A Landlord’s Moral Dilemma When Tenants Strike It Rich

With Anthropic’s S-1 now filed with the SEC, over 5,000 employees are about to become extremely wealthy. We’re talking about the median employee making $3 million to $10 million within three years, and likely at least a thousand people making well into eight figures or more. The numbers behind it are astounding. The filing shows $16.3 billion

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Why Aggressive Venture Investing After FIRE Isn’t Reckless

After my posts on being broke again at 49 and feeling silently stressed, some of you let me have it. Irresponsible. Reckless. Top of the market psychology. All fair points. Please keep the respectful criticism coming. I appreciate the pushback because it forced me to look hard at my risk profile and explain it out

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The Silent Stress Of Taking A Family Vacation On A Razor’s Edge 

A couple days before I published Broke Again At 49, my wife said going to Las Vegas over the long weekend would be a lot of fun. I had floated the idea a couple weeks earlier. Unbeknownst to me, she then spent several hours over several days researching hotels, flights, shows, and costs to make it

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Mezzi Review: The Proactive AI Financial Advisor For A Flat Fee

I have more than 40 financial accounts across four people to manage. More accounts means more questions. Can we spend more? Are we missing a tax opportunity? Does an investment still make sense given everything else we own? For years, answering them meant a spreadsheet, a free Saturday, and a lot of analysis that leads

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