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How NOT to Make $1,000,000 (I Tried 17 Ways)

From My First Million · Published Dec 6, 2025 · Watch on YouTube

TL;DR

Sam Parr failed at ~17 businesses before making his first cash million at 31, with his path documented through high school flipping, a hot dog stand, illegal moonshine sales, a roommate app, poison ivy treatment arbitrage, and others.

Key insights

  • Sam developed his money-making skill (copywriting/marketing) through the hot dog stand, where he learned to sell in person, then realized he could write once and reach infinite people online instead o
  • The "gray hat phase" is a nearly universal pattern among entrepreneurs who later succeed—testing legally-risky or semi-legal business models (moonshine) is common before settling on legitimate approac
  • Three components are required to win in business: a money-making skill, tenacity/scrappiness (learned through being forced into it with no other choice), and project selection (learning through proces

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