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In this newsletter, youâll find:
đ« The black friday exclusion list that protects your margin
đ§ AI output is getting easier to understand and easier to advertise around
đ Ad of the day
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đ« The black friday exclusion list that protects your margin
Black Friday sends usually go to everyone whoâs engaged. A few groups inside that list will see your 30% off and respond by costing you money.
Each one needs a different email instead of the sale blast.
Group 1: Bought at full price in the last 14 days
Someone who paid $80 last week and now sees $56 has every reason to ask for the $24 back.
Run the math. If 5,000 customers bought at full price in that window and 8% ask, thatâs 400 requests and $9,600 in refunds, plus support time. The 8% is an illustrative figure, so use your own history from past sales.
Send instead: a thank-you with early access to a gift with purchase, or a store credit valid in January. It rewards them and pulls their next order into a slow month.
Omnisendâs BFCM AI playbook includes prompts for building suppression segments like this one. Because Omnisend connects with Claude or ChatGPT, you can ask for the list in plain language and skip the filter-building. You can try the BFCM prompts.
Group 2: Open support tickets
A customer waiting on a late or damaged order who gets a sale email is a likely spam complaint. Every complaint counts against your sender reputation during your highest-volume week.
Send instead: nothing until the ticket closes. Then add them back.
Group 3: Active subscribers
If a subscription costs $34 a month and the one-time price drops from $40 to $28 at 30% off, subscribers can cancel and buy one-time for less.
Send instead: a subscriber-only perk, such as a free add-on in the next box. They keep the subscription and still feel included in the event.
Group 4: Frequent returners
Customers who returned most of their last three orders tend to buy several sizes and send most back. A deep discount gives them more reason to do it. The âmost of threeâ cutoff is my judgment.
Send instead: a fit-focused email with your size guide and best-reviewed fits, at standard holiday pricing.
How to run it
Build all four segments now and check their sizes.
Refresh Group 1 and Group 2 daily from November 20, since both change fast.
Set the sale campaigns to exclude every segment, and schedule the alternative emails for the same morning.
After Cyber Monday, count price-adjustment requests and cancellations against last year.
Pull your full-price buyers from the last 14 days and multiply by your sale discount. That number tells you what this list is worth protecting.
đ§ AI output is getting easier to understand and easier to advertise around
Andrej Karpathy is experimenting with better ways to consume AI answers, while OpenAI is building richer ads and the measurement infrastructure marketers expect from established channels.
The Breakdown:
Karpathy Wants AI to Write Like Aircraft Manuals - Karpathy says prompting LLMs to follow ASD-STE100, a controlled English standard used for aircraft maintenance manuals, can produce cleaner, easier-to-read explanations.
Text Might Not Be the Best Answer - Karpathy suggests moving from writing to diagrams, interactive HTML pages, and custom explainer videos. He expects more human work to shift toward checking and understanding what AI produces.
ChatGPT Ads Get Visual - OpenAI will begin testing visual ads during image generation with select U.S. advertisers later this month. Ads will be labeled and separated from generated images.
OpenAI Builds the Measurement Stack - ChatGPT Ads is adding more attribution partners, incrementality testing, Negative Phrases, and brand-suitability pilots with DoubleVerify and IAS. Early data showed WeightWatchersâ CPA 15.3% below paid search.
Both changes point toward AI interfaces becoming more mature. Users may increasingly consume answers as diagrams, pages, or videos instead of blocks of text, while advertisers get more familiar tools to measure whether ChatGPT actually creates incremental customers rather than simply receiving attribution.
đ Ad of the Day
What Works:
Lifestyle Signals Function - The activewear setting instantly frames the drink around movement and wellness, giving the product a clear use case while strengthening message-market fit for health-conscious shoppers.
Copy Stays Scannable - âElectrolytes. Botanicals. Light sparkle.â compresses the value proposition into three fast proof points, reducing cognitive load and making the functional benefits easy to absorb on mobile.
Product Feels Aspirational - The overhead angle, sunlight and natural palette make the drink feel fresh and premium, while the visible can-in-use reinforces both consumption context and branding recall.
Show the product inside the exact lifestyle moment it belongs in, then support it with three concise benefits. That keeps the creative aspirational without losing conversion clarity.
đ„ł Events
đ„ What to Measure When AI Search Doesnât Get the Last Click
October 15 | Virtual Event
Matt Hammel, COO of AirOps, joins Zak Prauer, Expert Partner at Bain & Company, to show what citations alone miss, why recommendations matter more when buyers compare options, and how to judge AI search investment without waiting for perfect attribution.
Canât attend the session live? Register anyway, and youâll get the recordings in 24 hours.
đ„ What Makes a Creator Program Worth More Budget
October 21 | Online | Free Festival
See how experienced teams prove creator impact before asking for more spend. Leaders from Adobe, ĆURA, Edelman, Ogilvy, and more will break down the metrics, campaign decisions, and operating systems that help creator programs earn trust, budget, and room to scale.
Canât attend every session live? Register anyway, and youâll get the recordings in 24 hours.
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