Real Estate

Toward the end of 2023, we upgraded to a larger finished home we didn’t need. Three years later, I want to share whether it was worth it, so you can make a better decision if you’re tempted to do the same. More than any other material item money can buy, a home is the most

At almost 50, I’m never doing a gut remodel again. Everyone who has survived one has the same thousand-yard stare. It’s the look of someone who spent two years arguing about grout color and waiting on inspectors who never show up when they say they will. Remodeling might be the most unpleasant thing you can

Part of the American dream is to climb the property ladder and live in the nicest neighborhood possible. We spend more than half our lives at home, so we want a neighborhood that offers as much peace, quiet, safety, and convenience as our budget allows. As an old man with young kids, long gone are the days

I have been a landlord since 2005, the year I rented out the very first property I bought in San Francisco after buying a single-family home. Since then I’ve been through all sorts of disputes. Neighbors texting me that my tenants were running across their roofs during Fleet Week. A heaping pile of trash left

Housing affordability is at a crisis low. You’ve read that headline a hundred times. Either incomes rise or home prices crash to get back to pre-COVID levels. That’s true if you measure a home in dollars earned. It’s not true at all if you measure one in shares owned. Every affordability index compares income to

This summer I toured a couple of 6,000 to 7,000 square foot mansion in the Kahala neighborhood of Honolulu, all in preparation for a potential move in two or three years. We plan to move back for either 6th or 7th grade for our son and 3rd or 4th grade for our daughter, so we

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 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?

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

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