Using Loan to Invest - Paying Monthly Installments by Selling Originally Bought Shares
In addition to the answer from CQM, let me answer your 'am I missing anything?' question. Then I'll talk about how your approach of simplifying this is making it both harder and easier for you. Last I'll show what my model for this would look like, but if you aren't capable of stacking this up yourself, then you REALLY shouldn't be borrowing 10,000 to try to make money on the margin. Am I missing anything? YES. You're forgetting (1) taxes, specifically income tax, and (2) sales commissions//transaction fees.  On the first: You have not considered anything in your financial model for taxes. You should include at least 25% of your expected returns going to taxes, because anything that you buy... and then sell within 12 months... is taxed as income. Not capital gains. On the second: you will incur sales commissions and/or transaction fees depending on the brokerage you are using for your plan. These tend to vary widely, but I would expect to spend at least $25 per sale. So if I were building out this model I would think that your break-even would have to at least cover: monthly interest + monthly principal payment income tax when sold commissions and broker's fees every time you sell holdings On over-simplifying: You have the right idea with thinking about both interest and principal in trying to sketch this out. But as I mentioned above, you're making this both harder and easier for yourself. You are making it harder because you are doing the math wrong. The actual payment for this loan (assuming it is a normal loan) can be found most easily with the PMT function in Excel: =PMT(rate,NPER,PV,FV)... =PMT(.003, 24, -10000, 0). That returns a monthly payment  (of principal + interest) of 432.47.  So you actually are over-calculating the payment by $14/month with your ballpark approach. However, you didn't actually have all the factors in the model to begin with, so that doesn't matter much.  You are making it artificially easier because you have not thought about the impact of repaying principal. What I mean is this--in your question you indicate:  I'm guessing the necessary profit is just the total interest on this loan = 0.30%($10000)(24) = $720 USD ? So I'll break even on this loan - if and only if - I make $720 from stocks over 24 months (so the rate of return is 720/(10000 + 720) = 6.716%). This sounds great-- all you need is a 6.716% total return across two years. But, assuming this is a normal loan and not an 'interest-only' loan, you have to get rid of your capital a little bit at a time to pay back the loan. In essence, you will pay back 1/3 of your principal the first year... and then you have to keep making the same Fixed interest + principal payments out of a smaller base of capital.  So for the first few months you can cover the interest easily, but by the end you have to be making phenomenal returns to cover it.  Here is how I would build a model for it (I actually did... and your breakeven is about 1.019% per month. At that outstanding 12.228% annual return you would be earning a whopping $4.) At least as far as the variables are concerned, you need to be considering: Your current capital balance (because month 1 you may have $10,000 but month 2 you have just 9,619 after paying back some principal).  Your rate of return (if you do this in Excel you can play with it some, but you should save the time and just invest somewhere else.) Your actual return that month (rate of return * existing capital balance).  Loan payment = 432 for the parameters you gave earlier.  Income tax = (Actual Return) * (.25). With this kind of loan, you're not actually making enough to preserve the 10,000 capital and you're selling everything you've gained each month.  Commission = ($25 per month) ... assuming that covers your trade fees and broker commissions. I guarantee you that this is not the deal breaker in the model, so don't get excited if you think I'm over-estimating this and you realize that Scottrade or somewhere will let you have trades at $7.95 each.   Monthly ending balance == next month's starting capital balance.  Stack it all up in Excel for 24 months and see for yourself if you like. The key thing you left out is that you're repaying each month out of capital that you'd like to use to invest with. This makes you need much higher returns.  Even if your initial description wasn't clear and this is an interest-only loan, you're still looking at a rate of about 7.6% annually that you need to hit in order to just break even on the costs of holding the loan and transferring your gains into cash. The market can stay irrational longer than you can remain solvent -John Maynard Keynes The stocks could stagnate and trade in a thin range, or decline in value. You assume that your stocks will offer you ANY positive return for every month over 24 months. Just one month of negative returns puts you underwater. Thats whats wrong with it.  Even if you identified any stock that has been up every month for a consecutive 24 months in the past, there is nothing that says it will be so in the future, and a broad market selloff will effect both indexes as well as individual stocks.  Literally any adverse macroeconomic event in the next two years will put you underwater on your loan, no matter how much research you do on individual stocks. I will add one point missing from the answers by CQM and THEAO. When you take a loan and invest the proceeds, the interest that you pay on the loan is deductible on Schedule A, Line 14 of your Federal income tax return under the category of Investment Interest Expense.  If the  interest expense is larger than all your investment earnings (not just those from the loan proceeds), then you can deduct at most the amount of the earnings, and carry over the excess investment interest paid this year for deduction  against investment earnings in future years. Also, if some of the earnings are long-term capital gains and you choose to deduct the corresponding investment interest expense, then those capital gains are taxed as ordinary income instead of at the favored LTCG rate. You also have the option of choosing to deduct only that amount of interest that offsets dividend (and short-term capital gain) income that is taxed at ordinary rates, pay tax at the LTCG rate on the capital gains, and carry over rest of the interest for deduction in future years. In previous years when the tax laws called for  reduction in the Schedule A deductions for high-income earners, this investment interest expense was exempt from the reduction. Whether future tax laws will allow this exemption depends on Congress. So, this should be taken into account when dealing with the taxes issue in deciding whether to take a loan to invest in the stock market.
Because interest is tax deductible. I don't know much about the Chevron deal, but I'm an EM debt analyst and typically the issue you have is that dividends are taxed but interest is not. So to move money from a subsidiary instead of putting in equity and getting dividends (tax inefficient), instead you give debt and get interest back. You get a little less flexibility on payment but you more than make up for that (on average) with tax efficiency.   Don't think of it as a loan at all. Think of it as a pseudo-equity investment with required dividends.  Revenue is not taxed, profit is. Interest comes out of profit, dividends however are issued after profit.  This could all be wrong vis-a-vis Chevron. This is just how most of the companies I look at work. You can't make money on the way down if it was your money that bought the shares when the market was up.  When you sell short, borrowing lets you tap into the value without paying for it. That way, when the price (hopefully) drops you profit from the difference. In your example, if you hadn't paid the £20 in the first place, then you would actually be up £5. But since you started with £20, you still show loss. As others said, borrowing is the definition of selling short. It is also simply the only way the math works. Of course, there is a large risk you must assume to enjoy benefiting from something you do not own! "With (1), it's rather confusing as to where ""interest"" refers to what you're paying and where it refers to what you're being paid, and it's confusing what you expect the numbers to work out to be. If you have to pay normal interest on top of sharing the interest you receive, then you're losing money. If the lending bank is receiving less interest than the going market rate, then they're losing money. If the bank you've deposited the money with is paying more than the going market rate, they're losing money. I don't see how you imagine a scenario where someone isn't losing money. For (2) and (3), you're buying stocks on margin, which certainly is something that happens, but you'll have to get an account that is specifically for margin trading. It's a specific type of credit with specific rules, and you if you want to engage in this sort of trading, you should go through established channels rather than trying to convert a regular loan into margin trading. If you get a personal loan that isn't specifically for margin trading, and buy stocks with the money, and the stocks tank, you can be in serious trouble. (If you do it through margin trading, it's still very risky, but not nearly as risky as trying to game the system. In some cases, doing this makes you not only civilly but criminally liable.) The lending bank absolutely can lose if your stocks tank, since then there will be nothing backing up the loan." Because they receive compensation (generally interest + dividends) for loaning out the shares. I own an asset X.   Somebody else wants to borrow asset X for some time period.   I agree to loan them asset X in return for some form of compensation (generally a rate of interest plus, in this specific case, any dividend payments).  The reasons why I own asset X, and why they want to borrow asset X are irrelevant to the transaction. The only relevant points are the amount of compensation and the risk that they might default on the loan. This applies equally well to shares as to money or any other kind of loan-able asset. Stuff I wish I had known, based on having done the following: Obtained employment at a startup that grants Incentive Stock Options (ISOs);  Early-exercised a portion of my options when fair market value was very close to my strike price to minimize AMT; made a section 83b) election and paid my AMT up front for that tax year. All this (the exercise and the AMT) was done out of pocket. I've never see EquityZen or Equidate mention anything about loans for your exercise. My understanding is they help you sell your shares once you actually own them. Stayed at said startup long enough to have my exercised portion of these ISOs vest and count as long term capital gains;  Tried to sell them on both EquityZen and Equidate with no success, due to not meeting their transaction minimums.  Initial contact with EquityZen was very friendly and helpful, and I even got a notice about a potential sale, but then they hired an intern to answer emails and I remember his responses being particularly dismissive, as if I was wasting their time by trying to sell such a small amount of stock. So that didn't go anywhere. Equidate was a little more friendly and was open to the option of pooling shares with other employees to make a sale in order to meet their minimum, but that never happened either.  My advice, if you're thinking about exercising and you're worried about liquidity on the secondary markets, would be to find out what the minimums would be for your specific company on these platforms before you plunk any cash down. Eventually brought my request for liquidity back to the company who helped connect me with an interested external buyer, and we completed the transaction that way. As for employer approval - there's really no reason or basis that your company wouldn't allow it (if you paid to exercise then the shares are yours to sell, though the company may have a right of first refusal). It's not really in the company's best interest to have their shares be illiquid on the secondary markets, since that sends a bad signal to potential investors and future employees. You're trying to mitigate the risk of having your investments wiped out by fraud committed by your broker by using margin loans to buy stock secured by other, non-cash assets in your account. The solution that you are proposing does not make any sense at all. You mitigate a very low probability/high impact risk by doing something that comes with a high probability/medium impact risk.  In addition to interest costs, holding stocks on margin subjects you to the very real risk of being forced to sell assets at inopportune times to meet margin calls. Given the volatility that the markets are experiencing in 2011, there is a high risk that some irrational decision in Greece could wipe you out. If I were worried about this, I would: If you have enough money that SIPC protection limits are an issue, you desperately need a financial adviser. Do not implement any strategy involving margin loans until you talk to a qualified adviser. "People borrow money all the time to buy a house. Banks will lend money on one (up to 80%, sometimes more), because they consider it an ""investment."" If you own a large company and want to expand, a bank or bond issuer will first look at what you plan to do with the money, like build new factories, or whatever. Based on their experience, they may judge that you will earn enough money to pay them back. If you don't, they may ""repossess"" your factories and sell them to someone who can pay. As protection, you may be asked to ""mortgage"" your existing company to protect the lenders of the new money. If you don't pay back the money, the lenders get not only your new ""factories"" but also your existing company." ELI5 - you sell something that you don't own with the expectation that it will go down, and then you buy it back when it goes down in order to lock in profit.  You are charged fees to borrow the stock from someone else who currently owns it, and you also run the risk of the market going against you by going up. Exact rules may be different depending on the size of the investor, the specific broker, and the country.  For both the US and Canada, short sales occur only through one's margin account.  And shares that are borrowed for shorting only come from a margin account. Shares held in a cash account are not available for shorting.  From Wikipedia Short (finance) - The speculator instructs the broker to sell the shares and the   proceeds are credited to his broker's account at the firm upon which   the firm can earn interest. Generally, the short seller does not earn   interest on the short proceeds and cannot use or encumber the proceeds   for another transaction. As with many questions, I'd suggest you contact your broker for the exact details governing your account. "Now, my own answer:  If you join and receive equity, do the 1/3 split as a max. Truthfully, if it were my company, I would try to negotiate with you to only give you 15%--20% because as an advisor you're not going to be involved in executing the idea to turn it into a business.  If you contribute capital, do it as a loan. End of story.  You don't own more because you financed growth... you shouldn't. The growth will have come because of the collective performance of the whole team. You should get paid back at a ""fair"" rate for your investment... if the company can handle it, I would argue something like 10% interest is reflective of the risk you're taking with your money.  If the finances are so tight that the interest repayment isn't an option, do the math behind what you should be paid for the loan in interest, and convert that to shares or equity somehow, and get paid back for the invested capital.  If the company can't repay your loan, the business model may not be sound enough, or developed enough, to be investing in to begin with." Are there any laws against doing this?  so long as you are truthful in your application for the loan, none that I know of - technically you could use the loan to pay for school and the cash that you would have used instead to invest.   Are there other reasons why this is a very bad idea? I think you've already identified the biggest one, but here are my reasons: Will you go broke or go to jail? Likely not, but there is significant risk in investing with borrowed money. You might come out ahead, but you might also lose a bundle.  If you're willing to take that risk, that's your right, but I would not call it a good idea under any circumstances. It's incredibly foolish because it fails to use the investments as collateral to secure the loan. So instead of paying 5% or less for a loan secured by liquid assets, you'll be paying 10% or more for an unsecured loan. I do leveraged investments all the time and make a reasonable amount of money doing it (at high risk, I concede). I always use the investment to secure the loan and, as a result, pay a very low interest rate (since the lender can sell of my investments if I fail to repay the loan, reducing their risk dramatically). An unsecured loan would cost several times more. What you're getting at is the same as investing with leverage. Usually this comes in the form in a margin account, which an investor uses to borrow money at a low interest rate, invest the money, and (hopefully!) beat the interest rate.  is this approach unwise? That completely depends on how your investments perform and how high your loan's interest rate is. The higher your loan's interest rate, the more risky your investments will have to be in order to beat the interest rate. If you can get a return which beats the interest rates of your loan then congratulations! You have come out ahead and made a profit. If you can keep it up you should make the minimum payment on your loan to maximize the amount of capital you can invest. If not, then it would be better to just use your extra cash to pay down the loan.  [are] there really are investments (aside from stocks and such) that I can try to use to my advantage? With interest rates as low as they are right now (at least in the US) you'll probably be hard-pressed to find a savings account or CD that will return a higher interest rate than your loan's. If you're nervous about the risk associated with investing in stocks and bonds (as is healthy!), then know that they come in a wide spectrum of risk. It's up to you to evaluate how much risk you're willing to take on to achieve a higher return. You are the one lending yourself the shares to sell;you purchase the stock at market price and sell at the strike price of the option to the put seller when you exercise the option. I've been looking through annual reports of some Canadian insurance companies. Having serious trouble with their reporting; it varies widely. I've been trying to create a historic look at the combined ratios, and have been comparing income statements. Maybe that's the wrong place to look.