$ cat ./records/gates-calls-losing-mobile-to-android-his-greatest-mistake-a-400-b-2019.txt
Gates Calls Losing Mobile to Android His 'Greatest Mistake,' a $400 Billion Miss
[RECORD.TXT] · cat --full
In a 2019 talk, Bill Gates candidly called Microsoft's failure to win the smartphone market his 'greatest mistake ever,' estimating it had cost the company on the order of $400 billion. 'The greatest mistake ever is whatever mismanagement I engaged in that caused Microsoft not to be what Android is,' he said, calling a dominant non-Apple phone platform 'a natural thing for Microsoft to win' that it lost partly through his own missteps and the distraction of its antitrust battles. The remark was a rare, blunt self-assessment of his biggest business failure.
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Related Accomplishments
2026
Gates Foundation Trust Sells Off the Last of Its Microsoft Stock
In the first quarter of 2026, the Bill & Melinda Gates Foundation Trust sold its remaining Microsoft shares, fully exiting a position in the very company that created Gates's fortune — capping a long, deliberate diversification away from the stock. The endowment that funds Gates's philanthropy, managed separately from its grant-making through Cascade, is now anchored instead by Berkshire Hathaway, Waste Management, railroads, and heavy-equipment makers. The sale underscored how thoroughly Gates's giving had decoupled from Microsoft's day-to-day fortunes.
2026
Gates's Charitable Endowment Is Now Led by Berkshire, Not Microsoft
By 2026, the publicly disclosed stock portfolio of the Bill & Melinda Gates Foundation Trust — the endowment that funds Gates's philanthropy — was led not by Microsoft but by Berkshire Hathaway, Waste Management, Canadian National Railway, Caterpillar, and Deere. Decades of diversification, plus Warren Buffett's stock gifts, left it concentrated in railroads, waste, heavy equipment, and Buffett's conglomerate, while Microsoft — the source of the original fortune — had largely been sold down. The unglamorous, value-oriented mix reflects the long stewardship of Gates's money manager, Michael Larson, through Cascade Investment.
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