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What Is It Like to Shatter Stereotypes in a Male-Dominated Field? Motivational Powerhouse Cindy Stumpo Shares Her Dynamic Secrets to Success

Cindy Stumpo is an entrepreneur, trailblazer, and builder, shattering stereotypes in the male-dominated field of building and contracting. She is the founder of C. Stumpo Development, a privately owned custom home and development company based in Massachusetts. Forbes Magazine called Stumpo’ one of the most successful residential contractors in the country.’ Tune in to hear her remarkable story of strength, determination, and grit to break through barriers and defy the odds in order to be successful in a field where everyone doubted her. Her dynamic personality will motivate and inspire you to overcome any obstacle you face.

Listen to how Cindy shares her remarkable story. Listen to the full episode here:

Click to Read Transcript

Welcome to Underdog. Today we have a very special guest, Cindy Stumpo. Cindy Stumpo is an entrepreneur, trailblazer, and builder shattering stereotypes. And defying odds in a male-dominated field. She is the founder of C. Stumpo Development, a privately owned custom home and development company based in Newton, Massachusetts.

Stumpo and her work has been featured in numerous national publications, including Forbes magazine. Calling her one of the most successful residential contractors in the country. Her construction work and dynamic personality became a television series on HGTV called Tough as Nails. The show is now a weekly radio show on I Heart Radio. The show was about building a house and building a life. Today we welcome Cindy Stumpo.

And I’m happy to be here. I love it.

Thank you so, so much for being here today. So basically, the mission of Underdog is really to talk about like real stories. And I know from watching you over the years like you are as real as it gets. You are Tough as Nails, you’re down to it like the most straightforward human being that I think I’ve ever seen. And it’s amazing. So I’d love for you to sort of talk about where you started. I mean, you have an empire now, which is incredible to see you literally build castles. That’s how I describe it.

Yes. Because I started off all kinds of, start with smaller homes. I said at 23 years old, nope, this is what I’m going to build big homes. Beautiful. I call my homes… some people say they build transitional modern. I always use the word glamour and elegance. Because glamour and elegance never go out of style. Trends come, trends go. And if you’re going to be a spec builder, or a homeowner or a builder that builds for an end-user.

I try to always explain to my clients, if you get caught up in the trends. Your house is going to look outdated in five to seven years. So you know, everybody wants brush nickel right now. brush nickel on the vanities, brush nickel, that’s going to be a fad that’s going to go. You go with polished chrome fixtures, they don’t come in, they don’t go out.

There’s so much that, you know, between all the sites that we have to go searching. People get caught up in these beautiful luxurious-looking bathrooms. But you also have to remember yes to use that bathroom. You don’t. Right. It’s called museum living. And it has to be like work for you and your family. see Oh, look at, we post a lot of beautiful pictures out there. But it also has to be that you live in your home. And you’re not stressing out.

Oh God, I got a black Ebony rift oak vanity and my husband’s using his toothbrush. And he’s getting toothpaste all over the black. You can’t live that way, you have to live in your home. Right? So, you know, if you’re gonna get caught up in the trends. you’re gonna pay… then don’t touch that because I went with all-white countertops. and I don’t want them getting dirty. that’s a stressful way of living. So I try to explain to my clients. Listen, let’s build a beautiful home.

Let’s have you a couple of rooms that are your wild rooms, and then come down. I have built homes for people where they want every room to be the wow effect. And, okay, I walk through this house. I’m going okay, this is wow, this is wow. Too many “wows” are going on. Right? It’s too much. So pick three rooms in the house that you want to be the wow.

The wow should be your master bedroom, your master bathroom. Your foyer when you come in, a beautiful powder bathroom. Some things as you walk into, from the foyer coming into the other kitchen, another big one. And then calm down the family room, calm down the living room, calm down. Not everything has to be loud and screaming. Right.

So I think that a lot of homes that walking through. forgets how they’re decorating them with the vanities and the trends. I’m seeing a lot of bad builders. And that’s disturbing to me because I’ve been out here for 33 years. And 33 years ago, when you came out here to build, you dealt with men, men were men. meaning a quarter to seven, we’d be on those job sites. we’d be having coffee and doughnuts and 7:01 those machines were up and running. This is me today. 33 years later. “Yeah, it’s 10 o’clock. Where are you?”

I was once a developer builder, and then went from a developer builder, to the psychiatrist. Developer, builder, psychiatrist, to owning an adult daycare center. Okay. And like literally like babysitting guys, now down to the mask police, okay. Because if we not have masks on our faces. and the whole nine yards and not following our corporate 19.

And we have in development, all the rules, I have to follow. If the inspector comes through one of my homes. and not every one of these rules are followed, your jobs getting closed down. Okay. So now, now I’m out there and, I’m the mask police. I’m making sure water bottles aren’t left on the job site. It’s so stressful.
When I became a builder. 33 years ago. It was fun out here. I had fun. And then once ’08 hit, and we went into our recession, ’08, 9, 10. when we all had a gear back up for ’11, ’12, a lot of guys left the business. because their wife said, ‘Listen, we need a paycheck. We need insurance. We need 40 hours.’ And I called it in ’10. I said in ’10, when we come out of this recession, we’re going to be in trouble.

We’re going to have a skill gap problem. I was talking about this on my TV show on HGTV 10 years ago. and people laughing say, ‘What is she talking about? What’s the skill gap problem?’ Okay, well, now they know what… now fast forward now they’re feeling the effects of a skill gap problem. But there was a time on here. Like, I was out of bed at 5:30 showered at all my job sites. winter, summer, spring, fall, and loved every minute of it. And it has nothing to do with me getting older, I still love what I do. it’s just dealing with what we have out here for a pool of skilled labor.

Because the good guys already have their builders that they work with. like me, that’s been around for a long time. So now the new builders that tried to put a team together. but the team is just not there. And if the builder is not a good builder to begin with. then he can’t make his guys good. Cuz he’s not good. Right? So I see a lot of going on here is that when like any business. but when the building business is good.

Everybody’s a builder. Everybody is a money lender in real estate. Okay. When the stock markets are great, everybody has their own financial advisor. Difference between a builder that’s been a builder for years and years over a newbie builder. is we have learned to maneuver through good and bad times. That’s part of this game. It’s not just knowing how to be a builder, it’s knowing how to be a business person. Okay?

Because when you’re out there, and you’re buying products. now if you want to be a custom home builder, that’s great. That means you’re spending your clients’ money. you follow their directions. and you do what they want to do. When you’re out here investing your own money. You need to do, make sure you’re doing everything perfect.

But getting perfect is making sure you’re buying the buy right. And you can’t buy the buy right, right now. Cuz there’s too much competition. Especially in my end. No, because there’s not a lot of guys that can still write the type of checks I write for product.

How did you get started sort of, how did you think about getting into the development? Like, I know you were 23 at the time. So sort of tell me the journey of how you got to that point.

I guess somebody would have, like, this great, phenomenal story. how they started in business at 23 years old. Let me ask you this question. What do you know at 23? You know, nothing. Okay, so I just knew that traditional education wasn’t for me. So high school, I obviously graduated high school I graduated. but school wasn’t for me. I’m more hands on, learn with my hands. So I just knew I can’t tell you. It’s such a long time ago. I’m 56 I think that there was just an eye for me loving homes.

So I am from the North Shore of Boston. So I was 13. And when I moved to Newton, when I was living in West Peabody, every house was kind of similar. They brought me to an area called Newton, Massachusetts. And then I started to see homes like I’d never seen. Victorians Tutors. you name it… center entrance, colonials… Georgian, it was a very upper scale city. So it wasn’t just like, three of the same houses built the same. you know, okay, we’ll change the gable we’ll change your roofline. But so that was my experience probably as a 13, 14 years old.

The other thing was I loved was Christmas lights. So with my grandmother on the North Shore. I would drive through areas, this area called Linfield. People had more money in Linfield than they did in PVD. And they decorate their houses with lights. And I say things to my grandmother, like, ‘Wow, look at that roofline.” she’d be like, ‘what are we looking at a roof line for? look at the beautiful lights?’

And I was like, ‘Yeah, but yeah, but that roof lines really beautiful.’ And then she’s like, ‘Okay, well, what about this roofline?’ Yeah, that house is not as pretty with the light side. She’d be like, why? is it not a pretty house? So she’d be like, okay, so we, I’ll never forget. that was our first or second or third year out there looking at lights.
We went home, and she said to my mother, this girl is going to become an architect or a designer or something. But she’s very much like the things that she looks at when she’s looking at Christmas lights. is not what normal girls her age should be looking at. So I guess there were signs there.

And then I just decide, like, you know what, I grew up with a father at home, hair salons, nightclubs, you name it. And I worked in nightclubs at a young age. But he had probably 10 or 12 hair salons, and not gonna be for me… I got my license at 18, I’m a senior high school. So in case something ever happened to my father, I’d have it so the salons could prevail and go on.

But other than that, that just wasn’t for me. So how I got into construction. I’ll say the solidarity. I don’t know, I just did it. I’d love to give you some great, wonderful story. But it would be a story. It wouldn’t be the truth. And the truth is, I landed in there, I fell in there, and I ran with it.

That’s amazing. How did you get to building the first house or, you know, the idea of like, Alright, I’m gonna build my first home. So what was the first, like, stepping stone?

It’s 1989. And you’re a lot younger than me, how old you?


Okay, so my daughter is 33. So 1987 was black market. I was pregnant with her. The stock market had just dumped. Bad, bad. In 1989. It was like the best time to start a business. In my opinion, if you’re going to start a business. always start in the worst times, not in the best times. You think those best times are going to last forever? No… You have to feel bad times. To know love. You need to feel not love to be in a good relationship. You had to be in a bad relationship to respect and appreciate a good one, right?


Take the same fundamentals of your personal life, and put into your professional life. And I came out in 1989. I was 23 years old. And I gotta be honest, I had like, short shorts on daisy dukes construction. I’m like, it’s nine degrees and, I always have a bigger top on because when you’re born, you go into a line… you go, ‘Yeah, I want nice legs. I want a nice ass… Like, back in the boob line.’ Okay, and they just kept getting bigger and bigger. So I was 23 years old and I would be out there ‘please thank you’s. but I didn’t know enough yet to open my mouth. I was the maid out there.

So even though I had my GC license, I learned by putting a broom in my hands. And that’s how I learned this business. I learned in my own company from the ground, right, the lowest of the point… broom gets in my hands.

And then I would take a look at what you’re doing. And when you’re cleaning and vacuuming, in your playing labor on a job site. you’d be amazed at what you pick up and what you learn. School taught me so much, getting my general contractor’s license taught me about codes. The rest was on the job experience, they start to say, Okay, you know what? You know, buddy, let’s just try it this way.

Well, but I do it this way. I hear you. And I always would say to a guy, because those guys were twice my age. At that point, you’ve thought more than I know. So I’m not out here trying to push my way around. because you have you forgotten more than I know. But we’re gonna still try it my way. Okay. And if I face that, I’ll be the first to say I fell on my face.

Let’s go back to your way, right. But we try it my way. Because I see a way that we can run these plumbing lines, electrical lines, HVC. You know, you’re hogging up my basement to be able to finish it. You’re not thinking early on what’s coming down the road if a homeowner wants to finish this basement. And that’s how it came to fruition.

And then you get to a point where your guys that, you know, again. at 23, 24, 25 it’s please and thank you, and you try to be very polite. And I’m in Boston, I’m not in North Carolina, where everybody is very polite, right? Boston is hardcore.


Tune in to the episode to hear the rest of my truly amazing and inspiring interview with the one and only Cindy Stumpo!

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The Underdog Podcast host is none other than Pamela Bardhi. She’s rocking the Real Estate Realm and has dedicated her life as a Life Coach. She is also Forbes Real Estate Council. To know more about Pam, check out the following:

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