Do I need a Like-Kind Exchange when selling a personal vehicle for a company car
You cannot do a like-kind (Sec. 1031) exchange for personal property, only for business/investment property. Since you said that you traded in your personal car - no like-kind exchange is possible. Also, since the new car doesn't belong to you - you didn't actually perform any exchange. You sold your old car, but you didn't buy a new one. If Turbo-Tax suggests you to fill the exchange form - you must have entered something wrong to make it think there was an exchange. Check your entries again, specifically - check if you entered that you purchased a new car instead of the old one, since you didn't. See an example of where to start looking here.
If you are exchanging money for travel then you should not have to pay any capital gains on any exchange that is in your favour. Exchanging currency for travel is different from trading currencies for an attempt at making profits. NEVER combine the negotiations for trade-in of an old car and purchase of a new one (and/or financing), if you can avoid doing so. Dealers are very good at trading off one against the other to increase their total profit, and it's harder for you to walk away when you have to discard the whole thing. These are separate transactions, each of which can be done with other parties.  Treat them as such. Sounds like 'up-selling'.    You can harden yourself into being a 'tough sell' but it takes time and a lot of shopping.     The quickest way to put up a defense is to never ever make a purchase over $100 without 'sleeping on it'.  Just walk away, tell them you'll think it over, and go do some more research.   Don't go back into a dealership or store that has hit you with guilt or pressure or a crazy price or whatever.   Find a no-haggle or no-frills source, or even a source to buy a used version of the item you want. Since I'm missing the shortest and simplest answer, I'll add it: A car also doesn't offer dividends, yet it's still worth money. A $100 bill doesn't offer dividends, yet people are willing to offer services, or goods, or other currencies, to own that $100 bill. It's the same with a stock. If other people are willing to buy it off you for a price X, it's worth at least close to price X to you. In theory the price X depends on the value of the assets of the company, including unknown values like expected future profits or losses. Speaking from experience as a trader, in practice it's very often really just price X because others pay price X. "The question is about the dealer, right?  The dealer isn't providing this financing to you, Alfa is, and they're paying the dealer that same ""On the Road"" price when you finance the purchase.  So the dealer gets the same amount either way. The financing, through Alfa, means your payments go to Alfa.  And they're willing to give you 3,000 towards purchase of the car at the dealer in order to motivate those who can afford payments but not full cash for the car.  They end up selling more cars this way, keeping the factories busy and employees and stockholders happy along the way.  At least, that's how it's supposed to work out." The best way to do this is to pay for the entire car, including gas, insurance, and repairs, from S-corp funds, then meticulously track how many miles are used for personal and how many miles for business. If you pay with S-corp funds, you will claim the personal miles as a taxable benefit from the S-corp on your personal return. The S-corp can then claim all the expenses and depreciation on the vehicle, reducing the S-corp's tax liability. It looks like JP Morgan can convert your holding to unsponsored ADRs until July.. In any event, you should not completely lose the equity. Volvo still exists as a public company, it's just not tradable on US exchanges. Q1: Yes, you'd need a JPM account.  Your broker should have offered a similar service. If they didn't they are not a broker. Q2: You own 30 shares in Volvo. You need to get your broker to either sell them (off-exchange now) or tell you how to gain access to them. That is a desirable model so I doubt you could get it into the low 30's. Also you mentioned you want it optioned out. That would also reduce the leverage you have in the negotiation. Look at True Car to find out what you'd actually be paying. You will either get the car you want or the price you want. Yes, but then either of you will need the other's permission to sell the car. I strongly recommend you get an agreement on that point, in writing, and possibly reviewed by a lawyer, before entering into this kind of relationship. (See past discussions of car titles and loan cosigners for some examples of how and why this can go wrong.) When doung business with friends, treating it as a serious business transaction is the best way to avoid ruining the friendship. "I'm going to ignore your numbers to avoid spending the time to understand them.  I'm just going to go over the basic moving parts of trading an upside down car against another financed car because I think you're conflating price and value.  I'm also going to ignore taxes, and fees, and depreciation. The car has an acquisition cost (price) then it has a value.  You pay the price to obtain this thing, then in the future it is worth what someone else will pay you. When you finance a car you agree to your $10,000 price, then you call up Mr. Bank and agree to pay 10% per year for 5 years on that $10,000.  Mr. Banker wires over $10,000 and you drive home in your car.   Say in a year you want a different car.  This new car has a price of $20,000, and wouldn't you know it they'll even buy your current car from you.  They'll give you $7,000 to trade in your current car. Your current car has a value of $7,000.  You've made 12 payments of $188.71.  Of those payments about $460 was interest, you now owe about $8,195 to Mr. Banker. The new dealership needs to send payment to Mr. Banker to get the title for your current car.  They'll send the $7,000 they agreed to pay for your car.  Then they'll loan you the additional $1,195 ($8,195 owed on the car minus $7,000 trade in value).   Your loan on the new car will be for $21,195, $20,000 for the new car and $1,195 for the amount you still owed on the old car after the dealership paid you $7,000 for your old car. It doesn't matter what your down-payment was on the old car, it doesn't matter what your payment was before, it doesn't matter what you bought your old car for.  All that matters is how much you owe on it today and how much the buyer (the dealership) is willing to pay you for it. How much of this is ""loss"" is an extremely vague number to derive primarily because your utility of the car has a value.  But it could be argued that the $1,195 added on to your new car loan to pay for the old car is lost." "In the US you are not required to have a corporation to use business expenses to offset your income. The technical term you need is ""deducting business expenses"", and in matters of taxes it's usually best to go straight to the horse's mouth: the IRS's explanations Deducting Business Expenses  Business expenses are the cost of carrying   on a trade or business. These expenses are usually deductible if the   business operates to make a profit.  What Can I Deduct? Cost of Goods   Sold, Capital Expenses, Personal versus Business Expenses, Business Use   of Your Home, Business Use of Your Car, Other Types of Business Expenses None of this requires any special incorporation or tax arrangements, and are a normal part of operating a business.  However, there is a bit of a problem with your scenario. You said you ""invested"" into a business, but you mentioned buying specific things for the business which is not generally how one accounts for investment. If you are not an owner/operator of the business, then the scenario is not so straight-forward, as you can't simply claim someone else's business expenses as your own because you invested in it. Investments are taxed differently than expenses, and based upon your word choices I'm concerned that you could be getting yourself into a bit of a pickle. I would strongly advise you to speak with a professional, such as a Certified Public Accountant (CPA), to go over your current arrangement and advise you on how you should be structuring your ongoing investment into this shared business. If you are investing you should be receiving equity to reflect your ownership (or stock in the company, etc), and investments of this sort generally cannot be deducted as an expense on your taxes - it's just an investment, the same as buying stock or CDs. If you are just buying things for someone else's benefit, it's possible that this could be looked upon as a personal gift, and you may be in a precarious legal position as well (where the money is, indeed, just a gift). And gifts of this sort aren't deductible, either.  Depending on how this is all structured, it's possible that you should both consider a different form of legal organization, such as a formal corporation or at least an official business partnership. A CPA and an appropriate business attorney should be able to advise you for a nominal (few hundred dollars, at most) fee. If a new legal structure is advisable, you can potentially do the work yourself for a few hundred dollars, or pay to have it done (especially if the situation is more complex) for a few hundred to a few thousand. That's a lot less than you'd be on the hook for if this business is being accounted for improperly, or if either of your tax returns are being reported improperly!" I don't believe you can do that. From the IRS: Finally, certain types of property are specifically excluded from Section 1031 treatment. Section 1031 does not apply to exchanges of: I highlighted the relevant items for emphasis. Check the employee-friends-and-family sales contract, which your friend should be able to get quite easily. There is almost always a minimum holding period before resale clause, specifically to prevent this kind of scenario. Without that clause, the dealers tend to riot... Also, remember that a car loses a huge percentage of its value the moment it leaves the lot. Odds are that you'd be doing well to find someone willing to buy it from you at the discounted price. If you don't want this car, ask your friend not to buy it and get one you do want. Seriously. "Yes, you can do that, but you have to have the stocks issued in your name (stocks that you're holding through your broker are issued in ""street name"" to your broker). If you have a physical stock certificate issued in your name - you just endorse it like you would endorse a check and transfer the ownership. If the stocks don't physically exist - you let the stock registrar know that the ownership has been transferred to someone else. As to the price - the company doesn't care much about the price of private sales, but the taxing agency will. In the US, for example, you report such a transaction as either a gift (IRS form 709), if the transaction was at a price significantly lower than the FMV (or significantly higher, on the other end), or a sale (IRS form 1040, schedule D) if the transaction was at FMV." So I want to sell my 100 shares of AAPL to him at a price of 10 or   even 1 US Dollar. Is that legal/allowed? Of course. It's your stocks - do with it what you want. if the two persons are not served by a same broker. You'll have to talk to your broker about the technicalities of the transaction. if the person who sell are US citizen and the person who buy are not, and and vice-versa Since you asked specifically about US citizenship, I'll assume you're in the US or the transaction is taking place in the US. Citizenship has nothing to do with it (except may be for economic sanctions against Russians or Iranians that may come into play). What is important is the tax residency status. Such a transfer is essentially a gift, and if you're a US tax resident (which doesn't correlate to your immigration status necessarily) - you'll have to deal with the gift tax consequences on the discount value. For example - you have 100 shares of AAPL which you sold to your friend for $1 each when the fair market value (FMV) was $501. So essentially, the friend got $50,100 value for $100. I.e.: $50K gift. Since this amount is above the annual $14K exemption - you'll have to deal with the gift tax and file gift tax return. There are also consequences for the capital gains tax for both you and your friend. I suggest you talk to a licensed tax adviser (EA/CPA licensed in your State) about the specifics given your circumstances. If you (or the recipient) are also a foreign citizen/tax resident - then that country's laws also may affect your situation.