It was spring break of my sophomore year of high school. There were no waves, and most of my friends had managed to get off our small island in the Pacific. With nothing else to do, I finally had time to piece together an idea for a website.
Now, this was 2002—still a year before WordPress launched and three years before the first video was uploaded to YouTube. That meant building a website wasn’t as straightforward as it is today. I spent endless hours figuring out how hosting worked and how to upload photos and videos. In the end, what I created barely qualified as a website by today’s standards. But the fact that my friends and I could now share surf videos and photos online was a crazy concept at the time.
Looking back, I had no idea of the internet’s potential or how powerful a tool it would become for communication. We were just kids having fun—kids with a lot of free time.
Fast forward 20+ years, and website platforms have evolved dramatically. For years, I used and recommended Squarespace as an easy solution for friends and clients needing a simple, well-designed website. And while it’s still a solid platform, I’ve come to realize it’s just not the right solution for the type of work I do now. So I made the switch—fully committing to building websites on HubSpot’s CMS.
This wasn’t a small decision (no website change should be), so let me explain why.
1. My Clients Need More Than Just a Website
Look, I’m a big fan of Squarespace for personal projects, portfolios, and businesses that just need a nice-looking website. But most of my clients need more than that—they need a website that directly connects to their marketing, sales, and customer engagement in a seamless way.
That’s where HubSpot’s CMS changes the game. Since most of my clients are already using HubSpot for their email marketing, CRM, and automation, it just makes sense for their website to be part of that same system. Instead of managing yet another platform and trying to integrate Squarespace with other tools, HubSpot lets everything work together natively.
Marketing, sales, customer relationships—it’s all in one place. No extra plugins, no third-party add-ons, and no disconnected tools.
2. I’m Spending Less Time Fixing & More Time Creating
One of the things I always loved about Squarespace was its simplicity. You don’t need to mess with code, and it looks great out of the box.
But over time, I found that simplicity came with limitations. When clients needed custom functionality, deeper integrations, or more flexibility, Squarespace often wasn’t enough. I’d end up working around platform limitations, using third-party tools, or telling clients, “Sorry, Squarespace just can’t do that.”
With HubSpot’s CMS, I don’t run into those walls. Their drag-and-drop builder is just as easy to use as Squarespace, but it comes with way more flexibility. Plus, because it’s built on a professional-grade platform, I never have to worry about downtime, security issues, or limitations.
I want to spend my time helping my clients grow, not troubleshooting platform restrictions.
3. Personalization is the Future of Websites
One of the biggest weaknesses of Squarespace is that every visitor sees the same website. But not every visitor is the same.
Think about it—if you run a nonprofit, you have different types of visitors:
• Major donors who don’t need to see a donation request
• First-time visitors who need to learn about your mission
• Volunteers who want to know how to get involved
With HubSpot’s CMS, I can create smart content that adapts based on who’s visiting the website. A first-time visitor might see an overview of the nonprofit, while a returning donor sees impact stories. This personalization is a game-changer—and something Squarespace simply can’t do.
Even for small businesses, this makes a huge difference. Imagine a coffee shop that runs a subscription service. A new visitor could see a call-to-action to sign up, while a returning subscriber gets recommendations for their next coffee order. The website actually works for you, instead of just being a static brochure.
Squarespace is great for what it does—but for growth-focused organizations & businesses, it simply falls short. I need a platform that helps my clients not just look good, but actually grow in how they communicate with their audience.
Thinking about upgrading your website? Let’s chat.