Weekend Briefing No. 240

Welcome to the weekend.

I’m super excited to announce the launch of my new briefing –  Crypto Esq. The pace of innovation in the cryptocurrency, blockchain and smart contract world is tremendous. As usual, innovation is outpacing regulation. So, this email briefing is my humble attempt to understand how the law is impacting (and being impacted by) the development of these new technologies.

The format is pretty simple: I source and summarize relevant articles and provide a link to those articles if you want to read further. Readers of the Weekend Briefing will be very familiar with the format. Right now, I’m not committing to releasing Crypto Esq at any given frequency, we’ll just see how it goes.

This is an experiment and I need your help. Many of you subscribed a while ago when I announced my intention to create Crypto Esq, so thank you! The response was way stronger than I thought it would be. If you are interested in this topic and / or have friends who would dig this, please SUBSCRIBE.


Prime Numbers

20,000 – The world’s most prolific writer is… you guessed it… a Chinese algorithm. A new program from Alibaba can produce 20,000 lines of ad copy a second.

1000 – Alphabet company Loon just beamed the internet 1000km using a network of seven balloons.

200 – Ethereum is in a bear market. Short positions on the cryptocurrency have risen by more than 200% in the past four weeks.

Slow Growth Unicorn

Pinterest, valued $12.3 billion, is a unicorn, but it doesn’t act like one. Ben Silberman, CEO of Pinterest doesn’t spend much time at tech conferences or on magazine covers. Instead, he dedicates an outsize amount of time to meeting with Pinterest users, going on six tours a year and holding weekly lunches at Pinterest’s offices. If Pinterest addresses the needs and desires of its users, he said, “the business will take care of itself.” What Pinterest’s critics identify as negatives (conservative decision-making, less urgency, squandered opportunities), its supporters cite as positives (bullets dodged, wasted time avoided). As a result, conversations about Pinterest tend to raise fundamental questions about the nature of success in Silicon Valley. “I want to believe that more thoughtful, slower growth is better,” said Tracy Chou, a former Pinterest engineer. “But the examples that are very visible seem to suggest that really aggressive growth wins, at least in the near term.” Mr. Silbermann notes, “In technology, people are very, very fast to declare something a winner or loser, like, ‘That’ll never work,’ or ‘That’ll take over the world.’ The truth is always somewhere in between.” New York Times (11 minutes)

Algorithmic Justice League

Joy Buolamwini was a graduate student at MIT a few years ago when she was working on an art and science project called the Aspire Mirror. The set up was supposed to use readily available facial recognition software to project images onto people’s faces. But the software couldn’t identify African-American Buolamwini’s own face—unless she put on a white mask. She tells the story in more detail in a TED talk. As she encountered other examples of what’s become known as algorithmic bias, Buolamwini decided to conduct a more rigorous review. Putting three well-known facial recognition programs to the test (including ones from IBM and Microsoft), she found that all had a significantly harder time correctly identifying darker skinned faces, particularly of women. So, she attacked the problem of algorithmic bias head on, forming the Algorithmic Justice League, a group of real life superheroes with the mission of ferreting out and eliminating bias in the machine learning and artificial intelligence. Algorithmic Justice League (10 minutes)

Blockchain & SMEs

Jointly conducted and released by the World Economic Forum and Bain & Company, the research indicates that, by deploying blockchain, global businesses can generate an extra $1 trillion in trade finance that would otherwise be missed out on. Since distributed networks are able to share business records across financial institutions along the supply chain. This transparency will enhance businesses’ credibility and, in turn, help mitigate credit risk, lower fees and remove barriers to trade. If the blockchain was broadly implemented, the main beneficiaries are set to be SMEs and emerging markets, which suffer most from a lack of access to credit and have ample room to grow trade. World Economic Forum (18 minutes)


Life moves really fast. It’s easy to wake up and wonder what happened in the last six months…  or the last year. I find this is especially the case with my friends who are high achievers in their career or building a family.  I personally strive to build in time for daily, weekly and annual rest and reflection. My friend and client Ben Messner created something called the Reflection Ritual Journal – a journal with a guided annual practice for reflection. He’s already crushed his goal on Kickstarter. But if you want to get your hands on the first run, you may want to back the project. Reflection Ritual (3 minutes)  

Glomar Explorer

In 1968, an aging Soviet sub armed with nuclear missiles and torpedoes sank in the Pacific. The Soviets couldn’t find it, but the US Navy did, three miles below the surface. Thus began a six-year covert salvage effort that led the US Central Intelligence Agency to team up with billionaire recluse Howard Hughes to build a deep-sea drillship called the Hughes Glomar Explorer. It all went swimmingly… until a mysterious group of burglars, the Los Angeles County Tax Assessor, and Rolling Stone magazine got involved. With conspiracy theories, erratic billionaires, and Russian espionage all top of mind, today let’s diving into one of history’s most ambitious heists. You can’t make this stuff up. Quartz (12 minutes)


Literally translated, sitzfleisch means ‘sitting meat’ or ‘sitting flesh’ – in other words, a term for one’s behind or bottom. To have sitzfleisch means the ability to sit still for the long periods of time required to be truly productive; it means the stamina to work through a difficult situation and see a project through to the end. When someone says you have sitzfleisch, it’s usually a professional compliment: it means they believe you’re capable of focusing long enough to complete a tough project or finish whatever work needs to be done. If you don’t have sitzfleisch, however, that is a particularly evocative way of suggesting you might be flighty or unable to concentrate on one thing at a time. BBC (7 minutes)

Big Decisions

If you find yourself mapping a “whether or not” question, looking at a simple fork in the road, you’re almost always better off turning it into a “which one” question that gives you more available paths. One approach, known as scenario planning, developed by a handful of management consultants in the 1970s, involves imagining three different future environments for each alternative: Concoct one story where things get better, one where they get worse, and one where they get weird. The psychologist Gary Klein has developed a variation on this technique. He calls it a “premortem” –  imagine that it is months into the future and that their plan has been carried out. And it has failed. That is all they know; they have to explain why they think it failed. New York Times (7 minutes) 

Weekend Wisdom

I can sing as well as Fred Astaire can act.Burt Reynolds 

About the Weekend Briefing

A Saturday morning briefing on innovation & society by Kyle Westaway – Managing Partner of Westaway and author of Profit & Purpose.

Photo by Shaah Shahidh