How a company can afford to give away so many shares as part of its ESOP
This question is very open ended. But I'll try to answer parts of it. An employer can offer shares as part of a compensation package. Instead of paying cash the employer can use the money to buy up shares and give them to the employees. This is done to keep employees for longer periods of time and the employer may also want to create more insider ownership for a number of reasons. Another possibility is issuance of secondary offerings that are partially given to employees. Secondary offerings often lower the price of the shares in the market and create an incentive for employees to stay until the stock price rises. All of these conditions can be stipulated, look up golden handcuffs. Usually stock gifts are only given to a few high level employees and as part of a bonus package. It is very unusual to see a mature company regularly give away large amounts of stock, as this is a frowned upon practice. Start ups often pay their employees with stock up until the company is acquired or goes public. There are two sources for shares that employees buy through ESOPs. A company can simply buy the shares on the open market. The company must pay for the stock, but the employee then pays the company for the shares. If employees get a discount on the ESOP shares, the company would pay for that percentage directly. The company can choose to issue new shares. These new shares dilute the ownership of all the other current stockholders. While #2 is common when companies issue stock options, I'd be surprised to see it with an ESOP. In most cases, employees are limited in the amount of their salary they can devote towards the ESOP. If that limit is 10% and the discount that the employees get is 10%, the cost on a per-employee basis would only be 1% of that employees salary, which is a small expense. Companies theoretically have an infinite number of equity units at their disposal.  Issuance must be approved according to its founding contracts. If an equity is trading on an open market then the price of each unit issued in lieu of cash compensation is known.  Even if an equity doesn't trade openly, bidders can be solicited for a possible price or an appraisal.  This can be a risky route for the potentially compensated. Market capitalizations are frequently generally approximately equal to the sales of a company.  Salaries and wages are frequently generally two thirds of sales. It is indeed expensive for the average company to compensate with equity, thus so few do, usually restricting equity compensation to executives and exceptional laborers.  Besides, they frequently have enough cash to pay for compensation, avoiding transaction costs. For companies in growth industries such as technology or medicine, their situations are usually reversed: cash constrained yet equity abundant because of large investment and dearly priced equities.  For a company trading at a market capitalization multiplied by forty times the revenue, compensating with equity is inexpensive.
"BigCo is selling new shares and receives the money from Venturo. If Venturo is offering $250k for 25% of the company, then the valuation that they are agreeing on is a value of $1m for the company after the new investment is made.  If Jack is the sole owner of one million shares before the new investment, then BigCo sells 333,333 shares to Venturo for $250k.  The new total number of shares of BigCo is 1,333,333; Venturo holds 25%, and Jack holds 75%. The amount that Jack originally invested in the company is irrelevant.  At the moment of the sale, the Venturo and Jack agree that Jack's stake is worth $750k.  The value of Jack's stake may have gone up, but he owes no capital gains tax, because he hasn't realized any of his gains yet.  Jack hasn't sold any of his stake.  You might think that he has, because he used to hold 100% and now he holds 75%.  However, the difference is that the company is worth more than was before the sale.  So the value of his stake was unchanged immediately before and after the sale. Jack agrees to this because the company needs this additional capital in order to meet its potential. (See ""Why is stock dilution legal?"") For further explanation and another example of this, see the question ""If a startup receives investment money, does the startup founder/owner actually gain anything?"" Your other scenario, where Venturo purchases existing shares directly from Jack, is not practical in this situation.  If Jack sells his existing shares, you are correct that the company does not gain any additional capital.  An investor would not want to invest in the company this way, because the company is struggling and needs new capital." All shares of the same class are considered equal. Each class of shares may have a different preference in order of repayment.  After all company liabilities have been paid off [including bank debt, wages owing, taxes outstanding, etc etc.], the remaining cash value in a company is distributed to the shareholders. In general, there are 2 types of shares: Preferred shares, and Common shares.  Preferred shares generally have 3 characteristics: (1) they get a stated dividend rate every year, sometimes regardless of company performance; (2) they get paid out first on liquidation; and (3) they can only receive their stated value on liquidation - that is, $1M of preferred shares will be redeemed for at most $1M on liquidation, assuming the corporation has at least that much cash left. Common Shares generally have 4 characteristics: (1) their dividends are not guaranteed (or may be based on a calculation relative to company performance), (2) they can vote for members of the Board of Directors who ultimately hire the CEO and make similar high level business decisions; (3) they get paid last on liquidation; and (4) they get all value remaining in the company once everyone else has been paid. So it is not the order of share subscription that matters, it is the class. Once you know how much each class gets, based on the terms listed in that share subscription, you simply divide the total class payout by number of shares, and pay that much for each share a person holds. For companies organized other-than as corporations, ie: partnerships, the calculation of who-gets-what will be both simpler and more complex. Simpler in that, generally speaking, a partnership interest cannot be of a different 'class', like shares can, meaning all partners are equal relative to the size of their partnership interest. More complex in that, if the initiation of the company was done in an informal way, it could easily become a legal fight as to who contributed what to the company. Employee Stock Purchase Plans (ESPPs) were heavily neutered by U.S. tax laws a few years ago, and many companies have cut them way back. While discounts of 15% were common a decade ago, now a company can only offer negligible discounts of 5% or less (tax free), and you can just as easily get that from fluctuations in the market. These are the features to look for to determine if the ESPP is even worth the effort: As for a cash value, if a plan has at least one of those features, (and you believe the stock has real long term value), you still have to determine how much of your money you can afford to divert into stock. If the discount is 5%, the company is paying you an extra 5% on the money you put into the plan. I've done a rights offering once. Basically you had to pay money to exercise the right to buy. The offer was far below market rate, so the company was making money, and overall by exercising you ended up in a bit of a better position, even though your original position was diluted.  I'm not really sure what you're asking though. The money does come from the people exercising the right. "The main thing is the percentage of the company represented by the shares. Number of shares is meaningless without total shares. If you compute percentage and total company value you can estimate the value of the grant. Or perhaps more useful for a startup is to multiple the percentage by some plausible ""exit"" value, such as how much the company might sell for or IPO for. Many grants expire when or soon after you leave the company if you don't ""cash out"" vested shares when you leave, this is standard, but do remember it when you leave.  The other major thing is vesting. In the tech industry, vesting 1/4 after a year and then the rest quarterly over 3 more years is most common." Is my understanding correct? It's actually higher than that - he exercised options for 94,564 shares at $204.16 and sold them for $252.17 for a gain of about $4.5 Million.  There's another transaction that's not in your screenshot where he sold the other 7,954 shares for another $2 Million. What do executive directors usually do with such profit?  It's part of his compensation - it's anyone's guess what he decided to do with it. Is it understood that such trade profits should be re-invested back to the company? No - that is purely compensation for his position (I'm assuming the stock options were compensation rather then him buying options in the open market).  There generally is no expectation that trading profits need to go back into the company.  If the company wanted the profits reinvested they wouldn't have distributed the compensation in the first place. Well, if one share cost $100 and the company needs to raise $10000, then the company will issue 100 shares for that price.  Right? However, say there's 100 shares out there now, then each share holder owns 1/100th of the company. Now the company will remain the same, but it's shared between 200 shareholders after the issuing of new shares.  That means each share holder now owns 1/200th of the company.  And hence only gets 1/200th of their earnings etc. It basically only affects the company's dealings with its own stock, not with operational concerns.  If the company were to offer more stock for sale, it would get less cash.  If it had a stock buy-back program, it could buy more shares for the same money.  If it was to offer to acquire another company in exchange for its own stock, the terms would be less attractive to the other company's owners.  Employee stock remuneration, stock options, and so forth would be affected, so there might be considerations and tax consequences for the company. "By issuing additional equity. In this case, the pie isn't ""fixed,"" it's getting bigger. Now, to avoid lawsuits and other potential issues (some of which may be unavoidable), the owner will likely need to subscribe for additional equity himself.  Example:  100 shares outstanding. 51 to owner, 49 to 2 others.  That 49 will have to equal 20%, as none of their shares are being sold (likely). This means total shares will need to be increased to 245.  Subtract 49 from that number: 196  Marcus gets half of that at a determined price. 98  Owner must increase his stake from 51 to 98 shares. To do so, he'll need to contribute additional cash for the same price Marcus gets in on. That could be expensive." A company typically goes public in order to bring in additional capital. In an IPO, the company (through its officials) will typically do so by issuing additional shares, and offering to sell those to investors. If they did not do that, then there would be no net capital gain for the company; if person A sells share in company C to person B, then company C does not benefit directly from the exchange. By issuing and selling additional shares, the total value of all stock in the company can increase. Being publicly traded also greatly increases the confidence in the valuation of the company, as a consequence of the perfect market theory. There is nothing in this that says that initial investors (cofounders, employees, etc.) need to sell their shares in the process. They might choose to do so, or they might not; or they might be prevented from doing so by terms of any agreements that they have signed or by insider trading laws. Compare What happens to internal stock when a company goes public? Depending on specifics, it might be reasonable for the company to perform a share split prior to the initial public offering. That, however, doesn't affect the total value of the shares, only the price per share. A company generally sells a portion of its ownership in an IPO, with  existing investors retaining some ownership.  In your example, they believe that the entire company is worth $25MM, so in order to raise $3MM it is issuing stock representing 12% of the ownership stake (3/25), which dilutes some or all of the existing stockholders' claims. The reason a company creates more stock is to generate more capital so that this can be utilized and more returns can be generated. It is commonly done as a follow on public offer. Typically the funds are used to retire high cost debts and fund future expansion. What stops the company from doing it?   Are Small investors cheated?   It's like you have joined a car pool with 4 people and you are beliving that you own 1/4th of the total seats ... so when most of them decide that we would be better of using Minivan with 4 more persons, you cannot complain that you now only own 1/8 of the total seats. Even before you were having just one seat, and even after you just have one seat ... overall it maybe better as the ride would be good ... :) If a deal is struck, you're part of that deal because you own shares.  If someone offers $10/share for the entire company, you'll get that.  If the stock price is $1.50 and someone offers $2/share, you'll get that. You could think of points 1 and 3 combined to be similar to buying shares and selling calls on a part of those shares. $50k is the net of the shares and calls sale (ie without point 3, the investor would pay more for the same stake). Look up convertible debt, and why it's used. It's basically used so that both parties get 'the best of both world's' from equity and debt financing.   Who is he selling his share to in point 2 back to the business or to outside investors? If Jack owns all of the one million founding shares (which I assume you meant), and wants to transfer 250,000 shares to Venturo, then he is just personally selling shares to Venturo and the corporation gains nothing. If Jack does not own all of the founding shares, and the corporation had retained some, then the corporate shares could be sold to raise cash for the corporation. Usually in situations like this, the corporation will create more shares, diluting existing shareholders, and then sell the new shares on the open market to raise cash.