Jake Karls, co-founder and Chief Rainmaker of Mid-Day Squares, has turned radical transparency into a brand strategy that's built a movement. In this conversation, Jake breaks down how and why the Mid-Day Squares team — a family trio who attend therapy together every seven to ten days — built their brand like a rock band, not a CPG company. He shares what "building out loud" actually looks like, where the line is between vulnerability and liability (including the moment his own proposal video went viral and crossed it), and how stepping down from his CMO role to become Chief Rainmaker unlocked his real superpower: storytelling, community, and making friends for a living. Jake also gets personal about growing up with learning disabilities, never reading a book until age 25, and then reading 50 in a single year — and why he recommends Jesse Cole's book to any founder thinking about how to build fans, not just customers.

Key Takeaways:

• Know your real role. Jake stepped down from CMO because he was genuinely bad at it (his words!) Finding the title that matched his actual strengths — Chief Rainmaker — unlocked both his potential and Mid-Day Squares’ growth.
• How you show up in person and how you show up online should be the same thing. When they don't match, audiences feel it immediately, and it repels rather than attracts.
• Trolls are usually hurting humans. Jake stopped fighting back and started reaching out privately — 7 out of 10 times people apologized and said they were having a bad day.
• Going to therapy with your business partners is one of the best investments a founding team can make. It builds trust, sharpens communication, and protects your relationships if the business ever struggles.
• One plus one is greater than two when everyone on the team is doing what they're actually best at.

“No one in the world is you. No one in the world is me. The moment I try to be you, I'm going to lose that game. You're always going to be better than me.”

• Follow Jake Karls on LinkedIn and Instagram
• Try Mid-Day Squares and check out their new No Bread PB&J!
• Find Your Yellow Tux by Jesse Cole

Special thanks to Vandeluxmusic for letting us use their track

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🤘 Podcast strategy & production by Binge-Worthy Studio