Tax Planning and Advisory for Massachusetts Business Owners
For owners who learn what they owe on the day it is due. We build a projection from your actual books in the middle of the year, size the estimated payments to it, and put the decisions with a deadline attached in front of you while there is still time to act. For owners in Massachusetts and across the country.
Who this fits
A tax return is a report on decisions you already made. By the time it is prepared, the year is closed and most of the options are gone. Planning moves the conversation into the part of the year when you can still change the outcome.
It fits owners with profit that moves from year to year, owners taking distributions instead of wages, anyone with a large one-time event coming (a sale, a property, a buyout), and anyone whose entity has not been looked at since it was formed. It fits less well if what you want is the cheapest possible return and nothing else.
Most meaningful moves carry a deadline that has nothing to do with the filing date. An S corporation election has to be filed inside a window. A retirement plan has to exist before it can be funded. Equipment has to be placed in service, not only ordered. Miss the window and the answer is no, however good the idea was.
How the work runs
The projection is built from your books, not from last year's return plus a guess. A projection built on unreconciled books is fiction, so the first check is whether the books close every month, and if they do not, that is fixed before anything is forecast.
Mid-year is the default checkpoint, with a second pass in the fourth quarter while payroll runs remain. At each one we recalculate the estimate, apply the safe harbor, separate what you owe federally from what Massachusetts expects, and give you a monthly amount to set aside so the quarterly payment is not a shock.
Entity and owner pay are tested every year, not decided once. Where the numbers say an S corporation election is worth it, the modeling and the election itself run through our Entity Strategy work. Where the question is bigger than tax, a hire, a lease, a price change, borrowing, it moves into Controller & CFO Support, so cash and tax are looked at in the same conversation.
- A mid-year projection from actual books, refreshed in the fourth quarter
- Estimated payments set to the safe harbor and adjusted when the business moves
- Owner compensation, entity election and retirement plan reviewed before December closes the window
- Timing of equipment purchases and, for cash-basis businesses, of income and expenses across the year end
- The Massachusetts layer checked separately: conformity differences, the surtax and the pass-through entity election
What you get
A one-page projection showing where the year is heading and what the bill will be, federal and Massachusetts, on current facts. A payment schedule with dates and amounts. A short list of decisions, each with the deadline it carries and what it is worth.
Then a number you already knew about when the return is prepared, and cash set aside for it on purpose instead of found in a hurry.
Who leads it
Mike Isaac, EA, leads the work. Building tax projections and estimated payments for owners, and resolving the IRS and Massachusetts Department of Revenue notices that follow when nobody did, were part of his work as a senior accountant in business advisory at one of the country's leading CPA firms. He is an Enrolled Agent, federally licensed to represent taxpayers before the IRS. The projection and the return come out of the same file at the same firm, and the return is reviewed and signed by an Enrolled Agent.
If the immediate question is the S corporation election, run your own numbers on the calculator on the homepage first, then bring last year's return; the decision itself runs through Entity Strategy. Owners who want the forecast to go beyond tax, into cash, hiring and pricing, are usually better served by Controller & CFO Support.
What getting it wrong costs
Federal and Massachusetts income tax are pay-as-you-go systems. Employees handle this through withholding. Owners who take distributions have to send the money in themselves, four times a year, or pay an underpayment charge on top of the tax. The safe harbor rules remove that charge if you pay in a set share of last year's tax or this year's, but only if someone applies them on purpose.
The larger cost is not the penalty. It is the decision made without advice. Owner pay left at whatever it was, a retirement plan never set up, an equipment purchase made in the wrong year, an entity that stopped fitting three years ago. Each of those is cheap to fix in June and expensive or impossible to fix in March.
Massachusetts adds its own layer. The state does not follow every federal rule, applies a surtax on individual income above a set level, and offers an elective entity-level tax for eligible pass-through businesses that helps some owners and does nothing for others. Planning that only looks at the federal side produces a surprise on the state return.
What owners ask before this work starts.
How much should I be setting aside for taxes?
There is no single percentage that is right for everyone. It depends on your entity type, your profit, your other income, and your spouse's withholding if you file jointly. What we do instead is calculate it from your actual numbers and give you a monthly figure to move into a separate account. Then we recheck it as the year goes on, because a strong second half changes the answer.
Should my LLC elect to be taxed as an S corporation?
Sometimes. It can lower self-employment tax once profit is consistently above a certain level, because part of your income shifts from self-employment earnings to distributions. It also adds a separate business return, real payroll with real filings, and a requirement to pay yourself reasonable wages. We run the comparison on your own numbers first, because for a business that is not yet profitable enough, the added cost is bigger than the saving.
When should we start planning?
Earlier than most people do. Mid-year is a sensible default, since there is still time to adjust payroll, set up a plan, or change your estimates before the year closes. If something unusual is coming, such as selling the business or a property, call before it happens rather than after. Once a sale closes, most of the planning options are gone for good.
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03
Monthly Bookkeeping
For businesses whose books are close enough to file from but not good enough to decide from. Every account reconciled, a real month-end close, and statements you could hand a lender.
