William Leith13 June 2020

Why Some People Become Ridiculously Rich - William Leith - #183

0Frameworks

14Insights

Insights & moments

The myth-busts, hot takes, explainers, and tools worth keeping.

Hot Take· 2

Hot Take38:30

It's the Getting Rich, Not Being Rich, That the Wealthy Are Actually Chasing

Leith argues, via a Kingsley Amis analogy about drinking, that the pathological drive in ultra-wealthy people isn't the money itself but the process of accumulating it. Once the 'hockey stick' curve flattens, they don't stop — they keep chasing the climb because that's where the pleasure was, not in the possessions it buys.

Kingsley Amis: 'it's not about being drunk, it's about getting drunk' — the process, not the state
Once you own an infinity pool, a Ferrari, a private island, the marginal purchases have diminishing returns
The richest people aren't focused on the money as an outcome — they're focused on maintaining the journey/curve
This explains why people keep pushing well past the point of any rational need

“It's not about being drunk, it's about getting drunk.”
William Leith (quoting Kingsley Amis) · 38:30

“You can only spend it on certain things... you run out of things to buy pretty quickly.”
William Leith · 39:30

#wealth psychology#hedonic treadmill#motivation

Hot Take56:00

"History Doesn't Crawl, It Leaps"

Leith shares a favorite quote capturing how major change — in markets, careers, and history itself — doesn't happen gradually but arrives in sudden leaps after long periods where nothing visible seems to be happening, mirroring evolutionary change and the 'nothing happens, then everything happens' pattern he found across every rich person he studied.

Quote: 'history doesn't crawl, it leaps' — change arrives suddenly, not incrementally
Compared to evolution: species don't gradually shift, they leap into something new that may or may not survive
Ties back to Taleb's core lesson: expect the unexpected, because nobody else is looking for it
Applies to money-making too — long flat periods followed by a fast payoff once the pieces click

“History doesn't crawl, it leaps.”
William Leith · 56:30

“If you try to expect the unexpected, you'll do a lot better, because nobody else is looking.”
William Leith · 57:00

#nassim taleb#history#change

Explainer· 4

Explainer28:00

How Ingvar Kamprad's Brain Priced an Entire Supply Chain Instantly

Leith describes meeting IKEA founder Ingvar Kamprad's design team and learning that Kamprad could mentally run the full cost chain of a product the instant he saw it — sourcing, materials, shipping, currency conversion — and use that to make immediate go/no-go calls, a mental skill he found mirrored in the Russian billionaire he later interviewed.

Shown a pine table, Kamprad's mind would instantly compute sourcing costs, trucking, currency exchange and per-unit price at volume
He would decide 'do it' or 'this one's not gonna fly' based on that instant mental model
The Russian rag-trade billionaire had the identical skill applied to garment manufacturing across Chinese factories

“His mind would be buzzing with all these things and then he would just say to the guy: okay, do it. No, this one's not…”
William Leith · 29:00

#ikea#business acumen#supply chain

Explainer53:30

Why Betting Against the Market Pays More Than Betting On It

Leith explains a Nassim Taleb-influenced insight about market asymmetry: betting on things improving is cheap and crowded because most people want that bet, so returns are small and steady until a rare blow-up. Betting on things getting worse is lonely and unpopular, so it's underpriced — you lose money slowly most of the time but the payout when you're right is disproportionately large.

Long bets (things get better) are crowded and cheap, giving small, steady returns until a rare catastrophic loss
Short bets (things get worse) are unpopular because losing money every day while waiting is psychologically hard, so few compete for them
Because so few people take the losing side, the eventual payout when a downturn hits is bigger than the odds suggest
Leith compares this to job security: 'safety is overpriced' because so many people want a safe job they're willing to be underpaid for it

“It's a lonely place to be losing money every day in the hope that everything crashes — so not many people do it. It turns…”
William Leith · 54:30

“Safety's overpriced. A lot of people want a job for life, so they're prepared to be underpaid for it.”
William Leith · 55:00

#investing#nassim taleb#risk#asymmetry

Explainer49:30

How Growing Up in Lebanon's War Shaped Nassim Taleb's Black Swan Thinking

Leith explains where Nassim Taleb's worldview came from: as a young man in Lebanon, he watched a war everyone assumed would be 'over by Christmas' drag on for years, teaching him that history isn't driven by predictable trends but by rare, unexpected, high-impact events — which he later termed Black Swans.

Taleb was around 20 when the Lebanese civil war broke out; people insisted it would be short, but it dragged on for years
This taught him that history is dominated by unexpected 'weird' events rather than steady predictable change
He applied the same lens to markets and, alongside people like Michael Burry, saw the 2008 housing crash coming before most
Taleb argues the current pandemic wasn't a true Black Swan because some people did predict it — but society at large wasn't prepared regardless

“Nobody predicted that this would be such a long-term, immensely destructive conflict... he began to think: weird things happen — things people don't want to…”
William Leith · 49:30

#nassim taleb#black swan#lebanon#history

Explainer60:30

McGilchrist's Left-Brain/Right-Brain Theory of Why We Build Tools to Make Tools

Leith summarizes Iain McGilchrist's book 'The Master and His Emissary': one hemisphere of the brain evolved to observe nature, the other to turn what it sees into tools. As civilization built more tools, the tool-making side started building tools out of other tools (cars, computers, financial products), a recursive process Leith connects to complex financial instruments like mortgage-backed bonds.

One side of the brain observes nature; the other side asks 'how can I make a tool out of that'
As cities replaced nature with tools, the tool-making brain started making tools out of tools instead of raw materials
Leith links this directly to financial engineering: mortgages packaged into bonds packaged into more complex products
The safety of modern life ('fewer people falling into the ravine') has let the tool-making side run further from its original grounding

“The left side is saying: yeah, how could I make tools out of those tools? Oh, I know — I could sell them in advance…”
William Leith · 61:30

#iain mcgilchrist#neuroscience#finance#books

Story· 5

Story04:30

The Author's Own Pathological Relationship With Money

William Leith reveals that despite studying how the rich think, he personally struggled with money the way an addict struggles with alcohol. Any money he made would 'get into him' and change his identity, leading him to spend it all and then borrow more. He compares the compulsion directly to his history with alcohol and cocaine, where one drink reliably led to a blackout.

Leith is a recovered alcoholic, sober for over seven years
He describes money entering his identity: 'you'd become this person who had some money and then it would all be gone'
He likens the urge to a bully-versus-compromiser dynamic in the head, e.g. going to two parties instead of choosing one
Substances (alcohol, cocaine) had the same escalating, out-of-control quality for him as money did

“Even when I made a load of it, it would somehow get into me and change me — I'd become this person who had some…”
William Leith · 04:30

“It's like part of you is a bully saying 'go on, have this, have this' and another part of you is like 'well, I guess…”
William Leith · 06:30

#money psychology#addiction#self-help

Story07:30

Interviewing Jordan Belfort: Why the Wolf of Wall Street Committed Fraud He Didn't Need

Leith explains that his conversation with Jordan Belfort (the real-life Wolf of Wall Street) was the turning point for the book. Belfort was a gifted salesman who built a fortune legitimately through motivational persuasion, then crossed into an illegal stock-manipulation scheme with a partner — a decision Leith finds baffling given Belfort already had the skill to make money honestly.

Belfort's real gift was motivating a room of brokers through pure salesmanship
He started with legitimate (if aggressive) stock promotion, then a partner showed him how to illegally pay people to buy and dump stocks
He was caught and jailed, and at the time of the interview was rebuilding his life by teaching others how to make money
Leith was struck by the contradiction: someone who could make $100M legitimately risking it all for fraud

“How do you make a hundred million? But then why, when you've made a hundred million, do you commit a fraud that might well land…”
William Leith · 08:00

#jordan belfort#wolf of wall street#fraud#sales

Story17:00

Warren Buffett Ran 11 Businesses at Age 16

Leith spent a year studying Warren Buffett and pieced together a picture of him at 16 running roughly eleven small businesses simultaneously — a car wash, a golf-ball resale operation, and a stamp-collection arbitrage scheme — each one teaching him a granular, ground-level view of how a business actually works.

Buffett hired kids to run a car wash and cut it once it stopped being profitable enough
He paid people to retrieve lost golf balls from a Nebraska lake and resold them to a second-hand golf ball buyer in Illinois
He noticed a complete stamp collection was worth ~$200 while one missing ten stamps was worth $5, and built up incomplete collections to sell
He made more money than his teachers and parents at 16, and the real payoff was learning how businesses work from the ground up

“He was constantly running these businesses, made more money than his teachers, his parents — extraordinary.”
William Leith · 18:30

#warren buffett#entrepreneurship#childhood

Story25:30

A Day Inside a Lonely Russian Billionaire's Mansion

Leith recounts visiting the English country estate of a Russian half-billionaire who made his fortune in the rag trade, once designed by Christopher Wren and Nicholas Hawksmoor. Despite the extraordinary luxury — including his own church with no congregation — the man lived essentially alone with just his butler, who ate separately in the servants' quarters.

The house was originally designed by Christopher Wren and completed by Nicholas Hawksmoor around 1700
The Russian owner had a computer-like grasp of his clothing business's entire supply chain, similar to IKEA's Ingvar Kamprad
He lived alone on the estate with only a butler for company, who cooked but ate separately
The estate included a private church with no congregation

“You've got a church, you haven't got a congregation — you in there.”
William Leith · 33:00

#wealth#luxury#loneliness#case study

Story34:00

Felix Dennis: The Statue of Icarus at the End of His Own Driveway

Publishing billionaire Felix Dennis built an avenue of statues on his Warwickshire estate ending in a statue of Icarus plunging to his death — a warning he'd placed for himself. Leith recounts how Dennis said making roughly £450 million had driven him to become a crack addict, triggered a four-year existential crisis, and arguably contributed to the lung cancer that killed him.

Dennis commissioned full-size statues leading to a converted barn where he wrote poetry — ending in an Icarus statue as a self-warning
He told Leith the money-making process turned him into someone he personally disliked: hard-driving, obsessive, permanently focused on advantage
He said he should have stopped at £50 million; the remaining £400 million 'had done him in'
He became a crack addict, had a four-year existential crisis, and died of lung cancer likely linked to years of crack smoking

“He'd made like four hundred and fifty million quid or whatever, but he should have stopped at fifty. That last four hundred — what was…”
William Leith · 37:00

#felix dennis#wealth psychology#addiction#cautionary tale

Tool· 1

Tool70:00

The Trick — Leith's Book on Money, and Its Audiobook Narrator

Leith plugs his book 'The Trick,' available on Amazon and in an audiobook version he's especially proud of, narrated by a voice actor whose delivery he compares to comedian Jack Dee — a detail he found so fitting he emailed the narrator to thank him personally.

The book is called 'The Trick,' available on Amazon, in bookstores, and as an audiobook
Leith did not narrate it himself; a professional narrator did, with a delivery style Leith compares to comedian Jack Dee
Leith emailed the narrator directly to thank him for the performance

“It's a guy called Rich People and his voice is a bit like Jack Dee — it sounds like my book read by Jack Dee.”
William Leith · 70:00

#book recommendation#the trick#william leith

Takeaway· 2

Takeaway66:30

"If I Write Something I Haven't Wasted My Time — If I Buy Something I Might Be Sick of It"

Leith closes with a lesson from Felix Dennis, who felt money had damaged his life: creating something (writing, making) produces lasting satisfaction, while buying things produces only fleeting pleasure that fades quickly, no matter how expensive the purchase.

Dennis felt he'd 'ruined his life' with money despite his fortune
His rule: making/writing something is never wasted time; buying something often doesn't deliver lasting value
Leith connects this to the broader theme that it's the process of becoming, not the state of having, that produces satisfaction
Even extreme luxury (a $1,000 bottle of wine, a rotating garage for a Rolls Royce) has fast-diminishing returns

“If I write something I haven't wasted my time, but if I buy something I might be sick of it — spending money isn't the…”
William Leith · 67:00

#felix dennis#happiness#wealth psychology

Takeaway63:00

Money Buys Comfort and Time — Not Happiness Past a Point

Leith gives his final, personal answer on what years of interviewing the ultra-wealthy taught him about money: it removes fear and buys you time, but past a comfortable baseline it stops making you happier and can actively damage relationships if you become obsessed with it.

Leith says he's never been 'fabulously rich' and doesn't expect to be — and is at peace with that
Money's real value is removing fear (e.g. of people knocking on your door) and buying freedom of time
Beyond comfort, more money doesn't reliably increase happiness — a nicer car or fancier restaurant wine wears off within a week
Obsessing over money can cost you the relationships and time-use that actually generate happiness

“What you want is to be rich in time — and also your relationship with other people. Being obsessed with money can take those things…”
William Leith · 64:00

#money and happiness#wealth psychology#life advice