How a Rainmaker Built a Chocolate Empire by Starting a Social Media Storm

Founding Mid-Day Squares

• 🚀 Mid-Day Squares began as a kitchen snack made by Jake's sister, evolving into a business with his sister and brother-in-law in August 2018.
• 📈 The company scaled from making 50 bars a day to over 135,000 bars daily, expanding from Montreal to the United States.
• ✅ Early agreements included committing to transparency by sharing the business journey (good, bad, ugly) and regular therapy sessions for partners.

The Power of Communication & Therapy

• 💡 Therapy sessions, facilitated by a non-biased coach, provide a safe space for partners to have hard conversations and resolve complex issues.
• 🤝 These sessions are crucial for protecting communication and family relationships, preventing founder conflicts that often lead to business failure.
• 🧠 The approach is likened to athletes having coaches, emphasizing that CEOs and business owners also benefit from external guidance.

Jake's "Rainmaker" Role

• 🎯 Jake identified his unique skill set as a "Rainmaker" – making noise, building community, and fostering relationships with investors, retailers, and media.
• 🚫 He learned to play to his strengths rather than weaknesses, stepping down from a CMO role to focus on connecting people and generating excitement for the brand.
• ✨ His job is to make people feel something deeply and become "friends of Mid-Day Squares," allowing other departments to execute on these relationships.

Authentic Marketing & Storytelling

• 🗣️ Mid-Day Squares' marketing strategy focuses on authenticity and making people feel something, rather than just listing product features.
• 📖 The human brain is wired to understand stories, so the brand prioritizes sharing its journey and evolving narrative to engage customers.
• 🌍 The company avoids politics and world events, instead focusing on delivering the best possible product and experience to consumers, inspired by Jeff Bezos's approach.

Entrepreneurial Realities

• 🏋️‍♂️ Entrepreneurship is described as a long grind filled with pain and challenges, not an "overnight success" story.
• 🧘‍♀️ Jake's therapist advised him to treat his demanding "Rainmaker" role like an athlete's performance and recovery, allowing for necessary downtime without guilt.
• 🗣️ A key lesson from his partners is to lean into hard conversations immediately, preventing issues from escalating and fostering better outcomes.