Chasing Innovation, Part 2: Empowering a new era of personal productivity


You know the type: Always making lists. And lists of lists. And random notes to add to lists.

(It’s me, guilty.) Maybe it’s you too?

Today, we can open any one of thousands of different productivity apps on our phones, from Todoist and Trello to Asana and Smartsheet. We can manage our to-dos and collaborate on them with anyone from anywhere.

But 15 years ago—in the age before smartphones and easily accessible Wi-Fi—that wasn’t the case.

And I wanted to change that.

In this second installment of the Chasing Innovation blog series, I’ll explore insights and experiences gained from my journey in the mid-2000s innovating on a fast-emerging trend in personal productivity—powered by rapid advancements in how we were building for the web.

Old friendships, new ideas

By early 2006, it had been a year since I’d left Peppercoin, the early-stage startup that set out to disrupt the payments industry. (Missed my first post in the series about it? Catch up here.)

I was at a boutique digital design agency in Boston doing frontend development for local clients like Gillette, the Red Sox, and the MBTA. It was steady work at a steady shop.

Then one day, the phone rang. 

On the other end was one of my former Peppercoin colleagues. He had been the tech lead at the company and part of the original “rat pack” that brought the first iteration of the platform to market. 

Now, he was approaching me with an idea for a new productivity app, gubb—and he wanted me to be a part of it.

The rise of GTD: When productivity became personal

The idea for gubb was simple: enable users to share and collaborate on lists together, in real time. This may sound quaint in hindsight, but it was an innovative concept at the time. After all, this was 2006—the iPhone would not even launch for another year.

My colleague had identified a need for a fresh take on personal productivity tools in the market. There were many contributing factors coming into play—ones that were creating a huge window of opportunity.

Three years prior, David Allen had published his now iconic book on time management and productivity, “Getting Things Done: The Art of Stress-Free Productivity.” In it, he outlined his methodology for Getting Things Done—or GTD as it’s commonly referred to.

The basic premise of Allen’s methodology was to build a system of workflows that would enable us to move all the ideas and projects we had floating in our heads externally. This could be done by recording them and then systematically breaking them down into actionable items we could work against. As Allen wrote, “there is an inverse relationship between things on your mind and those things getting done.”

In the years since its publication, GTD had amassed a cult following. It was now becoming increasingly popular, and the task management system was rapidly being adopted in the American workplace. Everyone loved “getting things done.” Soon, Allen’s ideas started spawning a slew of “life hacks” and applications built upon his concepts.

And this personal productivity craze is what gubb sought to capitalize on.

The web grows up

At this time, the web development world was in the throes of a new era. Google had tipped the proverbial domino with its launch of Gmail on April 1st, 2004. Over the following two years, it also ushered in Google Calendar (just two weeks after Gmail’s launch) and Google Maps.

Google was at the forefront of this new “web as a platform” movement—or Web 2.0 as it is better known. Google opened the doors for a plethora of new web-based apps that would soon become ubiquitous with how we use the web today.

What was making all of this possible was the rapid advancement of certain web development techniques developers were deploying to create applications directly within the web browser. This was predominantly supported by a web technology that would soon be referred to as Ajax, a term coined by renowned UX thought leader Jesse James Garrett in 2005.

While Google was leading the charge by deploying standards-compliant, cross-browser Ajax with each of its product launches, companies like helped boost its adoption for large-scale web applications. Another player quickly emerging was 37signals.

37signals was founded as a web design company back in 1999. After years of developing and launching sites for its clients, the company realized it needed a better tool for project management. In 2003 they started building out specific tools they needed to get the job done: message boards, to-do lists, and milestone tracking.

This suite of tools would eventually be released to the public as Basecamp in 2004.

37signals was also the pioneer of another major advancement for web development. At the same time they were strategizing what their new product would do, they were also creating a revolutionary new code base upon which the new web-based application would run.

This was Ruby on Rails, a rapid web development framework. With an emphasis on developer productivity, it allowed developers to start with full-stack web applications they could then configure with a broad set of customizable tools and settings.

The ability to run applications directly in the web browser using Ajax—together with the rapid development capabilities of the Ruby on Rails framework—was a powerful combination. 

While there was a clear product/market fit for gubb, it was how we planned to harness these new advancements in web technology that presented us with the opportunity to go toe-to-toe with the big hitters in the productivity software space.

Standing out from the crowd

With gubb we sought to differentiate ourselves from what others were putting into the market by creating a tool that was intuitive, accessible from anywhere, and truly enjoyable to use.

My colleague focused on building out a powerful set of product features that would enable our users to create, manage, share, and access their lists. At the same time, I tackled imagining a product experience that would tap into how people really made and used their lists

We netted out with a solid foundation for what would be released as an Alpha to friends and family in August 2006. But it was our continued user testing and market research that guided us to what would eventually become the public Beta we released in early 2005.

Through our research, we learned that—while list-making was the preferred method for people to manage their productivity—it was also a very personal and unique experience from person to person. 

These insights led us to theme our user experience around how people were using lists in the real world, using the “sticky notes” paradigm

  • Allowing users to group, stack, and “fold up” these sticky notes as they each went through their natural progression of completion
  • Providing a highly customizable workspace as the base for users to add their lists to 
  • Adding micro-interactions to enhance the positive psychological effect that writing things down and then, one-by-one, crossing them out has on people

Pushing boundaries

On the backend, we looked to push the boundaries of what mobile technology could do at the time. Our goal was to enable users to access shared lists at any time, from anywhere—and view the most up-to-date version. 

While mobile web browsing was available on the latest and greatest mobile phones at the time—lookin’ at you, Motorola RAZR—it wasn’t necessarily accessible. The limited access and speeds of wireless networks kept consumer adoption low. While we did build a version of gubb specifically for the mobile browser experience, we knew that—other than voice calls—SMS was the lowest common denominator in mobile communication across all phones and networks.

That’s why SMS became the foundation for what we called our multimodal experience. Leveraging the underlying technology of SMS, we enabled lists to be accessed bi-directionally. This meant users could access and add to their lists in real time by simply sending a text message—something they were already doing countless times a day.

We achieved this through a creative, albeit unusual, hack: email. 

Each new list created was given a unique email address that the user could use to access or add items to by sending an email with the subject line of GET or ADD (with the item details in the message body). Since mobile phones had the capability of sending a text to an email address, we were able to give users the ability to use this feature by text. 

We looked to push this concept and mimic the ubiquity of making lists by leveraging technology further. By integrating with voice SMS services such as Pinger, users were able to call the service, state which contact (i.e., which list) they wished to send a message to, and then speak a command (e.g., “GET”) to retrieve or add items to one of their lists.

We had a solid product with a web-based interface getting early praise from tech bloggers and users alike—and backend technology that was now giving users the power to access their lists on the go. 

Now we just needed to figure out how to make it profitable. How hard could that be?

Creating an exit strategy

From the outset, we had decided to keep the platform free, opting to monetize the platform through targeted marketing and contextual advertising. Once we had reached the right critical mass of users, my colleague and another business partner started looking for the most logical sponsorship partnerships.

While 2006 had been the year of building, testing, iterating, and proving the need for (and value in) what we had created, the next year was all about selling. 

I moved into a support role, providing the tools needed to pitch and demo the gubb platform to prospective partnerships. While list-making has a broad demographic—literally everyone makes lists—we focused on market segments such as trip planners, teachers, and brides-to-be.

They must have done dozens of pitches throughout the start of 2007, slowly building a core base of advertising partners for the platform. Soon it became time for us to move on to phase two of our exit strategy: getting acquired.

Things started well. In the summer of 2007, we were in talks with a major pay-TV network that had extended its brand into a growing digital platform. List making was a perfect fit for their demographic, and the integration of the gubb platform piqued their interest. 

While in the final stages of negotiations though, they were acquired by another major network. With that, their interest in gubb ended.

The rise of the iPhone and its impact

We soldiered on with our search to be acquired, and we were close to selling our underlying technology to one of the pioneering early internet-era tech companies. But because we had not evolved the core platform for so long, what once differentiated us soon became obsolete in the ever-advancing space of smartphone technology.

While we were pounding the street with our SMS-powered solution, Apple launched the first version of the iPhone on June 29, 2007.

Apple soon stole the smartphone market and, in doing so, put the web in everyone’s pocket. A year later, Apple released the App Store. Suddenly, “there’s an App for that” became the rallying cry of a new generation of entrepreneurs. 

Sadly, gubb was not part of that crowd. By late 2008 we hung up our gloves. We kept the platform running and continued to bring on new users, but we shut things down as a business.

Early-stage startups can be rewarding and heartbreaking at the same time. But being part of gubb stoked my entrepreneurial spirit and planted the seeds for pushing the boundaries of where emerging technology could take us as I moved into the next phase of my career.

If I had to boil my three years at gubb into three takeaways, I would say:

  • Don’t be afraid of going up against the established players: Standing on the shoulders of giants can enable you to enter the market more quickly.
  • How users use your product can be your differentiator: It’s not always about filling the need—sometimes, it can really be more about how you fill it.
  • If you’re going to pivot, do it early: The launch of the iPhone gave us an opportunity to pivot and focus on native app development. 

My three-year journey with gubb took me from quickly taking an idea to a product beloved by its users and eventually seeking to make it a business. Of course, any worthwhile journey will have its challenges and lessons.

By nature, entrepreneurs are innovators. They’re disruptors. But sometimes, innovation is less about original ideas—and more about original combinations. And at gubb it was a combination of applying user-centric design practices with emerging technology that enabled us to establish our unique position in the market.