I love startups and entrepreneurship. My obsession started when I was reselling Nerds candy in Taipei, purchased from the U.S. commissary store. To recognize and exploit a pricing arbitrage as a nine-year-old felt like winning the lottery every time a new batch arrived.
In 1998, a year before graduating from William & Mary, I was offered a chance to work at my father’s friend’s eyeglass parts factory in Shenzhen, China. The proposal was to be its manager and partner to expand into the country. China was finally opening up, and I had seen the rapid change firsthand as an exchange student in Beijing in 1997.
But I was nervous. I knew nothing about the business. Instead of taking the adventure of a lifetime, I took the sure thing: an international equities job at Goldman Sachs in New York City. Ever since, I’ve carried a mix of curiosity and mild regret. How would my life have turned out had I 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 figured if I was going to get laid off during the global financial crisis, I might as well build a backup. I never did get laid off, so I paid some guy $500 off Craigslist to get it up and running.
That’s when I started writing about FIRE and my plan to escape, which I finally did in 2012. Today the FIRE movement has grown worldwide, though as a founder I never fully capitalized on it.
I chose the bootstrapped lifestyle business over the VC-backed route because I no longer had the required motivation to seek maximum growth and profits. Jumping back into the fire and grinding for 12 to 15 hours a day was not appealing.
Being truly FIRE makes you a bad entrepreneur. You left your job because you weren’t financially motivated, and that doesn’t change. Turning Financial Samurai into a NerdWallet and aggressively pushing high-interest credit cards to maximize earnings felt bad. I mainly wanted to write about life, so I did.
Living in San Francisco since 2001, you can’t help but catch the startup bug. I lived through the dot-com bust, the Facebook and Google IPO era that minted thousands of new millionaires and drove up real estate prices, and now the AI wave creating fortunes all over again.
Meeting Startup Founders Will Make You A Believer
Recently, I attended the 2026 Startup Grind conference at the Fox Theatre in Redwood City. A golf buddy, James Gee, whom I met at a monthly Orrick/Vouch golf tech outing, was one of the organizers. James is Irish, can hit 320-yard bombs, and fell in love with startups, so we made a natural connection.
As someone who invests in private companies, is an LP in multiple venture funds, and has operated a private company since 2009, I love this conference. You should go to the next one.
I usually don’t sit in on more than one presentation a day, preferring to chat with people individually. But the lineup was so strong and the information so compelling that I ended up attending five presentations over two days. I also didn’t tell anyone I was going, wanting the freedom to move at my own pace after dropping off the kiddos at school.
Two major takeaways stood out.
First, if you are a builder or venture capitalist, you have to be in the San Francisco Bay Area. The energy is electric and the connections are endless. From waiting in line for an acai bowl to playing poker at a random networking event, you never know who you’ll meet. There is no replacing in-person relationship building. If you’re not where the action is, your chances of breaking through are vanishingly small.
Second, I am now firmly an “AI maximalist,” and you should consider becoming the same. Although I’ve been investing in private AI companies since early 2023, after realizing my editor father of 15+ years became expendable after ChatGPT launched, I hadn’t been entirely sure whether I was just living in a bubble. This is despite hundreds of readers of FS giving me their perspectives over the years.
However, after attending Startup Grind, I’m convinced: the rest of the country is not focusing nearly enough on AI. As a result, I’m not sure they are ready for what’s coming.
Key Takeaways From The Startup Grind Conference
Let me expand on the two points above and share several more.
1. Grit 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, what matters more is investing in founders with the grit to get things done.
Those who refuse to take no for an answer, who absorb feedback and keep iterating, make the most progress. You can never truly fail if you never quit. Be willing to pivot or start over if you hit a roadblock.
2. You have to be where the action is.
Saving money by living in a low-cost city is fine, 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, the co-founder of Harvey AI, a legal AI company I’m invested in through a fund, relocated from LA to San Francisco because they needed to be in the AI mix. Without that move, he doesn’t think he would have grown the company to its current $11 billion valuation. Gabe mentioned he still sleeps on the mattress on the floor of his apartment with no bed frame because there wasn’t the proper insurance when the movers came.
So much about building a successful company and growing outsized wealth is due to luck. However, you dramatically increase your luck by being where all the action is.
3. The first three to five seconds are everything for capturing attention.
Attention spans are shrinking. Whether it’s video or writing, if you can’t hook the viewer or reader in the first three to five seconds, you’ve likely lost them for good according to James Dumoulin. This is something I need to work as I tend toward long-form content with much deeper analysis.
4. Hire for agency and taste, not pedigree.
Their background doesn’t matter as much, said Amjad, CEO of Replit. Agency and genuine taste are what stand out. Since it’s much easier to build now due to AI, hire people with an entrepreneurial spirit.
5. Build AI-native or don’t bother.
Ashton Kutcher, actor and GP at Sound Ventures, was onstage with Warp CEO Ayush Sharma discussing the speed of change. AI-native companies can build faster and pivot more easily than legacy companies burdened with headcount and outdated systems. Eoghan McCabe, CEO of Fin.AI, interviewed by Kleiner GP Ilya Fushman, held a similar view.
This has important implications for investors. It’s hard to get excited about large, publicly listed SaaS companies, even though valuations are more compelling. It could take years for them to clean house, by which time AI-native companies will have lapped them. Please beware of value stocks, as structurally, their terminal values have changed.
Sadly, it’s hard to get excited about any private company that isn’t AI-native. I have portfolio companies in a couple of venture funds that are growing well, but I feel zero enthusiasm for them. AI-native companies are simply growing far faster, and I suspect other investors feel the same. The bar has changed.
6. International builders are driving the AI wave.
At poker and networking events in San Francisco, I’ve noticed the vast majority of attendees are foreigners and technically-oriented employees. The Startup Grind conference reflected the same, but they are the founders.
These are the founders who naturally hire people similar to themselves, and if these are the “best and brightest,” it’s no wonder top universities consistently admit a large share of international students: roughly 38% at Columbia, 24% at Stanford, and 18% at Berkeley. We must accept this trend.
If you are American and want to compete effectively, you need to be an American nerd with maximum grit. 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 allocating up to 20% of my investable capital to private AI companies was aggressive. In retrospect, I should have put 60% into private AI and 40% into the S&P 500 and public companies instead. I simply haven’t been bullish enough. Again, this goes back to how FIRE dampens the profit motivation.
And to be fair, accessing private AI companies is difficult. You need to know someone to get into a round or find the right venture fund with the right focus. Then once you commit capital, you can’t go back and commit even more capital if you notice the GPs are investing in great companies.
I recognized and invested in Fundrise’s venture product back in 2023, given I’ve been a partner of theirs since 2015. But like any investment that performs well, you always wish you had put in more.
Today’s Founders Are Genuinely Inspiring
Seeing founders full of energy, willing to work seven days a week for 10-plus hours a day, is motivating. I worked 60-plus hours a week for 13 years and burned out.
Now I spend about 12 to 15 hours a week on Financial Samurai, which is a walk in the park in comparison. But I know the correlation between hard work and reward is real. It’s odd to hear young people working only 40 hours a week or less complain that they can’t get ahead, when there are these smart startup folks working 80 hours a week.
The total addressable market for AI is the entire U.S. labor force, valued in the trillions. We don’t know which companies will win, but the ecosystem will keep growing, which is why real estate is a fundamental way play AI’s growth.
I’m an AI maximalist now, in part thanks to meeting the people building the future. I plan to invest more aggressively going forward, at least for my children’s sake. Because if I don’t invest for them, nobody will.
Readers, anybody else an AI maximalist? 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, not ready for what’s about to come?
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Financial Samurai is a promoter of the Empower Advisory Group, LLC (“EAG”), and is not currently a client.
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