Undercover Billionaire's Elaine Culotti On The Show, Her Career, And More - Exclusive Interview

There's a lot to be said about small business owners, and Undercover Billionaire star Elaine Culotti knows that firsthand. So many small business owners follow in the footsteps of their parents and grandparents, who worked tirelessly to create their own sense of prosperity and security. Others had an idea for their community, a business that would give back, and were determined to see it through. Some used their skills and talents as entrepreneurs to make an impactful, lucrative career for themselves, and that's where Culotti comes in. 

Culotti is a visionary — a designer who sees iconic spaces not for what they are, but for what they can be. Her claim to fame within the design and construction industry was her work on the venue House of Rock (via Distractify), and her career just skyrocketed from there. What inspires Culotti's worldly approach to design? Her upbringing and the number of cultures and experiences she was exposed to as a child. Some things just innately come to her, she said, that she feels as though she taps into previous lives and past experiences. 

In comes as no surprise that Culotti was tapped to star on the second season of Undercover Billionaire, an unscripted reality show that pits three entrepreneurs against each other for ultimate business prosperity. The goal? To create a million dollar business in 90 days with just $100 in their pocket. Culotti is up for any challenge, and she sat down with The List to talk about her career, her time on Undercover Billionaire, and more. 

How did Elaine Culotti's childhood influence her career?

I know that you credit a lot of your early taste in design and style to the multicultural upbringing you had. I want to know what it was like for you to turn your life experiences into such a booming business and career for yourself.

Well, first of all, I'm not so certain, but I suspect that what we see before we're really patented, before we're really a real adult person, and we're fixated on things that we've already learned, before we're there, I think that because children are such an open book, that those things that you see and those things that you hear and those things that you learn when you're little, they become part of your cloth, your DNA. So I can look at something old and tell you if it's real or if it's not. I don't know why. There's something about me that knows that it's more than just looking at it. It's the texture. And I can see the patina, and the wear and tear and history. I see like the whole story. And if something doesn't have a story, then it doesn't feel authentic to me.

So that's something that's in my DNA from when I was young and that has certainly transpired into my adult life. What's your story? I remember I saw a movie once about that. Was it Australia? With Nicole Kidman and they were talking about how they have to have a story, and if you don't have a story, you're not alive. And I really identified with that. And so for me, my story is what brought me where I am. The things that I learned when I was young that are so part of my cloth. They're my clan.

Elaine Culotti reveals what aspects of her early life impacted her perspective

Like you said, when we're kids, adolescents, going through those times of development where we learn so much so quickly, you just absorb, you're just a sponge. 

And there's many things that will stay with you as an adult. I'm 55. So when you're my age, for example, I still like certain foods that I liked when I was a child. When I'm angry, my little English accent comes out, but not when I'm not. And when I sleep, I like feathers and down. It's not because I can afford feathers and down, it's because when I was little, we grew up on feathers and down. So it just feels like the womb to me. I speak a German language sometimes because I lived in Germany, but it was hard for me to learn Spanish and I speak terrible Spanish because I learned it when I was much older. But German, I don't know, it just... I think I dream in it sometimes. It's not even in my daily life, but it's something that's in my DNA.

Something that is so consistent from such an early age. It's amazing how we retain that kind of information.

Well, a lot of people believe too, it's generational, in that it's historical from... Some people believe it's other lives or different lives, but explain to me why I can ride a horse and no one ever told me how to ride a horse. I don't know. But I love to ride them and I'm not afraid of them. And I come off them all the time, and I think that's part of the process. If you're like, "You can't fall off the horse." Well, if you fall off the horse, you get back on. It's part of the process.

This was the project that stood out to Elaine Culotti

There have been some standout designs in your career. I saw that you got your hands on the House of Rock here in L.A. I'd love to know what inspires you when you take on a space and what projects you've had throughout your career that have really stood out?

Well, I had an inkling that I would do design work when I was very young. I used to move the furniture around in my parents' house, and sometimes even in the middle of the night. And it used to drive them crazy, but I was always about my environment and my space. And in technical terms, everybody has their magic superpower. And I always could see empty space full in my head. It didn't matter how big it was. My dad used to say, "What's the greatest room, the biggest room in the world?" And I would say, "I don't know." He said, "The room for improvement." So in that empty space, as I've become an adult, I see everything full, abundant, with things other than furniture.

So my House of Rock was not about the house. It was full of music. I saw it as a giant recording studio. And it was an idea, not a thing. It was an art project, an installation of music, which brought a home to the house. Because the house was inspired by Kathryn Grayson, who was very good friends with people like Frank Sinatra and William Randolph Hearst. And they would play music all the time in the great room. And it had a Romeo and Juliet. I mean, it screamed rock and roll to me. It was just this place of people... Many things had gone on in history there that weren't there. We didn't have them. So I recreated it.

It's such a storied place with so many different kinds of people who have inspired it, who've walked through it. So I'd imagine it was really kind of putting those [details] back into what people can experience when they walk inside.

It's super magical. But, again, the important thing about things like that is that you put them up and you take them down, because they're little dreams. We lose the imagination if we can always go back and refer to it. 

And we're an electronic era. We're like, "Download it, I'll watch it later," and save all my pictures. I get reminders now of what happened a year ago. I mean, I should be able to remember that. So I think that to put things up and to take them down, to limit access, give access to those who can't, not those who can pay.

Did Elaine Culotti watch Undercover Billionaire to prepare for her season?

What was it like to get involved with discovery+ in the first place and to get involved with the second season of Undercover Billionaire? Did you watch the first season to get some inspiration as to what it was going to look like? 

All right. So, this is the truth, honestly. And the reason I didn't watch it is because I wanted to be authentic and have my own journey. And I didn't want to pirate anything that Glenn had done. But about halfway into... actually about, I would say, a third of the way in, the network wanted me to watch it because they're like, "Elaine, seriously, you don't know how to make television." Because I was having none of it. I was like, they're following me, I'm doing what I'm doing. And it's not so simple. And I'm so lucky to have had to have been with the team that I was with, my production company that found this jewel of a show and then created these scenarios that would work for each one of us individually. Because they had to pick where we were going. We have no say in any of it. So they find like, "Where can we put Elaine that's going to be so helpful to the place and so helpful to the message, to create the story." And then all of a sudden I'm just there and I'm like, "Why did you pick here? What?"

But they did the right thing. They picked the right place. And then they gave me the best discovery is like... I can't even tell you like. Because I was scared a little about reality television, like what are they going to do?

Elaine Culotti thinks that viewers can get a real education from Undercover Billionaire

[On Undercover Billionaire

This is entertainment, television as a class. This is learning something in school. You could take three classes at a university, at a top notch university. And they would be Business 101, entrepreneurial-ism, right? And some sort of statistics or organization skills that have to do with what the outcome is going to be. Those three classes would cost you an absolute bundle at a college. Okay? And a lot of homework and a lot of testing. And you can literally watch the show and graduate from those three classes. That's the takeaway of this. We give you a sensei interview and we say to you, "This is my strategy." And that's been developed because when you're on the ground and you're going really fast, and you're someone like me, right? You're not explaining yourself. And people get... They're like, "What are you doing?" And I'm like, "I've got it all figured out." You're not teaching anybody anything. You're just running and doing. So you have to stop and go, "Okay, so this is my strategy," which is hard. "This is what I'm thinking I'm going to do, I think. I'm on this trajectory and this is my goal. And this is how I think I'm going to get there."

Really slowing down and explaining the process, which for someone who is so such a pro and so vetted in this industry, was it a challenge in a way to you?

Oh, it's impossible. Absolutely possible. You have momentum and you're going, and they're like, "Wait, can you back up? Can you run one more time through there?" "Why?" Because they want to get it from here and they're just running one more time. Because it's non-scripted reality. It's just real. I almost had to sleep in my car. Downtown Fresno during the pandemic was not pretty. It was close. But the team was like, "No, Elaine, you've got to find a place." Because, as a woman, it's irresponsible. And who knew where I found would turn out to be what it was, it was insane. But let me say, it could've gone either way the entire time. I could have been in my car, down in a camp city with tons of people. I mean, anything could have happened.

Elaine Culotti reveals her thoughts on femininity in the workplace

I want to talk to you about being a woman in your industry. There are so many more things that we have to be aware of because of the fact that we are women that I think a lot of people will gel onto when they watch your journey through the show, because it's groundbreaking on a lot of levels.

There's a lot to be said about our femininity and there's a lot to be said about our masculinity. And we mustn't sugarcoat that. Because what we're doing, the neutered States of America, we mustn't, we mustn't. It's very important that we embrace not just our femininity as women, but also our sexuality. We have to take control of when we're being destabilized. And all change comes with adversity. All good things are hard to get to. There's no easy path and there's no right path because it's new. We're learning as we go, we are. And we're such a new country, right?

Compared to France and England and Egypt, and even given that we're brand new, right of the gate here, just a couple of hundred years, we are pretty hard on ourselves. Think of our progress. Because no one's perfect. 

I mean, we get a little crazy, I think, expecting change to happen so quickly. And so the beginning of the feminist movement was not Harvey Weinstein for God's sakes. It's an old... I'm 55. When I was in high school, it was the '80s. I was like shoulder pads and Madonna. I was like bobby socks and stilettos. I was a girly girl. I had curly little permed hair. And we used to put the white eyeliner on. Who would think of such a thing? And remember the big belt kind of slung low? These are moments in time that were so much fun. And if I wanted to go out to a bar and kick the door in with my confidence, so what? So what did I do wrong? And so now then, that comes into your adulthood and you start working in a corporate world. And you realize that if your bra's tight enough and those are up there enough, your door opens a little bit quicker than the guy next to you, and this asset is an asset. And so now how do you harness that femininity without being abusive?

What was Elaine Culotti's early career like as a young, professional woman?

How difficult was it for you to navigate the work field, especially in your younger career? 

I think as a young, gregarious, good-looking girl, and instilled with confidence from my father, my life was imminently that much easier. Right? It was just a walk in the park. Because I was very sure of myself and I was sure of my femininity and my sexuality. And if I needed to use that tool, I did, my whole life. Even now as an adult, I still rely on taking care of myself and looking the best that I can look. And I am the feminine woman that I am. I can't take that out of me. That's who I am. And I raised a very incredible, beautiful daughter. And I watched the environment as she was being raised create moments of pivot where that luxury that she had could go either way. It could become her No. 1 skillset, or it could become her asset.

The most important thing was to teach her confidence and to be smart. And that beauty is just... First of all, it doesn't last. Let's be real. It doesn't last. It's not going to get you all the way there. It'll open doors for you, but it's as superficial as the person that opened the door, right?


If that's the only reason they're letting you in the door, you've got a whole other set of problems. So to be aware of that. In construction and in design, it's just a door opener. It doesn't do anything else. In fact, the most important thing to remember in a man's world is that you're underestimated all the time as a woman. 

And so for me, and I encourage other people to think the same way, never underestimate the value of being underestimated. It's an incredibly strong position. To be a lot smarter than everyone thinks you are, that's completely fine. Do not strive to be the smartest person in the room. You've got nothing to prove. You've got nothing to prove. And that is good advice to any woman that's good-looking that's being underestimated at a table full of people in the men's world, women and men. It doesn't matter, because now we've taken a lot of that out of the workplace. And if you want to dress and look beautiful and sit and listen and show your power in a very positive way, in a way that's humble but powerful.

How did Elaine Culotti's experience in a military household impact her life?

How did your approach and the way that you've navigated throughout your career, how did that really come full circle and impact the way that you approach things on the [Undercover Billionaire]?

I was pretty young when I was trying to understand my dad's military career because I grew up in a military household. We traveled everywhere. My dad was gone all the time, fighting for our freedom in this country and incredible. Our armed service is the most important thing we have. It's just incredible, so incredible. And I went on this trip, I went on the USS Theodore Roosevelt aircraft carrier. I got to fly out and spend time on this boat. It's a two-night overnight stay. It's limited to very lucky, lucky people. And when I was there, I watched a small city floating in our ocean that could be out there for 20 years, and the only thing they need is food and gas for other people that come aboard.

And I was in the captain's office and on the wall was many, many plaques and many accolades of great service and achievement. It was all plastered. And there sat these baseball sticks and the baseball sticks had a little slogan on the top and they were all signed by famous baseball players. And it said, "Walk quietly and carry a big stick. Walk quietly and carry a big stick." And I thought, "Gosh, that's so manly." And then I thought about it and I thought about it. And I thought about it. And the big stick is not to... It's not that. That's not what it's about. It's about, "Keep your mouth shut and listen and learn because the more you put in there, the more powerful you are when you say something and you have to say something." And so I've tried to observe when I'm learning and speak when I'm teaching.

It starts at a really young age to listen, just with your child, just to say, "This is the routine that we need to follow." It's not because you have to keep yourself in a routine. But if you can teach a child a routine, then they have more time to learn because they know what they're supposed to be doing. 

What was Elaine Culotti's favorite part of production?

I'll circle back a little bit to the show. I want to know what your favorite part of the production experience was and what it was like working with such a major network for the first time.

My favorite part of the show has not happened yet. It's going to come up. The most important takeaway for me was the value in building a second family. I have not, in my whole career, really relied on a group of people like I relied on them. And it's because I didn't have to. I've always been the one that people rely on. I'm always the one that has to write the checks. I'm always the one that has to come up with the ideas to do everything. And it just feels... You'll see as the show goes on.

And plus we had COVID, so we've got a whole team. We had people in our team that were terrified of COVID. We had people in our team that didn't care about it. So we have a lot of moments we had to sit down and say, "No, no, no, look, it's not about you. It's about them. They are scared. And we mustn't scare people." Right? It's doesn't matter. We're not talking about you for a minute. And gosh, the selfishness we have in our lives daily, it's overwhelming, really, sometimes that people don't understand it's not about themselves. It's not about you. And so I can't wait until the world gets to see this group of people harness all this energy and just become... We were unstoppable, literally unstoppable.

Elaine Culotti talks about accessibility in the internet age

I'd love to know how this is going to impact your work and your career moving forward now.

Certainly I'm going to spend a lot of time on my philanthropic love for farming and taking care of small farming and to helping small farming with supply chain. And encouraging people in the middle class to buy fresh farmed vegetables, because it's really left for high, high-end farm-to-table restaurants and for people that live under the poverty level that actually farm and eat their own food. The middle class doesn't see it, unless you go to a farmer's market and buy it every day. And generally, you're at a high-end mall because they use farming as a hook to get people to the mall. Or you're going to a big high-end, super expensive farm-to-table restaurant, and think about the amount of time and energy spent on the chef at that restaurant to have to go and seek this food out. Right? So it's very expensive. When really it should be less expensive and readily available to absolutely everybody. The problem is supply chain. We need to work on that. ... And my takeaway is 100 percent from this amazing experience at the Shepherd's Inn, farming, Fresno. Big box stores, the train, the small stores, the farmer's markets, the grocery stores all need to have small farmers present.

Accessibility is really... I think, that's what a lot of our problems boil down to.

If you think of the age of communication... I mean, look, when I was young, I had to go to the library and look things up and make up notes. To get to anything, you just Google it. My girlfriend, who's pregnant, the other day ... she was on YouTube trying to figure out how to change the seal on the bottom of her toilet, on YouTube in her bathroom. I'm like, "What are you doing?" She goes, "I can't get ahold of anybody. I don't want anybody in here." And she's got the toilet off.

So let's just think about that for a minute. So accessibility on the internet... What we need to do is make more educational television, and my hat is off to Discovery Network for doing this. They have made educational television. Our production company has made educational television. We need to make educational television, but we need to make it fast enough for the millennial. How are they going to be entertained, watch it, absorb it, rewind it, watch it again, take notes, remember, learn? How are we going to do that? We're going to put a grant and a name together. We're going to create this episodic, on the ground, learning with three different strategies, doing three different things in three different places. And we're going to create something that's a learning tool, three university classes in two hours that you're in fully entertained. I mean, you can have popcorn. It's very entertaining.

Elaine Culotti on getting people back to work amid the pandemic

You talked about that a little bit and how there are three of you, there's three different processes. Did you kind of see that as competition? Did that really motivate you to create this new business in such a short period of time? Or were you just so certain on the path that you were on, that you didn't really take it into account with the noise that was maybe going on around you?

My real estate background made me think about the most important thing and that is to increase the value of real estate. I can't get away from that. Right? That's my DNA. So whatever business you're in, if it's brick and mortar, right? You want to think about the highest and best use of the space. Brick and mortar, there's many businesses that will not go away as a result of the our electronic world. Right?

I know we're trying to sell groceries online and it's going okay. And people get them delivered and everything else, and you can probably get away with it. But there's nothing like going to pick something that's just been pulled out of the ground, or to catch your own fish. You can order a mattress online and you can lay down on it. But those big old mattress stores and laying on all those beds, it's kind of fun. You're not going to take shopping away from me. I like putting different clothes on and standing there and looking at it instead of ordering it online. I mean, I don't mind ordering it online if it's something utilitarian. I want to try a gown on. I want to smell perfume. I want to smell all of it. I love trying on makeup. What the heck? Sephora. The makeup people and like getting your makeup done. What the heck?

It's an experience. And it's such a sensory thing that I think so many of us are really craving right now.

So much so. So when I say that, "Did I know what I was going to do when I got there? No, gosh no." I did what I had to do. Business, money. These people needed to make money. I needed to get to a million dollar valuation in 90 days, with zero resources. It was a tall order. If I had to fix something, construction, whatever. The last thing I wanted to do was what I did. But at the end of the day, it's like, you have to get people back to work. Obviously, I could go online and try to sell something online. But what about this concept of American pride? What about all these people with all their businesses? I wanted to help small business. Food, feed you. Sleep, where do you sleep? Where do you shower? How clean are you? How clean is your food?

Elaine Culotti is determined to bring locally sourced products to consumers

The convenience of online has made a lot of us, maybe, a little out of touch with where all of our things, all of our food, all of our clothing, where it's all resourced from.

We don't know. We do not know. You do not know when you open up something that's been delivered to your door, how many hands were on it? It's a complete fallacy that we know. We don't know. We don't know in the grocery store. We don't know. It's critical we get our... Look, we couldn't have survived pandemic without Amazon. I'm very grateful to the teams that pivoted and the people that drove, all the delivery companies. Great, wonderful. But you're not going to take away a kiss from me. It is what it is. And it's just the most basic thing. But when you hug a friend, and kiss somebody, pick up a baby.

Elaine Culotti hints at her season of Undercover Billionaire

I would love to know if there are any spoilers or any teasers about your season that you can share a little early?

Well, I can tell you that I don't sell my truck. When I first left, I thought, "First thing I'm going to do is sell my truck." And for whatever reason, I don't sell the truck, and the truck is a nightmare. It becomes a big nightmare and I don't sell it. And I think it's like indicative of my nature of just like, "It's okay, it's going to run a little longer." I don't sell my truck. We're not allowed to say if we get there or die trying, and everything. But I can tell you this, that the team themselves are in Fresno, on what's called ShepsClub.com. And I encourage people to visit them. They have a membership available for any tips on farming and things about farming and deliveries local in Central Valley for California. But I encourage people to go on and see what these people are doing in a closed city. We didn't just have COVID, remember, we had the Yosemite Fires.

An entire community was devastated in the middle of all of it. And I mean, it was heartbreaking, absolutely heartbreaking. I can barely speak about it. It was so incredible. And the way that everybody banded together and stopped — with everything going on in their lives — to sort this out in this moment in time, is truly the most prideful part of American pride. Nobody was in trouble. Food was everywhere. Firefighters were taken care [of]. People stopped, they gathered what they could, and they drove and helped. Everything was dropped. Kids were in the back. "We need to go help." And it's not a spoiler alert. It's just so empowering to me how incredibly persevering Americans are. Californians, "Drop what you're doing right now, there's something more important." They prioritize.

What does Elaine Culotti want viewers to take away from Undercover Billionaire?

I have one final question for you. I know we touched on it a little bit about viewers being able to really learn from watching the show. But aside from that, what are you really hoping that viewers will take away from your season?

I would like very much that they would take away that the American pride concept is alive and well. And that we are an incredible nation. We are not divided. We are indivisible, it's in the pledge of allegiance. And see through the smoke, find the forest through the trees. Everyone should own a home. Everyone should have a job that they are not afraid they're going to lose every minute of the day. Everyone should start a business. Everybody should have security and feel safe and everyone should know what their superpower is. You know, it's very important to know what your existential value is. And I'm going to work on that, teaching people about, find who you are and what you can sell. Who are you? What do you do best? Because that is very different than money in the bank. That's money coming in. Right? Money in the bank's money in the bank. If you can't keep it or make more, it doesn't matter. It makes no difference what's in your checking account. It doesn't matter. Or your savings account. If you can't create more on you and your superpower, it makes no difference.

Undercover Billionaire is now streaming on discovery+.