What Private Equity Taught Me About My Own Money
The four questions private equity investors ask before a dollar moves: return, downside, leverage, and exit.
- Decision-Making
Archive
Every letter, newest first. Read the Tuesday/Friday pairs together when you can -- the Foundation post earns the attention; the Philosophy post says what to do with it.
The Cliff Is Not Where You Think
The leap gives you time. It does not tell you what the time is for.
- Decision-Making
When to Pick Stocks (And When to Leave It Alone)
Indexing is right for most money. The edge belongs only to the slice you are willing to do real work for.
- Money Fundamentals
Community Is the Asset Nobody Puts on the Balance Sheet
The job was handing you people. When you leave, the social infrastructure disappears with the paycheck.
- Unconventional Paths
The Day Your Portfolio Makes More Than You Do
The moment your invested capital starts doing more work than your paycheck changes the job forever.
- Money Fundamentals
The Harder Freedom
The visible version of breaking free shows up on a statement. The other version is the work the money cannot do for you.
- Values & Identity
Zero Is a Legal Number
Low-income years are assets, and most people waste them.
- Money Fundamentals
What Are You Optimizing For?
You can optimize every account perfectly and still be optimizing toward nothing. Name the destination before you spend another year tuning the engine.
- Decision-Making
Frugality Got Me Free. Then It Became the Cage.
You can afford it. So why do you still feel guilty?
- Values & Identity
Buy Back Your Time
The real question is not what the task costs. It is what the hour could become.
- Time & Energy Economics
Which Account Should You Fund First?
The order you fund your accounts captures free money and tax advantages that compound for decades -- including the HSA trick almost nobody uses correctly.
- Money Fundamentals
Traveling Lite
What a cramped trunk and a heavy backpack taught me about money: the more you carry, the fewer moves you have. Conscious spending as traveling light.
- Values & Identity
A Budget Is a Confession
A budget isn't a constraint -- it's a confession. Every allocation states what you actually value. Five categories that mean something, and when to stop budgeting.
- Money Fundamentals
Which Is Worth More?
Everyone says time is more valuable, then organizes their whole life around the money. The 'I'm so busy' tell, the time audit, and what 'rich' actually means.
- Decision-Making
The Two Currencies You Spend Every Day
You track your money obsessively and your time not at all -- even though one is the currency you can never earn back. The exchange rate between them, and why it moves your whole life.
- Time & Energy Economics
Why Breaking Free Exists
Make the numbers honest enough to make better life decisions.
- Values & Identity
The Day I Stopped Trading Time for a Salary
The spreadsheet said stay. The life math said something else.
- Unconventional Paths