Tuesday, October 21, 2025

Jon Stewart Reminds Us of How WallStreetBets Exposed the Stock Market

“If this sounds insane, it’s because it’s insane.”

The line could very well sum up how Jon Stewart feels about the stock market. In the stock market episode of The Problem on AppleTV+, the host fondly reminisced about the GameStop Short Squeeze of 2021.

In the episode, Stewart discusses how the stock market is fundamentally flawed: it’s designed in a way that we’re not supposed to understand, and it took a bunch of Redditors on the subreddit r/WallStreetBets to help expose these flaws.

Stewart’s investment in this topic goes way back, he went back on Twitter right when the GameStop frenzy was blowing up Wall Street and got right to it.

After the episode, Stewart stopped by Reddit to do an AMA. Here are some of the most interesting parts of the session.

Stewart also answered some questions about his coverage of the 2008 crash.

And for posterity, here’s his interview with CNBC’s Jim Cramer.


Information for this briefing was found via the companies mentioned. The author has no securities or affiliations related to this organization. Not a recommendation to buy or sell. Always do additional research and consult a professional before purchasing a security. The author holds no licenses.

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