Why I'm changing how I invest my money because of AI
A top-tier angel investor explains how to use AI to improve investment decisions by finding hidden opportunities, red-teaming investment theses to identify risks, and building automated monitoring dashboards. He emphasizes only investing in areas where you have genuine expertise and unfair information advantages.
Summary
The speaker, a highly credentialed angel investor with ties to Google founders and Jay-Z, presents a framework for AI-enhanced investing that starts with a mindset shift from wealth preservation to wealth creation. He argues that money should be actively deployed to generate returns rather than protected passively. The core strategy involves three main stages: First, using AI to discover non-obvious investment opportunities by analyzing research papers, identifying second and third-order effects, and finding companies others overlook—such as electrical contractors benefiting from AI infrastructure buildout rather than obvious plays like Nvidia. Second, he advocates extensively for red-teaming investment theses using AI, prompting it to identify ten reasons why an investment could fail completely, then assessing whether each risk can be mitigated with confidence. He cites a personal example of nearly investing in a personal finance AI tool before AI red-teaming revealed competitive threats from major AI companies. Third, he recommends using AI to build automated dashboards that monitor all investments in real-time with color-coded alerts and weekly reviews. The speaker emphasizes three critical filters for any investment: genuine knowledge and unfair information advantage in that domain, sufficient capital commitment to maintain attention, and long-term alignment with future trends (10+ year horizon). He illustrates this with a Detroit real estate failure from 15 years ago and contrasts it with his recent Hark Labs investment in embodied AI for robotics, which passed all three filters. He concludes that the next decade will reward system builders who collaborate with AI to manage, test, and monitor their portfolios systematically rather than individual stock pickers.
Key Insights
- The speaker uses AI to analyze research papers across a field, finds common trends, correlates them with his business thesis, and uses this to identify investment sectors—rather than asking AI for obvious direct recommendations.
- The speaker claims that red-teaming nearly prevented a million-dollar loss on a personal finance AI tool by revealing that major AI companies would likely enter that market and outcompete the startup.
- The speaker argues that the best financial returns come from investments he almost made but rejected after red-teaming, not from deals he actually completed.
- The speaker experienced a $100,000 loss on Detroit real estate because he invested in something outside his expertise—homes were abandoned and unmaintained—which taught him to never invest outside his knowledge domain.
- The speaker predicts that over the next 10 years, investment success will shift from rewarding individual stock pickers to rewarding system builders who can collaborate with AI to track, test, and monitor their portfolios.
Topics
Transcript
[0:00] AI has completely changed the way I invest my money, and it's not the way you think. I was voted number one angel investor in Canada and have personally invested in dozens of companies with founders of Google, even Jay-Z. [music] And now with AI, I'm making way more money by investing in the right things and staying away from the wrong ones. So in this video, I'm going to show you the exact playbook on how to use AI to invest your money, starting with the very first move you need to make. Don't preserve it, create it. Wealth preservation sucks. Wealth [0:30] creation is super fun. Preserving wealth is like building a wall around your money. It…
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