The 7 Common Tax Mistakes SK'Preneurs Won't Be Making This Year

January 30, 2016


In the flurry of launching a new business or first startup, filing your taxes can be a real learning curve. You won’t want to wait until the last minute to try to figure things out. At the very least, it could lead to money left on the table — or worse, costly penalties or other legal repercussions.

To make sure your new business is handling its tax obligations properly, run through these eight common mistakes:


1. Not Paying Your Quarterly Taxes

Businesses, including self-employed sole proprietors, are required to pay taxes on a quarterly basis. During your business' first year, you get a free pass, and there are certain other exceptions based on how much you make. However, even if you’re not required by the CRA to pay quarterly taxes, it’s still good practice — waiting to pay a year’s worth of taxes in one lump sum can give you quite a shock.


The best way to stay on top of your quarterly tax obligation is to get into the practice of automatically setting aside a percentage of each payment or revenue. Then, take stock of your profit/loss statement at each quarter and pay your quarterly bill accordingly. A financial advisor can help you estimate these payments if you need some help.


2. Not Keeping Track of All Your Expenses

From the moment you launch a business, you’re able to deduct all “ordinary and necessary” business expenses (e.g. office supplies, event fees, miles driven to meet with partners).


Your biggest mistake is not keeping track of these expenses throughout the year and trying to gather every receipt when it’s time to file. The bottom line is you can’t deduct what you can’t document, and failing to record as you go most likely means you’re forgetting expenses and leaving money on the table.


Find a method for documenting expenses that works for you. There are dedicated apps such as Expensify for tracking expenses, Milebug for recording mileage, or Shoeboxed for capturing paper receipts. In addition, an accounting program, such as Mint, QuickBooks or FreshBooks will let you record and manage expenses.


3. Not Taking the Home Office Deduction

Many startups, small businesses and other work-at-homers get discouraged from taking the home office tax deduction, because it has traditionally been considered a red flag for getting audited. However, if you are legitimately entitled to the deduction, there’s really no reason not to take it.


To qualify, your home office needs to be used exclusively for business purposes. This could be a dedicated room or part of a room in your house. But holding a meeting at your dining room table or working from your living room couch won’t entitle you to the deduction.


If you do qualify, you can write off a percentage of your home expenses including rent/ or mortgage payments, utilities and insurance costs.


4. Mixing Equipment and Supplies

Both first-time and experienced business filers get tripped up by which expenses are considered equipment vs. supplies. Supplies include things that you use during the year (e.g. printer paper, pens, toner cartridges). Equipment (i.e. capital expenditures) are typically higher-value items that will last significantly longer than one year. For example, a new computer, server and office chairs are examples of equipment.


When it comes to equipment, there are a couple of approaches: You can write off a portion for each year the appliances are in use, or write off the full amount — there’s a max limit here — for the year you purchased it. So, if you bought a few new laptops for the business in 2013, you can write off the full price with your 2013 return — but you’ve got to report these purchases as a capital expenditure.


If you mistakenly deduct your equipment or capital items as supplies, the CRA could determine that you improperly characterized the expense and that you’re not entitled to the deduction.


5. Over-Deducting Your Gifts

Maybe you gave your clients holiday presents, or sent a colleague a thank you gift in appreciation for a valuable referral or piece of advice. Business gifts can be deducted, but there’s a big catch. You can only deduct the first $25 given per recipient as an expense. So, if you sent Jack a $150 gift basket, you can only deduct $25 for it.


If you end up reporting $3,000 in deductible business gifts for the year, make sure you can back that up. It means you gave out gifts to at least 120 different people. You can read more about deductible gifts here.



6. Choosing the Wrong Legal Entity

Your startup’s legal structure affects how you report your taxes and how much you pay, so it’s important to choose the right entity. For example, many start out as a sole proprietor or partnership, then find themselves paying too much in self-employment taxes. Creating a  Corporation could help lower their tax bill.


A quick discussion with a tax advisor or CPA can help you figure out which structure is right for your situation.


7. Mixing Personal and Business

New startup founders and small business owners often invest so much of their time and money in the company that their personal and business finances become indistinguishable. This practice can lead to major confusion come tax time, and in some cases, can lead to legal infractions or loss of company status (Any corporation is required by law to maintain separate financial records and accounts.) Avoid trouble by establishing a company financial account from the start and maintaining separate records for the business.


Above all, any startup or small business owner must think of taxes as a year-long obligation, not just something to revisit once a year.








Nellie Akalp is a passionate entrepreneur, small business expert, professional speaker, author and mother of four. She is the Founder and CEO of, an online legal document filing service


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