Roundup: 10 May 2015

"School is about dealing with certainties. Life is about the ability to handle the maximal amount of uncertainty."

- Nassim Taleb

Where you born in the early 80’s? If so, do you feel like you meet the criteria for being Gen X, or perhaps a Millennial? I have always felt like I’ve been in flux between these two concepts, a sort of weird mix of "grunge cynicism" and "new era optimism" that defies specific categorization.

Anna Garvey has perfectly vocalized this feeling in an article 'The Oregon Trail Generation’ about those born at the tail end of the 70's or start of the 80's - the digital new school pioneers who still had a foot in the old school world of analog. A fascination read.

A very interesting take on the violence in video games argument. New models like Telltale Games “murky ethical choices” gameplay mode are creating an interesting experimental space in which to explore ethics and the nature of conformity bias. Do you just go along with the group?

Why is it that we are witnessing the rise of companies predicated on trust amongst complete strangers, but at the same time most studies are showing overall trust in society and individuals is at an all time low? It turns out people are putting a lot of faith in trust between one person and the crowd, thanks to digital communication channels. The Internet is forever changing the dynamics of human interactions.

Organizational Lessons

I have written about the Tragedy of the Commons previously, but a great example of this concept is the “spaghetti-ball mess” that was the downfall of MySpace. How a giant of a company failed by losing sight of benevolence, and focusing on a quick buck, not the users.

Seth Godin on why you need editors, not brand managers, and the future of Content Marketing. I love this quote - “There are constantly trends and fads on the Internet, and people make a good living amplifying them. But I think that industrialized content marketing is one of those fads, and it will end up where they all do: petered out because human beings are too smart to fall for its appeal.” Remember to be authentic.

Speaking of Content, one organization who is absolutely killing it in the content game is Patagonia. They have started making long form film content to support their purpose and nonprofit causes, a perfect fit for their brand. Some great lessons here.

If you care enough to try to solve a problem, then it matters to you. If it matters to you, it must affect you in some way. If it affects you strongly, that means that you are probably inside the problem - which means you are part of the problem. Change your mindset and think deeply about the system you are in when problem solving.

Design & Planning

When interviewing users, never ask what they want - they will only think in the realm of possibility. Instead, ask these three powerful questions - what are you trying to get done, how do you currently do things, and what could be better about how you do it?

Google has always put forward that good SEO is about making things amazing for the user. With mobile overtaking desktops as the most used device on the Internet (and more searches now coming from smartphones), “mobile friendliness” or lack of could start to massively impact your rankings. Do you have a good mobile website experience?

How to design killer website from Google Ventures. Need I say more.

The next big things in design? Anticipatory. With so many choices, and the growing paralysis of decision fatigue, companies that will win the in the future will anticipate user needs in order to make decisions for them. Eliminating steps through data will become a huge advantage.

Strategy is no longer just about planning and audience insights. A flawless user experience is now also a must - which means strategy and UX need to learn from each other. Four things strategists can learn from their talented UX designer counterparts.


Software as a Service companies in the small-to-medium business segment are showing an interesting pattern - they inevitably begin to serve much larger enterprise customers (think Box, Hubspot or Zendesk). The reason behind this may be an exact visualization of Clayton Christiansen’s Innovator’s Dilemma.

SMB companies often feature simpler products, mobile app store distribution, and freemium pricing which makes them appealing to their target market. As growth slows down, they target enterprise to increase growth, starting the disruption cycle all over again as they become large themselves. A fascinating look into this arc phenomenon.

What did billion dollar “unicorn” startup companies look like at Series A? Funnily enough, they rarely look like a blue ocean strategy, but rather right in the heart of a red ocean trap. Shasta Ventures has done a fascinating analysis, showing most exhibited the following traits: Easy-to-dismiss ideas or perceived crazy ideas, highly competitive markets, reinventing existing customer behaviors, untested founders with high degrees of passion, and a lack of monetization plan that focused on user needs. 

A fascinating look at Sam Altman, the 30 year old President of Y Combinator, the “Unicorn Breeder” of Silicon Valley that has helped birth such luminaries as Dropbox, Airbnb, Twitch, Quora and Reddit.

Could a single solo entrepreneur build a startup with 1 billion users? Companies used to exist because the cost of doing business inside the firm was less than the cost of doing business with parties outside the firm. Digital platforms are starting to flip this on its head. 

Is the on-demand sharing economy unlawful? The lawyer who is trying to destroy the sharing economy through legal action. New models of operating tend to fall victim of outdated rules and regulations (and thinking), which can bring out the trolls.

Personal Growth

Want to make better decisions? Understanding Behavioral Economics is a great way to understand the heuristics and biases that affect decision making. A great HBR article with a framework that layers in the three key decision-making philosophies, and when to use them.

Ralph Waldo Emerson said “Our strength grows out of our weakness”. A great Zen Habits post on the mindset behind turning your perceived weaknesses into strengths, with some great applications for business settings. 

Despite what you may have heard, you can actually change your brains patterns after 25 - it just takes a lot of hard work. How to change your brain’s pathways and patterns.

Peak performance in a creative field requires a combination of talent and skill - however belief that you can improve your skills is often the most defining factor in improvement. In order to become more creative you need to focus on becoming an explainer, practicing openness, and to keep asking new questions.  

The Lucretius problem. Only a fool believes the tallest mountain in the world will be equal to the tallest one he has observed. An excuse for failure or catastrophe should never be “it never happened before”.

To finish, a great short doco on the rising power of the social media influencer. It's now more often than not becoming a world in which you need to influence the influencers, not the masses.