What we think


Tax Checklist for Entrepreneurs

by Peter J. Creedon

The dreaded 2015 Tax filing deadline of April 18th is quickly approaching. If you already filed your taxes, great! If you filed your Tax return with errors or forgot to add a deduction, you can’t change your filing, but you can send a Tax amendment by filling out Form 1040X. If you haven’t filed your Taxes yet, best to start as soon as possible, as you don’t want to get hit with late fees and interest.

A good resource to self-file your Taxes for free is: irs.gov. For complex Tax filings, you may want to consult with a CPA (Certified Public Accountant) or EA (Enrolled Agent) or other Tax Advisor. To make the process a little easier for you, here is a Tax checklist for entrepreneurs:

2016 Tax Checklist for Entrepreneurs

✓ Create a system for your Tax documents and receipts

To make your filing easier, having a good filing system is key. If you are doing your own taxes, this can help you limit the time and frustration spent on putting together your Tax return. If you are working with a CPA, having a good system could decrease your cost substantially, as CPA’s are usually charged by the hour. Keep a folder, either on your computer or in paper with all the appropriate documents. Make sure to collect and store receipts. Two great organizing softwares are: Shoeboxed or Wave appWave app. Both apps will store and categorize receipts for you, so you don’t have to carry them around.

✓Gather appropriate information

Personal information

• Social Security Number or Personal Identification Number for you and if filing jointly your spouse/dependents
• Last year’s tax return (2014)

Business Information

• EIN (employment identification number)
• Bookkeeping and Financial Statements

Since your business is incorporated, you also need to provide basic information like:

• A copy of your Certificate of Incorporation
• A synopsis of the principle product/service provided
• The list of your company director names, phone numbers and addresses
• Shareholders names, Social Security Number and Federal ID Number for corporations
• Number & Class of shares owned
• Key contact person other than directors provided

Financial Information (personal and business)

• Employment W-2 and/or 1099 statements
• Income and expense receipts
• Benefit statements such as unemployment.
• Income statements for self-employment or business, including MISC-1099s and Schedule K-1s
• Information for any taxes you have paid during the tax year (estimated tax payments, property tax, sales tax)
• Mortgage interest statement if you own a house
• College tuition statements, student loan interest, education expenses (if you are a college student)
• Retirement account contributions or distribution documents
• Charitable donations made throughout the year including receipts
• Medical expense statements and health insurance receipts, medical savings account contributions (HSA)
• Job search expenses or moving related expenses
• 1099-C forms, if you cancelled any debt during the year
• Investment forms for dividends or interest income earned
• Record of alimony received
• Energy efficient home improvement records and receipts
• Child or dependent care records, if you have children or dependent adults and pay for daycare or babysitters, so you can work

Document your expenses

• Meals and entertainment (business related)
• Accounting or lawyer expenses
• Office supplies

Home Business Information

• If you run a business out of your home, you’re going to need additional information to complete your Taxes:
• Records for income
• Office and supply expenses
• Utility expenses
• Total square footage of your home if you are claiming a dedicated home office
• Square footage of your dedicated office space or supply storage (so you can deduct a percentage of your utility bill, rent or mortgage, etc.)

Vehicle Business Information

This applies if you use your car for business purposes:
• Car mileage
• Fuel and oil costs
• Lease payments
• Parking fees
• Repair and maintenance
• Insurance

✓Know which deductions and credits you are eligible for:

Personal Deductions

• Interest from Mortgage, Home equity loans
• Points
• Health Insurance
• Real-Estate Taxes
• Student Expenses- Tuition and fees
• Credits – American Opportunity, Hope, Lifetime, learning credit
• Student Loan Interest
• Job Hunting including travel
• Home Office
• Entertainment
• Charitable contributions (IRS Publication 1771)

Business Deductions

• Rent: either home office or rent for office space
• Subscriptions
• Office Supplies
• Utilities
• Health Insurance Premium
• Certifications
• Travel and Entertainment
• Retirement Contributions


• Foreign Tax Credit
• Dependent and Child Care Credits
• Education
• Retirement Saving Contribution
• Earned Income Credit

If you have financial questions or want to discuss your tax planning strategy, feel free to reach out to a Certified Financial Planner (CFP®) for a free consultation at: info@crystalbrookadvisors.com or contact a CPA or EA.

Crystal Brook Advisors is a financial planner and registered investment advisor. We provide financial advice, investment management, and tax planning strategies to individuals and businesses, however, we are not Tax Advisors or Certified Public Accountants (CPA), and do not provide tax preparation or legal services.