Can expenses for attending stockholders meetings be deducted in U.S. income taxes?
"Nope, not deductible. It's true that some investment expenses are deductible, mainly as ""miscellaneous itemized expenses"", though only the amount that exceeds 2% of your adjusted gross income.  But as explained in IRS Pub 550, which lays out the relevant rules: Stockholders' meetings.   You cannot deduct transportation and other expenses you pay to attend stockholders' meetings of companies in which you have no interest other than owning stock. This is true even if your purpose in attending is to get information that would be useful in making further investments."
Basically a company who provides health insurance for their employees provides it as part of the employee's salary package. This is an expense by the company in its pursuit of making income. In general, tax deductions are available on any expense incurred in deriving income (the exception is when social policy allows deductions for other types of expenses). If you pay for your own health insurance individually, then this expense is not an expense for you to derive your income, and as such is not tax deductible. "Be careful of the other answers here. Many are wrong or partially wrong. The question implies that you knew this, but for everyone else's benefit, you can keep you LLC organization and still elect to be treated as a S-Corp by the IRS just for tax purposes.  You do this by filing Form 2553 with the IRS. (You can also, by the way, elect to be taxed as a ""regular"" C-Corp if you want, although that's probably not advantageous.  See Form 8832.) The advantage of electing to be treated as an S-Corp is that income beyond what constitutes a ""reasonable salary"" are not subject to social security and medicare taxes as they would when paid was wages or counted as self-employment income on Schedule C.  Depending on what you need to pay yourself to meet the ""reasonable salary"" test, your overall income, and other factors about your business, this could result in tax savings. Contrary to other answers here, making this election will not force you to create a board of directors.  You are still an LLC for all purposes except taxes, so whatever requirements you had in organization and governance at the state level will not change.  You will have to file a ""corporate"" tax return on Form 1120S (and likely some corresponding state tax form), so that is additional paperwork, but this ""corporate"" return does not mean the S-Corp pays taxes itself. With a couple of exceptions, the S-Corp pays no taxes directly (and therefore does not pay at the corporate tax rate). Instead the S-Corp apportions its income, expenses, and deductions to the owner(s) on Schedule K.  The owners get their portion reported from the S-Corp on Schedule K1 and then include that on their personal Form 1040 to pay tax at their personal rate. In addition to filing Form 1120S, you will have to handle payroll taxes, which will create some additional administrative work and/or cost. Using a payroll service for this will likely be your best option and not terribly expensive. You've also got the issue of determining your reasonable salary within the rules, which is the subject of other questions on this site and other IRS guidance." The thing you get wrong is that you think the LLC doesn't pay taxes on gains when it sells assets.  It does. In fact, in many countries LLC are considered separate entities for tax properties and you have double taxation - the LLC pays its own taxes, and then when you withdraw the money from the LLC to your own account (i.e.: take dividends) - you pay income tax on the withdrawal again. Corporate entities usually do not have preferential tax treatment for investments. In the US, LLC is a pass-though entity (unless explicitly chosen to be taxed as a corporation, and then the above scenario happens). Pass-through entities (LLCs and partnerships) don't pay taxes, but instead report the gains to the owners, which then pay taxes as if the transaction was their personal one. So if you're in the US - investing under LLC would have no effect whatsoever on your taxes, or adverse effect if you chose to treat it as a corporation. In any case, investing in stocks is not a deductible expense, and as such doesn't reduce profits. If the brokerage account holds US assets, such as the stock of US companies, then it may be taxable under some conditions. The rules are complex and depend on the nationality of the individuals, because the results may be affected by tax treaties between the United States and whatever country the person is from. Both US GAAP and IFRS are accrual basis frameworks. 99.9% of businesses report under those frameworks (or their local gaaps, but still accrual based). Usually it's public sector entities which are cash-basis in my experience.   Anyway, accrual basis has more to do with revenue recognition, not taxation, so that's not really relevant here. The value date of an invoice (ie in which moment it becomes taxable) depends on tax legislation (which sets the rules to determine the so called date of taxable event), not so much on accounting principles.   In many cases taxable rules are intertwined with cash collection/payment, however, to prevent creative accounting for tax evasion purposes. For example, provisions for various uncertain future events might be required by accounting rules, but the corresponding expenses are generally not deductible for tax purposes (so you won't be able to deduct them until the event actually occurs and you pay). All corporate gains are taxed at the same rate as corporate income, for the corporate entity, so this actually can be WORSE than the individual capital gains tax rates. There are a lot of things you can do with trading certain asset classes, like opening you up to like-kind re-investment tax perks, but I can't think of anything that helps with stocks. Also, in the US there is now a law against doing things solely to avoid tax if they have no other economic purpose. So be conscious about that, you'll need to be able to rationalize at least a thin excuse for why you jumped through all the hoops. "That's a tricky question and you should consult a tax professional that specializes on taxation of non-resident aliens and foreign expats. You should also consider the provisions of the tax treaty, if your country has one with the US. I would suggest you not to seek a ""free advice"" on internet forums, as the costs of making a mistake may be hefty. Generally, sales of stocks is not considered trade or business effectively connected to the US if that's your only activity. However, being this ESPP stock may make it connected to providing personal services, which makes it effectively connected. I'm assuming that since you're filing 1040NR, taxes were withheld by the broker, which means the broker considered this effectively connected income." Yes and no. This really should be taught at junior school level in a capitalist country but that is a different argument. A company is influenced by its shareholders but not in the way you are hoping. This is the only area where a Company must behave democratically with one share one vote. If you own one share in a company (specifically a voting share), then you are entitled to attend an AGM where you will have a vote on issues presented by the board. You might have an opportunity to make a statement or ask a question at the AGM, but I wouldn't rely on it. You will not be able to influence the companies behavior beyond that unless you control enough shares to influence the board. Notice I said 'control' not 'own'. If you get other shareholders to agree to vote with you, then you effectively control their shares. Shareholders are there to get a return on their investment, so you must convince them that they will get a better return by agreeing with you then by following the board (that they put there!). Convince them that (for example) a trespass lawsuit will rob the company of more value then the profit to be made and they might agree to not trespass. Morals, ethics, justice etc., are human attributes and since most shareholders are other corporations not humans, they have no place in your arguments with one exception; Goodwill is a value that appears on a balance sheet and you might be able to use emotional arguments to show that there is a risk of a loss of goodwill from the proposed actions. You can make your argument stronger by generating media pressure on customers and suppliers of the company to make critical public comments. "This information is clearly ""material"" (large impact) and ""non-public"" according to the statement of the problem.  Also, decisions like United States v. Carpenter make it clear that you do not need to be a member of the company to do illegal insider trading on its stock. Importantly though, stackexchange is not a place for legal advice and this answer should not be construed as such.  Legal/compliance at Company A would be a good place to start asking questions." Here's the best explanation I found relating to why your T4 box 39 might not have an amount filled in, even when box 38 has one: Department of Finance – Explanatory Notes Relating to the Income Tax Act [...]. It's a long document, but here's the part I believe relevant, with my emphasis: Employee Stock Options ITA 110(1)   [...]   Paragraph 110(1)(d) is amended to include a requirement that the   employee [...] exercise the employee’s rights under the stock   option agreement and acquire the securities underlying the agreement   in order for the deduction in computing taxable income to be   available [...] ensures that   only one deduction is available in respect of an employment benefit. In other words, if employee stock option rights are surrendered to an   employer for cash or an in-kind payment, then (subject to new   subsections 110(1.1) and (1.2)) the employer may deduct the payment   but the employee cannot claim the stock option deduction. Conversely,   where an employer issues securities pursuant to an employee’s exercise   of stock options, the employer can not deduct an amount in respect of   the issuance, but the employee may be eligible to claim a deduction   under paragraph 110(1)(d). Did you receive real shares based on your participation in the ESPP, or did you get a cash payment for the net value of shares you would have been issued under the plan? From what I can tell, if you opted for a cash payment (or if your plan only allows for such), then the part I emphasized comes into play. Essentially, if conditions were such that your employer could claim a deduction on their corporate income tax return for the compensation paid to you as part of the plan, then you are not also able to claim a similar deduction on your personal income tax return. The money received in that manner is effectively taxed in your hands the same as any bonus employment income would be; i.e. it isn't afforded tax treatment equivalent to capital gains income. Your employer and/or ESPP administrator are best able to confirm the conditions which led to no amount in your box 39, but at least based on above you can see there are legitimate cases where box 38 would have an amount while box 39 doesn't. Assuming the US, if a human assessor audited you, could you show a future profit motive or will they conclude you are expensing a hobby? If you answer yes, you are likely to only be deducting limited expenses this year, carrying forward losses to your profitable years.  See the examples in pub 535: http://www.irs.gov/publications/p535/ch01.html#en_US_2014_publink1000208633 You can only deduct (with the 2% AGI threshold) expenses that: You've actually incurred. I.e.: you actually paid for equipment or services provided and can show receipts for the payment. At the request of the employer. I.e.: you didn't just decide on your own to buy a new book or take a class, your employer told you to. With business necessity. I.e.: it was in order for you to do your job. And you were not reimbursed by your employer. I.e.: you went somewhere and spent your after tax money on something employer explicitly told you to pay for, and you didn't get reimbursed for that. From your story - these conditions don't hold for you. As I said in the comments - I strongly suggest you talk to a lawyer. Your story just doesn't make any sense, and I suspect your employer is doing something very fishy here. This answer fills in some of the details you are unsure about, since I'm further along than you. I bought the ESPP shares in 2012.  I didn't sell immediately, but in 2015, so I qualify for the long-term capital gains rate. Here's how it was reported: The 15% discount was reported on a W2 as  it was also mentioned twice in the info box (not all of my W2's come with one of these) but also  This showed the sale trade, with my cost basis as the discounted price of $5000. And for interests sake, I also got the following in 2012: WARNING! This means that just going ahead and entering the numbers means you will be taxed twice! once as income and once as capital gains. I only noticed this was happening because I no longer worked for the company, so this W2 only had this one item on it. This is another example of the US tax system baffling me with its blend of obsessive compulsive need for documentation coupled with inexplicably missing information that's critical to sensible accounting. The 1099 documents must (says the IRS since 2015) show the basis value as the award price (your discounted price).   So reading the form 8949: Note: If you checked Box D above but the basis reported to the IRS was   incorrect, enter in column (e) the basis as reported to the IRS, and   enter an adjustment in column (g) to correct the basis. We discover the number is incorrect and must adjust.  The actual value you need to adjust it by may be reported on your 1099, but also may not (I have examples of both). I calculated the required adjustment by looking at the W2, as detailed above. I gleaned this information from the following documents provided by my stock management company (you should the tax resources section of your provider): If you just make a capital contribution to the company it is not a taxable event.  If you're the owner, lending only makes sense if you want the company to pay you interest (if you have partners who aren't lending money, for example) and you want to be compensated for lending, a loan would allow that. But the interest is taxable as income to you (1099-int) and the company can expense it. But a capital contribution is much easier and you can take a distribution later to get paid back. Neither event is taxed, but you cannot take interest. I can make that election to pay taxes now (even though they aren't vested) based on the dollar value at the time they are granted? That is correct. You must file the election with the IRS within 30 days after the grant (and then attach a copy to that year's tax return). would I not pay any taxes on the gains because I already claimed them as income? No, you claim income based on the grant value, the gains after that are your taxable capital gains. The difference is that if you don't use 83(b) election - that would not be capital gains, but rather ordinary salary income. what happens if I quit / get terminated after paying taxes on un-vested shares? Do I lose those taxes, or do I get it back in a refund next year? Or would it be a deduction next year? You lose these taxes. That's the risk you're taking. Generally 83(b) election is not very useful for RSUs of established public companies. You take a large risk of forfeited taxes to save the difference between capital gains and ordinary gains, which is not all that much. It is very useful when you're in a startup with valuations growing rapidly but stocks not yet publicly trading, which means that if you pay tax on vest you'll pay much more and won't have stocks to sell to cover for that, while the amounts you put at risk are relatively small.