Brief note to let my dear readers know that we’ve set up a blog for RescueTime. Right not it’s not that active, but will eventually contain lots of interesting things that we can learn from our anonymous users. By asking them a few questions, we’ll be able to look at how productivity differs by gender, age, industry, and more.

For now, we’ll tide you over with a long-n-wordy case study on our permissions marketing campaign and a link to my appearance on Dave Mason’s syndicated radio show. Good fun!

How many people can say they’ve been involved with 3 different businesses that have been featured on TechCrunch? First Jobby coverage (featured a second time when Jobster bought us), then Jobster coverage, and now RescueTime coverage!

RescueTime is the little side project I’ve been working on with my friends Robby and Joe. It was an idea that Joe and I started chatting about almost a year ago and we’ve been dabbling in on weekends from time to time since then.

Anyhoo, check out the coverage. It’s not quite same for a project like this, but it’s still pretty gratifying!

In the midst of house hunting in the Seattle area, I somehow have managed to launch a little marketing site for RescueTime (my current side project). It shows a few screenshots, answers a few questions, and allows folks to sign up to hear about it when we launch (via a quick-n-dirty PHP script).

I’d love to hear from folks about their thoughts on the site. Is the messaging clear?

I feel like we web geeks need to be constantly aware of the “curse of knowledge” we have about our own industry and the products we create.

The idea of the “curse of knowledge” as it relates to web geeks is one of the most compelling ideas I heard at SXSW, in a presentation by the authors of “Made to Stick“. I’m going to quote Harley Stagner, who has the distinction of being the #1 google result for the query “tappers and listeners”. Congrats Harley!

They told the story of Elizabeth Newton, who in 1990 earned her Ph. D. with an experiment involving “tappers” and “listeners”. In this experiment the “tappers” received a list of well-known songs that they had to tap out on a table to the “listeners”. The “listener” had to guess the song being “tapped.” Out of 120 songs only 2.5% were guessed correctly. What made this noteworthy was the fact that the “tappers” were also required to guess how often the “listeners” would guess a song correctly. The “tappers” guessed 50% when the reality was 2.5%. Why such a huge margin of error? The “tappers” had what the Heaths referred to as the “Curse of Knowledge.” When they “tapped” a tune it was impossible for them to tap it without hearing it in their head. Their prior knowledge of the song title made it impossible for them to imagine the “listener” having no such knowledge.

That 47.5% discrepency is the best damned illustration of the curse of knowledge that I’ve ever seen.

Sometimes I feel like even the best web UI designers are busily tapping away, confident that the users they are building for are “hearing” the same song that’s in their heads.

Anyhoo, if you get a chance, check out the RescueTime site and tell me what song you’re hearing.

About 8 months ago, a software idea hit me that I really wanted to work on. Like all ideas, it was based on a hypothesis. In this case, the hypothesis was “if understanding how you spent your time was braindead easy, you’d be a lot thoughtful about how you spent (and often wasted) your time.”

Unlike a lot of ideas, the feature-set required to test this hypothesis was simple enough that I (with a few friends) could set about to build it without interfering with my day job. So we did (should launch in beta form sometime in May).

One of the concerns as we moved forward was the perception that the executive team at Jobster (my employer) would have. Was I giving up on Jobster? Was I hedging my bets trying to participate in two startups at once? Would I cut-and-run the instant my side project took off? The answer is to these questions was an unqualified “no”, but I wasn’t sure I could count on the rest of the senior management team to feel the same way.

As I started being more aware of these concerns, I began to see that a lot of our heaviest-hittin’ technologists had projects on the side. Phil Bogle, our CTO, is the mastermind behind Beyond411. Morgan Schweers, one of our esteemed coders, has an ebay auction monitoring and sniping tool that has a dedicated following. Mark Swardstrom (though he recently left the company), works on a rails content management system in his off-time.

So, are side projects like these (and mine) a bad thing from an employers perspective? Absolutely not. Here are half a dozen from-the-hip-thoughts:

• It flexes muscles you probably don’t use much. Oftentimes, the larger your company, the more specialized your role. Coders spend all day coding. Worse yet, they often spend all day coding using a very small set of technologies. Have a side project and all of a sudden you are using a MUCH bigger toolbox. And, if your side project has aspirations of revenue, you all of a sudden start thinking about…. (wait for it)…. Business. Marketing. Sales. Design. While I think specialists are incredibly valuable, having a passing understanding of the tasks and challenges that other folks on your team face will make you better at what you do.
• It allows you to play with some bleeding edge stuff (if you want). You can try out technologies, interface ideas, and more without the risk you’d have in a more established company/product. You might just stumble onto something that would be valuable in the “real world”.
• It adds to your “shelf life” as an employee by keeping you from burning out. Seems counterintuitive, but it’s the truth. Web geeks love technology. When they go home, they futz with technology. If they don’t have a side-project of some flavor (ANY flavor, really), they will futz with the same stuff they futz with at work. Work on ANY project/technology for 14 hours a day and you’ll burn out quicker. Work on something new/different when you get home, and it keeps you fresh. Of course, ideally, people would find a different hobby, get some exercise, spend time with other people, etc…
• Side projects almost never “make it”. They almost never turn into a full-time job. Starting a company is extraordinarily difficult, and success is rare. Stats vary, but only about 20% of first time businesses last 5 years or more. This chance gets pretty close to ZERO when the founder is only working on it on off-hours. Most realistic people aren’t aiming for the home run when they dive into side projects.
• It might make a little bit of money. This is great for the geek– extra money is always fun to play around with. It’s also great for the boss– the more financially comfortable someone is, the less likely they are to start entertaining job offers based simply on the payscale.

As web technologies become cheaper and faster to develop in, it’s only natural to see more and more ideas fall into the “we can pull this off in a few long weekends” category. It will be interesting to see how many web geeks dive in… And how their bosses react.

Urm, just read a great blog post by Seth Godin who managed to say the same thing I did in my previous post using only about 5% of the space. I guess that’s why he’s a published author! He writes a nice list of 15 ideas in a post entitled “The Realistic Entrepreneur’s Guide to Venture Capital“. I’ll snip-and-paste my favorite bits:

#3 – Investors want to invest in a project that’s tested. If you can’t make it work in the ’small’, why do you think it’ll work when it’s big?

#15 – The companies that VCs most want to invest in are the companies that don’t need their investment to survive.

To all of you folks out there hunting for VC, what do you think? You might think there are seed-stage investors out there who wouldn’t hold their investments to such high standards, but I’d wager that you’ll get MUCH better valuations if you satisfy these requirements.

I just re-read “Getting Real” over my most recent trip to New Zealand. If you’re not familiar with it (you should be), it’s 37Signal’s manifesto on making simple web software. They are simply fanatical about making software that is as simple as possible.

It’s delightfully amusing when someone counters with the inevitable response of, “Well, that’s just ridiculous. Simple doesn’t work for EVERYTHING. What about Fortune 500 Accounting Software?” Their response (I wish I could find it, but I couldn’t come up the search query to dig it up) is, rougly, “Then you shouldn’t solve that particular software problem. Go solve something else and leave the complex problems to some other schmuck.”

I *love* that.

When starting up a company, you truly have a choice of what problems you want to solve (other people aren’t so lucky). I wholeheartedly endorse the idea of solving simple problems (which allows you to stick to simple solutions).

I’ve recently been attending Seattle Tech Startups meetings, which has exposed me to lots of startups that are in various stages of their existence. With a few exceptions, most of them are looking for seed stage or Series A funding.

As I considered it, it occurred to me that solving a problem whose solution is dependent on outside funding is a choice as well.

Don’t get me wrong. Funding is valuable, and sometimes critical for success.

But starting a company is pretty much laying down a bet to test a theory. Maybe you’re betting that your formula can make a better search engine. Maybe you’re betting that users want to share video online. Maybe you’re betting that jobseekers want a better utility to help them with their job search. or maybe you think that there’s a small (but passionate) group of lifehackers out there who want a time management tool. Regardless of what problem you are solving, you are betting your time and your money that you have some sort of secret sauce that allow you to build a business. Unfortunately, you can seldom test your theory without adding some “fuel” to your new company’s tank (in the form of time and money).

I’m constantly astounded by the people who seek funding before they’ve managed to test their initial theory by building and launching the absolute simplest feature-set that would solve the problem they are hoping to solve. The side effects of going after funding too early seem downright painful:

• It’s a huge time sink. You have to write and iterate on a business plan. You have to deliver countless dog-and-pony shows. You have to deal with lawyers. All of these things distract you from executing on your idea.
• Without at least some demonstration that your users/customers are responding positively to your solution, you are long odds for an investor. Even a proven team has a 70% of outright failure, and only a tiny chance at tremendous success. Chances are, an investor is not going to be eager to give you particularly favorable terms if all you have is an theory that you’d like test out. Conversely, if you can show even the slightest growth and can hand your investor a pile of emails from people who are excited about your offering, his odds for a good return on his investment just went up.

I totally recognize that building your idea and vetting it with a small userbase (acquired through word-of-mouth or some clever guerrilla marketing) isn’t always easy. I also recognize that bootstrapping can be painful. And, of course there are a lot of ideas that cost a pile of money before you can ever know if they are any good (for example, if I thought I could run a cable tv company better than Comcast, I might need a few dollars to lay down the fiber).

But, the more I hear stories of crappy term sheets and overbearing VCs, the more I feel compelled to limit myself to ideas that are simple (a la 37Signals) and cheap.

[edit: a friend of mine mentioned that his initial response to this post was that cheap ideas weren't defensible. If you can build the idea without significant capital, what's to stop the next guy from doing the same thing? I'd offer two responses to this. First, I'm only saying that it should be cheap to TEST YOUR THEORY. The person who wins in a given space is often the guy who builds the better business. Once you've tested your theory, you'd better be willing to dive in with both feet (and more money, if necessary) to make it happen. Second, just because an idea can be easily duplicated doesn't mean that the business can. Digg was built in a weekend-- exactly how easy would it be to knock them out of their position of relative dominance?]

I’m a huge fan of tagging as a means to organize data. It’s powerful and flexible– and it oftentimes has some pretty exciting social ramifications.

If you aren’t familiar with tagging (and you want to be), you could get up to speed fairly quickly by checking on the wikipedia entry on Folksonomy. If you’re more interested in insight rather than information, you should check out what Josh Porter has to say on the subject (Josh is hands-down one of the most insightful bloggers out there IMHO).

As a guy who built a web 2.0 resume posting doohickey (chock full of taggy goodness), I’ve put a ton of thought into tagging, specifically in the context of UI. So it was with great interest that I attended the SXSW panel entitled, “Tag, You’re It!”. The panelists consisted of a lot of impressive folks– George Oates from Flickr, Heath Row from DoubleClick, Ben Brown from Consumating.com, and Thomas Vander Wal (the guy who evidently coined the term “Folksonomy”).

The panel was interesting but like a lot of SXSW panels, the more you knew about the topic, the less interesting it was… But, I digress.

The most interesting moment (for me) was during the (very short) Q&A session. A person asked the question, “How do you deal with synonymous tags?” It was obvious that this was not an uncommon question– George Oates had a canned answer for that question…. “You don’t,” she said (yes, George is a girl). “It’s perfectly okay and wonderful that 3 people might tag a single data object in three different– but really similar– ways.” There it was, case closed.

The panel was wrapping up, but I wanted to shout, “Hey WAIT A MINUTE. That’s GOT to be wrong!”.

As I reflect on it, it turns out that there are (at least) two types of tagging– one of which is clearly a winner. The other (which is the type we applied at Jobby and currently are dabbling with at Jobster) is doomed to failure unless we get clever about how we pull it off.

Tagging where the Selfish Motivation is Organization

Flickr and Del.icio.us are the tagging poster-children. They are wonderfully simple– they provide a storage repository for big chunks of personal data (photos for Flickr and bookmarks for del.icio.us) and give you a powerful means to organize them. People oftentimes tag in radically different ways. Some people have dozens or hundreds of tags. Others have only a few. As George pointed out, people oftentimes tagged things with very similar tags. One person might tag a resource with “rockstar”, while another might tag it with “rock_star”, and a third might tag it with “rock-star”. This is fine with Flickr and Del.icio.us… With the service they offer, it’s most important to allow users to label their data in the way that makes sense to them.

The core functionality is organization, and the ability to search/browse/find similarly tagged objects is serendipitous. As a Flickr user or del.ico.us user, you really have no huge incentive to have your data be found by anyone else.

Tagging where the Selfish Motivation is Improved Findability

The only panelist whose userbase was largely concerned with findability was Ben Brown, of Consummating.org. Essentially, his site (recently sold to CNET) is a site where geeks come and tag themselves so they can get matched up with other geeks so they can fall in love and make lots of baby geeks, presumably. This is not unlike the tagging model that we used at Jobby (and currently use at Jobster). People labeling themselves to get found by other people.

This is where the tagging concept starts to break down a little bit. All of a sudden, it’s no longer important what tags you’d use to describe yourself– it’s a hell of a lot more important what tags people would use in a search to find someone like yourself. There are a few unfortunate byproducts of a system like this:

• You are incentivized to lie. The more desperate you are for a date/job interview, the more likely you are to lie. Why not tag yourself “slender”, even if you’re not? Might get your profile a few more views and one of the viewers might latch onto one of your other qualities. Why shouldn’t I tag myself “Ruby on Rails”, even if my experience with it is woefully limited? Maybe some manager out there will find my resume as a result of that tag and just maybe he’ll be wowed by something else he sees.
• You are incentivized to pour on the tags. The cost of adding a tag is very low, and every tag will increase the likelihood that my resume/profile will be viewed. This creates a lot of tag noise. Instead of having a nice and concise list/cloud of scannable tags, you can start seeing tag collections that are less than manageable. A smart coder will tag himself as “coder”, “programmer”, “developer”, “engineer”, “software developer”, “software engineer”, etc.
• Synonyms matter. A lot. Ben used an example of his perfect woman for a search… He did a search for a woman who was tagged “coffee” and “cigarettes” (ew). The problem with tagging in this model is that Ben’s search simply won’t find a woman who is tagged with “caffeine lover” or “smoker” or “chainsmoker” or “coffeelover”.
• People who are tagging data need to be smart about the psychology of searching, which they never will be. In the SEO biz, there are lots of tools (some of them very expensive) to allow a person to understand what people are searching for (to allow you to craft your content and meta-data to map to those search behaviors). People looking for a date or a job don’t have the time or money to figure out whether hiring managers are searching for “programmer” or “developer” more often. If the tagger is sophisticated enough to even consider this problem, he’ll probably (to be on the safe side) tag himself with both.

So, are you screwed if your service has tagging to enhance the findability of your users? I hope not. Here are a few strategies we’ve used at Jobby and Jobster to keep tags from getting “spammy”:

• Suggested tags. This is the best thing we did with Jobby and (unfortunately) it’s a feature that is really buried in the UI on Jobster. With Jobby, we essentially took what data we had on the user and presented tags that seemed likely to be of value to the user. So if a user tagged themselves “HTML”, we could fairly reliably say (given how often the two tags went hand in hand for other users) that they might want to tag themselves “CSS”. This also has a nice side-effect of giving your users the ability to tag themselves with a click rather than by typing all of their tags. And, of course, it encourages people to use the most popular iteration of a tag (using “CSS” instead of “cascading-style-sheets”, for example).
• Add scarcity to your model. At Jobby, we allowed user to assign a skill level to their tags (beginner, intermediate, advanced). There was functionally no limit to the number of tags, but it makes it a touch more difficult to lie. A lot of fledgling web geeks might be comfortable saying they know JavaScript, but a lot LESS comfortable saying they are JavaScript experts. At Jobster, I think we’ve provided a more elegant solution. Users are allowed to have up to 5 Superstar Tags– basically, these are the skills/areas that you feel you’re best at.
• Add REALLY SMART suggested tags within your search UI. We did this (in kind of a clunky way) with Jobby, and people LOVED it. With Jobster, we’re JUST starting to experiment with this, but I think it’s critical for tagging to work (when findability is the primary motivation for tagging). You’re search experience needs to be smart enough to present similar and/or related tags. Further, it needs to be smart enough to give the user a sense of the popularity of given tags.

I’m still waiting to see a site that really manages to nail the tagging/searching experience when the motivation isn’t just for personal organization. I’d love to hear more ideas on how this could be pulled off.