Bookkeeping for a Small Business in Westport, CT: Where to Start

The short answer

Most setups start with a business bank account, a choice between cash and accrual, and a record system, all before the first invoice goes out. Then come the Connecticut registrations that fit what you sell, and two Westport filings: a trade name certificate, if you use one, and a personal property declaration every autumn. This is an overview of what each agency publishes; talk the method and the registrations through with your own tax preparer before you file anything.

A consultant billing from a home office near Saugatuck and a shop on Main Street share most of this list. They may part ways at sales tax: the shop selling goods needs a permit, and the consultant needs one too if the service they sell is taxable.

The rules below are as each agency publishes them, checked in November 2026.

What do you set up first?

Why a separate account comes first

Because everything else is built from it. IRS Publication 583 says one of the first things to do when you start a business is open a business checking account and keep it separate from your personal one. It calls the business checkbook your basic source for recording expenses, says to deposit all daily receipts into it, and says to reconcile it each month.

Cash or accrual?

Cash is the common starting point. IRS Publication 538 says most individuals and many small businesses use the cash method, where you generally report income when you receive it and deduct expenses when you pay them. Under accrual, you report income when you earn it and expenses when you incur them, regardless of when the money moves.

The same publication says you choose your method when you file your first return, and you generally need IRS approval to change it later. It also says that if you produce, buy or sell merchandise, you generally must keep an inventory and use accrual for those sales and purchases, with exceptions for small business taxpayers. A retailer should settle this question before the first return, not after.

What record system is enough?

A simple one, if it shows both sides. The IRS page on what records to keep says you may choose any recordkeeping system suited to your business that clearly shows your income and expenses.

Which Connecticut registrations does a new business need?

It depends on what you sell. The DRS registration page says you register on myconneCT for each business and tax type to get a Connecticut Tax Registration Number, and that some tax types carry a registration fee.

Sales tax deserves the closest read, because it applies to some businesses and not others. The same DRS registration page says you need a Sales and Use Tax Permit if you sell, rent or lease goods, sell a taxable service, or run a hotel, motel, lodging house or bed and breakfast, and that you must get it before making any sales, whatever the number of sales or the tax collected. It also says a seller is liable for the tax whether or not it was collected from customers. Every building contractor, including subcontractors, needs one before providing any services, even untaxed ones. The rules don't apply to casual or isolated sales, which DRS describes as infrequent sales of a nonrecurring nature by someone not in the business of selling. Whether a service is taxable is a question for DRS guidance or your tax preparer.

For the books, that means sales tax collected is tracked in its own account as money owed to the state.

What does Westport add to the list?

The trade name certificate

If you trade under a name other than your own, or other than the name your company registered with the state, that's a trade name. The state business portal's trade names page says it's filed with the town clerk where the business is mainly transacted, in one town only. It also says a trade name gives no liability protection and doesn't replace a permit. In Westport, the Town Clerk's office records them, and its trade name certificates page lists the filing, notary and copy charges.

The personal property declaration, every November

This one has a fixed date and a penalty. Section 12-41 of the Connecticut General Statutes says anyone who fails to file a declaration of personal property by November 1, or by an extended date the assessor grants, faces a penalty of 25% of the assessment of that property. The state's 2026 declaration form from the Office of Policy and Management adds that when November 1 falls on a Saturday or Sunday, the declaration may be filed the next business day, which made the 2026 deadline Monday, November 2. The Westport Assessor's Office page takes declarations online.

Your books make this easier or harder. A fixed asset list kept as you buy the desk, the laptops and the printer gives you the starting figures, though the form still asks for more, so read the current one each year.

Should you do the books yourself?

Often, at the start. A new business with one account, a handful of invoices and no staff can keep its own books if the month gets reconciled. The table below is a rough guide to when that stops holding.

A bookkeeping firm's guide to when an owner should stop doing their own books names three signs, being months behind on reconciliations, one account for the business and the household, and a request for statements you can't answer.

If you're already months behind, our post on how catch-up bookkeeping works covers getting current. A first hire has its own setup list, covered in our first employee payroll setup guide.

Where we fit in

We set up and keep bookkeeping for small businesses, including QuickBooks Online setup, monthly reporting and catch-up work, from our office at 77 Canoe Brook Rd in Trumbull. We work with small businesses across Connecticut and the rest of the United States, and our Westport bookkeeping and tax page lists what we cover there.