Weekend Briefing No. 356

Welcome to the weekend.

If you know me, you might know that I’m really into Christmas music. I’m also incredibly legalistic about it—no Christmas music until after Thanksgiving. There are rules, people!

Anyhow, here’s my Ultimate Christmas Playlist. I’ve refined it over the years. I hope it brings you holiday cheer this month.

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Prime Numbers

1—Digital advertising is projected to make up more than 50 percent of total ad spend for the first time ever: an expected $110.1 billion of the $214.6 billion total U.S. forecast (excluding political ads).

36—Data suggests between 19 and 36 percent of all air trips are likely to be permanently lost, even after the economy returns to “normal” since more meetings are shifting to screens.

3.2It seems that scented candles are an unexpected victim of the pandemic. Since March, the average rating of the top three scented candles on Amazon dropped from 4.3 to 3.2.


Eight years ago, almost to the day, I touched down in Las Vegas. I was there at the invitation from a friend Amanda Slavin who was curating the first Catalyst Week in Downtown Las Vegas (DTLV) on behalf of Tony Hseih. Tony had a massive vision for revitalizing Downtown Las Vegas, which included intellectual and cultural programming. So, he invited 22 “young innovators” to give TED style talks. Tony was an incredibly warm and welcoming host. But he was never one to take center stage, ever content to listen and observe. I had my first taste of Frenet with Tony at his apartment that week. (That drink is inextricably linked to him in my mind.) The idea was that the people living in DTLV would come, listen and be inspired by our talks. However, I suspect the talks we all fretted over didn’t have much impact on the audiences’ lives. But, that was kinda beside the point. The point was building our own community. Looking back, that week was such a pivotal moment in the formation of my community – my tribe. Amanda really knew how to select a group of speakers. I either met or truly bonded with a number of my closest friends in life that week. This week since Tony’s passing I’ve been reading and listening to stories from people he touched and it made me realized that my story is nothing special; that thousands of people have similar stories. It dawned on me that his legacy is community. What a powerful legacy – creating the context where deep relationships are formed. His legacy is an inspiration to me. I only hope that when all is said and done, I will be known for building community as well. If I can do it on a fraction of a scale that he did, it will be a life well-lived. To read more about Tony, I’d recommend this piece from one of Tony’s closest friends Albert Lin. Forbes (7 minutes)

Independent Thinking

Can you make yourself more independent-minded? I think so. This quality may be largely inborn, but there seem to be ways to magnify it, or at least not to suppress it. Paul Graham has some thoughts on how: (1) One of the most effective techniques is one practiced unintentionally by most nerds: simply to be less aware of what conventional beliefs are. (2) It matters a lot who you surround yourself with. If you’re surrounded by conventional-minded people, it will constrain which ideas you can express, and that in turn will constrain which ideas you have. But if you surround yourself with independent-minded people, you’ll have the opposite experience: hearing other people say surprising things will encourage you to, and to think of more. It’s enough to have one or two you can talk to regularly. And once you find them, they’re usually as eager to talk as you are; they need you too. (3) Adopting a stance of skepticism. When you hear someone say something, stop and ask yourself “Is that true?” Treat it as a puzzle. You know that some accepted ideas will later turn out to be wrong. See if you can guess which. The end goal is not to find flaws in the things you’re told, but to find the new ideas that had been concealed by the broken ones. PaulGraham.com (17 minutes)

Life-Changing Questions

Speaking of independent thinking, what questions are you asking that were previously unimaginable? What questions changed your life? Unfinished believes that questions can shine a path forward, and instigate the change we seek. Join me at 7 p.m. ET/ 4 p.m. PT on Tuesday, December 8th, for the final episode of Unfinished Live: Questions, Culture & Change. Dig deeper into why questions matter and what questions inform the lives and art of guests like Bruce Springsteen, Precious Okoyomon, Hans Ulrich Obrist, Gina Belafonte. In addition to interviews and short films, host Baratunde Thurston will be back to engage the audience in an interactive, reflective experience geared toward action. RSVP at Unfinished. (Sponsored)

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)

AI Love Stories

GPT-3, the latest incarnation of artificially intelligent natural-language systems, knows how to write—and write and write and write. For a taste of what it can (and cannot) do, here are three examples of its verbosity. In each case, the Times staff gave the system a short prompt (in italics) and let it roll. First, they asked it to write about itself. Then, they asked the system to write a Modern Love column. It wrote dozens; like all romances, some turned out better than others. They fed the system no information beyond the initial prompt; its writing is based on the thousands of websites, Wikipedia articles and self-published books it has metabolized during months of training. Except for the titles, the entries are entirely unedited. See what the outcome is. New York Times (11 minutes)

Pricing & Fairness

One of the biggest challenges for startups is learning how to price a novel product. Dan Arieli argues that pricing is not about value, it’s about fairness. He met with a bank that said they were going to remove ATM fees to withdraw money. They thought that customers would love them. He said, “Actually, they’ll hate you. If you just reduce the price to free, you’re basically telling people we could have charged you nothing all along, we just didn’t.” And that would create tremendous anger because of fairness—not because the service is not worth $2.50, but because of fairness. Instead he suggested that the bank tell people: “Look, it really costs us $2.50 to provide you with this service but if you don’t have the money to pay for it, pay us less. It’s up to you.” I basically used the name-your-own-price approach. This way, you don’t have to go to zero. The worst that can happen is that people will pay you nothing—but critically, you’re not communicating to people that this costs you nothing. NFX (22 minutes)

Touched by Others’ Pain

Pope Francis wrote an op-ed on the coronavirus. These words struck me: If we are to come out of this crisis less selfish than when we went in, we have to let ourselves be touched by others’ pain. There’s a line in Friedrich Hölderlin’s Patmos that speaks to me, about how the danger that threatens in a crisis is never total; there’s always a way out: “Where the danger is, also grows the saving power.” That’s the genius in the human story: There’s always a way to escape destruction. Where humankind has to act is precisely there, in the threat itself; that’s where the door opens. This is a moment to dream big, to rethink our priorities—what we value, what we want, what we seek—and to commit to act in our daily life on what we have dreamed of. God asks us to dare to create something new. We cannot return to the false securities of the political and economic systems we had before the crisis. We need economies that give to all access to the fruits of creation, to the basic needs of life: to land, lodging and labor. We need politics that can integrate and dialogue with the poor, the excluded and the vulnerable, that gives people a say in the decisions that affect their lives. We need to slow down, take stock and design better ways of living together on this earth. New York Times (8 minutes)


Conspiracy by Ryan Holiday. In 2007, a short blogpost on Valleywag, the Silicon Valley vertical of Gawker Media, outed PayPal founder and billionaire investor Peter Thiel as gay. Thiel’s sexuality had been known to close friends and family, but he didn’t consider himself a public figure, and believed the information was private. This post would be the beginning of a meticulously plotted conspiracy that would end nearly a decade later with a $140 million dollar judgment against Gawker, its bankruptcy and with Nick Denton (Gawker’s CEO and founder) out of a job. Only later would the world learn that Gawker’s demise was not incidental—it had been masterminded by Thiel. Amazon

Most Read Last Week

Life Skills—These are three important life skills that you were probably never taught.

Distributed Communication Rules—Basecamp has a guide to internal communication. They’ve been working remotely for years. This is what they think is meaningful.

Pandemic Fatigue—Pandemic fatigue: it’s plaguing organizations and employees right now.

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 Arsene M Øvrejorde.

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Weekend Wisdom

The best place to find undiscovered ideas is where no one else is looking. Paul Graham

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