The median startup employee gets about $20,000 from their equity following an exit. And that's before taxes and exercise costs. My latest on whether startup equity is a bad deal:

The median startup employee gets about $20,000 from their equity following an exit. And that's before taxes and exercise costs. My latest on whether startup equity is a bad deal:

The optimal portfolio of the last 54 years had 36% U.S. housing. Run the same optimizer only through 1998 and U.S. housing doesn't appear at all. My latest on the best portfolio over the last 50 years (and why it's an illusion):

The optimal portfolio of the last 54 years had 36% U.S. housing. Run the same optimizer only through 1998 and U.S. housing doesn't appear at all. My latest on the best portfolio over the last 50 years (and why it's an illusion):

Much of the speculative stuff of 2021 ended up failing (NFTs, DeFi, etc.) while much of the speculative stuff of 2025 (AI) seems to be succeeding. My latest on why I was wrong to be bearish on US stocks a year ago:

Much of the speculative stuff of 2021 ended up failing (NFTs, DeFi, etc.) while much of the speculative stuff of 2025 (AI) seems to be succeeding. My latest on why I was wrong to be bearish on US stocks a year ago:

Harvard Business Review tracked the time of 27 CEOs (of large companies) and found that they: -Worked 62.5 hours per week, on average -Worked 79% of weekend days -Worked 70% of vacation days Having time freedom and not using it is the same as not having it.

In 1983, the bottom 20% of workers were more likely to put in long hours than the top 20%. By 2002, the top 20% were twice as likely to work long hours as the bottom 20%. My latest on why "owning your time" is a myth:

Since 1926, the median U.S. stock has underperformed the market by 7.9% over a 10-year period. If you have a lot of money in one stock, you'll likely experience a similar fate. But you don't have to. My latest on the best way to sell a concentrated position:

Nobody talks about the hidden cost of extreme wealth. At $100 million you buy a $30 million house. You have $70 million left earning 7%. That's $5 million a year in income. Try spending $5 million a year. You actually have to work at it. Now scale that to $100 billion. The house doesn't get proportionally better. You can't buy a $30 billion house. The income doesn't get proportionally more enjoyable. You can't spend $5 billion a year. The lifestyle difference between $100 million and $100 billion is virtually nothing. What does change. At a certain level of wealth you lose the ability to have authentic relationships. Everyone wants something from you. Everyone. You can't turn it off and you can't hide from it. You become a mark. Not a person. The Wealth Ladder is the number one book I give every mentee because it maps this out clearly. The lifestyle benefits between Tier 5 and Tier 6 are virtually none. The detriments at Tier 6 are actually more than at Tier 5. We live in a culture that says “more is better.” I can safely attest that it's not true.

A year in your 20s occupies ~5x more of your perceived life than a year in your 60s. Therefore, a dollar you spend in your 20s has about 5x more experiential value than a dollar you spend in your 60s.

The issue with optionality only hit me after I had my first child. I realized that every year I spent single in my early 30s was a year I wouldn't get to spend with my future grandchildren. Optionality has hidden costs.