What's the best way to account for a risky investment - As an asset or an expense?
"I'm no accountant, but I think the way I'd want to approach this kind of thing in Gnucash would be to track it as an Asset, since it is. It sounds like your actual concern is that your tracked asset value isn't reflecting its current ""market"" value. Presumably because it's risky it's also illiquid, so you're not sure how much value it should have on your books. Your approach suggested here of having it as just as expense gives it a 0 value as an asset, but without tracking that there's something that you own. The two main approaches to tracking an investment in Gnucash are: Of course, both of these approaches do assume that you have some notion of your investment's ""current value"", which is what you're tracking. As the section on Estimating Valuation of the concepts guide says of valuing illiquid assets, ""There is no hard rule on this, and in fact different accountants may prefer to do this differently."" If you really think that the investment isn't worth anything at the moment, then I suppose you should track it at 0, but presumably you think it's worth something or you wouldn't have bought it, right? Even if it's just for your personal records, part of a regular (maybe annual?) review of your investments should include coming up with what you currently value that investment at (perhaps your best guess of what you could sell it for, assuming that you could find a willing buyer), and updating your records accordingly. Of course, if you need a valuation for a bank or for tax purposes or the like, they have more specific rules about how they are tracking what things are worth, but presumably you're trying to track your personal assets for your own reasons to get a handle on what you currently own. So, do that! Take the time to get a handle on the worth of what you currently own. And don't worry about getting the value wrong, just take your best guess, since you can always update it later when you learn new information about what your investment is worth."
You are comparing a risk-free cost with a risky return. If you can tolerate that level of risk (the ups and downs of the investment) for the chance that you'll come out ahead in the long-run, then sure, you could do that.   So the parameters to your equation would be: If you assume that the risky returns are normally distributed, then you can use normal probability tables to determine what risk level you can tolerate. To put some real numbers to it, take the average S&P 500 return of 10% and standard deviation of 18%.  Using standard normal functions, we can calculate the probability that you earn more than various interest rates: so even with a low 3% interest rate, there's roughly a 1 in 3 chance that you'll actually be worse off (the gains on your investments will be less than the interest you pay).  In any case there's a 3 in 10 chance that your investments will lose money. "What you are describing is a Chart of Accounts.  It's a structure used by accountants to categorise accounts into sub-categories below the standard Asset/Liability/Income/Expense structure. The actual categories used will vary widely between different people and different companies.  Every person and company is different, whilst you may be happy to have a single expense account called ""Lunch"", I may want lots of expense accounts to distinguish between all the different restaurants I eat at regularly.  Companies will often change their chart of accounts over time as they decide they want to capture more (or less) detail on where a particular type of Expense is really being spent. All of this makes any attempt to create a standard (in the strict sense) rather futile.  I have worked at a few places where discussions about how to structure the chart of accounts and what referencing scheme to use can be surprisingly heated!  You'll have to come up with your own system, but I can provide a few common recommendations: If you're looking for some simple examples to get started with, most personal finance software (e.g. GnuCash) will offer to create an example chart of accounts when you first start a session." "It's interesting that you use so many different risk measures. Here's what I'd like to know more in detail:  1) About the use of VaR. I've heard (from a friend, may be unreliable) that some investment managers like Neuberger Berman doesn't use VaR for assessing risk and maintaining capital adequacy requirements. Rather, some firms only rely on tracking error, beta, standard deviation, etc. Why do you think is this so? Isn't VaR supposed to be a widely accepted risk measure.  2) The whole ""Expected Shortfall vs. VaR"" debate. I've read some papers comparing Expected Shortfall and VaR. Mainly, they criticize VaR for not being able to consider the 1% probability left where losses can (probably) skyrocket to infinity. If I need to choose between the two, which do you think is better and why?" The expense ratio is stated as an annual figure but is often broken down to be taken out periodically of the fund's assets. In traditional mutual funds, there will be a percent of assets in cash that can be nibbled to cover the expenses of running the fund and most deposits into the fund are done in cash. In an exchange-traded fund, new shares are often created through creation/redemption units which are baskets of securities that make things a bit different. In the case of an ETF, the dividends may be reduced by the expense ratio as the trading price follows the index usually. Expense ratios can vary as in some cases there may be initial waivers on new funds for a time period to allow them to build an asset base. There is also something to be said for economies of scale that allow a fund to have its expense ratio go down over time as it builds a larger asset base. These would be noted in the prospectus and annual reports of the fund to some degree. SPDR Annual Report on page 312 for the Russell 3000 ETF notes its expense ratio over the past 5 years being the following: 0.20% 0.20% 0.22% 0.20% 0.21% Thus, there is an example of some fluctuation if you want a real world example. The problem you'll have is that premium income is a vague term so you have to figure out what they mean by a) premium and b) income. Gross or net of reinsurance and acquisition  costs? Written or earned basis?  Combined ratios are also a pig, very commonly they are loss ratio + expense ratio --- but of course loss ratio is losses incurred / premium earned while expense ratio is expenses paid / premium written so it's a self-inconsistent measure. And then there's investment income, and then there's reserve releases... I suggest that you use your own judgement on this. You can assign a reasonable percentage since it is impossible to monitor the hours using those assets. Example: 40 personal and 60 for business. It's really your call. I also suggest that you should be conservative on valuing the assets. Record the assets at it's lowest value. This is one of the most difficult scenarios in making your own financial statements. You can also use this approach, i will record the assets at its original cost then use a higher depreciation rate or double declining method of depreciation. If the assets have a depreciation rate of 20% per year (useful life of 5 years), i will make it 30%. the other 10% will add more expense and helps you not to overstate your Financial Statement. You can also use the residual value of the asset, but if you do this, you should figure out the reliable amount. I understand that this is not for tax reporting purposes. Therefore, there's no harm if you overstate your Financial statement. And even if you overstate, you can still adjust the cost of the asset. Along the way (in the middle of the year or year end), you will figure out the cost of the asset if it's over valued once the financial statement is done. Financial advisers like to ask lots of questions and get nitty-gritty about investment objectives, but for the most part this is not well-founded in financial theory.  Investment objectives really boils down to one big question and an addendum.  The big question is how much risk you are willing to tolerate.  This determines your expected return and most characteristics of your portfolio. The addendum is what assets you already have (background risk).  Your portfolio should contain things that hedge that risk and not load up on it.  If you expect to have a fixed income, some extra inflation protection is warranted.  If you have a lot of real estate investing, your portfolio should avoid real estate.  If you work for Google, you should avoid it in your portfolio or perhaps even short it. Given risk tolerance and background risk, financial theory suggests that there is a single best portfolio for you, which is diversified across all available assets in a market-cap-weighted fashion. "In economics, there is a notion called the Sunk Cost Fallacy.  In a nutshell, the sunk cost fallacy says that human beings tend to prefer to ""throw good money after bad"" because of a strong loss aversion.  That, coupled with how we frame an issue, makes it very tempting to say, ""if I just add these funds, I'll recoup my loss plus..."" In reality, the best best is to ignore sunk costs.  (I know, far easier said than done, but bear with me a second.)  How much you've invested is really irrelevant.  The only question worth asking is this: ""Would I invest this money in the asset today?"" Put it this way - any money you spend on ""rescuing"" this upside mortgage is an investment that trades ready funds for a little more equity.  Knowing that the mortgage is $100K in excess of the value, why buy that asset?  If you could do a HARP, different story - but as you say, you can't. As such, buying into that investment is not the best use of your funds. You are throwing good money after bad.  Invest your money where it will earn the best rate of return - not where your heart lead you." Here's how I think about money. There are only 3 categories / contexts (buckets) that my earned money falls into. Savings is my emergency fund. I keep 6 months of total expenses (expenses are anything in the consumption bucket). You can be as detailed as you want with this area but I tend to leave a fudge factor. In other words, if I estimate that I spend approximately $3,000 a month in consumption dollars then I'll save $3,500 times 6 in the bank. This money needs to be liquid. Some people use a HELOC, other people use their ROTH contributions. In any case, you need to put this money some place you can get access to it in case you go from accumulation (income exceed expenses) to decumulation mode (expenses exceed income). This money is distinct from consumption which I will cover in paragraph three. Investments are stocks, bonds, income producing real estate, small businesses, etc. These dollars require a strategy. The strategy can include some form of asset allocation but more importantly a timeline. These are the dollars that are working for you. Each dollar placed here will multiply over time. Once you put a dollar here it shouldn't be taken out unless there is some sort of catastrophe that your savings can't handle or your timeline has been achieved. Notice that rental real estate is included so liquidating stocks to purchase rental real estate is NOT considered removing investment dollars. Just reallocating based on your asset allocation. This bucket includes 401k's, IRAs, all tax-sheltered accounts, non-sheltered brokerage accounts, and rental real estate. In general your primary residence is not included in this bucket. Some people include the equity of their primary residence in the investment column but it can complicate the equation and I prefer to leave it out. The consumption bucket is the most important bucket and the one you spend the most time with. It requires a budget. This includes your $5 magazine and your $200 bottle of wine. Anything in this bucket is gone. You can recover a portion of it by selling it on ebay for $3 (these are earned dollars) but the original $5 is still considered spent. The reason your thought process in this area is distinct from the other two, the decisions made in this area will have the biggest impact on your personal finances. Warren Buffett was famous for skimping on haircuts because they are worth thousands of dollars down the road if they are invested instead. Remember this is a zero-sum game so every $1 not consumed is placed in one of the other buckets. Once your savings bucket is full every dollar not consumed is sent to investments. Remember to include everything that does not fit in the other two buckets. Most people forget their car insurance, life insurance, tax bill at the end of the year, accountant bill, etc. In conclusion, there are three buckets. Savings, which serve as your emergency bucket. This money should not be touched unless you switch from accumulation to decumulation. Investments, which are your dollars that are working for you over time. They require a strategy and a timeline. Consumption, which are your monthly expenses. These dollars keep you alive and contribute to your enjoyment. This is a short explanation of my use of money. It can get as complicated and detailed as you want it to be but as long as you tag your dollars correctly you'll be okay IMHO. HTH. "These sort of issues in structuring your personal finances relative to expenses can get complicated quickly, as your example demonstrates.  I would recommend a solution that reduces duplication as much as possible- and depending on what information you're interested in tracking you could set it up in very different ways. One solution would be to create virtual sub accounts of your assets, and to record the source of money rather than the destination.  Thus, when you do an expense report, you can limit on the ""his"" or ""hers"" asset accounts, and see only the expenses which pertain to those accounts (likewise for liabilities/credit cards). If, on the other hand, you're more interested in a running sum of expenses- rather than create ""Me"" and ""Spouse"" accounts at every leaf of the expense tree, it would make much more sense to create top level accounts for Expenses:His:etc and Expenses:Hers:etc.  Using this model, you could create only the sub expense accounts that apply for each of your spending (with matching account structures for common accounts)." It depends on whether or not you are referring to realized or unrealized gains.  If the asset appreciation is realized, meaning you've sold the asset and actually collected liquidity from it, then Derek_6424246 has provided a good route to follow.   However, if the gains are unrealized, meaning only that the current value of the underlying asset(s) have increased or decreased, then you might want to record this under an Income:Unrealized Gains account.  One of the main distinctions between the two are whether or not you have a taxable event (realized) or just want to better track your net worth at a given time (unrealized).   For example, I generally track my retirement accounts increase in value sans interest, dividends and contributions, as income from an Income:Unrealized Gains account.  I can still reconcile it with my statements, and it shows an accurate picture for my net worth, but the money is not liquid nor taxed and is more for informational purposes than anything.   And no, I don't create an additional Expense account here to track losses.  Just think of Unrealized Gains as an income account where the balance will fluctuate up and down (and potentially even go negative) over time. "First of all, ""going risky"" doesn't mean driving to Las Vegas and playing roulette. The real meaning is that you can afford higher risk/return ratio compared to a person who will retire in the following ten years. Higher return is very important since time works for you and even several extra percent annually will make a big difference in the long run because of compound interest effect. The key is that this requires the investment to not be too risky - if you invest in a single venture and it fails you lose all the money and that's worse that some conservative investment that could yield minimum income. So you still need the investment to be relatively safe. Next, as user Chris W. Rea mentions in the comment funds and ETFs can be very risky - depending on the investment policy they can invest into some very risky ventures or into some specific industry and that poses more risk that investing into ""blue chips"" for example. So a fund or an ETF can be a good fit for you if you choose a right one." You may be able to choose.  As a small business, you can expense certain depreciable assets (section 179).  But by choosing to depreciate the asset, you are also increasing the cost-basis of the property.  Are you planning to sell the property in the next couple of years?  Do you need a higher basis? Section 179 - Election to expense certain depreciable business assets "When you're calculating the cash flows used to compute an IRR, with regard to the expenses used to calculate those cash flows:  Do you assume that expenses are going to be higher than they would be today, by using an assumed inflation rate?   Or is everything (all cash flows) assumed to be in today's dollars, and you account for inflation's effect on your actual returns at ""the end"" by subtracting off the inflation rate from the IRR?" If you were a business, all your assets would have a dollar value, so when you sold them you'd decrease the amount of assets by that amount and increase in cash, and if there was a profit on the sale it would go in as income, if there was loss it would count as a cost (or a loss)... so if there was a profit it would increase Equity, a loss then it would decrease Equity.  Since it's not really worthwhile doing a estimated cost for everything that you have, I'd just report it as income like you are doing and let the amount of equity increase proportionately. So, implicitly you always had roughly that amount of equity, but some of it was in the form of assets, and now you're liquidating those assets so the amount shows up in GnuCash. When you buy new things you might sell later, you could consider adding them as assets to keep track of this explicitly (but even then you have problems-- the price of things changes with time and you might not want to keep up with those price changes, it's a lot of extra work for a family budget) -- for stuff you already have it's better to treat things as you are doing and just treat the money as income-- it's easier and doesn't really change anything-- you always had that in equity, some of it was just off the books and now you are bringing it into the books.