Reflections on past investment strategies focused on undervalued companies and long-term holding, caution against day trading, and recommendation of index funds for most investors.
I made the greatest trade of my life with Jesse Beyroutey in 2019. We bought Nvidia shares when they were trading at $33. They’re worth nearly $800 today.
I sat down with Jesse to top that trade in 90 minutes using Gemini Pro 1.5’s incredible 1 million token context window—and make a $1,000 trade live on the show.
Jesse is a managing partner at IA Ventures, a $600 million venture fund with seed investments in companies like Wise and Digital Ocean. He’s also a very close friend and one of the smartest people I know.
We unpack our investment thesis for our Nvidia trade and leverage the power of Gemini Pro 1.5 and ChatGPT to orchestrate what we hope will be the best trade of our lives. We put our money where our mouth is and make a $1,000 trade while the cameras are still rolling.
There’s a plot twist at the end of this episode—so stick around to see the epilogue Jesse and I recorded just days after we made our investment.
We get into:
- How Jesse leverages LLMs to get nuanced answers to his questions
- Ways to find patterns in large swaths of data using Gemini Pro 1.5
- Gemini Pro 1.5 and ChatGPT going head-to-head
- How Gemini Pro 1.5 can be used to understand the stock market
- Why it’s important to consistently refine your search queries
- What Jesse thinks are the new big opportunities enabled by LLMs
This is not investment advice, but it’s a must-watch for anyone who wants to leverage the power of AI to make smarter financial decisions.
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To hear more from Dan Shipper:
Timestamps:
- Introduction: 01:29
- How Dan made the greatest trade of his life: 03:50
- Jesse’s strategy to use LLMs to get nuanced answers 05:27
- Gearing up to orchestrate the best trade of our lives with Gemini Pro 1.5 09:20
- How Jesse gets AI to make great decisions 17:52
- Using Gemini Pro 1.5 to find patterns in data 22:38
- How AI can provide deeper insights into the stock market 26:48
- Leveraging Gemini Pro 1.5’s huge context window to analyze data 34:41
- Gemini Pro 1.5 and ChatGPT go head-to-head 46:33
- Choosing a stock with just 15 minutes left on the clock 1:10:11
- What Jesse thinks are the biggest new opportunities enabled by LLMs 1:24:01
- The epilogue Jesse and Dan recorded one week after making the trade 1:28:43
Links to resources mentioned in the episode:
Follow Jesse Beyroutey
Nathan Labenz’s podcast, The Cognitive Revolution
