Success Leaves Clues: Ep 306 - How to Build a Brand Through Storytelling and Relationships with Jake Karls
Episode Details

What does it take to turn a homemade snack into a brand stocked by more than 11,000 retailers?


In this episode of Success Leaves Clues, Robin Bailey and guest co-host Christine Vigna sit down with Jake Karls, co-founder and rainmaker of Mid-Day Squares. Jake launched the company in 2018 with his sister Leslie and brother-in-law Nick, making bars in a Montreal condo kitchen and delivering orders themselves.


Jake shares how inviting customers behind the scenes helped the founders build a community around the brand. He recalls an early turning point when Mid-Day Squares reached its first-year sales goal of $250,000 in just three months. Today, he says the company’s Montreal facility produces roughly 170,000 to 175,000 bars a day.


The conversation explores why Jake stepped down as CMO after realizing management was not his strength. As Mid-Day Squares’ rainmaker, he now focuses on storytelling and building relationships that can lead to retail, investment, hiring, and other opportunities over time.


Jake also speaks candidly about the burnout that forced him to reconsider his pace. He explains why rest is now part of how he sustains his work, and how regular therapy sessions help the three founders navigate difficult decisions while protecting their relationship as family.


You’ll hear about:

  • How Mid-Day Squares grew from hand-delivered samples to thousands of retail locations 
  • Why the founders chose to share the difficult parts of building the company 
  • What a personal response to a customer problem can mean for a brand 
  • Why Jake stepped away from the CMO role and became the company’s rainmaker 
  • How long-term relationships have helped Mid-Day Squares find partners and investors 
  • What burnout changed about Jake’s approach to work and rest 
  • How the founders use regular therapy sessions to communicate through conflict 
  • Why Jake wants the next generation to feel confident sharing their own stories


We talk about:

00:00 Christine’s customer experience and Jake’s personal response 

04:31 The early days of Mid-Day Squares in a Montreal condo 

09:00 The founders’ belief in the business and an early sales milestone 

11:47 Why the company shares its entrepreneurial journey openly 

12:18 Jake’s experience with burnout and the lesson he learned about rest 

21:35 Why Jake moved from CMO to the rainmaker role 

23:07 Building friendships and business relationships over time 

29:16 Working with family and addressing conflict 

30:07 Why the founders committed to regular therapy sessions 

38:14 The legacy Jake hopes to leave through Mid-Day Squares


Connect with Jake

 

Connect with Us 


Episode cover art for Success Leaves Clues: Ep 306 - How to Build a Brand Through Storytelling and Relationships with Jake Karls
00:00
30:00