Unplug, Recharge, Reset: Lessons on Growth with Tony Checchia

What happens when the challenges you face at work start looking a lot like the challenges you face everywhere else?

In this episode of The Breakout Moment, Christina May sits down with Tony "C" Checchia, founder and broker at VCRE, for a conversation about self-awareness, expectations, emotional resilience, and the lessons that seem to follow us through different seasons of life. Together, they explore mentorship, personal responsibility, and why growth isn't something we achieve once but something we continue to work on over time.

Christina May: Well, Tony, I am so excited to have you here. We have known each other for years now, and we've done business together. It's been a wild ride. Welcome to The Breakout Moment.

Tony Checchia: Thank you, Christina, and thank you for the invitation. I'm super excited about what you're doing, and happy to be a part of it, and happy to be here today. How long have we known each other? Longer than we each admitted. Congratulations on this Breakout Moment podcast. This is fun.

CM: Yeah. Well, at the end of the day, while we're in business, right? We wanted to have some fun. I think every entrepreneur feels that way at some point. I want to have fun.

TC: Do shit you love or don't do it at all.

CM: Right. Bingo. I tell everyone the day I wake up, and it hasn't happened yet in 13 years. But the day that I wake up and I don't want to go to work, I'm done. Something's gotta change. But I don't think I've ever. I've had hard days. I've had days be like, oh, I gotta deal with this. But I've never had a day where I felt, no, I don't want to do this anymore.

TC: I can agree with that. Also, there are times when the work becomes work, and it's challenging. But, I mean, I just feel blessed that I've found something by accident. That was not my game plan. Coming out of college, I was going to go to law school. I don't know if you know this story or not. I think I've told you the story. And then I got my real estate license as a backup plan. Sister, Doctor Mary Nussbaum, my economics professor slash advisor, says to me, don't be so hard on yourself. You can go to law school. Maybe someday this real estate thing might work. You might be the owner of your company someday. I'm like, prophetic, right?

CM: There it is.

TC: Yeah, and here I am, you know, almost 40 years later and still doing it. I love it.

CM: I do too. I absolutely love it. I think it's interesting. I don't know about you, but for you, that was the backup plan. For me, I was just in denial for too long. I kept having friction in my jobs because I wanted to go off script. I wanted to go do this, or I want to go chase that. I mean, everyone at Illumin8 knows, I always tell people, I like to run into burning buildings, and in corporate, they don't like you to run into burning buildings usually, unless you're a firefighter. Obviously, I wouldn't make the cut. I was just in denial for so long. Then I finally, just out of necessity after being told no so many times, no, you can't have that, and I was like, screw you.

TC: Mine was about two years of denial. Coming out of college, my parents had invested in me to get a college degree and aspirations to go to law school, and I got a real estate license as a backup plan just so I'd have something to do after graduating. Started working in real estate, but felt that I had settled. I was like, why did I go to college just to be a realtor? This was such a waste-kind-of-attitude, a really arrogant, young, and arrogant, and thought way more of myself than I probably should have at that time. I had a transaction that involved working with a local real estate attorney and experienced firsthand what that attorney brought to it. The friction, the tension, and his whole disposition were very one-sided. He was representing the buyer, and he was advocating only for the buyer. As brokers, we're bringing parties together, we're solving problems, we're resolving issues, and we're making the transaction come together. He just kept fighting me the whole time. I had that moment where I was like, "That's not my DNA." What the hell was I thinking, going to law school like that? If that's what lawyers do, that's the last thing on earth I want to do, so it took a while. Then I had the fortunate opportunity of a seasoned broker agent who had been in the business for a while, got in a car accident, was recovering from his injury, invited me to work on a group of investment properties that he was listing as a portfolio at one time, and he was like, " Do you want to help out?” Yeah, sure. What do you want me to wash your car, you know, change your oil? What do you want? He's like, no, no, work with me on these listings. And so my experience level and my interaction with higher-level transactions just jumped, and I was able to work with somebody who, as a mentor, mentored me, who gave me that kickstart and accelerated my on-ramp to really get into real estate. That's when I really started to say, "Hey, I'm actually really good at this, and I love what I'm doing, and wow, now I’m getting paid.” I get to the settlement, everybody's happy, and I get paid. I'm like, when, when, when, when? So, things kind of really started to fall in line until I got bored, and needed to move on, and felt like real estate. Early years for me were transactional, and in a residential environment, everything is transaction-based, and it's how many transactions can you do? It's a lot of rinse, repeat. It's volume. It wasn't challenging myself. I wasn't growing, I wasn't learning. So I made a move and was able to move into a situation where I wanted to principal up. I wanted to become an owner and have something that I could build that I owned. I had the opportunity to partner with another, a very experienced broker who was more towards the twilight years. He was closing in on retirement, and I thought this would be a good fit. I could go in and learn from him, and we would complement each other. We had a good run. We worked together as partners for almost 18 years.

CM: That's a really good run.

TC: But it wasn't my company, right? So my ideas were always met with, well, that's not, you know, even simple things like the company name was very defined. I always felt that it really limited the audience of the work that we were doing, which was general brokerage, not just land, and the company name was land. I was like, but we're not just a land company; we're doing leasing, we're doing commercial transactions, we're working on investment properties. And so, that was kind of phase two of my career path, if you will. Then, the next “aha” moment for me was the transition from Frederickland Company to Veritas commercial real estate, which quickly became an acronym because nobody can pronounce verità. So VCRE, keep it simple, baby, was born. We just celebrated our ten-year anniversary in February. And it's me. It's, it's, it's all Tony C., but it's not Tony. You see, that was the other part of what I wanted to do. Forming the crew was- I didn't want it to just be Tony C, or I would have named it after myself. So, I deliberately named it Veritas Commercial Real Estate. Verità means the truth in Italian. I deliberately chose that word because I had another experience with some other folks that would know the truth of it, bit them in their ass. So I was like, I'm just going to make that constant reminder. I also brought in some of the other meanings behind the name. So, I've been in Rotary for almost 30 years. Rotary is a big part of my life. The Rotary Four-Way Test is the truth. So, the truth, true. verità, all of that came into that. Honestly, the other part of it was, it's hard as hell to find a name for a company, holy shit. I’m trying to figure out an original name or even verità is not original. There are other companies that have that name. Finding the name, figuring out the URL, figuring out all of that.

CM: Yeah, illuminate? The spelling, there's a reason. It’s because the others were not available.

TC: Right.

CM: You know, I know I wanted the eight because it was an infinity symbol. I feel that the same thing, the customer journey, is a cycle that feeds itself. I was very intentional about that. The spelling came down to domain issues. Sometimes the inspiration isn't as creative as people think it is. It's more like a necessity. I have to have something unique.

TC: Yeah, that was crazy. I remember, I reached out to one of my sisters, and I asked her for advice, and she was actually- she was the one who initially was like, well, what about verità? I'm like, hm, maybe that could work. Then, I figured out the rest of it and went through different iterations of if we're going to be advisors, if we're going to be a brokerage. Ultimately, at the end of the day today, it's just VCRE.

CM: But I love that it has, I mean, it's good and bad. If I put on my marketing hat for two seconds, having what you do in the name makes it very easy for people to understand what you do, shortens the education cycle, but it also limits you as well. So if I kept it as originally when we started out, we were Illuminate Marketing and Public Relations. We don't do public relations anymore. I've taken away the marketing as well because we do other things, we've become much more technical, and it allows the company to change and meet the needs of our customers as it needs to, with adjacent opportunities. Same thing for VCRE. 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. Even though we both are very much the character outfront, personalities of our firms, everybody knows that. But at heart, I wanted it to not just be me. I wanted it to have longevity, legs beyond me, and impact beyond me. I was very intentional about that decision.

TC: Yeah, I struggle with that, Christina, because even to this day, with not a large company, we have five of us at VCRE. But I want my associates to have their own identity, their own workflow. We do work as a team, and we also work individually on assignments. You know, whether it's working with buyers or sellers or whatever. 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. 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, others to be part of this company, it just 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.

CM: People do business with people.

TC: Exactly. But I also want it to be important that Justin Amos, Maria, 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 it's my company. I stand 100% behind it, but that was tough. That was tough to navigate through. I never even considered from a naming aspect, whether it was Tony C or, God forbid, Chicky Realestate. Could you imagine?

CM: Nope.

TC: That was not even an option. Then I also wanted to and even if I struggled with commercial so Verità Commercial Real Estate is primarily what we focus on. However, we're a small boutique firm in Frederick, and we deal with mixed-use properties and historic properties, farms, and land, and not everything is commercial. We do have estates and residential properties that we broker. I've actually had rentals, and I've had property management, and I've had people say, well, you're a commercial company, why would you be listing that? So there's still some of that that I, you know, struggle with since we've gone completely to the acronym VCRE, that has not been as much of a factor. 80 to 90 percent of our workflow is focused on more of the commercial real estate than residential or something that would otherwise not fit under that umbrella because, as you said earlier, the name does have a meaning. When I was at Frederick Land Company, Frederick Land Company listed a space for lease that was in a shopping center. I was like, why is a land company doing leasing? That felt like a misfit to me. My partner didn't feel that way. He always just said, hey, it's just a name. It's no different than Klein Real Estate or ABC Real Estate. And I'm like, yeah, but it is because land is in there. At least in my mind, that's the way it felt, and it was defining the company. That's one of the things about having a partner and now it's just me. I agree with myself over these things, but I don't have a partner to argue with over this.

CM: That’s like a double-edged sword. I don't have a partner either. There are days where you're like, gosh, I wish I had somebody bounce this off. I especially think too, as you grow through the years, you mentioned mentors were a big part of your journey, then you become the mentor later. For me, I think as you grow through the years, you mentioned mentors were a big part of your journey. Then you become the mentor later, right? Yet we still need people to bounce things off of. You need a mentor in a different way.

TC: Well, and I mean, I mentioned this to you before we started the show. My parents have always said that I'm too good for my own good. I'm too nice, and I know it. As an owner, as the boss. I could use a partner. Someone that could balance my disposition and someone that could bring let's say a harder edge, but a more defining role to some of the decisions that need to be made. I tend to be the one who just goes along to get along, and I'll just make it work. I'll compromise to get to the next step. The outcome is more important than how we get there. That's something I'm personally working on still. Something that I know is a weakness of mine and something that I know I need to improve on if I want to truly be a business owner and have something that I can pass on that is beyond me. I have to get to that place, and I'm getting there, I'm getting there. I have a great team right now, and I think I finally have, as my sisters always advise me, the A-Team. And I think I am there with my associates and with my team. Now it's a matter of defining and stepping back and saying, that's not my it's hard. You know,

CM: It's hard. Yeah, I can you know, I think one of our greatest strengths is empathy. I struggle with the same problem or not problem, challenge that you do, reframe that. In that I feel sometimes I let almost, I don’t want to say too patient, but you let things go, I don't want to say too empathetic, but my empathy, it cuts me both ways. I can be incredibly direct and incredibly empathetic. Both. And finding the right combination of switches is really difficult for me. I struggle with that. I want to always believe in the people that I work with, that I work for, and then to have that, it's a trust. It's a hard trust because it's like having kids. Your business is this thing that you love that's outside of you. It's running outside of you that you don't have control of some days.

TC: It's a life balance challenge. Christina, with family, with business. My family says I don't make enough time with my family and I'm not patient with the family because I use too much of that up, and that energy is consumed with the business. And of course, I stress because I'm like, well, I have to provide for the family. So I'm going to focus on this first. And, you know, and they're not wrong. And that's something I'm working on personally working on trying to be more deliberate about scheduling time with my family. You know, God forbid I shut my phone off at 7:00 at night and I got the shakes.

CM: You are always available.

TC: It’s something that is just, if I'm in the bathroom or I'm asleep, I'm not gonna answer my phone, all right?

CM: Okay good, so I know you're not texting me from the bathroom.

TC: I'm not doing that. I've been on the other end of that call where you hear the flush and you're like what? It just happened last week. I’m just like oh come on, seriously? So, yeah. So I'm in the bathroom, I’m sleeping, and I tell people I'm not answering my phone. Beyond that, I do pride myself in being accessible and available.

CM: And that's part of your business too.

TC: I know, but it also it leads to abuse and an expectation is set. And then it's like, if I go away, I can. I'm never unplugging, I'm never away. And I know I need to do that. I know I need to unplug, recharge and reset and be away.

We just took a trip recently. My wife and I celebrate our 20th anniversary. We went on a cruise and there were periods of that trip, where we didn't have cell service and she was like-

CM: How do you cope with that?

TC: Well, she was laughing. She's like, "oh my God, you're going to have a nervous breakdown." I actually was like, you don't have cell service, we’re in this castle. And I'm like, "oh, I'm good, I'm just going to go outside and get some air." Right. But, no, it was refreshing. It was like, all right, this is just God's way of saying, hey.

CM: You've got to unplug.

TC: Unplug. Take a minute.

CM: Yeah.

TC: Take ten.

CM: It's interesting too, sometimes the timing.

TC: It's hard though.

CM: Oh it's impossible. I am never not thinking about it. That's just the way it's going to be. I've gotten better over the years about not being available all the time. I may be working, but you won't know it. I'm classic for scheduling emails. Everyone knows, if you get an 8:00 am email for me, I wrote that last night. I schedule them out. I'm really good about not pinging staff or anyone after hours because I want them to have that separation and that boundary. The rule is if I'm reaching out to you after hours, it's an emergency. I've gotten better about that over time, but I'm never not thinking about it. I think to your point that working on yourself, it's a constant. It is a constant series of moments and things with you, you go through cycles with your team, you go through cycles with the business. It's tough and I have noticed, I don't know if you've noticed this, but I have noticed the challenges in my personal life will mirror my professional life and vice versa. I will be fighting this, the battle on both fronts. That's when I know it's, oh, this is me thing. This is definitely a me thing.

TC: Yeah, there's a lot of that. Everyone's gonna be able to see this, right? So even my 16 year old daughter might be able to see this?

CM: Yes, your sixteen year old daughter can see this on YouTube.

TC: She and I are going through finding that balance. It's tough. I want to be available to her, my son, my wife, and my whole family. Finding that balance, being available, being present, not being on my phone,having a conversation and then text comes in and I get distracted and I'm like, but I need to be paying attention here. I know those things, but it's something to work on.

CM: It is something to work on. Everything in business is something to work on. If you were to give your daughter advice at 16 or something like that, when she finds herself in a place like that, what advice would you give her?

TC: That's a great question. It's tough because I think about my kids and what they're dealing with that we didn't have to at their age in terms of the instant everything.

CM: It's insane.

TC: It is. It's so different and it's so difficult to understand the pressures that they're under in the world that they're living in, in society today. My advice to them is that, this is noise that you need to understand and recognize that this is all just noise. At the end of the day, no one controls your emotions other than yourself, no matter what anybody says. I am so blessed that I learned this in the fifth grade. I learned at a really young age, who controlled my emotions and how I reacted to what people threw at me. I was the Catholic school uniformed kid that rode a public high school bus to school. So, you can imagine the environment that I was in with the goody two shoes, Saint John's grade school Catholic boy on a public high school bus and that was thrown into that fire. It was coming at me through a fire hose. I learned and that's something I hope my kids can learn from me and be able to control and not be overwhelmed by what society's thrown at them. Everything from all the social channels and all the instant to everything. It's just like, at the end of the day, number one, it’s like okay, what was the issue?

CM: It’s got the life of a fruit fly.

TC: Yes. It's gone.

CM: It's gone.

TC: Where was it? It was a crisis and it was just gone. So there's that aspect of it. Nothing's really penetrating, it's just surface. But it's also, it's a lot, it's a lot that the kids are having to deal with. Then the other part of it is just, trying to understand how to relate in a way like relationships are just so difficult at their age with other kids because everyone's got their head in the phone and everyone's communicating through phones.

CM: They're not communicating authentically with each other. I would not want to be that age again in this time period. I have so much empathy for everyone in those situations. It's just we did not deal. We dealt with our version but we didn't deal with it empowered by tech to the max.

TC: Right.

CM: Now adding an AI into it, It's a whole new fun thing.

TC: Holy mackerel. Even as adults trying to figure out what's real, what's not. Then I have at the other end of the spectrum, my mom, who's getting bombarded with AI stuff on her laptop as she calls it, the iPad. And I'm like, mom, it's not real. And she's like, but it is real. I got this and I'm like, no, that's fake. It's not real. Well, look at it and show them, I'm like, it's fake but how does she know? How is she going to know? I worry about that too. It is crazy.

CM: We're not keeping up with it at all.

TC: Yeah. The lack of filtering or control or management of that.

CM: Disclosure. The amount of disclosure I could care less of. I mean, I care, but I could care less about the content if it was just disclosed. That is something as a company, we've taken a stance on. You know, people ask us, well, of course we adopt tech.

TC: I'm setting up part two of our podcast.

CM: Of our podcast?

TC: AI and the whole data center conversation, because I think AI is more of the concern than the actual data center facilities themselves, and debate over data center facilities. I think the core of that is really the anxiety and the stress, true, real that people feel over AI and where we're going.

CM: It’s a lot of unknown, and it feels very threatening and when you feel threatened, what do you do right? We act out, you come from a place of fear. You're not coming from a place of curiosity.

TC: I don't know if you noticed, I just invited myself back for part two. Did you see?

CM: Yeah I did, we’re gonna definitely do that.

TC: So there's part two of this?

CM: We can do two, I’d love that. I could talk about that for hours. For me, I think that going back to relationships and authenticity and tying that and teasing part two, I think in the end, regardless of the tech and how advanced it gets, humans relate and crave connection with each other, and it's only going to make that more valuable.

TC: Well, as it relates to my business. So we have all these cool tools. As I tell my associates, at the end of the day, those tools enhance, accelerate, make us look better. But at the end of the day, the substance behind it is coming from us. \

CM: I tell everybody that AI is great but I still need creativity in context, and without that, AI is nothing.

TC: The authenticity of having a real person, having a real conversation when talking about transacting real estate, real, real, real. If it's AI, it's not real.

CM: It’s not real. It's a tool. It’s an assistant. It's great. We use it, full stop. But the creativity, the context, there's always somebody that is pulling those pieces together. There's a human there, there's a conversation that's happening.

TC: You know how much I love to argue and debate? I have gotten into some unbelievable debates with AI over stuff.

CM: I cannot wait to get into this.

TC: It's crazy. ChatGPT is convinced it's right about real estate stuff. I just had a client send me this report, I'm like, this is garbage, the whole foundation of this is garbage, but it's convinced that it's right.

CM: We had a client do the same thing and they didn't even change the name of it. It's still said Claude. And I was like, this isn’t original and also, by the way, half of this is wrong because the facts are wrong.

TC: Right.

CM: I know a lot of people are concerned, your world, my world, anyone in the service industry, any industry, is concerned. But, we'll navigate that too and we’ll still be here.

TC: There's no question that there are tools and there's efficiency, you know, I can take a lease document, drop it in and say, here, compare this to the original, tell me what the differences are and then 30 seconds later-

CM: By the way, cite that so I know you're not hallucinating.

TC: That exercise would have taken me hours and I can get that done in minutes.

CM: Yes.

TC: It's awesome.

CM: Same here, I can take spreadsheets. I can do data comparisons. You have to do this just by hand. It was awful, drudgery, terrible, not fun work. Now, I can take that time and I can put it into more creativity, more problem-solving, and what more strategy, what people want, right? Instead of I'm really sorry, but half of your budget is just dealing with this trudge work that's necessary. I can't be engineered out of the process. Now, it's still part of the process, but it's only this much of the process. That's the positive side to it. Yes, but we will come back, and we'll talk about all the things AI.

TC: I look forward to it.

CM: All right. We'll see you next time.

TC: I'm back here whenever you say the word.

CM: All right, we'll do part two.

TC: Thank you, thank you again, Christina.

CM: Thank you.