How Midday Squares Is Building a Billion Dollar Brand Through Community, Chaos & Conviction | Jake Karls

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 that can outlast you01:20 - Meet Jake Karls and Midday Squares02:15 - From a Montreal condo kitchen to 150,000 bars a day03:35 - Why build another snack brand?04:20 - Finding white space in a crowded market05:20 - Building a company with family06:00 - Why the co-founders committed to therapy07:15 - The two best investments they ever made08:00 - Communication as protection against founder conflict09:20 - Asking, “How are you really feeling?”10:00 - When the CEO stepped away for her mental health11:00 - Building structure without losing the soul12:05 - The product differentiation behind Midday Squares13:00 - The cocoa crisis that threatened the company14:00 - Betting on the no-bread PB&J pivot15:20 - The road from $40M to $100M16:00 - Why the founders work in three-year tours16:40 - Raising equity and government-backed debt17:15 - Scaling manufacturing without growing too fast19:00 - Building US retail distribution strategically20:00 - Why attention matters as much as product-market fit21:00 - Turning a snack company into a “band”22:00 - Why content is not marketing22:35 - How community helped Midday Squares break into Costco24:10 - Selling community, not just a product24:40 - Building a memorable founder persona26:00 - The roles each founder plays in the brand27:15 - Why Jake