Let's dive into the fascinating world of startups and the AI revolution, shall we? I'm an avid believer in the power of entrepreneurship, and my journey began with a simple candy-reselling venture in Taipei. Fast forward to 1998, and I had the chance to embark on an entrepreneurial path in China, but I chose the 'sure thing' instead, joining Goldman Sachs. That decision has lingered in my mind ever since.
In 2009, I finally took the leap and started Financial Samurai, my own lifestyle business. I chose the bootstrapped route, focusing on writing about life rather than aggressively pushing for growth. Being financially independent (FIRE) has its perks, but it can also make you a less motivated entrepreneur. I wanted to write, not aggressively promote high-interest credit cards.
Living in San Francisco, I've witnessed the dot-com bust, the rise of Facebook and Google, and now, the AI wave. It's an exciting time, and attending the 2026 Startup Grind conference only reinforced my belief in the power of AI.
The Energy of the Bay Area
One of the key takeaways from the conference was the importance of being where the action is. The San Francisco Bay Area is electric with energy and endless connections. It's a hub for companies, human capital, and financial capital, and being a part of that ecosystem can dramatically increase your luck and opportunities. I mean, just think about Gabe from Harvey AI, who relocated from LA to SF and saw his company skyrocket to an $11 billion valuation. That's the power of being in the right place at the right time.
AI Maximalism
After the conference, I became an 'AI maximalist.' I realized that the rest of the country isn't focusing enough on AI, and I believe they're not ready for the changes that are coming. As an investor in private AI companies, I've seen the potential and the speed at which these companies can grow. AI-native companies have an edge over legacy companies, and as an investor, it's hard to get excited about anything else.
Key Insights from the Conference
- Grit Over Intelligence: While intelligence is important, grit is what truly matters in the startup world. Founders who refuse to take no for an answer and keep iterating are the ones making progress. It's a mindset of never truly failing if you never quit.
- Attention Spans: In today's world, you have mere seconds to capture someone's attention. Whether it's video or writing, hook them in the first few seconds, or you've likely lost them.
- Hire for Agency and Taste: When building a team, look for agency and genuine taste. Hire people with an entrepreneurial spirit, as it's easier to build with AI.
- Build AI-Native or Forget It: AI-native companies have an advantage in speed and agility. As an investor, it's hard to get excited about large, publicly listed SaaS companies that might take years to adapt.
- International Builders: The AI wave is being driven by international builders and founders. Top universities are admitting a large share of international students, and if they're the 'best and brightest,' we need to accept this trend.
- Invest in AI: Most people haven't invested enough in AI. I, for one, wish I had allocated more of my capital to private AI companies. It's a bull market, and AI is where the growth is.
The Inspiration of Founders
Seeing founders full of energy and willing to work tirelessly is inspiring. Their hard work and dedication are a reminder of the correlation between effort and reward. It's a stark contrast to those who complain about working 40 hours a week or less. The total addressable market for AI is massive, and the ecosystem is only going to grow. Real estate, for example, is a fundamental way to play AI's growth.
So, readers, are you AI maximalists too? Do you think the SF Bay Area is in an AI bubble, or is the rest of the world not ready for the AI revolution? It's an exciting time, and I, for one, plan to invest more aggressively, especially for my children's future. After all, if I don't invest for them, who will?
