Moonlighting as a software developer: employee or independent contractor w/ LLC?
"I've been in a similar situation before. While contracting, sometimes the recruiting agency would allow me to choose between being a W2 employee or invoicing them via Corp-2-Corp. I already had a company set up (S-Corp) but the considerations are similar. Typically the C2C rate was higher than the W2 rate, to account for the extra 7.65% FICA taxes and insurance. But there were a few times where the rate offered was identical, and I still choose C2C because it enabled me to deduct many of my business expenses that I wouldn't have otherwise been able to deduct. In my case the deductions turned out to be greater than the FICA savings. Your case is slightly different than mine though in that I already had the company set up so my company related costs were ""sunk"" as far as my decision was concerned. For you though, the yearly costs associated with running the business must be factored in. For example, suppose the following: Due to these expenses you need to make up $3413 in tax deductions due to the LLC. If your effective tax rate on the extra income is 30%, then your break even point is approximately $8K in deductions (.3*(x+3413)=3413 => x = $7963) So with those made up numbers, if you have at least $8K in legitimate additional business expenses then it would make sense to form an LLC. Otherwise you'd be better off as a W2. Other considerations:"
As a new (very!) small business, the IRS has lots of advice and information for you. Start at https://www.irs.gov/businesses/small-businesses-self-employed and be sure you have several pots of coffee or other appropriate aid against somnolence.  By default a single-member LLC is 'disregarded' for tax purposes (at least for Federal, and generally states follow Federal although I don't know Mass. specifically), although it does have other effects. If you go this route you simply include the business income and expenses on Schedule C as part of your individual return on 1040, and the net SE income is included along with your other income (if any) in computing your tax. TurboTax or similar software should handle this for you, although you may need a premium version that costs a little more.  You can 'elect' to have the LLC taxed as a corporation by filing form 8832, see https://www.irs.gov/businesses/small-businesses-self-employed/limited-liability-company-llc . In principle you are supposed to do this when the entity is 'formed', but in practice AIUI if you do it by the end of the year they won't care at all, and if you do it after the end of the year but before or with your first affected return you qualify for automatic 'relief'. However, deciding how to divide the business income/profits into 'reasonable pay' to yourself versus 'dividends' is more complicated, and filling out corporation tax returns in addition to your individual return (which is still required) is more work, in addition to the work and cost of filing and reporting the LLC itself to your state of choice. Unless/until you make something like $50k-100k a year this probably isn't worth it. 1099 Reporting. Stripe qualifies as a 'payment network' and under a recent law payment networks must annually report to IRS (and copy to you) on form 1099-K if your account exceeds certain thresholds; see https://support.stripe.com/questions/will-i-receive-a-1099-k-and-what-do-i-do-with-it  . Note you are still legally required to report and pay tax on your SE income even if you aren't covered by 1099-K (or other) reporting. Self-employment tax. As a self-employed person (if the LLC is disregarded) you have to pay 'SE' tax that is effectively equivalent to the 'FICA' taxes that would be paid by your employer and you as an employee combined. This is 12.4% for Social Security unless/until your total earned income exceeds a cap (for 2017 $127,200, adjusted yearly for inflation), and 2.9% for Medicare with no limit (plus 'Additional Medicare' tax if you exceed a higher threshold and it isn't 'repealed and replaced'). If the LLC elects corporation status it has to pay you reasonable wages for your services, and withhold+pay FICA on those wages like any other employer. Estimated payments. You are required to pay most of your individual income tax, and SE tax if applicable, during the year (generally 90% of your tax or your tax minus $1,000 whichever is less). Most wage-earners don't notice this because it happens automatically through payroll withholding, but as self-employed you are responsible for making sufficient and timely estimated payments, and will owe a penalty if you don't. However, since this is your first year you may have a 'safe harbor'; if you also have income from an employer (reported on W-2, with withholding) and that withholding is sufficent to pay last year's tax, then you are exempt from the 'underpayment' penalty for this year.  If you elect corporation status then the corporation (which is really just you) must always make timely payments of withheld amounts, according to one of several different schedules that may apply depending on the amounts; I believe it also must make estimated payments for its own liability, if any, but I'm not familiar with that part. "Note: Specific to UK. I can't recommend anything higher than Crunch - they act as your accountant and have their own cloud accounting software, so it's more expensive than just using cloud accounting software, but if you use an accountant to do your year-end anyway, then they cost about the same as using cloud accounting software plus using an accountant to do your year-end. The thing I like (as a software development contractor) is that I don't have to know or worry about different ledger accounts, or journal entries, or any of the other weird accounting things, etc. Most cloud accounting software claim to simplify accounting ""so that you can concentrate on running your business"" whereas the reality is that you still have to spend ages learning how to be an accountant just to fill it in correctly. With Crunch that's actually true, it does actually make it simple. I've used Crunch, Sage, and Xero, so my sample-set isn't very big - just thought I'd share my experiences. If you value your time and get annoyed by having to create multiple internal transfers between different ledgers just to do something simple, it's for you. This probably sounds like a sales pitch, but I have nothing to do with them and nothing to gain by recommending them. The only reason I'm so passionate is I started a new business to do an online shop and tried to use Crunch, but they don't do retail businesses. Only contractors/freelancers or simple service-based businesses (their software is geared up specifically for that which I guess is why it's more simple than the others). Anyway, so now I'm annoyed at having to use the more complicated ones." Successful technology contractors* make far more than employees. The contractor market is getting oversaturated because more people want to do it and employers like it less and less. Problem is, the only time big employers are willing to hire contractors are when they're really good, so you really only get well paid contractors who find consistent work, and then a flood of contractors that have to get whatever work they can find. As the offshore planning world turns, the limited liability company (“LLC”) is starting to appear with greater frequency as an alternative to the conventional offshore asset protection trust.  It is desirable because unlike the offshore trust, which requires an independent trustee, the LLC permits the client to remain in full control as the Manager of the entity.  While the typical offshore trust provides the highest form of asset protection, the asset protection afforded by the LLC is significant, and with retained control, provides a powerful combination.  Recently, St. Vincent and the Grenadines as well as Nevis, have sought to improve their legislation by offering superior LLC statutes.  Each is progressive and will be desirable for planners and clients alike. "Yea. Almost every form I fill out wants to know ""Employer Name"". They don't even bother checking ""Are you Self Employed"". Of course, I end up writing ""Self Employed"" in employer name field anyway.   In the United States, it is even harder because EVERY state has their own labor and employment laws. You are a freelancer but what if you need to travel to a client site in a different state. Bam, you gotta file taxes for that state as well even if you made like a few hundred bucks.   Too much red tape and it is really hard to change." What is the corporate structure? Your partnership agreement or LLC operating agreement should dictate how you approach this. One possibility that I use: I set up an LLC and get paid through that entity. Then I set up a payroll service through Bank of America and set up direct deposit so that it is free.  I pay myself at 70% of my hourly rate based on the number of hours I work, and the payroll service does all the calculations for me and sets up the payments to the IRS.  Typically money is left over in my business account. When tax time rolls around, I have a W2 from my LLC and a 1099 from the company I work for. I put the W2 into my personal income, and for the business  I enter the revenue on the 1099 and the payroll expenses from paying myself; the left over in the business account is taxed as ordinary income. Maybe it's overkill, but setting up the LLC makes it possible to (a) set up a solo 401(k) and put up to $51k away tax-free, and (b) I can write off business expenses more easily. In general  What does this mean? Assume 10 holidays and 2 weeks of vacation. So you will report to the office for 240 days (48 weeks * 5 days a week).  If you are a w2 they will pay you for 260 days (52 weeks * 5 days a week). At $48 per hour you will be paid: 260*8*48 or $99,840. As a 1099 you will be paid 240*8*50 or 96,000. But you still have to cover insurance, the extra part of social security, and your retirement through an IRA. A rule of thumb I have seen with government contracting is that If the employee thinks that they make X,000 per year the company has to bill X/hour to pay for wages, benefits, overhead and profit. If the employee thinks they make x/hour the company has to bill at 2X/hour. When does a small spread make sense: The insurance is covered by another source, your spouse; or government/military retirement program.  Still $2 per hour won't cover the 6.2%  for social security. Let alone the other benefits. The IRS has a checklist to make sure that a 1099 is really a 1099, not just a way for the employer to shift the costs onto the individual.