Things I’ve been wrong about.

I thought: I assumed the GSE court cases would wrap in three years. Five tops.

It turned out: I'm on year fourteen. Oral argument was two days ago. Opinion lands somewhere between this summer and early next year.

Patience is an investment. It compounds. It also gets expensive if you forget to live in the meantime.

I thought: I thought the skill was having more opinions.

It turned out: The skill is having fewer, and holding them across domains.

I thought: I thought the hedge fund world was a meritocracy that would reward someone who read Graham cover to cover and modeled every position in Excel.

It turned out: It mostly rewards people who can already raise money. I could read. I couldn't raise.

Capital formation is its own skill. Nobody tells you that until after you've tried.

I thought: I thought I could reform the fund industry from inside by running a tiny, honest one.

It turned out: Tiny and honest does not scale. The industry kept doing what it was doing. My fund closed.

I thought: I figured the Fannie/Freddie story would be obvious to the public pretty fast once the litigation started making news.

It turned out: The public has a very high tolerance for expropriation if the numbers have a lot of zeros.

I thought: I was right that crypto had no intrinsic value. I thought that would be enough.

It turned out: The market stayed irrational longer than my patience. Being right and being early look identical from the outside. They are not the same trade.

I thought: I assumed the enterprise Salesforce market would close ranks against solo builders.

It turned out: It's moving the other way. Small teams with sharp products keep winning shelf space. I was wrong about the direction.

When I'm wrong about a trend, I'm almost always wrong about the speed of the trend, not the direction. This was the rare one where I was wrong about the direction.

I thought: I thought 'done with government work' meant I was done with government work.

It turned out: I wrote another two books about the government conservatorship. I'm pretty sure I'm not done.

I thought: I thought writing eight books about one trade was thorough.

It turned out: It's also how you discover you are, in fact, obsessed.

I thought: I thought I could freelance Salesforce indefinitely as a solo contractor.

It turned out: Solo contracting is a job with extra paperwork. I stopped pretending it was a business and started building one with other people in it.

I thought: I thought building one excellent Salesforce product would be enough of a business.

It turned out: Turns out one product with one customer is a consulting engagement. The business is the portfolio. Eight products, now.

I thought: I assumed I would ship a book a year on top of everything else.

It turned out: I have not shipped a book in a while. I keep telling people I'm going to. They keep nodding politely.

I thought: I thought I was moving to Miami Beach for the weather.

It turned out: I moved for the family. The weather is a bonus. I'd been telling the wrong story about my own life.

I thought: I told Bo the new place would take thirty days to fully set up.

It turned out: We signed the lease in April and I'm still telling her thirty more days. I do this with codebases too.

Overbudget the timeline. Then overbudget it again. Then hope.

I thought: I thought the site would stop growing once it hit a thousand pages.

It turned out: It's past two thousand. The build machine keeps running out of memory. I keep adding pages. Neither of us has learned.

I thought: I keep thinking I've already picked up the lesson.

It turned out: I mostly just pick up the shape of it. The specifics have to teach me again, in a new costume, every few years.