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Latest Posts
A Backwards Tax Identification System For Determining Your Freedom
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…
The 10 Most Prestigious Streets To Own A Home In San Francisco, Ranked
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…
You’ll Never Be Free From The Government: Introducing The Leash Ratio
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. […]…
ProjectionLab Review 2026: Best DIY Retirement Planning Tool
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…
Real Adults Are Not Financially Dependent On Their Parents (But That’s OK)
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…
Why Americans Are Richer, Happier, And Healthier Than You Think
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…
How Much A Family Needs To Earn To Live Comfortably By City: SF #1!
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…
In Praise Of Unnecessary Suffering (Until It Does You In)
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…
VCX NAV Estimate: What Fundrise’s Innovation Fund Is Really Worth
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…
What It’s Like Waiting Out A 6-Month IPO Lockup As A Startup Employee
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…
How The Rich Justify Buying $9+ Million Homes They Barely Use
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…
The Optimal Time to Stop Paying for Your Kids’ Activities
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,…