Why You Need Less Money Than You Think To Be Happy: A $40,000 Experiment

3 Comments / Budgeting & Savings / By

Back on June 30, I published Summer YOLO Fund: Permission To Spend, giving myself explicit written permission to blow through $40,000 in Honolulu this summer. The $40,000 was originally earmarked for investments in private startups after attending YC demo day. However, I wasn’t able to invest in companies I wanted, whether due to valuations or the […]

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Crushing Childcare Costs Are Why Cities Are Running Out Of Kids

25 Comments / Family Finances / By

I write before my kids wake up and after they go to sleep. That’s the arrangement. It means I’m free during summer, winter, and spring breaks, along with weekends, which is the whole point of building a lifestyle business in the first place. I gave up a handsome paycheck for the ability to always be the one

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A Backwards Tax Identification System For Determining Your Freedom

26 Comments / Retirement, Taxes / By

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 doesn’t happen 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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You’ll Never Be Free From The Government: Introducing The Leash Ratio

48 Comments / Retirement / By

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.

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ProjectionLab Review 2026: Best DIY Retirement Planning Tool

10 Comments / Product Reviews / By

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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Real Adults Are Not Financially Dependent On Their Parents (But That’s OK)

72 Comments / Family Finances / By

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

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Why Americans Are Richer, Happier, And Healthier Than You Think

35 Comments / Retirement / By

Recently, I shared a sample budget of a family of four earning $408,000 a year on Twitter, the amount third-party data deems necessary to feel comfortable in San Francisco. To be clear, this wasn’t my budget and it wasn’t a recommendation. It was an illustration of how fast a six-figure household income disappears once taxes, shelter,

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How Much A Family Needs To Earn To Live Comfortably By City: SF #1!

50 Comments / Family Finances / By

Back in 2018, 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

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In Praise Of Unnecessary Suffering (Until It Does You In)

22 Comments / Budgeting & Savings / By

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

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VCX NAV Estimate: What Fundrise’s Innovation Fund Is Really Worth

70 Comments / Investments / By

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 14, 2026 (now

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