Episode 188
December 12, 2023

Making it Rain, One Square at a Time

with Jake Karls, Co-Founder and Chief Rainmaker of Mid-Day Squares

About this episode

As an entrepreneur, it can be tempting to try to master every aspect of the business, but today’s guest is proof that playing to your strengths and finding a partner with complementary skills is a winning formula. Jake Karls is the Co-Founder and Chief Rainmaker of Mid-Day Squares, a chocolate company geared to revolutionizing the snack industry. Join us as we discuss Jake’s unique path to entrepreneurship success, the decision to manufacture Mid-Day Squares in an independent factory, and the effect of digital transparency on relationship-building. Don’t miss today’s high-energy episode!

This episode is sponsored by

Exclusive Deals from Our Sponsors:

AWESOME CX by Transcom provides high-touch, personalized customer experience services to consumer brands of any size! Email Lee at lee@stairwaytoceo.com to learn more about their award-winning services and Awesome Coffee Chats. 

In This Episode You’ll Hear About:

  • [02:21] Lessons of hard work and resilience he learned from his entrepreneurial father. 
  • [10:12] Jake’s first foray into entrepreneurship; running an outdoor boot camp. 
  • [12:10] Co-founding Mid-Day Squares with his sister and brother-in-law in 2018.
  • [20:51] Defining the roles and navigating the relationships behind the business.
  • [24:09] A year-by-year look at the growth behind Mid-Day Bars since its inception. 
  • [28:13] How transparency has supported the fundraising process.
  • [33:10] What happens when envy and insecurity affect our attitudes toward others.
  • [36:39] Jake’s two experiences with burnout and his recovery process. 
  • [40:06] The story behind Mid-Day Bars.
  • [42:21] Advice for aspiring entrepreneurs and a glimpse into the future of Mid-Day Bars.

To Find Out More:

Jake Karls on LinkedIn 

Jake Karls on Instagram 

Mid-Day Squares

Lee Greene on LinkedIn

Awesome CX

Stairway to CEO

Stairway to CEO on Instagram


“I know [that] anything is possible as long as you work hard and you have that resilience, that grit and love and passion for what you do.” [0:03:36]

“If you work hard and put your effort and love into something, you have a chance of winning in that field.” [0:05:45]

“Through my [first] five years of entrepreneurship, I learned not to do what I’m really bad at, and to do what I’m really good at [instead].” [0:12:51]

“When you are yourself, truthfully, you are your best version and you are unstoppable because nobody can actually be you.” [0:16:30]

“Our strategy was simply not to talk about the product on social media, but to share the journey of how we built this business.” [0:24:32]

“We build out loud.” [0:28:57]

“I feel like I’m playing the game better than I ever have before because I lost that ability to be – envious or judgemental.” [0:35:35]

“My advice is block out the noise and be yourself.” [0:42:23]

“Being yourself is a superpower.” [0:42:43]

“We’re doing it by being ourselves which means that you can do anything by being yourself as well.” [0:43:20]

Read the transcript

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