This website uses cookies

Read our Privacy policy and Terms of use for more information.

The Watson Weekly is sponsored by Avalara — the agentic AI platform automating global tax and compliance for leading eCommerce brands with simple plans, transparent pricing, and complete coverage across Shopify, Stripe, WooCommerce, BigCommerce, and more.

TL;DR

  • You Earned the Money. Walmart Just Kept Some. Retail compliance from 2 directions.

  • Agentic Corner: The AI and LLM news you need to know, not the slop.

  • Investor News Roundup: A B2B vintage marketplace raises funding, and more

THE INTERVIEW TAKEAWAY

You Earned the Money. Walmart Just Kept Some

Here's a number that should bother you if you sell into retail: three to five percent of your gross invoice, gone. Not to returns. Not to damaged goods. Gone to chargebacks.

Elle Smyth, CEO and Co-founder of RetailReady, put it in plain terms on the podcast this week. Do $10M shipping into retail and you can expect roughly $500k to disappear off your invoice. Zoom out and it's about $40B a year in the US alone. The reason brands lose their minds over this particular line item is that it isn't a cost. It's revenue you already earned. You made the product, you shipped it, and then Walmart or Target quietly hands back a smaller check than the one you were owed.

What did you do wrong? Usually nothing that has anything to do with the product. A label an inch off the spot the overhead scanner wants. A carton a hair over the max dimension buried on page 212 of a routing guide. A shipping notice that showed up in a format the retailer's system couldn't read. The box was fine. The paperwork wasn't.

I've been saying for years that compliance is where a lot of good brands quietly bleed out, and this episode made it concrete. Art Nimbley, who runs IT for Pierre Fabre in the US, told me his team used to eat thirty or forty chargebacks a week. Every one of those is a person running a root-cause investigation instead of doing real work. One of his employees was spending forty hours a month, a quarter of their time, hand-building shipping notices so the retailer wouldn't ding them. That's the tax behind the tax. It doesn't just cost you the deduction. It costs you the payroll you throw at avoiding the deduction.

The part that got me: when Pierre Fabre automated it, the technical chargebacks basically went to zero on the first order. Not down twenty percent. Near zero. Which tells you the problem was never that these teams are sloppy. The problem is that Walmart's guide runs 399 pages, Target's is completely different, and every one of them changes at least once a year. Nobody is beating that with a binder and good intentions.

So here's my take. If you're shipping wholesale and you've been writing off chargebacks as the cost of doing business, stop. That's a story you tell yourself because the alternative feels hard. Ask your 3PL one simple question: show me how you track chargebacks over time. If they can't pull it up, they don't have a system. They have a process and a prayer.

Today’s Watson Weekly episode is sponsored by Radial and Avalara.

THE BIG IDEA

One more thing from Art, because I loved it. The big retailers are not always right. He has challenged national accounts three times and won three times. Read the manual, trust your data, and go find a real human on the other side of that shared inbox.

The money is yours. Go get paid.

Listen To The Watson Weekly Interview

The $40 Billion Retail Tax Nobody Sends You a Bill For

July 15, 2026

Sponsor The Watson Weekly

The Agentic Corner

  • Supply Chain Dive: Apple has extended its partnership with Broadcom, who will supply it with more than 15B chips, at a cost of over $30B. US-made silicon chips are like chicken teeth.

  • Nekuda: Shopify has rolled out WebMCP unannounced. Hello Agent!

  • GeekWire: Auger (Remember Amazon’s Dave Clark) has announced it has raised $50M in Series B funding. Another AI company using “operating system” as its reason for existing.

  • Monogram: Announced a $30M Seed funding round emerging from stealth. AI meet visual interface.

  • geoSurge: Announced a $12M Seed funding round focused on a new thesis for AI optimization. Do we not have enough brand visibility startups?

Investor News Roundup

Watson In The Wild

Keep Reading