Investing & Taxes

Correction: An earlier version of this piece incorrectly stated you’d pay short-term capital gains taxes on the spread between your discounted option price and the fair market value of the stock. It has been corrected below to clarify you’d pay ordinary income tax, not short-term capital gains taxes (as you have no capital gains, if […]

Take a look at this chart. Can you guess what it’s measuring? Is it the S&P 500’s performance over time?  Close! It represents searches for the term “S&P 500” over time.  Why am I looking at this? Well, mostly because I don’t have other empirical ways to get a pulse check on public awareness of […]

When I originally published this post in February 2021, my thesis was pretty simple: Comparing your financial situation and decisions to the gals you wine down with on Bachelor Monday probably won’t net highly favorable results, because you’re selecting your “financial frame of reference” based on unrelated qualifications. As I revisit the idea in 2025, […]

Inflation is at its highest level in nearly 40 years. Grocery budgets are straining at the seams. When Russia invaded Ukraine, the West answered with “I think the fuck not” plus oil sanctions that led to gas price spikes. The Fed is gluing down the button that raises rates and playing an unprofitable game of […]