Investing | My Worst & Best Investments | My First Million Podcast

About this video

Shaan shares three personal investment stories: missing a $25,000 angel investment in a billion-dollar international student application SaaS company, losing money on an ill-conceived MGM put option trade during COVID, and successfully betting on Bitcoin. The hosts discuss why short-term stock market movements feel disconnected from business fundamentals, introducing Keynes’s beauty contest metaphor to explain speculative markets.

Key takeaways

• Shaan passed on an early investment opportunity that would have returned over $5 million due to risk-aversion and insufficient capital allocation strategy, illustrating how founders sometimes avoid bets they intellectually believed in
• The short-term stock market is driven by speculation and perception rather than business fundamentals—a ‘beauty contest’ where investors bet on what others will think rather than on actual company value
• Over long time horizons, markets function as a ‘weighing machine’ where fundamental business performance matters, but in the short term they reward popularity and hype, making speculation frustrating and unpredictable

Episode details: published May 15, 2020 · 1.9K views · 9:44 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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