Maine Real Estate & Waterfront Business Part 2: Chris DiMillo on Family, Real Estate, and the Portland Waterfront

In this second half of my conversation with Chris DiMillo, owner of DiMillo’s Yacht Sales, we dive deeper into how he expanded his family’s Maine waterfront legacy — growing the yacht brokerage business beyond Portland to Long Island, New York and the eastern shore of Maryland — all while maintaining a culture grounded in hospitality, service, and relationships.

Chris shares his insights on:

🌊 Scaling with purpose: How a single boat sale led to multi-state expansion and a thriving 70-person company.

⚓ Company culture: The “hospitality DNA” inherited from his father that drives both employee loyalty and exceptional client service.

💡 Adaptability and resilience: How the COVID-19 pandemic reshaped the boating industry — from shutdowns to record demand.

🧭 Vision for Portland’s waterfront: Chris’s candid take on what “highest and best use” should mean for the city’s working waterfront and development future.

💬 Personal reflections: On family legacy, mentoring the next generation, and what his father would think of the business today.

Chris’s story is a quintessential example of Maine entrepreneurship — rooted in family, built on service, and always looking toward the horizon.

Links Mentioned:

🛥️ DiMillo’s Yacht Sales: https://www.dimillosyachtsales.com

⚓ DiMillo’s Marina: https://www.dimillosmarina.com

🍽️ DiMillo’s on the Water (Restaurant): https://www.dimillos.com

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Transcript

Elise Kiely: [00:00:00] Welcome to Elegant Maine Living, where we explore the beauty, charm and sophistication of life in Maine. My name is Elise Kiely, your host, and a real estate advisor with Legacy Properties Sotheby's International Realty. On each episode, we dive into Maine's residential real estate market, sharing key trends, inventory, insights, and notable sales, while also highlighting the extraordinary lifestyle that makes Maine such a special place to live, work, and play.

Whether you're seeking a coastal retreat, a vibrant community, or an escape into nature, Elegant Maine Living is your guide to the homes and experiences that define our great state. Let's get [00:01:00] started. Chris. In the first half of our conversation, we talked about your father's incredible story, how as a seventh grader, he dropped out of school to work to support his family, and then went on to acquire some of the most valuable waterfront real estate in Maine.

And how that success evolved from a parking lot to a restaurant and then the marina and ultimately inspired you to start your own brokerage business. In this second half, I'm excited to dive into how you grew your brokerage, how you expanded it beyond Maine, built such a strong company culture, and of course how COVID reshaped the business.

And I also want to hear your thoughts on what you think should happen with Portland's waterfront. My impression of how you run the business just from knowing you from real estate and your reputation is that you were very intentional about your business and have a very specific culture that you apply to your business.

Could you talk a little bit about that? 

Chris DiMillo: Sure. I think that growing up, seeing my [00:02:00] father, hospitality has always been. I it runs in me and I enjoy it. I enjoy people. I enjoy meeting people. I enjoy getting great service and I enjoy giving great service. And it, and that's the culture that, that we have formed in my company.

And I have, i've been lucky to found amazing people that work for me. And 

Elise Kiely: how many people work for you? 

Chris DiMillo: About 70, 70 b between the two businesses. 

Yeah. And that's including my locations in New York and Maryland as well.

Elise Kiely: Yeah. We want to talk about that in a minute. Yeah. How you've expanded because you're not just in Portland, Maine.

Just not in Portland. No. So you have about 70 employees. Wow. I didn't realize it was that big. 

Chris DiMillo: And and many. many over 10 years, many over 15 years, several 20 years. And it just changes. I do not know if it changes, but it really having that longevity with all these staff, they're able to continue the culture that we created together and show all the new people what we [00:03:00] do.

And how we're supposed to do it. 

Elise Kiely: And is that hard to create a common culture when you have multiple locations up and down the East coast? 

Chris DiMillo: I, yeah it's challenging, but as long as you keep doing it and keep reminding everybody of it, and you just, your actions as the owner and leader just have to show that every time you do 

Just every day 

Elise Kiely: because you have grown that your yacht brokerage is, I want to say over 50 million. Yeah. Oh yeah. Annual sales. Yeah. Maybe it's higher than that at this point. 

Chris DiMillo: Higher than that, yeah. 

Elise Kiely: And how many boats a year do you sell roughly? 

Chris DiMillo: It really depends because the, I can have a $4 million boat or a hundred thousand dollars boat and we sell the whole thing.

So it's right. It fluctuates and it's cyclical. And honestly, other people would people don't understand this, but I don't, of course I want to grow every year, but I'm not focused on that. I'm because of the cyclical nature of it, I'm focused on keeping our customers serviced happy. Keeping the staff happy and hopefully we make a profit. 

Elise Kiely: It's a customer experience. Yeah. And the [00:04:00] employee experience. Yeah. Equally as important. 

Chris DiMillo: E equally as important. Yeah. 

Elise Kiely: Yeah. Because it, in order to acquire and retain talent, you have to have, make sure that they have a good experience as well.

Chris DiMillo: That's correct. Yeah. 

Elise Kiely: I remember, you won't remember this, but I remember when you were talking, I think you were talking to somebody else about, a maybe an award ceremony or a piece of recognition that you gave to employees and it was a rec, it was a recognition to, I think a technician, maybe even a mechanic.

Do you all service any of the boats? 

Chris DiMillo: Oh yeah. Okay. Yeah. 

Elise Kiely: Have a big service project and it was a big, it was a big to-do about the employee recognition, and I got the impression that's something you do pretty regularly to recognize employees. All different levels throughout your company, in front of the other employees?

Chris DiMillo: Yeah. We, at our annual party, sometimes semi-annual, we, handout. We want to recognize people, but we also, you get to five years, you get two tickets to somewhere. You get to 10 years, you get two tickets in a [00:05:00] week's pay, and it's just as you go up, there's more reward, but also just the recognition and them feeling my appreciation and my other managers, their appreciation for what they do.

I am often humbled by. Me going to work and seeing 70 people working for me, and sometimes it's a little overwhelming to me, but it's, I bet, but I try to. Yeah, return the favor. 

Elise Kiely: Did your father ever give you two tickets to somewhere for five years? 

Chris DiMillo: No. No. 

Although he was very generous.

I as I said, I had everything I needed and he took me to Florida once a year growing up, and and as he got on in life and he ended up, in Florida.

For parts of the winter, he would invite all his kids down and pay for the tickets, and he wanted them to be there. So he, 

yeah, 

Elise Kiely: he wanted his family around him.

Chris DiMillo: He did. Yeah. 

Yeah. That's sometimes 

Elise Kiely: That's wonderful. 

Chris DiMillo: Sometimes 

he just wanted nobody around. After he left the restaurant, he wanted nobody around. A little quiet. 

Yeah, just my mother. 

Elise Kiely: Where in Florida did they go? 

Chris DiMillo: They were between Fort Lauderdale and Pompano [00:06:00] Beach. 

Elise Kiely: Oh, okay. Oh, that's right around where I go.

So let's talk about how you scaled your business. You started the yacht brokerage. You were probably in your late twenties, maybe late 

twenties, yeah. 

Yeah, late twenties. How did you, with no real brokerage experience, you'd done sales. Yeah. For pharmaceuticals. How did you start growing this? What were the skills or resources that you relied upon to?

Chris DiMillo: I'm an observer. I I like to. Watch what other people are doing and I like to listen. I try to, you wouldn't know it in this podcast, but I try to listen more than I talk. So that's really, I'm just not afraid to try things and start things. Yeah. And and I can always modify them and, never

Elise Kiely: what was the first boat you sold?

Chris DiMillo: I sold a 36 foot tiara. And I think if it wasn't the first, it was very close to a tenant at the marina. Very nice couple. The boat was in in the Great Lakes and we went out there and surveyed it and they brought it back and it was probably a hundred thousand dollars. I think it was $107,000 at the time.

Yeah. 

Elise Kiely: And big deal. You must have been thrilled. That's a big deal. 

Chris DiMillo: That's a big deal. [00:07:00] That's a big deal. 

Elise Kiely: Good for you. Good for you. And then it just grew and grew. And you hired brokers. 

Chris DiMillo: And I hired brokers. And really what changed? Two things changed. The business was my very close friend Mark, closest friend, my whole life, best friend my whole life.

He was an avid golfer and he played golf at Family Country Club with Bentley Collins, who was the marketing manager at Sabre Yachts. And they ended up on a foursome one time and started chatting about boats and this and that and whatever. My buddy Mark said, you should really talk to my friend Chris about his boat dealership and I think he would do a good job for you. And so we ended up meeting and took a few more meetings and eventually I I was able to sign up on that. And that's really changed the trajectory of my business, 

which shows that it's stems from relationships.

Relationships. 

Elise Kiely: Your reputation is a hard worker. A problem solver said that your buddy Mark, even though he is your buddy, 

Chris DiMillo: he knew that he wouldn't be embarrassed to recommend it. 

Elise Kiely: Exactly. Exactly. So that was really a significant turning [00:08:00] point for Yeah. 

Chris DiMillo: So that, that's one. And then the other is that I to say that the service in the boat industry is so bad that my very mediocre service seems amazing to people.

So just trying to do the right thing all the time and really, just. Going the extra mile to keep a customer boating, keep them happy.

Elise Kiely: I think you said something really interesting, Chris. This is, this will be one of my takeaways from the podcast. You like to get good service, you appreciate it.

And you recognize it.

Chris DiMillo: I do. 

Elise Kiely: And you like, because of that, you like to give, maybe not because of it, but be, but you also like to give good service. I get you find that rewarding much 

joy out of giving good services. I, as

Chris DiMillo: I do, getting good service 

and I, I.

Elise Kiely: I feel the same way. I think that we have a, I have a responsibility to give as good a service to my clients as possible.

I want their experience to be very pleasant. And that means doing things that they have no, that they don't even see, they're not even aware of. And it even could be what time of day is the [00:09:00] showing or what order is the house being shown thinking of their needs and what is gonna make them the most comfortable so that they have the best experience.

That's the only way I can describe that. 

Chris DiMillo: And, and the art of that which you are very good at, is making them feel like this is just happening. That you're not making an effort to do it, that it's just what you do. And. And it's what you offer and you're not going out of your way to do it because this is what you do.

Elise Kiely: It's all about systems. Yeah, it's all about systems. I liken it as if I was having someone into my home for a cocktail party or a dinner party, I would want to make sure they were comfortable. I would want to make sure the house looked a certain way, that the food was presented a certain way, that the food tasted a certain way.

Not for my own sake, but because I want them to have a really good experience. Yeah. 

And when things are going wrong. The ability to to mask that a little bit. If they don't need to know. Sometimes they need to know. But if they don't need to know, you absorb the problem and keep delivering the experience and [00:10:00] That's right.

Chris DiMillo: You're good at it. And I think my team is good at it. 

Elise Kiely: You not to go too far down this rabbit hole. When I was practicing law in a boutique law firm in DC, the named partner who was one of my mentors, he's just so smart. And so strategic, he thought of the law firm, like a box, a black box client asks a question.

There's lots of stuff going on in the box that nobody needs to see. And then an answer comes out, they just want to see the answer. And they don't, they shouldn't have to be exposed to everything that's going on in the box. That's right. Sausage being made, if you will. Yeah. So I think that's a wonderful attribute.

And so you scaled the business here in Portland. And then when did you decide to expand beyond Portland? 

I would say that that I always had the desire to do it and and I was looking for the opportunities, 2006 that Saber and Saber's sort of sister company Back Coves, which is built in Rockland, owned by the same families, different plants, different engineering different product [00:11:00] lines. But some synergy came available down in in, on Long Island. And I was lucky enough to be the first in line to get it. And I went down there and, and met with the owner who was a very wealthy man, and this was his hobby and he was just burned out on doing it, didn't want to do it anymore.

And he, so we put a deal together. So I became the dealer for Sabre and Back Cove on Long Island. So that was the next step. 

That's, it's not easy to get from Portland to Long Island.

Chris DiMillo: No, no. But that was okay. That was okay. Yeah. I like to travel. Yeah, I like the, yeah, and I would fly. And then I would have all the problems with flying and I would say I'll never fly again. And then the next time I'd drive and I'd have all the problems with driving, I'd say I never drive again. 

Elise Kiely: Should have taken a boat. 

Chris DiMillo: Yeah, I guess 

That has all its own problems, 

Elise Kiely: And how big was that Marina? 

So there, 

Chris DiMillo: oh, that's just the brokerage.

Yeah. That there, I just have a brokerage and a service department. So I have three brokers. An admin person? No, two admin people, service manager. So [00:12:00] probably 10 people working there. Yeah. Yeah. 

Elise Kiely: And then you grew beyond, so that was out, out of Maine. Yeah. 

Chris DiMillo: So then I, I, I try to keep doing what I know, and what I'm good at.

And I've tried some other things, other boat brands, and not a lot of it has worked out well, turns out I'm a one trick pony selling these Sabres and Back Coves, but I'm very good at it. And so this is just a little bit of a funny story about DiMillo's. I am at the Annapolis Boat show down there with a client.

I have nothing to do with Maryland at the time, and. I am standing on the back of a boat and I'm wearing a DiMillo shirt. This guy gets on the boat and he looks at my shirt and he says, oh, DiMillo's this great restaurant. I keep my boat up in Maine from time to time. And I go into the restaurant and he said, it's great.

And I said, oh, very nice. And so he struck up, a little bit of a dialogue with him and of course find out he's a serial boat buyer. And so we get to be, a little friendlier and the one year [00:13:00] later, 'because people don't buy million dollar things on a whim. Usually it does happen.

One year later, at the next Annapolis boat show, he ends up coming, we meet, we talk, and he ends up buying a boat and then. He had a great experience. 

Elise Kiely: Were you still wearing the Damilla shirt? 

Chris DiMillo: Of course, of course. Surprised we're not wearing it right now. Then he had a great experience with my people up in Maine, 'because he took delivery up in Maine.

He want, use the boat, but up Maine. And he believed in me, believed in the Sabre product. And he said, I want to buy the Sabre dealership in Maryland. And, so I said, all right I'm in. And for, he was a wealthy guy. And he was able to just do it without financing and without me, except he wanted, he had the finances, I had the knowledge and the experience.

So he ended up buying the dealership. We became partners and I bought him out a few years after, but. I just always think about that as the how the brand that my father [00:14:00] created was the impetus to me acquiring what's now probably a third, if not more, of the value of my business, 

Elise Kiely: The in Maryland Eastern 

Shore, Maryland location.

Chris DiMillo: Yeah. So I'm on the eastern shore of Maryland and also the Western shore south of Annapolis. Wow. So I have two locations down there. Wow. And I own the Marinas either side of the Bay Bridge. That's right. 

Yeah. That's, oh, that's fantastic. All from the brand. He's 

a great client and a great friend and he he bought a boat last fall and, he called me this spring and he's that's just not right. And then we started talking about the next, he's sell this one. He said, started talking about the next one and he said, I'm a terrible serial boat buyer. And I said, no. In fact, you are a very good serial boat buyer 

and a good friend now at this point too.

Elise Kiely: Yes, exactly. That's fantastic. That's fantastic. And so is Maryland, the southern most location that you have? It's, and you also have some other locations in Kenny Bunk Port and kittery, I think 

Chris DiMillo: I wasn't kittery, so we're just in Kennebunkport now and in stay tuned. There's more to come.

There's more [00:15:00] to come. Yeah. I don't, sooner than later. 

Elise Kiely: Grass doesn't grow under your feet. There's always, you're always looking for the next Yeah. Modification, expansion of the business

Chris DiMillo: might just be my short attention span, but, 

and 

Elise Kiely: my sense is in the. In the yacht brokerage and marina business that there's been some consolidation. Because it's, the barriers to entry can be pretty high.

And but you've resisted that. Is that because your desire for independence, just like when you came back, you said, I've, I'll, I want to do this, but I want to do this on my own. Vis-a-vis your father. Is it the same philosophy? 

Chris DiMillo: Yeah. And I it's not my soul.

Reason for not pursuing being acquired or, whatever. But my son wants to be in the business. He now works in the marina in the summer while he's not school. 

Elise Kiely: And he's college age right now. 

Chris DiMillo: Yeah. He's college age. Yeah. So goes to school in Florida in the, during the year and comes back and works in the summer.

My nephew runs the marina. And also I just, I have amazing people that work for me and I would have a difficult time [00:16:00] not knowing what. The next thing is for them. 

Elise Kiely: Yeah. You feel protective?

Chris DiMillo: Yeah, I do. Yeah. 

Elise Kiely: And I imagine you really, I can tell you really love what you do.

Chris DiMillo: I do. I, frankly, I'm a little over it now, but I've been doing it long enough that I'm more interested in, I thrived on transactions.

And finding a client. And finding them the boat and closing the deal, and I thrived on it. Not so much anymore. Yeah. But I have 12 salespeople that do that and they're thriving on it now. So I have a little more interest in bigger picture stuff and strategy. 

Elise Kiely: More strategy and yeah. And in real estate and. 

Chris DiMillo: Yeah, 

that's what expansion, 

Elise Kiely: that's why you and I are gonna keep talking, Chris. Okay. It's all about the, all, all about the real estate. Let's talk about some stories. You deal with some really interesting people. We both do. In the businesses that we have, you deal with a lot of very wealthy sophisticated, educated. People and you can't sell the number of boats and the volume [00:17:00] in sales that you do without there being some really crazy stories out there. What's if someone's going to ask you at a cocktail party, what's the craziest experience you've had? What's one of those stories? 

Chris DiMillo: I can just think of one that's happening right now.

Perfect. 

That yesterday we got a call, and this is, I'm laughing because nobody got hurt. We got a call from someone who sold, we sold the boat to three years ago, and he was in Newport with the boat and he's an older gentleman. He had a captain on the boat with him, and his family was on the boat, but they were staying in the hotel.

Somehow in the middle of the night, the boat burnt to the waterline. 

Elise Kiely: Nobody was staying on the boat. 

Chris DiMillo: Nobody was staying on the boat. 

Elise Kiely: Not even the captain. 

Chris DiMillo: No, 

nobody. So everybody was safe. 

Elise Kiely: How did that happen? And of course happen. 

Chris DiMillo: He calls my salesperson and my salesperson is completely alarmed at, it's just a lot to hear, but the client says, when can I get another one?

And of course we say, we just happen to have one that we can get for you. [00:18:00] 

Elise Kiely: We could have it in Newport in two days. Yes, exactly. 

That's crazy. How did it burn? 

Chris DiMillo: I, it's up for, up for investigation. Up for investigation. 

Oh. 'because it just happened. 

Elise Kiely: Just happened. 

Chris DiMillo: So it 

literally just happened yesterday. 

Elise Kiely: Wow. Oh, that's crazy.

And scary. 

Chris DiMillo: And yeah. You have the boat connected with a shore power cord to a fitting on the dock, the salt air, the loose connection, the whatever. All the things that add up to an electrical fire. So that's probably where it came from. 

Elise Kiely: Have you ever had. Because you sell both new boats through Sabre, and you do resales for people. Yeah. Have you ever had somebody commit to a very high end boat and then the transaction goes south 

Chris DiMillo: in terms of go south 

Elise Kiely: in the seller says they're not going to sell after all, or the buyer says, you know what? I got over my skis. I really can't do this. 

Chris DiMillo: Yeah, I have I actually never had a seller. I declined to continue on our purchase ever. And I've had many buyers there, but because no one [00:19:00] needs a boat and the bane of the yacht broker's existence, nobody needs these things and they're a monumentally bad use of capital purchasing.

One of these things, 

Elise Kiely: you're not in charge of marketing if you say that. 

Chris DiMillo: But the contracts we have are. Amazingly buyer friendly and you get a long time to figure out whether you want to do it or not with no risk, 

Elise Kiely: and I imagine there's a due diligence period. It's a due diligence period like there is with a house.

Chris DiMillo: Yeah. 

Yeah. And you have to act to bind the contract if you don't act the contract just as all it terminates on its own. Yeah. So I, we really don't have a lot of it. I've had a few times where people have giving me a little run around in buying new boats. And generally I, someone doesn't want to buy, someone doesn't want to buy the thing I give them, I just let them out of it.

Making somebody do something that they don't want to do is never a good business decision or recipe for sleeping well at night. But there have been times where I've made them. 

Elise Kiely: You made, [00:20:00] and I imagine it's also how people approach it. 

Chris DiMillo: Oh, completely. 

Elise Kiely: And if someone approaches it, Chris, I got over my skis.

Yeah. I got my ego got in the way. Help me out. That's going to have one reaction. If it's bluster and saber saddling. Yeah. Then that might be a different response. 

Chris DiMillo: Yeah. And that different response rarely comes out. Yeah. 

Yeah. It has to from time to time. 

Elise Kiely: So when people are buying a new boat and they can customize it.

What are some of the most unusual or unexpected things that people have asked for in their boats? Because you deal with some pretty big boats in Saber. What's the biggest new con? 

Chris DiMillo: 66 feet 

now 

Elise Kiely: it's a big boat. 

Chris DiMillo: I think a the, a lot of people, because people don't keep boats that long.

They just don't average. 

Elise Kiely: What's the average age? 

Chris DiMillo: Average ownership is five years and it's, I think it's actually shrinking as we go. As populations attention span gets shorter and so they, most people think through. When they're doing, when they're building their boat about whoever the next person is, where they were going to want to.

[00:21:00] So they're not so customized that they're so unique. But recently we did have a boat in the owner had dogs and he put in a dog wash station in his boat. In his boat, and he thought it was the most amazing thing ever. And that's what people do when it's their idea. They think it's the most amazing thing ever.

And everybody's going start doing this. Yeah. Yeah. And then an, and I remember a couple years ago I sold the boat to somebody and he modified the way the seating was in the salon. 'cause he just thought this was going be the most amazing thing. I resold the boat for him a year later and put it back to the original one original way, which.

Elise Kiely: If it's been tried and true. Yeah, exactly. You want to be pretty vanilla. Yeah. Yeah. If you're going up, same thing in a house, you don't want to be so unusual that it's going to make things difficult for the next buyer. That's interesting. Dog washing station when there's water all around you.

That's fantastic. Chris, let's talk a little bit now about COVID. And what that, what happened during COVID? Do you remember? Back in March of 20? Yeah. [00:22:00] Yeah. How, what were you thinking in the very beginning?

Chris DiMillo: Well. The first thing I was thinking was that I was probably amongst the first people in Maine with COVID.

Elise Kiely: Really? 

Chris DiMillo: Yeah. I went, took my son and a couple of his friends skiing in Utah, and we arrived back on the 15th of March. 

Elise Kiely: All right. Ground zero. 

Chris DiMillo: Yeah. So either the travel out there, the travel back, I don't know what. 

Elise Kiely: You didn't feel good. 

Chris DiMillo: I didn't feel good. My son didn't feel good, but we were fortunate that we.

Just had mild symptoms and yeah, cough that wouldn't go away. Fever, sweats, some weird, symptoms. But I, I guess we were living in denial and we didn't. What is it? Are you supposed to social distance or, yeah. And mask, you didn't take the preventative measures. Yeah. Yeah. And, 

And really at that time it was so it was at the, it was at the beginning.

It was the very beginning.

Elise Kiely: Beginning. We all thought this was gonna be two weeks. 

Chris DiMillo: Yeah. There were zero recorded cases in Maine, because they would announce 'em on the news every night. There was zero. 

Elise Kiely: And this is when you were [00:23:00] living in Portland, in the condo?

Yeah.

Okay. And oh, wow. Yeah. 

Chris DiMillo: And unfortunately I gave it to my sister and my brother, and then my sister gave it to my brother-in-law, and they all got very sick. Oh, 

I'm sorry. Yeah. 

Hospitalized. Wow. Wow, I'm so sorry. Yeah, it was not good. It was tough and I kept saying it wasn't me, but we all knew it was.

But after they all got better, I said, really? You ought be thanking me. That's right. Because now you're immune. Now you're immune. And they all say, you're welcome. So anyways, we so worked through that. But yeah, I'm in the boat business. 

It 

Elise Kiely: Did you know right away that boats were going to be one of the things that people would just gravitate to?

Chris DiMillo: No. 

Because the local governments and were shutting down, were down marinas and shut. Yeah. So everything was shutting down. All my employees were staying home and, I didn't know I was gonna get the PPP money, but it was certainly going to not stop paying them. So I'm paying all these people to stay home and the boat business as cyclical as it is, [00:24:00] nine 11 was a turmoil, 2008, 2009, the recession. That was a disaster. 

It's the first thing to go and Right. Discretionary 

purchases. Yeah. 

Elise Kiely: And and you probably had people living on their boats maybe. Yeah. In the marina. 

Chris DiMillo: Yep. Yeah. 

So what we just saw was that. Yeah, everything just slowed down. But it wasn't an immediate fear stop.

Yeah. Yeah. And it wasn't an immediate, it was more I'm going to, there was no panic selling uhhuh, which would've been changed the whole dynamic, and then, I don't know, within three months we could start to see was that people were. Saying, okay, yeah, this is something I can do. 

Or not even.

Elise Kiely: Okay. You must have had a, your phones must have been ringing off the hook with people saying, how can I get a boat? I need to, 

Chris DiMillo: yeah. But it was gradual. 

Elise Kiely: So it wasn't overnight. 

Chris DiMillo: It wasn't overnight. It was gradual, so from March to the fall boat show season, that's when it really started to pick up.

And, but then the flip side of it is that the manufacturers. Their [00:25:00] capacity all went down. So there was a a frenzy of buying in buyers, but the supply wasn't there. So that, that, so you had this pent up demand with no supply, like real estate. Yeah. So we were doing a normal number of transactions.

We weren't doing more transactions, but we were making more money on every transaction. Yeah. Because people were paying more for the boats. If I had a new boat, we could, we didn't have to negotiate when it so 

it was a really robust time. It was, yeah, it 

was. 

Elise Kiely: And did you see any changes demographically in your buyers?

Were they older, younger? 

Chris DiMillo: Maybe a little younger. Little younger, yeah. Interesting. Yeah. Interesting. 

Elise Kiely: Yeah, it's such an, it was such a unique time when the, in real estate, it was so much fear and then so much fear of I'm not gonna get a house. Yeah. And so it, and that lasted a good. Two and a half, almost three years.

Yeah. Did it last that long in, in the boat? 

Chris DiMillo: Same. Same. Yeah. And I I believe we still have a lasting effect from it, that people have a greater sense of their own mortality [00:26:00] and they are willing to spend money a little more freely. People think about wealthy people, that they have so much money, they don't care what they do with it.

The wealthy people I know. Are the hardest to make a deal with sometimes because they earned their money and they just don't spend it without really thinking through it. And I've seen that loosen up a little bit because people want to, I've seen, the wealth transfer. People are doing that before to their next generation doing it. Before they would've normally. Because they want their children to enjoy some of it. I've seen them retiring, the people selling their businesses, all of that. Not solely caused by the pandemic, but certainly influenced. 

It is interesting to have the pandemic happen, right?

Elise Kiely: When this great wealth transfer sure. Was about to take place and I see it in real estate too. I affectionately call them LABBs. Luxury active baby boomers. [00:27:00] Yeah. And they all physically active. They want to be skiing, they want to be boating. They playing tennis, they're. They're healthy and health is very important and they have done very well in the stock market. They've done very well in real estate portfolio and they have inherited some wealth and they are gifting it to adult children. Significant cash so that they can be competitive in their in their first house. And it's really interesting to see the para the effect of COVID and maybe that accelerated it a little bit.

I don't know, but it's, I'm sure it did. I'm certain of it. Yeah. It's definite then. And are you seeing the high end of boat sales driving the market? In boat sales. 

Chris DiMillo: Yeah. 

Elise Kiely: More than the entry or middle end.

Chris DiMillo: Yeah. And for two years after the pandemic started, it was, it didn't matter what segment it was.

But now it's really the higher end, the high end. 

Elise Kiely: And what is the high end for a boat sale? 

Chris DiMillo: That's all relative, right? So my high end is, above my high end is above 2 million. But I would say our real. Sort of [00:28:00] success spot is seven 50 to a 750,000 to a million and a half.

Elise Kiely: So that's your bread and butter. Yeah. 

And the above 2 million is the maybe 10% or something like that? 

Chris DiMillo: Yeah. Yeah, exactly. Yeah. And, and just interesting too, the price of everything has changed due to all kinds of things. I don't know that tariffs have. Really affected pricing yet, but inflation price of labor, E everything, yeah has changed. So I, when I started in this business, my entry level boat was a hundred thousand dollars. My entry level boat is now $900,000. 

Wow. 

And I don't love that. I, yeah. I'm asking the manufacturers to build me something smaller and simpler, because this is how we get people 

into boating, into the family.

That's right because they, if the entry price is too high, then you're going to exclude. And that will age out. 

Elise Kiely: Your current customers will age out. 

Chris DiMillo: That's right. Yeah. 

Elise Kiely: That's very interesting. Chris, let's shift a little bit. Let's talk about Portland's waterfront. And how you've seen it change over the years, and [00:29:00] where do you see it going with the current vision?

With the vision of the current let's, let me back up. Let's try this. Yeah. If Chris DiMillo was a king for a day or maybe more than one day, where do you think the highest and best use of the Portland waterfront would be? What would be your vision to and when I say maximize value, I don't mean just for the DeMillo business enterprises.

Yeah. What is the highest and best use for Portland for the waterfront? 

Chris DiMillo: Certainly preserving the working waterfront is paramount to keeping Portland what it is.

Yeah. But we have so much of that and it's, it, we, in my opinion, we're wasting opportunity by not allowing a little bit more development.

Yeah. 

Because there's just vacant land and vacant dock space on commercial that is doing nothing, run down buildings because you can't support [00:30:00] the cost of the infrastructure. On what you can get With the permitted uses. The permitted uses, yes. 

Elise Kiely: I feel your father would be so frustrated. 

Chris DiMillo: Oh yeah.

By all this, potential. I would say that the and it doesn't really matter to me or my family because we're happy doing what I'm doing. My brothers are happy running the restaurant. I'm happy doing what I'm doing. We have a parking lot that we're very fortunate is, has been a great, produced a great return for us, but the current zoning has probably reduced the value of our property by probably 66%.

Wow. From what it could be if it was a little bit more liberal. And I just don't see what it is that the, and it's not it's, a lot of it has to do with the council, but a, the people, the referendum right. Five, six years ago was what really? Put the lockdown on on development right now.

Elise Kiely: And I know your brother was very involved in a lot of the counter to that of the referendum. Yeah. And so you all had, do I think, my perception is you all are stewards of [00:31:00] Portland and you participate. Your brother didn't need to participate in that. It's not, 

Chris DiMillo: no, I call him the def facto mayor.

That's right. He knows everybody and he is all about Portland and he's and a big supporter. A big supporter and a big giver of his time that he doesn't need to do.

Elise Kiely: And would you see, do you think the best use is commercial development, residential development?

Chris DiMillo: Mixed use? Mixed, yeah. Mixed. 

Yeah. What's wrong with residential development on the waterfront? What's wrong with that? I if you aren't displacing something to produce the residential development, but there are a million ways to do that.

It's just that people just can't see past it and they just want to say no.

Elise Kiely: That's how you and I met Chris was from the residential development. From the condo Yeah, sure. That, that you bought. Yeah. And you came back to Portland coming back to your father's roots not far from where your father grew up. Yeah. Was the property you bought, which you no longer lived there.

Yeah. But that was a great experience. And it allowed you to be able to walk to and from work, love it, and be part of the [00:32:00] community. Which I think you really enjoy being part of see and be seen type thing. Yeah. 

Chris DiMillo: I do and I don't think that we should give people grief for wanting that.

And I also have a view that I'm not sure why everybody feels that they have the right to live on the peninsula. You know that I, when I first bought my house, I didn't buy in the peninsula. 

Elise Kiely: And you didn't grow up on the peninsula. 

Chris DiMillo: And I didn't grow up in the peninsula. My parents didn't buy a house on the west end or the, fancy house on the east end.

We live in a very modest home because that's what they could afford.

And I, I think I, I just don't think there's anything wrong with the pro the values going up. There are a lot of people in the city of Portland that have benefited from the values going up. More people have benefited from the values going up than haven't.

And that's just disappointing to me. And I, if we just talk about general, the Portland in general, this whole thing with the music venue Oh yeah. That wants to go in town. These are two local guys that were. A father and son, and the father was instrumental in [00:33:00] the development of the old Port, and he just does great projects and they want to take a vacant piece of property and put something in it that'll drive more people to Portland.

And all of a sudden, that's not what we want, anymore want. It look, all of the people that live here, work at restaurants, work at hotels work in all of the ancillary business that support this. Why don't we want more? Another reason for people to come here besides a restaurant.

Traffic. Who cares? A little traffic will be just okay. People change is 

hard. Change. Change is, no, it's not. Change is hard. They think it's hard. It's not. They think it's hard. 

Elise Kiely: It's it's the same thing with the resistance to the Roux Institute. Yo. 

Chris DiMillo: Exactly. What a wonderful thing. Amazing. For Portland. Yeah. 

Elise Kiely: And we're not gonna be Portland of the late 18 hundreds or 1930s or 1950s. Yeah. 

Chris DiMillo: And nor should we be, and nor should we be and we shouldn't be at of you. You started with asking about the change if you walked around the Portland waterfront in 1980 before, my father sparked what was going on down there.

It was awful. Which is, it was dirty. 

Elise Kiely: Which is why it took courage for your [00:34:00] father to do that. 

Chris DiMillo: Absolutely. Because he had to have a vision. People are not recognizing they the courage of the people that took the risk to build what's there now. Fighting an uphill battle at all times.

And they just think that people who are against every kind of development, just that they're taking advantage and they're, whatever. They're not. Yeah. 

Elise Kiely: Chris, this has been, I could talk to you for hours and I hope you come back. 'because I would love after a few years, let's see where the Portland Waterfront is.

Let's see where DiMillos is. I think there's probably some news announcements I can tell from. Looking at your facial expression, 

Chris DiMillo: there'll be some announcements. 

Elise Kiely: I would love to have you back and share more of your insight. 

Chris DiMillo: Be glad to come. 

Elise Kiely: I always end with a few key signature questions for people. So if you don't mind, I'll, no, I'll ask you please. Where do you find elegance in Maine? And by elegance I don't mean formal, stuffy. Yeah. Beauty. 

Chris DiMillo: I can find it in so many places. I can find it going into scale's restaurant. I [00:35:00] can find it going into Acadia. I can find it standing on the top of the beehive and looking out and seeing the amazing view from there.

Walking around the Eastern promenade, boating around the Eastern promenade, looking at just how magnificent that real estate is there in the history. It's we're so lucky to live here. It's so lucky. It's so interesting, 

Elise Kiely: so lucky to live here in the summer. It's right. We're going to get you back a little bit in the winter.

What's your favorite place in Maine? 

Chris DiMillo: I just love Portland and I go to other places and I find them charming and I, I skied for years at Sugarloaf and I'm just past that chapter, but that was an amazing experience for me and my family. I, I enjoyed that. I enjoyed the, I, it's just hard to say I really love Portland.

Yeah. But I love the Midcoast, I love Bar Harbor. I love 

Elise Kiely: Chris lynch, said Casco Bay. And I thought that sort of sums it up because you're right outside Portland and you have the calendar islands 

Chris DiMillo: seriously when you fly in to Portland and you I forget the name of the route that it is, where you fly in to I think it's the harbor entrance or whatever, but, and you fly over and you see all the [00:36:00] islands.

It's, and then you come over and you're looking down over the old Portland waterfront. It's just, it's beautiful. It's just, it's spectacular. Yeah. 

It's so authentic. Favorite coffee shop.

Wow. I guess I'm basic. I really like Dunking Donuts. 

Elise Kiely: There you go. 

That's perfect. I haven't heard that one yet, so that's fantastic.

Is there one near you?

Chris DiMillo: There's one at one city center there. You okay. That's perfect. What's the most influential, and by the way, all of them in town owned by a local. Yes. Not, yeah. Doesn't mean it's, I'm supporting some capitalist organization. Owned by a local and employing great people that the people have been there forever.

Elise Kiely: Anyway. Said. Said. What's a, in a influential, I won't say the most 'because that's too hard. Influential book or talk that you've heard that really had an impact to you on your business? 

Chris DiMillo: I, I have read this a couple times and I thought it was really good. It called BE 2.0 B 2.02 BE 2.0 So you want to, you want to Be right?

2.0. The next thing, 

Elise Kiely: like Chris DiMillo 2.0. Yes. 

Chris DiMillo: [00:37:00] Exactly. Always trying to improve. 

Elise Kiely: Play up, improve, yeah. 

Chris DiMillo: Yeah. And I think the most memorable thing that I took out of that was we all know how important it is to have the right people working for you. Clearly I know that. But equally important is to know when you have the wrong people working for you.

And how the wrong people can really change quickly, change a culture that is always doing the right thing and always has the right attitude. So in the book they say, you also got to know when to get the wrong people off the bus. 

Off the bus. 

Elise Kiely: Yeah. It's not fair to the good people. It isn't or the right people.

Yeah. It's not bad or good. Yeah. It's just. Yeah you have to know the right people in the right seats. On the bus. 

So last question for you, if your father was sitting here what do you think he would say about you and your siblings and the stewardship of the businesses that you've developed and grown?

I think he would be very proud and think it's really, [00:38:00] if he walked into the restaurant and see what it looks like today and what they're doing, I think he would be very proud. I think he always. Wondered why I wanted to be in the boat sales business. He thought that was a terrible idea.

In fact, he said to me one time, if you wanted to be in the boat sales business and you had any brains, you would be doing this in Fort Lauderdale. And but 

I think he would be very proud. He would have a hard time expressing it. 

But I would know it. 

You would know it. Yeah. Yeah. 

And that's all that matters.

Yeah. I fib one more question, one more, one more question for you. What advice would you give to somebody who's in their late twenties moving home from Southern California or Chicago or Southeast America of wanting to start their own business? 

Chris DiMillo: I'm asked this quite a bit from young people that I just come across that want to be in the boat business mostly. And I think the biggest mistake I made, which if I could go back and rectify, was I didn't. My father was a, was always worried about the cost of everything, the cost of the butter, the cost of the electricity, the cost of the french fries, the cost of the staffing.

[00:39:00] And he ingrained that into me as important, which it is. But if I had to go back, I would've, I could have done more and better earlier if I had more people. 

Elise Kiely: And you were hesitant to scale? 

Chris DiMillo: I was. I was hesitant to scale exactly. And I should have done that earlier. 

Elise Kiely: Yeah, that's risky. Chris, thank you so much.

I really appreciate your being here. This has been super fun for me. Wonderful. Thank you for joining us on Elegant Maine Living, and remember, if you are dreaming of a lifestyle in Maine or already living it, this podcast is for you. Be sure to subscribe so you don't miss an episode. And I invite you to take this journey with me.

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