How AI tax startup Blue J torched its entire business model for ChatGPT—and became a $300 million company

In the winter of 2022, as the tech world was becoming mesmerized by the sudden, explosive arrival of OpenAI’s ChatGPT, Benjamin Alarie faced a pivotal choice. His legal tech startup, Blue J, had a respectable business built on the AI of a bygone era, serving hundreds of accounting firms with predictive models. But it had hit a ceiling.Alarie, a tenured tax law professor at the University of Toronto, saw the nascent, error-prone, yet powerful capabilities of large language models not as a curiosity, but as the future. He made a high-stakes decision: to pivot his entire company, which had been painstakingly built over nearly a decade, and rebuild it from the ground up on this unproven technology.That bet has paid off handsomely. Blue J has since quietly secured a $122 million Series D funding round co-led by Oak HC/FT and Sapphire Ventures, placing the company's valuation at over $300 million. The move transformed Blue J from a niche player into one of Canada's fastest-growing