Family Business Insights

Given the unique advantages of Employee Stock Ownership Plans (ESOPs), it’s not surprising they are increasing in popularity. However, one surprising trend we have observed is an increasing number of owners of family-owned businesses considering an ESOP as an ownership transition tool. The difficulty of transitioning a family business to the next generation is well-documented […]

Look at any standard corporate organizational chart, and you will see a clean, geometric hierarchy of boxes, lines, and titles. It looks orderly. It looks predictable. But anyone who has actually sat in a leadership seat knows that the real day-to-day experience feels less like a clean blueprint and more like driving a vehicle down […]

As healthcare costs rise and employee expectations evolve, employers face growing pressure to balance cost control, compliance, and well-being. These challenges were at the heart of the recent Conway Center webinar featuring USI Insurance Services on the 2026 Employee Benefits Market Outlook. Why the Landscape Is Changing Organizations are moving beyond traditional fully insured health […]

Most leaders quietly carry a dangerous misconception: they believe that a healthy company culture means a conflict-free workplace. The reality is actually the exact opposite. If your organization has zero friction, it usually means people are too comfortable, or worse, they are suffering from “artificial harmony”-smiling in the boardroom while the real, messy decisions happen […]

For more than a century, Chelsea Milling Company has been an enduring presence in American kitchens. Best known for its iconic Jiffy Mix products, the family-owned business has thrived across generations thanks in no small part to the unconventional leadership journey of Howard “Howdy” Holmes. Holmes’ story doesn’t follow the typical path of a family-business […]

In a family business, culture is often treated like a piece of antique furniture-something we’ve inherited, something we value, but something we rarely think about reupholstering. But if you aren’t actively designing your culture, it is being formed by default. “Default” culture is what happens when you let old habits, unaddressed tensions, and “the way […]

Succession planning isn’t only about preparing the next generation – it’s also about preparing the founder to step back with confidence. For many founders and senior leaders, stepping back from the family business can feel exposing and unmooring – even risky. How do you walk away from something that represents years of work and sacrifice? […]

The statistics are a wake-up call for any family legacy. According to the Family Firm Institute, only 30% of family businesses successfully transition to the second generation, and a mere 12% survive to the third. While many assume these failures are due to poor financial planning or market shifts, the reality is far more personal. […]

The year 2026 isn’t just another date on the calendar for family businesses; it’s a rapidly approaching crossroads. While the world outside our walls accelerates with AI, new market demands, and a shifting workforce, many family enterprises find themselves caught in a familiar trap: the relentless cycle of firefighting. You know the drill: urgent emails, […]

Let’s cut right to the chase: When was the last time you truly stopped? Not just stopped working, but stopped thinking about the market, the payroll, or the next family board meeting? In the world of a family business, “busy” is a badge of honor. You’re constantly moving, making decisions, balancing legacy against profit. Taking […]