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).
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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.
Episode 1 Transcript:
Denis Horrigan: Hello everyone! Welcome to In Good Company. This is a podcast that Kevin Leahy—my colleague and partner here at our firm, Connecticut Wealth Management—and I are putting together. It’s really designed for business owners. We’re going to have a lot of guests who are either business owners or work with business owners.
The idea is for folks to learn from each other. We’re trying to create a community of business owners—which Kevin and I are, too—where we can share experiences, discuss challenges and opportunities, and really try to help each other out.
Today, we’re very excited to have a longtime friend, Chris DiPentima, who many of you are probably familiar with. He’s somewhat of a celebrity in this state. Many of you know him as President and CEO of the CBIA, but many may not know his backstory or what he did before CBIA. It’s very impressive, and I’m excited for everyone to learn about it.
Before we kick it off, Chris, I’d love for you to talk about the CBIA, what your role is there, what you do on a day-to-day basis, and what CBIA is.
Introduction to the CBIA
Chris DiPentima: Thank you both for having me. Great to see you, Denis and Kevin. You’re not only colleagues, but, as you mentioned, friends, and I’m so grateful to have you engaged to CBIA.
Many folks don’t know that CBIA is one of the largest—and probably the oldest—business associations in the country, not just in Connecticut. We celebrated our 210th year in business back in November 2025, and it’s a relatively complex organization. I didn’t fully realize how complex it was before joining, even though I had been on the board and a member for several decades. Because of the age of the organization and the breadth of our membership—with thousands of members across the state, representing a variety of industries and business sizes—a 60-person organization is fairly complex.
We have five entities within CBIA, as well as two strategic partners: CONNSTEP and ReadyCT. The way I describe CBIA when I have just 30 seconds with someone is that it’s like a three-legged stool supporting Connecticut’s economy.
The first leg is advocacy. CBIA has been advocating on behalf of the business community since 1815, when business leaders came together in Middletown, CT, to support more industrial development in the United States.
The second leg is the products and services CBIA offers to members to help reduce costs and stay competitive. CBIA has been doing this for about 50 years, since the 1980s. More recently, we’ve expanded our events and networking opportunities so businesses can learn best practices. This area has really grown over the last five years.
The third leg is the CBIA Foundation, which we launched about two years ago. It’s a 501(c)(3) organization that conducts economic research comparing Connecticut to other states in a variety of categories.
Kevin serves on the CBIA Foundation Board, and Denis recently joined the CBIA Advocacy Board. It’s great to have you both engaged in two of the three legs of the stool. You both often participate in our events and use some of our products and services, so you understand the breadth of CBIA—but not everyone realizes how those three legs come together to support the organization.
Early Career & Avoiding the Family Business
Kevin Leahy: Chris, thank you. That’s awesome. I have the good fortune—as I say all the time—of knowing you since nursery school. And, of course, I should clarify—not our nursery school, but our kids’ nursery school. So I got to know you a bit earlier in your career, certainly before your time at CBIA, when you worked for a very large multinational company and so forth.
I don’t want to tell your story for you, but this podcast is really about entrepreneurs and business owners and their journeys. And I don’t know that there’s a better person to help us kick this off than you, who in many ways represents all of us—big and small—on that journey.
You yourself have been an entrepreneur, and I’d love to hear you tell the story about how you got involved in entrepreneurship way back when, even before that. And, if I remember correctly, you claim to have been an attorney and actually passed the bar—is that true?
Chris DiPentima: That’s a claim I’m sticking with, based on some of the certificates behind me, Kevin. I don’t know how I got through law school. I actually went to law school to make sure I didn’t get involved in the family business. My dad was a real serial entrepreneur—he bought and sold several businesses throughout his life.
Then in 1989, he started a manufacturing company by buying the assets of a struggling business. My older brother joined him shortly thereafter, and all I heard at the dinner table during the nineties was about the family business. I thought, there’s no way I’m getting involved, even if I had the opportunity.
So I went to law school. I came back, attended Quinnipiac Law School—which brought me back to Connecticut—and practiced law for about eight years, mostly in litigation and trial work. During that time, I had the opportunity to represent several businesses, many of them family owned.
I really admired how they were making a tangible impact on their communities, whether it was a local hardware store or a manufacturing company in Waterbury. My role was offering guidance, advice, and counseling as a lawyer, but there wasn’t a tangible asset or direct impact for me personally. I appreciated the effect they were having through the events I attended and the work they were doing in their communities.
That drew my interest, and when the opportunity came to get involved in the family business, I decided to say yes. There was probably some entrepreneurial spirit in my DNA, given my father’s background. Ironically, I went to law school to avoid the family business—but eventually, it brought me right back to it.
Kevin Leahy: And if I remember correctly, you ended up running it, you ran the business and ultimately sold it. You were the guy at the top.
Chris DiPentima: Yeah. I joined them in 2001 and learned my way through the organization. I started by overseeing HR and a new business they had acquired, then expanded to oversee the finance side of the business. Eventually, I became vice president of operations, running the operations and supply chain functions.
Four years later, in 2006, I took over for my dad and became president and CEO of the family organization, working with a lot of great outside people as well as our internal staff. My older brother and I grew the business quite a bit, and as you mentioned, we ended up selling it in 2016 through a process we ran ourselves.
We were looking for a strategic buyer who could take the business to the next level while maintaining the culture we had built—the family-like atmosphere. It was interesting trying to thread that needle, but I think we found the right suitor. In 2016, we sold to Leggett & Platt, which is headquartered in Missouri and is publicly traded.
Overnight, I went from a small, privately held family business to learning things like SOX and inventory compliance—fun accounting stuff that you two appreciate—and became part of a large, healthy, publicly traded company. I stayed there for almost five years before joining CBIA.
Kevin Leahy: Boy, if I had a nickel for every time Denis tries to talk about inventory compliance—my goodness.
Denis Horrigan: It’s either that or Sarbanes-Oxley. It’s just fascinating, really.
Lessons Learned Running a Family Business
Kevin Leahy: Chris, sorry—before we move on, go back to when you were an attorney, learning a new business that you had heard your dad and brother talk about over dinner, and ultimately ended up running it. What sticks out—maybe a memorable lesson?
What were the struggles and challenges? We all have them. There’s a certain glory if you succeed even a little in business, but the struggles are real. As you think back to that family business, I imagine you were learning some serious lessons in real time.
Chris DiPentima: Yeah, it was really interesting. When I became a lawyer, the first law firm I worked for had a boss who believed in trial by fire. I passed the bar in the first week of June, and literally two weeks later, he had me co-chairing a trial. I was thinking, “I just passed the bar!”
Going into the family business was similar trial by fire. I had never run a company before, never managed people. As a law firm associate, I had worked collaboratively with a team on trial preparation and execution, but I hadn’t managed people, handled a P&L, or worked with finances.
It was definitely a trial by fire, but we had a great group of people supporting the manufacturing company—lawyers, accountants, and other experts. Because of my inexperience, I was a big believer in bringing in outside experts, whether it was consultants to help with lean practices or creating a board of advisors for guidance. I also relied on a personal executive coach for myself and the team. Those were the people I gravitated toward.
I think the biggest challenge for me when I first led people at Pegasus, our family manufacturing company, was that I wanted everyone on board with every change. We aimed for 100% buy-in on every decision, and it probably took me too long to realize two things: one, you usually aren’t going to get everyone on board; and two, you don’t need 100% buy-in to make change.
There’s what they call the “mighty minority”—a group of change agents who help move things forward. The rest are either neutral or resist, but that core group is enough to drive change. That was one of the biggest lessons I learned early on.
The other lesson was realizing that I didn’t need to know everything or be the expert on everything. I had to rely on outside experts for guidance and trust the team to develop their expertise. Those were probably my two biggest lessons when I first became a leader and then CEO.
Denis Horrigan: What was the size of Pegasus when you first joined and when you left? What was the size difference?
Chris DiPentima: When I first joined, there were about 45 employees across three divisions, three separate companies my father had acquired and bolted on. By the time we sold in 2016, about 14 years later, we had grown to roughly 140 employees.
Denis Horrigan: Yeah, it’s hard to gain consensus with 140 employees. Sounds like that leadership was a real baptism by fire. You learn that you can’t always get everyone on board—whether it’s 40 or 140 people, you just have to lead. I think that’s part of the entrepreneurial story.
Being a business owner can be lonely. You have to make some of those decisions on your own and ask people to follow you.
Chris DiPentima: You’re absolutely right. I read a great book—actually, CONNSTEP had an event when I was at Pegasus, and they had a speaker who was involved in 9/11 and the reopening of the New York Stock Exchange after that day. In his book, he talks about the 95-5 rule: 95% of the time, he tries to get consensus and buy-in from his leadership team, but there’s always that 5% where he just has to make the decision, and they’re expected to follow.
Selling the Business & Emotional Complexity
Denis Horrigan: So eventually, Chris, you and your brother sold the family business. Was that always the plan? Was that your dad’s idea back in the day—to build it and sell it? Or what brought you to the point where you said, “You know, I think now’s the time to sell”?
Chris DiPentima, President & CEO of CBIA: Yeah, it wasn’t a plan from the beginning. My dad was always bringing people in to give valuations of the business, but deep down—if you know my father—he probably saw it as a legacy business, something that could survive multiple generations. My older brother and I felt the same way.
We were actually more against selling or seeking valuations than my father was. We were focused on running the business and likely passing it to the next generation. Over time, though, things evolved. In the last couple of years before we sold, we had a lot of conversations about where we were taking the business. Could we take it to its true potential?
We often talked about “taking the governor off the engine”—removing limits on growth—but that requires both cash and human capital, and family businesses are sometimes limited in that regard. We also didn’t have a great plan for the third generation to come in. We discussed getting our nephews involved, but there weren’t clear rules about working elsewhere before joining the family business. We knew that was something we’d have to grapple with.
Over a couple-year period, we decided to take a shot at selling the business. We had reached a point where we could maximize its value and also address the third-generation challenge. We ran our own process, identifying about 10 strategic buyers who we thought could take the business to the next level.
We had three rules: first, the buyer couldn’t be located in the Northeast, because we didn’t want them micromanaging the business. Second, they had to be well-capitalized to support growth. Third, we wanted some synergies, whether in market expansion, sales growth, or supply chain.
Leggett fit the bill—they were vertically integrated in the aerospace market we were operating in—and they ultimately came out on top of the 10 buyers we had identified.
Kevin Leahy: Chris, looking back, were those the right requirements? If you had to do it over again, did you bring in the right people? Did you qualify the right 10 firms at the end of the day?
Chris DiPentima: Yeah, I think we did. We were probably a little too skittish about closing off the Northeast. If I were to do it over again, Kevin, and had the right people and structure in place, I’d feel comfortable enough that there wouldn’t be micromanagement. So, if I were to change one thing, it would be not limiting ourselves geographically.
In today’s world, you can be anywhere in a couple of hours, sit in someone’s conference room, and manage things remotely if needed. So, I probably wouldn’t have restricted it to the Northeast. But even with that, I think we still would have ended up selling to Leggett when it was all said and done.
Denis Horrigan: So, you had 140 people, Chris, that you were responsible for—the employees and their families. That’s a pretty significant responsibility. How much did that weigh on the ultimate decision to sell the business? That must have played a pretty big role.
Chris DiPentima: A huge role, Denis—no doubt. We talked a lot about preserving the culture with a strategic buyer versus, say, selling to private equity. We even considered an ESOP—a employee stock ownership plan—where the employees would own the company, because that’s one way to preserve the culture in a strong way.
I’d say ESOPs in 2016 probably weren’t as prevalent as they are today, but the employee impact was huge and definitely a top priority. The first-generation impact—the effect on my father—was also important. We wanted to make sure this was what he wanted, because, again, it was a legacy business.
Denis Horrigan: So, Chris, we do a lot of work with business owners, especially those thinking about succession or transitioning out of the business—selling at some point in their career. We find that many people enter that conversation without knowing what other options are.
You just mentioned an ESOP. A lot of people hear “ESOP” and say, “What’s an ESOP?”—they can’t even spell it! What do you wish you had known earlier before the process started? Whether financially or emotionally, was there anything you wish you’d known before beginning the process of identifying those 10 potential buyers?
Chris DiPentima: I wish I had better understood the emotional impact on the first generation. As I mentioned, knowing who we eventually sold to—and realizing that many of the companies on our list of 10 were publicly traded—I wish I had better understood the transition from private to public. It’s not insurmountable; we were successful, but it doesn’t happen for a lot of organizations.
Talking to a few privately held companies that became public overnight, we saw that while we maintained the culture and did a great job, the processes and compliance requirements are a whole different game when you move from privately held to public.
I also think that with better planning, we could have maximized more of the earnings and really improved the bottom line. But honestly, for us, it wasn’t all about the money—we didn’t even choose the top bidder. It was more about maintaining the culture, quite honestly.
Kevin Leahy: Chris, we talk about this all the time—identity and the concerns that come with selling a business. People often regret selling their business. There are studies and surveys that show that many entrepreneurs later feel regret for various reasons.
Did you experience an identity crisis at all? Going from being an entrepreneur to—well, I don’t want to downplay it—you had a pretty significant role at Leggett, but were you just another employee? How did that feel? How did you handle that transition?
Chris DiPentima: Yeah, I will say that selling the family business—how I thought about it—was that you’re selling a shared sense of legacy. Your professional life is tied to much more than results. It’s tied to the people who work for you and their families.
As a second-generation owner, you’re preserving the legacy of the first generation, continuing their dream and vision. There’s pride in working in a family business and trying to carry that legacy forward. So, when you sell the business, you are, in a way, selling a sense of that legacy—walking away from shaping that business.
I’m fortunate that I didn’t fully realize this would happen. As you both know, when we sold in 2016, a lot of those same traits exist at CBIA. Looking back, I see the drive for vision and the pride here—it feels as much, if not more, like a family business. We’re preserving a 210-year legacy at an organization that’s been around since 1815.
There are traits I didn’t fully appreciate until after I came on board, and it makes me still feel that pride and connection to the shared legacy of the family business we sold.
Kevin Leahy: Yeah, I’ve got to say, Chris—and I mean this sincerely, not just because we’re doing this podcast—I’m not sure I fully understood this when you took the job. But over time, I’ve recognized that you’re there to help the big companies just as much as the small ones.
The fact that you have experience in family-owned businesses and manufacturing, and also part of a very large firm, your background almost seems perfect. It really does.
Denis Horrigan: Yeah, because a lot of your constituents at CBIA are family-owned businesses—you walk the walk. And then the other folks you’re dealing with, the legislature, you’ve got a bunch of lawyers around you, and you’re a lawyer. I’m with you, Kevin. When you originally took the job, I thought, “Oh, that’s interesting,” but it really is perfect.
When you sold, I’m intrigued by that whole journey—going through the process of selling and then landing in the new role. Do you remember missing something? Was there something you didn’t anticipate? Kevin kind of touched on the emotional part—on Friday, you were the CEO; on Monday, you’re Chris.
That’s something you might have missed, but was there anything else? And how about something you didn’t miss when you sold?
Chris DiPentima: Yeah, I didn’t really miss much, I’d say. Family businesses have interesting dynamics. There’s a certain emotional weight and complexity that comes with them, especially as a second-generation owner. You’re often compared to the founder. In my case, that was internally, with the family and employees, but also externally. I was very active with the Chamber and CBIA, and people would often say, “Hopefully you can live up to your dad,” who was a serial entrepreneur and a remarkable person.
Family businesses also involve different visions—from people working in the business, my older brother, the third generation coming in, or siblings not involved in the business at all who might want to participate. I made a lot of changes compared to my father. I brought in consultants, third-party advisors, and implemented transparency with metrics. We rolled out a profit-sharing program, sharing financials with employees so they could see how we were doing.
Sometimes I questioned: Am I honoring my father’s legacy, or am I changing too much? Decisions in a family business often feel very personal, even when they’re not. You try to put the business first because if the business does well, the family does well. If you put the family first, the business might suffer, and then everything can break down.
That was the toughest part—the emotional complexity that comes with running a family business. I didn’t have an issue walking away from the stress, politics, or emotional weight, but the biggest challenge was that when you sell, you’re handing over a piece of your family story to someone else. Even if it’s the right decision, that feeling lingers long after you sign the paperwork.
Sometimes I drive by the company—or even visit, since they’re a CBIA member—and I see that the legacy is different. It’s a different organization now, with many different employees. That, Denis, was the hardest part.
Challenges Facing Business Owners Today
Kevin Leahy: Chris, if you take your CBIA hat off for a minute—sitting back at Pegasus or just talking with a couple of business owners like Kevin and me—what are the challenges that most medium-sized business owners are facing today? Is it very different than in 2016 or 2014? If you go back a decade or 15 years, when you were still at Pegasus, would the issues have been the same, or are they different now?
Chris DiPentima: I think some of the issues are the same. Kevin, we’ve been talking about workforce challenges in manufacturing since coming out of the Great Recession, around 2010–2011. Federal uncertainty has always been a factor, though it looks different today. I remember during the Obama administration, there was sequestration—cuts in defense spending—and that created uncertainty. Globalization was another major issue: how do you compete in global markets? So while the types of uncertainty differ, uncertainty has always been present at both the federal and global levels.
The biggest change I see today is the speed of cycles. Disruption now comes faster, which is both an opportunity and a challenge. You can create opportunity from it, or you can get overwhelmed. Just looking back five years at CBIA, as an owner of this organization, I’ve seen one challenge after another: COVID, workforce issues, rising labor costs, supply chain disruption, federal uncertainty, interest rate increases, tariffs… one cycle after another every six to twelve months. AI and technology now add even more disruption.
If you look back from 2010 to 2020, major disruptions happened every two to three years. Now, it feels like it’s happening much faster. As a result, I’ve learned—and I’ve been preaching this since my time at Pegasus—that as a CEO, executive, or even a first-line supervisor, you need to spend a lot of time outside your business: learning best practices, paying attention to news and social media, and listening to podcasts to stay abreast of changes and how to navigate them.
I’ve always been a big believer in spending time outside your four walls, and that advice is even more critical today. But at the same time, you also have to be present internally and engaged with your team.
Kevin Leahy: Awesome advice. So say more about that, Chris. Social media and reading the news—that’s fine—but how else do you do it? How would you suggest people spend their time? Face-to-face, one-on-one—who should Denis and I be talking to? Or manufacturers like you once were—who should they be connecting with?
Chris DiPentima: Yeah, and I think that’s why our events have grown so much. Kevin, when I first started here, we had about 20-something events. This year, we’re doing 65—both in person and webinars. It’s not just the number of events or the attendance—though over 9,000 people attended last year—it’s the content and the networking that happens.
You get to talk to another business owner about challenges—whether they’re in your industry or not. Everyone deals with workforce issues, cost pressures, and now AI implementation. Whether it’s wealth management, manufacturing, or insurance, the challenges are similar, though with nuances.
At an event—whether a chamber event, a CBIA event, or a Connecticut Wealth Management roundtable—you can have real conversations about best practices and learn from others’ experiences. That’s something unique about Connecticut. I ran businesses in other states when I was part of Leggett, and that close-knit, relationship-driven community isn’t as common elsewhere. Here, you can make instant connections in a 500-person room—ask someone where they live, where they went to school, what their spouse does—and suddenly you have one degree of separation. From there, meaningful business conversations flow naturally.
That’s why I emphasize spending time outside your four walls on a regular basis. It’s even more important than consuming social media content, which can be overwhelming and hard to navigate.
Kevin Leahy: Isn’t it fascinating how much people want to help? Chris, you and I are on an advisory board together—somewhat randomly asked to join—and nobody on that board probably has the time to actually be on it. Yet, we all continue to do it because it’s rewarding and fun. You feel like you’re really helping the company, the owners, and the executives.
Chris DiPentima: Absolutely. You’re right. I’ve often said that the time you spend internally and externally is critical because innovation doesn’t happen in isolation. You can’t just sit by yourself in your CEO chair, your sales chair, or whatever role you’re in—innovation requires collaboration.
Kevin Leahy: Denis, did you write that? Sorry—someone’s going to want to write that down. I don’t have a pen. You can’t have….
Chris DiPentima: …Innovation in isolation. Collaboration drives it. When you’re with people, like on an advisory board, everyone brings perspective. You bring perspective, I bring perspective, someone else brings perspective—and collectively, we collaborate. We talk through problems, and that leads to innovation and solutions.
Kevin is on our Foundation Advisory Board, Denis, you’re on the CBIA Board. Those boards collaboratively drive innovation: what should CBIA do from an advocacy perspective, from a products and services perspective, from an events perspective, from a research perspective?
That’s the importance of collaboration in Connecticut. The collaborative spirit here is as strong as I’ve seen in any place where I’ve been involved in or led businesses.
Advice for Entrepreneurs & Business Owners
Denis Horrigan: Well, you deserve a lot of credit for that too, Chris. The community you’ve created is exactly what we’re trying to do here with In Good Company: create a space where business owners can help each other. I used the phrase earlier about the loneliness of being a business owner. People are craving opportunities to collaborate, share ideas, and seek advice.
I think what you do is awesome. Is there something you think folks are missing? A critical issue that people aren’t paying attention to but should be? Maybe they haven’t had the chance to attend one of your events—or one of ours—but what’s one thing you’d want to share with them now?
Chris DiPentima: Well, I will say, in this rapidly changing environment—as I mentioned—the cycles are a lot shorter than they were pre-pandemic. One of the things I see, both internally at CBIA and in conversations with company leaders, is that not enough people realize what got you here today is not going to get you there tomorrow.
I used to say you’re underestimating how fast what made you successful is expiring. It expires—and nowadays, it expires very quickly. The expiration date is more like a milk carton than a can of soup. A decade ago, what got you here might have carried you a little further into tomorrow. But now, with technology, competition, and more people starting their own businesses, that window is much shorter.
It’s not that business owners are resting on their laurels. It’s more that they think, “We’ve got a really successful mission. We’ve got a successful product. We’ve got a successful team.” But sometimes there’s not a lot of depth to that team. They’re not investing enough in leadership depth.
To me, the biggest long-term risk isn’t market disruption—it’s leadership fragility. I’ve seen too many cases where a few senior leaders leave, and suddenly the CEO realizes there wasn’t much bench strength. Now they have to build a new leadership team, and it takes time for that team to gel. And meanwhile, what got you here today isn’t enough to get you there tomorrow.
So I often tell leaders: spend that extra dollar to create depth on your leadership team. It may be as important—if not more important—than the next piece of equipment, the next building, or the next product line you’re launching. Leadership fragility is a real risk.
Denis Horrigan: Well, you used the word invest, and that’s really what it is. You’re investing in your leadership team, in your management team—and that investment can have as big an impact as a new piece of machinery on the floor. Probably even more, especially when you’re trying to evolve with whatever the competitive landscape looks like.
Even when it comes to exit planning, you need a strong leadership team in place. Far too often, what we hear is, “It’s really expensive to hire a CFO these days.” My response is: it’s a lot more expensive not to hire a CFO these days.
So… all right. You’ve got another one, Kevin?
Kevin Leahy: Chris, it’s not lost on me that you—and by that I mean CBIA—serve as that external perspective for so many business owners. Sorry for the plug, but you deserve it, and your team deserves it.
For a lot of us—and we’ve been there, maybe sometimes we still are and just don’t realize it—you don’t always know where to turn. You’re so busy. You’re hunkered down. You think you’re doing all the right things. The “right thing” feels like spending 15 hours in your office with the door closed, head down, working hard.
But it’s been organizations like CBIA that have helped us—literally, and I mean that sincerely—get out there more. To recognize issues we might not have otherwise seen. To make connections we wouldn’t have made. It’s one of those things that’s hard to understand until you experience it. And then you start to feel part of a community. You realize you’re not in it alone.
Whether you’re in financial services like we are, a professional services firm, or a manufacturing company—which on the surface look very different—at the core, they’re not that different at all. We all need strong leaders. We all need to make good decisions. We need to be thoughtful, care deeply about our teams, and think beyond just today—or even just Friday.
So, truly, we appreciate the effort you’re making and the effort CBIA is making. You know I joke with you about running for governor—and yes, it’s partly a joke—but it’s also because you’re a great leader. A lot of people in this state know that. A lot of people don’t yet. And if they don’t, they should take a closer look at what CBIA is doing. You’re doing good things.
Denis Horrigan: Chris, I’ve got to say, I love the recent videos you’ve been doing. They’ve been fantastic. You’re clearly a natural on camera—who knew you were such a ham? You really do them well.
All right, I’m going to try to wrap us up here.
If you could leave the business owners who are listening or watching this with one piece of advice—something you learned the hard way, maybe something you got wrong along the way that others could learn from—what would that one thing be?
Chris DiPentima: Oh, that’s a great question. There are so many pieces of advice we could all pass along to each other, right?
Okay, yeah—don’t let your staff do holiday videos that make you follow whatever’s in the script.
But seriously, if I had to sum it up in one piece of advice—if I could go back 25 years and tell my younger self something—it would be this:
Build a business that doesn’t depend on you.
I missed too many family events. I stressed over too many decisions. Denis, you mentioned the loneliness at the top—and that’s real. Too often, I confused involvement with impact. I felt responsible for every single decision.
There’s a line I once read: if you’re the smartest or busiest person in the room every day, even if the results look good, the system is broken.
You may think you own the business—but if you have to be involved in everything, the business owns you.
Trusting others and building a strong team—that’s at the heart of building something that doesn’t depend entirely on you. I think we eventually got there at Pegasus. I know we’re there at CBIA—and that’s a big reason I’m enjoying this chapter so much.
When we rolled out the Entrepreneurial Operating System (EOS)—and I know you guys use it too—I remember someone saying, “You might not be the integrator.” Years ago, I might have resisted that. I might have thought, “Am I taking my hands off the wheel?”
This time, I didn’t hesitate. I said, “Great—run with it.”
I’m in a different place now. I don’t need to be involved in every decision. I joke that I just go where the team tells me to go, wear what they tell me to wear, and say what they tell me to say. There’s some sarcasm there—but there’s also some truth.
CBIA isn’t about me. It’s about the members. It’s about the staff driving the mission because they care deeply about the business community. And if the business community is doing well, the residents of the state do well.
Building a business that doesn’t depend on you—that’s the goal. It took me too long to fully embrace that at Pegasus, but we got there.
The earlier you do it, the happier you’ll be—and the more successful your business will be.
Kevin Leahy: And it’s pretty telling that you’re saying that, because you wouldn’t go where they tell you to go, wear what they tell you to wear, and say what they suggest if you didn’t genuinely trust the people around you.
That only happens when you’ve built real confidence in your team.
In other words, you’ve done exactly what you’re talking about—you’ve built something that doesn’t depend entirely on you.
Concluding Thoughts
Denis Horrigan: You’ve clearly built a team you can rely on. So again, kudos to you.
Trust others. Get out of their way. Build the business so it doesn’t depend on you.
That’s powerful advice—and not always easy to live out.
Chris DiPentima: No doubt about it. You’re right—it’s easier to lead that way when you have a great team around you. It’s easier when you have great customers—in our case, our members. We have a fantastic board, policy councils, and strong representation across different member segments. That collaborative spirit, those relationships—they truly make a difference, both personally and professionally.
I often say I’ve got the greatest job in the world. And it’s not just the job itself—it’s the people and the mission. Somehow, this path—from trial attorney to manufacturer to leader within a publicly traded company—brought me here. And when I look back, there are some interesting similarities between what I’m doing today and what we were doing at Pegasus.
I just feel incredibly fortunate. Fortunate to be in this role, and fortunate to have people like you involved along the way.
Denis Horrigan: Awesome. No, we truly appreciate you—your leadership and your friendship. What CBIA is doing is exceptional.
And if you’re watching this and you’re not involved with CBIA, you’re missing out. The passion of the staff is incredible. The passion of the members, the genuine desire to build a strong business community—it’s phenomenal.
Being involved with CBIA has honestly been one of the most meaningful parts of my professional experience. So, thank you, Chris.
Denis Horrigan: Alright, we’re going to wrap things up. I want to let everyone know that our next in-person In Good Company event is scheduled for March 19th—that gives you, Kevin, a couple days to recover from your St. Patrick’s Day festivities!
We’ll be hosting it here in our office, and the focus will be AI—how it relates to manufacturing, service organizations, and other industries, and how businesses can start to tackle this rapidly evolving topic. It’s something everyone’s thinking about and beginning to invest in, so it should be a great discussion.
Chris, thank you so much—really appreciate you joining us. Great to see you, as always, Kevin. Good to see you too!