Insights and Tips for Financial Success

The other evening, my wife and I went to a school reception held for parents and alumni who donated at least a certain amount in the calendar school year. It was a warm, intimate gathering where I mingled with other parents, shared stories, and listened to the head of school and a couple of trustees […]

Two decades ago, I learned an important lesson: if you can’t beat them, join them. And if you can’t find a job with the monopolies, then you might as well invest in them! Take what happened on September 1, 2025. I got an email from Apple saying my Apple TV+ monthly subscription was going up from

The grindcore culture is back and grindier than ever. At least that’s what Are Kharazian, an economist at fintech startup Ramp, says. (Disclosure: I’m an investor in Ramp through the Innovation Fund.) For those unfamiliar, Ramp is a corporate card company that makes doing expenses easier. But here’s the fascinating part: according to Kharazian, usage of

Since 2022, commercial real estate (CRE) investors have been slogging through a brutal downturn. Mortgage rates spiked as inflation ripped higher, cap rates expanded, and asset values fell across the board. The rally cry became simple: “Survive until 2025.” Now that we’re in the back half of 2025, it seems like the worst is finally over.

Lately, I’ve been thinking more about estate planning. Part of it is just getting older. Part of it is having young children I want to protect no matter what. And part of it is watching the unsettling rise in political violence, which is a stark reminder that life can be cut short unexpectedly. As I

What if one of the best ways to get wealthy is to trick yourself into thinking you’re broke? It sounds counterintuitive, even ridiculous. But after decades of saving, investing, and observing how people behave around money, I’ve realized one thing: abundance often breeds complacency. When you feel flush, you spend more, work less, and get

If you’re thinking about investing in venture capital or any private fund, you need to understand these five key terms: MOIC, TVPI, DPI, Loss Ratio, and IRR. Without them, it’s like walking into a poker game without knowing the rules. And in this game, the stakes—and potential payouts—are massive. I’ve been investing in venture capital

If you want to FIRE, one of my regrets was pulling the ripcord too early at age 34 in 2012. Even though I started writing about FIRE in 2009 with the launch of Financial Samurai—trying to uncover as many blind spots as possible before taking the leap—I still feel like I made a mistake. In

During a bull market, most investors get excited about chasing risk. Despite sky-high valuations, there’s a tendency to double down on even riskier bets in the hopes of making outsized gains. That’s human nature. Nobody wants to miss the boat, and everyone thinks they can outsmart the market. In the process, boring assets like risk-free

The older I get, the more I dislike being a landlord. There’s too much potential for disappointment, misunderstanding, or outright unpleasant moments. When you’re dealing with people and one of your most valuable assets, the margin for frustration is high. If you want to be a successful landlord—and not get run over—you need to set