Finance Xpress

In anticipation of investing in some YC Demo Day startups, I transferred $50,000 from my Fidelity brokerage account to my Citibank checking account. This was right after I'd already wired $56,100 to meet a capital call for a new traditional venture capital fund I committed to. In a previous post, I wrote about the difficulty of committing […]

The post Summer YOLO Fund: Permission To Spend More and Save Less appeared first on Financial Samurai.

This past Father's Day, June 21, 2026, I had a choice to make. I could play pickleball from 9am to 12noon at an indoor club called Flyte, a 30-minute drive north. Or I could take my kids 30 minutes south to the Bay Club Redwood Shores for swimming and tennis and pickleball lessons. For over […]

The post How To Overcome The Guilt Of Not Taking Care Of Your Own Kids appeared first on Financial Samurai.

Most of us take the safe road. We go to college, get a job, and spend the next 30 years hoping our employer doesn't one day decide we're suddenly redundant. I know this path well because I walked it for 13 years before I finally worked up the nerve to do my own thing in […]

The post The Entrepeneur’s Journey: From Mexico To A Symantec Exit appeared first on Financial Samurai.

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 post The Incredible Satisfaction of Never Giving Up: A Lesson In Grit appeared first on Financial Samurai.

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. […]

The post Y Combinator Demo Day: The Quest To Invest In The Best Startups appeared first on Financial Samurai.

After graduating from Berkeley's MBA program part-time 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 […]

The post Stop Waiting For Permission To Build A Fortune appeared first on Financial Samurai.

Back in 2012, the year I left banking, I had a choice: build 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 and tinkering 15 to 20 hours a week […]

The post Distribution May Be The Last Moat: 17 Years Of Financial Samurai appeared first on Financial Samurai.

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 post The Problem With Investing In Venture Capital When Older appeared first on Financial Samurai.

I get investments wrong all the time. Losing money is part of the game. 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 to stay measured […]

The post A FIRE Investor With No Paycheck Cannot Afford to Be Too Wrong appeared first on Financial Samurai.

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 […]

The post Risky Exit Liquidity: Why I’m Passing On The SpaceX IPO appeared first on Financial Samurai.

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. […]

The post How to Use Bad Housing Data to Negotiate a Lower Price appeared first on Financial Samurai.

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 […]

The post Retire Before Your Kids Leave Home, Not After appeared first on Financial Samurai.

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 […]

The post From Doom Loop to Boom Loop: A San Francisco Story appeared first on Financial Samurai.