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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 Entrepreneur’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 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 […] The post Stop Waiting For Permission To Build A Fortune appeared first on Financial Samurai.
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 […] 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 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 […] 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.
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. […] The post How To Overcome Financial Despair For Good appeared first on Financial Samurai.
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. […] The post Why Every Rich Person I Know Still Has Life Insurance appeared first on Financial Samurai.
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 […] The post Suffer Now, Thrive Later: Relish Working Brutal Hours Early in Life appeared first on Financial Samurai.
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 […] The post Of Course $10 Million Is Enough To Retire Early, Don’t Be Crazy appeared first on Financial Samurai.
I’ve been playing poker for over 25 years, and I still love the game. Every time I sit down at a table, it feels like a time warp. Three hours can pass in the blink of an eye. The cards, the psychology, the rhythm of betting, and the social interaction all combine into something that’s […] The post A Net Worth and Income Guide to Playing the Right Poker Stakes appeared first on Financial Samurai.
The main reason I can't convince anyone in real life to FIRE is the desire for more. The moment you hit a $1 million net worth, you start dreaming of $5 million. Get to $5 million and suddenly $10 million sounds reasonable. Hit $10 million and, well, why not shoot for $25 million and higher? […] The post The Multi-Million Dollar Home That Ate Your FIRE Number appeared first on Financial Samurai.
The problem with writing about FIRE since 2009 is that I've become completely sold on the lifestyle. I know how good freedom feels, so I have a natural tendency to want everyone to achieve it too. I'm also aware I can come across as annoying when I talk about FIRE, so I try to throttle […] The post Failing to Convince Anyone in Real Life to FIRE Despite Big Gains appeared first on Financial Samurai.
One of the issues we frugal people despise is going through buyer’s remorse. We don't want to feel stupid or ripped off, so we tend to buy fewer things and experiences. Minimalism and early retirement go hand in hand. We're always looking for a deal, partly to minimize disappointment. And if we can get something […] The post Time Fixes Most Financial Mistakes Because You Grow Richer appeared first on Financial Samurai.
As I approach 50 in mid-2027, I've been thinking a lot more about responsibility, legacy, and mortality. What I've realized is that responsible adulting is hard. One misstep and you or your loved ones could be screwed for life. Ultimately, life is a series of financial quests for survival before we die. If we don't […] The post Life Is Simply One Financial Quest After Another appeared first on Financial Samurai.
I love startups and entrepreneurship. My obsession started when I was reselling Nerds candy in Taipei, purchased from the U.S. commissary store. To recognize and exploit a pricing arbitrage as a nine-year-old felt like winning the lottery every time a new batch arrived. In 1998, a year before graduating from William & Mary, I was […] The post The Startup Grind Will Make You An AI Maximalist appeared first on Financial Samurai.
Here is a question worth sitting with: which is actually harder to achieve, a top 1% income or a top 1% net worth? Most people assume income. The number sounds impossibly high, the competition sounds brutal, and the lifestyle of someone earning that kind of money seems reserved for a different species entirely. But after […] The post Top 1% Income vs. Top 1% Net Worth: Which Is Harder to Achieve? appeared first on Financial Samurai.
The decade-long advice to “learn to code” is losing its edge. With tools like Claude Code handling the heavy lifting, a basic three-month online course may be all anyone needs to build what they can imagine. The more important skill is investing. If you learn to invest, you can build lasting wealth and bypass the gatekeepers […] The post Learning To Sell Is Just As Important As Learning To Invest appeared first on Financial Samurai.
Growing up, my dad would grab a quick breakfast with us before vanishing into the workforce. He'd resurface after 6pm, visibly depleted. The highlight reel of my childhood memories: throwing a ball around the backyard, some genuinely fantastic family dinners, and the times he watched me lose tennis matches and delivered his verdict — “you're just […] The post Dads No Longer Need To Feel Guilty Neglecting Their Children For Money appeared first on Financial Samurai.
The S&P 500 is up roughly 100% over the past three and a half years. At its historical average annual return of about 10%, you'd expect it to be up closer to 40% over that same stretch. That's an “excess gain” of 60%. I view this excess like free money you find on the street […] The post Use Your Excess Stock Market Gains to Actually Change Your Life appeared first on Financial Samurai.
After the final day of swimming and tennis at the sports club we're dropping, I took my kids to an open house in San Francisco. My wife was on a mom’s trip to Napa and I wanted to keep introducing my children to real estate, my favorite asset class. Maybe they might take a professional […] The post The Rise of Arrogant Listing Agents in A Hot Real Estate Market appeared first on Financial Samurai.
If you're one of the 8,000 Meta employees getting laid off in May, the difference between a good and great outcome could be worth $50,000 or more. The main reason for the layoffs the company mentioned is to offset their massive AI CAPEX. I've spent 14 years helping people negotiate severance packages, including engineering my […] The post Grading Meta’s Severance Package Offer: Strong On The Surface appeared first on Financial Samurai.
Earlier this year, I decided to give up cable to simplify my life and save $120 a month. I don't watch much TV, and when I do, it's sports. But with so little time, I watch the condensed 10-minute highlights on YouTube for free. Around the same time, I decided not to renew my Bay […] The post Giving Up My Sports Club Membership Despite the Health Benefits appeared first on Financial Samurai.
There are a lot of things wealth is good for, but one of the most underrated benefits is being able to buy peace and quiet. As I was sitting in the hot tub with my two children at Everline Resort in Lake Tahoe, I couldn't help but feel a little frazzled by all the noise. […] The post One Of The Best Benefits Of Wealth: Buying Peace And Quiet appeared first on Financial Samurai.
For those who work in AI, let me share a cautionary tale based on history. You may be getting incredibly rich right now, but there’s little point in being rich if your safety is constantly at risk. Back in 2008, I was working in finance at Credit Suisse Group in San Francisco. There were constant […] The post Be Safe and Live: Don’t Work in AI When the Revolution Comes appeared first on Financial Samurai.
One of the key ways to FIRE is to save and invest aggressively. You've forecasted your misery, therefore, you know that by the time your misery becomes a reality, you'll have invested enough money to retire early and break free from the grind. Obviously, if you don't forecast when you'll be miserable, you're probably not […] The post How To Convince Yourself To Invest Aggressively For A Better Tomorrow appeared first on Financial Samurai.
Every year or two, the market hands you a gift wrapped in anxiety. You watch your portfolio bleed, you refresh your brokerage app more than you should, and you feel helpless. But when you have children, that helplessness can flip into something more actionable. This past year, with the stock market getting crunched by geopolitical […] The post Investing More Than The Gift Tax Exclusion Limit Shouldn’t Be A Problem appeared first on Financial Samurai.
After publishing my piece on the shocking cost of eldercare, a question kept nagging at me that I couldn't shake: when money is finite and the people you love are not, how do you decide who to help or save first? A $230,000-a-year group home in Hawaii for one person. Four parents to potentially care […] The post A Financial Dilemma: Save Your Parents, Your Children, or Yourself appeared first on Financial Samurai.
At the Diamond Head pickleball courts in Honolulu, I met a man who said he had just put his 94-year-old mother in an eldercare home. Since my parents are 78 and 80, my ears lit up. I know it will be up to me to take care of them when they can no longer take […] The post The Shocking Cost of Eldercare Most People Underestimate appeared first on Financial Samurai.
I must live in a bubble. Because in my circle, I don't know anybody who has a car worth more than 1/10th of their annual gross income. I came up with the 1/10th rule for car buying over 15 years ago to help people achieve financial freedom sooner. Thousands have followed this standard rule since, […] The post Your Car Payment Is A Huge Roadblock To Financial Freedom appeared first on Financial Samurai.
As someone who's been writing about FIRE (Financial Independence Retire Early) since 2009 and actually leaving full-time work for good in 2012, it's been quite an interesting ride. For the most part, I've been lucky because the stock market and real estate market have generally trended up, except for in 2018 and 2022. 12 good […] The post FIRE Psychology During a Stock Market and Economic Downturn appeared first on Financial Samurai.
As a parent to two young children, I am a target client for universities everywhere. So far, I have saved over $800,000 in two 529 plans to pay for universities in 9 to 12 years. I know we need to pay full freight because we are nobodies with average intelligence, but make above the low […] The post American Universities Hiring H-1B Foreign Workers Seems Off appeared first on Financial Samurai.
Since 2009, I've been writing about all the ups and downs of my financial independence journey, the good and the bad. What I can clearly say is that who you partner with in life is one of the most important variables for achieving financial freedom. Get that right, and everything else gets easier. Get it […] The post My Wife Took The Kids And Left Me – Thoughts Appreciated appeared first on Financial Samurai.
In a previous post, I debated whether it’s better to buy a home with a bigger lot or an amazing view. One key point was that unlike increasing livable square footage, it’s nearly impossible to create or improve a view. Sure, you could add a level to peek over surrounding houses. But building a 1,000-square-foot new level […] The post How To Improve Your Home’s View With Foresight and Patience appeared first on Financial Samurai.
We all know that panicking is one of the ways investors lose money. Panic selling during the 2008–2009 global financial crisis may have put some investors into the permanent underclass. Not only did they lose money, they weren't able to benefit from the incredible recovery since. Panicking during the March 2020 lockdowns caused many people […] The post How Panic Lost Me Money In A Non-Investment Way appeared first on Financial Samurai.
Since I started Financial Samurai in 2009, I have been on a mission to help readers achieve financial freedom sooner rather than later. And one of the core strategies I keep coming back to is encouraging readers to get neutral on real estate by first buying a primary residence. Once you have secured your primary […] The post It Is Easier To Make Millions On A Home Than In Stocks appeared first on Financial Samurai.
One of the biggest fears workers have about retirement is losing their sense of purpose. That fear is not unfounded. It is one of the negatives of early retirement nobody likes talking about. For the first several months, maybe even a year, you may feel a little lost. The steady paycheck is gone. The camaraderie […] The post Finding Purpose After Retirement Is Easier Than You Think appeared first on Financial Samurai.
The Fundrise venture capital product, VCX, listed on the NYSE on Thursday, March 19, 2026, to remarkable success. It had a NAV of about $19 a share, opened at around $42, briefly rocketed to $125, then closed the day at $76. That is roughly a 300% premium to NAV and far beyond what I thought […] The post Stay Humble After a Large Investment Win: Scrub A Toilet appeared first on Financial Samurai.
At the end of 2024, a relative asked me for financial help. She was planning to leave her expensive money management firm at Goldman Sachs Asset Management, where she was being charged close to 1.5% in fees and placed in a series of esoteric GS funds that charged another 1–2%. I’m not a fan of double-dipping, so I […] The post I Fired Myself As Money Manager And It Feels Great appeared first on Financial Samurai.
One of the biggest conundrums parents face is managing their own emotions when a stock market, real estate market, or any other risk asset takes a dive. On one hand, it's painful to watch your portfolio shrink. Every dollar you lose represents time, the most valuable commodity of all. On the other hand, there's a […] The post A Crashing Stock Market Is Great For Our Children’s Future appeared first on Financial Samurai.
In poker, having position means you act last. And acting last is one of the most powerful advantages in the game. You can raise with nothing to push opponents into folding, call with a weaker hand without fear of getting re-raised, or simply check and do nothing when your cards are mediocre. Every option costs […] The post Having Position Is Only Valuable If You Use It Wisely appeared first on Financial Samurai.
Due to the U.S. and Israel's bombing of Iran, oil prices temporarily shot up to $120 per barrel (WTI crude). If the Strait of Hormuz gets completely shut down, perhaps oil prices might go to $150+ a barrel. This would create a tremendous tax on consumers everywhere. With yet another increase in a core living expense, […] The post How to Survive Higher Oil Prices After The Bombing Of Iran appeared first on Financial Samurai.
Recently, a home in the beautiful Forest Hill neighborhood of San Francisco was listed for $2.4 million. It had four bedrooms, three bathrooms, and a modest 2,250 square feet. The home had been remodeled about 15 years earlier. As we do with every open house, my wife and I made bets on what we thought […] The post The Pain Of Selling A Home Too Soon In A Rising Market appeared first on Financial Samurai.