From freelancer to business alchemist: Omari Harebin on building a sustainable Squarespace business

Omari Harebin has been a fixture in the Squarespace community since 2012, and his journey from mechanical engineer to business mentor offers valuable lessons for designers and freelancers navigating today's uncertain market. In a recent conversation, Omari opened up about his evolution, the challenges of plateauing growth, and why authenticity matters more than perfection.

From engineering to Squarespace: An unexpected path

Omari’s professional journey began far from web design. After studying mechanical engineering and earning a graduate degree in marketing, he worked in corporate roles while pursuing creative projects on the side. The turning point came when he became a father.

"I made the decision to make the leap," Omari explained. "Squarespace kind of became what I leaped into because I had a Squarespace website on the side. I needed one for my creative portfolio."

Like many in the community, Omari’s entry into Squarespace design came organically. "Everyone else, you're doing your creative thing and someone sees it and they're like, 'Hey, can you make a website for me, too?'" he recalled. What started as throwing in websites as bonuses for photo and video clients evolved into a full-fledged business.

Building digital products through problem solving

After a year of freelancing, Omari was drawn to the promise of digital products as a path to freedom. In 2015, he began exploring Squarespace templates, though success didn't come immediately.

"It didn't get me there, not immediately at least, but it did give me a launchpad of really building up a pattern of finding problems where there was urgent demand and just solving those and allowing those to lead me to the product," Omari shared.

His approach centered on identifying problems rather than executing technical solutions himself. "My core skill set was finding the stuff, not necessarily executing," he explained. Partnering with developers who could execute allowed him to focus on marketing, bringing his career full circle to what he originally wanted to do.

Navigating more than a decade on Squarespace

Having built his first Squarespace website in 2012, Omari has witnessed significant platform evolution. He emphasized understanding what he calls "founder DNA" to grasp the heart of the platform.

"Squarespace's founder and CEO, the company has been going on since 2004. And I think in order to really understand the heart of a company, you have to understand the drive and motivations that got it off the ground," Omari noted.

He sees Squarespace's evolution toward supporting professional designers as inevitable. "I think it was only a matter of time," he said about the platform's recent investment in pro tools. "We, this community, has literally grown because problems exist. We wouldn't have businesses, most of us, if Squarespace didn't have limitations."

The shift toward professional designers and AI

Omari views the rise of AI as creating clear differentiation between DIY users and professional designers. "The DIY user is now going to be served by AI. I think that's just plain and simple," he explained. "It brings value back to the human contribution."

While AI website builders can create functional sites, Omari sees designers providing something AI cannot: true customization and human insight. His recent UPMarket report highlighted bigger budget Squarespace projects, signaling growing enterprise adoption.

Weathering market plateaus and economic shifts

After years of consistent growth from 2020-2022, Omari experienced what many businesses faced: a plateau in 2023-2024. His response offers guidance for others in similar situations.

"When I got to the end I'm like this is interesting because it's plateaued meaning that even though I was doing stuff what was the impact of that," Omari reflected. "I think I've been very aware that there are market forces that are much bigger than myself."

He compared his growth to catching a wave: "My surfboard happened to be out there to catch the wave. So now the same thing. It's like, all right, well, what's the next wave?"

Three pillars for enduring business success

Omari’s framework for sustainable business centers on three elements: truth, love, and value.

"Anchor that positioning in who you really are and what you're really devoted to," he advised. "If you deviate from that, then you're faking it to make it. And I know a lot of people think that's a good idea, but you just make it being fake."

The love component comes from genuine passion for solving problems. "Knowing you, Nick (Ippolito), I know that you literally love making the impossible possible. Because you light up so much every time you talk about it. And that devotion gives your business an enduring quality."

Finally, value emerges from where that devotion helps others. "Where does that devotion turn into value for someone else? How does it make someone else's life easier? How does it save them some money?" Omari asked.

Building assets through favors and goodwill

Omari shared that many of his most successful products began as favors for clients. "Every product or thing that I've done that has been worthwhile, it all started as a favor. It always started as something that came from the heart," he explained.

When a client appreciated his help sourcing RFPs and suggested others would pay for it, Omari turned it into a product. "I take that principle with me everywhere where the favor, a lot of what I've done over the past five years or six years, seven years, I haven't monetized. It's just from the good."

This approach builds what he calls "goodwill for the entire marketplace." By serving not just immediate clients but the broader community, businesses gain enduring quality.

The collaborative mindset: Rising tides lift all boats

Omari emphasized the interconnected nature of the Squarespace ecosystem. When asked about competition, he laughed and explained his perspective: "If SquareKicker does well, designers do well. If everyone does well then it rises the tide for everyone."

His advice for plateauing businesses centers on this collaborative approach: "How do I direct my energy so that I can help those businesses sustain and grow? How do I convert what I have, whatever that is, into a resource, into something of value that then allows them to keep going?"

"I don't exist without you. You don't exist without me. So, how do I make sure that we coexist together?" Omari emphasized.

Transitioning to coaching and mentoring

After nearly selling his business and going through due diligence, Omari had an epiphany. "It allowed me to kind of graduate in a way of being a true business owner where it's like, all right, I've created something that can be a transferable asset and something that I can walk away from."

Instead of walking away, he chose to pour himself back in differently. "Who am I now? I'm no longer the scrappy freelancer who's searching around for solutions. I'm the person who I wanted to be. So what does that mean? Well, it just means that now I can contribute in a much greater way across businesses as a consultant and as an adviser."

Omari now runs weekly group coaching calls every Monday, where designers can bring their business challenges. "What I'm always listening for and looking for are those hidden opportunities that are tucked inside your client work," he explained.

Embracing authenticity over perfection

When asked about design confessions, Omari reflected on taking himself too seriously for too long. "For a long time, I carried the expectations of perfectionism and wanting to do what I saw but couldn't do. I think a lot of people probably struggle with that where you see things that are just amazing and you're like, man, I wish I could do that, but you can't."

His advice: "Be honest about what you can do and what you can't do. And that will allow you to actually do more of what you can do as opposed to feeling insecure or insufficient or like I'm not good enough."

His recently revamped homepage reflects this philosophy—simple, honest, and direct about who he is and what he offers. "I'm still a DIY Squarespace user. I still hold that identity. I'm not a designer. I'm not a developer. I'm just turning myself inside out so the other Squarespace DIYers can get something out of it."

Staying grounded through family and play

Outside of work, Omari finds creativity and motivation through his three children, whom he homeschools. "My job with them is to play. So the more I'm immersed in their worlds and then when I come back out I feel fresh. I feel like okay cool I know what's important."

This perspective keeps him grounded in what truly matters while maintaining the sense of possibility essential for creative work.

Finding opportunity in every challenge

Throughout the conversation, one theme emerged consistently: opportunity exists within every problem and limitation. "The opportunity is always in the problem. The opportunity is inside the frustration. It's inside of the little that it feels like you have. But if you can take that little and break it apart, it now becomes two. And then if someone else takes it and breaks it apart, it becomes four."

For designers and freelancers navigating uncertain markets, Omari's decade-plus journey offers a blueprint: stay authentic, serve the community, look for hidden opportunities, and remember that sustainable success comes from genuine value creation rather than chasing trends or faking expertise.

As Omari put it simply: "Everything is better in the light."

To join Omari Harebin’s weekly group coaching calls or explore his resources for Squarespace businesses, visit sqspthemes.com.

Listen to the full episode. This conversation is from the Looks Good From Here podcast, where we dive past the shiny Instagram version of the internet to have real conversations with designers building real businesses.