Ever since two park rangers approached me at an empty public court while I was teaching my own children tennis, I've been thinking about how to make sure it never happens again. Not just to me. To anybody. The problem that afternoon wasn't that the rangers were doing their jobs. The problem was information. They […]
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Sotelo Avenue in Forest Hill is the most prestigious street to own a home in San Francisco. I know. Someone on Broadway just spit out their $28 espresso. Stay with me. For 25 years I've watched San Franciscans argue about neighborhoods when neighborhoods are the wrong unit of measurement. As a resident and multiple property […]
The post The 10 Most Prestigious Streets To Own A Home In San Francisco, Ranked appeared first on Financial Samurai.
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There are layers to freedom, and most of us only ever peel back two. The first layer is breaking free from your parents. Some people manage it the summer after high school. Others are still depending on dad to pay their new credit card charges at 37. The second layer is breaking free from work. […]
The post You’ll Never Be Free From The Government: Introducing The Leash Ratio appeared first on Financial Samurai.
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After reviewing dozens of financial tools on this site since 2009, ProjectionLab is one of the most comprehensive planning tools I've come across. It shows you how today's financial decisions play out over the next 10, 20, and even 40 years, with a modern interface that makes financial planning something you actually want to do. As a […]
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One of my biggest fears as a parent is raising kids who can’t launch into adulthood on their own. My hope is that by 26, three years after college to find their footing, they can support themselves without my money. If they can’t, I’m afraid I’ll feel like I failed them as a father. So […]
The post Real Adults Are Not Financially Dependent On Their Parents (But That’s OK) appeared first on Financial Samurai.
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Recently, I shared a sample budget of a family of four earning $408,000 a year on Twitter, the amount the latest data deems necessary to feel comfortable in San Francisco. The tweet received over three million views and more than a thousand responses. But the views aren't the story. The story is what I learned […]
The post Why Americans Are Richer, Happier, And Healthier Than You Think appeared first on Financial Samurai.
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Back in 2017, I wrote that households need to earn $300,000 a year to live a middle-class lifestyle in an expensive coastal city. The internet was not pleased. I was called out of touch, delusional, and a few other things I can't print on a family finance blog. After having a second child in December 2019, I […]
The post How Much A Family Needs To Earn To Live Comfortably By City: SF #1! appeared first on Financial Samurai.
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One of the greatest ironies in personal finance is that the people with the most money sometimes live the most uncomfortably. After spending another summer in Honolulu with my parents, I've been thinking hard about why. This post is a love letter to frugal parents everywhere. It's also a nudge for all of us adult […]
The post In Praise Of Unnecessary Suffering (Until It Does You In) appeared first on Financial Samurai.
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When Fundrise's Innovation Fund (VCX) listed on the NYSE on March 19, 2026, its net asset value was $18.97 a share. Within days, retail investors momentarily bid the price above $400. That's more than 20X NAV, a premium so rich it made 1999 look responsible. As a shareholder locked up until September 19, 2026, I've […]
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Before I die, I have a whole bucket list I want to get through. One item is experiencing what it's like to be a startup employee whose company goes public. If you're considering joining a startup, or already at one waiting for your lockup to expire, this post is for you. I spent 13 years in […]
The post What It’s Like Waiting Out A 6-Month IPO Lockup As A Startup Employee appeared first on Financial Samurai.
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I toured a $9 million house in Honolulu to better understand the luxury housing market. I love real estate, and visiting nice homes for sale is one of my favorite hobbies. My parents are 81 and 78 and live in Honolulu. Like many people their age, they have a few health issues, and I'd like […]
The post How The Rich Justify Buying $9+ Million Homes They Barely Use appeared first on Financial Samurai.
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With the World Cup on, I've been thinking about all the parents currently spending $3,500 to $7,000 a year on travel league soccer, dreaming their child might one day wear the national team jersey. Some elite club families are spending $8,000 to $15,000 a year once you add tournament travel, hotels, and private training. Watching […]
The post The Optimal Time to Stop Paying for Your Kids’ Activities appeared first on Financial Samurai.
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FIRE is ultimately about being set for life. You build a portfolio big enough to cover your expenses, and then your one job is to not blow it up. But here's the tension worth talking more about. The moment you give up your paycheck, you also give up your single biggest wealth-building engine: active income. […]
The post The Dumbbell FIRE Investing Method To Safely Build Max Wealth appeared first on Financial Samurai.
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If you want a greater chance of building more wealth than the average person, live in one of the most expensive cities in the world. These cities are expensive for a reason. They contain the most valuable companies, the richest people, the most capital, and the best universities on the planet. Yes, the competition is […]
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One of the reasons I want to live close to my parents is to help with the little things they don't feel urgency about. Back in 2023, I visited and asked why there was a hole in the kitchen ceiling with a rag on the floor beneath it. A leak, he said, though he wasn't […]
The post The Power Of Doing Nothing: How I Lost $120,000 By Not Waiting appeared first on Financial Samurai.
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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.
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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.
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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.
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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.
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