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204 RiseAuthor: 204 Rise
204 Rise aims to document the rising talent hidden within the streets of Winnipeg. We want to reveal the talents of the city, whether that be through music, art, or business, in an entertaining, knowledge-based experience! Check us on youtube and instagram to see exclusive video content of some of the great guests we feature! Language: en Genres: Personal Journals, Society & Culture Contact email: Get it Feed URL: Get it iTunes ID: Get it |
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The Ugly side of Growing a Multi-Million Dollar Chocolate Bar Company | Jake Karls, Midday Squares
Episode 194
Tuesday, 2 December, 2025
What does it really take to build one of the fastest-growing chocolate brands in North America?In this episode, we sit down with Jake Karls, co-founder and chief storyteller of Mid-Day Squares. Jake opens up about the parts of the journey most entrepreneurs never share, heartbreak that reshaped his life, failed attempts that forced him to rebuild, losing himself along the way, and eventually discovering the role he was born to play. What started as a messy path of uncertainty led him to becoming the rainmaker of Mid-Day Squares, helping turn the company into a brand that has sold over $65M worth of bars.We talk about why he struggled as CMO and how owning your weaknesses can unlock your real superpower, the moment he decided to bet everything on Mid-Day Squares, and the impact therapy had on saving the partnership, the business, and his closest relationships. Jake also opens up about the pressure of being “on” all the time, the loneliness behind constant travel, and the emotional cost of building a brand in public.If you’re obsessed with entrepreneurship, storytelling, personal growth, or watching the underdog fight their way forward, this conversation will hit you deeply and stay with you long after it’s over.#204Rise #JakeKarls #MidDaySquares #Entrepreneurship #StartupStory #BrandBuilding #CMO #Storytelling #BusinessGrowth #FounderLife #CanadianEntrepreneurs #UnderdogStory #PersonalGrowth #MentalHealthInBusiness #WinnipegPodcast #Motivation #BusinessPodcast #CreatorEconomy #LeadershipJourney #SuccessMindset
