Chicago Executive JD Miller Launches“AI Sales Fail” Contest Following Tedx Talk On Algorithmic Identity

Chicago, IL - April 9, 2026 - When JD Miller built an Instagram page for his rooftop garden, the tech executive never expected to become a vegan meat influencer. Yet an algorithmic misunderstanding about his“Chicago Bell Garden” led to an overwhelming influx 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 movement, announcing the online AI Sales Fail contest.

The announcement follows Miller's talk this weekend at TEDxNormal, where he shared the reasons why the algorithm got confused. His talk, focused on reclaiming our humanity in the age of the algorithm, struck a chord with audience members who find that AI is increasingly attempting to sell them products and services – and the automated outreach can sometimes go hilariously wrong.

The AI Sales Fail Hook

“AI is great at repeating patterns at scale.” says Miller, a veteran Chief Revenue Officer and private equity advisor.“When these tools are well-tuned, it's fantastic. The problem is when small errors get replicated faster and farther than any human would have been able to take them alone.”

To highlight the gap between AI automation and human intuition, Miller - who coaches companies on their go-to-market strategies - has launched the AI Sales Fail competition. He's seeking the most absurd, cringeworthy, or hilariously inaccurate stories of when a sales algorithm lost the plot.

Bridging the Gap: AI and Humanity

The contest coincides with the launch of Miller's newest book, The AI Handbook for Sales Professionals. The book draws from his decades of experience in B2B sales, along with a review of 158 AI-based tools for selling to provide a definitive guide for navigating the intersection of artificial intelligence and human skill for sales professionals – ensuring technology remains a tool for augmentation, rather than a replacement for genuine relationship building.

The winner of the AI Sales Fail contest will receive a signed copy of the new book and a curated selection of some of Miller's favorite steak rubs he uses in the Chicago Bell Garden. Details at AISalesFail

About JD Miller

JD Miller is a Chicago-based executive, serving as Operating Advisor and board member to companies seeking sales transformations. With a PhD in organizational communication, his leadership is marked by the intersection of business, technology, and humanity. He is the author of The CRO's Guide to Winning in Private Equity, and The AI Handbook for Sales Professionals.

MENAFN09042026003238003268ID1110965241