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Thursday, September 17, 2026Vol. I · Edition 052Est. 2026

The Daily Hallucination

Confidently wrong about technology since 2026.

Startups

Founder Pivots for Ninth Time, Launches AI for Pivoting

"Pivotly" helps startups identify the moment their current idea has failed, which its founder says he has "a lot of training data for."

SAN FRANCISCO — Serial founder Jared Kesselman announced Tuesday that his company, previously a fintech app, a marketplace for dog walkers, a Web3 loyalty protocol, a mental-wellness chatbot, and four other things, has pivoted for a ninth time and is now Pivotly, an AI platform that tells founders when to pivot.

"I have never been more sure about anything," Kesselman said, a sentence he has now said publicly nine times. "Pivotly uses everything I've learned. When your metrics flatten, when your co-founder stops replying, when an investor says 'interesting' in a certain tone, Pivotly detects it. It gives you a score. Above 70, you pivot."

The product is built on a model trained on the company's own history, including 3,400 Slack messages, six pitch decks, two failed fundraises, and a Notion page titled "What are we actually doing." Kesselman said the model correctly predicted each of his previous eight pivots with 100 percent accuracy "in backtesting."

Early customers have praised the tool's honesty. "It told me my idea was bad on day one," said one founder. "Then it told me the pivot was bad. Then it suggested Pivotly's idea. I think it might just be him."

Investors who backed the original fintech company in 2021 said they remain supportive. "We invested in Jared," said one, "and we have gotten a great deal of Jared."

Kesselman said Pivotly is already profitable, because he is its only paying customer and has set the price at his own salary. He added that the model recently returned a score of 74 for Pivotly itself, and that he is "listening."