Jason Santana | 6 Boston Developers to Watch in 2023

Whether it's moving to a new country at 17, juggling a few jobs, or starting everything over, Jason Santana loves a good challenge.

NAME: Jason Santana

COMPANY: North America Development

You’re from Brazil, and you moved to Boston at 17. Can you talk about that transition?

Truthfully, it was never a plan to move to the US. I was from a very small town in the middle of the Amazon. I was finishing high school and there wasn’t a university nearby. At the time, we didn’t have the financial means for me to move to another city and go to a university. But I had a couple uncles who moved from Portugal to the US — they always helped my mom, my family, financially. So one of those uncles suggested that I move to the US to work and build a better future.

Being 17 and living in the middle of nowhere, I was like, “OK!” I didn’t really think about it. I got a visa, boarded a plane, and went to stay with an uncle who I actually didn’t know that well at the time. He lived in a 3-bedroom apartment with eight other people, so I was the tenth person coming in. Most were immigrants from Brazil, and everyone had two or three jobs. Very work-oriented. I literally arrived on a Sunday and started working as a dishwasher on Monday, at the restaurant where my uncle was a chef.

How did that environment influence you at that age?

So I was very lucky, privileged, blessed, however you want to see it, that when I arrived, everyone was extremely hard-working. There was no time for messing around. I remember vividly — I arrived and had just one job. I was the only guy with one job in the house. I’d be home by 4 or 5 o’clock, and everyone else was leaving at 6 in the morning and getting home at midnight. I worked as a dishwasher at Silvertone, a restaurant in Boston, and then I started working as a dishwasher at the Beantown Pub right next door. I’d keep my apron on, and just head over into their kitchen.

My first day working two jobs, my uncle was extremely proud, and said something like, “Welcome to the world of having two jobs. Now you’re a man.” At the time, I made in a week what my mom would make in a month in Brazil. So I could financially support my mom and my dad, and my brother — he was still in Brazil, but he would come over six months later.

And then I got a third job! My other uncle had a cleaning company. He would pick me up at like 5 in the morning, and we’d clean this restaurant, the Armani Cafe, from 6 to 8, then he’d drop me off at Silvertone, I’d work there like 8 to 3, and then from 4 to midnight, I’d work at the Beantown Pub. That was my first year or so in the United States.

Was there any sort of learning curve?

One thing that was great for me was that my uncle was always telling me, “You need to learn English.” Unfortunately, there are a lot of immigrants who have been here for 10, 20 years and don’t speak the language. So Thursday night was my only night off, and I went to take English classes. To me, I had to. I didn’t want to be a dishwasher for the rest of my life. If I didn’t start speaking the language, I wouldn’t be able to move up the ladder.

I can’t take the credit for the initiative. It’s more like, the environment required it. We’re shaped by the environment we’re in. I was put in an environment that required hard work. And to make more money, I would have to learn the language. So it wasn’t like, I was planning on taking over the world, it was just like, to make more money, learn English.

Did you always have a great work ethic, or was that learned?

The hard-working part, I truly believe it comes from my mom and dad. My brother is extremely hard-working. My brother and I, our first business at ten years old, we were selling eggs on the street. We had a big yard, a bunch of chickens, and so selling the eggs, that was how we made money. We were just raised in that environment.

Today, I really look for more of a balance. I enjoy my exercise. I really do love my job, my company, my team. We have a lot of fun together. But I’ve worked really hard to pass that hard-working mentality to my kids. So they have chores and things around the house that they must do. My son is 14, so this past summer, he worked as an employee of the company.

So, yes — there’s more of a balance today, I don’t work from 5 to midnight anymore, but when you’re a small business owner, you’re kind of always working. I’m not as hands-on on a construction site as I used to be. It’s more dealing with investors and management now, and in a way, it has a heavier toll than being a dishwasher, cook, or even a carpenter. Mistakes cost more.

What was next for you after the restaurant business?

After a couple years of the restaurant business, it was nights, it was weekends — I noticed that it wasn’t what I wanted for building a family. So I left to join a painting business, making half of what I used to make. And that was fine, because at the time, it was just me, sharing an apartment with four other people. I knew I’d make less, but I knew it’d be for a short period of time, and that I would learn a lot. I never wanted to open a restaurant. When I started painting, I knew I could eventually open some sort of business like that.

So in my early 20s, I left to work for a painter. And the owner of the paint company moved to Florida and kind of handed me the business, more as a manager than as an owner. It was a different kind of setup.

So you link up with a painter. Were you thinking of real estate or development yet at this point?

No! And the painting business didn’t go very well. My contractor went down, and I went down with him. I was very inexperienced, and I didn’t set it up how I should have, or prepared how I should have. After a couple years, the business was basically broke.

And that takes a huge toll, emotionally. You just feel like you’re a failure. So that was right around when Katrina happened down in Florida. I had a friend who moved down to Pensacola, where Katrina really hit. He was there for a month and called me, and was like, “Hey man, there’s a lot of work here, you’d probably do well…” so I put some clothes in a trash bag, got into my white Honda Civic, and drove to Pensacola. I drove straight there, with a map, and stopped only four times, for gas and Red Bulls.

You relocate to Pensacola, and you’re basically starting over.

I slept on a couch for over a month. I was literally just driving around, knocking at job sites. And I met a carpenter. He didn’t speak English, but he knew the profession. He wanted to partner up. I told him I didn’t know anything about carpentry, only painting, but he knew I spoke English, and so that was enough.

We drove by a subdivision, talked to the contractor, and we were like, “We do carpentry and painting, and we’re looking for work.” The guy said he needed a carpenter, not a painter. It was a little cul-de-sac. We gave him a price to do the trim work, and we won the job. And we agreed to split it.

He taught me how to cut, how to measure, and then we kind of took off from there. We started getting jobs. And the business grew.

When you started on the carpentry side, did that lead to other opportunities?

I met a general contractor who made me an offer to be a project manager for him. I was like, “Bro — I’m a painter, carpenter, and cook. I don’t know how to project manage.” He literally handed me a set of plans and said, “You seem to be very hungry. Take a look at these plans. We’ll talk on Monday.”

I spent the whole weekend looking at the plans, watching YouTube videos, trying to understand. I called him Monday. He said he’d give me $1,000 per week, and send me to a job site to train with another project manager. I said, “I’ll go for $1,200.” I love negotiating. He said $1,200 was a little much, and then I said, “I’m going to make you a lot of money.”

So I went in and learned how to project manage. They were building a smaller house. And the second house, he was like, “This is yours.” He put me directly in contact with the clients. And back then, this was already an $800k house, which, looking back, I’m like, holy shit, this guy was crazy giving me this project. But the client was kind of a builder, too, and recognized that I was hungry. I was the first to show up, the last one to leave. People would tell me to jump, and I’d ask how high. When you take that attitude, people want to help.

Financially it was good, but the experience was just amazing.

At this point in the story, you’re a project manager in Florida, you have some sense of stability. Things must've felt pretty good.

We’re living the best life. I bought a house. I have a newborn. My house is probably ten minutes from the beach. I have a job I enjoy. We’re building vacation homes in Florida. Then 2008 happens. There’s no more work. And literally every job that we had stopped. Some homes had drywall half-way, and it stopped. It went from my best life to “I’m screwed.”

My boss tells me that he’s going bankrupt. At this point, he owed me two months of salary. So I got home, and I go to my room crying. I’m thinking, what am I going to do with my family, and this house I just bought six months ago?

Was that like a rock bottom? What did you do next?

I spent a couple days at home. I literally had a thousand dollars, maybe, in my bank account. I print some business cards on my printer and drive around, and there was nothing. I got one job — to build a deck for someone’s house.

My brother was still at the same restaurant in Boston, and was like, “There’s no recession here.” So I drive back up to Boston, got a little pickup truck, my wife packed me a suitcase.

I drive up, and knock on the door of the restaurant I used to be at, Silvertone. They welcome me back with open arms, and say they need people. I went back to working 80 hours per week. I’d open and close every day. I went back to living in my brother’s living room while my wife and our baby son were still back in Florida until I could find a place for us to rent.

Were you feeling grateful to have the work, discouraged to have lost some of your progress, or some mix of the two feelings?

I needed to make money. I have a wife who just had a baby and can’t go back to work, and I need to pay a mortgage down in Florida. So I talked to the restaurant owner and told him I’d like to work as many hours as I could. It got to a point where the team there was like, “You’re just working way too many hours.” I was opening and closing every day, six days a week. They were closed on Sundays.

Your mind goes to a bad place. “You’re a failure.” But you’re you’re own worst enemy. You say things to yourself that nobody would say. It was so sad, because my wife hates the winters…and I had to tell her that they had to come back to Boston.

I tried to do a short sale on the house, but couldn’t do it, and we got foreclosed on. I couldn’t afford rent here in Boston, it was — and still is — extremely expensive. I went back to Florida, picked her up, and went back to Boston to my little apartment.

It was extremely depressing, because we had a nice house, a yard, close to the beach. And I went back to the restaurant business — cooking in one restaurant, and being a waiter in another. You just feel like you’re a loser. I’m sure I made mistakes, and shouldn’t have put myself in that position.

I hear this, all your hard work, and it just sounds inspiring! But obviously, I’m sure it didn’t feel that way at the time…

Yeah, it didn’t feel that way at the time! (Laughter.) But that’s the blessing of this country. I wasn’t born here, but I am an American citizen now — even though when I say hello to someone, the first thing I get asked is “Where are you from?” and I’m sure there are a lot of people who wouldn’t consider me American, even though I carry an American passport, because of the political environment we live in right now.

I’m extremely proud to be in this country, and I’m extremely thankful. There’s so much opportunity. When people say the American Dream is dead, it is not. It is not dead. When you travel somewhere else, you see how much opportunity we have here.

I know a lot of immigrants, just like myself, who arrived here — no English, no documents, who are extremely wealthy today, because they follow the rules and do the work. Americans are very grateful to have people who do things, and get things done. To be an immigrant is a privilege, not a burden, because we already know, “This is great.” Being homeless here is still better off than a lot of countries in the world. So that’s why you can fall and get back up, fall and get back up here. There’s opportunity here. The streets are literally painted with gold.

I’ve been living here for 22 years and I’ve never been unemployed. I can always find a job. Yes, sometimes you do things you don’t want to do, or not make as much as you want, but you’re not going to starve.

I was talking to my son a couple days ago. He wants a PC. He has a little crappy laptop for school, and I guess all his friends — he’s 14 — have PCs to game. I asked him if he really wanted a PC, and he said yes. Then I asked if he knew how much a PC cost, and he said no…and I said it was probably about $1,000. So I said, “Why don’t you go earn a thousand dollars?” And he said “Can I?” and I said “Yeah!” I told him that even though he goes to school, he doesn’t do anything Saturdays or Sundays, so why not go to any store nearby, and just say you’re looking for work on Saturdays and Sundays. You’ll earn your $1,000, and you’ll buy your PC.

Because of this amazing country and the amazing opportunities it offers, it gave me the chance to bounce back. I went broke three times, and hopefully I don’t go broke again. But if I do, I’m not concerned that I won’t have shelter or food. As long as I’m healthy, I know I can go back to work. Brazil is not like that. This message needs to be reminded, because everyone blames the government. And I know everyone needs help at some point, but I feel like the American Dream is alive, and I see it every day. Most of the people I work with are immigrants, and everyone is grinding, everyone is thankful, and everyone is just trying to have a better life.

How long were you working in the restaurants again before you make your next move?

My brother gave me a book, “Financial Peace University,” by Dave Ramsay. I recommend it. In that book, he has baby steps for how to get out of debt. He gave me that book for a Christmas present. I had probably read one or two books in my life.

I had credit card debt, I had money I owed my brother, and I started reading that book on the T, there and back. I started following the steps. A little less than a year goes by, and I’m debt-free, I have a little bit of money saved. I felt like a human being again. I could work less hours. My son, for the first year of his life, I didn’t see him. I would leave early in the morning and come back late at night, seven days a week. I stand up again.

Both of us, my brother and I, are working at the same restaurant. Hudson worked there for 12 years. About a year and a half started dating a girl who’s his wife now, Lisa, and she’s in real estate. She tells us we should get our real estate licenses. We’re still at the restaurant, and we start doing real estate together. But this was back in 2009, 2010. The market wasn’t that great. My brother sold one house his first year in real estate. We used to joke at the restaurant that he was the best-dressed bartender, because he’d work as a realtor during the day.

So how did you enter real estate?

Hudson started working for the bank, selling foreclosures to investors. Buy, fix, and sell. So one day he comes in, and he’s like, “Jason we should flip houses.” I still felt too burnt from three business failures from thinking about doing something on my own again.

I was like “Hudson, I have a wife, kids.” My wife was working as a housecleaner at this point. I told him I couldn’t open a business right now. I only had $7,000 saved in my accounts. I just had a foreclosure. And he’s like, “No, Lisa has good credit, I have like twenty grand saved, and we saw this house in Everett, so maybe we could buy it and you could do the construction.” I told him I’d think about it.

I went home and talked to my wife. She said let’s do it, so I gave Hudson the $7,000 that I had saved up. He bought the house in Everett. We did some shares of the deal, based on what we invested. But I was going to do the construction, so I’d get $15 an hour.

My schedule at the restaurant was 8 to 3. I’d leave the restaurant every day at 3 and get to the house at 4, and work at the house til midnight or 1 in the morning. I’d usually be alone, but some days I’d bring a helper, some days, Hudson would help me. We did hardwood floors, paint, cabinet, tile in the bathroom. I watched YouTube to learn how to do tile. I still have the piece of paper we kept track of all the expenses on.

So we sold, and my seven turned into twenty-one. We were like OK, this worked fine. So my brother found another house in Everett. We did another house. Then another one in Revere. And I’m still the full-time chef at the restaurant.

When did you become the chef?!

They make the most money!

How long did that arrangement last?

We did our third house, and Hudson was like, “You need to leave the restaurant. And you need to get your GC license so we can make this thing happen.”

I wasn’t sure about it, because I never see the money from the flips. It goes from one deal to the next to the next. I’m still living off the restaurant money. Even today, I take a salary, but the money just goes from one house to another house to another house. If I put money in my bank account, I’ll find a way to spend it. (Laughs)

You must've quit, right?

Well, I wasn’t sure about it, and Hudson says, “What’s the worst that could happen?” And it was a great question. I would have to go back to the restaurant. That’s it. So I sat down with the restaurant owners, and was very transparent with them. They told me I’d just need to find someone and train them, so that’s what I did.

Back then, the restaurant had four owners. One of them, Maureen, saw me leaving one day, and asked where I was going, and I told her I was going to do a demolition. She said, “Can I come?” and I say sure. I’m in Revere doing the demolition with a couple guys. She shows up in her white Mustang, brand new construction boots. She was like, “What do I do?” So I give her a sledgehammer.

One of your old bosses, in a way, starts working for you.

Yeah, she starts doing what I was doing! She was the manager of the restaurant during the day, and then she’d leave, and she’d paint and do all these things. She said to me, “We’re going to sell the restaurant, and I want to come work with you.”

We opened North America Development, and every day, she’d ask where to go and what to do. For a whole year, she worked for us for free — I never gave her any money. She was learning.

And then she sold the restaurant. By then, North America Development, we were doing 3-4 houses a year. I told her it was just me and a few guys on the team, and she said that because they sold the restaurant, she had some money, and she wanted to be a partner. So we did a valuation, and the money she had and was willing to invest was worth 10%. But Hudson and I didn’t want a 10% partner. So we said, we’ll give you 10%, and you’ll buy another 10%.

I’m very thankful for her. I’ve known her for 22 years. When we’re together, it doesn’t feel like work. She was my first boss and was always nice. So we gave her 10%, she invested, and the money she put in literally went into the business.

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So you establish North America Development. At what point did you have multiple projects at once, and it stopped being one after another?

We always wanted to grow. Because of our model, investors started approaching us. We started this with our money, and it was very limiting. So when we got more money coming in, we could start doing more houses, and doing it the way that we like.

This year we’re up to 15-17 houses. We always do a full gut remodeling, not just a paint-and-sell. So our properties usually take a year, especially because of the permitting process.

That's a lot of projects. How do you scale you and Hudson’s time and effort into the business?

The business had to be able to run itself. It’s just a job. I have a job within my business. But I can hire someone else to do my job. So that’s something we learned about six years ago.

We try to have this model where this company isn’t Jason, it’s not Mo, it’s not Hudson, it’s not one person. And because of that, I’m very team-oriented. We start bringing people in.

So that’s how we’re able to run so many different jobs. Right now, we have five project managers. Every project manager can do 3-5 jobs at a time, depending on the details of the job. We don’t have laborers. We have people at the office, like engineers and architects, and we have project managers.

The project managers almost have their own little organization within our organization. I give them the project plans, a budget, and a schedule. We’ll work on it together, and then they’ll go do it. We have to have meetings, there’s software they use to make sure it’s all accountable, but they have the freedom to choose their people, as long as it’s in the budget. For me, that’s how I like to work. I like for people to trust me.

And we pay the project managers bonuses on the project. The better they do, the more money they’ll make. So that’s how we run it.

I know design isn’t your role, but how do you guys think about the homes that you build?

We don’t want to just put boxes out there. Any time we build a house, we ask, “Who’s gonna buy this house? An attorney, a construction worker, a tech person, a family?” And then we work backward from there. At the end of the day, this will be someone’s home, so it needs to be the best use of space so that they really enjoy it. A home in Hingham is different from a condo in Cambridge. We’re trying to really focus on the buyer and what they’ll need. It’s like a minivan versus a sports car.

Tell me more about those books that you give to your new homeowners.

Contractors don’t have the best reputation. Many people have a horror experience. So, thinking about the consumer, the person buying our product, they might not even have a hammer. Actually, we’ve gotten a call from someone who needed help to hang a picture, because they didn’t even have a hammer and nail. So that tells us that a better product would be if we offered an extended warrant.

Since we’re controlling the discussion and doing a full gut remodeling, we want to stand behind it. It’s a no-brainer. We built the whole thing, we have pictures, standards, inspections. And if there is a problem, we’re the people to take care of it.

We give them a book of our contact information. So, if something breaks or doesn’t work as-promised, we let them know that we’re here to take care of it. Everyone who worked on the house is in the book.

As North America Development grows, what’s the biggest challenge in terms of scaling?

I’m more concerned about bringing in someone who fits in our culture than having a specific skill. I think we’re going through some uncertainty right now, with the markets and everything. I don’t think there’s a bubble or that a crash is coming, but I think it’s a cool-down.

Capital definitely holds us back a little bit. Every house here is a million dollars. To grow more, we need more capital, and you can only raise it so fast, safely. Sometimes flipping a house might not sound as sexy as some company’s stock, or crypto, or whatever. We can’t promise 50% returns. Some homes, yes, we’ve had 100% return. Others, we’ve had 6% return. So I can’t go to someone and say, I’ll give you 50 — or even 20% — on your money.

$100k doesn’t take me anywhere. The growth has to be slow. There were a couple years that we grew too fast, and everyone was stressed, we weren’t happy, we weren’t producing as well. So capital and manpower is where we need to scale together.

Speaking of macro uncertainties, is there anything that you’ve changed to make sure that your foundation is sound?

We run a very lean company, so I don’t think company-wise, we’ll make any shifts. On the product side, we’re definitely trying to adjust. As the interest rate goes up, we’re trying to figure out more cost-effective ways to deliver a great product.

Being a small business, it’s easier for me to do that than say, Norfolk. So we’re adjusting with the market so that we can keep buying, adding value, and selling.

Mid to longer-term, what are your business goals?

We want to be the biggest residential developer. I don’t aspire to move into commercial or other types of construction. We don’t need to change our way to grow, we just have to expand. If I take another ten projects, I just need a couple more project managers, and one or two more office people.

So I want to keep the model, and just keep growing. I feel safer when we do a bunch of projects, rather than one big project.

Is there any project that stands out for you as the most special?

That’s the beauty of construction. Last time I was asked this question, I was building my house three years ago, and to me, that was the best. Every house is different. I don’t want to give a silly answer, but when I think of a project, then I’m like, “Oh we’re doing the next one, and it’s cooler!” We just built Maureen’s house in Hingham, and it came out great. We went completely different from what we usually do. It’s the latest finished product we just did — a big single-family house overlooking the water. So that’s the latest, coolest one we’ve built.

Your brother and partner in the business, Hudson, sells the homes, and talks to buyers regularly. How does that benefit you on the development side?

I think it’s a huge advantage for us. Our goal is to build something consumers want, that’s going to be loved. Because Hudson is hearing that feedback every day as a realtor. “Oh, I wish we had more closets. Oh, I wish the laundry was on the second floor,” whatever. When the pandemic hit, we started putting in more offices, because people were working from home, and that’s what he was hearing was a need.

Imagine we’re ten years in the future. There’s a hot new neighborhood in the Boston area doing well. Which one do you think it is?

I think Woburn. There’s great potential. Cambridge, Somerville — very expensive. Woburn isn’t very far, and there’s still a lot of potential. It’s a working-class city, but we bought property in Woburn, and think there’s a ton of potential.

If you had to start over in another city in the US as a developer, where would it be?

I’d probably go to San Diego! The weather there is great.

What’s your favorite part of the entire development process?

I love when we’re acquiring, and I hate when we’re selling. I wish we could keep every house. Every time I drive by a place that we sold, I think, “Oh man, I wish we still had that,” because we leave a little bit of our signature.

It takes a while for someone else to do something to that property — to really, significantly change it. Like 10-15 years. So when we buy a house that needs a lot of work and do something really nice, I’m sad when it goes on the market. Sad in a way, of course. You just think, when you hand it off to the new buyer, “Oh please take good care of it!”

Another beautiful thing about this business is that you can run it so many different ways. You can be a very analytical person and still have a construction company and do the analysis, do the part that you’re into, and have the designers and other people do the other things that they’re into. So, with a little soul-searching, you find out what you’re best at, and then find a team to put around you. Alone you go fast, but with a team you go far. I’m a marathon runner. I’m looking for long-distance. I’m looking at five years, ten years from now. Not Friday, or even the end of the quarter.

Switching it up a bit — as a kid, what did you want to be when you grew up?

I wanted to be a prosecutor. In my little town, there was no prosecutor. It was so small, and we were part of another town. When they opened the office where there was going to be a prosecutor, they had one kid from the school shadow the prosecutor, and I was the one chosen, when I was 15 years old. So I got to see what he did. He carried a gun, he was an attorney. For me it was the coolest thing. Today, I know it wouldn’t be right, but back then, that was it.

Any last thoughts about life as a developer?

The beauty of this business is that we can all do it our own way and be successful. You can approach residential, multi-family, commercial, etc. from many different angles and with different strategies.

I’m sure there are other developers who do business completely different than I do, and they have great results. This industry gives you a lot of freedom to do it however you want. Some people might see my results and think that it’s not enough for them, but it’s filling up my bucket. It’s also always changing — you’re moving, you’re dealing with different issues.


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