Life is hard if you want to outperform average. To reach a USTA 5.0 level in tennis takes an endless amount of practice. To get promoted to Managing Director in banking, you first have to survive a decade of 70+ hour weeks just for a shot. And if you want to be your own boss and build […]
The Incredible Satisfaction of Never Giving Up: A Lesson In Grit Read More »
Part of the reason I’ve been writing about distribution and the importance of eventually betting on yourself was to gear myself up for Y Combinator Demo Day. For those unfamiliar, YC is the largest and arguably the best startup accelerator in the world. And it happens to be based in my backyard in San Francisco.
Y Combinator Demo Day: The Quest To Invest In The Best Startups Read More »
After graduating from Berkeley’s MBA program in 2006, I wanted to start Financial Samurai. But even after taking entrepreneurship, marketing, and finance courses, everything I needed to launch a business, I didn’t. My excuse was that my firm, Credit Suisse, had paid for 80% of my MBA education, and I felt obligated to repay them
Stop Waiting For Permission To Build A Fortune Read More »
Back in 2012, the year I left banking and three years after I started Financial Samurai, I had a choice: run a lifestyle business or build a venture-backed company. I chose the lifestyle business. After 13 years in equities I was burned out and just wanted to be free to enjoy the FIRE lifestyle. Writing
Distribution May Be The Last Moat: 17 Years Of Financial Samurai Read More »
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 »
