Esquire Theme by Matthew Buchanan
Social icons by Tim van Damme

03

May

Saving the World

Some kids want to save the world when they grow up.  Trouble is, saving the world is incredibly difficult, for one very simple reason: the world is big, you are small, and you only have so much time to do anything.

Young and ambitious minds do not readily grasp this concept.  But at some point, after so much time spent trying to move a boulder that just will not budge, you realize that you need more power to do something on the scale of world saving.

So if you have not given up on saving the world yet, you start trying to accrue the necessary power.  In simplest terms, that means making a lot of money - and the most direct way to do that is to get a job that pays a lot.  The problem here is that landing such a job is a difficult, competitive process, and excelling to the top is even harder and less certain.

You could also try to build your own company.  Plenty of people attain great wealth through entrepreneurship, but plenty more fail.  No two ways about it, world-changing wealth is very hard to come by, and chance is probably the dominating factor in attainment.

Nassim Nicholas Taleb once said something to the effect of, “You need skill to get a BMW.  You need skill and luck to get a billion dollars.”  This applies to pretty much any measure of power you can think of.  For another example, look at politics; it is hard enough to become a Senator, and harder still - to the point of stratospheric unlikeliness - to become President.

The truth is that you probably never will have enough power to change the world, let alone save it.  (And consider that nobody in history is widely recognized as having saved the world.)  I think everybody realizes this at some point.  But some people get so wrapped up in the acquisition of power that they forget why they acquire it in the first place.

Many of these people die without doing anywhere near as much good as their younger selves might have wished.  This is unfortunate and unnecessary.

As you walk your own personal path of life, remember that you do not know exactly where it is taking you, or how long it will last.  So while you are walking it, you might as well clean it up as you go.

Maybe one day you will find yourself in a position to have a world-changing positive impact, although you probably will not.  But you can leave your own personal sphere of influence better than you found it.  And that requires something even more important than power: humility.

02

May

Do Internet Entrepreneurs Really Peak at 25?

In a recent TechCrunch article, Michael Arrington quotes an unnamed venture capitalist as saying that “Consumer Internet entrepreneurs […] peak at 25, by 30 they’re usually done.”  According to the VC, there are two mains reasons for this: first, young entrepreneurs are more creative and imaginative; and second, they and are willing to put 100% of their lives into their startups.

While I can readily accept that most successful Consumer Internet startups are launched by 25 year old founders, I doubt this has anything to do with “peaking” at 25.  Instead, I think there are many more 25 year olds attempting to launch Consumer Internet startups than 30+ year olds.  I see three simple reasons to expect as much.

First, entrepreneurship is relatively risky.  A typical 25 year old is usually less risk adverse than a typical 30 year old, and this is very simply explained by the fact that the young have less to lose than the old.

Second, entrepreneurship requires long hours.  A 30 year old with a family is usually less inclined to work 16 hours days than a 25 year old with roommates.

Third, Consumer Internet entrepreneurship is trendy.  The young care about trends more than the old, and this goes for career choices as much as fashion.

In total, Consumer Internet entrepreneurship looks more attractive to 25 year olds than 30 year olds.  And if more 25 year olds go into entrepreneurship than 30 year olds, simple probability would expect most of the successful startups to have younger founders.  There is no need to posit some special capability that the young possess.

I think a VC could readily observe that there are more successful 25 year old Consumer Internet entrepreneurs, and that they are willing to give everything to their startups.  And those observations harmonize perfectly with the explanation I outlined.  But to claim that a 25 year old is more likely to succeed because of creativity and imagination requires both a way of measuring these characteristics as well as knowledge of the distribution of attempted and successful entrepreneurs by age.

Without the data, it is just speculation - and in the realm of speculation, Occam’s razor rules the day.  That is, truth is usually found in the explanation with the fewest assumptions.  So while it is exciting to ponder what unique abilities 25 year olds have that 30 year olds do not, reality probably boils down to a simple numbers game (as it usually does).  Indeed, the truth shall set you free - if it does not first bore you to death.

27

Apr

Look at Who is Leaping

Chris Dixon once opined that there are two kinds of people in the world: those who have started a company, and those who have not. I do not take issue with this per se; on the surface, it is just another way to divide the human population into two groups. But I have some concerns about the particular way he characterizes entrepreneurship.

What troubles me most is the glorification of risk. Chris starts off on that theme by stating that, among other things, starting a company means “building an organization from a borrowed cubicle with credit card debt and nowhere to sleep except the office.” He then goes on to say, “The important distinction is whether you risked everything, [and] put your life on the line […] to make something new.”

Let me pause for a moment and state that I do not think Chris necessarily intended to glorify risk. More than likely, he was writing out of respect for entrepreneurs who struggled with unfortunate circumstances - so I think the message I am perceiving is not the one he intended to send. However, he might not realize how many people will see this post as an elaborated version of Nike’s “Just do it” campaign, and how they might consequently suffer.

What are the consequences of such a misreading? Obviously, a failed business can leave you in bankruptcy. But even if you avoid bankruptcy, a failed company can and very likely will damage your reputation and potential on the job market - and it is this rarely discussed phenomenon that I want to highlight.

In some cases, a failed company on your resume will not hurt you. Say you are a young programmer turned failed entrepreneur, and you have no dependents and nothing to lose. The hiring manager at Acme sees your application for their entry level programming job. Acme is planning on paying you about $50k, so while they hope you work out as a hire, they are not terribly concerned about it. If it is a big company, and you are able to demonstrate your skill, the hiring manager probably will not care all that much about your failed company and your bankruptcy (which will come up on the background check). And if Acme is a startup, you might even have an edge with your demonstrated entrepreneurial spirit.

The situation changes as you mature. Imagine that you have a decade of experience and, after your company fails, you apply for a senior job at Acme. Now the company is planning to pay you $150k, which means they expect to derive somewhere from $300k up to $1MM in revenue off of your work. At this level, they care a lot about whether or not this turns out to be a good hire. And suddenly, your failed company and bankruptcy do not look so good. You might hope that the company will respect your ability to take a risk and work hard, but with the amount of revenue pinned on your hire, what is really going to shine through is your demonstrated ability to lose money. And if you have a wife, 2 kids, and a mortgage, it will look even worse - now you also have a demonstrated willingness to put other people at risk. You better believe your resume is going to the bottom of the pile.

But what if your company does not fail? Suppose it just delivers middling results after 5 to 10 years and you decided to get out. (This happens way more often than you might think.) Regrettably, your situation is not much better than if your company folds completely. When someone hires you for $50k, it is not a huge deal if you leave after a year. But when they hire you for $150k, you typically need to stick around and be productive for at least 2 to 3 years before your employer has made a net-net profit. So a hiring manager sees your middling startup that you want to leave, and they wonder “How do I know this person really wants to work for me? What if they just get bored in a year and leave me in the lurch?” After all, the one thing all entrepreneurs really do have in common is a demonstrated preference for working for themselves.

These are the kinds of risks that bust up families and lead to suicides. And I am not speaking from theory here. I have personally witnessed families destroyed by bad businesses. And I have also done enough hiring to speak from experience about the aforementioned risks that entrepreneurship poses to your value on the job market. Suffice it to say, the consequences of playing and losing the startup lottery are very serious, and not in some abstract way. “Bouncing back” is rarely a very bouncy process. “Crawling back through a mile of mud and broken glass” would be a more apt term.

Chris Dixon is ferociously intelligent, and a very accomplished entrepreneur - and I believe that is why he is actually more risk adverse than you might think (or he might realize). Consider that he has three Ivy League degrees - including an MBA from Harvard Business School - and worked on Wall Street before entering startup-land. For those who might not know what that means, I will quote a friend who put it best: “I wish somebody told me when I was growing up that, with most jobs, the most you can make is hundreds of thousands of dollars, but with banking, the most you can make is millions upon millions of dollars.”

And Chris is not alone in this phenomenon. What do Bill Gates and Mark Zukerberg have in common? Surprisingly enough, they both attended Harvard, and only dropped out when their businesses started to take off. And even if those businesses had failed, they more than likely could have returned to Harvard and then proceeded to work on Wall Street. So they were a bit more able to soak up failure than average.

Likewise, look at the founders of Google, who studied at Stanford (which is very much Ivy-tier). Or look at Amazon’s founder Jeff Bezos, who graduated from Princeton and worked on Wall Street before founding the company for which he is now famous. Paul Graham has degrees from Cornell and Harvard.  The list goes on.  In fact, among the entrepreneurs I personally know who have had successful exits, every single one has either an Ivy league degree, or something comparable to that (e.g. Johns Hopkins). In all these cases, failure would hurt a lot less than for someone lacking the career benefits of an elite education.

I joined SkyLine when it was in startup mode. We really did work out of borrowed cubicles. The president and I both have the same humble alma mater - which is to say, he could not “fall back” on Ivy League credentials and a job on Wall Street.  He also has nearly two decades of industry experience, and an extremely strong network.  He put a ton of thought and preparation into the creation of SkyLine - in other words, he worked assiduously to reduce risk. Which is a very smart move, considering that if SkyLine had failed, the consequences for him - a family man - would have been tremendous.

I have a good friend who is a serious mountain climber. On those rare occasions where I brave the heights with him, I am struck by the intimate relationship he has with risk. The risks of climbing are palpable and lethal - if something goes wrong, you very well may die. He works meticulously to ratchet the risk level down to something manageable. And while he cannot completely eliminate or control that risk level, his efforts at risk-reduction have a great deal of influence over the likelihood of us living or dying that day.

Entrepreneurship is a lot like climbing. It can kill you. And just as the longest-lived climbers tend to be the ones who are the most calculating about reducing risk, so too are the most consistently successful entrepreneurs the ones who do not simply “take the plunge.” You can always throw caution to the wind and hope to be lucky - but nine times out of ten, you will be unlucky. And as another friend likes to say, “hope is not a method.”

Do not assume that everything will work out just because someone who has a lot of advantages in life told you so. Look before you leap, and look at who is leaping; if they are better equipped to take a fall, you might reconsider jumping after them. A failure that means nothing to them could mean everything to you, and that makes all the difference.

20

Apr

Time Management is Not a Myth, it is a Misnomer

I find time management and productivity to be fascinating topics.  Of particular interest to me is the notion of “productivity porn” - that is, techniques which produce the feeling of productivity without actually increasing productivity (a problem I rate as fairly ubiquitous).

I have done a lot of experimenting on both ends of the “productivity technology” continuum, from absolutely nothing to full-blown GTD.  Relying on nothing but my own head was decidedly inefficient, at one point costing me a couple hundred dollars in late fees on a parking fine I had forgotten about.  On the flip side, I personally feel that, for me at least, strict GTD is far beyond of the point of diminished returns.  Today, I just nag my future self about what to do.  It seems to work well.

But how do I know it is working well?  That is, how do I know I am being as productive as possible?  I think this is the most important question in productivity.  I also find that it is the least addressed.

Productivity is, in essence, the efficient use of time - getting the most out of the minutes of your life.  So it seems reasonable to try to maximize productivity by minimizing wasted minutes.  And that is what most time management systems focus on - how to ensure that every minute is spent doing something productive (e.g., paying bills while waiting in the checkout line).  But this is misguided.

While avoiding wasted minutes is good, it is not necessarily the same as maximizing productivity.  Imagine a business which decided to maximize productivity by minimizing the time that employees waste.  With that priority, the business will reliably have busy employees, but not necessarily maximal profits.  In fact, the business will likely struggle with a demoralized, burnt out workforce and a high rate of churn.

Priorities are the alpha and omega of productivity.  Without them, it is quite possible to get lost in the administrative minutiae of todo-lists, calendars, and the latest productivity meme.  There is only so much time, and in order to do important things well, less important things are going to fall through the cracks.  Minutes must be wasted so that hours can be well spent.

This is why “time management” is a misnomer.  Technically, it is correct, insofar as time is a manageable resource.  But I think that the term “time management” encourages a mode of thinking that constantly seeks to squeeze more and more out of the minutes of your life.  And if you compare somebody who is focused on their priorities against somebody who is focused on time management, I would expect the former to be more accomplished.

A friend asked me how I found the time to write.  I responded that I do not find the time to write - instead, I fail to find the time to do other things that are less important than writing.  In order to do what is important to me, I am constantly deciding what not to do.  For every one post I write, that is a song I choose not to compose, an idea I choose not to model, an article I choose not to read, etc.  I am human, and I can only focus on a handful of significant priorities at a time.  Writing is one of my priorities, and that means I constantly ax other things just so that I can write the modest amount that I do.

So I personally do not think in terms of “time management.”  Instead, I think in terms of “time triage.”  There is always a mountain of things that I would like to do.  But I only actually do those things that are at the peak of that mountain.

Productivity consists of spending as much time at the peak as possible.  Everything else is a distraction.

04

Apr

Why Modern Software Developers Dress Better

(Skip the first two paragraphs to avoid technical minutiae.)  

I used the linqtoexcel project today with great results.  It plays a key piece in a bit of scaffolding technology I wrote, which allows me to generate a suite of models, repositories, and controllers for an ASP.NET MVC 3 application I am building.  With linqtoexcel, I can effortlessly parse an Excel spreadsheet full of column definitions, which I then use to generate the scaffolding.  Creating that spreadsheet is easy, requiring only a copy-and-paste of the output of a simple SQL Server query against the INFORMATION_SCHEMA (and some minimal post-processing).  Writing this scaffolding technology took a little more than a half a day of work, and the result is a CRUD-complete data layer that takes only a few seconds to generate.

The database schema I am working against has 294 columns spread out over 35 tables. If we assume that manually coding everything would take 10 minutes per table, plus an additional 2 minutes per column, and then tack on an extra 10% for errors, the total figure is about 17 hours of work.  Some might argue that 10% is an exceedingly optimistic error rate - if we assume 50%, the total figure balloons to almost 24 hours.  By comparison, the scaffolding approach only required 5 hours.

Considered from a business angle, scaffolding provided a 3 to 5-fold increase in software development productivity.  Not too shabby, especially considering how expensive software professionals are.  And that alone would be interesting enough to merit discussion.

But there is another angle that I find even more intriguing - the sociological angle.  Scaffolding minimizes the amount of time spent on back-end work (the guts of the system), allowing a developer to quickly get to front-end work - which is what the user actually sees and interacts with when using the application.  For example, the “like” button of Facebook is part of the front-end, while its mechanism of action is in the back-end.

As back-end work becomes more automated, what are the implications for the software profession?  The first thing I think is that “software professionals will look different.”  This is simply because front-end work is more attractive to extroverts than back-end work - and extroverts tend to look different.

It is not hard to see why an extroverted developer would prefer front-end work.  A developer who works solely on the back-end spends his entire life thinking about bits and bytes, and how to make them work smoothly.  In contrast, a front-end developer spends all of her time thinking about people, and how they use software - and it stands to reason that extroverts would prefer this type of work due to its people-orientation.

Since extroverts prefer to think about people, they probably care more about the opinions people have of them.  Extroverts are probably more likely to pay attention to fashion than introverts.  So to elaborate on my first thought, I would say that “software professionals will look more fashionable.”

I think examples abound that prove this out.  Mind you, this is not to say that software developers are going to become the standard bearers of fashion.  But if you compare the greats of past generations - such as Ken Thompson and Dennis Ritchie - with the modern greats - such as David Heinemeier Hansson and Mark Zuckerberg - I think a clear difference emerges.

Software development today selects for a slightly different type of person than it used to.  The face of the industry is literally changing, perhaps as rapidly as the technology itself -  and that is fascinating.

08

Mar

Smart Is Wrong

There are only a few fields in life - math, for instance - where correct answers to new questions are directly calculable.  In most of life - art, business, science, etc. - arriving at the right answer requires getting a lot of wrong answers along the way; or, to put it in plain English, “stumbling.”

Stumbling is ubiquitous.  Most of the time, in most fields, most people are stumbling their way to the right answer.  Entrepreneurs stumble upon viable business models.  Chefs stumble upon tasty recipes.  Biologists stumble upon new cures.  The stumbling might occur with varying degrees of grace, but it remains stumbling.

In each of these fields, the successful groups are quite smart.  But before they get their big, right answers, they run into a lot of wrong ones - and if the right answers have not arrived yet, the deluge of wrong answers can make an observer conclude that those groups are not that smart.  Usually, that conclusion is a mistake.

Smart is not just about getting the right answer.  It is also about trying to get the right answer to very hard problems.  So most of the time, smart is wrong - as well as ambitious and persistent.

11

Jul

Don’t Start Over

I used to draw quite a bit as a kid, and I wasn’t half bad. I attempted to compensate for my lack of talent with an intense work ethic. I would draw with an unmatched fervor, spending every free moment on my art, and every cent I had on supplies. It wasn’t uncommon for me to produce a couple hundred compositions in a month. Unfortunately, I couldn’t sustain this pace. I would burn out in a few months, and condemn everything I created to the dustbin. Some time later, with my skills considerably depreciated, I’d start the whole cycle over again. It was always three steps forward, three steps back. What I had in zeal, I lacked in patience, and eventually, I quit in frustration.

Patience is the great multiplier. Obviously, had I simply been patient, I would have eventually reached my goals (or at least the ceiling of my genetic ability). In fact, I would have been better off working slower and steadier, because patience can partially replace intensity — the amount of daily exertion required for progress is usually well beneath your peak-output capacity. On the flipside, intensity is a poor substitute for patience — you can only do so much in a single day, and the quality of work you do after 20 straight hours is usually much less than what you produce in the first hour. For non-trivial endeavors in particular, an attempt to replace patience with intensity will inevitably result in burnout and failure.

Intensity can be a vice. If you’re good at working hard, you’ll be tempted to try and trade patience for intensity. This might work in high school, but at some point, if you continue tackling progressively greater challenges, you’ll hit a brick wall. I became painfully aware of this during my sophomore year of college, when my programming assignments suddenly couldn’t be completed the day they were due in a single marathon session.

If you’re looking for a showcase of impatience and burnout, look no further than your local gym. Few people have the patience needed to stay in shape their whole life. Of those with the potential, many work too hard in an attempt to get faster results, ultimately giving up in exhaustion, frustration, and/or injury.

People who fail a fitness program usually don’t plan to quit forever. Rather, they plan to start again at some point in the future. But if you quit now, you throw away whatever progress you made. It would be far better to lower your goals (If you really wanted to be an Olympic athlete, you wouldn’t be thinking about quitting, so why not strive to simply be fit?), adjust your program, and then trudge along. But this stings the pride, and trudging really isn’t all that attractive.

In contrast, a clean slate is very tempting. You get to wipe away your mistakes, ignore the fact that your goals might be too lofty — and this time, you’re really going to kick ass. I’ve been there, done that. It’s much more appealing than injecting modesty and patience into your current routine, but the problem is that it does not work. Throwing away bad drawings doesn’t make you a better artist, just as quitting a fitness regimen won’t make you a better athlete.

The enticement of a fresh start is nearly always a Sirens’ Song, distracting you from the real problem: impatience. Although patience by itself won’t get you anywhere, it’s usually the limiting factor; and wiping away your mistakes, all the while vowing to work harder “next time,” will not compensate for a lack of patience. Starting over is rarely anything more than the stuff of failed New Years resolutions.

Is there a time and place for starting over? Probably. But personally, the next time I feel the urge to start from scratch, I’m going to ask myself if it’s really the best choice, or if it’s simply more appealing than confronting my impatience.