Underpants -- ? -- Profit
The now famous business strategy from South Park.

I just finished reading Clayton Christensen's How Will You Measure Your Life. It was part of my recent resolution to branch out from the programming, startup, and business strategy stuff I spend most of my time reading. I surprised myself and really got a lot out of the book. In it, Clayton talked about forming a strategy for life, and executing on that strategy. And, he spoke in a language I could understand -- business. In particular, I really liked the way he framed life in terms of an emergent strategy early on, and a more deliberate one later.

Once you understand the concept of emergent and deliberate strategy, you'll know that if you've yet to find something that really works in your career, expecting to have a clear vision of where your life will take you is just wasting time. Even worse, it may actually close your mind to unexpected opportunities. You should be prepared to experiment with different opportunities, ready to pivot, and continue to adjust your strategy until you find what it is that both satisfies the hygiene factors and gives you all the motivators. Only then does a deliberate strategy make sense. When you get it right, you'll know.

Clayton is suggesting that our life strategy be more emergent than deliberate, until things seem to be working well, and then flip to be more deliberate than emergent. By emergent, he means that we should be exploring; taking advantage of unexpected opportunities. To put it in tech startup lingo, Clayton is telling us to keep pivoting until we find product/market fit, and then "go for it" with a deliberate strategy. And, just as importantly, failures should be thought of as experiments which show us what will not work.

My Goal: Wealth

My goal in life has been to become wealthy through success in business. It's been that way almost since I was 12 years old when I licensed out my paper routes through a sort of affiliate program I invented. But, why is my goal wealth? That seems kind of selfish.

Well, maybe it is selfish, but it goes deeper than that. From my perspective, a person who builds wealth through business success will gain influence, have more opportunities, and will have more of a voice in important matters. I want that. I want to make a dent on the universe, as arrogant and audacious as that sounds. Money sometimes corrupts, but it doesn't have to. As I argue below, wealth is not really money anyway.

Assessing my Strategy (My Life as a Case Study)

So, up to this point in my life, I've done pretty well with the emergent part of my strategy; I've taken advantage of plenty of unexpected opportunities. But, with wealth as my goal, I've made several critical mistakes, over and over, which have prevented me from reaching product/market fit, so to speak:

  1. Believing that if something is not working, that I can just work harder at it to get the desired result.
  2. Thinking that I could work hard now, at the expense of the rest of my life, and then ease back after succeeding.
  3. Far too often I've correlated wealth with money when making my pivots.

First, simply working harder is not a good way to succeed. Like most people who grow up in the United States, I have a cognitive bias towards working hard now for rewards later, which is rooted in our culture through the Protestant work ethic. Don't get me wrong, the ability and willingness to work hard is a good thing, for the most part, but when we are in the midst of an emergent strategy period in our lives, sticking with a bad direction and just working hard to somehow overcome it is not a good idea. I've heard it a million times: Work smarter, not harder. It's time I took the advice.

Intelligence is the ability to avoid doing work, yet getting the work done.

-- Linus Torvalds

And, somewhat related, I've always thought that I could put my head down and work really hard now, and then slow down in the future -- someday. More often that not, this means that I don't stay fit, my health suffers, I neglect my wife and kids, and my spiritual strength decays. I need to readjust my life so that the norm is regular fitness, spiritual strength building, improving the relationship with my wife, and doing everything I can to prepare my kids for their future.

But, for me, my most critical mistake, one that I've repeated over and over, is correlating wealth with money. Wealth is not money. Wealth is the gradual accumulation of assets which generate value; cash or otherwise. A wealthy person is one who has successfully used the value generated by assets, to purchase or create more assets, which generate more value. It's the quintessential snowball effect.

Even if I had succeeded in building and selling one of my earlier startups for millions of dollars, I wouldn't be wealthy. Only if I had built important skills and relationships, and put the money I made back to work on other projects, only then would I have become wealthy.

New (Deliberate) Strategy

I've gone through a long period of emergent strategy in my life. I've had success as an employee, at building a company, and also failed at building a few companies. In the last 6 months, I feel as though I've reached a sort of product/market fit for my life strategy, and my thinking is starting to become more deliberate. I've been comparing my strategy to the advice an investment advisor would give you: Take more risks early in life, then reduce your risk as you enter middle age, and finally remove risk and concentrate on income producing investments later in life.

Early in life I took several large risks by quitting some good jobs, and attempting to launch ambitious startup businesses. None of them succeeded, and now it's time to reduce my risk exposure.

So, there are three things I want to have going on in my professional life right now: 1) Reliable income that will help my wife and I save for a down payment on a new house while allowing me to 2) bootstrap an income business to support our family ($90k - $120k for us), and 3) get involved in a startup with relatively low time commitments.

Where the Pieces Fall Into Place

So, I just laid out some "yeah right, that's never going to happen" goals, but, because of my emergent strategy, they are mostly already here. I've put myself into a position to get lucky, and luck happened. This is why I say "you make your own luck". It's easy to create a list of goals when they've already fallen into your lap.

First, I've landed in a place where I can build great software products with an amazing group of people at MadGlory Interactive. Under normal circumstances I find it really difficult to build products that will become assets for other people when I'd rather be building my own stuff. MadGlory changed that for me. I get to work with a great team, that is not only super talented, but also great to work with, and get to work on exciting and challenging projects. I really enjoy it.

In fact it's been really difficult to avoid joining MadGlory as an employee/partner. I'm actually just a freelance contractor for them -- although a full time one. My stated goal is to build assets for my own future. As long as we are building products for other people at MadGlory, I'm not getting much closer to that goal. So, to stay true to my deliberate strategy, I can't join them full time, as much as I'd love to. (Side note: If they were bootstrapping a product, with a profit ASAP goal, I might change my tune -- see below.)

However, my time with MadGlory is really important to me right now. I'm having a great time doing what I love; building software. I enjoy my job, and I like the people I work with, which is super important. I'm also making a good chunk of money which will allow my wife and I to buy a house and move into the community that we want to be a part of. In addition to the financial boost, MadGlory also gives me a generous amount of scheduling flexibility so that I can work on other stuff important to my strategy.

I'm also still involved in a startup -- Pinfinity Books -- but I am not the founder or CEO, and I only own a small percentage of the company, so I'm not obligated to sacrifice 110% of my life for it. And, we are still searching for product/market fit, and a profitable business model to build Pinfinity on. So, this is a fairly high risk engagement; Pinfinity, as an asset, is not generating any cash and is not likely to do so in the near future. It has, however, helped me build another, critical asset: relationships.

Even so, I need to stay true to my deliberate strategy, and keep my time commitment to this company limited. It is high risk and costly, at a time when I should be reducing my exposure to risk, and spending my time on investments with a better return in the near term, so I'm going to try to discipline myself to only spend 20% of my time away from my work with MadGlory on Pinfinity projects.

Nevertheless, I still need to maintain some risk in my "portfolio", and Pinfinity is built on a core mission that I really believe in. Pinfinity will remain the only startup in my portfolio, while I spend more time bootstrapping other assets. Someday I hope to be in a position where I can dedicate more time to Pinfinity.

Bootstrapped to Profit ASAP

So, I already have a reliable income (with a great workplace), and I'm involved in a promising "we shall go to the moon" startup, but I still need to be building an income business to support my family. And, it should be a project that begins the asset building process as well. I call this my Bootstrapped to Profit ASAP product, because it needs to be designed to become profitable as soon as possible using just a small percentage of my time and income. What I came up with is the HTML and CSS Tutorial.

It started out as an idea to self publish an eBook about advanced topics in front-end web development about 6 weeks ago. Then, through my market research, I discovered that our industry really needed a good place for beginners to go to learn web development. Our public and private schools don't really do a great job, and whenever you ask a developer where to go to learn, they usually tell you to just get started, and use Google to figure it out. So, beginners go to Google, and what do they see? The top results for "learn html" or "html tutorial" contain, not only terrible learning material, but also a lot of misinformation that will have to be "unlearned" later.

Given that, I shifted my idea to self publishing an eBook about HTML and CSS for beginners, and eventually landed on the idea of creating a tutorial series. It will consist of a website, containing all the written material, for free. On top of that, I'll sell video tutorials and other supplemental content.

The HTML and CSS Tutorial is something that I can do with the time I have outside of MadGlory, while still meeting my obligations to Pinfinity. In fact I think I can learn a lot from this project which will help us establish a successful business model at Pinfinity.

I plan on selling something on day 1, rather than waiting until I have an audience of millions. And, while there is no guarantee, I believe I can market and sell this product at a level that will eventually sustain my family and allow me to continue building assets, getting that snowball rolling down the mountain.

Given that asset building is a top priority for me right now, I'm going to try to spend 70% of my time outside of my responsibilities at MadGlory to get the HTML and CSS Tutorial bootstrapped. Stay tuned for more information on this, since I want to release something as soon as possible.

Where The Rubber Meets the Road

Having a good strategy is all fine and dandy, but if I can't make the day to day decisions to execute on it, then it's worthless. Thinking about, and making the right decisions is something I really need to get better at.

So, I'm going to leave off with one more quote from Clayton Christensen:

If the decisions you make about where you invest you blood, sweat, and tears are not consistent with the person you aspire to be, you'll never become that person.

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