Built for connection — Powered by caffeine

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About 100 Cups

100 Cups of Coffee started as a personal journey to connect with others, one conversation at a time. Inspired by a leader’s philosophy around conversation being the key to understanding and collaboration—this initiative grew into a platform to exchange ideas, explore challenges, and discover solutions across industries around the world!

Our Mission

Built for connection and powered by caffeine, we believe meaningful conversations ignite bold ideas. Whether you're a leader, job seeker, entrepreneur, or simply curious—every cup brings us closer to insights that can transform our journey.

Matt Cennon Headshot

Meet the Host

Matt Cennon
Founder & Host

With over 15 years of leadership and talent acquisition experience, Matt specializes in creating spaces for meaningful dialogue that spark insight and innovation. He has facilitated hundreds of conversations with professionals across diverse fields, connecting people and ideas—one cup at a time.

Featured LinkedIn Posts

Upperbound 2025 Stage

100 Cups at Upperbound 2025

Picture this: cramming a thousand coffee chats with AI pros into just three days. That’s what Alberta Machine Intelligence Institute (Amii) Upperbound conference is in a nutshell—researchers, industry folks, and government all nerding out on how to harness AI for good and lock down Canada’s spot at the table.

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100 Cups of Perspective

During one of my 100 Cups, I sat down with a former senior leader turned executive coach. I shared a few ideas about what might come next for me. After listening, she said something that completely re-framed my thinking.

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100 Cups of Book Recommendations (🍁 Canadian Author 🍁)

A Spark in the Dark by Amy Davies is essential reading for anyone operating in a corporate environment. It pulls back the curtain on the realities of the 'reorg world' and offers a candid, relatable guide for multiple generations seeking a way through it. This book is honest, informative and funny; there are lessons learned, mistakes made, and exercises that anyone can use.

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Get in Touch

Email: mattcennon@gmail.com
LinkedIn: linkedin.com/company/100-cups-of-coffee/