The Milly Awards 2021

About this video

Sam Parr, Shaan Puri, and guest Andrew Wilkinson return for the second annual “Milli Awards,” an end-of-year awards ceremony where the three hosts recognize standout businesses, investments, and products from 2021 across categories like Billionaire of the Year, Breakout Company, and Best/Worst Investments.

Key takeaways

• Shaan highlights Elon Musk’s bold bet-on-yourself compensation structure at Tesla, where he only earned equity after hitting a $100 billion market cap milestone and ultimately captured all future unlocks as the company surged to $1 trillion valuation.
• OpenSea emerged as the consensus breakout company, growing from $24 million in GMV in 2020 to $15 billion in 2021 (650x growth), though Andrew noted Pieter Levels’ one-person business climbing from $300k to $5 million annually as a unique lifestyle win.
• Shaan’s DEAL investment illustrates the power of follow-up: missing the $12 million seed round but entering a $200 million Series B at 1x valuation (a 458x return opportunity) teaches the lesson that timing and persistence in startup investing can mean a $10 million+ difference.
• Andrew and Sam both emphasized unsexy, high-margin businesses—from American Striping (70% profit margins on road line painting) to a fake private jet photo studio rental (70/hour, $20-40k/month)—as reliable wealth builders outside hype cycles.
• The hosts revealed mistakes like Shaan holding pandemic-winning tech stocks (Zoom, Fastly, Agora) too long and Sam losing 56% on Zillow after it misexecuted its house-buying pivot, illustrating the importance of knowing when to exit winning positions.

Episode details: published December 31, 2021 · 18K views · 1:47:34 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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