105: The Ghost of Dot-Com Past is Haunting AI Investors (Part 2)

We're continuing our deep-dive into one of the most fascinating moments in market history: the dot-com bubble - and what happened after it burst. 

[This is part 2; listen to episode 101 for part 1!]
  
You’ve probably heard of companies like Pets.com, the infamous dot-com failure, and Amazon, which somehow survived a 90% stock collapse and went on to become one of the most powerful companies in the world. But what actually separated the companies that failed from the ones that survived?

Jess Inskip walks us through the key lesson investors learned the hard way: growth alone isn’t enough. Companies need a real “path to profitability” and “free cash flow.”

And here’s why this matters today:
Every time a new AI breakthrough hits the market, whether it’s DeepSeek, Claude, or the next big model, investors start asking the same question they asked during the dot-com era: Who will actually survive this technological shift?

Together we unpack:

• The rise and fall of Pets.com, the poster child of dot-com excess
• How Amazon survived a 90% crash and became a dominant company
• Why investors became obsessed with free cash flow and burn rate after the bubble
• How the crash reshaped the tech industry and investing behavior
• And why the ghost of the dot-com bubble is still haunting today’s AI boom

If you want to understand why markets react the way they do to revolutionary technology, this episode will give you the historical context that is showing up in markets todaaayy!

Make good choices. ;)
 

 Episode note:
About 23 minutes in, Jess mentions "bar codes," but she meant "QR Codes" - FYI.