I love startups and entrepreneurship. My obsession began when I was reselling Nerds candy I bought from an American commissary store in Taipei. Recognizing and exploiting pricing arbitrage as a nine-year-old kid feels like winning the lottery every time a new batch comes out.
In 1998, a year before I graduated from William & Mary, I was given a chance to work at my father’s friend’s eyeglass parts factory in Shenzhen, China. The proposal was to make it its manager and partner for expansion in the country. China was finally opening up and I witnessed the rapid change firsthand as an exchange student in Beijing in 1997.
But I was nervous. I didn’t know anything about business. Instead of setting off on the adventure of a lifetime, I took the sure thing: an international equities job at Goldman Sachs in New York City. Since then, I have been filled with a mixture of curiosity and mild regret. What would my life have been like if I had jumped on that entrepreneurial path in 1999?
Launched my own startup in 2009
In 2009, I decided to stop stalling and start Financial Samurai. I thought I might as well prepare a backup in case I got laid off during the global financial crisis. I’ve never been fired, so I paid someone off Craigslist $500 to get it going.
That’s when I started writing about FIRE and my plan to escape, which I eventually did in 2012. Today the FIRE movement has grown worldwide, although as a founder I never took full advantage of it.
I chose the bootstrapped lifestyle business instead of the VC-backed route because I no longer had the motivation needed to achieve maximum growth and profits. Jumping back into the fire and grinding for 12 to 15 hours a day was not attractive.
Being FIRE actually makes you a bad entrepreneur. You quit your job because you weren’t financially motivated, and that won’t change anything. It felt bad to turn Financial Samurai into NerdWallet and aggressively promote high-interest credit cards to maximize earnings. I wanted to write mainly about life, so I wrote.
Living in San Francisco since 2001, you can’t avoid catching the startup bug. I’ve lived through the dot-com crisis, the Facebook and Google IPO era, which gave birth to thousands of new millionaires and sent real estate prices soaring, and now the AI wave is making fortunes again.
Meeting Startup Founders Will Make You a Believer
Recently, I participated in 2026 Startup Grind Conference At the Fox Theater in Redwood City. A golf friend, James G., whom I met at the monthly Orrick/Vouch golf tech outing, was one of the organizers. James is Irish, can hit a 320-yard bomb, and he loves startups, so we made a natural connection.
As someone who invests in private companies, is an LP in several venture funds, and has run a private company since 2009, I love this conference. You should move on to the next one.
I don’t usually sit through more than one presentation a day, preferring to interact with people in person. But the lineup was so strong and the information so impressive that I had to attend five presentations in two days. I didn’t tell anyone I was going, wanting the freedom to go at my own pace after dropping the kids off at school.
Two major findings emerged.
First of all, if you are a builder or venture capitalist, you must live in the San Francisco Bay Area. Energy is electrical and the connections are infinite. From waiting in line for the ACE Bowl to playing poker at a random networking event, you never know who you’ll meet. There is no substitute for personal relationship building. If you’re not where the action is, your chances of succeeding are very slim.
Second, I am now firmly an “AI Maximalist” and you should consider becoming the same. Although I have been investing in private AI companies since early 2023, after realizing that the 15+ years my editor father had become expendable after ChatGPT launched, I wasn’t entirely sure if I was just living in a bubble. This is when hundreds of FS readers have given me their perspective over the years.
However, after participating in Startup Grind, I am convinced: the rest of the country is not focusing enough on AI. As a result, I’m not sure they’re prepared for what’s to come.
Key Takeaways from the Startup Grind Conference
Let me expand on the two points above and share a few more.
1. Patience matters more than intelligence.
Smart and motivated people are everywhere. High intelligence is standard among startup founders. But since AI is now the most intelligent tool available, it makes more sense to invest in founders who have the patience to make things happen.
The people who refuse to take ‘no’ for an answer, who absorb the feedback and keep repeating it, make the most progress. You can never truly fail if you never give up. Be prepared to turn or start over if you hit an obstacle.
2. You have to be where the action is.
It’s fine to save money by living in a low-cost city, but you can only save so much. You must focus on growth, and growth happens where companies, human capital and financial capital are already concentrated.
For example, Gabe, co-founder of Harvey AI, a legal AI company I have invested in through a fund, moved from LA to San Francisco because he needed to be in the AI mix. Without that move, he doesn’t think he would have been able to grow the company to its current $11 billion valuation. Gabe mentioned that he still sleeps on a mattress on the floor of his apartment without a bed because he did not have proper insurance when the movers came.
A lot about building a successful company and growing a large fortune is down to luck. However, by living where all the action is, you dramatically increase your luck.
3. The first three to five seconds are everything to capturing attention.
The scope of attention is shrinking. Whether it’s video or writing, if you can’t hook a viewer or reader in the first three to five seconds, you’ve probably lost them forever, according to James Dumoulin. This is something I need to work on as I gravitate towards longer-form content with more in-depth analysis.
4. Hire for agency and taste, not pedigree.
Replit CEO Amjad said their background doesn’t matter that much. Agency and genuine taste are what stand out. Since manufacturing is now much easier due to AI, hire people with an entrepreneurial spirit.
5. Make AI-native or don’t bother.
Ashton Kutcher, actor and GP at Sound Ventures, was on stage with Warp CEO Aayush Sharma to discuss the pace of change. AI-native companies can build faster and scale more easily than legacy companies burdened with headcount and legacy systems. Fin.ai CEO Eoghan McCabe had a similar view when interviewed by Kleiner GP Ilya Fushman.
This has important implications for investors. It’s hard to get excited about large, publicly listed SaaS companies, even when valuations are more attractive. It may take years for them to clean their house, by which time AI-native companies will have taken advantage of them. Please be careful with value stocks, because structurally, their terminal values have changed.
Sadly, it’s hard to get excited about Any Private company that is not AI-native. I have portfolio companies in some venture funds that are growing well, but I don’t feel any enthusiasm for them. AI-native companies are growing very fast, and I suspect other investors feel the same way. Times have changed.
6. International builders are riding the AI wave.
At poker and networking events in San Francisco, I have noticed that the majority of attendees are expats and technically oriented employees. The same thing was echoed at the Startup Grind conference, but they’re founders.
These are founders who naturally hire people like themselves, and if these are the “best and brightest,” it’s no surprise that top universities consistently accept a large share of international students: about 38% at Columbia, 24% at Stanford, and 18% at Berkeley. We have to accept this trend.
If you’re American and want to compete effectively, you have to be an American idiot with maximum patience. Otherwise, you have no chance. The smartest and hungriest people from around the world are coming to the SF Bay Area to build.
7. Most people haven’t invested enough in AI.
I thought it was aggressive to allocate up to 20% of our investable capital to private AI companies. Looking back, I should have instead invested 60% in private AI and 40% in S&P 500 and public companies. i just not fast enough. Again, this goes back to how FIRE reduces the profit motivation.
And to be fair, private AI companies are hard to get access to. To join a round or find the right venture fund with the right focus, you need to know someone. Then once you put up the capital, you can’t go back and put up even more capital if you see that the GPs are investing in great companies.
I discovered and invested in Fundrise’s venture product in 2023, even though I have been their partner since 2015. But like any investment that performs well, you always wish you had invested more.
Today’s founders are truly inspiring
It’s inspiring to see founders full of energy, willing to work 10+ hours a day, seven days a week. I worked 60+ hours a week for 13 years and was exhausted.
Now I spend about 12 to 15 hours a week on Financial Samurai, which is like a walk in the park in comparison. But I know that the relationship between hard work and reward is real. It’s strange to hear young people working only 40 hours a week or less complaining that they can’t get ahead, while these smart startup people work 80 hours a week.
The total addressable market for AI is the entire US labor force, valued in the trillions. We don’t know which companies will win, but the ecosystem will continue to grow, which is why real estate is a fundamental way for AI to develop.
I’m now an AI maximalist, thanks in part to meeting the people who are building the future. I plan to invest more aggressively going forward, at least for the sake of my children. Because if I don’t invest for them, no one will.
Readers, are there any other AI maximalists? Do you think the SF Bay Area is living in an AI bubble? Or do you think the rest of the world is living in an AI bubble, unprepared for what’s to come?
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