A common suggestion people gave me to help me regain my financial freedom was to move to a cheaper part of the country or world to save money. I have resisted the move until now because I believe the excitement of living in a big city is worth the price.
I have lived in big cities all my life. I was born in Manila (population 1.8 million), Lusaka (3 million), Kobe (1.6 million), Kuala Lumpur (1.8 million), Taipei (2.7 million), New York City (8.5 million) and now San Francisco. (810,000). Almost all I know live in big cities. As a result, it is difficult to change, especially with two children in school.
The thing is, there was a four-year period during high school where I didn’t live in a big city. I lived in McLean, Virginia (50,000), a suburb of Washington DC (5.6 million) 10 miles away. And guess what? I did not particularly enjoy the experience. There wasn’t much to do except go to the mall, hang out at McDonald’s, and mess with my friends.
If you thrive on other people’s strengths and consider yourself an extrovert, then living in a big city might suit you. If you’re actively working to build your net worth toward financial independence, larger cities may offer more financial opportunities. Conversely, if you identify as an introvert and/or have already achieved financial independence, you may prefer a quieter pace of life.
Despite the cost, living in New York City was the best
Moving from Williamsburg, Virginia (16,000), where I went to the College of William & Mary, to New York City was the most exciting time of my life.
Can you imagine moving from a small college town to the busiest city in America? I lived in a studio apartment at 45 Wall Street and walked 0.4 miles to One New York Plaza, where Goldman’s equities division was located.
Once you jam into the elevator that takes you to the 49th floor where the international traders are, you walk into a buzz that grows until the screams start when the stock exchange opens at 9:30.
If you went up the stairs to the 50th floor, the buzz got louder because the US equity section was five times bigger. Across the floor, the Goldman partners had their offices with glass windows.
I still remember when Dirty Dancing actor Patrick Swayze came to pay a visit. Every month, there seems to be some random celebrity making the rounds.
The Yankees win again!
When I started doing interviews for GS in 1998, the New York Yankees had just won the World Series. When I joined in June 1999, the New York Yankees repeated. Then they won again in 2000! I still vividly remember watching the parade come downtown from our window and then rushing to join in the frenzy for 15 minutes during my bathroom break. It was thrilling joy!
New York City knows how to spend your money. But the nightlife was amazing, the shows were world class, the food was to die for and the people were as diverse as could be.
It doesn’t matter what hour it was, you can always find something exciting. As an extrovert, I loved living in a shoebox in New York City on base salaries of $40,000 and $55,000 as a first- and second-year analyst.
When I “accidentally” got a phone call and my big boss said I wasn’t going to be renewed for a third year, my heart sank. So I interviewed at Bear Stearns, thanks for the good luck! The dotcom bubble burst and Wall Street began laying off people en masse.
My two-year stint in NYC is over. Fortunately, I was able to find a new job at Credit Suisse in San Francisco. A new adventure awaits.
A big step up in the excitement of living in San Francisco
Before coming to San Francisco in 2001, I visited the city once in college. A good friend of mine was attending UC Berkeley, so I thought I had a decent idea of the city. But I wasn’t prepared for how different the pace of life was compared to NYC.
Compared to New York, San Francisco was a sleepy city with only 1/10 the population. The bar closed at 1am and it was strange to have so much space to walk on the sidewalk. San Francisco was a downer in terms of excitement, but there was a good balance between work and life.
The moment that made me love San Francisco was a Friday afternoon my first winter there. It was raining so I decided to drive 2.5 hours away to the Sugar Bowl in Lake Tahoe. It only got 12 inches of fresh power snow and we had a blast on Saturday. Sunday, the sun was shining and I finished playing tennis in 68 degree weather and left my pecs sun kissed.
As a 25-year-old young buck, I was thrilled to have such a fun and affordable weekend stay. In New York City, I didn’t play tennis for two years because I was working all the time. Besides, there was no public place in the city to play. Private court cost $50-$80/hour, and you needed to know someone.
San Francisco is cheaper than Manhattan
I don’t care what anyone says, but San Francisco is cheaper than Manhattan. It was 30% cheaper in 2001, and it’s probably 40-70% cheaper today, depending on what type of property you’re buying.
Yes, I know there are cheaper boroughs to live in, like Queens. But I think it’s best to compare Manhattan to San Francisco. Brownstones in Manhattan are priced from $15 – $25 million and on lots <3,500 square feet. In San Francisco, you can get a similar property for just $5 - $10 million, but with a lot more land. What a deal!
The ability to make the same amount of money as in San Francisco, but live 30%+ cheaper was an advantage on my journey to financial freedom. Because the hours were also brutal (by 6am, regularly leaving after 5pm), I continued to save and invest as much as I could to escape one day early.
Since 2001, the excitement of living in San Francisco has improved thanks to:
- Internet boom and bust and boom again
- Doing my MBA part-time at Berkeley for three years and meeting new people
- The San Francisco Giants have won the World Series three times (2010, 2012, 2014).
- Attending countless startup meetups
- The GS Warriors have won the NBA championship four times
- Consulting with several fintech startups
- Explore Napa and Sonoma Valley
- Enjoying Lake Tahoe regularly in winter and summer
- America’s Cup Sailing Race
- Ryder Cup and US Open golf events
- Multiple professional tennis tournaments in Tiburon, Palo Alto and San Jose
- The 49ers reach the Super Bowl in 2020
- The 49ers are returning to the Super Bowl in 2024
This is what I understand from writing this list I love technology, entrepreneurship, making money and sports! New York City hooked me and San Francisco dutifully carried on the tradition. If you also like the above, you will enjoy living in a big city more than a small town.
The entire San Francisco Bay Area is buzzing about the 49ers squeaking by two teams in the playoffs. Everyone feels happy and excited again!
Too bad the Kansas City Chiefs will probably win again. But if the 49ers win, oh boy, what a win for the city.
The thrill of knowing something about warriors
Over the years, I got to know my friend Shaun Livingston, who won three NBA championships with the Warriors as a player. I got to hang out with him many times in the players lounge post game with family and friends. In addition, I went to one of the group’s events to talk about investing and crypto. It was interesting to go behind the scenes and experience what my sports heroes were doing.
As a Warriors fan, I would gladly take a $40,000/year job as a video coordinator because I get to travel and hang out with the team. A sports team friendship is the best kind of friendship. Alas, I often have to wait to leave my family behind until my kids are in college.
The power of the startup and VC community
In the winter, as a limited partner, I attend the Kleiner Perkins winter holiday party with my wife. There I mingled with other entrepreneurs and venture capitalists who were excited about the future. Oh, and the food and drinks were fantastic.
I can feel their energy as many are focused on building artificial intelligence companies to help humanity. Their drive inspires me to continue building on Financial Samurai. Getting to know some of these people also opens up new investment and partnership opportunities.
As an extrovert, I am not single but I am ready to meet! The thing I miss most about working in finance is all the holiday parties I got to attend. Each group had a wonderful time of celebration, appreciation and reflection.
With my platform, I can run my own angel fund or be a scout for one of the big VC companies. If so, that role will automatically get me deep into the VC community. To be a successful venture capitalist, I think it’s important to be in a place where you can meet your company regularly.
Moving to save costs isn’t worth the downgrade in excitement, though
I believe the excitement I get from living in a big city far outweighs the cost of living in a big city. Given everything is reasonable long-term, I’m currently willing to pay a premium to live in a big city. When the excitement is no longer worth it, I will change locations.
At 46, I’m still not ready to leave San Francisco. All I can figure out is that I’m too old and tired of trying before I’ve got one last beat in me. Maybe end up working at a startup or filming a TV show. Who knows. Being in a big city like San Francisco offers more unexpected opportunities.
When I’m ready to take things easy, in part because I’ve done everything I’ve wanted to do, I plan to move to Honolulu, Hawaii, a medium-sized city of about 350,000 people. I love Hawaii and the peace and tranquility it brings whenever I go home to visit my parents.
Doing some part-time consulting to fill my FIRE deficit isn’t a terrible proposition to fill the gap when my kids go to school full-time. I am eager to meet new people and try new things before I reach financial freedom again by 2029.
15 of my favorite big cities I’ve visited or lived in
- New York City
- San Francisco
- Hong Kong
- Kuala Lumpur
- in taipei
- in kobe
- Rio de Janeiro
Do you enjoy living in big cities? Are you always caught up in the excitement of what’s going on in the big city? Do you think that the cost of living in a big city is worth it? Do we change where we want to live as we get older and as our family circumstances change? What are some of your favorite big cities?
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