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 cutthroat. But you dramatically increase your luck surface area thanks to the sheer number of opportunities. And if you can’t compete professionally, you can always try to marry someone who is winning. I’m only half joking. Assortative mating is one of the biggest wealth-building forces nobody wants to talk about.
Think of it this way. Living in an expensive city is playing OFFENSE. Your income and equity upside are theoretically unlimited. Living in a cheap city is playing DEFENSE. You can only cut costs so much before you’re eating rice and beans in a paid-off house wondering what happened to your 30s. Nobody ever got rich on defense alone. You need offense to score.
After 10 years of grinding it out professionally (and romantically), you can rest easy knowing you gave it your best shot. If you strike it rich, you’ll have an endless number of relocation options without feeling constrained. Or you can simply keep living in your expensive city without much financial concern.
If you don’t strike it rich, there are plenty of wonderful, more affordable cities waiting for you. The optionality only flows one direction, though. It’s much easier to downshift from San Francisco to Des Moines than the reverse.
When you’re on your path to financial independence, go where the action is. Get your foot in the door in any reasonable capacity, build a network, and let serendipity do its thing. As many remote workers have discovered, out of sight really does mean out of mind, and out of mind means lost opportunities.
High Home Prices Are A Positive Signal, Not A Knock
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 earn at least $400,000 a year, after putting 20% down, to feel somewhat comfortable affording one. This assumes no parental help, which roughly 40% of first-time homebuyers now receive.
Some think the median price is outrageous. But consider this: if you joined a company like Google in early 2023, your stock is up almost 4X since then. Meanwhile, the median San Francisco home price rose about 30% over the same period, from $1.7 million to $2.2 million. In other words, for the well-positioned local worker, housing actually got MORE affordable, not less.
Instead of viewing high home prices as a negative cost-of-living signal, view them as a signal of how much financial opportunity exists in the area. Home prices are largely driven by the incomes and wealth of the people living there. These homes are expensive precisely because enough residents earn enough to pay for them. If they didn’t, prices would fall.
Income Opportunities Are Higher In Expensive Cities
Total compensation packages for 23-year-old college graduates in big tech run between $150,000 and $200,000. Ten years later, these folks are easily earning 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, the $10,000 a month they pay in rent for a five-bedroom, four-bathroom house is easily affordable.
So paradoxically, you should get excited about high home prices and buy one yourself, because wealth is sticky and attracts more wealth. Unless the geography or weather is terrible, or the government is corrupt, expensive cities tend to keep getting more expensive.
Sure, you might one day get so wealthy the government tries to impose a special tax on you. Congratulations. At that point you can afford anything the government throws your way. Or, you can easily relocate anywhere and live like royalty.
The World’s Best Entertainment Comes To You
Here’s the part of the expensive-city bargain that frugal people, especially FIRE folks like me, consistently undervalue: the entertainment.
When Team USA played Bosnia and Herzegovina at Levi’s Stadium on July 1 in a win-or-go-home World Cup knockout match, 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 house, 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 middling seats. I certainly wasn’t willing to pay $6,000 to $8,000 for my family of four.
But while lounging on the beach in Kahala, for free, the truth crept in: I would have gone. I should have gone. The USA won 2-0 and earned its first World Cup knockout-stage victory since 2002, in my backyard, and I watched the highlights on my phone like most in America.
FIRE Can Prohibit You From Spending
Here’s the flawed FIRE logic I fell for: why pay thousands to attend when you can watch it on TV for free? Because ANYBODY can watch it on TV for free. The guy in the middle of nowhere who moved there to save money watches the same broadcast I do. The entire point of paying a premium to live in a world-class city is that the world’s greatest events come to YOU. If you never attend them, you’re paying the expensive-city cover charge and then refusing to enter the club.
Think about the visiting fans. Levi’s Stadium holds about 70,000 people for these matches. Tens of thousands of them paid for flights, hotels, meals, ground transportation, AND tickets. If a fan from Bosnia can justify $10,000 all-in, surely I could justify an Uber ride and a ticket. Of course I could.
When world-class entertainment comes to your expensive city, you go. It’s the dividend you’re owed for paying more for housing, energy, education, and taxes than almost anyone else on Earth. Skipping the events is like owning a dividend stock and refusing to cash the checks.
Entertainment Examples Of What The Bay Area Alone Has Hosted
Don’t take my word for it. Here’s a sampling of the world-class events that have come to the San Francisco Bay Area, all within a roughly 55-minute drive of my house. Try replicating this list in a low-cost-of-living paradise.
| Event | When | What Happened |
|---|---|---|
| Ryder Cup (golf) | September 2033 (upcoming) | The Olympic Club hosts golf’s greatest team event, with the 2028 PGA Championship coming there first as a warm-up act |
| FIFA World Cup 2026 | June–July 2026 | Six matches at Levi’s Stadium, capped by USA 2, Bosnia-Herzegovina 0 on July 1, America’s first knockout-round win since 2002 |
| Super Bowl LX | February 8, 2026 | Seahawks 29, Patriots 13 at Levi’s Stadium, with Bad Bunny headlining halftime |
| Laver Cup (tennis) | September 2025 | Team World beat Team Europe 15-9 at Chase Center, with Taylor Fritz stunning world No. 1 Carlos Alcaraz |
| NBA All-Star Weekend | February 2025 | The league’s best descended on Chase Center |
| Taylor Swift Eras Tour | July 2023 | Two sold-out nights at Levi’s Stadium, the biggest tour in music history |
| Beyoncé Renaissance Tour | August 2023 | Another global icon, same stadium, same summer |
| APEC Summit | November 2023 | Biden, Xi, and world leaders took over San Francisco |
| U.S. Women’s Open (golf) | June 2021 | Yuka Saso outlasted Nasa Hataoka in a playoff at The Olympic Club to become the first Filipina major champion, after Lexi Thompson’s heartbreaking back-nine collapse |
| PGA Championship | August 2020 | Collin Morikawa, a Cal Berkeley product, won his first major at TPC Harding Park with his famous drive on the 16th |
| Warriors Dynasty | 2015–2022 | Four NBA titles (2015, 2017, 2018, 2022) and six Finals appearances, all playable in person |
| CFP National Championship | January 2019 | Clemson 44, Alabama 16 at Levi’s Stadium |
| Super Bowl 50 | February 7, 2016 | Broncos 24, Panthers 10, Peyton Manning’s final game |
| Copa América Centenario | June 2016 | Levi’s Stadium hosted matches in the tournament’s historic U.S. edition |
| WrestleMania 31 | March 2015 | Over 76,000 fans packed Levi’s Stadium |
| Giants World Series Runs | 2010, 2012, 2014 | Three titles in five years, with World Series games at Oracle Park |
| America’s Cup | September 2013 | Oracle Team USA’s legendary comeback from 8-1 down to win 9-8 on San Francisco Bay |
| U.S. Open (golf) | June 2012 | Webb Simpson won at The Olympic Club, the fifth U.S. Open hosted on those famous cypress-lined fairways |
And that’s just the marquee stuff. Every single year there’s Outside Lands, Hardly Strictly Bluegrass (a world-class music festival that is literally 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. That’s what you get when you pay taxes living in an expensive city.
When I lived in New York City from 1999 to 2001, my favorite city in the world for six months a year, the Yankees won the World Series twice. Going to those games, catching Broadway shows, eating at incredible restaurants, and stumbling into random bars and warehouse parties was a blast. That’s the expensive-city life. Work hard, sure. But you’re never bored.
Offense Builds Wealth, But Freedom Is The Point
At the end of the day, we’re not building wealth for the sake of a bigger number. We’re building wealth to be more free and live a better life. If you play offense in an expensive city, you get both: more income and equity upside than you could ever generate playing defense in a cheap city, AND easy access to the greatest events on Earth.
The tragedy is being wealthy enough to attend and still watching from your couch because the frugality muscle won’t relax. I’ve written before about how the hardest part of FIRE isn’t accumulating money, it’s giving yourself permission to spend it. Missing that World Cup match was my latest reminder.
So here’s my new rule, and I invite you to adopt it: if a once-every-four-years (or rarer) event comes within an hour of your home, you go. No spreadsheet analysis. No “let me check the resale market Wednesday.” You go. The memory dividend compounds far longer than whatever that money would have earned in the S&P 500.
The next World Cup on home soil probably won’t come back for decades. The next Super Bowl at Levi’s? Who knows. But something else spectacular is always coming, because that’s what expensive cities do. They put on a show.
Make sure you’re in the arena, not on the couch.
Readers: Do you live in an expensive city, and do you actually take advantage of the events that come to town? Or have you moved somewhere cheaper and found the trade-off worth it? What’s the best live event you almost skipped to save money?
Wealth-Building Suggestions
Invest In Real Estate Passively: If seven-figure home prices in expensive cities make your eyes water, you can still play offense in real estate without a jumbo mortgage. I’ve invested over $500,000 with Fundrise, which focuses on residential and industrial properties in the heartland, where valuations are lower and yields are higher.
Earn income 100% passively, using my BURL method, while keeping your career capital concentrated in an expensive city, while 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 build enough wealth to afford both the expensive city AND the tickets, pick up a copy of my USA Today bestseller, Millionaire Milestones: Simple Steps to Seven Figures. The sooner you get to seven figures, the sooner you can stop debating whether the good seats are worth it.
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