NYC this week: Sunny every day, highs in the low-to-mid 60s, nights in the 40s. October’s being suspiciously nice. Pack a jacket and your feelings. Spent the weekend in Central Park with my kids. Felt like a 90's romcom.

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The number of the day: 2.9.

I met a guy in Hampton who sold a company for ~$10m in 2016. For the last decade his fulltime job has been buying individual public stocks.

His return: 21.8% a year. The S&P 500 did 13.5% over the same time. At most times he only owns 4-8 stocks.

Being that I’m a noisy sonuvabitch, I asked him to pull up his accounts so I could see the numbers (I use the excuse that I’m gathering this info to serve you, my dear reader. You’re welcome).

They were very good. His ~$10m is now worth ~$50m.

The returns are great. But the more interesting part came when we put his brokerage accounts into Claude and asked how many decisions he makes a year. A decision in his case means he’s either buying or selling a stock.

The answer was 2.9. And in some years, 0 decisions were made.

I find that interesting because we often correlate motion with good results. But for the average CEO or person with leverage, that isn’t the case.

Most people should not trade individual stocks. Index 4 life. But I love studying the decision making process of the rare ones who outperform the market. Ray Dalio, David Rubenstein, Lloyd Blankfein, Howard Marks. I’ve interviewed many billionaire stock pickers (Howard Marks is a bond picker, but close enough).

The successful ones have a few things in common that you, my fellow plebe, can apply to your life and business.

1. They make few decisions. “Lethargy bordering on sloth remains the cornerstone of our investment style,” Warren Buffett once said.

2. They don’t agonize over small decisions. Decisions are split into ones they can't undo and ones they can easily reverse. Most decisions are two-way doors and don’t deserve agonizing.

3. They know their circle of competence. They say “no” often. Not because something is good or bad, but because it's not within their area of expertise.

4. They write their big decisions down. Writing pre-mortems (imagine it's a year later and why the decision blew up) and writing their thought process before the decision. Then they review it after to see if their reasoning was good or bad.

Interestingly, I texted my 2.9-decision-a-year buddy as I was writing this post. I just got done writing the bit above about commonalities of good investors. I asked him how he makes his decisions:

“I study a few things I feel I can understand, and I study them very deeply. I keep very detailed notes and then just wait for an opportunity. [Company name] for example, I had studied extensively about 6 months prior to Covid and really liked it, it just was expensive. So I kept my notes and kept an eye on it. Then an opportunity showed up.”

Circle of competence. Write it down. Make a few decisions.

I'm a firm believer that virtually no one should buy individual stocks. It's almost impossible over a long run to outperform the market. But there are a few people who do. And I love studying those people because I'm curious about how they make decisions and deal with stress. Not because I want to go out and buy individual stocks, but because I want to apply it to my field.

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Last week: 9,080 of you opened (out of 32,832). Most clicked: Lenny Rachitsky's chill life (615), who's really rich in America (578), and Matt Paulson's $300m net worth (516).

So, in summary: you people love money and existential dread. Same.

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Cool stuff I’m consuming:

[Title of the piece] (article): [One or two sentences on why it's interesting.]

The Emptiness of Existence by Arthur Schopenhauer (essay): A 6-page essay from 1851 arguing we spend our whole lives waiting for the next thing and miss the thing itself. Bleak as hell. Also correct.

"We accept the present as something that is only temporary, and regard it only as a means to accomplish our aim. So that most people will find if they look back when their life is at an end, that they have lived their lifelong ad interim, and they will be surprised to find that something they allowed to pass by unnoticed and unenjoyed was just their life — that is to say, it was the very thing in the expectation of which they lived."

Buy the reference (eBay): Cool modern clothes are almost always replicas of a "reference," which is a cool old piece of clothing. Brands collect vintage stuff and remake it. Here's a cool hunting jacket from the 1930s. A lot of modern jackets are based on it. Buy the real old one. It's cooler and costs less. Speaking of, this YouTuber explains fabric in a way you can't NOT watch.

Should you sell or not (Reddit thread): A 42-year-old business owner on r/fatFIRE debating whether to sell his business (he'll make $10m). My take: sell to get your first $10m. For your next biz, maybe never sell (if you're growing). My friend Marshall had a business making $500k a month in profit. He sold. I did the math for you.​

Mega Mansions: Are they worth it? (video, 35:29): Something I've noticed with rich people: they spend more time with kids because they have a big house or vacation house that's comfortable for everyone. One of the few reasons why owning a big house is worth it. So, I interviewed a guy who made ~$60m when he exited his business, then built a 24,000 sq ft house. It cost ~$10m, ~$10k a month to keep up, and takes 5-10 hours of his week. Move-in day, in his words: "we looked at each other like what did we do."

Suicide rates highest ever among middle-aged men (Hacker News thread): Read the comments. Developers saying AI made their jobs, hobbies and careers feel pointless."Feels like all the effort I put into coming this far was invalidated overnight. … I used to enjoy programming as a hobby, writing articles. It's all so meaningless now. What's the point?" — HN user matheusmoreira

"Almost every form of social activity has dropped over the last 30 years except going to concerts" (tweet): When everything else moves to a screen, the stuff you can only do in person gets more valuable.

7 Powers by Hamilton Helmer (book): On My First Million, three or four multibillionaires have told me this is the best business book they've ever read. It breaks down the seven sources of durable advantage: scale economies, network economies, counter-positioning, switching costs, branding, cornered resource and process power.

What distinguishes the 1% from the merely affluent? (tweet): Having a third child. Big families are the new status symbol.

The most life-changing books, statistically (tweet): An awesome nerd looked at the books with the phrase "life changing" in the most reviews.

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[Closer title]

When I moved to NYC, I set out to find my "guy" for everything: barber, coffee, bodega. I want to walk in, hear "the usual?", and tell 'em to keep the change.

There's a decades-old mom-and-pop sandwich shop on my corner. How cute, right? No. Now I must destroy them.

The first time I went, they undercharged me by $5. I gave it back, hoping for a smile. She just grabbed the five without looking up.

The next week:

• "Can I get the #14?"
• "What do you want on it?"
• "Whatever comes on it."
• "I'm not picking for you."

I put my Diet Pepsi down and walked out. We are now enemies. I hope a billionaire-backed slop-bowl chain (preferably owned by Zuck) that doesn't take cash uses eminent domain to take over that place.

Kelly Clarkson, you thought the $15,000 Brooklyn bird was bad? Come to the Upper West Side.

I just needed to rant about that with 32,000 of my friends. /s.

In other news, I had my kid's birthday this weekend (1 and 3 years old). My of our friends who came with kids I met via business or Hampton (obligatory plug, but true).

I didn't want to be a girl dad at first. I want a rough and tumble boy. I was so wrong. Having little girls has been the most fullfilling thing I've ever experienced.

After the party we dressed up in their princess outfits and played with magnet tiles. While playing I got little teary eyed because I thought: this moment is so perfect...I don't know if I'll ever be happier than how I am this second.

Then I realized I said the same thing 3 years ago a few weeks after my eldest was born and she was napping on my chest in her diaper.

Hopefully it keeps going :)

I love you,

Sam

PS: what's the most expensive "productivity" purchase you've made that really just bought you time (a driver, a jet card, a nanny, an assistant)? Was it worth it? Hit reply and tell me. I'll share the best answers.

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