October 14, 2026
Why will AI reward the outdoor, retail, and hospitality brands that already do the basics well?
TL;DR: Sweet irony: the age of AI will reward brands that do well at what has ALWAYS mattered.
Externally, so consumers can find them: have a unique, well-defined brand that stands for something, is comfortable sharing its humanity and passion, tells the story of who it is, what it makes, and why it makes it, and actually means something to customers.
Internally, so they can leverage the new tools and ways of working: have well-designed processes and roles, clean and well-orchestrated data (structured and unstructured), strong collaboration and internal partnerships, actually care about their customers (vs. just putting that in the annual planning deck), and are willing to be nimble and experiment along the way. What has always mattered will matter more in the years ahead.
Two versions of this happening today:
Ask an AI assistant for the best three-season tent under $400 for the Pacific Northwest and watch which brands it names. It is not the brands with the biggest ad budgets. It is the brands whose products are described clearly, consistently, and by other people: reviews, forum threads, guide write-ups, dealer pages that agree with the original spec sheet. A weak brand, an undifferentiated product, or one with messy data never shows up well.
Second, in nearly every client "AI project," at a brand under a hundred people, the project becomes a data and process project wearing an AI badge. The tool is fine. What it needs is context: who the dealers are, what the return reasons actually say, how your best CS person answers a sizing question, which SKUs the rep force stopped showing last season. At most brands, that context is scattered across Shopify, the ERP, a Drive folder, and seven people's heads.
But both are illustrating the same problem.
The irony
Most of us, myself included, expected AI to reward the brands that moved first on the technology. So far, it rewards the brands that did the old-fashioned work well.
The reason is simple. The AI layer is the one thing every brand can buy. It is also the part that keeps changing; the model you use today will not be the one you use in 18 months. Daron Acemoglu, who won the Nobel in economics in 2024, put it plainly: "The money is in high-quality data and in applications. If your company, your line of business, has a lot of data, cultivate it." Your context, or tribal knowledge, is the only thing a competitor cannot buy, and whether a tool can reach it decides whether the tool is worth anything.
So the brands that spent the last decade on the unglamorous basics, a clear story and a clean back office, are the ones AI makes faster. Everyone else gets a very good assistant that knows nothing about them, or returns shitty output (crap in = crap out).
Next issue: the nine basics from the top, one at a time, run through how AI discovery and AI tools actually work.
What is the one piece of tribal knowledge your business runs on that lives only in someone's head?
Jordan Williams, Loop Trails, AI implementation for outdoor, retail and hospitality brands.