Amazon.ca is smaller than Amazon.com, but that may be the point.
Canada is a growing ecommerce market with less competition, familiar consumer behavior, and a clear path for experienced Amazon sellers. The opportunity is there, but so are the GST/HST, CARM, import, and recordkeeping requirements.

We can help from sales tax registration, filings and importer documentation requirements. Find out how and easily expand your sales to Canada.

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You're the Bottleneck

A friend of mine has a daily Amazon task he runs through Claude. He'd built a careful prompt over months that orchestrated what he wanted to do.

One morning he forgot. Typed what he wanted in one sentence. Got the best output he'd ever seen. WTF?

He’d been the slow part the whole time.

This is going to compound with every model release, as the gap between scripted prompts and outcome will continue to widen. The seller who locked in a workflow eighteen months ago is frozen at eighteen-months-ago quality.

If you have a structured prompt you’ve been using for a long time it’s going to give you weaker results. Crazy.

At this point we’ve seen how fast the AI models ship stuff (weekly? daily?). But this seems pretty clear: Eventually, prompt engineering goes the way of "knowing how to look things up." The skill collapses. What replaces it is the only thing the agent can't do: know what you actually want.

Today, the moat is still operational. Whoever has the cleanest SOP, the tightest PPC structure, or the best supplier relationships wins.

In the near future, the moat will be taste.

Taste is brand clarity. Taste is knowing what an on-brand listing looks like, what a wrong-feeling product would be, who exactly you're for. If you can articulate that, the agent builds everything around it. If you can't, the agent gives you the same generic output it gives every other seller, and everyone converges somewhere in the middle.

In the near future, we won’t be telling agents how to do their work. We’ll be telling them what good work looks like. Outcomes, not processes.

Here’s a guess: The brands that win the next decade are the ones whose founders can finish the sentence "we are the brand of ___." The ones who can't will run great agents, get average results, and never understand why.

The IVS

Big thanks to Marsha Cosman for jumping in here for this week’s IVS. Marsha’s latest book Living The Digital Nomad Dream is available now on Amazon When she’s not handling books & taxes, Marsha is spending time with her boys and enjoying the Costa Rican sunshine.

Can You Pay Your Kids from Your Business?
Here’s How to Do It Right

Yes, you can absolutely pay your kids from your business.

No, you cannot pay your 7-year-old "Vice President of Strategic Operations" $52,000/year for eating Goldfish beside your laptop.

CRA and the IRS have heard that one.

Why it works:

You're probably paying tax at a high rate. Your kids probably pay nothing.

In 2025, a Canadian child can earn roughly $16,000 before paying federal income tax. So if your teenager legitimately earns $8,000 helping your business... that income may be taxed at 0% instead of 48%.

That's not a loophole. That's tax planning.

What kids can actually do

Ecommerce businesses have a huge advantage here. Real tasks: packing orders, labeling inventory, product photography, social media, basic admin.

Honestly, most teenagers run circles around us on TikTok anyway.

The test:

Would you pay someone else to do this work?

If yes, you're usually fine. If the answer is "well... he exists near the business..." that's probably not enough.

CRA/IRS wants real work, reasonable pay, proper records, and actual payroll (T4 in Canada, W-2 in the US).

Do this:

1. Track hours. Date. Hours. Tasks. Done.

2. Pay reasonable wages. Don't pay your child $85/hour because "he's very gifted."

3. Run payroll properly. Random e-transfers called "pizza money" are not a payroll system.

The sneaky long-term benefit”

Salary creates RRSP or 401K room. Your teenager learns work ethic, earns money, and starts building contribution room years before their peers.

Just remember the difference between:

"My teenager helps run our ecommerce operations..."

...and:

"My 4-year-old Chief Vision Officer earned $31,000 this year."

Sell on Amazon.ca? You just got paid.

Amazon has begun to pay out the rescinded DST (Digital Services Tax)

Reminder: This was the digital services tax that Trump strong-armed the Canadian govt into removing.

If you sell on Amazon CAN, - check your Amazon CAN / Amazon US payouts > transaction view > filter by other.

There should be a bulk payment in there. Enjoy!

Dude, You Can Afford This

Costa Rica real estate is all over the map right now. You can find basic condos, older beach homes, luxury villas, gated community properties, and everything in between. But this year feels a little different. There has been a pullback in some areas, and that means there are definitely some deals to be had, especially if you are a cash buyer. I have seen more seller financing options too, but those are usually over 3 years max so you still need a bunch of cash at the end. Usually good if your selling a business or another property.

Like anywhere, location matters. The closer you are to the main airports, major beach towns, international schools, and developed areas, the more expensive things usually get. The further you move away from the main airports and tourist hubs, the more value you can often find, and that is where Costa Rica can get interesting compared to “back home”.

In many parts of Canada or the U.S., $500,000 might get you a basic suburban home, small condo, or something that still needs a lot of work. Depending on the area, that same money can sometimes get you close to the beach, with more space, a pool, and the ability to use the property as both a lifestyle purchase and a rental asset.

Here’s one example: a 4-bedroom, 4.5-bath home asking $510,000. It has 1,938 sq. ft. of living space, its own pool, and it is only a few minutes’ walk from the beach…for real not the fake “walking distance to the beach”. It is a newer style home, it has good size, a solid location, and is only about an hour from the airport which is key.

The rental math is where it can get interesting. If a home like this rented for even $250 per night for 100 to 120 nights a year, that is $25,000 to $30,000 in gross rental income. Factor in property management, cleaning, maintenance, utilities, insurance, and platform fees, it is not going to be free money but it can decently offset the carrying costs when you are not using it. Trade off is usually best money is the holiday rentals.

That is the appeal. You are not just buying a vacation home. You are buying a place you can escape to, work from as a digital nomad, spend winters in, and potentially rent out when you are not here. Costa Rica is not “cheap” anymore in the most popular areas. But if you are patient, flexible on location a bit, and ready when a motivated seller appears, there are still some very interesting opportunities starting to show up.

The Amazon Fee You Forgot About

Amazon has a Low Level Inventory Fee (LIF). Do you know what you’re paying for this fee, right now? I didn’t.

Your first step: Download the report here which shows the LIF by ASIN for any time period.

How to avoid it in the future:

1. Strong forecasting software is your friend. Stuff with minimums so that your inventory never drops below a certain amount.

2. If you have auto-refill on AWD for 70% of your SKUs, you will get charged no lower inventory fees.

3. Ship often, ship small, ship earlier than you think you need.

Yes, Your Credit Card Covers Trip Insurance. But…

You probably already know your premium card (Chase Sapphire, Amex Platinum, BMO World Elite ) bundles in $10,000+ of trip cancellation coverage. Not news.

Here’s a few things you might not know:

1. The card you paid with is the card that covers you. If you have a Sapphire Reserve but booked the flight on your Amazon Store Card, you have no coverage on that trip. Use the right card at booking, every time.

2. Save the benefits PDF to your phone now. Google your card name plus "guide to benefits." You'll never dig for it during the actual emergency, which is the only time you'd need it.

3. Know the gaps. Card coverage isn't unlimited:

   1. Medical evacuation is usually capped low or excluded (matters for diving, skiing, remote travel)

   2. Most cards cap trips at 60 days

   3. Cruises and pre-existing conditions often excluded

   4. Some cards reduce payouts over age 70

If any of those describe an upcoming trip, it may be worth it to get insurance elsewhere.

To your success,

Rob & Max