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June 24, 2025 35 mins

How did three people with no social media following turn handwritten notes and free samples into a multi-million dollar snacking empire?

Building a successful food brand in today's market requires more than just great products—it takes authentic storytelling, community building, and the courage to do things differently. In this episode of B2B Breakthrough, host Ciara Cristo chats with Jake Karls (https://www.linkedin.com/in/jake-karls-653106ba/), co-founder and “Chief Rainmaker” of Mid-Day Squares (https://www.middaysquares.com), about revolutionizing the snacking industry through documentary-style marketing and direct-to-consumer innovation. Learn how they built a loyal following by sharing the good, the bad, and the ugly of entrepreneurship, scaled from handwritten notes to millions of customers, and created a brand that makes people feel like they're buying from friends.

Tune in to learn:

  • (00:00) The Serendipity Philosophy and Building Through Relationships
  • (03:50) From DTC Origins to Building Community Through Storytelling
  • (09:00) Transitioning from Direct-to-Consumer to Retail Success
  • (13:22) Why Traditional Food Marketing Fails and Fear Holds Brands Back
  • (16:57) Visual Branding Strategy - Bringing Lifestyle to Grocery Stores
  • (19:03) Manufacturing In-House - The Hard Choice That Creates Stories
  • (28:30) The ROI of Showing Up and Trusting Your Gut Over External Noise

Jake Karls is the co-founder and Chief Rainmaker of Mid-Day Squares, a revolutionary snacking company that has disrupted the traditional food industry through authentic storytelling and community building. Known for his documentary-style approach to brand marketing, Jake has helped build Mid-Day Squares from three people with no social media following to a multi-million dollar business available across North America. With a background in event planning and brand building, Jake specializes in creating authentic connections between brands and consumers through vulnerability, transparency, and genuine human relationships that drive both loyalty and growth.

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