Rockland Page, owner of ROCKaBLOCK, LLC, is the kind of creative entrepreneur Indiana wants more of: talented, disciplined, original, and willing to bet on himself. He grew up in Indianapolis, built his design career in Chicago, and now spends his weeks in a downtown Indy shop trying to grow ROCKaBLOCK into something much bigger than a clothing brand. His wife and teenage daughter still live up north. He heads back on weekends. In between are the things that make creative entrepreneurship both exhilarating and brutal: client work, pitch decks, long drives, inconsistent cash flow, and a vision that keeps outgrowing the infrastructure around it.

On paper, Page has plenty going for him. He has worked in editorial design, built a respected apparel brand, won pitch competitions, landed notable clients, and developed Rock AR, an augmented reality platform that turns merchandise into a storytelling and analytics tool. The screen printing pays the bills. The apparel builds the brand. The technology points toward the future. But the capital required to scale that future remains stubbornly out of reach.

That tension is what makes his story worth paying attention to. Page is not an early-stage creative with a vague idea. He is years in, with traction, customers, and a working product. He is also navigating a reality familiar to many entrepreneurs: building while overextended, pitching through shifting expectations, and trying to raise money for something investors and institutions do not always know how to categorize. In Page’s case, that challenge is sharpened by the fact that he is a Black founder often having to translate both his vision and his market in rooms that are not prepared to understand either on their own terms.

What emerges is not a simple story about hustle or hardship, but a clearer picture of the gap many creative entrepreneurs are forced to navigate: between traction and sustainability, ambition and bandwidth, and public enthusiasm and meaningful support.

Polina Osherov: You’ve built enough that people know your name, but not enough so that you can coast. What does that in-between feel like?

Rockland Page: Chaos. You’re always hustling to stay in the spotlight or stay in front of people’s field of view. I might be able to rest for a couple days, but I’m always thinking about the next move. Always thinking about how am I going to get the next gig, how am I going to launch the next shirt. It’s just never-ending.

PO: What part of your business feels most like who you are, and what part feels like what you have to do to keep the whole thing alive?

RP: The creating and the selling feel most like me. When I can actually sit down and focus and make a design that I’ve been thinking about for weeks, months, and sometimes even years, and I finally get it done, I look at it, get it printed, and can wear it, that feels like a huge release of something I’ve been holding inside for a long time.

The part I hate the most is the paperwork, the business side of things. Trying to keep track of everything, trying to negotiate bills or rates or whatever else. I just can’t stand it. Pitch decks, raising money, it doesn’t feel like me. I know it’s a crucial part of what I’m building. It just feels like it’s turning corporate. But I know it’s inevitable. If I want to scale and grow the business, I have to adopt some corporate mentalities and structure. And that’s the hardest part, figuring out where that fine line is. I’m too artsy for one group and too business-like for another group, and it’s just like, where do I land?

PO: Has having one foot in art, one in business, and one in tech made you more valuable, or just harder for people to understand?

RP: I would hope it makes me more valuable. I definitely think what I’m building is valuable, and people are definitely starting to see more value in what I’m doing versus when I was out just looking for work, like a 9-to-5. Back then I would beg and plead and send resumes and fill out applications, do that whole process where it’s upload your resume, now fill out everything that’s already in your resume, and then you hear nothing. Months later you get a rejection letter from some job you forgot all about. That just feels like wasted effort.

At least now, if I’m building something or making a design or getting ready for an event, I have more of a direct line to the people, the intended audience. I have more control over what I do and what I say and how I can interact with people. But the downside is that it’s all on my shoulders. So on one hand I have more freedom and autonomy, but I’m also carrying the whole thing.

PO: When did you first feel like, okay, I’m onto something?

RP: I’ve had a few of those moments. Two really stand out. One was during the pandemic when I got contacted by ABC7 Chicago. They found my brand online and wanted to interview me live on air. That was the first time I was able to present what I was doing to a huge audience and speak from the heart and show people exactly what I was building. People still bring up that interview, and that was going on six years ago now. That was the first time I really felt seen.

The second was when I did my first pitch contest, the Purdue Northwest Big Sell Pitch Competition. I was pitching this idea of an augmented reality T-shirt that could come to life and teach Black history. During rehearsal I nailed it. During the actual event, I felt like I flubbed it. My demo didn’t work right. It was awkward. Because of COVID, I wasn’t even in front of judges. I was talking to a camera. Then they started announcing winners. Third place, not me. Second place, not me. I was about to walk out the door and they said, “This last guy did something pretty special. Rock, come on over here.” It really felt like a Miss America moment. I won $10,000 for an idea. I’d never really won anything significant before, especially in my professional career. After years of wanting validation through previous jobs, here I was striking out on my own and getting recognition for something. That was one of those moments where I thought, “I’m finally on the right track.”

PO: Give me the elevator pitch for Rock AR.

RP: How many times have you gone to a convention, seminar, or some event where there are all sorts of vendors and exhibitors passing out free swag? We all go around, grab the tote bags, the T-shirts, lanyards, cup cozies, whatever, because it’s free. Then after the event, you’re standing there with all this stuff wondering what you’re really going to do with it. Most people end up throwing it in the trash.

As an attendee, you’re overwhelmed by the sheer number of items you receive, but also unimpressed. You don’t really have any affiliation with the companies that gave them to you. On the flip side, the exhibitors have spent tens of thousands, if not hundreds of thousands of dollars to be at that event, and all they can say is, “Hey, we passed out 3,000 tote bags with our logo on them.” There’s no way to measure any deeper interaction.

So I began to wonder: could I take what I’m doing with AR technology and really cool design and incorporate it into these mundane promo items, museum gift items, concert swag, you name it, and give the client the ability to track who’s using their items? Every time the scan is interacted with, the item comes to life and interacts with you through your phone. Now I can get analytics. Someone might have gotten this item in Indianapolis, but now they’re in Texas or California or New York. Now I know someone on a Thursday afternoon on an iPhone 13 interacted with this promo item. I can change the messaging, and add a call to action. Now this item becomes a lead generation tool.

PO: What’s keeping this from being easier to scale?

RP: Funding. Manpower. This is growing beyond something I can do by myself. I’ve got volunteers in here now doing little things, and I’ll take every bit of help I can get. But bigger picture, I need someone with technical expertise who can help build the AR platform, and make it what it needs to be. That’s beyond my skillset. I know what I want it to do. I know how I want it to look. But I can’t get up under the hood and build it myself.

PO: But you do have your first customer, right?

RP: Yes. My first customer is the American Association of Nurse Anesthesiology, which is not who I would have expected. I’ve made two augmented reality enamel pins for them, and I’m working on a third. They’ve been with me through every iteration of the platform so far. They’ve been my guinea pigs and willing to grow with me. So I know if they’re willing to work with me and grow with me, there have to be other people out there. I’m not pitching a concept. I have an MVP, it just needs to be refined. That’s where I’m at now, that messy middle.

PO: You went through the gBeta Main Street program. Was that useful?

RP: Yeah. I got help with my pitch deck, my messaging, and how to speak to investors. It gave me more confidence. But the mentorship was probably the most valuable part. Just being able to talk things out with someone who’s familiar with the business ecosystem, versus calling one of your friends who tells you everything you do is good because they know you. I got constructive criticism, feedback, and even connections that helped me refine things. It would have been great to come out with some cash investment, but I still think it was worth going through the program.

PO: How much are you trying to raise, and how would you spend it?

RP: Half a million dollars. I’d be happy with a hundred thousand, but every time I say a smaller number, people act like that won’t be enough. So If I raised half a million, I’d give myself a salary, and then the rest would go into product development, building the platform, doing trade shows, travel, marketing, and getting in front of the ideal customer. Rock AR isn’t for someone who just wants to make a single T-shirt for their grandma. This is for Coca-Cola or Pepsi or a university or a sports organization that wants to reach tens of thousands of people at one time. It’s going to take money to go out and meet them and give us 12 to 18 months of runway to build out this platform.

PO: Have you found that the challenge is not just getting people excited about the idea, but getting them to see it outside their usual template of what a scalable company looks like?

RP: Yeah, I think that’s a big part of it. Most of the feedback is, “Great product, great passion,” but then it still comes back to, “Can you show it another way? Can you make it feel broader?” I’ve been in pitch meetings where I’m showing something with Marcus Garvey or Harriet Tubman, and people are like, “Oh, this would be great for Taylor Swift.” So sometimes it feels like they have to run it through a more familiar template before they can fully see it. And that’s been part of the challenge — helping people understand that I’m not just pitching a T-shirt. I’m building a platform.

PO: Have you had to become a different person to keep doing this?

RP: I think so. Especially in the last couple years, I’ve had to become a part-time parent because I live two hours away and I’m away for most of the week. I see my family on the weekends. That’s taxing. Not being able to pick up my kid from school or drop her off or make her lunch. I’m very much a nomad right now, couch surfing and moving around. But I do see the fruits of my labor. I just got a call from the National Museum of African American Music in Nashville. I submitted some designs that I want to make for them. So it’s upfront work, and unfortunately there are things I can’t necessarily do from home.

This whole thing has also forced me to think higher of myself. A lot of times in my career, maybe even in my upbringing, being in the Midwest and growing up in a church environment, it’s like you don’t want to boast, you don’t want to brag, you just keep your head down and be humble. I think there’s a way to do that without shrinking. I’ve had to learn how to tell people what I’m capable of and be proud of the work I’m doing. You might not believe it, but I was actually a very shy person for a very long time. If I spoke, you could barely hear me. So entrepreneurship has been a net positive, even though it’s been really hard. Every day I’m tempted to quit ROCKaBLOCK at least once. But then I remember all the things I’ve accomplished and what I’m fighting for, and I’m compelled to keep going.

PO: What does it take to keep going?

RP: You’ve got to be partially delusional. Dedicated and delusional. Even when all the data says no, you say, I’m going to be that one that does it different. That’s a big part of what I do. I try to live up to my name. Rock. I’m stubborn. I’m going to keep pressing on until either they’re going to break or I’m going to break.

I feel like one day the people who slept on me are going to look up and see a celebrity wearing this, or see it in some national institution, or on TV or TikTok, and they’re going to remember. I’ve already had little versions of that happen, where somebody that wasn’t serious about what I was doing comes back later and says, “Hey, I’ve seen everything you’re doing. I want to revisit this.”

So yeah, I’m still pressing on.

Follow ROCKaBLOCK on Instagram, or visit their website.

This story was made possible thanks to the generous support of our friends at Life in Indy.