JD Miller announcing the AI Sales Fail Competition. Photo: Catalyst Ink
Chicago executive JD Miller launches "AI Sales Fail" contest ahead of TEDx talk on algorithmic identity
FOR IMMEDIATE RELEASE
Update: the AI Sales Fail contest closed on September 7, 2026. See the stories
CHICAGO, April 9, 2026 — When JD Miller built an Instagram page for his Chicago balcony garden, the tech executive never expected to become a vegan meat influencer. Yet an algorithm's misunderstanding about his "Chicago Bell Garden" brought a flood of unsolicited samples: a case of vegan cookies, industrial quantities of kimchi, and more steak rub than he could ever use. Today Miller is turning that fail into a contest, launching the online AI Sales Fail competition.
The announcement comes ahead of Miller's talk on Saturday, April 11, at TEDxNormal, where he will explain why the algorithm got confused and how people can reclaim their humanity in the age of the algorithm.
"AI is great at repeating patterns at scale," says Miller, a veteran chief revenue officer and CRO in Residence at Rothschild & Co.'s Five Arrows. "When these tools are well tuned, it's fantastic. The problem is when small errors get replicated faster and farther than any human could have taken them alone."
To highlight the gap between automation and human intuition, Miller is seeking the most absurd, cringeworthy or hilariously inaccurate stories of a sales algorithm losing the plot.
The contest coincides with the launch of Miller's new book, The AI Handbook for Sales Professionals (Catalyst Ink, March 2026). Drawing on decades in B2B sales and a review of 158 AI selling tools, the book shows sales teams how to use AI to augment, not replace, genuine relationship building. The winner will receive a signed copy and a selection of Miller's favorite steak rubs from the Chicago Bell Garden. Details at jdmillerphd.com/aisalesfail.
About JD Miller
JD Miller, PhD is a Chicago-based executive and CRO in Residence at Rothschild & Co.'s Five Arrows, advising companies on sales transformation. He holds a PhD in organizational communication and is the author of The CRO's Guide to Winning in Private Equity and The AI Handbook for Sales Professionals. jdmillerphd.com
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