Implications of receiving small amounts of money on the side
HMRC may or may not find out about it; the risks and penalties involved if they do find out make it unwise not to just declare it and pay the tax on it. Based on the fact you asked the question, I am assuming that you currently pay all your tax through PAYE and don't do a tax return. You would need to register for Self Assessment and complete a return; this is not at all difficult if your tax situation is straightforward, which it sounds like yours is. Then you would owe the tax on the additional money, at whatever applicable rate (which depends on how much you earn in your main job, the rate tables are here: https://www.gov.uk/income-tax-rates/current-rates-and-allowances ). If it truly is a one off you could simply declare it on your return as other income, but if it is more than that then you would need to look at setting up as Self Employed - there is some good advice on the differences here: http://www.brighton-accountants.com/blog/tax-self-employment-still-employed/ :  Broadly, you are likely to be running a business if you have a regular, organised activity with a profit motive, which continues for at least a few months. If the work is one-off, or very occasional (say, a few times per year), or not very organised, or of very low value (say, under £2,000 per year), then it might qualify as casual income. If you think it is beyond the definition of casual income then you would also need to pay National Insurance, as described in the previous link, but otherwise the tax treatment would be the same.
"Sounds like your grandmother's estate had taxable income and the estate did not pay the estate ""INCOME"" tax.  Rather the estate shifted the burden to pay that tax on the beneficiaries which is why you received a K1.  If that K1 reports income received by you, then YES you would have to amend your tax return.  I am in exactly that same situation now.  After the October 15 deadline to file 2012 tax returns, I received a K1 for income received from my dad's estate.  I now have to file a late amended 2012 income tax return and pay income tax on what I inherited. My dad had a small estate, but the money that made up that small estate all came from an IRA he had.  He designated the estate as his beneficiary.  So when the stocks in the IRA were sold, that all became taxable income to the beneficiaries of the estate. Anything involving taxes is confusing at best.  But do not confuse estate income tax, with estate tax -- they are two different taxes. Hope this helps." As someone who has worked for both an insurance carrier and an insurance agent, the reason people buy insurance is two fold: to spread risk out, and to get the benefits (when applicable) of approaching risk as a group. What you are really doing when you buy insurance is you are buying in to a large group of people who are sharing risk.  You put money in that will help people when they take a loss, and in exchange get a promise of having your losses covered.  There is an administrative fee taken by the company that runs the group in order to cover their costs of doing business and their profits that they get for running the group well (or losses they take if they run it poorly.) Some insurances are for profit, some are non-profit; all work on the principle of spreading risk around though and taking risk as a larger group. So let's take a closer look at each of the advantages you get from participating in insurance.  The biggest and most obvious is the protection from catastrophic loss.  Yes, you could self-insure with a group size of one, by saving your money and having no overhead (other than your time and the time value of your money) but that has a cost in itself and also doesn't cover you against risk up front if you aren't already independently wealthy.  A run of bad luck could wipe you out entirely since you don't have a large group to spread the risk around.  The same thing can still happen to insurance companies as well when the group as a whole takes major losses, but it's less likely to occur because there are more rare things that have to go wrong.  You pay an administrative overhead for the group to be run for you, but you have less exposure to your own risks in exchange for a small premium. Another significant but less visible advantage is the benefit of being part of a large group.  Insurance companies represent a large group of people and lots of business, so they can get better rates on dealing with recovering from losses.  They can negotiate for better health care rates or better repair rates or cheaper replacement parts.  This can potentially save more than the administrative overhead and profit that they take off the top, even when compared to self-insuring. There is an element of gambling to it, but there are also very real financial benefits to having predictable costs.  The value of that predictability (and the lesser need for liquid assets) is what makes insurance worth it for many people.  The value of this group benefit does decrease a lot as the value of the insurance coverage (the amount it pays out) decreases.  Insurance for minor losses has a much smaller impact on liquidity and is much easier to self insure.  Cheaper items that have insurance also tend to be high risk items, so the costs tend to be very high relative to the amount of protection.  If you are financially able, it may make more sense to self-insure in these cases, particularly if you tend to be more cautious.  It may make sense for those who are more prone to accidents with their devices to buy insurance, but this selection bias also drives the cost up further.  Generally, the reason to buy insurance on something like a cellphone is because you expect you will break it.  You are going to end up paying for an entire additional phone over time anyway and most such policies stop paying out after the first replacement anyway. The reason why people buy the coverage anyway, even when it really isn't in their best interest is due to two factors: being risk averse, as base64 pointed out, and also being generally bad at dealing with large numbers.  On the risk averse side, they think of how much they are spending on the item (even if it is less compared to large items like cars or houses) and don't want to lose that.  On the bad at dealing with large numbers side, they don't think about the overall cost of the coverage and don't read the fine print as to what they are actually getting coverage for.  (This is the same reason that you always see prices one cent under the dollar.)   People often don't really subconsciously get that they are paying more even if they would be able to eat the loss, so they pay what feels like a small amount to offset a large risk.  The risk of loss is a higher fear than the known small, easy payment that keeps the risk away and the overall value proposition isn't even considered. "For simplicity, let's start by just considering cash back. In general, cash back from credit cards for personal use is not taxable, but for business use it is taxable (sort of, I'll explain later). The reason is most personal purchases are made with after tax dollars; you typically aren't deducting the cost of what you purchased from your personal income, so if you purchase something that costs $100 and you receive $2 back from the CC company, effectively you have paid $98 for that item but that wouldn't affect your tax bill. However, since businesses typically deduct most expenses, that same $100 deduction would have only been a $98 deduction for business tax purposes, so in this case the $2 should be accounted for. Note, you should not consider that $2 as income though; that would artificially inflate your revenue. It should be treated as a negative expense, similar to how you would handle returning an item you purchased and receiving a CC refund. Now for your specific questions: Part 1: As a small business owner, I wish to attend an annual seminar to improve my business. I have enough credit card reward points to cover the airfare, hotel, and rental car. Will those expenses still be deductible at the value displayed on the receipt? Effectively no, these expenses are not deductible. If you deduct them they will be completely counter-acted by the ""refund"" you receive for the payments. Part 2: Does it matter if those points are accrued on my personal credit card, rather than a business credit card? This is where it gets hairy. Suppose your company policy is that employees make purchases with their own personal credit cards and submit receipts for reimbursement. In this case the employer can simply reimburse and would not know or care if the employee is racking up rewards/points/cashback. The trick is, as the employee, you must always purchase business related items normally so you have receipts to show, and if you receive cashback on the side there seems to be a ""don't ask, don't tell"" rule that the IRS is OK with. It works the same way with heavy business travelers and airline miles- the free vacations those users get as perks are not treated as taxable income. However, I would not go out of my way to abuse this ""loophole"". Typically, things like travel (airfare, hotel, car rental, meals) are expected. But I wouldn't go purchase 100 company laptops on your personal card and ask the company to reimburse you. The company should purchase those 100 laptops on a company card and effectively reduce the sale price by the cashback received. (Or more realistically, negotiate a better discount with your account rep and just cut them a check.) Part 3: Would there be any difference between credit card points and brand-loyalty points? If the rental car were paid for with points earned directly on the rental car company's loyalty system (not a CC), would that yield a different result? There is no difference. Perhaps the simplest way to think about this is you can only deduct an expense that you actually incur. In other words, the expense should show up on a bank or CC statement. This is why when you volunteer and work 10 hours for a charity, you can't call that a ""donation"" of any amount of money because there is no actual payment made that would show up on a bank statement. Instead you could have billed the charity for your 10 hours of work, and then turned around and donated that same amount back to them, but it ends up being a wash." "I mean, I'd say ""no shit"". The model is easy to reproduce (see the inverse model proposed by CHX and the new NYSE American), and people don't have a real incentive to trade there. IEX's main selling point to the buy side was the reduced price impact order router, which ultimately went away when they became an exchange.  Listings could be interesting, but I can't see why any company that doesn't have some sort of statement to make would want to list there versus the big two, or BATS. Hell, even BATS, a much more established market, has had a hard time drawing listings.  I'm glad they've seen a small bump in market share in the last few months, but I can't see them becoming one of the big three players any time soon (especially after having shat all over the industry during their launch period).  Side note: The UTP SIP (and soon the CTA SIP) are both **much** faster than when IEX went live. Turns out inside updates via the SIP are received faster than the prop market data feed, and faster than updates received over an order entry connection. Under these circumstances the street knows a trade occurred before the participants in the trade. This information asymmetry often results in market makers getting run the hell over, and makes them less likely to quote at the inside on your market." There is the underpayment penalty, and of course the general risk of any balloon-style loan. While you think that you have enough self-discipline, you never know what may happen that may prevent you from having enough cash at hands to pay the accumulated tax at the end of the year. If you try to do more risky investments (trying to maximize the opportunity) you may lose some of the money, or have some other kind of emergency that may preempt the tax payment. Most countries tax income in its various ways, but not moving money. If this is a movement of already owned money, it is not tax-relevant. If it is a payment for services done, it is income, and it is the recipient's duty to pay taxes on it. Note that transferring large amounts of money (10k+) between countries can trigger a review, which - worst case - results in questions where it came from. The point of that is solely to verify it was legally earned money (not drug money or such). There is nothing to worry about if the money was legally earned. "It's also worth thinking about minor ""emergencies"" when the location of your cash may be more important than the amount. I keep a baggie of change and small bills in my glovebox for meters and tolls. I keep a ten dollar bill in my armband when I go out for a jog or bike. Those little stashes have saved me more than once. Zombie apocalypse money? I just have a couple hundred at home." Q: If I call a tail a leg, then how many legs does a dog have?   A: 4. You can call it whatever you want, it's still a tail. The scenario is nonsense. There is a quid pro quo, the waitress served the customer and he tipped her. A $7 tip on a $24.47 check. He was generous, but misguided if he thought that this note would let the tip go untaxed.  And even though the article you link is fresh, the author has the gift threshold incorrect. This year it's $14,000, and has been so since 2013.  A cute story, and unlikely to be an issue for $7, but the IRS would take notice if this idea gained any traction.  Two references - If Gifts Are Not Income, Why Tax Gratuities? From the Tax Court Files: Is That Money a Gift or Income?