Jack Fentress

AI Business Maturity Model (AIBMM) Coach 

Founder, Jolly Mammoth Co

Jack Fentress is an Eau Claire native and the founder of Jolly Mammoth Co., a human-oriented AI consulting company that helps businesses across the Chippewa Valley to make AI approachable and genuinely useful, teaching them how it can help them do more impactful and more joyful work.

After graduating from Memorial High School in 2019, Jack moved to Tennessee, studying at Chattanooga State and then at BrainCo Advertising School, where he began building his portfolio while living near the Smoky Mountains in Knoxville. He spent the pandemic years growing a freelance copywriting business for ESG and sustainability brands. When ChatGPT launched in late 2022, he watched it complete a version of his work in seconds. Instead of seeing it as a threat, he saw it as a sign that the way businesses operate was about to change and learned to drive AI instead.

In 2024, he returned to Eau Claire and began operating Jolly Mammoth, helping local contractors and service-based business owners navigate that shift. Drawing on experience in both the trades and marketing, Jack found that the same skills behind good creative translated naturally into building AI-powered business systems.

Today, for a company named after something that failed to adapt and went extinct, Jack's mission is spot on-brand: help businesses do the opposite.