Developers to Watch

Samantha Riccio | 6 Boston Developers to Watch in 2023

During the height of COVID, Samantha Riccio made the jump from a 9-5 into development, and has never looked back.

Name: Samantha Riccio

Company: Eagle Hill Homes

How did your journey into real estate development begin?

In 2017, my husband and I bought our first rental property and started renovating it ourselves because we were broke and really had never done it before and had no background in real estate. But we had wanted to purchase a rental property for quite some time and spent years saving.

I was working a normal W-2 job in marketing and we continued to house hack. Purchase a property, renovate it, live in it, refinance, and move on. So we did that three times, basically getting into these properties around Boston that we couldn’t afford if we didn’t purchase them owner-occupied.

That’s how my real estate career started — it was really the construction process I fell in love with. Didn’t know that was going to happen! We had never done construction before. I never had a background in it, but I really took to it. And lo and behold, here we are today.

How do you just learn construction while doing your own projects? YouTube? Talking to people you knew who had done it?

Yeah, so a lot of YouTube videos for sure. My father-in-law has been in construction his whole life. He had his own construction business at one point, but when we started, had went to the union and was working on huge projects like the casino.

He would come over after work when he got out at 3:00 and basically critique us and say things like, you’re doing it wrong, you’re doing it right. Essentially yell at us! Nick and I were just kind of winging it and he just helped so much. He was definitely my catalyst.

My husband and his dad have an awesome relationship, but now they joke that my relationship with him is the best of anyone in the family — because me and my father-in-law are like cats and dogs, but also two peas in a pod. He truly taught me a lot. And then from there, I naturally got it.

I gravitated toward it and I felt like I was understanding more than most, and it was easy, because next to Nick, I was saying, “Oh, that doesn’t click for you,” And he’d remind me like no, that’s not the norm. And so when I realized I had that, I thought, maybe there’s something here.

Were you surprised that you loved the construction side, or were there signs in your past that you would take to it?

There were definitely signs in the past. I always wanted to get my hands dirty and do those types of things. I would decide to repaint my bedroom when I was a kid just on a whim. I’d beg my mom to take me to Home Depot to get paint and I ripped up the carpet in my room when I was young, when my parents left the house, which was, you know, your typical 90s house. I cut it up with the scissors and too kit all out, because I was like, “Mom, there’s hardwood under here.” I was like 13.

So I feel like those moments were there, looking back. But then I never would’ve seen it.

You mentioned that you did your first project in 2017 and then repeated the process three times. At that point, did you still have your nine-to-five job?

Yep. At the conclusion of the third house was when the jump happened. But then COVID happened. The company I was working at, I was doing marketing, and I had switched a couple times post-college, but I liked what I was doing, liked my coworkers, but I wasn’t feeling like I could do that for the rest of my life.

Nick and I had talked a lot about what we would do moving forward, where real estate would take us, and we kept saying, “One of us has to leave our jobs,” because we wanted to really go head over heels into the investing.

Then I got laid off, a couple months before COVID hit. It was one of those things that the company wasn’t doing great, needed to make some cuts, but they wanted to keep me on for the next five months, because they needed help transitioning. Then COVID happened during that window, and they cut a huge part of the company, but I was still there, which was really strange. So I had time to think about, am I going to get a new job? Will this be the jump?

So after the layoff, we decided that whatever happens, this is the sign that we needed and I’m going to focus on real estate. Not even construction at this point. So we made that decision in like, February of 2020.

We had so many times where I was like, oh no — we didn’t know this would happen, I have to get a new job, we need the money, and so many conversations with Nick, being like, we can’t go back on our word. We said this was the sign. As scary as this is, no. We didn’t want to kick the can down the road.

So I didn’t get a new job, and I was pretty much jobless, figuring out how we were going to make real estate a career path at that point.

What was your mindset like at that point? That’s a big leap to make.

In a weird way, I was oddly calm. You would think I would’ve been more stressed. I was at peace with the decision because I had so many moments where it would’ve been easier to just apply for a job, get one, and move on, right? But I was at peace with the decision.

I was scared about the fact that I didn’t know what my future held. I’m very black and white. I love a plan. I’m not very spontaneous, even though this story is making it sound otherwise. So I was out of my comfort zone, but at that time, I was really just like, “Okay, how can I make this a career?”

And at that point, Nick was the one encouraging me to do construction and interior design. Because I would design all our spaces and that was what was really calling to me. So I started applying for a ton of internships, trying to find an internship at a construction company that would take me under their wing so I could get into real estate while still having some part-time income.

And then I was thinking, OK, if I could do that even part-time, if someone would take me, I could work on our investing and then start to do direct mail and reach out to different people and try to source some more deals so that we could continue to invest. So that was my goal.

I did that for probably six months until I realized that no one was going to hire me and I had to make it myself. That’s when the mental switch came. Nobody was going to give me a break, so I had this aha moment, like, let’s turn the tables here and create my own business.

That must’ve been empowering, but also a little scary.

Yeah. I knew no one was going to come in and save me. It happened at a weird turning point in time where I had started to think about getting my general contracting license, and my thought was, you know, I'm super passionate about it now. I have all this experience. Let's get this license. Let’s source a deal. We’ll do some type of development, or another rental property, and I’ll GC the job myself. That was the thought process. I started studying for the exam, and even before I announced publicly that I had gotten the GC license, I had someone reach out to me saying, “Hey, I know you guys do these renovations — could you help me renovate my kitchen and living room?” And I was like, no! Why would you want me to do that for you? [Laughter] Even in that time of desperation, my knee-jerk reaction was like, what if you hate it?

But after a little — or a lot — of convincing, I said I’d do it. So I went ahead and did that project, and that was the end of February, into March, of 2021. I learned a ton. There wasn’t even a functioning business at that point. It was me, myself, and I trying to figure it all out. It kind of just all spiraled from there.

I went on our little Instagram account that I would post our renovations to, and that’s how word got out. I would just pop on the phone and be like, “Hey, I’m doing a client project, I’m scared as shit.” I was so open about it. The project took 12 weeks. By the end of that project, we already had three others booked. It just started.

So you have three other jobs booked at this point. How do you juggle those? What was your process like?

So I'd like to say I had this incredible process built out. I think I was in shock that this was happening, and my main thing was like, I need to get a bigger sub contractor base I need to work on. The design was really the thing that I was super passionate about that. I wanted to incorporate that into the business, and not just be a typical GC.

My husband Nick was really the backend person. I'm starting to realize now more than ever how much he actually did during that time because I was like, heads down trying to like, get a contract signed and, say, pay a deposit to get the demo guy there. I didn’t have a good process to make me calm and happy — and I’m someone who loves a color coded book of anything. So it’s funny looking back, knowing that I was so overstimulated, having 17 things on my to-do list that needed to get done by the end of the day, and he was more like, “How do we streamline this?” So he did a lot of backend work figuring out the software that I still use to communicate with clients, subcontractors, do billing on — things that, if I didn’t have set up, the business probably wouldn’t flatlined after just a couple projects.

Did you and your husband always imagine getting into business together, or did it just happen organically? Not every couple could work together.

We always planned it. Our relationship started at a very young age. I met him when I was 14, and we never looked back. We’ve been together for a very long time and went through a lot of change together — you're going to high school and to college and getting a real job. We did all those steps together, and realized that we work very naturally together. We got engaged a couple days before we purchased our first rental property.

Throughout the process, we were planning and paying for this dream wedding. We were knocking down walls, living in debris, and it felt so easy. I think that was our moment of like, wow, this is going to work. At this time, too, Nick had a full-time W-2 job doing residential mortgages. So he was working an insane amount of hours, trying to build me up in this business, and we were also co-managing our properties that we had around the city, and then there was the construction business. So, crazy times, but definitely wouldn’t change it.

What tools do you use to stay organized?

Everything goes back to the fact that the business isn’t even two years old, and the processes we’ve implemented have liked, 10x’ed everything. The software we use is called Buildertrend. It’s client-facing and sub-facing. It’s great. I quickly learned in my first few projects what my biggest hurdles are. Number one was clients just calling whenever they wanted and venting about anything. Number two was meeting up with, like, a subcontractor in a parking lot on the side of the highway to give them a check. Number three was spending a lot of time to quote out jobs, very detailed, that we didn’t end up winning the bid. Buildertrend helps us with all of these things.

In the beginning, I was too worried to tell a sub, “Hey, if you don’t use this, you’re not going to work with me.” I was like, please do this job, or we won’t have a business! [Laughter] Now, I just say this is how we work, this is our system. And it’s easier and better for them, too, because they’re getting their money in an instant transfer.

What about the bidding process — what approach do you take there?

In terms of general systems and processes for bidding, we came up with a very different system than most GCs, I think, because we do both the design and build. So a lot of people will source an interior designer, have them design the space, help them with design plans, and then come to a general contractor with a full fledged design plan down to even paint colors and say, “Can you execute that for me?”

We really try to market ourselves as both. So if a client comes to us and says, “Hey, I want to do a full gut remodel on my single family,” I would come and do a initial consultation, essentially like a one-hour walkthrough, and then in two weeks turn around an initial budget, in a range. I don’t go to every single one of my subs and ask them because, I mean, I have enough historical data at this point to know generally what this project's going to cost them. So it doesn't take too much time on my end. And again, there's a range. We may say $300-$350k, for example.

This does not include any materials — your cabinets, your countertops, you're flooring, your tile. I don't know what you're gonna choose for that, but I wanna be involved in that process. The client can then sign an agreement which puts us into a quasi-contract that we call the “design agreement” and they pay us a retainer fee to design their house and provide them with a final quote. That design fee has really changed how this business functions. It gives me about an eight week timeline to design the space with the clients. In that timeframe, we can get plumbers, electricians, all our subs out to the space to give us accurate quotes based on the scope of work. And we also have our architects working, too.

We collect inspiration photos, source product, and they come to our office and sit down with all these products scattered and mood boards out, and they get to see everything put together. It’s relationship building as well. By this point, the client either loves it or is like, this isn’t for me.

And then at the end of this tornado of activity, the client is given a final contract with every single thing in their house chosen down to the door hinges and a dollar amount for each of those things, as well as the dollar amount for their build.

That was a very long-winded way of explaining it, but I feel so passionate about that because in typical construction fashion, you’re given a rough quote, usually per square foot, but the client really wants these high-end appliances or cabinetry. To them, it’s not their job to know how expensive that’s going to be. That’s my job, in my opinion. So we’re able to say “This is your bottom line. This is actually the dollar amount.”

I’ve heard about The Job Book. Tell me about that.

[Laughter] I think it makes our subcontractors want to work with us more because we have everything sourced and put together in this beautiful book that we call the job book. It sits on site — the page count depends on the size of the project. It has everything in it down to the light fixtures, where they’re going, the vanity sizes, how tall we need the plumbing to be, what the specs are of every single appliance in the house. The job book is our bible.

Subcontractors were so annoyed because every time they’d call me, they’d ask “Where’s the vanity going? How many lights do you want on that side?” and I’d tell them to check the book. Now, when somebody asks someone from our Eagle Hill team or one of the, you know, plumbers there a question like that, and they respond, “Check the book,” I feel like a proud mom. It’s probably cut down my on-site job questions by about 80%.

I know social media has been key for your business. Can you talk about how you’ve used social to grow your business?

I can honestly say that I need to step up my game. It comes and goes. But in the beginning of this journey, I remember making the social media account prior to even having a business name. We like had like a generic name about like me and Nick renovating houses for ourselves. And I said to Nick, “Why would anyone even wanna follow us? I don't get it.” It didn’t seem interesting to me. You’re just renovating houses every day. But when we made the account, it was like we found this community. We were what we’d call “closet investors.” We didn’t talk about it much. Nobody at our W-2 jobs knew that we owned property. Nobody knew that we’d be going home, covered in concrete, then waking up the next day to go to work.

So once we started sharing truthfully on our Instagram account, we found all these other people who were so much like us, and we started connecting with people in the Boston area and felt this sense of community. The storytelling side kind of came easily to me. My past life was social media marketing, so that helped. But I’m just a transparent person. As soon as I got on Instagram, we had a really shitty run with one of our properties — and I just talked about what was happening on Instagram — and that was the switch. Everyone else shared their own stories too. I talked about the struggles we had. Emotional, financial, everything.

Big picture, can you talk about the current state of the business?

So today, we have seven doors between South Boston and East Boston that we currently run and manage ourselves. That’s our property side. We’re hoping to expand that. All of our properties have been house hacks. We’ve moved a lot — more than I’d like. Our next goal would be to purchases income properties and use them as rentals in this area, but not having to move to them. So, that comes with a higher down payment, and the deal kind of changes.

From the Eagle Hill Homes perspective, we have a very big project that we’re working on in South Boston. We’re super excited about that. We’re doing a three unit condo conversion for an awesome client. And then we have our typical kind of single family remodels happening as well.

On the Eagle Hill Homes side of things, my heart really wants to design and do significant scale projects. I want to take a whole house and redo it. In the beginning, it would be a kitchen or a bathroom, and I would be inclined to take it. Now, I’m learning that the projects that I want are the ones I’ll be most passionate about, and I’d like to lean into those. If there are projects that don’t light a fire, that’s OK. I don’t need to have the mindset of taking everything that comes my way. I say “no” a lot more than I say “yes” nowadays, based on scope, based on process.

Have you always been drawn to the design side? How do you develop that taste?

Getting into the business, I think I had some sense like, these things will work together, or they won’t. But my biggest turning point was the first couple clients who allowed me to run with it. They gave me a lot of confidence, but there was a lot of fear too of course. After it was over, when they were super happy with it, knowing I had put it together, that gave me me such a boost of confidence to try new things.

The main thing now is just to not be afraid of something new, and just try it and go for it. I'll think of something like, “Wouldn't it be really cool if we did tile all the way up to the ceiling?” and what I've learned is my contractors are always like, no, no, no, no, no, no. Because it’s a little crazy, it’d be hard to do. But then we do it, and it looks awesome.

So I’m starting to work with different vendors who go above and beyond the typical. Four years ago, a lot of the design I was doing was on a rental property, and I always had Nick in my ear — even though we’d live in these properties, and we’d do nice things — reminding me that we would have tenants.

I never had real formal training in design. So the business has been able to give me this level of control over design that I wasn’t able to get with my own properties, and I think allowed me to flourish into being a better designer. My goal and dream is to continue to build the design portion of the business with other females who have no prior training, and this can kind of be their first tick on their resume.

On that note — what’s your experience been like, being a woman in a male-dominated role and industry?

Initially, I was nervous to go into this GC world, this male-dominated industry. My first feeling of fear came from people not taking me seriously, which is, I think, the top thing that most women would feel. Because of that, I believe I needed to make the business as legitimate as possible, as quickly as possible, and that was also a driver of implementing all these systems and processes, and not wavering on that. A lot of clients or even subs would just say, “Well, this is how I work.” And it would be so easy for me at that point to say sure, we’ll do it your way. But my immediate response, even early on, was like, too bad. Take it or leave it. I’d literally be in the car, shaking after I told the subcontractor off until he called me and was like, “Okay, whatever, I’ll do it your way.”

So, I went into it knowing you have to be headstrong, and that you can be very quickly trampled over or put to the side, like, she doesn’t know what she’s talking about. With that said, I also had to learn, and I’m still learning so much. You don’t know what you don’t know, and don’t know what you haven’t done. And I’m in no way proclaiming to know everything. It’s hard when you’re a woman and you ask a lot of questions. People assume you don’t know. So I’ve learned to ask these questions in a way that you start with something that you know. I try to know a little bit about a lot. “I know you do this, but what’s happening here?” I did that early on to help me figure out who I could trust, and who wouldn’t see me and think, easy target. And it happens with men too. It happens with anyone who doesn’t seem well-versed in the industry.

So, that was tough for me, but I’m happy and proud of myself for how I’ve handled it. I’ms till learning a lot, but I’ve made a ton of incredible connections with a lot of my subcontractors who I would say now respect the hell out of me, which is all I’ve ever wanted, and I can always go to to ask questions.

And on top of that, we haven’t talked about it yet, but I hired my father-in-law full-time, took him off his union salary, and got him on my payroll. Got him a laborer who now works with him, his dream truck and all the tools he wanted. He’s my pillar in all of this as well. He’ll always call me and say, “Sam — make sure they’re not taking advantage of you!” He’s a huge part of this business who I couldn’t run without. He always has my back too.

So all of those things have paved the way for it to be easier than I initially expected, but I still have to stand my ground and know that this is who I am, this is how I run my business, and if somebody doesn’t want that or tires to alter that, I need to stand my ground.

Thanks to our Boston Developers to Watch 2023 sponsor, RD Advisors.

What’s it like to employ your father-in-law?

It’s crazy, because I was at their house eating out of their snack cabinet when I was 14, and here we are. So, it’s a cool, full-circle moment. He’s the best. We fight — I fight with him more than I fight with my husband or my dad. We scream at each other, like you’d think someone is being murdered, and then he’ll call me and be like, “Hey, do you want to go out for ice cream?” [Laughter]

He’s foreman and lead carpenter. He’s so incredibly talented. He never had the avenue to really do everything he could. Really early on, he had a concrete business, and he was an absolutely incredible mason. It’s one of those things where he stopped school in ninth grade and he’ll ask me how to spell “refrigerator,” but he could build a whole house with his eyes closed. So it was so cool to do the backend business stuff that he wasn’t able to do, the estimates and the billing and things that stress him out. He doesn’t have to deal with any of that.

What’s your approach to working with subcontractors?

For quality of work, I try to stick to my guns. It’s not like I’ve been doing this for thirty years, but knowing what a good tile job should look like, for example, helps you know when it’s not good. I’ve done enough on my own to have a basic knowledge. I have my father-in-law who can also help and step in. And I have a base of subcontractors where if one electrician is pushing back on me, I can call somebody I trust and ask them those questions.

I Probably push back more than I should, but I think that I need to show that I’m not just going to step back and let you do what you want, or talk me into thinking it’s fine. I have conversations where I’m told that the homeowner is being too picky. I have some homeowners that want what they want, and I get it, they’re paying for it. Just yesterday, I was having a conversation with someone who was like, “I know it’s not perfect, but so-and-so is being so picky…” and I literally said, “Hey, does this look good to you?” and they’re like, no, it’s not great. So I say, okay, so let’s fix it. Otherwise I won’t want to put my name on it and you won’t want to put your name on it. Usually in those situations with subs, I can kind of get them to see that side of it. We make the client happy, you have a great product, I have a great product, and we walk away.

There have been uncomfortable moments, but they’ve all been great learning experiences.

Why do you think house hacking has taken off?

I could talk forever about house hacking. In an expensive market like Boston, we knew very early on that we wanted to live in the city and be city people, but we didn’t have the budget to pay rent for the next ten years. Number one, I would say that younger people want nice things. They’re willing to work very hard for the nice things. And they want typically a lifestyle that’s nicer than they grew up with. We love our family more than anything. They’re very blue collar, and there were a lot conversations around money and whether we could afford those things. Nick and I had that moment after going to college, we had an education, and wondering like, what can we do beyond what our parents tell us, which is, “Get a good job and work really hard.”

That’s when real estate came into play, and specifically house hacking. If we can purchase an asset that will work for us for the next X years that we’re alive — the next sixty plus years — and we can purchase it by only putting $30,000 down, why wouldn’t you do it? I think our first property was about $650,000. So call it $50,000, and then we renovated it. And I know that’s not a little amount of money. We were scraping by. But knowing that we can do this now, it’s going to suck for a minute, but in a year — and this is for me, since I don’t like waiting for the long-term gratification — after it’s been demolished and we go through every penny we have, we’re going to live in this house that’s been beautifully remodeled for free, and for the rest of our lives, this place is going to make money for us.

And that was all I needed. It did take a little bit of convincing. Nick was definitely the catalyst for that one. But that was all I needed to understand that it was going to be worth it.

Why don’t more people try house hacking?

A lot of people don’t know how to go about it, even if they want to house ack. They like the idea of living mortgage-free or close to it, but they’re scared, and rightfully so. They may not know anyone who’s done it personally, even if they saw someone else do it on Instagram. They don’t have anyone who can vouch, first-hand, about how this is a great way to build generational wealth. And often, many family members, if they aren’t in real estate, are very skeptical of it because of the risk.

So we decided to develop a course to teach people, step by step, every single thing they need to know about house hacking from finding the deal and the team you need, all the lending guidelines — which Nick can speak to in his sleep — all the construction worries, what to look for in a home inspection, how much it’ll cost to do a lipstick-on-a-pig renovation, what to do if you want to gut the place and want to live in it, how to find tenants…all of it.

We decided there’s a need in the marketplace and we put feelers out, put it on Instagram, said we’re going to host a workshop, and just wanted to see if people would be interested. It sold out in an hour! We rented a space, got catering, and Nick and I threw together a four-hour presentation running through the basics. Forty seats. We thought it’d be like having a birthday party and having no one show up, but it sold out. We actually had someone reach out to us after the course saying they bought their first four family property and they wouldn't have been able to do it without our workshop.

So then we were like, why not take this four hour course, make it twenty, and sell it? So we’ve been recording for quite some time now. It’ll be at There will be a lot of free resources that we’re going to be posting as well, Q+As, deal analyzers, calculators, all that fun stuff will be included.

Thinking three, five years out — what are some things you’d like to tackle business-wise?

From a properties perspective and a homes perspective, I’d love to merge the businesses and do single family custom build developments to sell would be really cool. I would love to be able to be my own client again and have this incredible infrastructure that we’ve built and all these systems and processes help us build or even renovate. Then we could take that income and continue to build our rental portfolio, because we’re definitely in the rentals-for-life mindset over here.

Imagine the year is 2033 and there’s a hot new neighborhood in Boston that’s being developed. What do you think it’ll be?

I would say Winthrop. It’s a hidden gem. Sweeping water views, close to East Boston, a ferry ride away from the seaport, and so many lots with some serious potential.

Any last thoughts about life as a developer that we didn’t touch on?

My hope is that other women get the guts to go ahead and do it if it’s their passion as well. I think a lot of women who have a passion for real estate think that being an agent is their calling because it feels like the right way to go, and my hope is that the fear of this male-dominated industry won’t hold people back. That’s why I’ll continue to hire young women and do what I can to shed light on the fact that women can do it too.

I would also say again that it’s okay to not know everything and not have a great “on paper” resume. All you need is a little bit of passion, some guts, and just jump right in there. You don’t even need any money at this point in life, right? We started this business with $0 and to this day have just used the profits to fund the business. I’m definitely not someone who takes a ton of risks, I like to be very calculated in what I do, and for some reason, I still had a pull to do this. And I’m so glad I did. I want other people to do the same. I know there are other young women and men out there afraid to take the first step, but that’s the scariest part. It’ll never be harder than the first step.

Last thing: As a kid, what did you want to be when you grew up?

I wanted to be a hairdresser. My mom was like, you can go to college and then decide to be a hairdresser. So, that went away quickly. I’m not very good with the scissors.


At O'Kane Marketing, we help developers realize their visions — whether that's through renders, websites, social media, or all of the above  — and Developers to Watch is our way of shining the spotlight on developers' careers and work. We appreciate the support of our sponsor, RD Advisors. Thanks for reading!