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Mid-Day Squares Founders Represent Gen Z's Take On Entrepreneurship

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Gabriele Hartshorne-Mehl, a Finance and Political Science student at McGill University, contributed to this story.

Mid-Day Squares is a company for the next generation. Its rainmaking strategy, social media reality show, and mandates of group therapy have redefined branding in the packaged food industry and broke ground for the company as the fastest-growing functional chocolate bar on the market.

Operations for Mid-Day Squares comprise approximately 50,000 bars per day, with $17 million CAD in fiscal revenue and annual growth of 45%. Founders Jake Karls, Lezlie Karls Saltarelli, and Nick Saltarelli are entrepreneurs affectionately known in ensemble as the “tripod.” It is no surprise that each leg of this tripod is equally successful and unconventional as the company’s brand.

Surrounded by instances of grit and perseverance from a young age, brother and sister duo Jake and Lezlie Karls grew up in a family of entrepreneurs. Lezlie left Montreal to study theater in New York City, and then worked in a kitchen as she considered a culinary career. Prior to founding Mid-Day Squares, she started her first entrepreneurial venture, designing and manufacturing clothes in a business that began in the library of Concordia University. Lezlie's list of notable clientele consisted of A-list celebrities including Rihanna, Lady Gaga, and others.

While studying to become an actuary at Western University, Jake experienced an epiphany on his apartment couch during his third year in the program.

“I’ll never forget this moment,” he says. “This Shark Tank episode came on, and I watched this guy pitch his dream. He had two mortgages on his house and kids to worry about, but he looked so free.”

Jake wanted to feel as free as this man. As a young college student with minimal responsibilities, he was in an ideal position for the hustle and grind of startup life. His first venture, a fitness business focused on outdoor boot camps, reaped significant success. With his second business, a startup catering to college parties, Jake learned the value of storytelling for brand development. As the rainmaker of Mid-Day Squares, he is responsible for growing the company’s network by fostering relationships. The serial entrepreneur was recently featured in Forbes’ 2023 edition of 30 Under 30.

Before Mid-Day Squares, Saltarelli worked as a software engineering project manager. An entrepreneur since the ripe age of 17, he learned about mergers and acquisitions from some of the best financial professionals in Montreal. Enthralled by Lezlie’s spunk, he invested in her fashion project upon their initial meeting. Saltarelli and Lezlie created the company’s first edible chocolate bar in the kitchen of their shared apartment. They now split the role of CEO. While Lezlie manages product manufacturing, development, and organizational HR, Saltarelli runs corporate relations, financials, and fundraising.

Each Mid-Day Squares founder ventured their own unique and tumultuous entrepreneurial journey leading to their current company. Does it take a particular type of person to navigate the uncertainty of startup experience?

Not really, according to Jake.

“Seeing entrepreneurship as you grow up, it actually shows you that there is no ceiling,” he says. “For me, I always knew anything was possible.”

Mid-Day Squares’ success is credited, in part, to its savvy social media strategy. Consumers in the cosmetics, clothing, and entertainment spaces select a brand based on their connection to its story and emotional experience with the company. The grocery store, however, lacks such product differentiation – consumers often opt for competitively priced or better-tasting products. With this realization, the tripod saw an opportunity for storytelling in the grocery store. Their brand aims to connect with its customers by stimulating a strong emotional attachment and, eventually, brand loyalty.

The company considers itself, in part, as a media company. Jake, who had seen success in his previous startups through the vessel of online content sharing, joined the company to oversee brand development via captivating and authentic social media.

“Social media is a forever changing landscape, but storytelling has been around for as long as humans have existed,” says Lezlie who believes it is one of Mid-Day Squares' competitive advantages.

The tripod is committed to this digital strategy. They vow to post utterly authentic content for their viewers, and such unfiltered publication has proved highly successful for Mid-Day Squares, who view their podcast as a mix of Keeping Up with the Kardashians with Shark Tank. They aim to portray behind the scenes of building a business–“therapy sessions, legal battles, raising money, things that companies never show,” according to Lezlie.

Comprised of three strong leaders with diverse mindsets and approaches, each tripod leg is distinct from the next. How do these individuals collaborate to run the company and avoid conflict?

Weekly therapy sessions have become instrumental. With assistance from a therapist, the trio navigates the complexities of running a successful business alongside the sibling drama and relationship challenges inherent in their multidimensional connection. In-house therapy is part of the company’s organizational structure. According to Saltarelli, although therapy is an extravagant investment for the business, the ROI delivered from establishing indestructible bonds between the founders and their employees has far surpassed its cost.

Lezlie strongly advocates for this peculiar addition to the payroll.

“Mid-Day Squares would not be here today if it weren’t for that level of commitment, working through difficult conversations that the average human is not ready for,” she says.

What’s next for Mid-Day Squares

“Global domination is the vision of the future,” says Saltarelli.

Mid-Day Squares recently launched a new flavour, with several more in development. These are key to their strategy, as the company’s goal is sustainable growth to continue dominating North America while maintaining product quality, food safety, and financial auditing requirements. Once they develop scale efficiency in the long term, their world-class brand will debut internationally.

As Gen Z takes over the workforce, corporate movements demanding employee diversity, improved work-life balance, and environmental social governance practices have placed enormous pressure on the traditional chief executive role. After five years of devotion to the company and each other, the tripod is an unstoppable force.

Perhaps in this new era, the tripod is the ideal candidate. Backed by the experience of turbulent entrepreneurship and a unique outlook on the corporation, they are well-equipped to tackle such challenges and catapult firms to success.

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