Can a company donate to a non-profit to pay for services arranged for before hand?
Donations need to be with no strings attached. In this case, you make the cash donation, a deduction, and then they pay you, in taxable income. It's a wash. Why not just give them the service for free? Otherwise this is just money going back and forth. "When you say ""donate"", it usually assumes charitable donation with, in this context, tax benefit. That is not what happens in your scenario. Giving someone money with the requirement of that someone to spend that money at your shop is not donation. It is a grant. You can do that, but you won't be able to deduct this as charitable donation, but the money paid to you back would be taxable income to you. I respectfully disagree with Joe that its a wash. It is not. You give them money that you cannot deduct as an expense (as it is not business expense) or donation (as strings are attached). But you do give them the money, it is no longer yours. When they use the money to pay you back - that same money becomes your taxable income. End result: you provide service, and you're the one paying (taxes) for it. Why would you do that?" "Can a company say ""StackExchange"" donate to a non-profit company say $5,000 in agreement that they will spend that on paying a designer for a new website? And most importantly is this donation still tax deductible? A non-profit would have to typically create a bucket for IT Services or Website design. As long as ""StackExchange"" specify they employ a profession service to get it done, there would be no issue. If ""StackExchange"" were to specify an individula/company it would be an issue." People put conditions on donations all the time. They donate to the Red Cross for a specific disaster. The donate money to a church for the building fund. They donate money to a hospital to buy a new x-ray machine. They donate money to the scouts for a new dining hall.  It is possible to donate money to a non-profit for a specific purpose. If the non-profit doesn't want to accept the money with those strings they can refuse. Generally these specific projects are initiated by the non-profit. But there is no requirement that the idea originate with the non-profit.  It is also up to the non-profit and their legal advisers regarding how strictly they view those strings. If you donate money for web design and they don't spend it all, can they pay net years hosting bill with the money, or must they hold it for a few years for when they need a designer again? If the company wants to provide the service, they can structure the project to pay their employees for their time. They pay employees for $100 of labor while deigning the website. The pay and benefits reduce profit thus lowering taxes.  Donating money to the non-profit to be given back to the company doesn't seem to be the best way to structure transaction. At best it is a wash.  Donating money to a charity and then directing exactly which contractor will perform the service starts to look like money laundering, and most charities will get wary.
It's a good question. We can't know for sure, but here are some things to think about. Paypal advertises a discounted transaction rate for non-profit organizations.  In the U.S. at least, the rate they advertise is 2.2% + 0.30 USD.  There are lots of things that can come into play here, such as international rates or any special deal that Wikimedia has struck with Paypal, but it seems reasonable to guess that of your 2€ donation, Wikipedia sees perhaps 1.65€.  Note that most of the fee is a flat rate; of the next 2€ in your donation, Wikipedia gets 1.96€. Direct debit probably has lower fees.  Paypal has to account for some credit card transaction fees in their fee structure, and direct debit does not.  Therefore, I would guess that to maximize your gift, direct debit might result a little better than Paypal.   Charities, in general, don't want to tell you the best way to donate, because they want it to be as easy for you as possible, and don't want to discourage any type of donation at all.  They are very happy to get any donation, even if one method over another results in slightly higher fees.  Wikimedia, in particular, offers many different options for donating. Apart from what the other posters have said, you could look at some 'good cause'. I'd keep on saving 50% as spending more won't really make you more happy. You already sound happy. What I used to do, when I could, was to donate 10% of my 'profit' per year. I'd compare year start with year end and do the math. Afterwards it was just a matter of choosing. there are non government organizations that will get most money where it's needed. Edit as soon as the business I'm starting becomes profitable, I'll continue my donations. Thanks for the appreciations. Gaining traction is your first priority. WARNING: as @JosephZambrano explains in his answer the tax penalty for withdrawing from a 401(k) can easily exceed the APR of the credit card making it a very bad strategy. Consult in-depth with a financial advisor to see before taking that path.  As @JoeTaxpayer has noted a loan is another alternative. The 401k is no good to you if you can't have shelter or comfort in the mean time.  The idea is to look at all the money as a single thing and balance it together.  There is no credit and retirement, just a single target that you can hit by moving the good money to clear the bad. Consolidating the credit card debt somehow would be very wise if you can.  Assuming it is 30% APR shrinking that quickly is the first priority. You may be able to justify a hardship withdrawal to finance the reduction/consolidation of the credit card.  It may be worth considering negotiating a closure arrangement with a reduced principal.  Credit card companies can be quite open to this as it gets their money back. You may also be able to negotiate a lower interest rate. You may be able to negotiate a non-credit-affecting debt consolidation with a debt consolidator.  They want to make money and a 25K loan to a person with sound credit is a pretty good bet. Moving, buying a house, or any of that may just relocate the problem.   You may be able to withdraw $25K from your 401k under hardship, pay the credit card, and come up with a payment plan for the medical debt. It's a retirement setback for sure, but retirement is an illusion with that credit card shark eating all of your hard-earned money.  You gotta slay that beast quick. Again, be sure to fully analyze whether the penalty on the 401(k) withdrawal exceeds the APR of the credit card. It is important to understand that when or before you received services from your medical provider(s), you almost certainly signed a document stating that you understand that you are fully responsible for the entire bill, even though the provider  may be willing to bill the insurer on your behalf as a service. In almost all cases, this is the arrangement, so it is very unlikely that you will be able to dispute the validity of the bill, since you did receive the service and almost certainly agreed to be fully responsible for the payments. With regard to the discounts, your medical provides have likely contracted with your insurer to provide services at a certain price or discount level, so I would base all of your negotiations with the providers and/or the collectors on those amounts. They can't legitimately bill you for the full amount since you are insured by a company they have a contract with, and you are not self-pay/uninsured, and the fact that they haven't been paid by your insurer doesn't change that, because the discount likely depends on the contact they have with your insurer and not whether or not they are billed/paid by your insurer. Please note - this is a common arrangement, but I'd recommend that you verify this with your insurer. Unfortunately, payment in 90+ days is often typical by insurance standards, so it's not yet clear to me whether or not your insurer has broken any laws such as a Prompt Pay law, or violated the terms of your policy with them (read it!). However, you need to find out which claims rep/adjuster is handling your claims and follow up with them until the payments are made. It's not personal, so make this person's life miserable until it is done and call them so often that they know it's you by the caller ID. I would also recommend contacting the collector(s), and letting them know that you don't have the money and so will not be able to pay, provide them with copies of the EOBs that state that the insurance company plans to pay the providers, and then ignore their calls/letters until the payments are made. When they call, simply reiterate that you don't have the money and that your insurance company is in the process of paying the bills. You have to expect that you will be dealing with a low-paid employee that is following a script. You are just the next person on their robo-call list, and they are not going to understand that you don't have a pile of money laying around with which to pay them, even if you tell them repeatedly. Make sure that you at no point give them access to any of your financial accounts, such as a checking or savings account, or a debit card - they will access it and clean you out. It is likely that your insurance provider will pay the providers directly since they were likely billed by the providers originally. If the providers have sold the debt to the collectors (and are not just employing a collector for debt they still own), you may have to follow up with the providers as well and make sure that the collection activity stops, since the providers may also need to forward the payments to the collectors once they are paid by the insurance company. Of course, if the insurer refuses to pay the claims, at that point I would recommend meeting with a lawyer to seek to force them to pay. "I'll assume United States as the country; the answer may (probably does) vary somewhat if this is not correct.  Also, I preface this with the caveat that I am neither a lawyer nor an accountant.  However, this is my understanding: You must recognize the revenue at the time the credits are purchased (when money changes hands), and charge sales tax on the full amount at that time.  This is because the customer has pre-paid and purchased a service (i.e. the ""credits"", which are units of time available in the application).  This is clearly a complete transaction.  The use of the credits is irrelevant.  This is equivalent to a customer purchasing a box of widgets for future delivery; the payment is made and the widgets are available but have simply not been shipped (and therefore used).  This mirrors many online service providers (say, NetFlix) in business model.   This is different from the case in which a customer purchases a ""gift card"" or ""reloadable debit card"".  In this case, sales tax is NOT collected (because this is technically not a purchase).  Revenue is also not booked at this time.  Instead, the revenue is booked when the gift card's balance is used to pay for a good or service, and at that time the tax is collected (usually from the funds on the card).  To do otherwise would greatly complicate the tax basis (suppose the gift card is used in a different state or county, where sales tax is charged differently?  Suppose the gift card is used to purchase a tax-exempt item?)  For justification, see bankruptcy consideration of the two cases.  In the former, the customer has ""ownership"" of an asset (the credits), which cannot be taken from him (although it might be unusable).  In the latter, the holder of the debit card is technically an unsecured creditor of the company - and is last in line if the company's assets are liquidated for repayment.   Consider also the case where the cost of the ""credits"" is increased part-way through the year (say, from $10 per credit to $20 per credit) or if a discount promotion is applied (buy 5 credits, get one free).  The customer has a ""tangible"" item (one credit) which gets the same functionality regardless of price.  This would be different if instead of ""credits"" you instead maintain an ""account"" where the user deposited $1000 and was billed for usage; in this case you fall back to the ""gift card"" scenario (but usage is charged at the current rate) and revenue is booked when the usage is purchased; similarly, tax is collected on the purchase of the service.  For this model to work, the ""credit"" would likely have to be refundable, and could not expire (see gift cards, above), and must be usable on a variety of ""services"".  You may have particular responsibility in the handling of this ""deposit"" as well." If the money awarded is sufficient to cover the cost of supporting their software, then you can at the time of entering the contract make a pledge of the money.   However if you need to prove that you have sufficient funds otherwise, you need to ask the organizers what they need, typically a Bank Statement showing the funds may be sufficient in the easiest possible condition, on the other extreme you may need to open an escrow account and deposit the money as safe keeping with the Bank and then produce that letter ... Depending on the country and Bank, certain Banks allow different passowrds for transactions and different for querying, so you can share the query password ... The company may not permit a transfer of these options. If they do permit it, you simply give him the money and he has them issue the options in your name.  As a non-public company, they may have a condition where an exiting employee has to buy the shares or let them expire.  If non-employees are allowed to own shares, you give him the money to exercise the options and he takes possession of the stock and transfers it to you.  Either way, it seems you really need a lawyer to handle this. Whenever this kind of money is in motion, get a lawyer.  By the way, the options are his. You mean he must purchase the shares, correct? "Note: I have no experience of attempting what is described below (neither am I a lawyer nor an accountant). The process may range from a ""small bureaucratic hurdle"" to a ""complex legal nightmare"". If it seems a plausible approach, you would probably be well-advised to reach out to others that have established CASCs for help and guidance. According to this HMRC page the two ways a body can claim Gift Aid is if either it is a recognised charity or if it is a Community Amateur Sports Club (CASC). So one option may be to try and establish a CASC. I suspect that this is unlikely to be an easy process, but may be a more likely approach than trying to get the council to establish a charity. The Register as a community amateur sports club (CASC) page on the HMRC site (very) briefly describes the steps; as you can see from their eligibility criteria, to register as a CASC, you would first have to create a ""Sports Club"" of some form that: has a formal constitution is open to the whole community and has affordable membership fees is on an amateur basis provides facilities in the UK is managed by ""fit and proper persons"" You would probably need the co-operation of the local council to allow the proposed sports club the use of the local park. One of the (several) requirements of becoming a CASC is that it must: So it could, in theory, be possible to spend money raised (through both membership fees and Gift-Aid-qualifying donations) on the improving the facilities of the park (tennis courts, bowling green etc.). However, note that How to Register page mentions (among many other requirements) the need to provide ""accounts from the last 12 months"" and ""bank statements from the last 3 months"". It doesn't (as far as I can see) explicitly state that the club must have been in existence for 12 months before applying for CASC status (it might be possible to send only what you have), but be aware that you may need to establish the club – and let it operate under its own steam – for a period before applying."