About this episode

Jake Karls discusses the journey of building Midday Squares, emphasizing community, marketing, and personal challenges.

In this final episode of Billion Dollar Moves for a bit, I sit down with Jake Karls, Co-Founder and Rainmaker of Midday Squares, for a candid conversation about building one of North America’s boldest founder-led consumer brands. Jake shares how he, his sister, and his brother-in-law went from making 50 bars a day in a Montreal condo kitchen to building an automated factory capable of producing more than 150,000 bars daily. We talk about why the co-founders committed to therapy from day one, how founder-led storytelling helped turn customers into a community, and why great marketing is not simply content—it is making people feel part of something. Jake also opens up about burnout, anxiety, his decision to step down as CMO, Midday Squares’ pivot beyond chocolate, and the work required to build a company that can eventually stand without its founders. For founders, funders, family businesses, and consumer investors, this is a conversation about trust, brand, resilience, and what it really takes to build for the long term. Watch the full conversation and subscribe for more discussions at the intersection of capital, leadership, and long-term value. 00:00 - Intro: Building something…

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