Chit Chat Stocks Bill Miller: The Bitcoin and Amazon Billionaire
Jan 28, 2026
A lively dissection of Bill Miller's career through four case studies. They dig into why Dell's cash dynamics mattered, how big bets on financials went wrong in the crisis, and what made Amazon a comeback engine. They also explore Miller's probabilistic take on Bitcoin and how his factor-mixing approach shaped later portfolios.
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15-Year Winning Streak
- Bill Miller rose to run the Legg Mason Value Trust and beat the S&P 500 for 15 consecutive years from 1991 to 2005. He used contrarian, concentrated bets and attracted tens of billions in AUM at his peak.
Dell's Negative Working Capital Win
- Miller bought Dell in 1996 at about 5x earnings and benefited from its negative working capital model. The position became roughly a 50-bagger in under five years for his fund.
Negative Working Capital Fuels Growth
- Negative working capital can fuel growth without outside capital because customers fund the business. Miller used this trait to see through weak GAAP and capture long-term cash generation.
