Most tech entrepreneurs start out with a side-project. A project that scratches their own itch, that they build outside of their normal daily work. Sometimes these side projects are a way for an entrepreneur to cut their teeth, before moving on to the real deal. Other times the side project becomes the startup. Either way, side projects play an important role in the birth of an entrepreneur.

While many of you know about the first and only startup I founded, you may not know that I have a few side projects in my past. I am lucky to have a good friend, who I've known since high-school, that shares the same passions for entrepreneurship and technology. From around 2007 to 2010, Jeremiah and I worked on 3 different web applications, which overlapped each other for some period of time and earned more than 50k combined users in our best month.

One of those projects was called CitySpeek, and it was born out of a frustration that Jeremiah and I both had. In 2007, Twitter was just starting to gain notable usage after being launched in 2006. Jeremiah and I were both early adopters and saw a game-changer. Then, we started experiencing an imbalance of signal to noise. We had to deal with a lot of tweets we didn't care about, to read the ones we did care about. Going the other direction, we wanted to send out tweets to, say Portlanders, and not anyone else, because we knew that the content wouldn't be interesting to anyone outside of the selected region. In other words, we loved the concept of Twitter and wanted to improve it by offering rooms, or channels, where users could opt to view only the tweets about a subject or region they cared about. We also added image/video uploading (at the time, Twitter just linked to an image/video) and message translation (again, something Twitter didn't yet offer).

Now, with the popularity of chat programs for communications both at work and for communities outside of work, I am reminded of how CitySpeek foreshadowed the world we live today. Popular apps like Slack and Hipchat organize communities around channels or rooms. Public but contained spaces where people can discuss specific topics, without adding too much noise to the main stream of information. I'm a member of 4 Slack "teams" (there definition for a group/community/company), 2 of them being groups that represent a community of people that all come together to communicate in a central place. In the case of the PDX Startups Slack, just like we used to do on Twitter. Only now, instead of a single noisy stream of tweets, I can go to a specific channel in Slack, like the #product_management room, to talk only about product management, with people who also only want to talk about product management.

CitySpeek didn't take off. We had a whole bunch of problems, the least of which included being rookies at building, launching, and marketing web apps. That said, the experience building CitySpeek, along with ThePortlander.com (Community curated news aggregator for Portland, OR) and Goboz.com (a better Yelp), is what prepared me to start CPUsage, which while it ultimately failed, was a real company that allowed me to pursue my dreams. Its fun to fondly look back on the past and say "hey, I had a good idea! I may not have executed well on it, but it was a good idea, ahead of its time!"

What fun side-projects have you done? What did you learn? Glad you did it? Let me know over on Twitter or Facebook, using the social media buttons below!

Recently, I blogged about some products and services that I wish existed, things I'd pay for if they were available to me. One of those ideas seemed to be rather popular and many of you have the same problem: Too many communication and collaboration tools at work, and its hard to find the information you are looking for.

I was intrigued by all the interest in this idea, so I decided to dig in a bit more. Shortly after publishing the original blog post, I started a survey. I listed nearly 40 business communication, collaboration, and file storage tools. I simply asked for people to check a box next to all of the tools they use at work, and in a second question, tell me the top problem them have with these tools.

The results were fascinating! As of this writing, I've had 58 responses. There is a whole lot of data to sift through and make sense of, which I'll be doing over the next few weeks. That said, I've gotten started and wanted to share what I have learned so far.

Before i jump into it, please note that I am not a professional pollster, nor am I a data scientists. The data I present is likely tainted in a variety of ways, and I am sure that the questions and answer options could have been better presented. One way the survey and data are tainted is that I advertised my survey through my networks on Twitter, Facebook, LinkedIn, and an industry Slack channel. Thats a whole lot of built in bias! So, you get what I am saying? Good.

The Apps

There are some clear winners and losers when it comes to the apps you use at work. For starters, 85% of respondents use a chat app, and 75% of those people use Slack. I knew that Slack was hugely popular, but I had no idea it was that pervasive among my network. I also figured that other apps like MS Communicator/Lync and Gtalk were lightly used, but I had no idea that Hipchat would be such a small player at just 8% of chat users.

Something else interesting, but not surprising, is the popularity of Google. Gmail, Drive, and Hangouts all have better than 50% usage across the survey's respondents. The only Google product that doesn't fair well is Google Talk (Gtalk), with just 17% usage. I suspect that 3-5 years ago, Gtalk would have come in at between 25%-50%, capturing most of Gmails users. However, a few years back, Gogle released Hangouts and began to merge some of their communication tools. A bigger impact on Gtalk was probably the growing popularity of Hipchat and then Slack, which offer much better functionality.

Also popular is video conferencing software, with 83% of you using some sort of tool in the category. Google Hangouts and Skype are the most popular, with every other option a distant 3rd. The least used type of software was in the Customer Service/Sales category (as defined by me), with only 33% of respondents using one of them (Salesforce, Zendesk, etc). Also unpopular is the collaboration category, with tools such as Quip, Jive, and Confluence (again, defined by me). Only 48% of you use a tool like this. A surprise, based on my quick view of the data in the above graphic, was project management tools (Asana, Trello, JIRA...my definition). I expected that nearly no one was using these tools, but it appears that as a group, they are popular, with 60% of you using one or the other. Of course, the category is dominated by JIRA (49% of PM tool users) and Github (54% of PM tool users), which are both more about software development than they are general project management, so my organization of the data and integrity of the survey are likely playing an outsized role here.

Digging into the stats

What I was really excited to learn about was the usage trends and patterns beyond the individual apps. Do people use a lot of different apps? Do they use more than 1 app to accomplish the same thing? I was not disappointed!

For starters, respondents on average use 6.7 different communication and collaboration tools at work. The media is 7, which means half (29) use 7 or more apps! In fact, the respondent with the most apps used in their work was someone with 14 different apps. You use these apps across 4-5 different categories (4.7 mean, 5 media).

With a median of 7 apps across 5 categories, its clear that no only are people using many apps, they are frequently using multiple apps to accomplish the same thing. A vast majority of you are using multiple apps in at least 1 type of communication/collaboration tool category. Just 26% of you are using only 1 app for 1 type of communication/collaboration, across all categories, leaving the other 76% of us double-dipping in at least 1 category.

The most common category where people use multiple apps to accomplish the same thing is in the video conferencing space. The average is 1.7 different apps, with many of you using 3 (17%) and commonly 2 (39%). While that means that the most common was just 1 (44%), this is misleading because the majority of you actually use more than 1 (56%).

Of the 7 different types of apps we looked at, 67% of you use at software from at least 5 categories. Not a huge surprise is the 9% of you that use at least 1 tool across all 7 categories, its just not that common to have to communicate and collaborate in EVERY way possible. After all, certain tools like JIRA and Salesforce are focused at specific functions within an organization (software development and sales, respectively).

What sucks about communication & collaboration software

You'll recall that my second question asked what was wrong with the tools available to you. A whopping 62% of respondents (36) said there was something they didn't like about the tools available to them. Based on the content in those responses, I categorized them into 6 different types of problems: Too many, Distracting/Noisy, Compatibility issues, Usage levels, Finding things, Application quality.

The most common complain? Too many, said 58% of the feedback comments. The second most common problem, which turns out to be very tied to the first, was how hard it is to find things (33%). Many of you, 31%, said that getting usage was a big issue, either on-boarding to these tools or getting the right people, using the right tool for the job. I didn't expect 19% of respondents to have compatibility issues....apps not talking/syncing with each other. That one never occurred to me. Five people said that low quality apps were an issue (14%) and 17% said that noise and distraction were a problem, a number I thought would be much higher.

Since my analysis is part qualitative in addition to quantitative, here are a sampling of a few interesting comments:

“So many choices, what’s the right platform for the message at hand?”

“I have two sets that don’t work well together- Google tools vs. Microsoft. I have a Mac and the MS tools are uniformly terrible. Syncplicity is required, but is one of the worst drive applications I’ve ever seen.”

“Too many of them! Don’t know where to post information. Don’t know where to find information.”

“This information is shared in so many places. There isn’t one place where all the data lives.”

Interesting stuff! I'll continue to dive deeper into the data and report back as I make new discoveries. If you'd like to discuss my findings or get access to the raw data, drop me a note by using the contact form on this site, or mention me on social media!

The time I made a better Twitter and foreshadowed Slack

The data behind communication & collaboration apps at work