To outperform the masses, we must take more risk than average. One way to do so is to invest in venture capital. However, venture capital is a form of patient capital, and patient capital requires time. That is the one resource older investors have less and less of. At 50 in mid-2027, I’m entering the […]
The Problem With Investing In Venture Capital When Older Read More »
I get investments wrong all the time. Losing money is part of the process to financial independence. But after I FIRE’d in 2012, the math changed. With no paycheck to bail me out, I could no longer afford big mistakes. This post will help you think about life after FIRE, and share why it’s critical
A FIRE Investor With No Paycheck Cannot Afford to Be Too Wrong Read More »
When you were a kid, did you ever dream of growing up to be someone’s exit liquidity? Probably not. But every time you buy shares in a company IPO, that’s exactly what you become. Whether being an early investor’s exit liquidity is good or bad is hard to say in the short run. In the
Risky Exit Liquidity: Why I’m Passing On The SpaceX IPO Read More »
In real estate, money is made on the purchase, not the sale. That means every dollar you negotiate off the asking price is a dollar straight to your net worth. So you need every tool at your disposal: savvy representation, patience, a compelling offer, and yes, even publicly available data that happens to be wrong
How to Use Bad Housing Data to Negotiate a Lower Price Read More »
I recently received a great comment on my post, Why All Rich People I Know Still Have Life Insurance. It was the last line that stood out. Here’s what Marc had to say. I had life insurance ($1M) through my employer back when I worked full time, but since I cut back to ~10 hours per
Retire Before Your Kids Leave Home, Not After Read More »
Living in San Francisco since 2001 is a surreal experience. I arrived a year after the dotcom bubble burst, and the city felt desolate, especially downtown where Credit Suisse was headquartered at 201 Howard Street. I was coming from New York City, which felt vibrant at all hours, including at 5:15 am when I’d walk
From Doom Loop to Boom Loop: A San Francisco Story Read More »
I vividly remember sophomore year of college. It was 10:30pm and I was leaving my girlfriend’s apartment by car. Instead of coming to a complete stop at the stop sign, I slowly rolled on through and took a right. There was nobody on the streets, so I took a chance. That chance cost me $60.
How To Overcome Financial Despair For Good Read More »
Here’s something I’ve noticed: the loudest voices arguing against life insurance after financial independence almost always come from people who aren’t financially independent yet and don’t have kids. They’re still grinding toward FIRE, optimizing every dollar, cutting costs to close the gap. Makes sense for them. But once you actually get there, the calculus changes.
Why Every Rich Person I Know Still Has Life Insurance Read More »
Do you know who will most likely survive a zombie apocalypse? Green Berets and Navy SEALs who had to suffer to earn their place. If you have run six miles a day for years, jogging thirty minutes to evade the horde because there are no Ubers is nothing. If you have carried 125-pound sandbags up
Suffer Now, Thrive Later: Relish Working Brutal Hours Early in Life Read More »
At a poker game recently, I heard one of the saddest things I’ve encountered in a while: “$10 million is not enough to retire early.” Mind you, we were all sitting in San Francisco, an expensive city, but also one of the cheapest international cities in the world. So I get it, context matters. But
Of Course $10 Million Is Enough To Retire Early, Don’t Be Crazy Read More »
