban its use and use terrorism and money laundering as the key reason. It will go to zero soon afterwards in my opinion.

> There’s no inherent value.

I don't see this as a good argument because all value is subjective. Value is not a property of nature that can be measured by an objective measure: it's a subjective assessment. There's no inherent value to anything, whether fiat, crypto, or even precious metals: it's all subjective. If you're defining inherent value as functionality, crypto has significant utility through its mostly unique attributes, such as being permissionless, trustless, and borderless, among others. Without anybody's permission, I can send crypto anywhere in minutes (or even seconds, depending on the tech chosen). As useful as fiat and gold can be, try doing that with anything other than crypto.

> People can collectively decide that it has no worth and then you’re stuck with nothing.

Of course nobody knows the future and literally anything can happen. Who would have thought that in CURRENT_YEAR there'd be a series of events taking place that would make you a criminal to enter a bank WITHOUT wearing a mask. Maybe Elon Musk can figure out how to mine asteroids and gold/silver might drop in value to near zero. Or maybe the dollar might inflate its way to oblivion (IMO heading that way) like many fiat currencies have done before. Of course, crypto might significantly drop in popularity too...who knows....but I think there's enough people out there that want a medium of exchange that cannot be inflated. If you're not yet angry about your savings being reduced to print ~infinite money, you will be soon. Bitcoin, as one example, is an asset that cannot be inflated: until the end of time, there can only ever be 21 million of them.

> We have seen the same thing over and over again in history with stuff like Bitcoin. Dotcom bust, housing bust, etc. I don’t believe Bitcoin will be anything different.

You can believe this, but IMO this is a bad argument and a fundamental misunderstanding of what the business cycle is caused by...this is a property of fiat, not crypto. When the government's national bank inflates the money supply by increasing the supply of currency, it reduces the rate of interest and can increase the price of some assets. This malinvestment is the boom and bust cycle we've seen in many other assets. Unless you're talking about some specific crypto that doesn't have a maximum number of units of account, this is impossible through crypto.

> When Bitcoin is actively being used as a currency and not speculation then that’s when I will change my mind.

I'm literally scratching my head because Bitcoin has been used to exchange goods and services for years now.

> It will go to zero soon afterwards in my opinion.

Cool beans. This is not financial advice, but if you want to make money on your hypothesis, you can short Bitcoin and make an absolute killing if you really believe that.

To be used as a currency for the virtual borderless world, it needs to be worth at least a few trillion dollars, anything less than that would be too small to power any sizeable economy (especially one that's borderless and worldwide).

Do you expect it to be worth that much on day 1? No! It will grow to that level. And what happens between the 0$ value and trillions? It acts as a store of value with a great upside. Once it gets closer to it's real value, it starts to act as a means of exchange and currency.

Just because something is virtual doesn't mean it doesn't have any value. There's lots of virtual things that people value highly.

They can ban it all they want, they can't stop it, that's the whole point of the exercise.

> but I think that people who are so virulently dead-set against crypto are IMO usually seething no-coiners who are mistakenly of the belief that they totally missed the boat on potential wealth

That certainly is one reason and probably the main one, but I guess there is also the activist types where they feel so strongly against something that they spew vitriol against the great demon that is destroying humanity in some way. They just happened to latch on to crypto.

Tulip bulbs aren't programmable.
> Tulip bulbs aren't programmable.

But they're prettier to look at (or at least the tulips you grow from them are). Especially the mania ones, which had some kind of disease that made them brilliantly multicolored.

Isn't this just a better reason to switch to decentralized anonymous exchanges like Bisq or used anonymized transaction technologies like ring signatures and zero knowledge proofs (Monero/ZChash)?

I've used Coinbase so far to learn about crypto, and I fully intend on paying all taxes owed, but Bisq seems like the next best on-ramp if it can help avoid the headache of treating crypto transactions like stocks rather than currencies.

Of course I understand the sentiment that people should pay their taxes to society, but I wonder if this is not just going to result in an escalating arms race. This was prevented with dollars since most dollars earned by the populace can be traced back to a paystub, but once you've earned crypto in an anonymous transaction, it seems like a losing battle to try and tax any aspect of that.

I can't help but feel the IRS would be better served by taxing at the off-ramp like a sales tax at a POS rather than trying to fold this into an existing income tax structure. A government can kind of control a brick and mortar retailer or Amazon more so than an individual person who say sold a book direct to consuers for Monero or sold their car for ZCash.

Is the federal government prevented from creating a national sales tax for some reason?

Property you pay sales tax on is still another taxable event if you sell it for more than you paid. Sales tax does not remove the requirement to report income.
It’s not a reason to, but it might be a motivation. Unfortunately the technology is well ahead of the law, which is the perfect storm for punishing honesty. The US is well ahead of the rest of the world in enforcement. But also unfortunately, this means that the costs and risks of participation in this new financial system is massively greater for US citizens.

There is some international pressure for other countries to tax crypto trades instead of just fiat gains. Indonesia and Korea are considering it. France has clarified that they will not. Switzerland doesn’t tax capital gains at all. The differences between countries will unfortunately have consequences for which economies and citizens lead or get left behind - unless it’s all bollocks and national fiat with dollar reserve is the future.

I used bitcoin.tax way back in 2018 and it was pretty smooth filing crypto related transactions