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

In this episode of Elegant Maine Living, I sit down with my friend and client, Chris DiMillo, whose family name is synonymous with Portland’s waterfront. The word of the day is DiMillo—because that single name tells a story of hard work, family, entrepreneurship, and Maine grit.

Chris shares his father’s remarkable journey—growing up on Munjoy Hill, leaving school at age 12 to help support his family, and ultimately building an empire that would shape the heart of Portland. From running a grocery store to creating one of Maine’s most iconic restaurants, his father’s story embodies the spirit of possibility that defines the Maine lifestyle.

We also talk about Chris’s own path—leaving Maine for California, building a career in medical sales, and then returning home to take over the marina and launch DiMillo’s Yacht Sales
, now a thriving business with multiple East Coast locations. Chris shares what it’s like to lead a team of 70, grow a family business with intention, and continue his father’s legacy on Portland’s working waterfront through DiMillo’s Marina
.

Our conversation also turns to real estate—how his father’s early investments helped transform Commercial Street and how zoning and development continue to shape Maine real estate today. Chris offers thoughtful insight into the balance between preserving Portland’s working waterfront and allowing for growth that keeps the city vibrant and sustainable.

If you’re in Portland, make time to experience the DiMillo family’s legacy firsthand at DiMillo’s on the Water
—a floating restaurant that has become a Maine landmark for locals and visitors alike.

This episode is a celebration of family, entrepreneurship, and the enduring beauty of living and working in Maine—where hard work, creativity, and community come together to define success across generations.

Links Mentioned

• DiMillo’s on the Water (Restaurant): https://www.dimillos.com/restaurant/
  
  
• DiMillo’s Marina: https://www.dimillosmarina.com/
  
  
• DiMillo’s Yacht Sales: https://www.dimillosyachtsales.com/
  
  

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Have Questions or Topic Suggestions, e-mail Elise at

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Please remember this podcast is for entertainment and educational purposes only and does not create an attorney client or real estate advisor client relationship. Please reach out to me directly if I can assist you in your real estate journey.

Transcript

Elise Kiely: [00:00:00] Welcome to Elegant Maine Living, where we explore the world of real estate with insight and intention. Each month, I share market updates to help you navigate Maine's dynamic real estate landscape, but the true elegance of real estate lies in the communities we build. So I also spotlight Maine's visionaries, entrepreneurs, and everyday leaders.

Whether you're buying, selling, or simply curious about life here, this podcast is your guide to the people and places that make Maine such an amazing place to live, work, and play. Well, let's get started. The word of the Day, you know, often I will start my podcast episodes if you listen to this podcast regularly with either a word or a number of the day.

And when I was thinking about the word or the number [00:01:00] of the day, I could have talked about multimillions in revenues, multimillions in boats, dates of acquiring strategic real estate in Portland. But frankly, the word of the day is DiMillo because that says so much. And I'm excited to welcome my friend and client, Chris DiMillo, founder and owner of DiMillo's Yacht Sales.

Chris, welcome. 

Chris DiMillo: Thank you. Glad to be here. 

Elise Kiely: It probably, when you hear that the word DiMillo says so much, you have to appreciate and recognize what your family has built in the heart of Portland, Maine. It's really extraordinary. And, and we're going to get to the incredible story of your father, who I think is really the founder of the, the real estate that you own and the businesses that you and your family own and control mm-hmm.

In that part of Portland. because I think it's such a great story, um, that I, I'm excited to get to. But let's start [00:02:00] with, let's start with your journey. Um, you come from a large family. How many brothers and sisters? 

Chris DiMillo: I have eight older brothers and sisters. I'm the youngest of nine. 

Elise Kiely: That's extraordinary that you're the youngest.

Because I think of all of the DiMillos that I know, you're all leaders. They're no troops, right? Everybody's in, everybody's in charge. You have a strong leadership thread that goes through your family. 

Chris DiMillo: Yes. We had a strong role model, 

Elise Kiely: Yes. And your parents I bet. And my parents. Yeah. And Chris, you obviously own the marina, um, on DiMillos and the yacht brokerage business.

Chris DiMillo: That's right. 

Elise Kiely: But that wasn't your first career out of school or even I think what you went to school for, was it?

Chris DiMillo: No, it wasn't. I, uh, I had a, had a vision that I was going to be a, a physician and I went to school and I had a knack for science and an interest in science. I went to school at University of Vermont for biology great school and a a minor in nutrition.

And, uh, just a, uh. Perfect storm of things that didn't go right. I didn't do well on my MCATs. I applied to really, [00:03:00] really good schools, and it was at a time where the economy was terrible, so everybody was applying to schools. Oh. And I actually didn't get into a medical school, so I thought I would, um, just stay in the field a little bit.

I worked for a medical equipment manufacturer in Boston and, uh, worked in house for nine months and then took a sales position in Southern California with them and, and did that for two and a half years. 

Elise Kiely: So. And you had grown up in Portland, I think, right? 

Chris DiMillo: That's correct. Yeah. 

Elise Kiely: Not, not on the peninsula. I think it was off the peninsula.

Chris DiMillo: Yeah. The Rosemont area. 

Elise Kiely: Rosemont area. So went away to college. Boston, still New England, Southern California. Yeah. That's a big change. 

Chris DiMillo: That was a big change, but it was, it was different. And I, I didn't think it would be my future, but it was certainly a, uh, uh, a great interim, um, spot. I loved it. 

Elise Kiely: And how long were you away?

Chris DiMillo: Uh, three years. 

Elise Kiely: And what, what was it at the end of three years that you said, okay, I think I want to come back to Maine. 

Chris DiMillo: So my father, uh, you know, I enjoyed working my family's business. Growing up I was a waiter and a bartender and [00:04:00] really did everything busboy. And I started working there at a, at a very young age.

I enjoyed it, but I, I knew that the restaurant business was not my career. Um, my father owned a marina on the property, and, um, he always leased it out to a, um, a, a outside vendor. And that lease was coming due. And, uh, he wanted me to come home. He asked me if I wanted to, um, run it for him, and I said, well, I'll run it under a lease agreement, because I loved my father, but he was a tyrant and I didn't wanna work for him.

Uh, so I, so we, we agreed. 

Elise Kiely: Did he agree to that? 

Chris DiMillo: He did, yeah. 

Elise Kiely: So, uh, did that take 

convincing or 

was he looking forward to 

Chris DiMillo: He was looking forward to, to having me back and it didn't take a lot of con convincing and, uh, and we, you know, came to terms right away and. So I came back and started it. 

Elise Kiely: And so I love that story because I can appreciate a father's love wanting his son to come back and family to be together.

And he had purchased the [00:05:00] marina a few years before that, I think, or many, many years. Years before that. Several years. 

Chris DiMillo: Yeah. So he purchased it in 1979, and that was probably 1994. 95. Yeah. 

Elise Kiely: And had you, you, your only career had been in pharmaceutical sales as an adult. You had obviously worked That's right.

Dockhand, and you were familiar with boats and all those things. 

Chris DiMillo: And he had boats, so I understood boats 

and, 

Elise Kiely: but did you have any understanding of the workings of a marina at the time or did you learn as you went? 

Chris DiMillo: I learned as I went. And, um, I'm not afraid of taking on new challenges and uh, and he was there and my family was around and I was familiar with the property, so I, I knew I had people to lean on if I had.

Elise Kiely: And was he involved with, with the business with you? Would you seek advice from him? 

Chris DiMillo: More than I would choose.

Elise Kiely: And you still, you still, um, run the marina now? 

Chris DiMillo: That's correct. 

My, uh, I still, it, it's in my, um, realm of business. I have a nephew, um, Luke, [00:06:00] um, who really runs it for me. 

Elise Kiely: Oh, that's fantastic. Mm-hmm. So it's still in the, still in the, and that and how many slips do you have? 

Chris DiMillo: Uh, 120 slips. 

Elise Kiely: 120 slips with a range of boat size 

from 

Chris DiMillo: 17 to when the, the biggest boat we can accommodate is, uh, 200.

I think last year we had a 240 foot Wow. Vessel. Yeah. So, and we can ha we can, the marina's set up, we can accommodate eight boats under, over a hundred feet at a time. So we do quite a brisk, um, transient yacht, uh, business. 

Business. 

Elise Kiely: And you have some that are rent their slips or lease their slips year round.

And then you've preserved some for day or weekly rentals. That's, 

yeah. 

Chris DiMillo: And we also, when people that are there, leave. Uh, for a trip we rerent their slip. 

Oh, you okay. You re-rent their slip on a daily basis. On daily basis or something like that. Daily. 

Elise Kiely: And have you, um, have you noticed a change in the demand for slips or has it been pretty consistent in the last 20, 30 [00:07:00] years?

Chris DiMillo: It, it's been, I would say it's been incrementally increasing. Um, but what has, uh, increased so the demand for a slip is increasing a little bit, but the size of the boat is increasing exponentially. 

Elise Kiely: That's interesting. And to what do you attribute that, 

Chris DiMillo: um, wealth? Yeah. You know, just there's more money and more money and, uh, and people using the money for, for their enjoyment.

Elise Kiely: And I've, I've heard this adage that with certain 

business people, that if they have a 50 foot boat. And their colleague friend who's in a competing business or a similar business has a 52 foot foot boat. Well then they need to get a 54 foot boat. Do you, do you see that? 

Chris DiMillo: So it may be competition, it may just be that they go on the 52 foot boat and see that the two feet brings a whole lot more interesting, uh, accommodations [00:08:00] that appeal to them.

So 

Elise Kiely: that's fantastic. And it's a thriving business now. It's so desirable. You all do a great job on, on service. And, and you sell, you have a, the yacht brokerage business now to compliment the marina itself. 

Chris DiMillo: That's correct. 

Elise Kiely: And when did you start the yacht brokerage? 

Chris DiMillo: About two years into owning the marina or running the marina I, uh, saw the, the opportunity. There wasn't a, a brokerage in Portland, so I started it myself. And um, uh, and then I was fortunate enough, a few years down the road to be able to, uh. Uh, sign up as a dealer for Sabre Yachts, which are built in Raymond Maine, world class builder. Um, 

Elise Kiely: And that's your prof, that, that's your signature line that you all represent?

Chris DiMillo: Yeah, that's, that, that, yeah. My yacht sales business was, was built on savory yachts. Sabre, 

Elise Kiely: Do you own a Sabre yacht? 

Chris DiMillo: Uh, I have before. A few. A few, yes. 

Elise Kiely: How many boats do you own now, Chris? Uh, 

I

Chris DiMillo: just don't, well, personally, I just own one boat, you know, I own other boats that I have for sale. But 

Elise Kiely: Chris, let's turn now 'because I'm so excited to talk about the story [00:09:00] about your father.

Mm-hmm. Um, and how he, his story and how he grew up on Munjoy Hill and went from his experience as a young child leaving school pretty early working, and then creating what I is not an understatement to call an empire. Do, do you mind sharing that story? 

Chris DiMillo: Sure. No, not at all. My, uh, uh, father is a first generation, um, immigrant.

His parents were both, um, born in Italy and moved over here. Um. They came through, I think they came through, uh, some sort of immigration port in Canada. Um, but anyways, they end up here along with a lot of other, um, Italians from the same Abruzzo, I believe, region in Italy and settled all around, uh, Munjoy Hill and, uh, the East End.

Um, his parents owned a grocery store and he needed to work to help support his family. He, he came from a family of six and, [00:10:00] um, so he, and school wasn't his thing. So he, uh, ended his, uh, education at seventh grade and just went right into the, into the workforce. 

Elise Kiely: And in seventh grade, you're about 12. 

Chris DiMillo: Okay.

Elise Kiely: Around that. So at 12 years old, I'm trying to think where I was, or my children were at 12 years old leaving school and entering the entering work. Did he work for the grocery store? Did he work? 

Chris DiMillo: I, you know, I, I, I should know that and I don't know that, but I, but I, he worked in the, in the neighborhood is what I know.

Yeah. 

Elise Kiely: And he worked for, to help support the 

family? 

Chris DiMillo: That's correct. Yeah. 

Elise Kiely: Was he the oldest? 

Chris DiMillo: He was not the oldest, no. I think he was the, um, second from the youngest. 

Elise Kiely: And so time goes on and he's continuing to work and started to work in the restaurant business, I believe. Yeah. 

Chris DiMillo: So he, he actually went into the military and he served in the Korean War and along the way had met my mother who grew up, um, on uh, Cumberland Avenue.

Mm-hmm. 

High school sweethearts. So he went to the military, came back, they immediately, and she was a, [00:11:00] um, her mother was an immigrant from Canada. Okay. So she was born in Canada and, and moved here. And, um, they, uh, eloped in North Carolina and then immediately started a family. And he either started out with a restaurant or started out with a grocery store of his own, one or the other.

Elise Kiely: Here in Maine. 

Chris DiMillo: Yeah. And also right around this, right around Munjoy Hill. Oh, okay. And, um, and then slowly evolved the size of his operation, um, into the re the, the, the current restaurant. In the previous restaurant, which he had, he had that one for almost 20 years. 

Elise Kiely: So that the food was always a central part of the business of the family.

Chris DiMillo: And he loved food and he loved, he was an amazing, he was an amazing, um, cook and, you know, a larger than life personality. So hospitality suited him. 

Elise Kiely: And did he have a a, a mission with regard to his restaurants. Did, was there a certain vision that he had, customer centric [00:12:00] or, uh, an experience that he wanted to make sure his clients had?

Chris DiMillo: Yeah, I, I, I think it evolved over time. His first restaurant, which was on Commercial Street, it's where, um, right now there's uh, uh, sea bags there, Uhhuh. And, um, so that's where his first restaurant was. It was quite sizable and he really wanted to cater to, um, business clientele during the day and at night he wanted a little bit more formal, a little bit more sophisticated, he would have live entertainment. Um, 

Elise Kiely: and was this in the seventies? 

Chris DiMillo: This was in, I I opened in 65 and went until, um. Yeah, about 1980. 

Elise Kiely: So did you work there?

Chris DiMillo: I did, yeah. I was, uh, after high 

school and after school and stuff. Well, at that time I was young, so I, I worked there when I was probably 8, 9, 10 years old as a Really, as a water boy.

Yeah. And all my family did. I wasn't unique there. Yeah. 

Elise Kiely: Wow. That's amazing. 

Chris DiMillo: I was a slave labor 

Elise Kiely: and he was, and he was always there at the restaurant. 

Chris DiMillo: He was always there. 

Elise Kiely: Was he the chef? [00:13:00] 

Chris DiMillo: No, he was the front of the house. House. He was the man of the people. 

Elise Kiely: Yes. And I bet he loved entertaining people 

Chris DiMillo: and he loved it.

Yeah. 

Elise Kiely: That's, that's wonderful. 

Chris DiMillo: So he wanted the experience, of course, the food and, you know, he was Italian and Italian food was in his blood. But, um, the experience was what was, 

Elise Kiely: and then he moved that restaurant to what, Four street? I think, 

Chris DiMillo: uh, Four Street was before this one. 

Elise Kiely: Oh, okay. And then, and then commercial.

Yeah. Got 

you. And then tell us, te tell us how it, the DiMillo's restaurant came to be. I, I remember reading newspaper articles about this. Yeah. 

Chris DiMillo: So. He had this very busy restaurant on, on Commercial Street, the one I just referenced. And, uh, and even, even then, parking was an issue. So there was this vacant lot across the street and across the street and down, and he actually had a valet.

So we'd run a valet and the valet people would go park it in the car. And that property was owned by Canal Bank. Mm-hmm. And, um, Canal Bank occupied the brick structure that's [00:14:00] on the corner of the property. Um, and he wanted to buy it and he put it a, uh, a deal together to buy it. And he paid. And I wanna say that was probably made the acquisition.

It was late seventies, 77, 70, something like that. And uh, so he bought the whole property, including the bank, building the waterfront, everything for $650,000. 

Elise Kiely: Wow. Wow. And he obviously financed that, I'm assuming. 

Chris DiMillo: So he financed it. And I believe Canal Bank, who was his bank of choice, um, did the financing. He, um, financed it as, but the point of his purchasing that property was as a parking lot for his restaurant across the street.

And you know, who would know? Uh, what was to come next. 

Elise Kiely: That's, it's extraordinary. Yeah. And what probably the most valuable real estate in the city of Portland or in the, in the,

Chris DiMillo: it should be the most valuable, should, but we, we can get into city zoning and regulations and all that and, and another time.

Elise Kiely: Well, and we may get to some of that at the end, because I think I'm, I'm really interested [00:15:00] to hear you, your vision for Portland and the waterfront, because you obviously have a unique perspective of that. And so then tell us how the, you know, he bought the boat. 

Chris DiMillo: So he, as he says, he awoken a dream of, uh, woke from a dream with the idea of acquiring some sort of, um, ferry, barge, something floating and putting a restaurant on it because it was unused space. My father was very practical and he was very, you know, why would he wanna take away the space in the parking lot? He was, that people were paying to park in by putting a building there, so why not use the unused space? And, and at the time the marina wasn't there.

Elise Kiely: Right. So he was, and, and 

what was there, I mean, it was really working waterfront, 

was it? 

Chris DiMillo: So the, the original use of that pier was, uh, a coal wharf. It was called, it was, uh, the Pocahontas Coal Company, Uhhuh. And um, so that went away. And then it was really just some commercial fishing boats and that type of thing, commercial activity in there.

And slowly he built out the marina. Mm-hmm. Um, so how did he get the ferry boat? [00:16:00] Uh, so there's the, used to be a yellow newspaper called, um, boats and Harbors. And it just has all kinds of random boats and marine equipment and ships and commercial stuff and whatever. And he saw it in there for sale. And, uh, and it was, um, uh, the, the, the ferry was actually the ferry between Jamestown and Newport before.

Mm-hmm. The, um, the bridge, Newport Bridge was there. Um, and so he acquired it, I wanna say he didn't pay a whole lot for it, which was sort of his MO in life, not paying for a lot, for a lot of things. Um, and he had it towed up, so then he had to refit it. And it was, uh, 

Elise Kiely: were you, were you part of the refitting crew?

Chris DiMillo: It was, I was not, but if I had any talent, I would've been, he would've demanded that. Um, so he, um, needed to finance the refit uhhuh of this vessel, and he got turned down by the Bank Canal Bank, the people that mm-hmm. Sold them the [00:17:00] property and just thought it was a crazy idea. So he, um. came up with his own, um, financing, uh, plan, and he started a, uh, something called the Plank Owners Club, and he found 200 people in town.

And this is in the late seventies. Mm-hmm. So they each gave him a thousand dollars and in return they got $1,200 in, in credit for food and beverages and priority seating. And that Plank Owners club is still in existence today. It's still the 200, same 200 and something people, and they're on a plaque on the wall in there.

And now they still, you know, the ones that are still, uh, living, uh, still get the priority seating and they've all used their credit. 

Elise Kiely: Okay. I've done some research before we sat down. I didn't hear that story, but I love that. How creative. 

Chris DiMillo: Yeah. So, you know, he came up with whatever the number was, $250,260,000, and he was able to take that to.

The bank and the bank let that be his equity and they end up financing the rest of the project. Wow. [00:18:00] 

Elise Kiely: Yeah. because I do remember when I first moved to Maine seeing some stories about how DiMillos came to be, and there were some people who thought this was not a good idea Yeah. And did not think this was going to succeed.

But your father must have been very confident and trusted his instincts. Right. That this was a, going to be a successful venture. 

Chris DiMillo: Yeah. And, and he had the clientele, um, he had the, he had the people that he knew would be there to support 'em and mm-hmm. Um, and he, uh. He was a hard worker. Yeah. So he just knew if there was a problem, he would just keep working hard and figure it out and he would solve 

it.

Elise Kiely: And so he probably closed the other restaurant and then, yeah. 

Chris DiMillo: So it was a, it was a couple day operation because he would never have much downtime. Mm-hmm. So, you know, we're gonna efficiently close this one and opened this one within days. Wow. And then he ran the restaurant. He ran the restaurant along with the, and this time my, a few of my brothers were getting to the age where they could participate in the, in the actual operations.

Not just, or management of the operations. Not just the operations. Operations. Yeah. 

Elise Kiely: And did your father ever retire? [00:19:00] 

Chris DiMillo: Uh, not really. Um, no. 'cause he had such a passion for it, right? Yeah. I would say he worked less mm-hmm. And held less responsibilities. But, you know, right up until the, um, the end of his life, until he passed, he wanted to be in there and, and sit at the bar with his friends that had been coming in forever and have lunch with them, them, and go through the kitchen and measure the amount of french fries that were going on the plate and making sure nobody was throwing away the butter. 

Elise Kiely: And that's, you know, I think that's such a great story, Chris. And, um, that's like a made for TV movie, right? Yeah, it, it really is. I'm not sure who would play your father. 

Chris DiMillo: Yeah. 

Be Al De Niro, Robert De Niro, Pacino someone.

Elise Kiely: Yeah. Someone like that. 

Chris DiMillo: I, I forgot my father was very, was, uh, very dramatic. And, uh, I, I love this story that after he was denied by the bank and he got the commitments from all of these people and these checks, he went into the, to the bank and he, with a list of high profile people in [00:20:00] Portland, um, and said.

Yeah, you wouldn't believe in me, but this guy believed in me and put his check down. You wouldn't believe in me, but this guy believed in me, put his check down and he did that a lot, a lot. Embarrassed the people and shamed them into loaning him the money. 

Elise Kiely: But he got what he wanted. 

Chris DiMillo: He got what he wanted.

He usually did. 

Elise Kiely: That's, that's amazing. Do you think back and at, at that time, was there pressure for you to not go in to try to go into medicine but just come into the family business? Or was he supportive of your 

Chris DiMillo: He was supportive of whatever I wanted to tell to do. Yeah. Which is funny because he forced my older brothers into being in the family business, the business, whether you're the youngest, but I have a different life than they did.

You know? 

Elise Kiely: The youngest usually does. Yeah. 

Without a doubt. Do you, do you look back on your father who must have been a man, you know, larger than life? Yeah, 

yeah. 

Of, of 

Chris DiMillo: small man. 

Larger than life. 

Life 

Elise Kiely: of, of his philosophy of his business philosophy and his work ethic. And do you, do you think back [00:21:00] on that when you're running your own business now?

Chris DiMillo: Oh, absolutely. All the time. 

Elise Kiely: And wonder, what would my father say about this decision I've gotta make, or 

Chris DiMillo: every day. 

Elise Kiely: Really? Mm-hmm. Every day. Mm-hmm. And do you think your siblings feel the same 

Chris DiMillo: every day? And sometimes we can take, we can't, he, he was right a majority of the time, but he had a different way of doing things and sometimes we can look back and say, yeah, that was a little a little over the top, a little excessive, a little much, but behind it all was, um, really a, a sound foundation. 

Elise Kiely: Yeah. That, that's, it's very impressive. Yeah. And was your mother as involved in the restaurant too? 

Chris DiMillo: Well, she was, uh, 

Elise Kiely: she was raising eight children. 

Chris DiMillo: She was raising nine children. Oh, nine children.

Elise Kiely: Right. You're the ninth. 

Chris DiMillo: And, um, I, uh, I always say of my upbringing that I had everything I needed, but nothing more. And, um, but I mean, we ate as a family breakfast every single day. We ate as a family, um, not my father, because he was sleeping. Um, we ate as a [00:22:00] family every night for dinner. And you were expected to do that, and it just, you weren't, weren't allowed to not do that.

And my mother made a full meal for breakfast. Mm-hmm. Full meal for dinner for nine children, cleaned the house. I wanna say even for most of the time, she cleaned my room, you know. Wow. So, so she really kept busy doing that, and there was no time. Yeah. And then as, uh, as we got older and the restaurant moved into the, um, onto the boat.

She started working there at the front desk and, and she did that for many years during the day. 

Elise Kiely: It doesn't sound like anyone in your family was a slacker. 

Chris DiMillo: No. 

Elise Kiely: That probably, that word didn't come up. 

Chris DiMillo: Wasn't, that wasn't, that wasn't, that was frowned upon. 

Elise Kiely: I, I can imagine frowned upon is probably one way to say it.

What, was your father interested in boats? Was he out on the water a lot? 

Chris DiMillo: He liked boats a lot. 

Elise Kiely: He did? Okay. So that he, but did he have a 

boat? Did you all go? 

Chris DiMillo: He had several boats. Um, he would buy older boats. Um, and he liked to entertain on 

boats. 

Mm-hmm. 

So, 

Elise Kiely: so, so that didn't surprise you? There was, there was some [00:23:00] familiarity and Yeah.

Knowledge about boats and everything. Yeah. 

Chris DiMillo: He wanted to go around Casco Bay and see everything. My, my, uh, uh, brother Steven and I laugh because he, he wasn't a great navigator. He also wasn't a great boat handler around the dock. And we laugh because, you know, when you're, you. I mean, now you have a chart plotter that tells you everything.

Mm-hmm. And you know, it's amazing the technology today, but before I used to have a paper chart and whatever his paper chart was actually the place map from the galley restaurant in, um, in Falmouth. And that's how he navigated around Casco Bank, what was his, which is why he got in a little bit of trouble from time to time.

Elise Kiely: He didn't wanna spend the money on a updated chart. He wanted, 

Chris DiMillo: why, why would you need that retro? It's already here. 

Elise Kiely: It's already here. And so when he bought the marina, was, were there any of your other siblings who were interested in maybe managing the marina or running that part of it?

Chris DiMillo: Not really. And I'm not sure why.

I think it was, uh, he needed them inside the restaurant doing those things. And, and that was, that was really his focus. The restaurant. It was all about the restaurant, keep the restaurant going as it should and everything else will fall into [00:24:00] place. 

Elise Kiely: Wow. And was he ever tempted to sell off part of what is now probably the biggest surface parking lot in Portland?

Chris DiMillo: He was tempted and he actually did. So funny. because we've talked about Chandler's Wharf. So Chandler's Wharf was developed in the mid eighties. Eighties, yeah. Early eighties, something like that. And the developer of Chandler Wharf. And my father put a deal together for my father to sell the air rights over his parking lot.

I want to say the number was something like $10 million back then, I don't even know. Mm-hmm. So maybe 5 million, whatever the number is. Um, and then because of the uproar over Chandler's Wharf going there, the city council ended up enacting a retroactive moratorium for any residential development on the waterfront.

And, and so the project never happened. 

Elise Kiely: So there was, there was a deal to build, there was a deal over the 

parking lot, 

Chris DiMillo: it was deposit. And my father ended up with the deposit at the end of this. 

Elise Kiely: Wow. Not surprised. Not surprised at all. And, and has the family [00:25:00] always been consistent in keeping the property intact?

Yeah. Yes. Because the value of it Intact is, is just, is so high. And how many parking spaces do you have there? I should know that number. 

Chris DiMillo: I want to say it's, uh, 260. 

Elise Kiely: It's a lot. Mm-hmm. It's, it's a, it's a whole lot. Um, and it's such a prime location.

Let's, let's turn the page a little bit, Chris, and let's talk about your business and how you run your business, both the Marina and the yacht brokerage, which are two separate businesses.

Mm-hmm. Obviously, um, symbiotic, um, my, my impression of how you run the business just from knowing you from real estate and, and your reputation is that you are very intentional about your business and have a very specific culture, um, that you apply to, to your business. Could you talk a little bit about that?

Sure. I think that growing up, seeing my father, hospitality has always been, it, it sort of runs in me. Mm-hmm. And I enjoy it. Mm-hmm. I enjoy people, I enjoy meeting people. I enjoy getting great service and [00:26:00] I enjoy giving great service. And, um, it. And that's sort of the culture that, that we have formed in my company.

And I have, uh, been lucky to found amazing people that work for me. 

And how many people work for you? Uh, about 

70. 70 

between the two businesses. 

Yeah. And, you know, that's including my locations in New York and Maryland as well. Right? 

Yeah, we, we wanna talk about that in a minute, how you've expanded because you're not just in Portland, Maine.

I'm just not in Portland. No. So you have about 70 employees. Wow. I didn't realize it was that big. And, um, and 

many, many, many over 10 years. Many over 15 years. Several 20 years. And it just changes, I dunno if it changes, but it really, uh, having that longevity mm-hmm. With all these staff. They're able to continue the culture that we created together and show all the new people what we do.

Mm-hmm. And how we're supposed to do it. 

And is that hard to create a [00:27:00] common culture when you have multiple locations up and down the East coast? 

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

Mm-hmm. Just every day 

because you have grown that your yacht brokerage is, I wanna say over 50 million. Yeah. Oh yeah. Annual sales. Yeah. Maybe it's higher than that at this point. Higher than that, yeah. Um, and how many boats a year do you sell roughly? 

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

So it's Right. It fluctuates and it's cyclical. And, and honestly, other people would, um, people don't understand this, but I don't, of course I wanna grow every year. But I'm not focused on that. Mm-hmm. I'm, um, because of the cyclical nature of it, I'm focused on keeping our customers serviced happy. Mm-hmm.

Keeping the [00:28:00] staff happy and. And 

hopefully make a profit. Right. It's a customer experience. Yeah. And and the employee experience. Yeah. Equally as important. Equally 

as important, yeah. 

Yeah. Because in order to acquire and retain talent, you have to have, make sure that they have a good experience as well. I remembered you won't remember this, but I remember when you were talking, I think you were talking to somebody else about, um, 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, do you all service any of the boats? Oh, yeah. Yeah. A big service department. And it, 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 at all different levels, um, throughout your company, in front of the other employees.

Yeah. We, you know, at, at our, um, annual party, [00:29:00] sometimes semi-annual. We, um, hand out, um, we wanna recognize people, but we also, you get to five years, you get, uh, two tickets to somewhere. You get to 10 years, you get two tickets in a week's day, and it's just as you go up, there's more, um, reward, but also just the recognition and, and, and them feeling my appreciation and my other managers their appreciation for what they do.

Yeah. I, 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, it's, I bet, you know, but I, but I try to return the favor. 

Did your father ever give you two tickets to somewhere for five years? No. No. No. 

Although he was very, he was very generous.

I, uh, as I said, I had everything I needed and he took me to Florida once a year growing up, and, um, and as, as he got on in life and he ended up, uh, in, uh, Florida. Uh, for [00:30:00] 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. He wanted his family around him.

He did. Yeah. 

Yeah. That's, that's sometimes 

that's, 

that's 

wonderful. 

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

quiet, just 

my mother. 

Where, where in Florida did they go? Uh, they 

were between Fort Lauderdale and 

Pompano Beach. Oh, okay. Oh, that's right around where I go.

Um, so let's talk about how you scaled your business. I mean, you, 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. Yeah. You'd done sales. Yeah. Um, for pharmaceuticals. How did you start growing this?

What were the, what were the skills or resources that you relied upon to? 

Uh, I, I'm an observer. I, uh, I like to watch what other people are doing, and I like to listen. Mm-hmm. I try to, you wouldn't know it in this podcast, but I try to, uh, listen more than I talk. So that's really, I'm just not afraid to, to try things and start things.

Yeah. And, um. And I can always [00:31:00] modify them and, you know, never sort of 

What was the first boat you sold? 

I, uh, sold a 36 foot tierra, 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, um, in the Great Lakes and, uh, 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. 

And, um, a big deal. You must have been thrilled. That's a big deal. That's a big deal. 

That's a big deal. Yeah. Good for you. Good for you. And then it just grew and grew. And you hired brokers. And I hired brokers. And 

really what changed? Two things changed. Um, the business was, uh, my very close friend, um, mark, closest friend my whole life, best friend my whole life.

Um, he was an avid golfer and he played golf at Family Country Club with, um, Bentley Collins, who was the marketing manager at Sabre Yacht. And they ended up on a, on a foursome one time and started chatting about boats and [00:32:00] 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, uh, so we ended up meeting and took a few more meetings and eventually I, uh, I was able to sign up on that and that, that's really changed the trajectory of, of my, uh, business, 

which shows that it's, it stems from relationships, relationships. Your reputation is a hard worker. Mm-hmm. A problem solver. So that your buddy Mark, even though he is your buddy, he knew that he wouldn't be embarrassed to recommend.

Exactly. Exactly. So that was really a 

significant 

turning 

point for Yeah. So that, that's one. And then the other is that I, uh, like to say that the, um, service in the boat industry is so bad that my very mediocre service seems amazing to people. So, so just. Just trying to do the right thing all the time and, and really, you know, just going the, the extra mile to, to keep 

a customer boating, keep them happy, happy.

[00:33:00] You know, 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. Mm-hmm. I do. And you like, because of that, you like to give, or maybe not because of it, but be, but you also like to give good service.

I get you find that rewarding much 

Chris DiMillo: joy out of giving good services as I, as I do getting good service. 

Elise Kiely: And I, I, 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. Mm-hmm. And that means doing things that they have no, that they don't even see, they're not even aware of.

Right. And it even could be what time of day is the showing or, um, 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 and, 

Chris DiMillo: and the art of that, which you are very good at, is making them feel like this is just [00:34:00] 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 outta 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 wanna 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. 

Chris DiMillo: And when things are going wrong, the ability to, um, to mask that a little bit. If they don't need to know, sometimes they need to know.

Right. But if they don't need to know, you know, you absorb the problem and, and keep delivering the experience and. 

Elise Kiely: That's right. You're good 

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

Elise Kiely: 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.

[00:35:00] He thought of the law firm, like a box, a black box client asks the question, there's lots of stuff going on in the box mm-hmm. That nobody needs to see. And then an answer comes out. They just wanna 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. Um, so I, I, I think that's a wonderful, wonderful attribute. And so you scaled the business here in Portland. Mm-hmm. And then when did you decide to expand beyond Portland? 

Chris DiMillo: Well, I, I would say that, uh, that I always had the, um, desire to do it and, uh, in, I was looking for the opportunities.

So 2006. That saber and, and saber's sort of sister company back cos, which is built in Rockland, owned by the same families, different plants, different mm-hmm. Engineering, different, different product lines. But some synergy came available down in, um, in, on Long Island. [00:36:00] And I was lucky enough to be the first in line to get it.

And um, I went down there and um, 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 wanna do it anymore. Mm-hmm. And, um, uh, he, uh. So we put a deal together. So I, I, uh, became the, the dealer for Saber and back Hove on Long Island. So that was sort of the next step.

Elise Kiely: That's, it's not easy to get from Portland to Long Island? No, 

Chris DiMillo: no, 

Elise Kiely: no. But that 

Chris DiMillo: was okay. That was okay. Yeah. I like to travel. Yeah, I like the, yeah, and I would, 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, driving, I'd say I'll never drive again.

Elise Kiely: Should have taken a boat, I guess. 

Chris DiMillo: So that has all its own problems, 

Elise Kiely: so. And how big was that Marina? 

Chris DiMillo: Um, so, oh, that's just a brokerage. Yeah. That there, I just have a brokerage in a service department. So I have, uh, three brokers. Um, an admin [00:37:00] person? No, two admin people. Service managers. So probably 10 people working there.

Yeah. Yeah. 

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

Chris DiMillo: Yeah. So then I, you know, I, uh. I try to keep doing what I know, you 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, you know? Mm-hmm. Turns out I'm a one trick pony selling these savers and backhoes, but I'm very good at it.

Um, and so this is just a little bit of a funny story about, about Delos. I met 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 Dami shirt. This guy gets on the boat and he looks at my shirt and he says, oh, Dili's, he's this great restaurant.

I, I keep my boat up in Maine from time to time. And I, I go into the restaurant and, uh, he said, it's great. And I said, oh, very nice. And so I struck up, you know, a little bit of a dialogue with [00:38:00] him and of course find out he's a serial boat buyer. And, uh, so we get to be, you know, a little friendlier and, and the one year later, 'cause people don't buy million dollar things on a whim.

Mm-hmm. 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. Were you still 

Elise Kiely: wearing the Mila shirt? Of course, 

Chris DiMillo: of course. Fresno not wearing it right now. Um, then. He had a great experience with my people up in Maine.

'cause he took delivery up in Maine. He want to use the boat, but I, Maine. Mm-hmm. And he, he believed in me, believed in the, in the Sabre product. And he said, I want to buy the Sabre dealership in Maryland. And, uh, so I said, all right, I'm in. And he was a, a wealthy guy. Mm-hmm. And um, he was able to just do it without [00:39:00] financing and without me.

Except he wanted, you know, he had the finances, I had the knowledge and the experience. So he ended up buying the dealership. We became partners and uh, I bought him out a few years after. But, you know, I just always think about that as the, how the brand that my father 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, the in Maryland Eastern Shore, Maryland location. Yeah. So I'm 

Chris DiMillo: on the eastern shore of Maryland and, and also the, 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 

Elise Kiely: Bridge.

Chris DiMillo: That's right. 

Elise Kiely: Yeah. That's, oh, that's fantastic. All from the brand and is a great client 

Chris DiMillo: and a great friend. And he, uh, he bought a vote last fall and, uh. He called me this spring and he's like, that's just not right. And then we started talking about the next, he's like, 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 [00:40:00] 

Elise Kiely: and a good friend now at this point too. 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, um, Kittery? I think, uh, 

Chris DiMillo: uh, I was in Kittery, so we're just in Kenne bunk port now, in, in, uh, stay tuned.

There's more, there's more to come. There's, there's more 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. Uh, modification, expansion of, of the business 

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

Elise Kiely: and you know, my sense is in, in the, in the yacht brokerage and marina business, that there's been some consolidation.

Mm-hmm. Um, because it's, the barriers to entry can be pretty high. Mm-hmm. 

Chris DiMillo: And, 

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

Chris DiMillo: I, I, um, [00:41:00] it, it's not my soul reason for not pursuing, being, being acquired or, mm-hmm.

But my son wants to be in the business. He, he now works in the marina in the summer while he's at school. And he's college age right now. Yeah. He's college age. Yeah. So goes to school in Florida in the, in the, during the year and comes back and works in the summer. My nephew runs the marina. Mm-hmm. And also I just, I have amazing people that work for me and I would have a difficult time not knowing what the next thing is for them.

Elise Kiely: Yeah. You feel protective? Yeah, I 

Chris DiMillo: do. 

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

Chris DiMillo: I do. I, I, frankly, I'm a little over it now, but I've been doing it long enough that, um, I'm, I'm more interested in, you know, I thrived on transactions. Mm-hmm. And, and, and finding a client and finding them the boat and closing the deal, and I thrived on it.

Not so much anymore. [00:42:00] Yeah. But I have 12 salespeople that do that, and, and they're thriving on it now. So I have a little more interest in, in bigger picture stuff and strategy. More strategy, yeah. And in real estate, and. Yeah, 

Elise Kiely: that's what expansion, that's why you and I are gonna keep talking, Chris. Okay.

It's all about the, all, all about the real estate. Um, let's talk about some stories. You deal with some really interesting people. We both do. Mm-hmm. In the, in the businesses that we have, you deal with a lot of very wealthy mm-hmm. Sophisticated, educated, um, people. And you can't sell the number of boats and the volume in sales that you do without there being some really crazy stories out there.

What's, if, if someone's gonna ask you at a cocktail party, what's the craziest experience you've had? What's one of those stories? 

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

Elise Kiely: Perfect. 

Chris DiMillo: That, um, yesterday we got a call, and this is, I'm laughing because nobody got hurt. Um, we got a call from someone who sold, we sold the boat [00:43:00] 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. Nobody 

Chris DiMillo: was staying on the boat. 

Elise Kiely: Not even the captain. No, nobody. 

Chris DiMillo: So everybody was safe. How that happen.

And of course he calls my salesperson and my salesperson is completely alarmed at, you know, 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. 

Elise Kiely: We could have it in Newport in two days. Yes, exactly. That's crazy. How did it burn? 

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

Elise Kiely: just happened. 

Chris DiMillo: Just happened. So it literally just happened yesterday. Wow. Oh, that's crazy.

And scary. And yeah. So, so, you know, you have the boat connected with a shore power cord to a, to a fitting on the dock. Right. The salt air, the loose [00:44:00] connection, the whatever, all all the things that add up to Right. An, an electrical fire. Right. So that's probably where it came from. 

Elise Kiely: Have you ever had, because you sell both new boats mm-hmm.

Through Sabre, and you do resales for people. Yeah. Um, 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 and the 

Elise Kiely: 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, um, I actually never had a seller decline to continue on in our purchase ever. And I've had many buyers there, but because no one needs a boat. And, uh, you know, the, 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.

You're not in charge of 

Elise Kiely: marketing if you say that. 

Chris DiMillo: Um, but the, the contracts we have are amazingly [00:45:00] buyer friendly and, you know, you get a long time to figure out whether you want to do it or not with, with no risk, you know? So, 

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

Chris DiMillo: Yeah. Yeah. And you, you have to act to bind the contract mm-hmm. If you don't act the contract just 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 given me a little run around in buying new boats. Mm-hmm. And, uh, generally I, someone doesn't wanna buy, someone doesn't wanna buy the thing I give them, I just let them out of it.

It's making somebody do something. That they don't want to do is never a good business decision. No. Or recipe for sleeping well at night. Right. Um, but there have been times where I've made them. 

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

Chris DiMillo: Oh, completely. And if 

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

Yeah. I got my ego got in the way. Help me out. That's gonna have one reaction. If [00:46:00] it's bluster and, and ber saddling Yeah. Then that, that might be a different response. 

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

Elise Kiely: Yeah. 

Chris DiMillo: Yeah. It has to from time to time. 

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

Mm-hmm. 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 Sabre. What's the, what's the biggest new constriction? 66. Feet. Yeah. That's a big boat. 

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

Mm-hmm. They just don't average. What's the average age? 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.

So they're not so customized that they're so unique. But recently we did have a boat, a boat in, um, [00:47:00] 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, that's what people do when it's their idea. They think it's the most amazing thing ever.

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

Elise Kiely: you know, if it's been tried and true.

Yeah, exactly. You wanna be pretty vanilla if you're going up. Same thing in a house. You don't wanna be so unusual that it's, it's, it's gonna make things difficult for the next buyer. That's interesting. Dog washing station when there's water all around you. Right. That's, that's fantastic. Um, Chris, let's talk a little bit now about COVID.

Mm-hmm. And what that, what happened during COVID? Do you remember? Back in March of 20? Yeah. [00:48:00] Yeah. How, what were you thinking in the very beginning? Um, 

Chris DiMillo: well. The first thing I was thinking was that I was probably amongst the first people in Maine with COVID. Really? Yeah. I, um, went, took my son and a couple of his friends skiing in Utah, and, uh, we arrived back on the 15th of March.

Elise Kiely: All right. Ground zero. Yeah. So 

Chris DiMillo: either the travel out there, the travel back, I don't know what You didn't feel good. 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, you know, symptoms. But I, you know, I guess we were living in denial and we didn't, what is it, are you supposed to social distance or, yeah.

And, you know, 

Elise Kiely: mask. You didn't take the preventative measures. Yeah. Yeah. And, 

Chris DiMillo: and, and really at that time it was, so it was at the, I mean, it was at the beginning. It was the very beginning. Beginning. 

Elise Kiely: We all thought this was gonna be two 

Chris DiMillo: weeks. Yeah. There were, there were zero recorded cases in [00:49:00] Maine, you know, because they would announce 'em on the news every night.

There was zero. Right. And this is when you were living 

Elise Kiely: in Portland, in the condo? 

Chris DiMillo: Yeah, yeah, yeah, yeah, yeah. Okay. And uh Oh, wow. Yeah. 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, 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 to be thanking me. That's right. Now you're immune. Now you're immune. And they all say, you're welcome. So anyways, we so work through that. But yeah, you know, I'm in the boat business.

Elise Kiely: It did, you know right away that boats were going to be one of the things that people would just gravitate to? No. 

Chris DiMillo: Because the, the local governments and were shutting down down marinas and Yeah. You know, so everything was shutting down. All my employees were staying home and, you know, I didn't know I was gonna get the [00:50:00] PPP money, but it was certainly gonna not stop paying them.

Right. Um, so I'm paying all these people to stay home and the boat business is cyclical as it is. You know, nine 11 was a, was a turmoil. 2008, 2009, the recession. Mm-hmm. That was a disaster. Mm-hmm. It's the first thing to go. And so Right. Discretionary purchases. Right. Yeah. And, um, and you 

Elise Kiely: probably had people living on their boats maybe.

Yeah. In the marina. Yep. Yeah. 

Chris DiMillo: So what we, what we just saw was that 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 gonna, there was no panic selling 

Elise Kiely: uhhuh, 

Chris DiMillo: which would've been changed the whole dynamic, you know? Right. And then, I dunno, within three months we could start to see that people were saying, okay, yeah, this is, this is something I can do.

Elise Kiely: Or not even. Okay. I mean, 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, yeah. But it was, 

Chris DiMillo: it was gradual. 

Elise Kiely: So it wasn't overnight. It 

Chris DiMillo: [00:51:00] wasn't overnight, it was gradual, you know? So, so from March to like the fall boat show season, that's when it really started to pick up.

Mm-hmm. And, and, but then the flip side of it is that the manufacturers, their capacity all went down. So there was a, there was a, um, a, uh, frenzy of, of buying in buyers, but the, but the supply wasn't there. Right. So that, that, 

Elise Kiely: so you have this 

Chris DiMillo: pent 

Elise Kiely: up demand with no supply. Yeah. Sort of like real estate. So we were doing, 

Chris DiMillo: we were doing a normal number of transactions.

We weren't doing more transactions, but. We were making more money on every transaction. 

Elise Kiely: Yeah. 

Chris DiMillo: Because people were paying more for, for the boats. Mm-hmm. If I had a new boat, we could, you know, we didn't have to negotiate when it, so, so 

Elise Kiely: it was a really robust time. It was, yeah, it 

Chris DiMillo: was. 

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

Were they older, younger, maybe a, maybe a little younger. Little younger? Yeah. Interesting. Yeah. Interesting. Yeah, it's such an, it [00:52:00] 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. Right. And so it, and that lasted a good two and a half, almost three years.

Yeah. Did it last that long in the boat? 

Chris DiMillo: Same. Same. Yeah. And I, uh, I believe we still have a lasting effect from it, that people have a greater sense of their own mortality and they are willing to spend money a little more freely. You know, 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. Mm-hmm. And, um, I've seen that loosen up a little bit because people want to, you know, I've seen, you know, the wealth transfer, right?

People are doing that before to their next generation doing it, before they [00:53:00] would've normally. Mm-hmm. 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, 

Elise Kiely: it is interesting to have the pandemic happen, right?

When this great wealth transfer Sure. Was about to take place and I, I see it in real estate too. I, I affectionately call them labs. Luxury active baby boomers. Yeah. And they all physically active. They want to be skiing, they want to be boating, they're playing tennis. They're, they, 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, some wealth and they are gifting it to adult children, significant cash so that they can be competitive in, in their, in their first house. Mm-hmm. And it's really interesting to see the per the, the effect of COVID and maybe, maybe that accelerated it a little bit.

I don't know, but it's, 

Chris DiMillo: I'm sure it did. I'm certain of it. 

Elise Kiely: Yeah. It's, [00:54:00] it's definite then. And are you seeing the high end a boat sales driving the market? In boat sales. Yeah. More than the entry or middle end. Mm-hmm. 

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

Mm-hmm. But now it's really the higher end, the high end. And what is the high end for a boat sale? Well, that's all relative, right? So my high end is, you know, above my high end is above 2 million. Mm-hmm. Um, but I would say our real sort of success spot is seven 50 to a 750,000 to a million and a half.

Mm-hmm. 

Elise Kiely: So that's your bread and butter. Yeah. And the above 2 million is the maybe 10% or something like that. Yeah, yeah, exactly. Yeah. 

Chris DiMillo: And, and uh, you know, just interesting too, the price of everything has changed due to all kinds of things. Mm-hmm. I don't know that tariffs have really affected. Pricing yet, but inflation price of labor, E everything, yeah.

Has, has changed. [00:55:00] 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 bucks. 

Elise Kiely: Wow. 

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

Elise Kiely: into voting.

Into 

Chris DiMillo: the family. 

Elise Kiely: Right. That's right. 'cause they, if the, if the entry price is too high, then you're gonna exclude. Right. And, and that will age out. Your current customers will age out. That's right. Yeah. That's very interesting. Um, Chris, let's shift a little bit. Let's talk about Portland's waterfront. Mm-hmm.

And how you've seen it change over the years, and where do you see it going with 

Chris DiMillo: the current 

Elise Kiely: vision? With the vision of the current, well, let's, let me back up. Let's try this. Yeah. If Krista Milow 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, and when I say maximize value, I don't mean just [00:56:00] for the DiMillo business enterprises. I mean, what is the highest and best use for Portland for the waterfront? 

Chris DiMillo: Um, certainly preserving the working waterfront is, is paramount to keeping Portland what it is. 

Mm-hmm. 

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.

Elise Kiely: Yeah. 

Chris DiMillo: Um, because there's just vacant land and vacant dock space on commercial wars doing nothing, run down buildings because you can't support the cost of the infrastructure. On what you can get with With the permitted uses. The permitted uses, yes. 

Elise Kiely: I feel your father would be so frustrated. Oh yeah. By all this, you know, potential.

I, 

Chris DiMillo: I, I would say that the, um, and it doesn't really matter to me or my family, um, because we're happy doing what I'm doing. My [00:57:00] 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 um, has been a great, produced a great return for us, but the current zoning has probably reduced the value of our property to buy probably 66%.

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

Elise Kiely: And I know your brother was very involved in, in a lot of, um, the counter to that of the referendum. Yeah. You know, and, and so you all ha do, I think, my perception is you all are stewards of Portland and you participate. Your brother didn't need to participate in that. It's not, I mean, no, I call 

Chris DiMillo: him the, the, the, uh, defacto mayor.

That's right. You know, um, he [00:58:00] knows everybody and he is all about Portland and he's right. And a big, big supporter. A big supporter and, and, and, and a, and a big, uh, giver of his time 

mm-hmm. 

That he doesn't need to do. Mm-hmm. Um, 

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

Mixed use? Mixed, yeah. 

Chris DiMillo: Mixed. Yeah. What's wrong with residential development on the waterfront? What, 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. 

Elise Kiely: Mm-hmm. 

Chris DiMillo: It's just that people just can't see past it and they just wanna say no.

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

Yeah. But, but that was a great experience. Um, and it allowed you to be able to walk to and from work, love it, and be [00:59:00] part of the community. Mm-hmm. Which I think you really enjoy being part of, uh, see and be seen type thing. 

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

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

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

Chris DiMillo: up on the peninsula. My parents didn't buy a house on the West end or the, you know, fancy house on the east end.

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

Mm-hmm. 

And I, uh. I think I, I just, 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 that haven't.

Mm-hmm. And that's just disappointing me. And I, you know, if we just talk about general, the Portland in general, this whole thing with, uh, the [01:00:00] 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 the development of the old port.

And he's just does great projects and they wanna take a vacant piece of property. And put something in it that'll drive more people to Portland. Mm-hmm. And all of a sudden, that's not what we want, anymore. Want. Well, it, look, all of the people that live here, work at restaurants, work at hotels, um, work in all of the, the, the ancillary business that support this.

Why don't we want more? Another reason for people to come here besides the restaurant. Mm-hmm. Traffic. Who cares? A little traffic will be just okay. People change is hard. Change. Change is hard. No, it's 

Elise Kiely: not. Change is hard. They think it's hard. It's not. They think it's hard. It's not. Well, it's the same thing with the resistance to the RU Institute.

Chris DiMillo: Yo. Exactly. 

Elise Kiely: I mean, what, what a wonderful thing. Amazing. For Portland. Yeah. And we're not gonna be Portland of the late 18 hundreds or 1930s or 1950s. Yeah. And nor should we be, and nor 

Chris DiMillo: should [01:01:00] we be and we shouldn't be at of you. You, you started with asking me about the change if you walked around the Portland waterfront in 1980, um, before, you know, my father sort of sparked what was going on down there.

Mm-hmm. It was awful. It was dirty. Which 

Elise Kiely: is, which is why it took courage for your father to do that. Absolutely. Because he had to have a vision. People 

Chris DiMillo: are not recognizing they, the, the courage of the people that took the risk to build what's there now. Right. Fighting an uphill battle at all times. And they just think that, that people who are, who are against every kind of development, just that they're taking advantage and they're, you know, whatever.

They're not. Yeah. 

Elise Kiely: Chris, this has been, I could talk to you for hours and I hope you come back. 'cause I would love after a few years, let's see where the Portland Waterfront is. Let's see where Dili's is. I think there's probably some news announcements I can tell from mm-hmm. Looking at your facial expression, there'll be some announcements.

I would love to have you back and share more of your insight. I'd be 

Chris DiMillo: [01:02:00] glad to come. 

Elise Kiely: Um, I always end with a few key signature questions mm-hmm. For people. Mm-hmm. So if you don't mind, I'll, I'll ask you please. Um, where do you find elegance in Maine? And by elegance I don't mean formal, stuffy. 

Chris DiMillo: Yeah, 

Elise Kiely: I mean, beauty, 

Chris DiMillo: um, I can find it in so many places.

I can find it going into, uh, scales, restaurant. I 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. Um, walking around the Eastern promenade, boating around the Eastern promenade, looking at just how magnificent that, uh, real estate is there and the history.

It's so, we're so lucky to live 

Elise Kiely: here. It's so lucky. It's so interesting. So lucky to live here in the summer. It's right. We're gonna get you back a little bit in the winter. Um, what's your favorite place in Maine? 

Chris DiMillo: Um, I just love Portland and I go to other places and I find them, um, charming. And I, you know, I skied for years at Sugarloaf and I'm just sort of past that, that chapter.

But that was an amazing experience for me and my family. [01:03:00] I, you know, I enjoyed that. I enjoyed the, I, it's just hard to say. Yeah, I really love Portland. Yeah. But I love the Midcoast, I love Bar Harbor. I love Chris 

Elise Kiely: 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: And seriously when you fly in to Portland and you, um, I forget the name of the route that it is, where you fly in, uh, to, uh, I think it's the harbor entrance or whatever, but, and you fly over and you see all the islands. I mean, it's, and then you come over and you're looking down over the old Portland waterfront.

It's beautiful. It's spectacular. 

Elise Kiely: Yeah. It's, it's so authentic. Um, favorite coffee shop. Um, 

Chris DiMillo: wow. I guess I'm kind of basic. I really like Dunking Donuts. There you 

Elise Kiely: go. That's perfect. I haven't heard that one yet. So that's Fanta. Is there one near you? Um, there's one at one city center there. You okay. That's perfect.

Um, what's the most influential, 

Chris DiMillo: and by the way, all of them in town owned by a local. Yes. Not, you know. Yeah. Doesn't mean it's, I'm supporting some [01:04:00] capitalist organization. Um, owned by a local. By a local, and employing great people that his people have been there forever. So. 

Elise Kiely: Anyway. Well said. Well said. Um, what's a, in a influential, I won't say the most 'cause 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, um, have read this a couple times and I thought it was, uh, really good at, called B 2.0. B 2.02 B 2.0. So you want to, you want to B right 2.0. Next thing like Krista 

Elise Kiely: Mil 2.0. Yes, exactly. Always. Trying to, you know, improve play up, improve.

Chris DiMillo: Yeah. Yeah. And, 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. Mm-hmm. And how, uh, the wrong people can really change quickly, [01:05:00] change a culture that is always doing the right thing and always has the right attitude.

So in the book they say, you also gotta know when to get the wrong people off the bus. 

Elise Kiely: Off 

Chris DiMillo: 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, you have to know the right people in the right seats mm-hmm. On the bus. So last question for you.

If your father was sitting here mm-hmm. What do you think he would say about you and your siblings and the stewardship of the businesses that you've developed and grown? 

Chris DiMillo: Um, I think he would be very proud. And I think it's really, you know, if he walked into the restaurant to 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 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 uh, so, but I think he would be very proud.

He [01:06:00] would have a hard time expressing it, but I would know it. 

Elise Kiely: You would know it. Yeah. Yeah. And that's, and that's all that matters. Yeah. I fibbed 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: So, I'm asked this quite a bit from young people that I just come across mm-hmm. That wanna be in the boat business mostly. And, uh, 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.

And he ingrained that into me as 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. Mm. So, and you were hesitant to scale. I was. I was hesitant to scale. Exactly. Yeah. [01:07:00] It's, 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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I am always happy to help in any way that I can, and we welcome you to come and explore Maine. Thank you for listening to Elegant Maine Living, where elegance isn't just an aesthetic, it's a way of life. Until next time, keep living with elegance.