I Spent a Day With the Founder of a $40M Chocolate Brand

I spent a day in Montreal with Jake Karls, co-founder of Mid-Day Squares, a chocolate brand doing over $40 million a year. Seven years ago Jake, his sister, and his brother-in-law were hand-making bars in a condo kitchen, about 100 a day. Today their factory makes 150,000 bars a day, and they've sold more than 75 million of them. Jake's title is Chief Rainmaker, which sounds like a joke until you follow him around for a day. He doesn't run operations. He's barely in the office. His whole job is making sure Mid-Day Squares is relevant everywhere. Most founders build the product and then begin marketing it. Mid-Day Squares documented their entire journey while it was happening, and millions of people follwed the brand before they ever tasted the product. CHAPTERS 0:00 Intro 0:29 Inside the factory 1:06 What is Mid-Day Squares and what a "Chief Rainmaker" does 2:26 Who creates the product 3:08 His sister on what Jake is good at 4:53 Store walkthrough: merchandising, damaged product & free samples 6:11 Calling mom, the brand's unpaid ambassador 7:28 Handwritten notes and keeping the human touch 8:11 On stage: storytelling as the real differentiator 9:17 Why a chocolate founder speaks to a room of finance people 10:00 Visiting their first retailer 11:23 The event cancelling 30 minutes out 12:02 Personalized customer video 13:29 The Crew Love wall 14:28 Advice for other founders THE FOUNDER Jake Karls, Mid-Day Squares ($40M+):   / jake-karls-653106ba   NEWSLETTER Every week I break down what's actually working in e-commerce, pulled from real conversations with brands and everything I see behind the scenes. Join over 5,000 founders and operators reading it: https://bensharf.com/ ABOUT ME I run Platter, a Shopify Platinum Agency that's built over 200 storefronts driving more than $1B in GMV for brands like Neuro Gum, G Fuel, Gainful, and Every Man Jack. This series is me getting in the room with founders at every stage to show the behind the scenes of brand building and what actually moves a brand to the next level. Learn More About Platter: https://www.platter.com/ ADD ME IG:   / bensharf   YT:    / @bensharf   X: https://x.com/BenSharf LinkedIn:   / ben-sharf-b554a5b3