International Expansion and Its Trials

New customers bring threats you cannot see yet. Expanding into a new country looks simple from the outside: translate the listing, ship the product, collect the sales. The brands that get burned are the ones who stop at translation and never ask what else is different about the customer on the other side of that border.

On this episode of The Longer Game, Michael Maher spoke with Ryan Cramer, partnership manager at PingPong Payments, about what actually happens when a brand decides to go international. Ryan Cramer has spent his career moving between wholesale, direct-to-consumer, and marketplace selling, and he laid out exactly where brands underestimate the work involved in crossing a border.

The Opportunity Is Real, and It Is Getting Easier to Reach

Michael Maher opened with the numbers: Amazon US did roughly 147 billion dollars in retail sales, with Germany a distant second at about 27 billion. Still, marketplaces in the UK, Japan, and across Europe represent real, underused growth for brands that have plateaued domestically.

"Retail is now going global, where you can have small and medium sized businesses, their products, who only used to be able to sell it in the Midwest, for example, or you and I are now on the other side of the world at a snap of a finger."

— Ryan Cramer, Partnership Manager at PingPong Payments

Taxes and Currency Are Not Optional Details

Ryan Cramer flagged VAT and GST as the first place brands get tripped up. Amazon collects some of this on a seller's behalf, but the seller is still responsible for filing and paying tax authorities directly, often quarterly.

"I've seen people actually get tripped up because they haven't, for lack of a better word, it's like not paying your taxes. It'll just accrue over time. And then all of a sudden they're like, well, you didn't pay us three years ago."

— Ryan Cramer, Partnership Manager at PingPong Payments

This becomes especially painful when a brand tries to sell the business later and discovers an unpaid tax liability sitting on the books.

Localization Goes Far Beyond Translation

Even a market as culturally close as Canada requires more than swapping words. Quebec requires French listings, and word-for-word translation often does not capture what a product actually needs to communicate.

"If a customer sees the listing and it's completely not grammatically correct, it goes against everything, whatever that might be, you lose out on a consistent customer even before purchase."

— Ryan Cramer, Partnership Manager at PingPong Payments

Ryan Cramer pointed to imagery as an overlooked piece of the same problem. Michael Maher connected this directly to his own agency's work launching brands in Singapore, noting that using all-white models in a market with a different ethnic makeup sends the wrong signal before a shopper even reads the description. Ryan Cramer cited IKEA as a company that gets this right, adjusting page layout, imagery, and even seasonal messaging by exact region and dialect, not just by country.

Logistics Can Quietly Kill a Launch

Geography matters more than most brands expect. Canada is roughly the size of the United States by land area but has a fraction of the population, spread thin across huge distances.

"Canada is very much spread out. So the nature of, you have to start thinking, I can't maybe fulfill things third party, I might want to do it in Prime, because otherwise it might take seven days."

— Ryan Cramer, Partnership Manager at PingPong Payments

Shipping to remote regions like the Yukon can be cost-prohibitive enough that brands choose to limit where they will even sell within a single country.

Amazon Is Not Always the Right First Move

Ryan Cramer noted that Amazon is not the dominant marketplace everywhere. Cdiscount leads in France, Lazada matters across Southeast Asia, MercadoLibre dominates Central and South America. Going where the competition is thinner, even if the ceiling is lower than the US market, can be more profitable per dollar spent.

"As an entrepreneur, you're not trying to match apples for apples in different marketplaces. You get slices of each pie and you put it together, and that's how you grow, as long as there's consistent growth across all channels."

— Ryan Cramer, Partnership Manager at PingPong Payments

What This Means for Brands

• Budget for VAT and GST filing as an ongoing obligation, not a one-time setup task.
• Localize imagery and messaging to match the ethnic makeup and culture of each market, not just the language.
• Map out fulfillment realities before launch, especially in geographically large but sparsely populated countries.
• Research which marketplace actually leads in a given country. It is often not Amazon.
• Expect international revenue to arrive in small percentage gains across many markets rather than one dramatic jump.

Going international is more accessible than ever, but accessible is not the same as easy. The brands that win are the ones that treat every new market as its own culture, with its own customer, rather than a copy-paste of what already works at home.