HelpSpot Turns 20

Twenty years ago, I wrote "Whew, it's been a long 2 months or so" in my blog post announcing HelpSpot 1.0. Today, on October 24th, 2025, I'm sitting here thinking: whew, it's been a long 20 years.

October 24th, 2005 was my 29th birthday. I gave myself the gift of shipping HelpSpot that day. Today, on my 49th birthday, I'm looking back at two decades that have exceeded every hope and dream I had when I clicked that publish button.

That 29-year-old Ian would be stunned. He hoped to make enough to pay the bills and maybe hire a person or two. He couldn't have imagined the thousands of customers, the amazing team members who've been part of this journey, or that the little help desk app he was building would still be thriving 20 years later.

The Origin Story

Back in 2005, I was using an absolutely terrible help desk at work. It was mainframe-based and didn't even accept email. This was the reality for most companies then – either no help desk solution or something painfully inadequate. I knew there had to be something better.

So my wife and I made a decision that looking back seems both brave and completely insane. We'd just bought a condo that was a bit pricey for us. The dot-com bubble had burst not long before, so VC funding wasn't an option even if I'd wanted it (I didn't). We didn't have much savings.

We sold my car to fund the company.

I left my job, my wife kept working, and I started coding. Seven days a week, 10 hours a day, for six months straight. I only took a break at lunch to read a chapter of Harry Potter and then back to it. No frameworks existed – no Ruby on Rails, no Laravel. I didn't even know JavaScript, so I literally had a 4-inch thick JavaScript Bible next to me, learning as I built.

Here's the thing: with today's tools and frameworks, I could probably build that HelpSpot v1 in three weeks. But in 2005, it was six months of grinding or it wasn't going to happen. Those were the only options.

I'd been building in public the whole time, sharing my journey through blog posts and participating in the Joel on Software forums. Nine months before launch, I'd even written about designing the logo. By launch day, we had 80 people on our beta notification list. Not a huge number, even by 2005 standards.

Oh, and just to add to the pressure? We found out my wife was pregnant not long before launch. Nothing like a baby on the way to focus the mind on making your business work!

I formed UserScape as the company behind HelpSpot. Back then, it wasn't as common to have the company and product with different names, but it's worked out well over the years as UserScape has dabbled in other ventures. HelpSpot was always the main focus, but having that separation gave us flexibility.

From the beginning, we did things differently. We've been fully remote for all 20 years – starting with Campfire for chat, then HipChat, then Slack. This was way before "remote work" was even a term people used.

The technical evolution has been wild to watch. We started with no version control at all (I know, I know), then moved to Perforce, then CVS, and finally Git. Between all those systems and some data loss from the early days, I can't give you an exact count, but we've shipped around 450 releases over 20 years.

HelpSpot itself has transformed from 100% hand-coded PHP with no framework to being built on Laravel, and we're now transitioning the front end to Livewire. We started as on-premise only software, then added SaaS. Today about 25% of our customers still run HelpSpot on their own servers, which is pretty remarkable in 2025.

The People Who Made It Possible

The Team

Over 20 years, we've had 11 full-time employees. Many I'm still close friends with today. HelpSpot became a launching pad for incredible careers – both for those who stayed in the industry and those who moved on to other adventures. Watching people grow and succeed both inside the company and out has been one of the most rewarding parts of this journey.

The Customers

We've had thousands of customers over these 20 years. Some of our earliest customers are still with us – companies that started using HelpSpot in 2005, several years before the iPhone launched! Think about that for a second. They've stuck with us through the rise of smartphones, social media, cloud computing, and now AI.

The internet was smaller in 2005-2008, and HelpSpot crossed paths with some incredible companies. We were Twitter's first help desk. Basecamp used us. Our v2 redesign was done by MetaLab, who went on to design the initial version of Slack. It was an amazing time to be building on the web.

Even today, we work with companies moving from no solution beyond email to HelpSpot. The core problem we set out to solve in 2005 still exists.

The Rock at the Center of It All

I need to dedicate special space here to my wife. She's not inherently a risk-taker, but she took a chance on this crazy idea. We sold our car. I left my job. She supported us through those early months.

In the beginning, she did it all – testing, marketing, documentation, and CFO duties. She's been the absolute rock of our family and the business for 20 years. Through every up and down, every late night, every stressful decision, she's been there.

None of this would have been possible without her. I mean that literally. Not just the emotional support (though that was huge), but the actual work, the financial management, the voice of reason when I needed it. Twenty years later, I'm more grateful to her than ever.

Building More Than a Business

HelpSpot is older than my oldest kid – he's 19 now. We have three amazing children: 19, 15, and 12. The opportunities HelpSpot has provided us to raise our family the way we wanted, to travel and see the world together, to be present for the important moments – it's been more than I ever dreamed when I was coding away on those twin 14" Samsung monitors back in 2005.

While HelpSpot was never a hands-off lifestyle business, it's provided my family with a better life than I could have ever hoped for. We've been profitable from month one – every single month for 20 years. That consistency has given us the freedom to make decisions based on what's right for our customers and our family.

Looking Forward

Twenty years in, the fundamentals haven't changed: teams want to provide great support to their customers. That's still what drives us.

The rise of AI has created new opportunities and new challenges. But one thing that's become clear a few years into the AI revolution is that there's still incredible value in providing personalized, human support. If anything, as more interactions become automated, the human touches become more valuable, not less.

I'm excited to continue developing and evolving HelpSpot. We're still innovating, still solving problems, still serving our customers. The tools are better, the landscape has changed, but the mission remains the same.

Thank You

To our employees over the years – thank you for believing in this vision and helping build something special.

To our customers – especially those still with us from 2005! – thank you for trusting us with something as important as your customer relationships.

To the web development community – thank you for the support, the feedback, and the friendships.

To my family – thank you for everything. The sacrifices, the support, the joy you bring to this journey.

Twenty years ago, on my 29th birthday, I hit publish on HelpSpot 1.0 and wrote about trying to "just enjoy this one moment."

Today, on my 49th birthday, I'm enjoying 20 years worth of moments. Here's to the next 20.