Do I need to keep paper records for my business?
Scanned or electronic copies of invoices should be sufficient as long as they are accurate and you can deliver them during an audit. Also, if you have an accountant prepare your taxes you would either need to provide them a copy of the invoices or a summary of them with the corresponding amounts to be claimed. Personally I prefer to print out a paper copy and file that away with that quarter's and year's other tax documents. I do my own taxes and find paper copies handy as I can go through each invoice/receipt and make sure I have entered its information by ticking it. I find that when handling a large number of documents that paper copies are more easy to handle than electronic ones. In the end you will need to use a system that you feel comfortable with and are able to use effectively.
I would suggest at least getting a personal card that you only use for business expenses, even if you don't opt for a business card.  It makes it very clear that expenses on that card are business expenses, and is just more professional.  The same goes for a checking account, if you have one of those.  It makes it easier to defend if you are ever audited, and if you use an accountant or tax preparer. Based on the additional comment you gave, I would recommend that you keep the capital from the businesses separate as much as possible.  It sounds like you won't get into any trouble legally if you make 'loans' or transfers of capital from one business into the other. But I would suggest that you keep detailed records of any transfers that you do make.  The reason why is that in any business, it is important to know the economics of how your business makes money. If you find yourself making transfers repeatedly, then your business model may be bad. Even if your transfers are only to deal with the cost of poor customers, it could still mean that your business model needs to be adjusted.  But if it's a question of the timing of cash flows, then there's really nothing wrong with taking some of the money from your successful pants operation and building up more working capital in your stationery shop. In general, you don't need to keep bills around for more than a few months.  The exceptions are: anything that was itemized on your federal or state income taxes. You want to keep these around for seven years in case of an audit by the IRS brokerage statements buying/selling stocks, bonds, mutual funds, etc.  You need to know how much you bought a stock for when you sell it, to calculate capital gains. information relating to major renovations to your house.  This can be used to reduce the gain when you sell. anything relating to a business, again for tax and valuation purposes. When selling a house, the last years worth of utility bills might be useful, to show potential buyers. However, I get almost all of my recurring bills electronically now.  They get saved and backed up.  In that case, its easier to just keep everything than to selectively delete stuff.  It takes very little space, is easier to find things than in paper files, and is much less hassle when moving than boxes full of paper. "Since this is a cooperative I'm guessing your partners may want to be able to view the books so another key point you may want to consider is collaboration.  QuickBooks desktop has all of these same issues because it is meant to be used on a single desktop. We're in an age of mobile devices, and especially in a business like landscaping it would be nice if certain aspects of record keeping could be done at the point and time where they are incurred.  I'd argue you want a Software as a Service (SaaS) accounting package as opposed to ""accounting software"" which might come on a CD in the form of QuickBooks, Sage and others. Additionally, most of these will also have guides to help make sure you are properly entering your records. Most of these SaaS products also have customer success teams to help you along should you need assistance. Depending on the level of your subscription you may get more sophisticated handling of taxes, customized invoices or integrated payroll. Your goal is to keep accurate records so you can better run your business and maintain obligations like filing taxes. You're not keeping the records just to have them. Keep them in a place where they will work for you and provide the insights and functionality that will help your business grow and become successful. Accounting software will always win in this scenario over a spreadsheet. FULL DISCLAIMER: I work for Kashoo, a simple cloud accounting product designed for small businesses. But the points I mention above are true for Xero, QuickBooks Online and Wave as well as Kashoo. And if you really want expertise to go with the actual software consider service providers with a platform like: Indinero, Bench, easyrecordbooks or Liberty Accounting." I'd imagine you want to keep the utility bills around to dispute any historical billing errors or anomalies for perhaps 6 months to a year. Beyond that, you always have the financial records of making the payments -- namely, your bank statements. So what benefit is there in keeping the paper receipts for utility payments around for longer than that? I say shred them, with extreme prejudice -- while wearing black Chuck Norris style. Regarding your specific types: If you can't part with anything, sure, scan them. Also, there are lots of opportunities to sign up for eStatements with just about any financial provider.  They want you to sign up for them, because it reduces their expenses. If you still like having paper around (I do admit that it's comforting in a way) then you can usually prune your paper a bit by statement (getting rid of T&C boilerplate, advertisements, etc.) or by consolidation (toss monthly when the quarterly consolidation statement arrives; toss the quarterly when the yearly arrives). While it's wise, easier and safer to check your transactions online a few times a month, I opt to receive and file paper statements as a hard copy back up of account history. Any reconciliation I perform is a quick glance to make sure the numbers sound right. It's probably a small waste of time and space, but it settles some of my paranoia (due to my training as a computer engineer)  about failure of electronic banking systems. If someone tampers with bank records or a SAN explodes and wipes out a bunch of account data, then I will have years worth of paper statements to back up my numbers.  Having years worth of statements printed on the banks stationary will have better credibility in court than a .pdf or printout thereof that could have been doctored, in case I ever needed to take my bank to court. A little piece of mind for the price of a letter opener, a square foot file box and a couple of minutes a month. First - get a professional tax consultation with a NY-licensed CPA or EA. At what point do I need to worry about collecting sales taxes for the city and state of New York? Generally, from the beginning. See here for more information on NYS sales tax.  At what point do I need to worry about record-keeping to report the income on my own taxes? From the beginning. Even before that, since you need the records to calculate the costs of production and expenses. I suggest starting recording everything, as soon as possible. What sort of business structures should I research if I want to   formalize this as less of a hobby and more of a business? You don't have to have a business structure, you can do it as a sole proprietor. If you're doing it for-profit - I suggest treating it as a business, and reporting it on your taxes as a business (Schedule C), so that you could deduct the initial losses. But the tax authorities don't like business that keep losing money, so if you're not expecting any profit in the next 3-4 years - keep it reported as a hobby (Misc income). Talk to a licensed tax professional about the differences in tax treatment and reporting. You will still be taxed on your income, and will still be liable for sales tax, whether you treat it as a hobby or as a business. Official business (for-profit activity) will require additional licenses and fees, hobby (not-for-profit activity) might not. Check with the local authorities (city/county/State). In this blog, i will share some important things about QuickBooks Online. In this busy life, Every businessman has limited time. So with the help of QuickBooks Online he/she has to keep a track record of their sales and expenses. For more - https://www.wizxpert.com/quickbooks-online-support/ "What exactly would the financial institution need to see to make them   comfortable with these regulations The LLC Operating Agreement. The OA should specify the member's allocation of equity, assets, income and loss, and of course - managerial powers and signature authorities. In your case - it should say that the LLC is single-member entity and the single member has all the managerial powers and authorities - what is called ""member-managed"". Every LLC is required to have an operating agreement, although you don't necessarily have to file it with the State or record it. If you don't have your own OA, default rules will apply, depending on your State law. However, the bank will probably not take you as a customer without an explicit OA." When a business asks me to make out a cheque to a person rather than the business name, I take that as a red flag. Frankly it usually means that the person doesn't want the money going through their business account for some reason - probably tax evasion. I'm not saying you are doing that, but it is a frequent issue. If the company makes the cheque out to a person they may run the risk of being party to fraud. Worse still they only have your word for it that you actually own the company, and aren't ripping off your employer by pocketing their payment. Even worse, when the company is audited and finds that cheque, the person who wrote it will have to justify and document why they made it out to you or risk being charged with embezzlement. It's very much in their interests to make the cheque out to the company they did business with. Given that, you should really have an account in the name of your business. It's going to make your life much simpler in the long run. Starting and running a business in the US is actually a lot less complicated than most people think. You mention incorporation, but a corporation (or even an S-Corp) isn't generally the best entity to start a business with . Most likely you are going to want to form an LLC instead this will provide you with liability protection while minimizing your paperwork and taxes. The cost for maintaining an LLC is relatively cheap $50-$1000 a year depending on your state and you can file the paperwork to form it yourself or pay an attorney to do it for you. Generally I would avoid the snake oil salesman that pitch specific out of state LLCs (Nevada, Delaware etc..) unless you have a specific reason or intend on doing business in the state.  With the LLC or a Corporation you need to make sure you maintain separate finances. If you use the LLC funds to pay personal expenses you run the risk of loosing the liability protection afforded by the LLC (piercing the corporate veil). With a single member LLC you can file as a pass through entity and your LLC income would pass through to your federal return and taxes aren't any more complicated than putting your business income on your personal return like you do now. If you have employees things get more complex and it is really easiest to use a payroll service to process state and federal tax with holding.  Once your business picks up you will want to file quarterly tax payments in order to avoid an under payment penalty.  Generally, most taxpayers will avoid the under payment penalty if they owe less than $1,000 in tax after subtracting their withholdings and credits, or if they paid at least 90% of the tax for the current year, or 100% of the tax shown on the return for the prior year, whichever is smaller. Even if you get hit by the penalty it is only 10% of the amount of tax you didn't pay in time. If you are selling a service such writing one off projects you should be able to avoid having to collect and remit sales tax, but this is going to be very state specific. If you are selling software you will have to deal with sales tax assuming your state has a sales tax. One more thing to look at is some cities require a business license in order to operate a business within city limits so it would also be a good idea to check with your city to find out if you need a business license. "Some benefits of having a business checking account (versus a personal checking account) are: The first 3 should be pretty easy to determine if they are important to you. #4 is a little more abstract, though I see you have an LLC taxed as a sole proprietorship, and so I'm guessing protecting your personal assets may have been one of the driving reasons you formed the LLC in the first place. If so, ""following through"" with the business account is advised." I am in the United States. There is no need to keep the statements in any form forever. Once the bank gives you a 1099 stating how much interest you have earned, you don't need to keep them. If you only have them in electronic form, that is good enough for the IRS. When you do need to show a bank statement, such as when applying for a loan, the loan company will be keeping a copy. It doesn't matter if it was a scan from the original, from a printed PDF, or if you printed it from your archives. In the US they used send the original check back to the person who wrote it, so they could keep it for their records. Then many banks went to carbons, but if you paid extra they would send you the original. Now the bank that cashes the check scans the check and destroys the original. If you want a copy for your records it only exists as a scanned image. You don't need to keep receipts for most things, and if you are not going to itemize your deductions (which as a college student, you probably won't), you need even fewer.  Things that you should always keep: If you are itemizing your deductions, you want to keep receipts for anything that you can itemize.  Some common things are: Another thing that you should do, but few people do, is keep track of your online purchases, since many states require you to pay sales tax on those purchases.  Of course, the state has no way of knowing what you buy online, so it is all done on the honor system.