Weekend Briefing No. 359

Welcome to the weekend, and welcome to the last briefing of the year. For many of us, 2020 can’t end soon enough. We’ve been through a lot, and just making it through this year is an accomplishment in itself.

Every week, I serve up seven articles to you. But this week, I looked back through the year and included 20 of the best articles of the year and three of the best Prime Numbers. In addition, I’ve included a ranked-and-rated list of all the books I’ve read this year in the Bookshelf section.

The process of writing this briefing was a reminder that, though this year was challenging on so many fronts, there was some goodness. I hope that this year has slowed us down and caused us to take time to reflect on what is truly meaningful. During this holiday season, I hope you reflect on the steps you are going to take in your relationships, your company and your community to make 2021 better for those around you.

One of my highlights this year was our weekly “Bourbon and Briefing” Zoom happy hours. During the heart of the pandemic, it was a great solace and joy to build new friendships with you. So, thank you to that crew.

I’m truly grateful for all of you. We live in a chaotic world with so much content. I consider it a privilege that you would make the Weekend Briefing a part of your weekend ritual.  

Lastly, since this is a “best of” issue, it would be a great summary to share with your friends. Please do me a favor, and forward this to two or three of them.

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Prime Numbers

578—The oldest company in the world was founded in 578 AD. It’s a construction firm called Kongo Gumi that has specialized in building temples for 14 centuries. This map is a fun look at the world’s oldest companies.

5,999.99—Costco sold a one-year supply of food for four people for $5,999.99.

1080—A Brazilian 11-year-old has become the first person to pull off a 1080—three complete turns—on a vertical ramp.

JTBD Framework

Whether you’re a product manager innovating within a larger company, or building a brand new early-stage product at a startup, the Job To Be Done (JTBD) framework works to create better, non-obvious insights about your audience. Ultimately, the core value of this framework is that it provides an approach to gathering an understanding of who your user is, and what their motivations and hopes are. It starts with a clear JTBD statement, which helps you communicate with absolute clarity what a specific group of people want in a specific circumstance—and their barriers to getting it. To put that into practice, here’s a JBTD statement template that I find helpful and is commonly used among Facebook and Instagram product teams: (1) When I … (context). (2) But … (barrier) (3) Help me … (goal). (4) So I … (outcome). First Round Review (22 minutes)

Managing a Remote Team

Few practical resources exist on how to exactly manage a remote team well. I liked this one from Know Your Team. If you’re a first-time manager of a remote team, or a manager who’s transitioning to work from home, this free guide—with 60-plus pages based on a survey of 297 remote managers and employees research—may be worth checking out. Claire Lew wrote 11 chapters on best practices for managing remote teams. Based on their research, we cover these topics: (1) Process and Tools: How to collaborate effectively when your team is remote; (2) How to build a social connection in a remote team; (3) Performance management in a remote team; (4) Setting employees up for success. This may be a good thing to read before you start those Zoom calls on Monday. Know Your Team (45 minutes) 

CEO Mindset

Which mindsets and practices are proven to make CEOs most effective? According to an extensive study by McKinsey, effective CEOs (1) Do only what they can do. (2) Center on the long-term “Why?” (3) Help the board of directors help the business. (4) Put dynamics ahead of mechanics. (5) Manage performance and health. (6) Focus on beating the odds. McKinsey (23 minutes)

CEO of No

Andrew Wilkinson is a partner at Tiny, where he starts, buys and invests in internet businesses. Over the last few years, he’s built it into a thriving collection of companies—more than 30 with about 600 employees collectively. But here’s the conflict: Even though his job is all about people, he doesn’t like to be on the phone with them too often. He only likes to do two to three meetings a day, which is surprisingly few for a guy with 600 employees. He has templates with 100 different polite ways to say, “No.” But this habit of saying “no” spreads beyond his inbox. He’s really set up his whole life by saying “no.” He’s said “no” to venture capital. He’s said “no” to living in Silicon Valley. And, at his company, he’s used delegation to say “no” to anything that will require him to do work that he doesn’t want to do. In short, he’s said “no” to anything that doesn’t fit into his vision of success—and it’s working pretty well. He’s the CEO of No, which seems to leave a lot of room for the life he’s said “yes” to. Learn how he does it in this interview. Superorganizers (11 minutes)

Process Assistant

Invisible is a tool for realizing potential by breaking past the clutter of modern life. Hayley Darden, Marketing Director at Invisible (and my good friend/former roommate/sometimes karaoke partner), thinks of an Invisible virtual assistant less as a personal assistant than as a process assistant: not good for random errands—such as haggling with Verizon customer service—but excellent with repetitive, mind-numbing chores—whatever you most hate doing in your life. Invisible grew from two ideas, one about bigness and the other about smallness. The bigness idea was that processes in a business or a life ought to be managed by one entity—a virtual super-assistant who can deal with anything. The smallness idea was that complex processes can be broken down and run in bits. The founder’s inspiration, on the latter point, was Henry Ford. “Every year, the price of Ford motor cars kept dropping, and the quality kept improving,” he said. The key was separating production into simple tasks, such as screwing in a single lug nut, and then snapping those tasks together like Legos on the factory floor, allowing processes to be built without hiring new teams, then tightening to the inch. The company’s workflow operates as a “digital assembly line.” The writer of this New Yorker article tried the service and describes it this way: “I felt as if someone had broken into my home and scrubbed my bathroom while I slept.” The New Yorker (31 minutes)

Bill Gates

Bill Gates gives brilliant 30-second answers to common job interview questions. For instance: Q: Why should I hire you? Bill Gates: You should look at the codes that I’ve written. I write software programs way beyond any classes that I’ve taken. I think I’ve gotten better over time, so take a look at how ambitious I’ve been there. I do think I can work well with people. I might criticize their code a little harshly, but overall, I like to be on a team. I like ambitious goals. I like thinking through how we can anticipate the future. Forbes (6 minutes)

WFH Bingo

Just because we’re on lockdown, it doesn’t mean that we can’t have a little fun. Here’s a little something that should spice it up—”Working From Home During a Global Pandemic BINGO.” McSweeny’s (3 minutes)

20 for 2020

One thing I’m learning over and over again is that it’s not my Black friends’ job to educate me on the experience of being Black in America. As Casey Gerald said: “Dear White People: There are Black people who have signed up to do the work of helping you be anti-racist. I am not one of them. Chances are, the Black people you’re asking for guidance & emotional support aren’t, either.” If we want to be allies to our black friends and colleagues, it is incumbent upon us to do the work to get educated. Last year, I dedicated most of my reading to understanding race in America. I’ve ranked the most impactful books in this article. Reading without action is fairly meaningless. But it’s challenging to do good if you don’t understand the basics. If you’re up for doing the work, the books below are a good start. (1) The Fire Next Time by James Baldwin; (2) White Fragility: Why It’s So Hard for White People to Talk About Racism by Robin DiAngelo; (3) Why Are All the Black Kids Sitting Together in the Cafeteria?: And Other Conversations About Race by Beverly Daniel Tatum; (4) Just Mercy by Bryan Stephenson; (5) The Color of Law: A Forgotten History of How Our Government Segregated America by Richard Rothstein. Read the article to see the full list. Forbes (10 minutes)

Mark Benioff / CEO, Salesforce

I didn’t agree with Friedman then, and the decades since have only exposed his myopia. Just look where the obsession with maximizing profits for shareholders has brought us: terrible economy, racial and health inequalities, and the catastrophe of climate change. It’s no wonder that so many young people now believe that capitalism can’t deliver the equal, inclusive, sustainable future they want. It’s time for a new kind of capitalism—stakeholder capitalism, which recognizes that our companies have a responsibility to all our stakeholders. Yes, that includes shareholders, but also our employees, customers, communities and the planet. New York Times (32 minutes)

The New Breed

The New Breed—The Rise of the Social Entrepreneur is a new feature documentary, which I’m proud to be a part of. The film captures the journey of three compelling millennials as they start businesses to tackle social and environmental issues, including poverty, homelessness and environmental pollution. It also includes seven short sketches, which illuminate the global forces that have triggered the Social Enterprise movement, tackling topics like colonialism, inequality and “the history of poverty” in simple, fun and easy-to-understand ways. Here’s an exclusive look at the sketch I’m in, tackling the subject of The Profit Motive. The full documentary is available for free, for six more days. Please check it out and help us spread the word by sharing the link with your family and friends. Let me know what you think. newbreed.tv (79 minutes)

Life Skills

Here are three important life skills that you were probably never taught: (1) How to stop taking things personally. We tend to have an inherent bias toward assuming that pretty much everything that happens to us is actually about us. But here’s a newsflash: Just because you experience something, just because something causes you to feel a certain way, just because you care about something, doesn’t mean it’s about you. When people criticize you or reject you, it likely has way more to do with them—their values, their priorities, their life situation—than it does with you. I hate to break it to you, but other people simply don’t think about you that much (after all, they’re too busy trying to believe everything is about them). (2) How to be persuaded to change your mind. You’re going to be wrong a lot in life. In fact, you’re going to be wrong pretty much all of the time. And in many ways, your ability to succeed and learn over the long term is directly proportional to your ability to change what you believe in response to your ignorance and mistakes. (3) How to act without knowing the result. We avoid moving and acting without knowing. And because we cannot act on what we don’t know, our lives become incredibly repetitive and safe. Mark Manson (15 minutes)

How to Think

No skill is more valuable and harder to come by than the ability to critically think through problems. And schools don’t teach you a method of thinking, you have to do the work yourself. Those who do it well get an advantage, and those that do it poorly pay a tax. So, how do you learn to think? Stop multitasking; it impairs your ability to think. Thinking means concentrating on one thing long enough to develop an idea about it. Don’t learn other people’s ideas or memorize a body of information, however much those may sometimes be useful. Develop your own ideas. In short, think for yourself. You simply cannot do that in bursts of 20 seconds at a time, constantly interrupted by Facebook messages or tweets, or fiddling with your iPod, or watching something on YouTube. It’s only by concentrating, sticking to the question, being patient, letting all the parts of your mind come into play, that you arrive at an original idea. By giving your brain a chance to make associations, you may draw connections that take you by surprise. Farnam Street (5 minutes)

First Principles

A first principle is a basic assumption that cannot be deduced from any other assumption. In Mathematics, these are called axioms. First principles are the Lego building blocks for thinking. These Lego blocks, once carefully assembled with forethought, are reusable. With the right set of first-principles, you can start mixing them in ways you couldn’t before, allowing you to think better and faster. Choosing the right set of Lego blocks for your thinking is the key, and it’s harder than it may seem. This in-depth guide is a great resource to learn first principles thinking. The Ultimate First Principles Guide (5 hours)

Success v. Happiness

Success resembles addiction in its effect on human relationships. People sacrifice their links with others for their true love: success. They travel for business on anniversaries. They miss Little League games and recitals while working long hours. Some forgo marriage for their careers—earning the appellation of being “married to their work”—even though a good relationship is more satisfying than any job. Many scholars, such as the psychologist Barbara Killinger, have shown that people willingly sacrifice their own well-being through overwork to keep getting hits of success. I know a thing or two about this: As I once found myself confessing to a close friend, “I would prefer to be special than happy.” He asked why. “Anyone can do the things it takes to be happy—going on vacation with family, relaxing with friends … but not everyone can accomplish great things.” My friend scoffed at this, but I started asking other people in my circles and found that I wasn’t unusual. Many of them had made the success addict’s choice of specialness over happiness. They (and sometimes I) would put off ordinary delights of relaxation and time with loved ones until after this project, or that promotion, when finally it would be time to rest. The pursuit of achievement distracts from the deeply ordinary activities and relationships that make life meaningful. The Atlantic (8 minutes)


Interesting things happen when you do interesting things. It’s an equation, an unwritten law and a universal truth all rolled into one. It’s a way at looking at each day, at each opportunity, each time you meet someone. (1) Outputs are directly related to inputs. If you go looking in the same place for inspiration as everybody else, you will find your work quickly resembles theirs. Go see that odd Polish subtitled movie. Be one of the three in the audience. (2) Comfort zones are creative dead zones. To feel most alive, you have to be doing work that keeps you on your toes. Once you have your successful formula, don’t repeat it. Start again, but start from a new place. Having doubts about your work means you are trying new ways. (3) Listen. The best way to be interesting is to be interested. Stop being on transmit, and flip the switch to being on receive. Listen hard, listen without thinking about what you are about to say. Good listeners are sought after. (4) Treat failure as a rite of passage toward interesting. How you view failure will determine how much success you have. If you fear it, you will hold back. And if you hold back, you will not be brave with your ideas. Ideas require you to be at your bravest in order to stand out. (5) Fallow. In order to be fertile with ideas, sometimes you have to rest. Take a break. Farmers know this. They know you have to rest a field. Put it back, so it can give again. You are not a machine. Creativity comes in sprints after a rest. Do Lectures (11 minutes)

Unbelievable, But True 

Sometimes you come across a Twitter thread that’s so good, you can’t not share it. @adribbleofink posted this tweet on Jan 3: Tell me a story about yourself the [sic] sounds like a lie but is absolutely true. The responses were endlessly entertaining and some blew my mind. Enjoy going down the rabbit hole. Twitter (30 minutes)


Just for fun. Here’s one of the most athletic things I’ve seen in a while. Watch Olympian Katie Ledecky swim with a full glass of milk on her head. Cnet (1 minute)

The Year in Pictures

Certain years are so eventful that they are regarded as pivotal in history, years when wars and slavery ended and deep generational fissures burst into the open—1865, 1945 and 1968 among them. The year 2020 will certainly join this list. It will long be remembered and studied as a time when more than 1.5 million people globally died during a pandemic, racial unrest gripped the world, and democracy itself faced extraordinary tests. The photographs in this collection capture those historic 12 months. Jeffrey Henson Scales, who edited “The Year in Pictures” with David Furst, said he had never felt such sweep and emotion from a single year’s images—from the “joy and optimism” of a New Year’s Eve kiss in Times Square, to angry crowds on the streets of Hong Kong and in American cities, to scenes of painful debates over race and policing, to the “seemingly countless graves and coffins across the globe.” But two pictures taken in late January in Wuhan, China, are hints of a larger cataclysm to come. In one aerial shot, construction workers are building a giant hospital virtually overnight to handle hundreds of patients stricken with the coronavirus. The other looks like a still from a sci-fi film: A man dressed in black, wearing a white mask, lies dead on a city street; two emergency workers have stepped away from him and gaze at the viewer—all but their eyes hidden by face coverings and ghostly white protective suits. New York Times (19 minutes)

The Great Realization

This is a bedtime story of how the coronavirus changed the world, how it might change our perspective and why hindsight’s 2020. Get your tissues ready. YouTube (4 minutes)


This video for the song Telephone from The Brilliance is simple and powerful. The song is about loss during the Coronavirus. The visuals follow a healthcare worker dancing in the empty streets of LA. Check it out. YouTube (3 minutes)


Every week in this Bookshelf section I share what I’m reading. For the final entry, I’ve decided to list all of the books I read in 2020 along with a rating and short description. See what I read here.

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 Dave Hoefler.

Should We Work Together?

This newsletter is my passion project. I hope it helps you gain deeper insight and equips you to create meaningful impact in the world. Many readers have asked about how we can work together. In case you’re interested, I run a law firm for startups. We try to keep things simple by offering transparent flat fees. We structure our engagements in two ways: (1) Per-project flat fee engagements—No billable hour means no surprise legal bills. (2) General Counsel—A simple monthly fee for all your day-to-day legal needs. It’s like getting a subscription to your own general counsel. If you’re interested, let’s jump on a call to see if you’re a good fit for the firm. Click here to schedule a call.

Weekend Wisdom

I hope that in this year to come, you make mistakes. Because if you are making mistakes, then you are making new things, trying new things, learning, living, pushing yourself, changing yourself, changing your world. You’re doing things you’ve never done before, and more importantly, you’re Doing Something.Neil Gaiman

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