Posts in "Technology"

On Antifragility and why we need a National Entrepreneur Day

Antifragility. It’s an awkward word but one that sinks in to your consciousness as you read “Antifragile: Things That Gain from Disorder” by Nassim Nicholas Taleb. As a big fan of The Black Swan by the same author, I eagerly devoured this book. It takes the findings of the Black Swan and projects it outwards in to a philosophical and pragmatic outlook on modern life. Taleb is a divisive, opinionated, funny and passionate writer and this book, like his last, seems to have settled in to place at the base of my spine where I will carry it forever.

So what does antifragile mean? Well if you have a linear scale with “fragile” on the left, the common thought is that “robust” sits opposite to that on the far right. However what Taleb introduced with the notion of the Black Swan and expands upon now, is that robust doesn’t exist as this polar opposite state to fragility. Instead, a robust system is one that protects itself against known dangers, but as a consequence is hugely vulnerable to Black Swan, or unpredictable, events. Taleb instead proposes the notion of antifragility as it represents both preparation for known fragility whilst also allowing for the unknown. Whether they be small, large or Black Swan sized setbacks, the antifragile person or organization is set up to roll with the punches and still come out fighting.

If you work in an agile software development environment, or are an entrepreneur, or work in an entrepreneurial environment, then you are probably seeing some key familiarities with your daily work-life. The much discussed innovators burden is that they need to accept failure more than success, because every setback propels you forwards in the end, so long as you learn from your mistakes and can keep going. Failures should be bumps on the road to success, not big gaping pot-holes from which you will never emerge. Taleb himself sees this correlation between antifragility and start-up, Agile business culture, so I wanted to share some of his nuggets of wisdom.

On Entrepreneurs & Start-Ups

To answer the question of where Taleb sits on the scales of opinion regarding entrepreneurs, I present exhibit A:

My dream—the solution—is that we would have a National Entrepreneur Day, with the following message: Most of you will fail, disrespected, impoverished, but we are grateful for the risks you are taking and the sacrifices you are making for the sake of the economic growth of the planet and pulling others out of poverty. You are at the source of our antifragility. Our nation thanks you.

His impassioned view of entrepreneurs and scrappy start-ups ties very closely to his views on education. He believes in trial and error, and people who forge a path with nothing or little to lose and a lot to gain.

No one at present dares to state the obvious: growth in society may not come from raising the average the Asian way, but from increasing the number of people in the “tails,” that small, very small number of risk takers crazy enough to have ideas of their own, those endowed with that very rare ability called imagination, that rarer quality called courage, and who make things happen.

Also that start-ups fertilize the soil on which the economy will continue to grow:

The fragility of every startup is necessary for the economy to be antifragile, and that’s what makes, among other things, entrepreneurship work: the fragility of individual entrepreneurs and their necessarily high failure rate.

Whilst also forging the path towards greater knowledge:

Entrepreneurship is a risky and heroic activity, necessary for growth or even the mere survival of the economy. It is also necessarily collective on epistemological grounds—to facilitate the development of expertise.

So foster that pursuit of trying new things and learning from your mistakes and failures:

my characterization of a loser is someone who, after making a mistake, doesn’t introspect, doesn’t exploit it, feels embarrassed and defensive rather than enriched with a new piece of information, and tries to explain why he made the mistake rather than moving on. These types often consider themselves the “victims” of some large plot, a bad boss, or bad weather.

On Innovation

In turn, innovation evolves out of this entrepreneurial, trial and error, antifragile spirit:

How do you innovate? First, try to get in trouble. I mean serious, but not terminal, trouble. I hold—it is beyond speculation, rather a conviction—that innovation and sophistication spark from initial situations of necessity, in ways that go far beyond the satisfaction of such necessity (from the unintended side effects of, say, an initial invention or attempt at invention) … The excess energy released from overreaction to setbacks is what innovates!

Also an interesting outcome of the antifragile thinking is that the best ideas should come via negativa:

we know a lot more what is wrong than what is right, or, phrased according to the fragile/robust classification, negative knowledge (what is wrong, what does not work) is more robust to error than positive knowledge (what is right, what works). So knowledge grows by subtraction much more than by addition—given that what we know today might turn out to be wrong but what we know to be wrong cannot turn out to be right, at least not easily.

And just like a good writer or programmer who enjoys removing words and code to reach a more elegant solution, Taleb quotes one of my favorite Jobs-ism’s:

Finally, consider this … saying from Steve Jobs: “People think focus means saying yes to the thing you’ve got to focus on. But that’s not what it means at all. It means saying no to the hundred other good ideas that there are. You have to pick carefully. I’m actually as proud of the things we haven’t done as the things I have done. Innovation is saying no to 1,000 things.

On Risk Taking 

Risk taking is where the spirit of antifragility meets reality. There must be an acceptance of asymmetric payoffs:

To see why asymmetric payoffs like volatility, just consider that if you have less to lose than to gain, more upside than downside, then you like volatility (it will, on balance, bring benefits), and you are also antifragile.

As a product manager in software development, this quote rang so true about decisions our product team make daily:

In other words, if something is fragile, its risk of breaking makes anything you do to improve it or make it “efficient” inconsequential unless you first reduce that risk of breaking.

Taleb also proposes a heuristic against which to validate your ideas by using extremity of opinion, both positive and negative (of course):

consider this simple heuristic: your work and ideas, whether in politics, the arts, or other domains, are antifragile if, instead of having one hundred percent of the people finding your mission acceptable or mildly commendable, you are better off having a high percentage of people disliking you and your message (even intensely), combined with a low percentage of extremely loyal and enthusiastic supporters. Options like dispersion of outcomes and don’t care about the average too much.

It is also not about being right most of the time but instead being wrong with impunity and right that one time when it matters:

The frequency, i.e., how often someone is right is largely irrelevant in the real world, but alas, one needs to be a practitioner, not a talker, to figure it out. On paper, the frequency of being right matters, but only on paper—typically, fragile payoffs have little (sometimes no) upside, and antifragile payoffs have little downside. This means that one makes pennies to lose dollars in the fragile case; makes dollars to lose pennies in the antifragile one. So the antifragile can lose for a long time with impunity, so long as he happens to be right once; for the fragile, a single loss can be terminal.

On Education

Taleb is unforgiving in his assessment of the education system in the modern first world. The most powerful idea he presents is an assessment of the relationship of between education and wealth:

The implication is nontrivial. For if you think that education causes wealth, rather than being a result of wealth, or that intelligent actions and discoveries are the result of intelligent ideas, you will be in for a surprise. Let us see what kind of surprise.

I fully agree with this, now I read it, but I had never reviewed the relationship objectively in this way. Once you do, you see that entrepreneurialism and risk-taking in the US are the bases of future growth and wealth and it is this spirit that we should be fostering along with core STEM fields:

Many people keep deploring the low level of formal education in the United States (as defined by, say, math grades). Yet these fail to realize that the new comes from here and gets imitated elsewhere. And it is not thanks to universities, which obviously claim a lot more credit than their accomplishments warrant. Like Britain in the Industrial Revolution, America’s asset is, simply, risk taking and the use of optionality, this remarkable ability to engage in rational forms of trial and error, with no comparative shame in failing, starting again, and repeating failure.

And once again, what we see in software development so often now, is that some of the best developers are those passionate “amateurs” without the formal training:

Amateurs in any discipline are the best, if you can connect with them. Unlike dilettantes, career professionals are to knowledge what prostitutes are to love.

I just love that last line!

On Data

I found it very refreshing to read Taleb’s perspective on data, and particularly the dangers of big data. Working on the web you are constantly made-aware of the need to gather and use data to guide your decision-making. This is not something I disagree with per se, but something I am wary of, and Taleb captured my wariness in three words:

data increases intervention

Like a doctor who feels he must prescribe a pill in order to have a sense of agency in an uncertain situation, a product team will feel the need to constantly tinker with their product as a result of data, which is not bad in itself, but is compounded by the very quantity of data available:

In business and economic decision making, reliance on data causes severe side effects—data is now plentiful thanks to connectivity, and the proportion of spuriousness in the data increases as one gets more immersed in it. A very rarely discussed property of data: it is toxic in large quantities—even in moderate quantities.

So amid this large quantity of data, the real information can be lost, skewed or overlooked altogether:

Modernity provides too many variables (but too little data per variable), and the spurious relationships grow much, much faster than real information, as noise is convex and information is concave.

Going back to innovation via negativa, data should be used likewise:

Increasingly, data can only truly deliver via negativa–style knowledge—it can be effectively used to debunk, not confirm.

On Life

I will end with a more general quote, but one that demonstrates the underpinning of Taleb’s whole outlook and why this book just sang to me. The fact that life is about ups-and-downs. About failures and successes, and risks and rewards. To try and level everything out is to set yourself up for a bigger and more inevitable fall, like the economists who thought modern financial life had evolved beyond the boom-bust cycle just before the greatest depression in 60 years. There is no flat line through life, but if you are ready for the troughs and protected against the unknown, then the peaks will be all the sweeter and more lucrative:

The best way to verify that you are alive is by checking if you like variations. Remember that food would not have a taste if it weren’t for hunger; results are meaningless without effort, joy without sadness, convictions without uncertainty, and an ethical life isn’t so when stripped of personal risks


Mental Model Mis-steps

Traveling is a wonderful way to bring in to focus just how much of your daily life is beholden to a mental model of how things work. On a recent trip back to the UK, a country from which I moved some 7 years ago, I picked up on a series of UK specific cues that my brain mis-interpreted as it varied from what I am now used to in America.

As I was driving round a small town, I turned on to street seemingly only wide enough for one car. On the left side of the road was a car parked facing me. I panicked, thinking I was going the wrong way up a one-way street (remember, they drive on the left in Blighty). It was in fact a two-way street, but it reminded me that in the UK you do not have to park facing the same way as the traffic is moving. Subconsciously my brain had established a shortcut to determining if a street was one-way that wasn’t by looking at the road signs. Instead I was subconsciously taking note of the direction of the parked cars. I had a mental model of what a one-way street looked like.

Another interesting example was how UK services, particularly web services, advertised in the mass media. The trend in the UK is for services to use a very conversational tone, along with slang and regional vernacular. Services such as and have an almost purposefully scruffy look and tone to their brand. UK audiences seem to react well to this, and I would gamble that part of the reason why is as a reaction against many years of BBC-style, regionally agnostic Queens English that most everyone north of the Watford Gap saw as ‘posh’ and ‘southern’. Having been Americanized over the last 7 years, that goes against my mental model for what a trustworthy service looks and sounds like. Services are advertised with a higher degree of slick and polish in the US, and for the most part are still regionally agnostic in tone so as to achieve the broadest appeal without falling into stereotypes. I had a mental model for what a trustworthy service should look and sound like, and my immediate reaction against this opposite tone in the UK was negative.

I characterize these jolts to my subconscious understanding of the world as a ‘mental model mis-step’. They are short-sharp shocks to your perception. They unsettle you, sometimes just for a split second, but noticeably nonetheless. It’s like tripping on an uneven sidewalk (pavement). It throws you off your stride and you lose your cool. You may even look around to see if anyone noticed. It can be distinctly unsettling. This reiterated to me how important a well designed user engagement flow is for online interactions. To interrupt a user in pursuit of their goal, even to possibly help them, is to present an opportunity when the user may lose their cool and temporarily feel insecure in their convictions. You must clear and smooth that sidewalk. Understand who is walking down it and where they want to go, and the number of people who succeed should increase.

Job titles are signposts

In the “Lets Make Mistakes” podcast, episode 50, there was a listener question that prompted a characteristic rant from Mike Monteiro. To paraphrase, the question was, “If you create wireframes, are you are designer?”, to which Mr. Monteiro became very heated in explaining that if you are helping to solve the problem at hand, then yes you are a “designer”, because you are designing solutions to problems. End of story.

I understand Monteiro’s line of argument very well, as it is something I have argued myself many times. He is adamant that no time should be spent on figuring out job titles. We should just unify in solving the problem. Makes perfect sense. I always hated being in an environment where a) there were titles next to names on office doors or cubicle badges and b) people aspired only to have their name next to that title instead of actually doing a good job. However I think there is a deeper point being missed here.

The phrase “to explain the problem is to start to solve the problem” immediately rang around my head as Mr. Monteiro picked up speed. The need to create job titles such as Information Architect, User Experience Designer and Content Strategist, is part of the process of understanding the problem. Roughly 5-7 years ago there was a burst of interest in Information Architecture. As websites grew, and the web matured, organizations realized that there was a mess of incongruent information on their web holdings, and no unified pattern of navigation. So, Library Sciences emerged from the physical bookshelves and started applying similar rigor to the web. Yes we gained a job title that may seem superfluous, but underlying this was a need to start thinking about the organization and navigation of information on the web in a more holistic fashion.

Looking back over the last 2-3 years there has been a similar surge in interest around Content Strategy. As the “content first” argument picked up traction, so a new specialist profession was born of people who do not manage content and it’s creation, but instead strategize around what that content should be, and to what broader organizational goal it should serve. Had people always been doing this job? Yes, absolutely. But was it common practice? Absolutely not. Hence a new job title and consulting business space was created to specifically serve and evangelize this need.

Now take User Experience (UX) and we see the same pattern. To again paraphrase Monteiro, “everyone is having a user experience, whether they are using the train or buying a coffee, so what the hell does a UX Specialist do?”. Well, as aggravating as the title may be, appending “UX” to a title is an implicit acknowledgement that the correct strategic dissemination and organization of information on your site is not enough for it to be successful. It is the physical embodiment of the realization that there is an emotional component to your website or application, and somebody needs to take responsibility for that.

If that person is called a “Designer” then great, just so long as there is someone or process to deliver on that, then who cares what they are called. Job titles in many way are signposts along the way to a better understanding of how to build and manage engaging websites and applications. They may represent a bureaucracy and hierarchy, and the many big business negativity that comes with that. But they can also represent the progression of understanding in the field.

API Documentation: Where to Begin

I just had my first post for the Braintree blog released today, check it out –

The first job I took on after joining Braintree was to help solidify, expand and generally make more comprehensible, the API documentation.  We have an awesome API at Braintree, but the learning curve can be a little steep, so I am starting off by working on a Quick Start and then some easy-to-follow tutorials.  I’ll update here as they are released.

Little Printer

I absolutely love the pitch for this product, the Little Printer, and the video from the design group BERG. They managed to give the product character, without sliding in to the Clippy danger zone.  The video just perfectly sets the tone and feel, and the face gives just the little touch of personality that enhances your feelings towards it, even before you see or touch it.

A great example of emotional design.