Discussing Lands' End with ChatGPT

Y'all realize, of course, that your utter dependence on Facebook/Google for new customers puts the future health of your business at serious risk, right?

Here's a discussion I had with ChatGPT.

Kevin:  Lands' End seems to rely heavily on discounts and promotions as part of its core business strategy for several reasons:

1. Perceived Value Strategy

Constant discounts create a sense of getting a deal, which encourages customers to buy more. If customers feel like they’re getting high-quality products at a reduced price, they’re more likely to make a purchase — even if the "original" price was inflated to allow for the discount.

2. Customer Conditioning

Over time, Lands' End has trained its customer base to expect discounts. If you know there’s always a sale around the corner, you might hesitate to buy at full price — but you'll jump at a 40% off email. This creates a shopping pattern where customers are almost waiting for the next sale to make a purchase.

3. Competitive Market Pressure

The apparel industry is highly competitive, especially in the mid-tier, classic, and outdoor clothing markets where Lands' End operates. Competitors like L.L.Bean, Eddie Bauer, and even department stores frequently run sales. Lands' End likely feels the need to match or exceed these offers to stay relevant.

4. Inventory Management

Frequent sales help clear out seasonal and excess inventory. Lands' End sells a lot of seasonal clothing (coats, swimsuits, etc.), so offering regular discounts helps prevent stock from piling up and reduces storage costs.

5. Catalog and Email Marketing Dependence

Lands' End has always leaned heavily on direct mail and email marketing. Regular discounts give them a reason to send those emails and catalogs ("Get 30% Off Now!") and drive immediate sales spikes.

6. Margin Cushioning

Lands' End likely sets its initial prices higher, knowing that a large percentage of sales will happen at a discount. That way, even after applying a 30%–50% off promo, they can still maintain a healthy profit margin.

🧥 Bottom Line: It’s a mix of customer psychology, competitive pressure, and strategic pricing. If Lands' End suddenly stopped offering promotions, many customers might stop buying altogether because they’ve been conditioned to expect a discount.

Kevin:  Does Lands' End sell outerwear that would fit me?

That depends — what’s your size and fit preference? Lands' End is known for offering a pretty wide range of sizes, including:

• Regular, Petite, Tall, and Plus for women
• Regular, Tall, and Big & Tall for men
• Some outerwear even comes in extended sizes up to 3X (for women) and 4X (for men)

They’re also known for more relaxed, classic fits rather than slim or trendy cuts. If you prefer a roomy, comfortable fit, you’ll probably have good luck. Plus, they tend to use quality materials (like down, PrimaLoft, and waterproof fabrics) at reasonable prices, especially when you catch one of their sales.

What kind of outerwear are you thinking — a winter coat, rain jacket, or something lighter? 👀

Kevin:  I need a rain jacket, mens, size = 3x.

Got it! Lands' End does carry men's rain jackets in 3X, and their outerwear tends to be pretty size-inclusive. Their Squall® jackets are a popular choice — waterproof, windproof, and lined for extra warmth. They also have some lighter rain shells if you’re looking for something less insulated.

Want me to check what’s available right now or help narrow down the options? 🌧️😊

Kevin: Yes, and please recommend cheaper options from competing brands (links and images were provided, FYI).

Certainly! Here are some men's rain jacket options in size 3X, including selections from Lands' End and more affordable alternatives from other brands:

Lands' End Men's Big Waterproof Rain Jacket
This jacket features a wind-and-waterproof 2.5-layer shell with a breathable, moisture-wicking interior membrane. It includes an adjustable hood, front and chest zipper pockets, and underarm zippers for ventilation. Available in size 3X.

Portwest US440 Classic Waterproof Rain Jacket
An affordable option, this jacket is waterproof with sealed seams and a pack-away hood. It's available in olive color, size 3X.

Frogg Toggs Men's Rain Suit
This rain suit includes both a jacket and pants, offering waterproof protection. Frogg Toggs is known for lightweight and breathable rainwear. Sizes up to 3X are available. 

Columbia Men's Rain Jackets
Columbia offers a range of waterproof and breathable rain jackets. Some styles are available in extended sizes, including 3X.

REI Co-op Men's Rain Jackets
REI carries various men's rain jackets from brands like Marmot and The North Face. Some options are available in size 3X.

When selecting a rain jacket, consider factors like waterproofing, breathability, and additional features such as adjustable hoods and ventilation options. Lands' End offers quality options, and brands like Portwest and Frogg Toggs provide more budget-friendly alternatives without compromising on essential features.

Now, I'm asking questions like a moron, not like a human being. But please pay attention to the judgments that ChatGPT makes about Lands' End and other companies (calling Portwest budget-friendly).

Imagine the content that ChatGPT had to "steal" to train itself to make judgments about who Lands' End is, who they compete with, and the give-and-take between catalogs / email / discounts?

From a commerce standpoint, Google and Facebook are "dead men walking" ... via their current business model. If you are having conversations with AI and AI is steering you where it wants via judgements made by equations that are easy to create but hard to understand, you won't sit in front of a laptop typing questions on Google then visiting landsend.com, will you?

That personal relationship you have with your customers ... either via the community you created, or via your own email/sms marketing program ... are about to become critically important. Ultimately, your email/sms program is going to be replaced by something interactive, but until then that personal relationship is going to be so darn important.

Also ... what do you do when AI makes judgments about your brand that you don't like?

Gonna be a wild ride.

P.S.: This is the point where some of the hounds come after me ... "Kevin, Meta isn't stealing content, they're using readily available information to train AI to be smarter." Well, I searched LibGen to see if Meta used my information, and yes, they used several of my booklets to train their AI. Which, of course, is stealing. And yes, there's nothing I can do about it so complaining is meaningless. I have to adapt and move on. ChatGPT tells me that it makes a distinction between creating new ideas and synthesizing existing ideas. Oh. Great. Also faulty logic.