Laddering Up to a New Livelihood

we're going to Minneapolis to Jessica. She's a go getter, an eternal yes person, and a champion of the gig economy. Without a college degree, She's hopped around a lot of jobs over the years, trying to find what works for her, but never really settling down. And then, amidst the chaos of the pandemic, she had a thriving painting business kind of before she knew it. Um, I'm just gonna have you introduce yourself. Just say your name, who you are, what you do. I've really have done this for other

things that it's like the worst. I'm like so bad at it. I wasn't good in school. This is Jessica Rolling. She's thirty seven, lives in South Minneapolis. Whole job title like what you founder and CEO of pint. I'm still getting us to that new title. She is the CEO of her own company, Rolling Paint and All Women Paint Crew. It's probably hard for her to get used to that

title because it happened fast. She started painting houses just a few years ago, and now she's got an LLC employees, an amazing website, and to squash some of the misconceptions she gets about what she does. She is not a decorator. People have a vision. You are the person who comes in and executes the vision. Right, I'm setting up the actual process, the operation of painting your house. Okay, so

you never you never stopped people from making horrible color decisions. No, because first of all, you don't know you don't know what they like. Some people, I mean you, you can put up colors that you would never do and they just they love it. And that's that's what matters. I'm not living there they are. I want to tell you how much money it's going to be, and then I want to do that in that price and have you be happy about it. Each day at work for Jessica

can look very different. She's got four painters and a communications manager. Now that they're on a new job. We'll meet in the morning, talk over the project. The girls will start packing up the truck uh, and then well we'll call in the paint order. They head out to wherever the project is. Jessica make sure everyone's set up. Then I just read around like crazy and try to

try to knock things off my to do list. But to do list pretty much keeps growing, and they do wallpapering, rolling paints grew really fast and it's continuing to grow fast. So Jessica is currently in a transition period where she's setting her team up with everything they need to work without her on site. So I'm trying to step out of the day to day. So that's that's why it's so crazy. Right now, I won't have to be there to like go over the project every morning and talk

to the girls. I won't have to be on the project. We'd have all those systems set up where I can just go right to doing estimates or meeting with whoever networking. This moment of gross she's in after one of the most insane economic periods we've seen. Jessica has been in that mode for a while. She started on her own. She got too much work she brought help on. Then she got more work and had to bring more people on,

so on and so forth. It was building and I realized, like, it's going faster than I can Then I can do estimating and invoicing and all these other tasks. So before I realized I had a business, I had a business. So now I'm trying to build the business while owning a business. Jessica's a restless entrepreneur, she told me. Her mantra has generally been ready fire. Aim says she's always been that way, even when she was a kid. Absolutely, I'm actually a lot like my dad. I realized very social.

I know, like everyone on the black I knew everyone in every class. That's a big thing growing up in Minneapolis. She says, it's a big place, but everyone knows each other. And she loved that. I cared for it obviously because that's where that's like where my strengths were. We're connecting with people and knowing people, and so I guess I always knew that I was in this like rich city of connections. She had older brothers, had a lot of independence as a kid, played a lot of sports. It

was school that was tough. I hated school. You know, people have might have like mommy and daddy issues. I have like teacher issues. I liked going, I didn't mind, like I had friends, but I I just could not like the work was just so like I didn't understand why we were doing most of it. That might seem like par for the course for a young kid. It's not liking school, but it didn't go away. For Jessica. Middle school started to become a problem and the stress

was there. I mean, you know, you've been in a job that you've hated before and how it wears on you and your relationship ups breakdown outside of that way because you're you know, you're crabby. You're crabby all the time. It's taking all of your energy away from you, and everything else seems difficult. Eventually, she dropped out of public school. I just didn't show up. I didn't have a plan. I mean, it's crazy, Like looking back, I I realized, like,

oh my gosh, like what was I thinking? I wasn't I had like no future, I had no future plans. She did find an alternative high school that worked for and after high school, she traveled. She spent some time in London backpack around Europe and New Zealand and Australia. She'd come back and serve tables in the US for a bit just to make enough cash and then buying plane ticket. There was one, one, one moment when I realized,

like I wanted to stop doing that. So Jessica was backpacking, living the hostile life, and she had already been fantasizing about what it would be like to not put her name on food that she had in the fridge. And one day someone had stole ham that I I splurged on for like a sandwich because he eat a lot of like potatoes and beans, you know when you when you backpack, And I had splurged on like sliced ham for some sandwiches and someone stole it out of the fridge,

and I thought it was going to break me. So I was like, I think it's I think it's time, or and you thought I need to go home. Yeah, you know, like you go to put like something in like the toaster, and there's somebody else's food in there that had been left for like how long, and you're like, oh, I don't want to share a toaster anymore. After the ham incident, Jessica switched gears. She wanted to make some

real money. She didn't have much of a plant, but she knew that she wanted to eventually stop serving tables and that she had to be scrappy. I knew that people were not going to hire me because I don't have a college degree, and so I had to find places that we're going to listen to me, that I could get in front of and make them understand that I'm still a very capable employee. I knew I was

way better than what a degree could prove. So she worked for a lot of small businesses, and she dove headfirst into the gig economy, just doing lots of different jobs and getting in front of lots of different people. I wanted to find a career. I just didn't know what what it was going to be. So I think it was just it was finding out what's out there. She tried some corporate stuff, loved that there was a

lot of people, but couldn't do the bureaucracy. She worked as a p a organizing crazy things for Red Bull events, and she did keep serving tables on the side for a while. I mean, I was just doing whatever I could to make money and then the opportunities grew, but

not not enough to quite be full time. After a lot of years of piecing things together, she was working for a local real estate team as a transactions coordinator and somebody in the office had asked me to paint a couple of rooms for their client who had a an atrocious color on their walls and was reluctantly changing them to a realtor gray. The thing was, Jessica had

never done that before. The person who asked her just knew that Jessica's dad had a small construction business, so I think she just trusted that I was handy enough. So Jessica went to her dad and said, I've never done this. Should I do this? And He's like, well, yeah, of course, like why wouldn't you? And I'm like, oh, I don't know. He's like, somebody's like offering you work, you you take it, like not everyone gets that. We're not always offered things like that. So so yeah, I

did it. We'll be right back with Jessica's story after the break. A strong work ethic takes pride in a job well done, sweats over the details. This is you, but to get an honest day's work do you need a response, you need a call back, you need a job. Express Employment professionals can help because we understand what it takes to get a job. It takes more than just online searches to land a job. It takes someone who will identify your talents, a person invested in your success.

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Back to Jessica. She did her first painting job for the real estate agency, and then she got offered more, and each year they just kind of they multiplied. So I thought I'd have a few to go back to, but then it was like a few more than that, and then a few more than that in each season increased a little bit. She was doing other gigs this whole time too, because she didn't really see this as a full time thing. It took it took a long time, I think to to feel very confident in what I do.

I never advertised, or I didn't have a logo or an Instagram account or anything. I guess I'd still thought that I was going to be doing something else at some point. Even when she was getting consistent work and getting lots of jobs through word of mouth, she didn't see herself as a business. So it was just like making enough money so I can like go on vacations and eat out and drink or you know, just live my life. It was always still just a means to

an end. Yeah, you know. It was just like, how like I have enough money to make rent great, and then everything else is for you know, a plane ticket, running a solo business, setting the right rates, asking people for money. It was all a really big shift. But eventually she had enough word where she couldn't do it alone.

The first person who came on my team, I think that's when a lot of things clipped for me, is when you're explaining something to a new person and you can finally see the gap between beginner and where you are. You can see everything in between. Her first employee actually came on right as COVID started, and they were shut down for a couple of weeks, but then we're deemed

an essential service and got back to work. There were lots of homes being sold with the real estate agency and a lot of people stuck at home wanting to finally remodel. So pretty quickly she was bringing on more employees to keep up. So do you have a secret to growing more quickly? Yeah, I kept saying, yes, Yeah, it's really it. I just you know, I take things on there, like do you do this? Like, yeah, we do that, do you do this? Yeah, sure we do that.

They started doing wallpaper, going out of their comfort zone, and because Jessica knew everyone in town, all of the friends that she grew up with, were now buying homes and calling her, opening businesses and asking her to paint their new spaces. All this work was coming in and she was on site every single day. That was That was exhausting. That was probably the one of the hardest parts because our projects were moving so fast, and so to keep estimates going and do all that work and

invoice I mean, that was it was a lot. At what point did you accept that you had a business? I think at that point she had two women working for full time as contractors had more work than she can handle, so she started an LLC. I knew I needed structure. I knew that I wanted to keep these people. I knew that I wanted I wanted to get paid well, and I it was important that they got paid well to So I thought, Okay, we're doing this. We're going to build it. Let's build it right. Wow. Okay, so

you you just accidentally have a full fledged business. Now, Yes, it does feel accidental, It really does, though, But I know I've been working so hard, so it's nice to know that. It's nice to have something that represents your all, your hard work, which I think is our team. My team is fantastic, And just over a couple of years, Jessica now has four full time painters as employees and just hired a communications manager to run their web presence

and social media. So, as we heard in the beginning of the show, she's trying to get to a place where she can handle the business and not be on site every day doing a million things. You're in you're in growing pains phase. Yeah, I give it one more, one more year. This is the summer everything comes together. Really, Yeah, Jessica says sales have never been an issue since she started painting, and now that they've made a name for themselves,

they have a ton of return clients. They've still got more work than they could do even with the employees she has. Now that's because Jessica's always said yes, go go, go to everything, and now she's trying to decide how big she actually wants to be. I think we're I want to read it as we go. It's important to me that the people who are on my team now have careers, have job stability, and they can make enough money to buy homes and you know, have families if

they want go on vacations. So I want to make sure that we build it in a way that takes care of of who we have now. As a really professional, all women team, Rolling Paint has definitely stood out with clients. They stand out in the field because not all painting crews are as put together as they are. I think about that sometimes and I so you don't need any certification or license to paint, and would it be better

for the trade to to have that? Like probably, you mean, but getting into it, I mean for me, that was essential is the fact that I didn't have to have any formal training or work with another team, So I I I feel both ways about how how low that that bar is or the barrier for entry, and once you get into an industry like this, the sky is the limit with how far you can take it. Jessica

is proof of that. It's really a perfect place for someone like her who didn't fit in the traditional mold, is still go get her, thrives in the gig economy, but wants stability. It's good for people who need um quick turnaround on feeling the success of something. If you need people who need instant gratification, yeah, you're you're beginning, middle and end is you know, only like a couple of days away. Yeah, it's all there. I am one of those people, And to be honest, I relate to

Jessica a lot. I spent a while bopping around doing a hundred different things, restless, full of ideas, and eventually I did crave roots and stability because the hustle is exhausting. But even when I have settled down a little bit more, that restlessness is really really hard to shake, and I sometimes still feel that I'm faded to just keep moving all the time that like, I, oh, maybe I don't belong, like anywhere did you do? Did you ever feel that?

I guess being able to connect with people socially, I never felt like I was completely out of place, but I guess I didn't feel like I was finished, or I guess maybe I didn't dwell too much on on feeling like I didn't fit in because I hadn't even like sat there long enough to consider it. It was kind of like, well, this isn't serving me by, and

they're like, where did Jessica go? She laughed. I've always felt that it's kind of cool to be that person, kind of the wild card who gets stuff done, but you never know when they're coming or when they're going. But it really makes it hard to feel like you have a plan at all. Even now that Jessica is established, she's still feeling things out, you know, kind of a no plan plan. I told you I did not have a plan. I've never had a plan. Do you prefer that?

I don't think it's a preference thing. I think it's just how I'm built. I'm convinced that it's just that is just who I am. This is something new that she's come to accept this year while talking with a therapist, looking at who she is, why she's always been go, go go, and seeing it as a strength. You look back on everything you've ever done and you're like, oh, yeah, I've always been doing that. That's true. So I have traction.

I'm an activator. I start things um and that that can be seen as being a negative in your life. You know, so many people tell you that it's wrong or that you need to need to stop and think about it, and that's what they need it. That's not what I needed. I think I'm just one of many people who needs to hear this because there are just so any of us out there that don't fit perfectly into the way that things work. There's so many people who aren't built for regular school and tests or college.

So many people who don't want to work in one place for five days a week, or people who would rather work one job for a couple of years than half to the next because we're just curious. So many people who could never afford the absurd price tag of the degrees you need to get a quote good job, and there's a stigma against being one of those people. Seeing all those things as shortcomings. But those people are

forced to be hustlers because they don't fit in. They don't see things that work for them, so they start things, you know, And for people who can't start things like I'm essential, you know, that's that's I need to be doing this. I need to use what I'm good at for all of us, right, it's you know, we all have different different strengths and it's important that they vary. Like it's an ecosystem. We we need to be balanced

that way. As we wrap up this season, a big takeaway from me is just do what you want to do. Just do it works. If the last few years have proven anything, it's that there aren't many rules, nothing is certain, anything can happen, and the way things are done are not the way you need to do things. If Jessica and her business are a proof of anything, it's that if you are just relentlessly yourself, maybe, just maybe you'll

accidentally end up exactly where you want to be. And so to look back at everything I've ever done and knowing that that's who I've always been feels good. I don't have to feel ashamed for being the wrong kind of student or the wrong kind of employee you know. I just I wasn't in the right spaces for on the job. I'm otis gray. To see some of Jessica and her team's work, go to Roland Paint dot com m