The Insider - August 2024

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Welcome to the August edition of the Insider. Do you know someone who would enjoy the Insider? Forward this email to them and they can subscribe here.

The new media landscape

From the 1950s to the 1980s, the “big three” broadcast networks—NBC, CBS, and ABC—were in every household. People consumed the same news and watched the same shows. But today, the digital information space is fragmented into millions of niches. For example, the most viewed videos on TikTok in 2023 racked up hundreds of millions of views, but it’s likely you never saw them (the top 10 list includes a strange mix of makeup routines, cat videos, ASMR, and “pottery blunders”). When Netflix released its most popular show during the first half of 2023, some TV critics had never heard of it.

The digital spaces that reinforce our shared sense of collective identity have been obliterated into tiny pieces. Brian Morrissey, an independent journalist covering the evolution of media, wrote, “As media decentralizes into millions of niches it makes it harder to build mass brands and maintain the growth of legacy mass brands.” What our algorithms serve up to us creates the illusion of consensus, but it’s just the consensus of a narrowly-defined audience. People across the street could be experiencing a completely different digital reality.

The unbundling of mass media presents a new wave of opportunity for next-generation media companies: independent journalists are leaving major newsrooms so they can make more money on Substack. Brands like Feastables, a snack company owned by MrBeast, represent a new go-to-market strategy for a company: plug into an existing audience with an audience co-founder. Two-person newsletters with just 35,000 subscribers can become 8 figure businesses.

The internet has always been a place where entrepreneurs can make a living with only a thousand true fans. The difference today is that the center of mass media is collapsing, and there will be major businesses built in entirely alternate realities. The warping of our collective consciousness is both dangerous and full of opportunity. 

Founder mode vs. Manager mode

Last week, Paul Graham, the startup and investing guru, published an essay called “Founder Mode.” The essay suggests that how we think about running large companies is wrong. For years, founders have been told “what got you here won’t get you there.” They need to hire good people, delegate responsibility, and get out of the way so the company can reach its full potential. But Graham speculates that this approach, labeled manager mode, can lead to a bloated bureaucracy and a meandering strategy. Better, Graham argues, to return to founder mode, or the mode of a company’s earliest days, when founders were deeply involved in the details, held high standards for themselves, and didn’t delegate too quickly.

Graham’s essay has sparked both introspection and pontification from entrepreneurs about what mode they’re in, what mode is best, and how to switch from one to the other. The idea that you’re in the wrong mode is a beguiling idea for the leader looking to find an edge.

If only the secrets of great leadership could be unlocked by cleanly switching from one mode to the next. The practice of leadership is so damn hard because it requires threading the needle between modes: holding high standards while empowering people, caring about the details while observing when the conditions are right to delegate, and having the confidence and self-awareness to know when to step in while having the humility to know when to step out. Underneath any mode, the real work is between you and yourself.

Living in a small story

There is this personal finance podcast called I Will Teach You To Be Rich that interviews couples about their personal finances. It’s great entertainment in a voyeuristic kind of way. The host, Ramit Sethi, asks the couple to share their real income and net worth numbers, and then he works with them to tackle a core personal finance challenge they’re facing.

If there is a theme across the episodes I’ve listened to, it's that while many couples are obsessed at optimizing for the short-term, they are missing out on defining a vision for their future. They’re far better at being the general contractors of their life than they are at being lifestyle architects. They optimize their credit card points, they comparison-shop at the grocery store, they hunt relentlessly for coupon codes online, they spin up side hustles to make extra income. But when you ask them what it’s all for, they don’t have good answers. They come onto a personal finance podcast looking for tactics and strategies, but the real problem is much deeper: a failure of imagination. This is the dangerous undertow of a busy life: by optimizing for all of the short-term decisions and near-term goals, we cannibalize our time and miss out on the larger choreography of designing a life we know we’ll love.

What I am reading

• How migrants are navigating the Darién Gap between Colombia and Panama. Once considered an impassable stretch of jungle, now hundreds of migrants brave it every day on their march north. The Atlantic.
• The rise of online-only churches in Kenya where preachers are using social media to reach the masses. The frontier of tech and faith. Rest of the World.
• The surge of venture capital dollars going into the US defense sector marks one of the largest investments in defense since WWII. How Silicon Valley sees war on the horizon with China. Wall Street Journal.
  • Pair with this lengthy but fascinating profile of Palmer Luckey, founder of Anduril.
• Seven days of garbage. In this photographic essay, photographer Gregg Segal asked people to save their trash for one week, and then lie down in it for a photograph. Gregg Segal. (Make sure to scroll.)
• Does America have too many laws? Congress has adopted an average of 344 new pieces of legislation each session, or 2-3 million words of new federal law each year. The Atlantic (by Supreme Court Justice Neil Gorsuch).

Something personal

In my teens, I caddied every summer at the local golf course. In the beginning at 14 years old, I barely knew what to do other than to follow my golfer around. I was paid accordingly, sometimes waiting for my mom to pick me up at the end of long round with only one $20 bill buried safely in my pocket. 

One day, when I had mismanaged things so poorly around the putting green, I was pulled aside by my golfer and educated about the etiquette and duties of a caddy. I’ll never forget his name or even the hole I was on; those 2-minutes of mentorship set me on a course to become a much better caddy and a more confident teenager in the company of older men.

Over the years, I caddied for hundreds of men (nearly all men, as few women wanted a caddy). I caddied for famous people and billionaires, gentlemen and cheats. As a teenage boy, it was an education in masculinity. On the golf-course, some men are at their most base, vulgar selves. Others were harsh bosses and stingy tippers. Some men embodied an integrity and kindness I’ll never forget. 

A foursome of golfers is a kind of half-day improv exercise: men performing for each other, gauging their rank in the pecking order, seeking to impress and vie for the respect of their fellow golfers. It is a stage upon which men act out their idea of what it means to be a man. 

I took it all in. What kind of masculinity felt true to me? What kind of man did I want to be? All this caddying, I soon realized, was a crash-course to figure out these existential questions.

Today, young men are also trying to find their solid ground. After years of identity politics, it is no surprise that competing definitions of masculinity have become politicized. An article in The New York Times examined the rise of masculinity politics. New York Magazine has an article about “the nice men on the Left” and the election between “two very different kinds of guys.”

The idea that there are “two very different kinds of guys” is a reductive, unfortunate binary when masculinity is a wide-reaching kaleidoscope. Too often we push men into these typecast roles, and their masculinity becomes a theatrical production instead of a genuine expression.

After many rounds of caddying and many rounds of therapy, I don’t worry as much anymore about performing my identity. But I do still have compassion for that younger self: working so hard in those hot summers, intimidated by the need to grow up and eager to find my own solid ground.

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From home,

Banks