Weekend Briefing No. 456

Welcome to the weekend.

This month’s playlist is more pop-focused, including three of my favorite tracks from Taylor Swift’s new album: Anti-Hero, Snow on the Beach and Vigilante Sh*t. Enjoy my November playlist. Cheers! 

Also, thanks to everybody who applied to sponsor the Weekend Briefing in 2023 last week. We sold out the entire year in a matter of hours. I’m looking forward to these upcoming partnerships.

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Prime Numbers

8 million—Every year, 8 million tons of leaves are put into plastic bags and sent to landfills. When sent to landfills, the leaves don’t have enough oxygen to properly decompose and will release a considerable amount of methane.

46%—The U.S. tattoo market is estimated to be worth $1.5 billion this year, up 8.4% over the past five years. Today, 46% of Americans have tattoos.

10—Taylor Swift becomes the first artist to claim all top 10 spots on Billboard’s Hot 100 songs chart; all 13 songs from her “Midnights” album rank in the top 15.


If you’ve been a reader for a while, you know I’m a huge Bono fan. He has a new book out called Surrender that you should check out. The audiobook is so much better than a hard copy. Trust me. I’ve been watching a lot of his interviews this week as he’s promoting the book, but this one from NPR is my favorite. Here are some of the best lines: (1) On relationships: The most consequential decision of his life was asking a girl named Alison Stewart out. It was the same week that he met his bandmates. He’s still together with his wife and his band. “If I wasn’t with Ali, I wouldn’t still be with Edge, Adam and Larry.” (2) On faith: “The scriptures remain a plumb line for me to gauge how crooked the wall of my ego has become.” (3) On surrender: “To surrender to my band. Surrender to my wife. Surrender to my Maker. These are not things that are easy [for] me. And I wanted to write that. I want to someday surrender totally.” YouTube (17 minutes)

Recessions and Riptides

Dealing with a recession as an entrepreneur is tough. (I’ve been through a few myself. I know.) The typical instinct is to buckle down and work harder. Khe Hy notes that the brute-force approach to this situation is largely driven by fear of irrelevance, fear of the death of ego and a desire for safety. These can drive us to overwork and cause us to thrash. But thrashing will likely have a detrimental effect. Maybe we should take a lesson from Bono and learn to surrender. Just like when you’re caught in a riptide, if you thrash around and try to fight the tide, you’ll tire out quickly and risk drowning. Instead, surrender and allow the current to take you out to sea. As the current dissipates, you can then effortlessly swim parallel to the shore, out of the riptide and back to safety. RadReads (6 minutes)

His Given Name Was Clippit

The last time you used a new mobile app, you probably had an amazing onboarding experience without even realizing it. Apps teach us how to use them with quick, simple, seamless guidance (and great UX). So why does B2B software still feel like Clippy is about to pop up in the corner and ask if you need help? Here are three lessons B2B companies can (and should) take from B2C customer onboarding. Glance (Sponsored)


Web3 technology, the next phase of the internet, will be owned by the creators and users of the network as opposed to centralized corporations or governments. This represents a tectonic shift in entrepreneurship and community building. VenturePunk is a venture studio that aims to ideate, validate, get traction and then scale new Web3 projects.​ We love working with this team and were excited to support their $1.5 million Pre-Seed round, which included investors like ConsenSys Mesh, Polygon Ventures, Bain Capital Crypto, Lemniscap, Polygon, The LAO and PunkDAO. Keep an eye out for the projects coming out of VenturePunk. VenturePunk (5 minutes)

American Dynamism

A Pew Research Forum poll recently asked Americans a popular political question: Will your children be better off than you will? Sixty-eight percent of Americans said no, putting the U.S. as the sixth-most pessimistic country in the survey. We are in pessimistic times. The antidote is American dynamism. It’s the recognition that seemingly insurmountable problems in our society—from national security and public safety to housing and education—demand solutions that aren’t simply incremental changes that perpetuate the status quo. These problems demand solutions from builders—and it’s never been more vital that startups tackle these serious American problems. American dynamism is for builders. It is the belief that the values upon which the country was founded are real and worth defending. Dynamism is also a feeling: the feeling of growth, movement, momentum and opportunity. It makes America the country people want to be from; to immigrate to; and to build a life, career or company in. Future (11 minutes)

Technology, Scarcity and Life

If the proximate purpose of technology is to reduce scarcity, the ultimate purpose of technology is to eliminate mortality. At first, that sounds crazy. But let’s start with the premise: Is the proximate purpose of technology to reduce scarcity? Think about how a breakthrough is described: faster, smaller, cheaper, better. Now for the second half of the sentence: the logical implication. Is the ultimate purpose of technology to eliminate mortality? Well, mortality is the main source of scarcity. If we had infinite time, we would be less concerned with whether something was faster. The reason speed has value is because time has value; the reason time has value is because human life has value, and life spans are finite. If you made life spans much longer, you’d reduce the effective cost of everything. Reducing scarcity is the proximate purpose of technology. Eliminating the main source of scarcity—namely mortality—is the ultimate purpose of technology. Therefore, life extension is the most important thing we can invent. Balaji Srinivasan (8 minutes)

Toddler or Tech CEO

Are you a parent of a toddler or an assistant to a tech CEO? (1) A disproportionate amount of your time is spent cleaning up messes and bringing him snacks. (2) He won’t stop talking about how he’s going to build a rocket ship and blast off into outer space. (3) He routinely overestimates his abilities. (4) He uses a lot of words that sound entirely made up. (5) He has a room filled with toys that he refers to as his “office.” (6) He never pays taxes. (7) He wants to be a unicorn. McSweeny’s (3 minutes)

Should We Work Together?

Hi! I’m Kyle. This newsletter is my passion project. When I’m not writing, I run a law firm that helps startups move fast without breaking things. Most founders want a trusted legal partner, but they hate surprise legal bills. At Westaway, we take care of your startup’s legal needs for a flat, monthly fee so you can control your costs and focus on scaling your business. 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 one-on-one call with me.

Weekend Wisdom

At the moment of surrender, I folded to my knees. I did not notice the passersby, and they did not notice me. Bono

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