Why It’s So Hard To Leave San Francisco: Excitement, Fear, AI

I’ve been trying to leave San Francisco since 2014. After fake retiring in 2012, I thought it was only logical to move to a lower-cost area of the country, like Honolulu, to save money and be closer to my folks.

Yes, Honolulu isn’t cheap, but it’s cheaper than San Francisco! However, every time I try to leave, San Francisco pulls me back in.

Here are some reasons why:

  • 2014: Found an ocean-view home in San Francisco for cheap, so I bought it instead of buying a much more expensive ocean-view home in Honolulu.
  • 2017: Had our first child, so we decided to stay for continuity. As first-time parents, we had enough stress.
  • 2019: Had our second child. There’s a lot of comfort in knowing your doctors when you have a newborn.
  • 2020: The pandemic forced us to shelter in place for several months. Relocating to a new city with an infant and three-and-a-half year-old during a pandemic creates more uncertainty.
  • 2021: Son got into a Mandarin immersion school. He’s enjoyed his experience so far, so it’s hard to pull him out and place him in a new school.
  • 4Q 2023: An opportunity to purchase a dream home at a more affordable price, so we did.
  • Fall 2024: The possibility of going back to work full-time once both kids are in school full-time. The job opportunities are more plentiful in San Francisco than in Honolulu.

Having A Family Makes Leaving Any City More Difficult

If we didn’t have kids, I’m sure my wife and I would have relocated to Honolulu years ago. We longed to live a simpler life near the ocean in year-round warm weather. We had enough money to live comfortably, but not extravagantly.

I imagined fixing up my grandparents’ old farmhouse in Waianae and eating off the land. After breakfast, we’d go to the beach to boogie board or surf. Then we’d come home, eat some poké, and take a nap. Then we might go for a late afternoon hike.

Although we’d lose all status and prestige, we’d be mentally and physically healthier and happier! Not a bad trade over just making money. Alas, we had kids, which are a blessing.

Once you have a family, inertia makes it very hard to relocate. Your house, school, friends, network, and healthcare providers all keep you stationary.

Why I Love San Francisco

Besides America, I’ve lived between 6 months and 4 years in six other countries. I’ve also visited over 150 cities worldwide. San Francisco is on my list of the top five best cities in the world.

Here are the reasons why:

  • The weather is mild year-round, which is great for exercising outdoors.
  • The city and the surrounding region are beautiful, especially if you can live in a home with views.
  • Napa/Sonoma Valley are only an hour and 15 minutes away.
  • Lake Tahoe has world-class skiing/snowboarding 3.5 hours away.
  • Closer to Hawaii and Asia than cities on the East Coast.
  • Fantastic universities such as Berkeley, Stanford, UCSF, Santa Clara, etc
  • Always a top three culinary city in America
  • Bountiful job and consulting opportunities that pay well
  • One of the most diverse cities in the world
  • One of the cheapest international cities in the world
  • Tons of entertainment, like tennis tournaments, entertainers, and art shows come here

Why I Dislike San Francisco

Of course, no city is perfect. Here are some reasons why I dislike San Francisco:

  • Some corrupt city officials
  • Government waste
  • Crime and homelessness
  • High cost of living
  • Intense hustle culture in some industries
  • Bureaucracy when it comes to getting things done

But the reality is, every single city has these bullet points to various degrees. The one thing I love about Honolulu over San Francisco is the lack of hustle culture. Once you’ve left an intense career, you won’t want to be constantly surrounded by go-getters.

Excitement Is What Keeps Me In San Francisco

I’ve gone through the pros and cons of San Francisco many times before. But what I realized most recently is that excitement is one of the main reasons why I remain in San Francisco.

As someone who easily gets bored, I need to be in a vibrant city where there’s something exciting always going on. Let me share a couple of examples.

1) APEC Comes To San Francisco

San Francisco recently hosted APEC, the Asia Pacific Economic Council. President Biden, China’s President Xi, and a bunch of other world leaders came to hob knob.

As an Asian person who lived in The Philippines, Japan, Taiwan, and Malaysia until high school, it was exciting to see 21 APEC leaders come to town and build relationships. Here are some photos of who came to San Francisco for APEC.

Not only were world political leaders in town but so were top musicians like Sting and Yoshiki serenading Marc Benioff (Founder of Salesforce) and other luminaries at his event. Elon Musk came to town as well.

The world’s media was focused on San Francisco for two weeks. The spotlight brings in more interest, more investments, more jobs, and more demand to visit and live in the city.

It’s hard to leave San Francisco when you know many people want to live here.

2) OpenAI CEO Firing Debacle

After APEC ended, OpenAI’s board voted its CEO, Sam Altman out for an unspecified reason. After Atman’s firing, there was a huge outcry of support from the VC and tech community. Greg Brockton, the President quit, along with several senior researchers. As a result, the board is under immense pressure to resign and reinstate Altman as CEO.

If you’ve watched Succession on HBO, the entire OpenAI debacle feels like the show on hyperspeed. Exciting and fascinating to observe!

Once again, the entire tech world is focused on what the heck is going on in San Francisco with the largest artificial intelligence company in the world.

For a quick overview of what’s going on at OpenAI, the maker of ChatGPT:

  1. Altman clashed with the board on the direction of the company (e.g. profits vs. non-profit, AI safety, speed of development of technology, Altman wanting to start another company, etc)
  2. Power struggle between Altman and Ilya Sutskever, OpenAI co-founder and chief scientist
  3. In a coup by Sutskever, on a Google Meet, “Ilya told Sam he was being fired and that the news was going out very soon.” Shortly after, Brockman was told he was being removed from his position as chairman of the board but would hold on to his role as president. 
  4. Microsoft’s CEO Satya Nadella found out about the board’s decision just like the rest of us on Twitter, despite having invested over $10 billion in OpenAI. Interestingly, despite the investment amount, Microsoft doesn’t have a board seat.
  5. OpenAI employees were on the cusp of being able to sell their shares at a staggering $86 billion valuation. But now that valuation amount is looking suspect. OpenAI’s board may have torched tens of billions in shareholder value.
  6. Now OpenAI’s board is under pressure to reinstate Altman, who is considering coming back if the board is removed. But he’s not! Emmett Shear from Twitch is now interim CEO.
  7. Altman is joining Microsoft to lead a new AI project. Working for big tech seems like a disappointment for Altman, but a win for Microsoft to control more pieces and get an in-house AI technology. Altman could return to OpenAI, but only if the board is changed.
  8. As of November 22,, Altman and Brockman are returning to OpenAI and Bret Taylor and Larry Summer have joined the board.

If you’ve lived in San Francisco since 2001, as I have, you inevitably will know people involved in this drama. How could you leave? The awkwardness is going to be amazing during the next board meeting!

Be In The Right Place At The Right Time To Get Rich

Half the battle of getting rich and/or getting ahead is being in the right place at the right time. When you can easily meet decision-makers in person, it’s much easier to build relationships. And when you have good relationships, life gets easier.

I’m talking about getting a job or a consulting gig, getting your kids into school, raising money for your company or fund, starting a business, and more. If you’re a helpful and relatively nice person, you will get farther ahead than those who aren’t.

Hard To Get Back In Once You Leave San Francisco

If you leave San Francisco, like many did during the pandemic, there’s a fear you might never be able to get back in.

The job you vacated will have been taken by a hungry colleague. Your network will forget about you once you leave. And the prime property you owned will be scooped up by another family and not be available for the next 30 years!

I’ve lived in San Francisco since 2001 because I felt the tech/internet boom was here to stay. Yes, the dotcom bubble had burst in March 2000, but the groundwork was laid for Web 2.0.

Given I couldn’t get a job in tech, I bought public tech company stocks. Then I bought as much San Francisco real estate as I could afford. Picks and shovels for those who’ve been shut out!

It seems obvious that artificial intelligence will revolutionize the world again. However, this time, the stakes may be even higher because AI could eliminate my children’s jobs as well as yours.

Fear Keeps Me In San Francisco

With Web 1.0 and 2.0 companies, there was a greater possibility of getting rich by joining these companies or investing in them after they went public.

But with artificial intelligence, there seems like less opportunity given fewer people are needed to scale. These private AI companies are staying private for longer, shutting out public investors. In addition, artificial intelligence is a direct attack on eliminating jobs in many industries!

By staying in San Francisco, I feel like I’m acting as a loyal soldier of the Night’s Watch in the Game of Thrones. The White Walkers are coming to destroy us, it’s only a matter of time when. But when they do, I want to be here to defend my family!

I’m always thinking 10+ years ahead because you have to if you want to effectively plan for your future. With a three and six-year-old, I’m concerned for their futures.

From Non-Profit To Mega Profits In AI

OpenAI went from being a non-profit whose mission was to help humanity to being a for-profit company worth $86 billion and largely owned by Microsoft.


No matter what the OpenAI leaders say, the reason why the company became a for-profit company was to make tons of money for its leaders, owners, and employees.

This is Capitalism 101!

Think about it. No matter how rich you already are, you can’t help but want more money, more power, and more fame.

Listen to all the corporate speak you want from AI leaders promoting a “harmless technology” for the greater good of humanity. There will be positive benefits from AI for sure, such as medical research and breakthroughs. However, there will also be negatives as well, including massive disinformation, fraud, and millions of job losses.

ChatGPT and Claude.ai already scrapes the internet for data and makes it their own without given any attribution to creators like me. Yet, AI folks say this isn’t stealing. No wonder why Medium is blocking all AI crawlers from its content.

Investing In AI For My Family

So what is a dad of two kids and a stay-at-home spouse going to do? Accept reality and adapt!

There’s no way I can beat AI. As a result, I need to either work in AI or invest in AI companies determined to wipe my kind off the map.

Getting a lucrative AI job is going to be difficult. Everyone wants one. But investing in private AI companies is accessible to me, and now it is accessible to all of you through funds like the Fundrise Innovation Fund. `

I’ve already committed $1,000,000 in various private venture capital and venture debt funds which invest parts of their portfolios in AI companies.

I plan to invest another $500,000 in venture capital funds that invest in AI companies over the next three to five years.

If AI revolutionizes the world, then my investments will likely pay off. If AI turns out to be overhyped, then my children will likely still land good jobs.

A Parent’s Fear Is The Greatest Motivator

One of a parent’s fears is spending 18 years educating their children, then spending a small fortune sending them to college, then ending up with despondent adult children who can’t get jobs in their fields of study.

This fear is one of the reasons why I’m reluctant to encourage anybody to pay full retail for college. Going to a public college or community college is the way to go! Lower price equals less possibility for disappointment.

With AI, sadly, I think more high school and college graduates will find themselves underemployed and disillusioned in the future.

By thinking 20+ years ahead for my 3 and 6-year-olds, I can better hedge against potential career disappointments. If they can’t get relevant jobs that provide purpose, I’ll pull them aside one day and share a version of this note.

A Conversation To My Adult Kids

“Dear Son/Daughter,

We wish life wasn’t so cruel. You studied your hardest in school and did your best over the past five years to find a job in your field. We’re so proud of you because you tried!

Even though things might not have turned out as you planned, your mom and I are here for you. Don’t give up! Good things are yet to come.

We have a surprise for you. In 2023, your old man recognized the future and invested accordingly. Here are the proceeds from various AI investments we made.

You’re a grown adult now. Feel free to use the funds to pursue what you really want to do. Don’t forget to come visit sometime OK?

We love you,

Mom and Dad

So there you have it folks. There’s too much excitement, fear, and AI going on to leave San Francisco. Maybe in our 50s will we finally move to Honolulu. But not now. We need to protect our children’s futures.

Reader Questions

Anybody live in San Francisco and find it difficult to leave? Are you worried about artificial intelligence taking away jobs for your children as well? Besides working in AI and investing in AI, what else can we do to protect our financial futures?

Besides politics and not being able to afford to live on San Francisco, why else do some people who don’t live in San Francisco hate San Francisco so much?

A Way To Invest In Artificial Intelligence

In addition to investing in public companies like Microsoft, Nvidia, Snowflake, to gain AI exposure, you should also look to invest in private AI companies as well. Check out the Innovation Fund, which invests in the following five sectors:

  • Artificial Intelligence & Machine Learning
  • Modern Data Infrastructure
  • Development Operations (DevOps)
  • Financial Technology (FinTech)
  • Real Estate & Property Technology (PropTech)

Roughly 35% of the Innovation Fund is invested in artificial intelligence. In 20 years, I don’t want my kids wondering why I didn’t invest in AI or work in AI!

You can see what the Innovation Fund is holding before deciding to invest and how much. The minimum is $10. Traditional venture capital funds require capital commitment first and then hope the general partners will find great investments.

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