Jake Karls, co-founder of chocolate snack brand Mid-Day Squares, says the scariest part of launching his company wasn’t financial risk or market uncertainty — it was going into business with family. To protect both the partnership and the relationships behind it, he and his co-founders made an unusual commitment from day one: therapy sessions every 7 to 10 days, consistently, regardless of whether anything was wrong.
Nearly eight years later, Karls credits that decision as one of the most impactful the team has ever made.
A Structure Built for Honest Conversations
Sessions typically run one to two hours and cover everything from strategic disagreements to personal challenges and how each founder is showing up within the business. The goal is not crisis management but prevention — addressing tension early before it compounds into something harder to repair. Karls notes that most partnership breakdowns don’t stem from a single blow-up, but from unresolved friction that quietly builds over time.
Treating Alignment as a Business Expense
The founders list therapy as a formal line item on their profit and loss statement. Their view is that businesses routinely invest in growth strategies, hiring, and marketing, but rarely invest in the alignment of the people driving those efforts. For Mid-Day Squares, that investment has helped the team navigate high-pressure moments, make clearer decisions, and maintain trust even during periods of significant stress.
Karls is careful to note this model won’t suit every team, but the underlying principle is broadly applicable: make time to stay aligned before misalignment becomes a problem. As he puts it, businesses can be rebuilt — relationships are far har