2025 Milly Awards LIVE ft. Steph Smith

About this video

Sam, Shaan, and guest Steph Smith reflect on 2024 through rapid-fire categories including best and worst investments, biggest personal losses, notable people they met, and coolest moments. The hosts discuss portfolio returns, personal growth experiences, and meaningful encounters with entrepreneurs and influencers.

Key takeaways

• Sam’s best investment was moving to New York City and purchasing discounted furniture from previous tenants, prioritizing proximity to family and in-person office work over possessions
• Shaan made a $1.25M one-day stock purchase split across Shopify, Tesla, Eli Lilly, Bitcoin, Coinbase, and Google that returned approximately 35% blended average, driven partly by Eli Lilly’s 35% gain after learning about their GLP-1 drug candidate
• Shaan identified three missed $10B+ investment opportunities (Polymarket, Khi, Whatnot) where he had early access but failed to commit, representing significant opportunity costs
• Angel investing typically requires surviving a difficult year 3-4 distribution phase before winners materialize; success depends on hitting a few breakout deals rather than consistent returns across the portfolio
• Shaan learned piano for a year as his ‘misogi’ (Japanese concept of a defining annual challenge) and played for Jesse Cole and Sarah Blakely at Cole’s home, resulting in an emotionally validating moment that demonstrated the value of pursuing skill-building without immediate external reward

Episode details: published December 17, 2025 · 13K views · 1:44:53 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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