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 include the most valuable companies, the richest people, the most capital and the best universities on the planet.
Yes, the competition is tough. But because of the abundant number of opportunities you dramatically increase the surface area of your destiny. And if you can’t compete professionally, you can always try marrying someone who is winning. I’m only half joking. Assortative mating is one of the biggest wealth-building forces that no one wants to talk about.
Think of it this way. Living in an expensive city is like playing crime. The growth in your income and equity is theoretically unlimited. Living in a cheap city is like playing defense. You can only cut costs so much before you’re stuck eating rice and beans in a house full of money and wondering what happened to your 30s. No one ever prospered from defense alone. To score you need offense.
After grinding it out professionally (and romantically) for 10 years, you can rest easy knowing that you put your best effort into it. If you make it rich, you will have countless options to transfer without any hassle. Or you can stay in your expensive city without much financial worries.
If you don’t fancy it rich, there are plenty of wonderful, more affordable cities waiting for you. However, alternation only flows in one direction. It is much easier to downshift from San Francisco to Des Moines than reverse.
When you’re on the path to financial freedom, go where the action is. Put your foot forward in any appropriate capacity, build a network and let serendipity do its thing. As many remote workers have found, out of sight actually means out of mind, and out of mind means lost opportunities.
High home prices are a positive sign, no knockdown
The typical three-bedroom, two-bathroom, ~1,800-square-foot home in San Francisco costs about $2.2 million. A family of four needs to make at least $400,000 a year, after putting 20% down, to feel somewhat comfortable affording one person. This does not include any help from parents, which about 40% of first-time home buyers now get.
Some people think the average price is excessive. But consider this: If you joined a company like Google in early 2023, your stock has increased nearly 4x since then. Meanwhile, the average home price in San Francisco rose nearly 30% over the same period, from $1.7 million to $2.2 million. In other words, for the well-off local worker, housing actually became more affordable, not less.
Instead of seeing high home prices as a sign of a negative cost of living, look at them as a sign of how financially well off you are. opportunity Present in the area. House prices are largely driven by the income and wealth of the people living there. These homes are expensive because not enough residents earn enough to pay for them. If they don’t do this, prices will fall.
Expensive cities have more income opportunities
The total compensation package for 23-year-old college graduates in big tech is between $150,000 and $200,000. Ten years later, these guys are easily making over $350,000. One of my tenants joined a leading AI in 2025 and has seen his equity package 5X in just one year. For him and his partner, they can easily pay $10,000 a month in rent for a five-bedroom, four-bathroom home.
So paradoxically, you should get excited About high house prices and buy one yourself, because money is sticky and attracts more money. Unless the geography or weather is terrible, or the government is corrupt, expensive cities will continue to get more expensive.
Sure, you may one day become so rich that the government will try to impose a special tax on you. Congratulations. At that time you can tolerate whatever the government says for you. Or, you can easily relocate and live like royalty.
The world’s best entertainment comes to you
Part of the deal with expensive cities here is that frugal people, especially frugal people like me, constantly underestimate entertainment.
When Team USA played a World Cup win-or-go-home knockout match with Bosnia and Herzegovina at Levi’s Stadium on July 1, I was 2,400 miles away in Honolulu, having left San Francisco the day before. A single-elimination World Cup match, 30 miles from my home, and I missed it.
To make myself feel better, I told myself I wasn’t willing to pay $1,500 to $2,000 per ticket for the middle seats. I certainly wasn’t willing to pay $6,000 to $8,000 for my family of four.
But while relaxing for free on the beach in Kahala, the truth dawned: I would have gone. I should have gone. The USA won 2-0 and earned their first World Cup knockout stage win since 2002 in my backyard, and I watched the highlights on my phone just like the US.
Fire may stop you from spending
Here’s the flawed FIRE argument I was attracted to: Why pay thousands to attend when you can watch it on TV for free? Because anyone can watch it on TV for free. The guy who went there to save money watches the same broadcasts I watch. The whole point of paying a premium to live in a world-class city is that the world’s biggest events come to you. If you never join them, you’re paying expensive-city cover charges and then being denied entry to the club.
Think about the fans who come. Levi’s Stadium attracts approximately 70,000 people for these matches. Thousands of them paid for flights, hotels, meals, ground transportation and tickets. If a Bosnia fan can justify a total of $10,000, then surely I can justify an Uber ride and a ticket. Of course I could.
When world-class entertainment comes to your expensive city, you go. This is the dividend you owe for paying more for housing, energy, education, and taxes than any other person on Earth. Skipping events is like owning a dividend stock and refusing to cash the check.
Recreational examples of what Bay Area Alone has hosted
Don’t take my word for it. Here’s a sampling of the world-class events that have taken place in the San Francisco Bay Area, which is about a 55-minute drive from my home. Try replicating this list in a low-cost-living paradise.
| events | When? | What happened |
|---|---|---|
| Ryder Cup (golf) | September 2033 (upcoming) | The Olympic Club hosts golf’s largest team competition, with the 2028 PGA Championship being held for the first time as a practice event. |
| fifa world cup 2026 | June-July 2026 | Six matches at Levi Stadium, capped by USA 2, Bosnia-Herzegovina 0 on July 1, the US’s first knockout-round win since 2002 |
| super bowl lx | 8 February 2026 | Seahawks 29, Patriots 13 at Levi’s Stadium, with Bad Bunny headlining at halftime |
| Laver Cup (tennis) | September 2025 | Team World defeated Team Europe 15–9 at the Chase Center, with Taylor Fritz defeating world No. 1 Carlos Alcaraz. |
| NBA All-Star Weekend | February 2025 | League’s best performance at Chase Center |
| taylor swift eraz tour | July 2023 | Two sold-out nights at Levi’s Stadium, the largest tour in music history |
| beyonce renaissance tour | August 2023 | Another global icon, same stadium, same heat |
| APEC summit | November 2023 | Biden, Xi and world leaders take over San Francisco |
| US Women’s Open (golf) | June 2021 | Following Lexi Thompson’s heartbreaking back-nine collapse, Yuka Saso defeated Nasa Hataoka in the Olympic Club playoffs to become the first Filipina major champion. |
| pga championship | August 2020 | Cal Berkeley product Collin Morikawa won his first major at TPC Harding Park with his famous drive on the 16th. |
| warrior dynasty | 2015–2022 | Four NBA titles (2015, 2017, 2018, 2022) and six Finals appearances, all playable individually |
| CFP National Championship | January 2019 | Clemson 44, Alabama 16 at Levi Stadium |
| super bowl 50 | 7 February 2016 | Broncos 24, Panthers 10, Peyton Manning’s final game |
| Copa America Centenario | June 2016 | Levi’s Stadium hosted matches in the historic US edition of the tournament. |
| wrestlemania 31 | March 2015 | Levi’s Stadium was packed with more than 76,000 fans |
| Giants World Series run | 2010, 2012, 2014 | Three titles in five years, with World Series games at Oracle Park |
| America’s Cup | September 2013 | Oracle Team USA makes a comeback from 8-1 down to win 9-8 over San Francisco Bay |
| US Open (golf) | June 2012 | Webb Simpson wins at The Olympic Club, the fifth U.S. Open held on those famous cypress-lined fairways |
And that’s just the marquee thing. Every year there’s Outside Lands, Hardly Strictly Bluegrass (a world-class music festival that’s virtually free), Fleet Week with the Blue Angels roaring over the bay, various professional tennis tournaments, startup conferences and demo days, and more Michelin stars per capita than almost anywhere in the country. This is what you get when you live in an expensive city and pay taxes.
When I lived in New York City, which was my favorite city in the world for six months a year, from 1999 to 2001, the Yankees won the World Series twice. Going to those games, seeing Broadway shows, eating at incredible restaurants, and going to random bars and warehouse parties was a blast. That’s expensive city life. Work hard, definitely. But you are never bored.
Crime makes money, but the point is freedom
After all, we are not building wealth for the masses. We are building wealth to be more independent and live a better life. If you play offense in an expensive city, you get both: more income and equity than you would earn by playing defense in a cheaper city, and easier access to the biggest events on Earth.
To be wealthy enough to participate in this tragedy and yet watch from your sofa is because the muscles of thrift will not relax. I’ve written before about how the hardest part of FIRE isn’t accumulating money, but giving yourself permission to spend it. Missing that World Cup match was my latest memory.
So this is my new rule, and I invite you to adopt it: If a once-every-four-years (or rare) event comes within an hour of your house, you go. No spreadsheet analysis. Not “Let me check the resale market on Wednesday.” Go. Memory dividends last much longer than money made in the S&P 500.
The next World Cup on home soil may not come again for decades. Next Super Bowl at Levi’s? Who knows. But there are always more cool things coming along, because that’s what expensive cities do. They put on a show.
Make sure you’re on the field, not on the couch.
Reader: Do you live in an expensive city, and do you really take advantage of the events happening in the city? Or have you moved somewhere cheaper and found the deal worth it? What’s the best live event that you almost skipped to save money?
wealth building tips
Invest passively in real estate: If seven-figure home prices in expensive cities make your eyes water, you can still play crime in real estate without a jumbo mortgage. I have invested over $500,000 raise fundWhich focuses on residential and industrial properties in the heartland, where valuations are low and yields are high.
Using my BURL method, earn 100% passive income while keeping your career capital concentrated in an expensive city, and having more fun. Financial Samurai is an investor in Fundrise, and Fundrise is a long-time sponsor of Financial Samurai.
Build Seven-Figure Wealth: If you want to accumulate enough wealth to afford both a trip to an expensive city and a ticket, pick up a copy of my USA TODAY bestseller, Millionaire Milestones: Simple Steps to Seven Figures. The sooner you reach seven figures, the sooner you’ll stop debating whether the good seats are worth it or not.
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