How Mid-Day Squares Turned Painful Mistakes Into Momentum with Jake Karls

In this energizing episode of Pivot to Profit, host Pam Jordan sits down with the electric and relentlessly authentic Jake Karls, co-founder and Chief Rainmaker of Mid-Day Squares. What unfolds is a masterclass in entrepreneurial grit, radical transparency, and the surprising power of “delusional belief.”

Jake opens up about his unconventional path—from dreaming of being an NHL goalie to becoming a chocolate entrepreneur alongside his sister and brother-in-law. Far from a straight line, his story winds through academic struggles, early anxiety about money, and the bold leap into a family-run startup launched out of a condo kitchen. Their early goal? Sell $250,000 of chocolate bars in year one. Their reality? They blew past that number in just a few months, thanks to momentum Jake calls “an unstoppable force when fueled by belief.”

But success didn’t come without painful tuition. Jake shares the infamous UPC code disaster—when a tiny packaging mistake on millions of bars led to products that couldn’t scan, lost sales, frustrated retailers, and a million-dollar revenue drop in a single month. That oversight? A $30 validation step they skipped. It’s a brutal reminder that in entrepreneurship, the smallest details can become the biggest financial hits.

Jake also reveals another costly lesson: failing to buy the Canadian domain for Mid-Day Squares. A $60 decision turned into a $20,000 fix years later. For him, it solidified a core principle: pay attention early or pay exponentially later.

Beyond the financials, Jake speaks passionately about alignment, therapy-powered partnership, and the role relationships play in building a resilient business. As Chief Rainmaker, his KPI isn’t just revenue—it’s the friendships and trust he cultivates long before a transaction ever happens.

Ultimately, Jake defines financial success simply: freedom to continue living his mission. Money, he says, is a tool to support wellness, longevity, and the ability to keep showing up—physically, mentally, and entrepreneurially.

This episode is a must-listen for founders who need both inspiration and a reality check. Because as Pam reminds us, it’s not what you make that matters—it’s what you keep.