How converted stock is taxed due to an acquisition
"I don't think its a taxable event since no income has been constructively received (talking about the RSU shareholders here). I believe you're right with the IRC 1033, and the basis of the RSU is the basis of the original stock option (probably zero). Edit: see below. However, once the stock becomes vested - then it is a taxable event (not when the cash is received, but when the chance of forfeiture diminishes, even if the employee doesn't sell the stock), and is an ordinary income, not capital. That is my understanding of the situation, do not consider it as a tax advice in any way. I gave it a bit more though and I don't think IRC 1033 is relevant. You're not doing any exchange or conversion here, because you didn't have anything to convert to begin with, and don't have anything after the ""conversion"". Your ISO's are forfeited and no longer available, basically - you treat them as you've never had them. What happened is that you've received RSU's, and you treat them as a regular RSU grant, based on its vesting schedule. The tax consequences are exactly as I described in my original response: you recognize ordinary income on the vested stocks, as they vest. Your basis is zero (i.e.: the whole FMV of the stock at the time of vesting is your ordinary income). It should also be reflected in your W2 accordingly."
"If the owner of the stock wants it back, they ""call"" it back. There are no guarantees of how long you can keep it for your short, or the cost involved to hold it.  Usually, everyone knows about a particular set-up (e.g. a warrant or convertible bond mispricing) that is attractive for arbitrage. This causes the associated stock to be in high demand thus expensive to borrow for shorting, or impossible to find for any price at all." Based on my research, the answer is both. You would pay taxes on the bitcoin you mine as income, and then capital gains tax when you sell them for a profit (or capital loss if you lose value on the sale).  You can write off a portion of your electricity bill and hardware purchased for the use of mining as a business expense, but it's recommended that you consult a tax professional for determining the proper amount that is eligible for a deduction.  From Forbes: New Bitcoin are being issued by the system roughly every 10 minutes by   a process called mining. In mining, computers running the Bitcoin   software around the world attempt to solve math problems and the first   computer to come up with the solution adds the most recent   transactions to the ledger of all Bitcoin transactions, plus receives   the new bitcoins created by the system, called the block reward. If you are a miner and win the block reward, you must record the fair   market value of Bitcoin that day and mark that as an addition to your   personal or business income. Also note the date and timestamp at which   your coins were mined. Later, when you dispose of those Bitcoin, you   will subtract the date of acquisition from the date of disposal, and   you will be taxed a long-term capital gains rate on any Bitcoin you   held for more than a year, and a short-term capital gains rate on any   Bitcoin you held for a year or less. (The timestamp isn’t absolutely   necessary, but is helpful to validate the order of multiple   acquisitions or disposals within a day.) The amount you pay in taxes on a long-term capital gain will depend on   your income-tax bracket, while short-term capital gains are taxed the   same as ordinary income. From bitcoin.tax:  Another clarification in the IRS's March notice was how mining should   be treated. Mining is income, on the day of receipt of any coins and   at the fair value of those coins. This means that if you mined any   Bitcoins or alt-coins either solo, as part of a pool, or through a   cloud provider, you need to report any coins you received as income. Where it is less clear, is what that dollar value might be, since the   fair value is not always as easy to determine.  Bitcoins, Litecoins,   Dogecoins, are all examples of where there is a direct USD market and   so you can easily find out their value of any given day. However, a   newly created alt-coin that was mined in its early days has no direct   market and so how do you determine its value? Or for any alt-coin,   e.g. ABC coin, that has no direct USD market but does have a BTC   market. Does it have a value? Do you have to make a conversion from   ABC to BTC to USD?  Since there is no clarification yet from the IRS on   this issue you should discuss how to proceed with your own tax   professional. BitcoinTaxes has taken a prudent approach and calculates   value where a fiat or BTC market exists, converting an alt-coin to BTC   to USD as necessary. And from Bitcoin magazine: The IRS also stated mined bitcoins are treated as immediate income at   the market value of those mined coins on their date of mining. “Most don’t know they can write off any losses they have,” said Libra   founder Jake Benson. “The IRS allows you to offset income by up to   $3,000 per year on capital losses.  If you have losses and you aren’t   writing them off, then it’s like throwing money away. Nobody likes   doing taxes, but if you can owe less or increase your return, then   doing your Bitcoin taxes often results in a benefit. In fact, the   majority of our users are filing a capital loss, which means they’ve   actually saved money by using our tool.”  Benson also gives insight for miners.  “Mining is considered income, so know the price of Bitcoin at the time   you mined it,” he said. “If you make money on Bitcoin trading, the IRS   requires that you report gains with line level detail.”  The   appropriate form for that is 8949, a sub-form of schedule D. Gains and   losses, as outlined above, are treated like every other capital asset. In this type of strategy profit is made when the shares go down as your main position is the short trade of the common stock. The convertible instruments will tend to move in about the same direction as the underlying (what it can be converted to) but less violently as they are traded less (lower volatility and lower volume in the market on both sides), however, they are not being used to make a profit so much as to hedge against the stock going up. Since both the bonds and the preference shares are higher on the list to be repaid if the company declares bankruptcy and the bonds pay out a fixed amount of interest as well, both also help protect against problems that may occur with a long position in the common stock.  Essentially the plan with this strategy is to earn fixed income on the bonds whilst the stock price drops and then to sell both the bonds and buy the stock back on the market to cover the short position. If the prediction that the stock will fall is wrong then you are still earning fixed income on the debt and are able to convert it into stock at the higher price to cover the short sale eliminating, or reducing, the loss made on the short sale. Effectively the profit here is made on the spread between the price of the bond, accounting for the conversion price, and the price of the stock and that fixed income is less volatile (except usually in the junk market) than stock. For various reasons, if you can defer tax payment, it's good for you [when you can give uncle sam $x tomorrow, why give it today?]. Some reasons are, you may plan to return back to your country after x years and then you can pay tax at a lower bracket [e.g. convert 401k to Rollover-IRA then do Roth-conversion and pay lower tax bracket]. Paying now versus later is purely based on your anticipated future tax bracket. [if future bracket is same.. say 25% today and after say 20 years, 25%.. there is absolutely no difference between today payment or future payment of tax -- you can mathematically prove the returns are the same for Roth-IRA (or Roth-401k) versus IRA (or 401k)]. Having a bigger balance (in case of 401k compared to roth-401k) can also give you a sense of more security -- since there are provisions for hardship withdrawal (tax may be due) "Very interesting question. While searching i also found that some precious metal ETFs (including IAU) gains are taxed at 28% because IRS considers it ""collectible"", rather than the usual long term 15% for stocks and stock holding ETFs. As for capital gain tax you have to pay now my guess it's because of the following statement in the IAU prospectus (page 34): When the trust sells gold, for example   to pay expenses, a Shareholder will   recognize gain or loss ...." If you are tax-resident in the US, then you must report income from sources within and without the United States.  Your foreign income generally must be reported to the IRS.  You will generally be eligible for a credit for foreign income taxes paid, via Form 1116. The question of the stock transfer is more complicated, but revolves around the beneficial owner.  If the stocks are yours but held by your brother, it is possible that you are the beneficial owner and you will have to report any income. There is no tax for bringing the money into the US.  As a US tax resident, you are already subject to income tax on the gain from the sale in India.  However, if the investment is held by a separate entity in India, which is not a US domestic entity or tax resident, then there is a separate analysis.  Paying a dividend to you of the sale proceeds (or part of the proceeds) would be taxable.  Your sale of the entity containing the investments would be taxable.  There are look-through provisions if the entity is insufficiently foreign (de facto US, such as a Subpart-F CFC).  There are ways to structure that transaction that are not taxable, such as making it a bona fide loan (which is enforceable and you must pay back on reasonable terms).  But if you are holding property directly, not through a foreign separate entity, then the sale triggers US tax; the transfer into the US is not meaningful for your taxes, except for reporting foreign accounts. Please review Publication 519 for general information on taxation of resident aliens. "I was told by the lawyers there was no tax consequence because the two   numbers were the same. That is correct. However, a tax professional tells me that since the start-up stock was   ""realized"" there invokes a taxable event now. That is correct. I'm now led to believe I owe cap-gains tax on the entire 4 year vest   this year That is incorrect. You owe capital gains tax on the sale of your startup stock. Which is accidentally the exact same amount you ""paid"" for the new unvested stocks. There's no taxable event with regards to the new stocks because the amount you paid for them was the amount you got for the old stocks. But you did sell the old stocks, and that is a taxable event." Sale of a stock creates a capital gain. It can be offset with losses, up to $3000 more than the gains. It can be deferred when held within a retirement account.  When you gift appreciated stock, the basis follows. So when I gifted my daughter's trust shares, there was still tax due upon sale. The kiddy tax helped reduce but not eliminate it. And there was no quotes around ownership. The money is gone, her account is for college.  No 1031 exchange exists for stock.