05/29/2026
Enzo asked a great question this morning:
“Hey Dad, I heard ChatGPT and Claude might go public. Which IPO is going to make me richer?”
Before we even talk about OpenAI or Anthropic, there’s one rule we follow with every IPO:
🚨 Don’t buy it right away.
Most IPOs are driven by hype in the beginning. We want to give it at least 6 months to see if the excitement is real or if Wall Street starts finding problems. Patience beats FOMO.
Then we look at the 3 things that drive stock prices:
✅ Government policy
✅ The economy
✅ Company performance
OpenAI has some huge advantages. ChatGPT is the most recognized AI product in the world, it’s used by millions of consumers, it’s backed by Microsoft, and it currently appears to have a stronger position with government adoption and AI leadership initiatives.
The concern? OpenAI is spending enormous amounts of money on chips, infrastructure, and data centers. The big question is whether all that growth eventually turns into strong profits.
Anthropic, the company behind Claude, is a little different. It’s more focused on businesses and enterprise customers, and it’s backed by Google. While it may not have the same consumer recognition as ChatGPT, many companies are adopting Claude for business, coding, security, and productivity use cases.
My personal view?
Consumers may spend $20 per month on an AI subscription, but businesses can spend millions.
That’s why I think enterprise AI may be the bigger long-term opportunity. If businesses continue adopting Claude at scale, Anthropic could become a very powerful company over time.
But here’s the key: I don’t know which one will win.
The smartest move isn’t predicting the winner today. It’s waiting for the IPO, studying the numbers, and seeing which company can actually grow revenue and generate profits.
Investing isn’t about hype. It’s about ex*****on.