Rainmakers #23 Henry Hillman: The Original LP
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Sep 26, 2025 Dive into the fascinating world of Henry Hillman, who transformed his family’s coal and steel empire into a legacy of impactful investments. Discover his clever strategies, like buying distressed assets and leveraging minority stakes to gain influence. Hillman's preference for smaller companies opened doors to promising talent. Explore his early backing of giants like KKR and Kleiner Perkins. With a keen eye for timing, he built a massive real estate portfolio, proving that sometimes, the biggest risks lead to the greatest rewards.
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Buying Distressed Assets In Downturns
- Hart Hillman bought distressed coal and related assets in downturns and ran them lean to profit when cycles turned.
- He expanded via opportunistic deals and low leverage to build one of the largest coal operators by the 1930s.
From Small Stakes To Control
- Hart used minority positions, board seats, and mergers to convert small stakes into near-control of large steel companies.
- He repeated the same playbook buying small banks and packaging them into Pittsburgh National Bank.
Dismantling The Family Empire
- After Hart died, Henry Hillman sold off most of the family empire within a decade to recycle capital into higher-return opportunities.
- He dissolved minority interests and kept only Pittsburgh Coke while shifting toward investing rather than operating.
