Some of the most important breakout moments happen when a business has to move beyond the person who built it.
In this special compilation episode, Christina May revisits conversations with Tony Checchia, Spencer Teel, Nicole Elia, Aaron Shapiro, and Nick Molfino about succession, leadership, and what it takes to build a business that can continue without its founder.
They share stories of creating a company with its own identity, giving people room to take ownership, developing a clear vision, handing off responsibilities, and preparing for unexpected changes in leadership. From gradually transferring responsibility to planning for the possibility that a founder may suddenly be unavailable, these conversations reveal a common lesson: building a lasting business means making sure the people, knowledge, and leadership needed to move it forward do not depend on one person.
Tony Checchia: And it's me. It's all Tony C, but it's not Tony C. I didn't want it to just be Tony C, or I would have named it after myself.
Aaron Shapiro: He passed away completely unexpectedly, and it forced us into that "what if" situation for real.
Nick Molfino: But then all of a sudden, it hit me. I was like, "What if I died?"
Welcome back to The Breakout Moment.
At some point, every business owner has to ask: Could this company keep moving without me?
Throughout the podcast, we’ve heard that question come up in different ways. From building a company that isn’t tied entirely to the founder, to handing over responsibility, to planning for the day someone else has to take the lead.
This episode is about building something that can last beyond you.
And Tony Checchia gets right to the heart of it.
Christina May: I want to go back to something that you said that really resonated with me. When you started the company, you didn't want it to be Tony C, and I really resonate with that because when I started the company, I did not want it to be Christina May. And even though we both are very much the character-out-front personalities of our firms, everybody knows that, right?
But at heart, I wanted it to not just be me. I wanted it to have longevity, legs beyond me, and impact beyond me. And I was very intentional about that decision.
Tony Checchia: Yeah, I struggled with that, Christina, because even to this day, with not a large company, there are five of us at VCRE.
But, you know, I want my associates to have their own identity, their own workflow. We do work as a team, and we also individually work on assignments, whether it's working with buyers or sellers or whatever. But having grown up in Frederick and only been in real estate in Frederick, and having been branded Tony C since 1992...
I think it's a thing, right? It's what I'm known for and who I am.
CM: It's your name and it's your brand.
TC: It's my personal brand. I'm not trying to hide from that. But I also recognized, at least I thought, that if I'm going to start a company and I want to invite other associates, realtors, other people to get on the bus to be part of this company...
TC: It just felt selfish. It felt selfish. It felt like I was trying to find, and I think I have found, that balance between obviously not putting on the shelf who I am, because it's important, because a lot of referrals and business come through the door because...
CM: People do business with people.
TC: Exactly. But I also want it to be important that Justin, Amos, Maria, that they have their own book of business and that they're able to grow, and I'm supporting them, and they have their own autonomy from the Tony C of the company. But at the end of the day, the buck stops with me. I'm the broker.
And, you know, it's my company. I stand 100% behind it. But that was tough. That was tough to navigate through.
Building beyond the founder starts with making sure the company is more than one person’s name, relationships, or reputation.
But that also means giving other people something clear to carry forward. For Spencer Teel, that meant turning his vision for the company into something the entire team could understand and act on.
CM: I think something that I wanted to pick up on that you said too is the vision kind of brought everybody together. Reflecting back on when you were first bringing this into the team, getting buy-in from the team, what were some of the first signs that you saw? I think, like you talk about Teel University, that's a three-year process. But what were some of the... I think sometimes we get a little lost in the sauce, so to speak, and you need, to your point, a sign like, "Keep going. I'm doing this." What were some of the early signs that you saw, like, yeah, I'm on the right path?
Spencer Teel: The initial immediate reaction of excitement was energizing and reinforcing to me that this was a good thing that we did. But I think more so, the cohesion and team dynamic and sort of rowing in the same direction as an organization. Everyone now had that clear view of where the company was going. So, a lot more alignment.
CM: So tactically, how do you fold that in? Like employee reviews, or what are some of the tactical ways that you make sure that you guys stay in alignment with the vision in the day-to-day?
ST: That's a really good question.
Just by practicing what we preach. Yeah.People are recruited and evaluated based off of their alignment with our core principles. And I think those have always been a guiding source for the company, again, which really drive and fill up to the Built to Serve purpose. So I don't think I answered your question.
CM: No, no, no. I think that's a great answer. I think that's, you know, when we're hiring somebody or even with clients...
Customers, if you're not in alignment in how you do business, how you treat others, it's not going to work well, right? So your vision and your core values as a company, and you're hiring somebody, you want to make sure that their values are in alignment with yours.
And if they're not, it's not going to be a good fit for either one of you. So I think that that's actually a really good takeaway for anybody: don't just hire for the skill set or the personality, right? We all have heard of personality hires, but hire for your values, your culture fit.
We call it culture, but it's really about value.
ST: Yeah, for sure. So part of our offer letters have a contingency that they are aligned, meaning that they've read the vision and are on board with where the company is going.
CM: So that's a great takeaway right there.
Eventually, someone else has to start taking on the responsibility.
Nicole Elia’s story shows that succession isn’t always one big handoff. Sometimes it happens one role, one decision, and one hat at a time.
CM: So now fast forward. Mom is also part of the business?
Nicole Elia: Yes.
CM: Office manager?
NE: Yes.
CM: Okay. And then, you know, Dad. At what point did they come to you and say, "Hey, we've got other plans"?
NE: I guess about ten years ago.
CM: Okay.
NE: It was a conversation. They're like, "What do you want to do? Do you want to stay here or do you want to take over?" And that was the conversation, more or less. So when we had that conversation, then it was like, okay, yes, this is what I'm going to do.
I know I could support my family this way. I have invested interests with our manufacturers. I have invested interests with my customers.
CM: You understand the business from the ground up. That's big.
NE: Yes, exactly. And, you know, my dad built something pretty awesome, in my opinion. You know, it's a little biased, but it was just him and my mom initially.
And then now we have just shy of a dozen folks and a fairly substantial line card. So, I mean, what my dad built was great.
CM: Yeah. So they had that conversation with you, then you were like, yep, this is my path forward. What did that process kind of look like for you guys?
NE: It was pretty simple in that regard.
It was more like a lot of our manufacturers wanted to know, does my dad have a plan? And he did. Did we have something on paper? No. So it was more like whenever he feels he's done, he'll be done. And I mean, my dad still works today, and so does my mom.
CM: Okay. Part time?
NE: No.
CM: Nope. They're all still there every day. You're like, they're still there every day.
NE: They're all still there every day. I mean, they'll take more time here and there, but yeah, no, they're still very active. You know, my dad picks what he wants to do now as opposed to doing everything. I do everything for him now.
But taking over all of the founder’s responsibilities can create a new problem.
If everything now depends on the next leader, the business is still dependent on one person. Nicole had to start figuring out what she could hand off, too.
CM: Of all of the hats, talk to me about what the process has been for you to kind of, you and I talked about this a little bit before we started, peel a hat off and hand it over.
How do you know which ones first off?
NE: Last year was a challenging year. It was a great year, but for me, mentally and physically, it was challenging. In 2025, just for perspective, I call my car my office. That used to be me until recently. I think I put about 29,000 miles on my vehicle last year.
So there's a lot of driving, a lot of windshield time. So in December, I was like, what can I get rid of? What do I need to do versus what do I want to do? And then what am I comfortable giving to someone else? And our conversations with my mother and father were like, "Well, your father did all of that before."
And I'm like, "Yeah, but you did his clerical while he was doing that. I don't have you." So it became extremely clear I needed an admin. And I think last year I was like, I'm going to hire an admin. This is what I think is going to be what we need.
And, you know, I wrote a posting, had my mother review it, had my dad review it. "Do you really need a person? Can we just bring someone part time?" And I'm like, "I don't know. I don't really feel like a part-time..." And I was at a conference in December and I was like, January, putting the posting out.
I don't have time in December to look through resumes.
CM: No, no, it's the holidays.
NE: Yeah. So I was like, January. So I posted it the first week in January. I had my admin at the end of January. I pulled the trigger really quickly, and fortunately she was available to start.
CM: How has your life changed since then?
NE: I'm still onboarding her 100% on what I need.
CM: And yourself.
NE: And myself, because I am a control freak.
CM: That's okay. You don't have to whisper it. It's safe. I am a control freak too. I have trouble asking for help.
NE: So, like, some days I'm coaching myself on my drive into work, and I'm like, okay, today I will bring Amber and we'll talk.
And I'm just going to have her sit next to me, and I'm just going to say, "Send this. Send this." So that's what I've been doing. I have to coach myself into releasing tasks. There have been some things. We implemented a new banking system. I had her learn it with me. Normally it would have just been me, right?
I had her learn it with me, and she has been awesome at the integration of it. It's a very effective banking system and fraud protection.
CM: Yeah, that's huge.
NE: All of the money coming in, none of it going out. That's the way we like it. But she's helped me manage to make sure we make payroll.
Nicole and her family had time to work through that transition. Aaron Shapiro’s family didn’t.
When a leadership change happened unexpectedly at Shapiro & Duncan, they learned quickly what was already strong and what they hadn’t prepared for. That experience changed how they approached the next transition.
Aaron Shapiro: But as far as succession, the saying of, "What would happen if I got hit by a bus?" Like, how do you prepare for that? He passed away completely unexpectedly, and it forced us into that "what if" situation for real.
CM: For real. Yeah, yeah.
AS: So I would say a huge testament to him and his leadership is he did such a good job of delegating and hiring the right people that we are still in business, and we didn't miss a beat because of the way he led. He maybe didn't prepare the people under him for that to happen, but he let them be able to take the next step when that happened.
CM: Right. And, you know, talk a little bit. A lot of us, our families are part of the business, formally or informally. I always tell people if you have a spouse or partner and one of them's a business owner, God help you if the other one's not. They better be really understanding. But those are our support networks.
In your case, you have other family members that are part of the business as well, right, that were going through this with you?
AS: Absolutely. So my dad was his brother and co-owner. We went through it together. Both my sisters are in it. Another uncle. So definitely a family business. Very family business. I mean, there's also a lot of employees that have been with the company longer than I've been alive.
So I have a lot of uncles and aunts that are also in the family.
CM: I love the chosen family aspect. Even in personal life, being a chosen aunt is very cool, right?
AS: So we say we treat people better than family because if you get in a room with all of us and we're very honest and direct with each other, we don't want to treat our employees sometimes that way.
CM: Yeah, no. Better than family. Yeah, yeah. I agree with that. I agree with that. So they were going through this process with you. Obviously, this wasn't pre-planned. Now kind of sitting here, hindsight being 20/20, right, you can look back and see what should have been done.
AS: Yeah. Right, exactly. It's given us an opportunity to now, like my uncle is currently CEO and stepping away in a year, to do this the right way and start.
You know, we took two employees, hired them as co-CEOs, and now we have a year to work underneath him and understand and start handing off those responsibilities, which I'm very grateful for, to be able to have that time and learn from...
CM: Yeah. Learn from what didn't go right the first time.
AS: Right. Learn from what didn't go right the first time.
CM: What were some of the things that didn't go right the first time?
AS: I don't know. I wouldn't say didn't go right, but just preparing things. Like communicating. When Sheldon passed away, there were some employees that weren't sure if the company was going to be around. So it's like, let's communicate and kind of have that reassurance to everyone that the company is still alive and well and thriving. And then other things like bank accounts and the urgent, necessary things that just have to be done.
You don't even think about things like signing paychecks on the bank account. And when you have time to plan it, it's very easy to do. When you don't, everything's a panic and becomes very stressful.
CM: So now that you guys have the gift of time, talk to me about what's happened since.
So this kind of was a catalyst that pushed you guys to deal with succession planning kind of by fire. But let's talk about some of the results. What were some of the outcomes?
AS: So our current CEO, Charlie, my uncle, now put a date on when he's planning on retiring. He's still going to be more of a mentor.
And then he's actually chosen two individuals that he's going to be selling his shares to. So that's the first non-family members, which is very exciting. For me, it brought a new energy to the company, a new perspective.
CM: So employee-owned. You guys are moving to employee-owned.
AS: I guess somewhat. Yeah. I think it was select individuals that have deserved it and worked their way up in the company.
And yeah, so it's been a very great experience. And like I said, new energy. My dad and uncle maybe are not as motivated for change. You know, they've kind of seen it. They're not inspired. You go to these two people with a good idea, they're like, "Let's get moving. How can we put a team together to make this happen?"
CM: That's amazing.
And then there’s the question most owners would rather not think about at all.
For Nick Molfino, becoming the sole owner forced him to think beyond who would run the company. He had to consider what would happen to his employees, customers, subcontractors, and family if he suddenly wasn’t there.
Nick Molfino: I was working on my private pilot's license.
So basically I was doing my last long-distance solo, made a bad call on weather, and I'm now in the Shenandoah Valley. I'm at about 2,800 feet off the ground, and I'm not moving. The headwind is so strong that my speed indicator on the plane is 130 miles an hour, my ground speed is two miles an hour, and I'm getting tossed four or five feet in either direction, up and down, sweating bullets. Fight my way back to Leesburg.
Had like four or five landing attempts, almost hit a drone. It was one of those where, like...
CM: I'm laughing only because I can relate in some ways.
NM: Couldn't get me out of the plane fast enough. And as I'm driving home and I'm kind of getting my wits about me, I'm just thinking, like, I made so many mistakes. I should have never gone on that flight.
I was rushing it. Once I knew the weather was coming, I should have stayed down in Shenandoah. But then all of a sudden, it hit me. I was like, "What if I died?" I have life insurance, right? I mean, my wife would have gotten a little bit of money. Obviously, the other part of that, the aftermath, would have been awful for them.
But then I'm like, we personally guarantee the line. We personally guarantee the surety, right? And I've got 26 employees who count on me.
CM: And their families.
NM: Right. And their families and our subcontractors, thousands. So I'm going, I would have died and left my wife in a position that she's completely unprepared for.
CM: Right.
NM: And I left my team in a position that they're completely unprepared for.
And so through Vistage, again, through the introduction from Kathy, I met Wayne Zell, who's probably hands down one of the best attorneys for ownership transition planning and all of that stuff. And he came up with a really cost-effective vehicle that basically set me up where we have an LLC that owns life insurance on me. That policy is a one-way buy-sell.
It will take my ownership and pay my wife for it. And then I've got a separate policy that will infuse some operating capital into the company. And John Ellard, my general super, who's again my right hand, couldn't do this without him, he becomes owner of the company, and he's got two options. Close it, right? Get everybody a good separation severance package, because there's a couple million that drops in on top of...
CM: We're fully capitalized, right?
NM: So you have ample money to say, okay, we're not taking on any more work. Slowly phase the jobs.
CM: Phase it.
NM: Close them correctly. Pay all the subcontractors. Give the customer what they needed, and give folks three, six months severance, whatever they need to make sure that basically, if I die, I want it to be the happiest day in everyone's life, right?
That sounds really silly to say that.
CM: No, but it is.
NM: But as an owner and that responsibility, I will have met my responsibility to my family and my employees.
CM: That comes back to your core values.
NM: It does. And the other option is keep it.
CM: Yeah.
NM: Keep going. Right. And so my family's taken care of. My employees are taken care of. And that was one that, you know, when we were going through the transition and everything else...
I never thought about it because I always had a partner. I always had, if something had happened to me, insurance would have kicked in and somebody would have picked up the pieces on the business side, right? My wife and kids would have still dealt with whatever they had to deal with, but the business was okay. And then all of a sudden it was like, well, the business is not okay.
But then it was, well, it's not just the business, right? Because my wife's name is tied to everything, and if I die and leave my employees unemployed, my subs not paid, my clients not serviced, and my family in bankruptcy...
CM: That's not the legacy you want to leave.
These stories all come back to the same idea: building a business beyond yourself takes more than naming a successor.
It means sharing the vision, developing other leaders, letting go of responsibility, and making a plan before you need one.
Because legacy isn’t just what you built. It’s whether what you built can keep going without you.