We were lucky to catch up with Jake Karls recently and have shared our conversation below.

Alright, Jake thanks for taking the time to share your stories and insights with us today. What’s the best or worst investment you’ve made?

Our best investment to date as a business has been in THERAPY. My partners and I (my sister and brother-in-law) are family. We didn’t become partners because we’re family but we partnered because we compliment each others skills.

When we launched the company in 2018, my partners decided that it is crucial that we protect our business partnership but also our relationship as family. So we decided to commit to go to a business therapist once per week in order to protect these fragile relationships. These were and still are mandatory sessions. The reason we committed to this investment in terms of time, resources and capital is because this is a place where we can work on becoming excellent communicators. This is a place where can have very difficult conversations but feel that it is a safe zone.

We have truly become better and more empathetic leaders from therapy. We as a business spend over $30,000 per year on therapy. The return on that investment has been 3 things:

#1 We have become better leaders and great communicators.
#2 Our partnership has gotten more aligned.
#3 We’re still in business 5 years later.

As always, we appreciate you sharing your insights and we’ve got a few more questions for you, but before we get to all of that can you take a minute to introduce yourself and give our readers some of your back background and context?

Jake Karls is a different type of business leader – unapologetically authentic, refreshingly relatable, and completely free of bullshit.

He is the Co-founder and Chief Rainmaker of Mid-Day Squares, the better-for-you chocolate brand that turned a kitchen-table dream into a multi-national household name. Mid-Day Squares is leading the disruption of an extremely competitive industry: Chocolate.

Jake’s role is to build the brand’s network and visibility. By prioritizing relationships, harnessing the power of storytelling, and being himself, Jake has cultivated the loyalties of investors, buyers, journalists, influencers, his own team, and of course, the chocolate-loving community.

Jake is recognized as a rising star in the business world. He was a finalist in EY’s Entrepreneur of the Year awards, was named to Forbes’ 30 Under 30 list for 2023 (Food and Beverage category), and is featured as a regular contributor to media outlets across North America.

How’d you build such a strong reputation within your market?

3 things helped us build our reputation:

1) Product market fit… Without this, it is extremely difficult to build a well scaled and sustainable business.

2) Great storytelling strategy… Our marketing strategy since day 1 has been to document and show everything on social media. We call it “build the business out loud”. We show the good, the bad and the ugly of how we build this chocolate business. We created a reality show on entrepreneurship on social media.

3) Leading with authenticity… When we share our stories on social media, we share the good and the bad. This transparency builds a deep trust with our fans. Makes them feel like they’re buying from a friend.

We often hear about learning lessons – but just as important is unlearning lessons. Have you ever had to unlearn a lesson?

Always be unapologetically yourself everyday. One day I started to trust my gut more…. The more I trusted it, the more I made bold decisions which lead to more opportunities. The ROI is so high, no one can be you but you. It’s what makes you different.

Contact Info:

• Website: www.middaysquares.com
• Instagram: https://www.instagram.com/middaysquares/
• Facebook: https://www.facebook.com/MidDaySquares/
• Linkedin: https://www.linkedin.com/in/jake-karls-653106ba/?originalSubdomain=ca