Small Business Tax Problems: 7 Common Mistakes
Small Business Tax Problems: 7 Common Mistakes
Small Business Tax Problems: 7 Common Mistakes
Small business tax mistakes waste time and cost money. Plus, taxes are a complex topic that many, outside of industry professionals and tax specialists, struggle to understand. As a result, many business owners choose to ignore taxes altogether, not wanting to slow down or spend valuable resources on it.
They assume their energy would be better spent on operational topics. But many founders and business owners alike make the same couple of mistakes when it comes to taxes.
Here are 7 common tax mistakes founders make which put their businesses in jeopardy.
7 Common Startup Tax Mistakes
1. Not Paying Quarterly Taxes
Some business owners get into trouble with the IRS by not making quarterly tax payments. But the laws are clear. After being in business for more than one year, most businesses are required to make quarterly tax filings and payments. And as with most legal matters, ignorance of the law does not exempt you from following it.
This issue can be avoided by consistently keeping track of your expected taxes and making regular quarterly payments. Even if a business isn’t yet required to file quarterly, it’s not a bad idea to start out by building the habit of making quarterly payments. Or at the very least, set the money aside so that it’s available.
Furthermore, making quarterly payments helps you avoid the major shock that comes from having to pay a massive annual sum all at once.
Using an Outsourced Accounting Service like Davis Crawford Accounting and Tax is a great way to keep those dates in mind. Let them help you know what’s needed and when.
2. Not Sending 1099s
Any contractor or freelancer who you’ve worked with throughout the year, and paid over $600, needs to receive a 1099 from your company. For every 1099 you’ve forgotten to send or filed late, you’ll be fined.
Plus, not sending 1099s on time inconveniences your partners and contractors by potentially delaying their tax filings.
Fortunately, this mistake can be easily avoided. Engaging an Outsourced Accounting Service like Davis Crawford Accounting and Tax that specializes in business payroll will help you make sure to get those 1099s out on time (or automatically).
3. Not Tracking Expenses
Fast-moving businesses sometimes find it difficult to keep track of receipts and expenses. Then, when tax time comes around, the business owners find themselves scrambling to assemble a year’s worth of receipts and invoices.
From the very beginning of the business, you’re able to deduct “ordinary and necessary” business expenses. These expenses could come from miles driven to meet with your accountant, office supplies or entry fees to participate in a trade show.
But of course, if you can’t document it, you can’t claim it. You need to be able to prove that you incurred the expenses in the proper time frame.
4. Inadequate Business Entity Structure
The various business entity structures (LLC, C-Corp, S-Corp) all have their own specific tax implications. Matching your entity structure to your business is critical for ensuring you’re not overburdening your business (or yourself) with taxes or paperwork.
If you suspect your structure doesn’t fit anymore, the decision to switch shouldn’t be made lightly. While it’s possible to restructure, you should know in advance what effort and expenses you’re incurring if you decide to go that route.
Avoid this pitfall by researching and discussing with an accounting professional experienced with small businesses. Have them outline and explain the pros and cons of the different structures and help you select one that fits for you.
5. Not Writing Off Certain Business Expenses
For example, insurance is an essential expense for all businesses. Most businesses also need some form of business liability insurance as well. In some cases, it may even be legally required.
Insurance helps to protect the business, its owners and employees from catastrophic loss or crippling lawsuits. Insurance products like:
- Worker’s compensation
- General Liability
- Commercial Property Insurance
But many business teams don’t realize that as long as the insurances are considered necessary for the business, they’re tax-deductible.
Using an Outsourced Accounting Service like Davis Crawford Accounting and Tax that specializes in small businesses can help you catch this sort of deduction. Otherwise, you’re leaving money on the table.
6. Mixing Personal and Business Finances
In the beginning, it can be a real challenge to keep business and personal finances separate. LLC pass-through income can also make this a real hassle for growing businesses.
It’s no wonder that it can be hard to keep them separated. Owners are often spending massive amounts of time, energy and personal funds to push the business forward.
To avoid this tax problem, either don’t mix personal and business finance at all or separate the two as soon as possible.
7. Not Using an Accounting Service
An accounting service focused mainly on small businesses knows what you’re going through and what to look out for. You’ve got enough things to focus on, learning the ins and outs of business tax best practices doesn’t need to be one of them.

Locations We Serve
We maintain physical offices in New Jersey and New York but work with clients all across the country! With streamlined technology and processes, location isn't barrier to accessing top-tier financial services. We provide convenient access to expert accounting, bookkeeping, payroll, tax preparation & planning, and financial reporting services no matter where you are in the country.
Work with us
Are you ready to maximize your tax savings with our expert strategies while minimizing your overhead and operating costs?
Experience comprehensive financial solutions with our all-in-one Outsourced Accounting monthly subscription service, covering accounting, bookkeeping, payroll, tax preparation & planning, and financial reporting for your business's sustained growth and success.
Click below to book your free consultation.

Let's stay in touch!
Join our mailing list for exclusive tax and accounting updates delivered straight to your inbox. We promise to send emails only when we have something truly valuable to share. Unsubscribe anytime.