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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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What does it take to survive, then thrive, as a public e-commerce CEO? In this episode of Start Up CEO, I sit down with Ghassan Halazon, co-founder and CEO of Emerge Commerce, who has spent 15-plus years buying, building, and turning around brands that together have generated more than one billion dollars in GMV.

We go deep on the shift from a wide roll-up to a focused portfolio in grocery and golf, the reality of timing acquisitions during the pandemic, and how Ghassan led a dramatic debt reduction while getting back to profitable growth. He shares how to handle competitor outreach, how to think about LTV to CAC, and what public market life actually feels like when the cycle turns.

If you are scaling an e-commerce company or considering acquisitions, this is a playbook on focus, discipline, and resilience.

Ghassan Halazon

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I’ve known Yoseph West, the Co-founder and CEO of Relay, for years, and in this episode of The Startup CEO Show, we finally get to unpack his story. Yoseph has quietly built one of the fastest-growing fintech companies in North America, serving thousands of small businesses while staying true to his principles.

We talk about how he went from the early days at Hubdoc to leading a 200-person company, what it takes to earn trust in a regulated space, and how he’s learned to lead with intensity without burning out. Yoseph opens up about his personal growth journey, from hands-on founder to strategic CEO, and how coaching, emotional intelligence, and discipline have shaped him along the way.

This is one of those conversations that reminds you what real leadership looks like: clarity, humility, and long-term focus. If you’re building something ambitious and trying to grow as fast as your company, this one’s for you.

Yoseph West

relayfi.com

Connect with me:

My website: https://limitless.ceo/

Linkedin:https://www.linkedin.com/in/themarkmacleod/

Instagram: https://www.instagram.com/markmacleodcoach/

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