After a long pause, Up at Night is back. For our first episode, Jeremiah Curvers sits down with retail strategist and author Chris Parsons to discuss what it really takes to grow a retail brand today. Drawing from more than 25 years of experience across Walmart, Newegg, and Home Hardware, Chris shares practical lessons on leadership, customer experience, AI, and the future of retail.
What It Really Takes to Grow a Retail Brand Today
Chris Parsons coded Walmart Canada’s first website in 2004 with a copy of HTML for Dummies he bought at a bookstore. By 2007 it was one of the largest e-commerce platforms in the country. He later took a struggling Newegg business to $100 million in a single year, ran its e-commerce across eight countries, spent six years at Home Hardware, and published Retail Rewired in October 2025.
Chris joined me for the first episode of Up at Night since the relaunch. This isn’t a recap. It’s the six ideas from our conversation that matter most if you’re growing a retail brand right now, with my own take from running Polysleep layered in. The full episode is below.
Did your business actually grow, or did prices just go up?
Chris’s first point is the one most P&Ls hide. A retailer can post a banner year, up 20 percent, and still be shrinking. Strip out inflation and transactions are down; revenue only looks strong because every product costs more.
The question isn’t whether revenue grew. It’s whether more customers bought from you, more often, at healthy margin. If you can’t say yes to at least one of those, you didn’t grow. You repriced.
Marketing can’t fix what operations broke
Chris told a story I’ve seen versions of for years. A retailer’s quarter was slow, so leadership asked marketing to drive sales. He spent an extra million dollars and the foot traffic showed up. Sales didn’t. On day two he asked where the campaign budget had come from: operations had funded it by cutting store staff hours. Customers walked into full stores with nobody to help them, and the company paid twice for the same failure.
Retail is one ecosystem. Marketing, operations, and merchandising either move together or they cancel each other out. Before you approve a big push, ask what the department next door gave up to fund it.
Most cannibalization is growth you refuse to count
Chris used to live near Fergus, Ontario, in a Walmart catchment that pulled shoppers from 30 minutes away. When Walmart opens a new store closer to those shoppers, they stop driving to Fergus. Nobody calls that cannibalization. They call it growth. Move the same behavior online and suddenly it’s treated as a threat to the stores.
I’ve lived this debate. Post-COVID, roughly 37 percent of mattress buyers are comfortable purchasing direct online. The other two thirds want to touch the product before committing, so they buy through stores. That’s why we keep Polysleep focused on the direct-to-consumer buyer and meet the rest of the market through retail partners. The customer already decided where they want to buy. Your only decision is whether to show up there.
Customer experience is the loyalty program
Retailers spend heavily on points programs while the store experience quietly drives people away. Chris’s self-checkout math makes the point: a customer writes their own list, finds their own groceries, scans them, weighs the vegetables, packs the bags. You treated them like an unpaid employee for 40 minutes, nobody spoke to them, and then you email them a points offer to build loyalty.
Compare that with his wife’s trip to Roots. The store didn’t have her sweater in the right color and size, so the associate shipped it from another location to her house, free, next day. She got exactly what she wanted and Roots kept the sale. Fix the 40 minutes first. The points can wait.
What is the AI moment of discovery?
Procter and Gamble called the store shelf the first moment of truth: you discover a product standing in the aisle. In the 2000s, Google reframed it as the zero moment of truth, and we all learned to win the search results page. Chris argues we’ve entered a third era. He calls it the AI moment of discovery.
The shift is in how people ask. Instead of searching ‘best barbecue,’ they ask an assistant, ‘I’m planning a backyard renovation. What should I buy?’ Chris ran the test on himself: rather than searching for a gray suit, he told ChatGPT what he was presenting at eTail Palm Springs and what the weather would be, and let it pick the outfit. When he moved from Ontario to Edmonton, one prompt planned the three-day drive, hotels included, around two cats.
He estimates about 30 percent of consumers already shop this way and expects it to pass 50 percent within six months. Right or not on timing, the direction is set, and it’s why we’re setting Polysleep up for agentic commerce with furniture.com now. Mattresses are bought at life moments: a move, a new kid, a renovation. If an AI assistant is helping plan that move, the brands it can see get the sale.
AI makes bad data worse, faster
Chris’s warning for every retailer chasing AI: the model is only as good as your product content and your data. Feed it incomplete product information and disconnected systems and it won’t fix your problems. It will make bad decisions faster, and with confidence. Put AI on the roadmap, test it where the downside is small, and fix the foundations before you let a model make recommendations about your business.
Canada is not one market. Go hyper-local
The macro backdrop is rough. Chris cited one Canadian bank declining about 46,000 lines of credit in a single week. He also pointed to Ontario cottage sales, where properties under $2 million sit while everything above $2 million keeps moving, because affluent customers aren’t living the same economy as everyone else. Averages lie. Segments don’t.
His prescription: stop marketing to Canada as one country. The week we recorded, Montreal was under an ice storm while BC felt like spring, and most retailers sent both provinces the same email. Chris calls one message to a five-million-person list lazy. He’s right. Localize the subject line, the creative, the inventory. When you need truth fast, run a rapid customer survey (he likes Caddle, which turns one around in days) or do what Sam Walton preached: walk your stores and talk to your staff. They already know what’s broken.
What keeps Chris up at night
Retirement. He turns 50 soon and wonders what AI and robotics will do to the economy his pension depends on. Professionally, it’s watching clients sprint at AI without retail fundamentals in place.
My own rule for advice, straight from this episode: hear everyone out, listen to nobody. Gather every perspective in the room, then make the call yourself. You’re the one accountable for it.
Watch the full conversation below, and grab Chris’s book Retail Rewired. New episodes of Up at Night drop every two weeks.
