Wealth

You earned it
on the bag.
Now grow it.

Caddies earn real money young — often before their peers have their first job. What you do with it from here matters more than most people realize. Start early. Live below your means. Invest the surplus. Active or passive — that's your strategy to choose.

This is not investment advice. We're sharing information and philosophy so you can educate yourself and make your own decision.

"As a young boy caddying in New York, Ray invested his wages into stocks. That decision launched his career as an investor."
Ray Dalio · Bridgewater Associates
"Mario Gabelli used the money he earned caddying at Wykagyl Country Club to start investing — an education that laid the foundation for one of Wall Street's great careers."
Mario Gabelli · Gabelli Funds

Three things that matter more than which strategy you pick.

01
Start early.
Time in the market matters more than timing the market. A dollar invested at 18 compounds very differently than a dollar invested at 35. The caddie yard gives you a head start most people never get. Use it.
02
Live below your means.
The gap between what you earn and what you spend is the raw material of wealth. Every dollar you don't spend is a dollar that can compound. This isn't deprivation — it's leverage. The earlier you build this habit, the more powerful it becomes.
03
Invest the surplus.
The money left after you've lived your life is the money that builds your future. Whether you index or actively manage is secondary to the discipline of actually investing it — consistently, patiently, and without panic.

Buffett's advice has two halves. "Consistently buy an S&P 500 low-cost index fund." But also: "Diversification is protection against ignorance. It makes little sense if you know what you are doing." The index is for the investor who won't do the work. Concentration is for the one who will. If active investing clicks for you immediately — if you'd do it even without the money — this is your path. If you're not sure, you already have your answer.

Warren Buffett on index funds — Humble Dollar →
Active Management

Beat the market.
If you're willing
to do the work.

Active management self-selects. If you're a know-something investor, you can't help it — you're going to dig in, build a point of view, and back it with conviction. That's how Dalio, Munger, and Lynch built their records. Concentrated. Patient. Willing to be wrong in the short term.

If that's you, study these luminaries.

Warren Buffett
The Warren Buffett Way
Robert Hagstrom
How Buffett's approach was shaped by Ben Graham, Phil Fisher, and Charlie Munger.
The Warren Buffett Portfolio
Robert Hagstrom
When to buy, how much to buy, and when to sell. The focus investment strategy.
Warren Buffett's Ground Rules
Jeremy Miller
Buffett's earliest days as an investor — more relatable, and more activist than most realize.
The Deals of Warren Buffett: The First $100M
Glen Arnold
Deal-by-deal: how he went from $100K to $100M over several decades.
The Outsiders
William Thorndike
The best book on capital allocation — the most important skill in business.
The Snowball
Alice Schroeder
The most comprehensive Buffett biography — the life and events that shaped his career.
Charlie Munger
Poor Charlie's Almanack
The core compilation of his multidisciplinary thinking, public talks, and biographical info.
Charlie Munger: The Complete Investor
Tren Griffin
Munger's specific business strategies and mental models for ordinary investors.
Damn Right!
Janet Lowe
An authorized biography of Munger's life and career at Berkshire Hathaway.
Tao of Charlie Munger
Munger's wit and wisdom distilled into actionable principles.
Joel Greenblatt
You Can Be a Stock Market Genius
Finding profits in special situations: spin-offs, restructurings, and bankruptcies.
The Little Book That Beats the Market
The "magic formula" for finding good stocks at bargain prices.
The Big Secret for the Small Investor
How individual investors can use value principles to beat index funds.
Phil Fisher
Common Stocks and Uncommon Profits
The qualitative approach to finding great businesses before they're obvious.
Peter Lynch
One Up on Wall Street
How everyday investors find opportunities professionals miss. Strategy over stock tips.

Also on Kai's reading list: 6 best books on value investing

Passive / Indexing

Beat most investors
by doing
almost nothing.

Index investing means buying the whole market and getting out of your own way. Low costs, broad diversification, and patience. Most active investors — including professionals — underperform the index over time. If you don't feel the pull to dig into individual companies, this is the right answer.

These three books make the case better than most.

The Little Book of Common Sense Investing
John C. Bogle
The founder of Vanguard makes the case for indexing. Short, clear, irrefutable.
A Random Walk Down Wall Street
Burton Malkiel
Why stock prices are unpredictable — and what that means for your strategy.
The Psychology of Money
Morgan Housel
The behavioral side of wealth — why your mindset matters as much as your strategy.

Further reading: Warren Buffett on index funds

Coming Soon

How I made two million dollars
emulating Charlie Munger.

Kai Sato's next book documents his own active investing journey — the philosophy, the mistakes, the concentrated bets, and the long holds that added up to over two million dollars in the stock market. Not a get-rich-quick story. A story about discipline, patience, and learning from the best.

Book · Coming 2027
Accelerated Compounding
How I Made Two Million Dollars in the Stock Market by Emulating Charlie Munger — by Kai Sato
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