How Mid-Day Squares are building a $100M Brand Through Authenticity and Fearlessness

“No one in history has ever done anything great by following how it’s always been done.”

We were thrilled to speak to Nick Saltarelli, co-founder of Mid-Day Squares, one of the most exciting challenger brands in food today. He shared how the company grew into a $100M business by breaking every rule in the book.

Here are the key lessons from their journey.

1. Lead with Authentic Communication

“There’s a lot more room in today’s day and age for authentic communication.”

Mid-Day Squares doesn’t just share their wins. Their tagline says it all:
“Follow us to watch us become one of the biggest chocolate companies ever, or crash and burn. We’re still not sure which one it’ll be.”

That honesty is their superpower.
They let fans experience the highs and lows of building a business in real time, making their audience feel part of the journey.

The result is a community that’s emotionally invested in the brand, not just the product.

Lesson: Vulnerability is one of the most powerful brand-building tools you have. When people relate to your story, they’ll root for you.

2. Take Inspiration from Unlikely Places

From Elon Musk to Dragon’s Den to The Kardashians, Mid-Day Squares combines charisma, transparency, and showmanship.

By lifting the curtain on business and sharing everything, both personal and professional, they have turned brand-building into entertainment.

Lesson: When done well, radical transparency can replace traditional marketing.

3. Act Like a Music Band

“We act like a music band, but instead of selling records we sell chocolate.”

Mid-Day Squares doesn’t just build customers. They build fans.
Their approach mirrors that of musicians, creating an emotional connection through story, energy, and consistency.

Lesson: Build brand fandom, not just brand awareness.

4. Invest in Connection

In the early days, every DTC order came with a personalised Polaroid photo. When that became too much, one of the founders’ mums took over and began writing handwritten notes. She has now written more than 600,000 of them.

It’s proof that you don’t need a big budget to make people feel seen.

Lesson: Small gestures build big loyalty.

5. Choose Un-Average Inputs to Create Un-Average Outcomes

Mid-Day Squares launched into the refrigerated chocolate category, one of the hardest spaces in retail.
By choosing a difficult path, they created their own lane where competitors couldn’t easily follow.

Lesson: When you do the hard things, you get to write your own rules.

6. Be Fearless

Building something new means being willing to lose it all.
Nick believes that true creativity comes from boldness, not fear. When leaders operate with courage, that energy flows through the entire business.

Lesson: Fear-based decision-making kills innovation. Confidence creates culture.

7. Lean Into What Makes You Un-Replicable

Mid-Day Squares can’t compete with the big four chocolate companies on production or distribution.
But they can be the best in the world at making people feel something, and that is their edge.

Lesson: Figure out what makes your brand irreplaceable, then double down on it.

🎧 For more inspiration, listen to the full episode on our Podcast page.

‍

‍