100% Ownership and 30% profit to sale director
Perhaps an example will help make it more clear. Any given year:  Revenue:  200K, profit 60K You get 40K in profit, plus any salary, he gets 20K Next year you attract the attention of a competitor and they offer and you accept to sell.  You would get 100% of the proceeds. This is kind of a bad deal for him as you could easily play accounting tricks to diminish the company's profits and reduce his pay.  For the given example, you could pay yourself a 60K bonus and reduce the profit to zero and eliminate his compensation.  There should probably be a revenue metric included in his compensation. Edit: It is really nice to hear you have a desire to treat this person fairly.  Honesty in business is necessary for long term success.  I would simply make his salary dependent upon the revenue he generates.  For example, lets say you can make a widget for 4 and you expect to sell them for 10.  Your profit would be 6, and with the suggested split he would receive $2, you $4. Instead I would have him receive like 15% of the revenue generated This allows for some discounts for bulk items and covers the cost of processing sales.  It also allows him to share revenue with his staff.   Alternatively you could also do a split.  Perhaps 7.5% of revenue and 10% of profit.
His credit is likely impacted already for the fact it's in collection. My real concern is that he be 100% certain the debt collector actually has ownership of the debt. At first glance this sounds like it may be a scam, but if the debt was written off, it may have been sold for pennies on the dollar. So to the collector 20% of face value is a tidy profit. "The reason for selling a stock ""short"", is for when you believe the stock value will decrease in the near future. Here is an example: Today Exxon-Mobile stock is selling for $100 / share. You are expecting the price to decrease, so you want to short the stock, which means your broker (i.e. eTrade, etc) allows you to borrow shares without paying money, and those shares are transferred into your account, and then you sell them and receive money for the sale. But you didn't actually own those shares, you only borrowed them, so you need to return the shares to your broker sometime in the future.  Let's say you borrow 10 shares @ $100, and you sell them at the market price of $100, you receive $1,000 in your account. But you owe your broker 10 shares, which you need to return sometime in the future. A few days later, the share price has decreased to $80. Now you can buy 10 shares from the market at a total cost of $800. You get 10 shares, and return those shares to your broker. Since you originally took in $1,000, and you just paid out $800, you keep a resulting profit of $200" The Canada Revenue Agency describes in detail here what information businesses must generally include on their invoices so that GST/HST registrants can claim Input Tax Credits (ITCs) for the expenses. Quote: Sales invoices for GST/HST registrants You have to give customers who are GST/HST registrants specific   information on the invoices, receipts, contracts, or other business   papers that you use when you provide taxable goods and services. This   information lets them support their claims for input tax credits   (ITCs) or rebates for the GST/HST you charged. [...] The page quoted continues with a table describing what, specifically, needs to be on a sales invoice based on the total amount of the invoice; the requirements differ for: total sale under $30, total sale between $30 to $149.99, and total sale $150 or more. For the total sale under $30 category, the only things a sales invoice must contain to support an ITC claim are (1) the provider's business name, (2) the invoice date, and (3) the total amount paid/payable. i.e. When the total sale is under $30, there is no requirement for any GST/HST amount to be indicated separately, nor for a business number to be present on the invoice. Hence, IMHO (and I am neither an accountant nor a lawyer), if your Uber rides are for $30 or less, then you shouldn't expect a GST/HST number anyway, and a simple invoice as described should be enough for you to claim your ITCs. Whether or not the provider is registered in fact for GST/HST is beside the point. For amounts over $30, you need a bit more. While the page above specifies that the provider's business number should be included beginning with the next level of total sales,  there are exceptions to those rules described at another page mentioned, Exceptions to invoice requirements, that specifically apply to the taxi/limousine case. Quote: Exceptions to invoice requirements GST/HST registrants are required to keep the necessary documentation   to support their claim for ITCs and rebates. In certain circumstances   the documentation requirements have been reduced. [...] For taxi or limousine fares your books and records must show: So at a minimum, for fare in excess of $30 total, you should ask the driver to note either (a) the amount of GST/HST charged, or (b) a statement that the fare includes GST/HST. The driver's business number need not be specified. Consequently, if your receipt for a ride in excess of $30 does not contain any such additional information with respect to GST/HST, then I would expect the receipt does not satisfy the CRA's requirements for supporting your ITC claim. i.e. Keep your individual rides under $30 each, or else get a better receipt from the driver when it is above that amount. p.s. It should go without saying, but your rides, of course, must be considered reasonable business expenses in order to qualify for GST/HST ITCs for your business. Receipts for rides of a personal nature are not eligible, so be sure to maintain proper records as to the business purpose and destination for each ride receipt so claimed. Stocks represent partial ownership of the company. So, if you owned 51% of the stock of the company (and therefore 51% of the company itself), you could decide to liquidate all the  assets of the company, and you would be entitled to 51% of the proceeds from that sale.  In the example above, it would have to be Common Stock, as preferred stock does not confer ownership. *In a situation where it is not possible to buy 51% or more of the company (for example, it's not for sale), this is not possible, so the value of the stock could be much less. Regardless of whether a stock is owned by a retail investor or an institutional investor, it is subject to the same rules.  For example, say that as part of the buyout, 1 share of Company B is equivalent to 0.75 shares of Company A and any fractional shares will be paid out in cash.  This rule will apply to both the retail investor who holds 500 shares of Company B, as well as the asset manager or hedge fund holding 5,000,000 shares of Company B. "The usual pattern is that shareholders don't run companies in a practical sense, so ""if someone was just simply rich to buy > 50%, but does not know how to handle the company"" doesn't change anything. In large companies, the involvement of shareholders is limited to a few votes on key issues such as allocating profit (how much to keep in company vs pay in dividends) and choosing board members. And board members also don't run the company - they oversee how the company is being run, and choose executives who will actually run the company. If a rich person simply buys 50% and doesn't desire to get personally involved, then they just vote for whatever board members seem apropriate and forget about it." Once you own no shares for 31 days, it's game over. Even though the accounting has wash sales to consider, in the end, gains and losses all cancel to one net position of break even, gain or loss.  It's when there are shares remaining at the end of a period of time that the wash sale rules really impact the numbers. "You can't individually have 100% ownership if the 50/50 LLC is the owner of the new business; however, you can be allocated 100% of the profits and losses from the new business with the 50/50 LLC as owner of said business.  It requires a new LLC operating agreement that specially allocates profits and losses from the new business to you.  There is one catch under the Treasury Regs, the special allocation to you must have ""substantial economic effect"".  See Treasury Regulation (26 CFR) Section 1.704-1. http://www.medlawplus.com/library/legal/irsrulings/treareg1704-1.htm"