Weekend Briefing No. 377

Welcome to the weekend and welcome to May! Here is my May playlist for your listening enjoyment.

I’m always trying to experiment with new ways to make the Weekend Briefing more engaging for you. This week, I’m trying not one, but two new things.

First, sometimes when I write an article (even an article I’m proud of), I think that the interview was so much richer. This was the case with my interview with Kevin Jorgeson. He’s such an interesting guy and we had such a good conversation, I posting the full interview (as well as topical segments) on YouTube. I think you’ll really like it.

Secondly, I’m including a new section called Feedback Loop. The idea with the section is that I will pose a question to you, then you’ll click through to a Google Doc and answer the question as well as comment on other reader’s comments.

Shoot me an email to let me know if you like / don’t like these two experiments as well as how you think they could be improved. Thanks.

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Prime Numbers

90 billion—Apple had an insane Q1. Sales were up 54% to $90 billion, a record for the January to March quarter. Profit more than doubled to $24 billion, notably higher than Wall Street expected.

1,800—In 2021 alone, 1,800 containers have fallen overboard off of large container ships, a pace that would make this year even worse than 2020, when 3,112 containers fell off ships.

0—In all of the calendar year 2020, police in Newark, New Jersey fired 0 shots. For the first time on record, the city did not pay a cent to settle police brutality cases.

Climbing & Entrepreneurship

What does climbing a massive wall in Yosemite have to do with running a startup? More than you might think. I had the honor of interviewing one of the best climbers of our generation – Kevin Jorgeson – for my most recent Forbes article. Entrepreneurs will find that the same mindset that allowed Jorgeson to rise to the challenge of climbing the Dawn Wall – the most challenging big wall climb in history – will help them navigate the challenges that are common to all founders. Here are four lessons on entrepreneurship from this world-class climber: (1) By the very nature of entrepreneurship, ambition will exceed the ability of the founders. Founders start with a sense of belief, but it takes the confidence derived from incremental progress to build a successful company. (2) The Trough of Sorrow does not need to be sorrowful. Zoom your perspective from the macro to the micro. Build in a ritual of recognizing the micro successes of the day. (3) Strong partnerships are complimentary, built on trust and prioritize objective over ego. (4) When you’re in especially challenging moments, remember this is supposed to be difficult. Embrace the struggle, and see it as an opportunity to learn what you’re really capable of. Forbes (12 minutes)

Kevin Jorgeson Interview

One thing I find is that no matter how much I work on an article, there are often so many great sections that get cut. So, I decided to invite you to sit in on the conversation. I know you all want to be in the (zoom) room where it happens. In addition to being a climber Kevin is also an entrepreneur, an advocate, a husband and a father. In this wide ranging conversation we discuss on all of that. The overarching theme in this conversation is what it means to live a life where ambition exceeds ability, which is as important for climbing as it is for entrepreneurship. It was such a great conversation, I hope you enjoy it, while you’re there, please subscribe to my channel on YouTube. I’m going to be doing more of this.

Full Interview (94 minutes)

Belief v. Confidence (4 minutes)

Laboring in Obscurity (8 minutes)

Partnership (9 minutes)

Pitch 15 on the Dawn Wall (12 minutes)

The Fun Scale (6 minutes)

What Am I Capable Of? (7 minutes)

Fatherhood (5 minutes)

Reinvention (10 minutes)

Fear (8 minutes)

What’s Your Dawn Wall (6 minutes)

YOLO Economy

Something strange is happening to the exhausted, Type A millennial workers of America. After a year spent hunched over their MacBooks, enduring back-to-back Zooms in between sourdough loaves and Peloton rides, they are flipping the carefully arranged chessboards of their lives and deciding to risk it all. Some are abandoning cushy and stable jobs to start a new business, turn a side hustle into a full-time gig, or finally work on that screenplay. Others are scoffing at their bosses’ return-to-office mandates, and threatening to quit unless they’re allowed to work wherever and whenever they want. They are emboldened by rising vaccination rates and a recovering job market. Their bank accounts, fattened by a year of stay-at-home savings and soaring asset prices, have increased their risk appetites. And while some of them are just changing jobs, others are stepping off the career treadmill altogether. If this movement has a rallying cry, it’s “you only live once,” or “YOLO”—an acronym coined by rapper Drake. If “languishing” is 2021’s dominant emotion, YOLOing may be the year’s defining work force trend. A recent Microsoft survey found that more than 40 percent of workers globally were considering leaving their jobs this year. New York Times (12 minutes)

Goodhart’s Law

Goodhart’s Law is simple: When a measure becomes a target, it ceases to be a good measure.  An oft-cited example of Goodhart’s Law in action is the bounty on cobras that the British who ruled India supposedly paid to try to reduce the population of the snakes. Enterprising Indians quickly figured that they could earn money by raising cobras to kill and present for bounties. Likewise when Soviet planners ordered nail factories to increase the number of nails they produced, it’s said that managers reacted by producing millions of tiny, useless nails. When the planners wised up and switched to a weight criterion, the factories started producing giant, heavy and equally useless nails. A new problem area is artificial intelligence and machine learning. Human beings are good at exploiting Goodhart’s Law, but computers are even better. For example, a deep neural network that was intended to detect pneumonia in chest scans did well overall, but failed on scans coming from new hospitals. It turned out that the system had taken a shortcut: Instead of looking at the scans, it zeroed in on the names of the hospitals where the scans came from. Because certain hospitals had higher rates of pneumonia, artificial intelligence was able to achieve a reasonably good prediction—without learning much about pneumonia at all. Bloomberg Businessweek (9 minutes)

Changes at Basecamp

This week, the founders of Basecamp, a company that makes project management software, made a company-wide announcement about some changes that they are making. (1) No more societal and political discussions. Today’s social and political waters are especially choppy. Sensitivities are at 11, and every discussion remotely related to politics, advocacy or society at large quickly spins away from pleasant. You shouldn’t have to wonder if staying out of it means you’re complicit, or wading into it means you’re a target. These are difficult enough waters to navigate in life, but significantly more so at work. It’s become too much. It’s a major distraction. And we’re done with it. (2) No more paternalistic benefits. For years, we’ve offered a fitness benefit, a wellness allowance, a farmer’s market share and continuing education allowances. It’s none of our business what you do outside of work, and it’s not Basecamp’s place to encourage certain behaviors—regardless of good intention. We recently introduced a 10% profit-sharing plan to provide direct compensation that people can spend on whatever they’d like, privately, without company involvement or judgement. (3) No more committees. (4) No more lingering or dwelling on past decisions. (5) No more 360 reviews. (6) No forgetting what we do here. We make project management, team communication and email software. We are not a social impact company. Our impact is contained to what we do and how we do it. We write business books, blog a ton, speak regularly, open-source software and give back an inordinate amount to our industry, given our size. And we’re damn proud of it. Our work, plus that kind of giving, should occupy our full attention. We don’t have to solve deep social problems, chime in publicly whenever the world requests our opinion on the major issues of the day, or get behind one movement or another with time or treasure. These are all important topics, but they’re not our topics at work—they’re not what we collectively do here. Employees are free to take up whatever cause they want, support whatever movements they’d like, and speak out on whatever horrible injustices are being perpetrated on this group or that (and, unfortunately, there are far too many to choose from). But that’s their business, not ours. We’re in the business of making software and a few tangential things that touch that edge. We’re responsible for ourselves. That’s more than enough for us. Basecamp (13 minutes)

Feedback Loop

So, here’s my question for you: Do you agree / disagree with Basecamp’s approach here? Why? Should companies be expected to have a social impact beyond the goods / services they deliver? Answer here.

U.S. Healthcare Is Not a Free Market

The beauty of a basic free market interaction—at, say, a local barber—is that the business and customer incentives are entirely aligned. To get more of what it wants (revenue), the barbershop needs loyal customers—something that only happens when people have a good experience at the shop and leave with a haircut they like, at a price they think is reasonable. But the convoluted U.S. healthcare system screws up that alignment. Sure, doctors get paid when patients choose to use their services. However, there are two middlemen who distort that relationship, as a majority of the doctor’s actual payment comes from the insurer (who also negotiates the prices), and the insurer gets a majority of its payments from the employer. The patient is so far removed from the doctor, financially, that the various prices for the doctor’s services aren’t even available to the patient—they’re treated more like proprietary back-office info that’s none of the patient’s business. While there’s still some element of consumer choice and competition, the typical patient’s limited in-network options and the lack of transparency when comparing those options significantly dilutes this powerful motivator. Mostly, the system’s fee-for-service model incentivizes doctors to see a high volume of patients, even if it comes at the expense of quality. American patients aren’t treated like customers because they’re not customers. Once you consider this, the typical American patient’s experience makes much more sense. Some obvious factors include the following: the wait time for an appointment (24 days on average in the U.S.); inconvenient open hours; the lack of basic modern conveniences for some doctors (I make my haircut appointments online but have to call the doctor’s office and listen to hold music); the stereotypically long waits on the day of the appointment (often because many doctors book two patients for every time slot); the lack of any follow-up after an appointments; or any sophisticated way for patients to access their history and analyze trends. Wait But Why (18 minutes)

Depression and Faith

Michael Gerson, national columnist, gave a powerful talk at the Washington National Cathedral about his depression and his faith. Here’s what he had to say: All of us—whatever our natural serotonin level—look around and see plenty of reason for doubt, anger and sadness. A child dies, a woman is abused, a schoolyard becomes a killing field and a typhoon sweeps away the innocent. If we knew or felt the whole of human suffering, we would drown in despair. However, the answer to the temptation of nihilism is not a philosophical argument. It is the experience of transcendence we cannot explain, or explain away. Gerson had one such moment walking in the Bishop’s Garden at the Washington National Cathedral. This experience of pulling back the curtain of materiality, and briefly seeing the landscape of a broader world, comes in many forms. It can be religious and nonreligious, Christian and non-Christian. But there is this difference for a Christian believer: At the end of all our striving and longing, we find a not a force—but a face. All language about God is metaphorical. But the metaphor became flesh and dwelt among us. In times of sorrow, many, understandably, pray for a strength they do not possess. But God’s promise is somewhat different: That even when strength fails, there is perseverance. And even when perseverance fails, there is hope. And even when hope fails, there is love. And love never fails. Washington Post (8 minutes)


Effortless by Greg McKeown. As high achievers, we’ve been conditioned to believe that the path to success is paved with relentless work. If we want to overachieve, we have to overexert, overthink and overdo. If we aren’t perpetually exhausted, we’re not doing enough. But lately, working hard is more exhausting than ever. And the more depleted we get, the more effort it takes to make progress. Stuck in an endless loop of “Zoom, eat, sleep, repeat,” we’re often working twice as hard to achieve half as much. Getting ahead doesn’t have to be as hard as we make it. No matter what challenges or obstacles we face, there is a better way: Instead of pushing ourselves harder, we can find an easier path. The effortless way isn’t the lazy way. It’s the smart way. It may even be the only way. Not every hard thing in life can be made easy. But we can make it easier to do more of what matters most. Amazon

Most Read Last Week

Racket—There’s a new social network for short-form audio that I think is really interesting. Think about what Twitter did for blogs. Racket is doing the same for podcasts. It’s a platform that allows anybody to produce and post audio content (solo or a group conversation) simply and quickly. Each post or “racket” is a maximum of nine minutes in length. Check it out. Grab your name. Get on the waitlist. Follow me on Racket.

The Crypto State—What if all contemporary states are in the process of being replaced by a new kind of “state,” as different from existing governments as they themselves differed from ancient empires or primitive tribes?

Próspera—This post is a digest on Próspera from basically every public source, plus some non-public ones. It’s about a private tech city and a prosperity vision and all that. But it’s also about “systemic change.”

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 Gradienta.

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

If it isn’t a clear yes, then it’s a clear no. Greg McKeown

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