Chief Rainmaker in Food & Beverage: Career Insights with Jake Karls | That’s a Food Job! #129
About Jake Karls
Jake Karls is the Rainmaker and Co-Founder of Midday Squares, the Better-For-You chocolate and snacking brand that has grown from a kitchen table idea to over 10,000 stores across North America. A graduate of Western University, Jake co-founded Midday Squares in August 2018 with his sister and brother-in-law, originally taking on the CMO role before realizing management wasn’t where his strengths were. He now holds a role few in the industry share: building relationships, community, and brand awareness full time, with no KPI other than “am I making friends or not.”
What We Cover in This Episode
Jake breaks down what it actually means to be a “Chief Rainmaker” and why relationship-building, not pitching, drives long-term business growth. He and the host dig into how students can network without the pressure of “needing” something from every conversation, why authenticity and storytelling matter more than a polished resume, and how Jake uses therapy and recovery time to sustain a high-travel, high-output role. He also shares how Midday Squares turned a cocoa price spike into a two-year R&D project that produced its first no-bread PB&J.
Watch the Episode Below
Resources
Timestamps
- 00:00 – Lean Into Yourself
- 00:20 – Meet Jake Karls
- 02:07 – Becoming Chief Rainmaker
- 04:26 – Life As A Rainmaker
- 07:37 – Networking Without An Agenda
- 10:39 – Humanization Is Your Edge
- 12:30 – Building Boldness
- 14:16 – Public Speaking Fears
- 15:32 – The Power Of Momentum
- 17:56 – Mentorship Through Social Media
- 20:39 – Finding Optimism Online
- 21:44 – Networking Event Tips
- 23:33 – Be Yourself, Lose The KPI
- 24:46 – What Makes A Good Story
- 27:30 – Facts Vs. Emotion
- 28:38 – Handling Online Criticism
- 30:22 – What’s Next For Midday Squares
- 33:20 – Self-Manufacturing Challenges
- 34:54 – Closing Thoughts
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