Eat Play Crush with Mary Shenouda

Jake Karls - Mid-Day Squares: From Bankrupt to 50 Million Bars Sold, Building Out Loud, and Burnout


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Being unapologetically yourself means embracing every part of who you are, without fear of judgment or rejection. It’s about standing tall in your truth, knowing that your quirks, flaws, and unique qualities are what make you extraordinary. When you stop seeking validation from others and start owning your story, you unlock the freedom to live authentically, create fearlessly, and connect deeply with those around you. True success begins when you show up as the most honest version of yourself, unapologetically and with confidence.

Today, let's welcome Jake Karls, the co-founder and "Rainmaker" of Mid-Day Squares, a revolutionary chocolate brand focused on authentic connections and clean, functional ingredients. Known for his bold personality and unconventional approach to business, Jake has built a loyal community by sharing the raw, unfiltered reality of entrepreneurship. Passionate about storytelling, community building, and making people feel something, Jake brings energy and heart into everything he does, both in business and life. 

Throughout the episode, Jake tells his story in a way that’s both inspiring and eye-opening. He begins by recounting his early ventures, including throwing college parties and a fitness business that went bankrupt, before finding his footing with Mid-Day Squares. Jake, now known as the "Rainmaker" for his ability to build genuine connections, opens up about the emotional toll of building a brand, from struggling with burnout to battling anxiety and self-doubt. Despite his success, Jake shares the importance of therapy and the challenges of balancing mental health with the demands of running a rapidly scaling company.

As the conversation unfolds, listeners get a behind-the-scenes look at the early days of Mid-Day Squares, from hand-making bars in a tiny condo to building a full-scale chocolate factory. Jake highlights the importance of storytelling in creating a loyal fan base, showing how sharing the highs and lows of entrepreneurship has been key to the brand's growth. He also touches on his personal struggles with health, reflecting on how years of putting the business first left him feeling exhausted and disconnected from his own body. Now, he's on a journey to prioritize self-care and rediscover the joy in both life and business.

What We Discussed:

  • 00:00 Intro
  • 00:24 “My job is to make friends!”
  • 02:18 The Mid-Day Squares
  • 03:50 Life Before Building the Business
  • 15:57 Who Were the Initial Customers?
  • 24:29 “I now have limitations.” 
  • 26:20 Therapy Can Help You
  • 29:27 The Goal is to Break the Costco Record
  • 35:30 “I stopped caring about my body.”
  • 40:13 Finding Your Purpose in Life Again
  • 44:52 Energy and Vibes in the First Meeting
  • 46:52 Don’t Neglect Your Own Health Issues
  • 50:28 Transparent Storytelling
  • 54:46 The Fear of Death
  • 57:50 What Would You Do with Uninterrupted Time?
  • 01:04:01 What’s Next for Mid-Day Squares?
  • 01:07:33 How to Effectively Deal with Anxiety
  • 01:09:36 What Will Your Future Self Do? 
  • 01:12:11 New Flavors to Look Forward to
...more
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Eat Play Crush with Mary ShenoudaBy Mary Shenouda

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