Tax planning and bookkeeping for business owners in Massachusetts and across the country

Only if the numbers clear two tests. First, profit has to be high enough that a reasonable salary for your work still leaves a meaningful amount to take as distributions, because self-employment tax on that slice is the entire saving. Second, the saving has to beat the cost of running payroll, filing a separate return and keeping cleaner books. Timing matters too. For a calendar-year business, an election filed by March 15 applies to this year, and a later one generally waits until next year. Run your own figures through the calculator on this page, then bring last year's return and we will test it properly.

As soon as you expect to owe $1,000 or more in federal tax after any withholding. Below that, the underpayment penalty generally does not apply. Above it, the IRS expects four payments through the year, in April, June, September and January, and charges a penalty when they fall short, even if you pay in full when you file. The safe route is to pay in a set share of last year's tax or of this year's, which is what the safe harbor rules allow. Massachusetts has its own, lower threshold. If you took distributions this year and paid nothing in, call before the next due date.

Yes, if the books do not reconcile. The test: if the bank balance in your software does not match the statement for the same date, you are not ready to file. A return prepared on top of that is a set of guesses. A guess that overstates income costs you money now, and a guess that understates it costs you later. Cleanup first also shortens the return, because nothing gets rebuilt in filing season. If the deadline is close, file an extension, fix the record, then file. Nobody here will judge the state of the books. Send the last reconciled month and the last filed return and we will tell you how far back it goes.

Not before you know what it is. Find the notice number in the corner and the response date, then resist two reflexes: paying the balance printed on the front because it is printed there, and leaving the envelope closed. Many notices are automated matching letters, not audits, and a short written reply with the right document settles them. A rushed reply can concede a point you would have won. As an Enrolled Agent, Mike Isaac is federally licensed to represent you before the IRS, so with a signed power of attorney the correspondence comes to us as well. Send a copy of the notice the day it arrives.

Monthly, once you have employees, inventory, a loan, or more than a handful of transactions a week. A year-end catch-up produces books that are good enough to file from and useless for running the business, because by the time you see the margin on a job it is nine months old. The test is simple: if you cannot say what last month's profit was, the books are too far behind to decide from. Monthly closes also catch errors while they are cheap. A missing deposit found this month is a phone call. If you are behind now, start with a cleanup, then move to a monthly close and stay there.

The first conversation is free, thirty minutes, by video or phone. Bring last year's business and personal returns, access to or an export from your accounting software, your most recent payroll reports if you have staff, and any notice you have received. We read the return for what was missed and the books for whether the return could have been right in the first place, then tell you what we see before you commit to anything. If the fit is wrong, we say so. Book a time online or call during business hours, which include Saturdays.

By the scope of the work, quoted in writing before anything starts. After the free consultation and a look at your return and books, you receive a written scope: what we will do, who does what, and the fee. What moves the fee is the number of entities and states, the condition of the books, and how much planning you want through the year. If something outside the scope comes up, we discuss it with you before we do it. The consultation itself is free, thirty minutes, with no obligation at the end of it. Fees begin only with the written scope.

The test is the decisions in front of you, not your revenue. Too small is rare. If a once-a-year return is genuinely all you need, we will say so. Too large is a question of scope, not size. Our founder prepared and reviewed returns for individuals, pass-through entities, corporations and nonprofits at one of the country's leading CPA firms, and that is the standard the work here is held to. We assess your entities, your states, the condition of the books and the deadlines before accepting an engagement. If a matter needs expertise outside our scope, we identify that early and tell you.

Yes. Clients from coast to coast work with us on the same monthly rhythm as the owner down the street: documents through a secure upload link, meetings by video or phone, signatures electronic. An Enrolled Agent is federally licensed to represent taxpayers before the IRS wherever they live, so IRS matters and federal returns run the same way in any state. State returns are a separate question. Massachusetts is home ground. Other states we confirm case by case before we take the work, and if a state requires something we do not hold, we say so and point you to someone who does.

It depends on what you sell, not where you sell it from. Massachusetts taxes sales of tangible goods and a short list of specific services, so if you sell products, including online to Massachusetts customers, you register with the Department of Revenue before the first sale and collect from then on. Meals tax applies to prepared food and drink, and many towns add a local option on top. Most pure services are not taxed. If you have been selling without registering, the fix is to register and file the open periods yourself before the state finds them. Bring your sales records and we will map the obligations.