Almost one year ago I left my software development job at Amazon.com in order to pursue a more entrepreneurial life. If I were still at Amazon I'd currently be preparing for my annual review. This process involves comparing my achievements against my goals for the year, identifying things that I could do better, and setting goals for the upcoming year. This post is my annual review of my first year as an entrepreneur.

Goals

When I left Amazon, my plan was to spend about six months exploring potential business ideas, learning a bunch of new technologies that would be helpful for building web applications, and developing my personal network among Seattle's startup community.

After the first six months, my hope was that I would have found one or more projects that seemed like viable startup candidates. If I hadn't yet become fully engaged in my own startup at that point then I would also consider joining an existing startup or finding work as a consultant while continuing to experiment with my own ideas.

Achievements

Shortly after leaving Amazon I was presented with an opportunity to help out at TeachStreet. They were looking for someone to tackle some of the development tasks on their backlog and I was looking for an introduction to Seattle's startup scene. The time I spent there proved to be a really great transition for me and because they were really open about how everything worked I was able to gain valuable insight into the daily operation of a successful startup.

While working inside a large company I often felt that I lost sight of advancements in the outside world of software development. In order to regain this perspective, I wanted to begin attending conferences and events where I'd get a chance to meet developers with different backgrounds and hear about the challenges and opportunities that they encounter. In addition to getting to my first SXSW this year, I was also able to enjoy a couple of trips to SF and Boulder for conferences like TechCrunch Disrupt, GoGaRuCo, and Defrag.

I met developers from all over the world at these events and one thing that really became clear to me during these conversations is that software development is splitting in two directions: prototyping and building for scale. I'd had several opportunities to do the latter (everything at Amazon needs to be built for "web scale") but until this year I really didn't have much experience with the former.

In order to improve my prototyping skillset I also began regularly attending "rapid development" events (e.g. hackathons and Startup Weekends). I discovered that I really enjoy the process of delivering a working version of an idea during a compressed timeframe and I have a strong feeling that this ability will become increasingly important so one of my goals for the next year is to spend even more time honing these skills.

Hackathons are also significant to me because it was during a hackathon event that I built the first version of Kindlegraph. Although Kindlegraph began in much the same way as many of my other projects, for some reason I couldn't simply put it aside. As my six month self-imposed deadline approached, it became increasingly obvious that there was something compelling about the Kindlegraph product as more and more authors continued to sign-up for the service and promote it to their readers.

I've now incorporated a business (To the Reader, Inc.) around the general idea of building software for e-books and e-readers and I'm actively working on Kindlegraph as the first product.

Areas for Improvement

Now that I'm running a new business, I basically need to learn everything there is to know about running a business. As an example, I haven't yet found a great way to manage all of the things that I need to do and as a result I'm constantly shuffling my priority list (although I don't know if that is always a bad thing).

Another thing that is really difficult for me is asking for help. It's not that I'm too proud but rather that I don't want to bother other people with (what will certainly appear to them as) trivial and inconsequential challenges. However, I recognize that in order to be successful I will not be able to do it by myself and so over the next year I'm going to make a dedicated effort to enlist the help of others.

Summary

I feel like I'm still just getting started on the entrepreneurial path but I'm pleased with what I've accomplished this year. I continue to be encouraged by all of the opportunity that I see around me and I'm really focused on making progress everyday.

The best way I can describe the transition from working for a large company to becoming an entrepreneur is that when I worked for someone else, I sometimes wished the days were shorter. As an entrepreneur, I always wish they were longer.

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'Fast' is the most overused adjective in startups today and it has been used to describe just about everything that startups do: move fast, fail fast, hire fast, fire fast, get big fast, etc.

Speed by itself is a fine quality but in the context of startups "fast" really means "go fast all the time". Unfortunately, all that speed comes at a tremendous cost. I'm proposing that "constant high-energy activity" isn't the most desirable quality for startups. In fact, it's opposite (laziness) is actually much more preferable.

Let's start by observing nature and specifically those animals that sit on top of the food chain. These animals (e.g. lions) all share the same qualities: predatory, strong, fast. However, the animals at the top of the food chain are also among the laziest in the entire animal kingdom. They understand that their survival depends on their ability to conserve energy until they spot an opportunity to kill. Only then do they transition into an extremely high-energy state and relentlessly pursue their prey.

What does this mean for startups? Don't spend any more energy than is absolutely necessary. Especially don't fritter away energy doing things that have no impact on customers just because that's what startups are expected to do. For example, raising money, overengineering infrastructure, and writing too much code in advance of customer feedback are all things that many startups think they should be doing but can consume great amounts of energy and distract from things that actually matter to customers.

The problem with doing anything fast is that speed isn't free. Spending massive amounts of energy just to go fast when the objective isn't clear means that you won't be able to accelerate when your prey is in sight. True predators understand that their energy levels are finite and failing to catch their prey just leaves them that much more exhausted and close to starvation.

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For years I've heard amazing stories about Startup Weekend but I've never been able to attend because they always seemed to be scheduled on weekends when I had previous engagements (like the birth of my son). This past weekend I finally had the opportunity to participate in a Startup Weekend event in Seattle and I was not disappointed. The organizers were fantastic, Madrona Venture Group were wonderful hosts and the attendees were all top notch people. In the end, my team and I built a platform for community sorted data called Crowdsort.me and we were awarded first prize for the weekend.

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The most effective investment strategy is a highly undiversified portfolio when you are right.

Jim Collins, “Good to Great”

Individual investors are told that the way to accumulate wealth is by continually making small investments into a variety of assets. This strategy is called diversification and basically it increases wealth by reducing risk.

As an entrepreneur, the resources that I can invest are my time and my ability to build. Shouldn’t I also invest these resources in a diversified manner?

The most often told tale of entrepreneurial success begins with an entrepreneur identifying a single problem to solve and pouring all of his energy into a solution for that problem. The entrepreneur executes extremely well on his vision and is fortunate to tap into a great demand. When his endeavor begins to show traction the entrepreneur “doubles down” on his investment by allowing other people to invest their time and money into his project as well. This doubling down occurs several more times until the entrepreneur has built something of tremendous value and in the process has amassed a sizable personal fortune.

The truth about these tales of entrepreneurial success is that they are quite uncommon. They are cases of being invested in a highly undiversifed portfolio and being exactly right.

The investing analogy for this type of successful entrepreneur is the investor who bets all of his money on a single stock. As the stock shows initial strong performance the investor borrows additional money so that he can invest yet more into that stock. Fortunately he has identified one of the best performing stocks of the decade and is rewarded with tremendous wealth.

I believe that the entrepreneurial folklore is actually harmful to entrepreneurs and causes them to chase the uncommon success. If an entrepreneur is interested in amassing a large amount of wealth then the most likely way of obtaining that is by investing his time as if it were his money and doing so consistently over a long period of time.

This is the strategy that I’ve chosen to follow. That is, I’m making many small investments in a large number of projects and I’m constantly “rebalancing” my portfolio by spending my time on those projects that are most deserving of attention.

Assuming that each of my projects is self-sustaining and that I retain complete control over each of them, I have unlimited runway to let each of them grow and develop naturally. Of course in any portfolio there will be winners and losers but I’m betting that my collection of projects will grow to be more valuable than any single one of them might have been had I invested all of my resources into it.

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When I started this blog I gave it the title "ReadWriteHack" to reflect my goal of learning something new everyday through reading, writing and/or hacking and this blog has reflected that goal up to now. In this post, however, I wanted to write about my other daily goals that are not intellectual in nature.

Part of the reason I don't explicitly mention these other goals in this blog more often is that (like any habit good or bad) they've already become part of my daily routine and so I need to spend less mental energy making sure I do them everyday. Together with my "intellectual development" goals they contribute to my overall goal of maintaining a healthy lifestyle.

It probably goes without saying that the three most important habits of a physically healthy lifestyle are eating well, exercising, and getting enough sleep. Even though everyone knows this, it is just so easy to let one or more of these slip until you discover that you are physically and mentally exhausted and you have no choice but to shutdown until you recover.

Thankfully, my parents instilled my brother and I with healthy lifestyle habits from an early age. Good nutrition and daily exercise were routine for us and (combined with a good set of genes) the result is that I've never had a problem with my weight.

The last but perhaps most important daily habit for me is to spend lots of time with my family. This is essential to my emotional well-being and therefore to my overall health. It's also the reason that I could never take a job where I was away from them often or for long periods of time.

P.S. Since I left Amazon I've been helping with some software development work at TeachStreet. If you want to learn more about developing healthy lifestyle habits you should check out one of their many fitness classes and/or nutrition classes.

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"If this is the biggest mistake you ever make, then you will not have lived a very full life."

Therefore, one way I can measure progress in my life is by looking at my mistakes. If I can see that they are getting continually bigger then I can use that as a way to tell that I am taking greater risks and living a potentially more fulfilling life.

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Problems with Twitter search
Twitter search is one tool designed to help solve this problem but it is currently very basic as it only supports a default "most recent" sort for the results from a specific query. There are usually lots of low value tweets in this result set as the only requirement for a tweet to make the list was having been recently sent.

It seems that Twitter needs a better way to help the best tweets bubble up to the surface. I'm proposing that the way to accomplish this is to assign each tweet a value.

Just as a web page can be assigned a score so that Google can return the top match for a query it will become increasingly important for tweets to have scores so that people can find the most valuable tweet(s) on a topic. In other words, what is the equivalent of "page rank" for Twitter?

Implications of a tweet's value
The implications of being able to determine a tweet's value are powerful and include the following:

1. Tweet search can sort tweets for any term on value, not just timeliness.
2. A user can see any other user's most valuable tweets to help decide whether or not to follow.
3. Digests can be created to summarize the most valuable tweets for a given topic or a given time period.
4. Spam should get filtered out since it would have a very low value.

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Messages have lots of context
Services that receive messages on Twitter need to be able to parse the message for meaningful context and perform one or more actions based upon the content of the message. The more specific the service, the more specific the message needs to be. For example, search.twitter.com is a service which listens to every message and indexes the content of every message so that it is searchable. 'Trends' is a service built on top of this index that notices which terms are experiencing accelerations.

Message syntax conventions
It's not too difficult to extrapolate the growing usage of Twitter as a 'universal' messaging platform as certain conventions become widespread (e.g. beginning a message with a twitter id means a "reply", using a '#' symbol in front of a term indicates a tag) and new conventions are adopted. It is not too hard to imagine how even something like the unix pipe symbol ('|') might be utilized in Twitter to string messages along (e.g. "@nwa nyc tues am | @cal @bob 2pm") might use a service from Northwest Airlines to schedule a flight for you on Tuesday morning. Northwest might then pass the result of their service (perhaps a confirmation code, flight number and time) to the next service in line -- a calendar. That service would add the flight info to your calendar as well as send an invitation to @bob to meet at 2pm on that day.

Conclusion
Twitter's popularity growth has certainly benefited from people using it as a way to pass messages among themselves but the service will become indispensable as more people discover useful services which can be invoked by a simple message yet which can perform powerful actions on the user's behalf.

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