The 2022 Milly Awards (#401)

About this video

Sam Parr and Shaan Puri host their third annual Melee Awards, a season finale celebration where they and guest Andrew rank and award winners across categories like Billy of the Year, breakout companies, best and worst investments, and favorite content. The episode features brainstorming, debate, and reflections on 2022’s biggest business moments and personal lessons.

Key takeaways

• Sam argues Palmer Luckey deserves Billy of the Year for taking his own capital seriously and being honest without a PR filter, while Shaan highlights Syed Saeed for building a WordPress empire while maintaining work-life balance through intentional time management
• Andrew’s biggest loss was lazily taking time-seller calls on the app Intro despite having built larger wealth, illustrating how founders can slip into short-term thinking that contradicts long-term wealth building
• Sam’s worst investment was fighting a petty court battle with a landlord over a $20k dispute; after four weeks of mental exhaustion, he paid the full amount and learned the value-destroying lesson of wrestling with pigs who have infinite time
• Open AI’s ChatGPT emerges as the breakout company moment, with Paul Graham’s 2009 prediction of Sam Altman’s trajectory proving prescient—Graham noted Altman had such force of will that he would get whatever he wanted
• Andrew’s best investment was buying the distressed Girlboss business for cheap after it failed in venture mode, then rebuilding it through basic fundamentals (newsletters, ads, affiliate)—now generating annual profit equal to purchase price
• Real estate investing underperformed for both Sam and Shaan relative to opportunity cost; Shaan regrets owning property and would prefer passive fund stakes, while Andrew sees steady 15-30% cash returns from buying whole businesses outperform illiquid venture portfolios

Episode details: published December 29, 2022 · 40K views · 1:55:03 long. Summary written by Self Growth Videos from the episode itself. The business ideas, figures and results discussed are the hosts’ and guests’ own claims, shared as brainstorming and entertainment — not verified facts and not investment advice.

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