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 you
01:20 - Meet Jake Karls and Midday Squares
02:15 - From a Montreal condo kitchen to 150,000 bars a day
03:35 - Why build another snack brand?
04:20 - Finding white space in a crowded market
05:20 - Building a company with family
06:00 - Why the co-founders committed to therapy
07:15 - The two best investments they ever made
08:00 - Communication as protection against founder conflict
09:20 - Asking, “How are you really feeling?”
10:00 - When the CEO stepped away for her mental health
11:00 - Building structure without losing the soul
12:05 - The product differentiation behind Midday Squares
13:00 - The cocoa crisis that threatened the company
14:00 - Betting on the no-bread PB&J pivot
15:20 - The road from $40M to $100M
16:00 - Why the founders work in three-year tours
16:40 - Raising equity and government-backed debt
17:15 - Scaling manufacturing without growing too fast
19:00 - Building US retail distribution strategically
20:00 - Why attention matters as much as product-market fit
21:00 - Turning a snack company into a “band”
22:00 - Why content is not marketing
22:35 - How community helped Midday Squares break into Costco
24:10 - Selling community, not just a product
24:40 - Building a memorable founder persona
26:00 - The roles each founder plays in the brand
27:15 - Why Jake stepped down as CMO
28:00 - Becoming the company’s Rainmaker
29:00 - The risk of building a founder-led brand
30:00 - Making the company less dependent on its founders
30:30 - From anxiety and tears to trust in the team
31:20 - Hiring people better than the founders
32:30 - Building a brand that can stand on its own
33:30 - Why overnight success often takes 10 to 20 years
34:00 - Jake’s burnout and nervous breakdown
35:40 - The warning signs he ignored
36:20 - What recovery taught him about ambition
36:45 - The Wall Street meeting that changed how he showed up
38:15 - Authenticity, memorability, and having fun
38:40 - Taste-testing the no-bread PB&J
39:20 - Why the journey matters even if the outcome is uncertain
39:55 - Final reflections from Billion Dollar Moves

About Jake Karls

Jake Karls is Co-Founder and Rainmaker of Midday Squares, a better-for-you snack company founded in Montreal alongside his sister, Lezlie Karls, and brother-in-law, Nick Saltarelli.

The company began in a condo kitchen producing 50 bars a day and has since grown into a major North American consumer brand with a fully automated manufacturing facility, millions of customers, and ambitions to become a global afternoon snacking platform.

Jake leads relationship-building, brand momentum, media, retail partnerships, and investor engagement. He is widely known for Midday Squares’ founder-led storytelling strategy and its unfiltered approach to documenting the realities of entrepreneurship.

Billion Dollar Moves Podcast | The Top Global Venture & Business Podcast for Founders & Funders | Backed by HubSpot Podcast Network

Conversations with billionaires, unicorn founders, and the world’s leading funders.

Hosted by Sarah Chen-Spellings, Billion Dollar Moves examines how enduring companies—and the capital behind them—are built.

Through long-form conversations, the show explores decision-making under uncertainty, capital allocation, and the inflection points that shape category-defining businesses. From early platform backstories to allocator frameworks used across private markets, the focus is on judgment, incentives, and long-term value creation—beyond headlines and hype.

Built for those who take the long view.

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