Phin Barnes at SneakerheadVC asks whether you can boil decision-making down to a single question. It’s an interesting theory as the question he comes up with is, “Does this help us own more complexity for our customer?”

Every process or task (in enterprise or consumer) has a certain level of complexity — and the most valuable companies are able to attack very complex problems, hide the complexity from the customer and let them accomplish the task in a simple, straight forward way.

This single question lens is the same way I look at which products I use, for example. I want to know that all my photos are in iPhoto, all my events and tasks in Calendar, all my music in iTunes. I don’t want to think long and hard about where to put things. I was saving these Phin Barnes-types of articles, once upon a time, to Evernote but realized that some were in Evernote and some were in Instapaper and some were referenced here on the blog. Instead I started writing every day, referencing all of these articles here at eliainsider.com.

Back to Phin, this is a very interesting lens in which to look at decision-making. We are confronted with so much information that having a single question to analyze something is so much easier to remember and apply. I love it when complex issues can be boiled down like this.

Yesterday, if you were living in a cave, was the Superbowl. What interests me so much is how the National Football League became the NFL. The reality is that television and the rise of the NFL came at the same time, and football, as Seth Godin talked about in his post yesterday, was made for tv. In fact it is pretty clear that if it wasn’t for television the NFL specifically and football in general probably would not be as great as it is today.

Serendipity, luck, perfect timing. These are such important factors to get any business off the ground. Twitter was launched, in essence, at South by Southwest conference six years ago. It just so happened that SXSW was the perfect storm for Twitter: lots of people together who didn’t really know each other all looking for the hottest place to be. Twitter, with its indirect connection model, was perfect for that time and place.

Sometimes this timing doesn’t work out. It was the year before Twitter launched when we were on the verge of changing math education forever, except a fateful decision by Palm to stop making handhelds and abandon the education market killed the entire deal.

Yes, a company needs a good product. Yes, it needs to have all the pieces in place to take advantage of this timing. But the perfect storm of success needs to happen too. Rovio took years to have success and finally found it with Angry Birds on iPhone. Before the iPhone there was barely a casual gaming market. It’s rise made Rovio, as we know it today, possible.

Dropbox, too, owes its meteoric success to the small screen, or more exactly to multiple screens. Ten years ago most of us didn’t need Dropbox. We had a single computer and all of our files were there. In a world where we carry three or even four machines, though, keeping files on all of them, up-to-date, is critical. Dropbox launched at the perfect time.

This is why fortitude is so important. The ability to endure hardship, the pain that is believing in something even when the world is laughing, is critical. Serendipity happens. Being there at the right time with the right product is a huge part of success.

Glenn Reid wrote a post last week on working with Steve Jobs. I find these articles fascinating. A little insight into the way he worked. One of my favorite portions:

Not only did [Jobs] know and love product engineering, it’s all he really wanted to do. He told me once that part of the reason he wanted to be CEO was so that nobody could tell him that he wasn’t allowed to participate in the nitty-gritty of product design.

When Infinity Softworks started it was real small. There were three of us. Soon, though, everyone left and I was doing it myself. My goals were to prove to myself I could write commercial-quality code and manage the development process. I also was excited to do marketing, sales, customer support. I wanted to do it all. I figured it was the fastest way to figure out what I enjoyed and what I wanted to specialize in.

At some point, I added more people and we decided to raise a round of funding. Rather then embracing what I was good at and getting help for the rest, I moved on to the next experience: raising money, managing people. I left running the business to those I brought on board. As you might expect, the company went sideways.

Giving up everything led me to understand that what I really loved to do was product. I loved the design aspects, thinking through how customers work with them, refining and improving them. The mistake I made was not learning, in those first few years, what I was really good at and understanding what I needed to do to build a successful business. I understand that better now. I understand, as we consider a growth plan again after all these years of treading water, that in order for Infinity Softworks to be successful, I can’t turn over complete control of the company to those who come on board. I can’t imagine giving up the product vision again.

My mistake 12 years ago was thinking adding more people meant I didn’t have to do as much. In some ways that’s true. Other people run those aspects of the business. I was no longer solely responsible for development, marketing, sales.

But in other ways that’s false. My job needed to move higher up the tree. Instead of digging around in the roots, I needed to be watching the landscape, making sure we could see the entire forest. It didn’t mean giving up the product. It meant making sure the entire team was working toward the same vision.

Adding more people doesn’t mean less work. I understand now it means I do even more.

I always wondered about this: if your service is designed to be most valuable with multiple people then how do you get the first ones? The quintessential example is the telephone. Doesn’t do any good if only one person has a phone. The fax machine had the same problem. So did Twitter and Facebook.

Fred Wilson talked about this issue in relation to the bookmarking service delicious:

The first users of delicious were barely aware of and rarely used its social aspects. They just wanted to store their bookmarks in the cloud instead of in their browser. And they liked the tag based classification system. And they liked being able to use their links from any device. That was the single person utility delicious was built on.

But because bookmarks were public by default which resulted in most links being shared with others, a large social system developed. The delicious popular page was an important web destination in its day and most of those visitors never posted a link to delicious. They consumed others’ links.

As we’ve been working on new stuff here, we’ve wanted to make sure that it is social naturally. Sharing stuff, after all, is very human. But in order to get the first person to use it, it must also have utility for a single person. Or, as Fred puts it, social systems must have single user utility, too.