How to Make and Lose a Million Dollars
April 1, 2026
1 hr 6 min
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423 of 439
April 1, 2026
How to Make and Lose a Million Dollars
0:00 / 1:06:14
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Lost Debate Episodes Around April 1, 2026
Episode 423 of 439 — walk the feed in the order it was published.
1:06:14This episodeHow to Make and Lose a Million Dollars
Summary
Ravi Gupta sits down with Alexander Hurst, author of Generation Desperation, to unpack his journey from $300 to over $1 million—and the identity he built around the life that money seemed to promise. As his portfolio surged during COVID, meme stocks, and the rise of online trading culture, so did a vision of becoming financially free, creatively unbound, and finally ahead. When the gains reversed and turned into debt, it forced a reckoning—not just with risk, but with how deeply a sense of self can become tied to numbers on a screen. It’s a candid conversation about ambition, illusion, and what his story reveals about a generation pushed to gamble for a different life.
Alexander Hurst’s Generation Desperation
Ravi’s recent substack, Turning the Camera On
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