Walmart's Holiday Plans Shows ... There Will Be Blood
Walmart, not satisfied with only one Black Friday event, is holding two. And with it, it raises the question to me -- is Walmart executing Amazon's strategy better than Amazon itself? And by that I mean -- your margin is their opportunity. And while the world is speaking about potential rumored Amazon layoffs, better to speak about what Walmart is actually doing.
What are Walmart's key strategies and events planned for the holidays?
Here's what's planned:
a clever Dr. Seuss-inspired campaign called "WhoKnewVille" which draws attention to the fact that Walmart has a lot of brands most people don't even realize.
3 new Deals events. Two weeks prior to Black Friday, Black Friday itself, and then Cyber Monday. Cyber Monday being an online-exclusive event.
Find out:
What is Walmart's core advantage over other retailers this holiday?
Which retailers are most at risk this holiday season?
Some of the Worst Mistakes I Made My First Time as CEO, and Marketing As Oxygen
How did you become CEO for the first time?
The first time I was CEO of a company, it was right after my boss got fired. In fact, that boss took me to lunch right after it happened to congratulate me. Right after he got sacked at a venture capital Board meeting. The same Board meeting I got called into right after by the lead VC and asked if I had interest in running the business. This former engineer and product person with no real sales and marketing experience said: “Sure what do I have to lose?” My thinking was simple, surely the bar was low because they just fired the professional CEO and knew I had never been a CEO before. Well, perhaps I should have been more worried. As a first time CEO, I made an incredible litany of mistakes. And of course this matters a lot when you are burning cash too fast, inbound sales are low, and you have a muddled product strategy. All the things that got my boss fired at the time.
How an 18-Year-Old Outsmarted Big Tech and Raised $1.4M with Liam Fuller
On this week’s Watson Weekend, hosts Rick Watson and Jessica Lasesky break down the most important retail and e-commerce news from the past week — including Q4 challenges, retail media momentum, and Amazon CEO Andy Jassy’s claim that AI will accelerate the decline of physical stores. They also touch on ThredUp’s peer-to-peer shift, agentic commerce liability, and Coca-Cola’s use of generative AI in advertising.
Then, stay tuned for a standout interview with 18-year-old entrepreneur Liam Fuller, founder of Source, an AI operations tool helping retailers access data and complete tasks more efficiently. Liam shares real-world lessons on entering the U.S. market, attracting talent, finding product-market fit, scaling deliberately, and selling to mid-market brands with complex back-office needs — all against the backdrop of rapidly advancing AI models and mixed reactions from retail execs.
If you care about where retail and AI are headed — and what it takes to build innovation inside a traditional industry — you’ll want to watch this episode.
Blank is Making a Comeback
On this week’s Watson Weekend, Rick Watson, Jessica Lesesky, and Nick Kaplan break down the surprising return of Toys “R” Us — from its post-bankruptcy revival and global licensing quirks to why stores in Canada never closed at all. They also dig into holiday nostalgia, store-in-store partnerships, the American Dream Mall flagship, and whether Target is the right next collaborator.
Is this a true retail resurgence — or just seasonal hype?
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