If you own rental properties, this guest post may resonate with you. It’s about what to do with a property once it has served its purpose: keep renting it out, sell and pay capital gains taxes, sell via a 1031 exchange to defer taxes, move back in to avoid taxes, or—most controversially—simply leave it empty. For […]
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The other evening, 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 talk about the […]
The post The Difficulty Of Donating Money When You’re Unemployed Or FIRE appeared first on Financial Samurai.
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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 […]
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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 […]
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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. […]
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How The Irrevocable Life Insurance Trust Saves Families From the Estate Tax Hammer
4:31 AMAs I inch closer to death, I find myself thinking more about estate tax planning and the potentially massive tax bill my family might face if we're extremely lucky. To get ahead of it, I dug into how an irrevocable life insurance trust (ILIT) could help families save big on the so-called death tax. Picture […]
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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 […]
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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 […]
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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 […]
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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 post Treasury Bonds Can Appreciate In Value Too – Don’t Ignore Them appeared first on Financial Samurai.
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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 […]
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I haven’t checked my net worth for four months until recently. That wasn’t on purpose, because normally, since 2012, I check at least three times a week using Empower’s free app. The only reason I stopped was because I could no longer log in. One day, I was suddenly locked out of the app. I […]
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