In the very first episode of In Good Company—a podcast grounded in the belief that the best ideas don’t come from textbooks, they come from real conversations—hosts Denis Horrigan and Kevin Leahy of Connecticut Wealth Management (CTWM) sit down with longtime friend and respected business leader Chris DiPentima, President & CEO of the Connecticut Business & Industry Association (CBIA).

Chris reflects on his path from trial attorney to second-generation manufacturing CEO, and ultimately to leading one of the most influential business organizations in the country. He shares the evolution of his family’s manufacturing business, Pegasus, including stepping into leadership without formal management experience, navigating family dynamics, scaling the company from 45 to 140 employees, and making the difficult decision to sell.

Along the way, Chris opens up about what business owners rarely talk about: the weight of responsibility, the emotional complexity of family enterprises, and the identity shift that often follows a sale or major transition. The conversation also explores the realities business owners face today, from constant disruption and workforce constraints to leadership depth and global uncertainty.

Throughout the episode, one theme remains clear: business ownership can be incredibly rewarding—and at times, incredibly lonely. This conversation sets the tone for In Good Company: real dialogue, shared perspective, and a reminder that you don’t have to navigate it alone.

This podcast is produced by Connecticut Wealth Management, LLC, a registered investment adviser. This content is for educational purposes only and is not intended as personalized investment advice. Some guests on this podcast may be clients of the firm. Their participation does not constitute an endorsement of our services, and all discussions are focused on business insights rather than personal financial matters. Investing involves risk and past performance is not indicative of future results. Please consult with your financial professional before making any financial decisions.

You’re listening to In Good Company—a podcast for business owners who know the best ideas don’t comefrom textbooks, they come from real conversations.

Being a business owner can be incredibly rewarding, and sometimes incredibly lonely. This podcast was createdto change that.

Through real conversations and shared experiences, InGood Company, hosted by Connecticut Wealth Management, connects business owners navigating growth, leadership, and everything in between.