What I Learned After Answering Dozens of Canadian Tax Questions in One Day

On November 27, I did something I had never done before.
I hosted a Reddit Ask Me Anything in r/SmallBusinessCanada.

To be honest, the whole thing started because one of our clients suggested it. I did not even have a Reddit account at the time. I had no idea what to expect. I did not know how much work it would be, what kind of questions would come in, or what would happen if I could not answer something on the spot. I also wondered what the tone on Reddit would be. Would people be snippy or argumentative. Would it turn into one of those threads where experts get attacked for trying to help.

Still, I decided to try it. #YOLO

Over the next 24 hours, more than 29,000 people viewed the AMA. There were 67 comments, 90 shares, and an upvote rate of 89 percent, which I am told is considered very strong on Reddit.

What surprised me most is what I learned from doing it.

Why I Did It

I spend a lot of time talking to business owners one on one. Zenbooks serves over 350 clients across Canada, and I hear the same themes often. Confusion about dividends. Panic over CRA. Trouble finding reliable accountants. Stress about cash flow. Uncertainty about write offs and incorporation.

When a client suggested I take these conversations public for a day, it made sense. Reddit has one of the most active small business communities in the country. If you want the raw version of what entrepreneurs are thinking about, that is where you go.

So I decided to jump in and answer whatever came my way.

What Surprised Me

It was far more rewarding and fun than I expected.

The questions were easier than I thought they would be. People shared enough facts and context that I could give clear and tailored answers without guessing. The tone was respectful. People were genuinely thankful. There was no trolling. No snark. No one trying to play “gotcha.”

What really surprised me was the response. I was not expecting over 29,000 views. I was not expecting that many shares. And I was not expecting that many people to message me privately afterward thanking me for explaining something in a way they finally understood.

It reminded me that Canadians want clarity. They want someone to give them straight answers without overcomplication.

What Frustrated Me

I spend a lot of time online, and I see a lot of bad advice floating around. Not just slightly wrong advice. Truly harmful advice.

People on forums giving tax strategies with absolute confidence when it is obvious they asked an AI model and completely misunderstood the answer. Short-form reels on social media presenting entertaining but completely false “tax hacks.” People taking loopholes from American videos and assuming they apply in Canada. And many times they are not even trying to mislead. They just do not understand how complex the Income Tax Act really is.

I do not have time to correct all of it. And frankly, trying to fix bad advice in a comment section often leads to arguments with people who want to be right more than they want to be accurate.

The AMA made it clear how much this misinformation affects real business owners. You could see the confusion in the questions. You could see people trying to do the right thing but getting stuck because of the noise.

It reinforced for me how important it is that good information is available somewhere that is easy to understand.

What Made Me Optimistic

The politeness and gratitude.

Not one person argued. Not one person dismissed the advice. The entire thread was civil. People were respectful, thoughtful, and genuinely appreciative.

It gave me a lot of optimism about the next generation of Canadian entrepreneurs. They want to run clean businesses. They want to follow the rules. They want to understand how things actually work. They want to build something real and lasting, not chase shortcuts or hacks.

It also made me realize how powerful it is when industry professionals show up publicly and give clear explanations without jargon. There is a real hunger for honest, practical guidance.

I walked into the AMA expecting a long day of defending myself or wrestling with complicated edge cases. Instead, it felt like helping a room full of smart people who simply needed someone to translate the tax system into English.

Final Thoughts

I will definitely do another AMA. Probably quarterly. The experience gave me a better sense of what Canadians are struggling with, where the misinformation gaps are, and what content Zenbooks can create that actually helps people.

If you were part of the AMA, thank you for being so open with your questions. And if you missed it, I will link to the thread below.

Until then, if you run a business and you are feeling overwhelmed by taxes, CRA, bookkeeping, incorporation, or cash flow, you are not alone. Canadians across the country are running into the same issues. The good news is that most of the time the solution is simpler than you think.