Of Dollars And Data
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Is Startup Equity a Bad Deal?
Imagine joining a startup as employee number 10. Your salary is a bit below what the market pays for your role, but, in exchange, you get equity. How much? 0.25% of the company to be exact. You do the math in your head—if the company sells for $100M in a few years, you'll make $250,000. Not bad…
What Was the Best Portfolio Over the Last 50 Years?
A few months ago, I analyzed U.S. stock returns over the last century . Today, I'm going to determine the best portfolio over the last 50 years among the following asset classes: U.S. Stocks International Stocks Real Estate Investment Trusts (REITs) U.S. Corporate Bonds 10-Year Treasury Notes…
Living Poor to Die Rich
I recently joined a professional organization to discuss various topics in wealth management. On our first Zoom call there was a debate around the use of levered long/short strategies. For the uninitiated, a levered long/short strategy is a way of taking market risk (like buying an index fund)…
Which Graduate Degrees Are the Best Investment? (Why I Skipped My MBA)
When I was 27 years old I was at a crossroads. I was five years into my career, yet I was stagnating. Though I was making six figures, which was great for my 20s, I knew I couldn't make much more at my job. Without an advanced degree, my future compensation would be an endless chain of 3% annual…
Why I Was Wrong to Be Bearish on U.S. Stocks
A year ago I wrote the blog post Why I'm Bearish on U.S. Stocks (for the Second Time Since 2017) . Since then U.S. stocks are up 16% (total return) and my bearish prediction turned out to be misguided. So where did I go wrong? And how can you prevent yourself from making the same kind of error in…
The Myth of Owning Your Time
You've probably heard it all before. Be your own boss. Control your schedule. Own your time. As attractive as it sounds, it's a lie. Many people believe that working for yourself means unlimited flexibility. You can work where you want, when you want, and with whom you want for the rest of your…
The Best Way to Sell a Concentrated Position
Imagine being the typical SpaceX employee over the last few months. Your shares IPO at $135 and within a few days they peak at $225/share (up 67%) before they begin to decline. As of this morning they sit at around $139, or about 3% above the IPO price. Given this, what percentage of your shares…
Why $100 in Your 20s is Worth $500 in Your 60s
What if I told you that $100 at 25 is worth $500 at 65, even after we adjust for inflation? Well...it is. There's an unspoken belief in personal finance that a dollar is always worth a dollar (putting inflation aside). We assume that spending $100 today would bring the same amount of joy as…
The Problem with Optionality
I’ve seen a lot of discussions this year around maximizing freedom and optionality. For example, consider this tweet : If you ever get up $1M in cash Buy a new modern apartment in the UAE for like $550k (you have zero property tax). Once you own it, it’s actually yours, and the only thing you pay…
Money Talks: The Price of Status
A year ago, I published my second book The Wealth Ladder . It's sold over 100,000 copies worldwide and hit the New York Times bestseller list in its third week of publication. At the time, I was thrilled that my work was finally getting some mainstream media attention. After nine years of writing…
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