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In this episode, I sit down with Benjamin Alarie, co-founder and CEO of Blue J, to explore one of the most fascinating founder journeys I’ve ever encountered. Imagine simultaneously being a tenured law professor and a venture-backed CEO, while reinventing one of the most painful and universal professional workflows: tax research. Ben shares how Blue J evolved from an academic insight into a hyper-growth AI platform transforming how tax professionals, enterprises, and advisors find answers in seconds instead of hours.

We dive deep into the origin story of Blue J, including how a walk down Charles Street in Toronto inspired the name, how Ben threaded the needle between academic life and startup life, and how large language models completely reshaped the company’s trajectory. Ben also breaks down the realities of selling into a concentrated enterprise market, navigating the economics of professional services, and scaling from idea to 300%+ year-over-year growth.

Whether you’re a founder, an operator, or a curious learner, this conversation is packed with insights on identity, reinvention, enterprise sales, AI transformation, and the emotional journey of becoming a venture-backed CEO.

Benjamin Alarie

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