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Interview with Jake Karls | Cofounder and Chief Rainmaker at Mid-Day Squares

Jake Karls is the Co-Founder and Chief Rainmaker of Mid-Day Squares, one of the fastest growing chocolate manufacturing brands in Canada and the United States.

Interview with Jake Karls | Cofounder and Chief Rainmaker at Mid -Day Squares | The Business Anecdote
Jake Karls: Photographed by Dominic Lachance

Before becoming an Entrepreneur his dream was to become an Actuary or Investment Banker. After graduation and several job interviews, he was unsuccessful in securing a job. While watching a Shark Tank episode, Jake became inspired to explore a career path as an Entrepreneur because of his desire to be an outlier, and unapologetically himself.


Jake’s first stint as an Entrepreneur was as the Cofounder of “Chase and Hunter”, a clothing brand. He would later join his sister and her husband in cofounding Mid-Day Square, and is in charge of building the company’s network, brand and community. In our interview with Jake, we explore his entrepreneurial journey and the secret to Mid-Day Squares' success.


Hello Jake. Thank you for participating in this Q&A session. Please give us an overview of your background before you became an Entrepreneur?

Jake: Before becoming an Entrepreneur my dream was to become an Actuary or an Investment Banker. My focus was to make my parents proud and to get a job that paid well. I wanted to prove to everyone that I could follow one of the hardest career paths out there… I thought life was all about going to college, getting a degree and then getting a well paid job. I struggled through school but when I finally graduated I realized I wasn't living life for me, I was living life for others... Doing everything for everyone else and following the standard rules of life. After graduating I applied to every bank and insurance company, but not one of them even gave me a second interview. I realized that was a success because in those interviews I stayed true to who I am, followed my gut and was unapologetically myself.


What originally attracted you to Entrepreneurship as a career path?

Jake: I was jobless while everyone around me was getting great jobs... I felt discouraged. One night I was sitting on the couch flipping through the TV channels and I decided to watch Shark Tank. In that moment, I was fascinated by the entrepreneur on the screen. The guy was pitching his dream to the sharks. His energy was so fun, his passion was truly admirable and most importantly he looked like he was so free... Free of the pressure of following the herd of society. Free of doing what everyone else is doing. He was an outlier.... In that moment, I made a promise that no matter what happens I will be an outlier too. So I decided in that moment that I will actively dabble in entrepreneurship.

Interview with Jake Karls | Cofounder and Chief Rainmaker at Mid -Day Squares | The Business Anecdote
Jake Karls: Photographed by Dominic Lachance

Has your entrepreneurial journey been influenced by any past or present business leaders?

Jake: Phil Knight - Inspired by the storytelling Nike continues to do. Hunter Harrison - They call him the railroader. Inspired by his operational excellence with margin optimization. Elon Musk - Inspired by his boldness.


What do you attribute your success to as an Entrepreneur?

Jake: My superpower as an Entrepreneur is the ability to make people feel something deep inside, the ability to spread good energy in the world and most importantly to show people that you can win by being unapologetically yourself.


What’s the origin story behind Mid-Day Squares?

Jake: We recently updated our story because we were tired of hearing the same story most new CPG (consumer packaged goods) companies tell: “I made a thing in my kitchen because I wanted something that didn't exist and so here we are.” Although that story is true for us, we just decided we were done telling it that way. We all grew up on the same chocolate bars which have been the same for the last 100 years. Nothing wrong with that. We just feel it's time for a new brand to become a household staple for you all. One that just hits different when you eat it. So that's what we did.


We’re three family members and die hard entrepreneurs. Lez, Nick (her husband), and Jake (her brother). We aren't doing this together because we're family members. We're doing this because we are the right trio with the right skill sets to make it happen. We're building something loud. Something you’ll love because of the vibe and how good our chocolate makes you feel.


Since launching in our condo in 2018 it's been a wild ride. Ups, downs, you name it. We've since had to build a manufacturing plant that outputs 90,000 chocolate squares a day, and is growing. We operate pipes that transport chocolate, which turns into epicness that shows up in your hands as a beautiful delicious functional chocolate square. We want to be the company that is celebrated for being bold and making our fans happy.


We have a dream and we won't stop until we accomplish it. Every fridge in North America should at some point have Mid-Day Squares in it. We think you’ll f*kin love them. If you haven't watched our journey yet, we think you should. Check out our real behind the scenes content of us attempting to build this massive chocolate company while being ourselves unapologetically.


After graduating I applied to every bank and insurance company, but not one of them even gave me a second interview. I realized that was a success because in those interviews I stayed true to who I am, followed my gut and was unapologetically myself. - Jake Karls
Interview with Jake Karls | Cofounder and Chief Rainmaker at Mid -Day Squares | The Business Anecdote
Jake Karls: Photographed by Dominic Lachance

What’s the unique value proposition of Mid-Day Squares?

Jake: We created the first functional chocolate bar: A chocolate bar that tastes epic, with super clean ingredients, high in protein, high in fibre and satisfies hunger for up to 3 hours. We're making the best afternoon snack by marrying indulgence with function.


Please outline the roles and responsibilities of each Mid-Day Squares Cofounder?

Jake: Lezlie Karls is the Cofounder and Co-CEO of Mid-Day Squares. She leads the companies manufacturing, R&D and media. Nick Saltarelli is the Cofounder and Co-CEO of Mid-Day Squares. He's in charge our systems, operations, customer acquisition and finance. Jake Karls (me) is the Cofounder and Chief Rainmaker of Mid-Day Squares. I am in charge of building the network, making noise for the brand and building our brand's community/fan base.


What key challenges have you and your Cofounders faced running Mid-Day Squares?

Jake: The biggest challenge has been figuring out how to scale our chocolate bars. We visited 26 different Co-manufacturers across North-America... Not one was able to make our product at scale. So we were given two options: Either we change our product to be like everyone else's. That is, be like the herd. Or we build our own custom chocolate factory. So we chose to build our own factory.


Over the last three and a half years we built a custom line that continues to challenge us everyday. We're proud to say that our factory is currently 95% automated and can produce upto 90,000 bars per day from only being able to do 80 bars per day when we started in August 2018.


My superpower as an Entrepreneur is the ability to make people feel something deep inside, the ability to spread good energy in the world and most importantly to show people that you can win by being unapologetically yourself. - Jake Karls

In 2019, Mid-Day Squares sold their products in zero US stores. By 2022, Mid-Day Squares had their products in 2500 US stores. As a Canadian company, what’s the secret behind your market penetration in US and general business growth since 2018?

Jake: Two things: Build out loud … and, Build in public. We document and share everything we do, which includes the good, the bad and the ugly of building this business. Retailers love the transparency and the storytelling. By creating the first functional chocolate bar, we have a clear Product/Market fit which is also innovative.


Do you have any advice for new or aspiring entrepreneurs trying to launch or run a startup?

Jake: Get comfortable with feeling uncomfortable. Learn to put yourself in zones of discomfort because that is where the magic and serendipity happens.


Before we conclude this interview please tell us what branding strategy is used by Mid-Day Squares?

Jake: We created a reality show on entrepreneurship... Showing our consumers the entire journey: The good, the bad the ugly of building this brand. We publish this reality show through social channels on our Linkedin, Instagram and Tiktok. We show legal battles, therapy sessions, raising money, machine breakdown drama etc... The goal is to really bring the consumers on the journey with us. We want them to feel like they know us, feel like they're a friend, neighbour or family member. We're focused on building fans not just customers.


We would like to thank you for participating in this Q&A session. We wish you all the best in your future endeavours.

Jake: Thank you and LFG.


Get comfortable with feeling uncomfortable. Learn to put yourself in zones of discomfort because that is where the magic and serendipity happens. - Jake Karls
Interview with Jake Karls | Cofounder and Chief Rainmaker at Mid -Day Squares | The Business Anecdote
Jake Karls: Photographed by Dominic Lachance

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