Leaving the Safe Option Behind: Nick Ippolito on the Risk of Going All In
Location: Nelson, New Zealand
Started using Squarespace: 2014
Title: Co-Founder, SquareKicker
Nick Ippolito spent years bringing client sites to life with no-code tools, but eventually felt his hands were tied by technical limitations. Determined to turn his ideas into reality, he learned to code—and identified a shared pain point among designers in the process. To bridge that gap, he and his wife Hannah went all in on SquareKicker, a toolkit that helps designers level up their websites without writing code.
Now fully focused on product development, the Circle Platinum Partner and Community Leader stays close to the needs of the design community. In this interview, Nick discusses SquareKicker’s origin story, his favorite tools, and his advice for making bold business decisions that pay off.
What originally drew you to web development, and how did you get your start in the industry?
I’ve always been drawn to digital creativity. For a long time, coding genuinely scared me. I wanted to build beautiful visual experiences, but I didn’t want to learn a whole new language first. I spent years experimenting with new tools as they came out, always chasing ways to bring ideas to life without needing to touch code.
The truth is, I’m not only a verbal processor, but I’m also a visual processor. I need to create while I’m dreaming, so the idea stays alive. Out of frustration, a friend encouraged me to just learn how to code, because without it, I’d always hit limits with no-code tools. So I did, and finally pushed through that fear. Coding gave me the ability to turn ideas into reality. This gave me the confidence to go out into the world and offer my new skill set as a service.
But even then, something still bothered me. Visual design is only truly unlocked through visual creativity, not technical creativity. Designing with code felt like trying to paint with a stone. Sure, it’s possible, but it’s slower, more rigid, and it pulls your brain into a different mode. Instead of staying fully immersed in creativity, you’re constantly interrupted by the tooling, and that friction can stop some of the best ideas from ever making it into the world.
How did you discover Squarespace?
I discovered Squarespace while searching for a better way to build and sell websites for clients. I quickly realized something important: I wasn’t passionate about the deeply technical side of web development as a business. Spinning up servers, managing hosting, maintaining code updates, and constantly supporting ongoing technical changes for clients just wasn’t where my energy came alive.
I am a creative. I want to solve real problems with creative solutions that help entrepreneurs and business owners grow. The more clients I worked with, the clearer it became—most business owners don’t care what platform their website was built on. They only care that it looks great, works properly, and helps their business.
One of the biggest client needs was the ability to make website updates themselves. When you're running a business, you don’t have unlimited time, and having to learn a complex backend or message a designer every time you want a change becomes frustrating quickly and slows the business down.
That’s where Squarespace stood out immediately from every other platform.
It helped me create high-quality websites with purpose using visual creative tools, without worrying about servers, updates, or complex backend systems, and handing the site over to the client was effortless. No matter how custom I made a site, the handoff was always simple and painless, and everyone walked away happy.
What inspired you to build and sell design tools and templates?
I always refused to believe that building a website needed to be technical. After six years of building custom websites exclusively on Squarespace, I learned how far you could really push it. I could create almost anything I imagined. But I also realized not everyone wants to take the same path. Learning code takes time, and most designers want to stay in the creative flow, not get pulled into hours of troubleshooting just to make something look the way they pictured it.
That’s where SquareKicker began. The question was simple: what if designers could build anything without needing to code? Not by teaching code, and not by providing code snippets with instructions, but by making code invisible. The SquareKicker Pro Extension is a visual toolset with a familiar Squarespace feel that helps designers create complex layouts and animations with the same ease as designing. Building the Pro Extension was a unique solution to the challenges I’d grappled with for years as a designer—finally, here was the perfect blend of creativity, precision, and ease.
The next stage of the SquareKicker journey provided Squarespace designers with a completely bespoke way to deliver their custom designs. By building the first-ever end-to-end Squarespace template solution, creators could finally design websites exactly the way they envisioned using SquareKicker tools, and then sell their templates without the overhead of managing an inventory, sending template orders via email, or manually supporting every purchase. In turn, we made it possible for designers and business owners to start their projects with a collection of pre-designed pages and sections, ready to customize and use. But it wasn’t only about speed; it was also about creative freedom.
Templates can be downloaded and installed onto any new or existing Squarespace website, which means that customers can purchase a template and launch their site the very same day.
For us, it has never just been about tools or templates. It’s about empowering Squarespace designers to build better websites, run stronger businesses, and create a life they’re proud of through the work they love.
Which tool within the SquareKicker extension is a favorite? Which one is your personal favorite?
One of my favorite tools in the Pro Extension is a section tool called Fixed Scrolling. I kept seeing designers trying to figure out ways to make content stay fixed on the screen while scrolling, whether that was a fixed background image, or fixed content that stays locked in place.
People attempted some wild workarounds using complex JavaScript, but in the end, it mostly came down to creative thinking and understanding how Squarespace structures sections on a page. We realized we could solve the problem in a way that felt native to Squarespace.
The result was a feature that’s incredibly simple on the surface, but surprisingly powerful. With Fixed Scrolling, you can fix the position of either the content or the background of any section, without needing code.
But the most exciting part of this tool wasn’t planning it, building it, or even releasing it. It was being surprised by what became possible once it existed. As soon as we started experimenting and combining it with other sections and features, entirely new design ideas emerged, things we never would have imagined during product planning.
Back-to-back Fixed Scrolling sections layering on top of each other suddenly created a reveal effect, like pulling back a curtain. In other cases, it even felt like stop-motion animation, almost like a flip book. Those moments unlocked a whole new level of creative expression and showed us just how much imagination designers could tap into.
It genuinely felt like magic, and it wasn’t something we could have predicted at the start.
It’s moments like this that keep happening more and more often, when you suddenly realize what’s possible, and the product becomes bigger than what you originally imagined.
What advice do you have for web designers looking to level up client websites?
The best advice I can give is to invest time in upskilling. The more confident you become with creative tools, and the more you understand what’s possible, the more your client websites will stand out.
It’s the classic “slow down to speed up” mindset. Things might take a little longer at first while you’re figuring them out, but you’re building skills that stay in your toolkit forever. As that knowledge compounds, you don’t just get faster, you become far more capable, creative, and equipped to deliver premium work.
So treat each client website as a new challenge. Push yourself to try something you didn’t even know was possible. And if you hit a wall, send us an email with a feature request. We genuinely love solving real problems designers face, and building new tools that help you create anything you want.
At Circle Day 2025, you led a breakout session for in-person attendees where you discussed the importance of finding your business' “why.” What’s your why, and how did you find it?
For me, my “why” comes down to one simple belief: He Tāngata (it’s about people).
I believe people do their best work—and live their best lives—when they feel empowered, supported, and confident in what they’re building. That’s true for designers, for business owners, our team, and honestly for anyone trying to create something meaningful. My “why” is about helping people take bold creative steps, not just to build better websites, but to build a life they actually want to live.
I didn’t discover that overnight. I found it through my own journey.
When I started in 2014 as a Squarespace freelancer, I thought my work was simply about websites. But as I grew into running an agency, I realized clients didn’t just want a “nice site,” they wanted momentum. They wanted confidence. They wanted something that helped their business move forward, without feeling overwhelmed.
That insight became even clearer when we built SquareKicker. The deeper we went, the more we realized we weren’t really building design tools; we were removing the barriers that stop creative people from bringing their ideas to life. Squarespace was already a powerful platform, but designers kept running into the same friction points, and to push past them, you often had to learn code or spend hours troubleshooting.
That’s when our “why” became clear.
SquareKicker is our way of saying designers should be able to create anything they imagine, without needing to become developers to do it.
And I think I fully found my “why” during that pivotal moment of going all in, when Hannah, my wife and co-founder, and I decided to truly commit, not casually, not part-time, but fully. We did the business plans, the forecasts, the SWOT analysis, the second mortgage, the budget, all of it. But what anchored the decision wasn’t the spreadsheets and the pros and cons; it was clarity on the problem we were solving, and the people we were solving it for.
That’s why inside our company, we talk so often about the value of people. Because when you’re stuck on a decision, it’s usually not because you don’t know the options, it’s because you’ve lost touch with your purpose.
So I encourage everyone to slow down and start with their “why.”
During your session, you also spoke about bold business decisions. What’s a bold business decision you’ve made? What led to it, and how did you make that decision?
One of the boldest business decisions I’ve made was stepping away from client work and going all in on SquareKicker as a product.
At the time, agency work was the “safe” option. It was predictable; we knew how to deliver great websites, and it paid the bills. But we kept seeing the same thing again and again, designers trying to build more creative, advanced sites on Squarespace and running into limitations that forced them into workarounds, code, or compromises.
Eventually, it just became too obvious to ignore. This wasn’t one designer having a hard time; it was a real pain point across the whole community. And the opportunity felt way bigger than building another great site for one client. We could build tools that helped thousands of designers create better work.
The way we made the decision was a mix of being curious and courageous. Hannah and I did all the boring but essential business math, and we made sure we understood what the risk actually looked like. We also talked to people we trusted who had taken bold bets themselves—not just people with opinions.
But you never really know anything for certain. So, at some point, you stop trying to eliminate risk, and you just take the leap, backed by the best information you have, the right people around you, and a big dream that feels worth being a little foolish for.
What’s your favorite part about being a Circle partner?
I know I keep saying it, but it’s because it’s true: the best part about being a Circle partner is the people.
This community is honestly one of the biggest reasons we’re still so committed to Squarespace. The people in the Circle community don’t feel like “users” or ”customers” on the other side of the world, they feel like friends or colleagues, and some even feel like family. You jump into conversations, share ideas, solve problems, celebrate wins, and you actually enjoy it.
What I love most is that being a Circle partner keeps you close to real people and real pain points. You’re not guessing what designers need, you’re hearing it, seeing it, and building alongside them. And the more you help, the more empathy you build—for the designers, the businesses they’re supporting, and the work they’re trying to create. That sense of shared mission is addictive, and it's like a dopamine hit in the best way.
And then there’s the other side of it, Circle makes you feel closer to Squarespace too. Like you’re not just building on the platform, you’re part of helping shape where it goes next. It makes everything you do feel bigger than yourself, and, honestly, it gets me genuinely excited for the future.
Key takeaways
Here are the key insights from Nick’s interview:
The more time you invest in upskilling, the faster, more creative, and more capable you become as a designer
If a technical gap is limiting your creative output, push through the fear of learning that skill to bridge the divide between your ideas and reality
Challenge yourself to try something new with every client project
Experimenting with tools and combining features can unlock unexpected creative magic that strict planning often misses
Prioritize client autonomy by delivering websites that empower business owners to make updates without technical friction
Don't wait to eliminate every risk before making a bold move. Instead, gather good information, consult trusted peers, and take the leap
Want more?
Check out Squarespace Circle, Squarespace’s program for professional designers and web design agencies. Along with exclusive content, discounts, and other perks, Circle brings professionals together from across the globe to exchange advice while connecting with new clients and collaborators.
