Investing & Taxes

One of the first things they teach you in the unofficial Personal Finance Classics canon of required reading is that every time things look like they’re going awry, people will insist, “This time, it’s different. This time, we’re not coming back from it!” Every author cautions against falling prey to this mix of seductive pessimism […]

In 2021, Vanguard—the second-largest investment firm in the world, trailing only behind BlackRock—saw inflows of roughly $1B per day. Overall, they’ve got $7.5 trillion under management. That’s a fancy way of saying that a shit ton of people stick their money in Vanguard.  When we see major firms like this, it’s easy to forget that […]

Hint: You may not need that Backdoor Roth IRA after all. Blasphemous, I know—and while I’m sure this article will apply to a pretty niche segment of my audience, I had an important realization the other day that I feel I must share: Most full-timers with side hustles (hello, millennials) aren’t taking advantage of the […]

Let’s all transport ourselves back in time for a moment to March 2020.  In retrospect, you may not feel that much of an emotional reaction thinking back because of what we now know happened afterward: The stock market, housing market, and job market recovered relatively quickly and surpassed their former highs.  But join me for […]