1:12:21The 2024 Milly Awards
From My First Million · Published Jul 4, 2025 · Watch on YouTube
TL;DR
The hosts recap 2024 via personal awards categories. They discuss best investments (passive real estate through a family operator, trading against the All-In Podcast’s advice, and tipping generously with $20s), worst investments (active real estate ownership, selling during COVID panic, picking Unity over Nvidia), and life hacks (printed weekly planner, highs-and-lows Slack channel, bricking the p
Key insights
- Carrying $1,000 in $20s and tipping lavishly (e.g., leaving $100 on a $60 tab) produces personal happiness; the giver enjoys the reaction.
- A profitable contrarian strategy is to bet against the All-In Podcast’s explicit predictions: buying Bitcoin when they called it zero, buying Meta when Chamath shorted it, buying Google when they call
- Passive, tax-advantaged, uncorrelated real estate investments via a trusted operator can yield 30–40% annual returns with no hands-on work.
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