FOUR TAX TRAPS [AND TIPS] MOST FOUNDERS FALL INTO.

Straight from the trenches of last week’s Financially Fierce Friday call, we’re bringing you the unfiltered truth about the tax traps that are tripping up Founders across the country.

Our panel? Three of our badass Certified Cashflow Canvas Coaches — Denise Sandberg, Tanya Hilts, and Nola Hrboticky — bringing 80 years of combined bookkeeping experience to the table.

These pros have seen it all. And now? They’re calling it out — the traps, the consequences, and the game-changing tips that can save your business from the brink.

Let’s break it down.

TRAP #1: Mixing Business with Pleasure (a.k.a. Personal and Business Finances)

One of the biggest rookie mistakes? Blurring the lines between business and personal finances. It’s messy, it’s risky, and it makes tax time a total nightmare.

What this looks like:

• Using one bank account for everything

• Charging business and personal purchases to the same credit card

• Paying for business expenses out of your own pocket — and losing the receipts

Tips to avoid this trap:

• Open a separate business bank account today. Even if you're a sole proprietor, this is non-negotiable.

• Get a business-only credit card — even if it's just a secondary card on your personal account.

• Use a digital receipt app (like Dext or Hubdoc) to snap and store receipts instantly.

• Pay yourself a set amount from your business account into your personal account. You’re not a vending machine.

TRAP #2: Writing Off Expenses That Don’t Belong

Yes, you want to lower your taxable income. No, that doesn’t mean writing off every coffee and tank of gas like it’s a business investment. CRA sees you — and they’ve got questions.

Common culprits:

• Claiming personal vehicle use without proper logs

• Declaring business-owned vehicle expenses without proper categorization (benefit? allowance?)

• Meals and entertainment not logged with who, what, and why

• Writing off so many expenses that your business shows no profit (which can hurt your ability to get loans or credit)

Tips to avoid this trap:

• Track vehicle mileage — and who owns the car matters! If it's yours personally, you need a log. If it’s corporate, talk to your accountant about taxable benefits.

• Every meal must have purpose: record who you met, what you discussed, and the business reason.

• Show a healthy bottom line. A $0 profit may look great at tax time — until you go to get financing. Your numbers tell your story.

• Remember: tax strategy is about optimization, not evasion.

TRAP #3: Filing Late (or Not at All)

This one’s a biggie — and shockingly common. Not filing your income tax, GST, or source deductions on time will tank your business faster than you can say “penalty.”

What this leads to:

• Interest and penalties that pile up faster than debt on a maxed-out card

• CRA collections (and trust me, they don’t play)

• Major headaches when trying to secure loans or investor funding

Tips to avoid this trap:

• Set calendar reminders for all your filing deadlines — or better yet, automate them.

• Set up a separate bank account for all your taxes: HST/GST, payroll deductions, and income tax. As the revenue rolls in, move your money over so it’s ready when you need it.

• File even if you can’t pay right away — filing late costs more than paying late.

• Be proactive: one Founder on the call submits estimated remittances quarterly, even for income tax. It keeps her ahead of the curve — and CRA off her back.

TRAP #4: Not Knowing How (or When) to Pay Yourself

Founders of incorporated companies, this one’s for you. There’s more than one way to get paid — and choosing the wrong one can come back to bite you.

Salary vs. Dividend. They’re taxed differently. They show up differently on your books. And they have different impacts on both your personal and corporate taxes.

Tips to avoid this trap:

• Book a meeting with your accountant at least three months before your year-end to make a game plan.

• Consider the impact of payroll deductions — CPP, EI, and income tax all come into play.

• Salary can be expensed by the business and comes with deductions (yay RRSP room). Dividends may reduce admin costs but don’t necessarily help with personal income qualifications if you need a loan or mortgage.

• Don’t wing it — this decision needs strategy, not guessing.

BONUS TAKE AWAYS

• Communication is key — if CRA is calling, don’t ghost them. And don’t go it alone. Bring your bookkeeper or accountant onto the call as your advocate.

• Your software is your scoreboard — don’t be afraid to look at your numbers. What gets measured gets managed.

• Stay ahead, stay safe — paying as you go may feel tough, but it builds financial resilience. Quarterly remittances, clear categories, and clean books are your power moves.

THE BOTTOM LINE IS THIS…

You didn’t start your business to get tangled in tax traps — but that’s exactly where too many Founders end up.

The good news? Every single one of these mistakes is preventable with the right knowledge, systems, and support.

Separate your finances. Stop gaming the write-offs. File on time. Pay yourself properly.

Simple? Yes. Easy? Not always. But this is the work that keeps your business strong, fundable, and future-ready.

And remember — you don’t have to do it alone. Get a coach. Get a plan. Get clear. Because when you take charge of your numbers, you take charge of your future.

ABOUT NAIL THE NUMBERS

At Nail The Numbers, we’re not just crunching numbers — we’re guiding a global movement to help Founders find their path to financial power.Our mission? To strengthen the minds and bottom lines of 1.7 million business owners worldwide — and we’re well on our way.

We’re the go-to financial training academy for business owners and the force behind the Cashflow Canvas — a bold, three-part process that transforms numbers into art, budgets into masterpieces, and businesses into bankable investments.

And we don’t stop with Founders. Our certification program empowers lenders, educators, and economic developers with the tools to help entrepreneurs build strong — and stay strong.

#StrengthInNumbers

ABOUT TAUNYA WOODS RICHARDSON

Taunya is well-known for her straight-shooting, bottom-line-building approach to founder finance. As the Founder of Nail The Numbers, she brings 30+ years of experience in entrepreneurship, finance, and neuroeconomics to our mission of strengthening the minds and bottom lines of Founders across North America.