Carl Icahn

Icahn buys undervalued companies with bad management. His thesis is consistently the same: there is enormous value being destroyed by entrenched executives who are more interested in keeping their jobs than returning value to shareholders.

He buys enough stock to force a confrontation. Sometimes management cleans itself up just from the threat of his involvement.

Sometimes he installs new people. Sometimes he forces a full sale of the company.

His version of value investing is more aggressive than Graham''s or Buffett''s. He doesn''t wait for the market to recognise value.

He forces the recognition. He is comfortable with conflict in a way most investors are not.

He sees confrontation with management as part of the job — not an unfortunate side effect of it.

Bill Gates

Gates invests through Cascade Investment LLC in established, cash-generative businesses — railroads, waste management, agricultural equipment, farmland. His biggest single Cascade holding for years was Canadian National Railway.

He has sold most of his Microsoft stock over time. His investment philosophy outside Microsoft mirrors Buffett's: durable businesses with pricing power, bought at reasonable prices.

Carl Icahn

He genuinely believes management teams destroy shareholder value through complacency, self-dealing, and entrenchment. He sees himself as a corrective force — not a vulture, but a mechanism by which markets hold management accountable.

Whether that''s how it looks from inside the companies he targets is a different question. His rules: buy when nobody else wants it, apply pressure to unlock the value, sell when the value is recognised.

Don''t get sentimental about positions. Don''t let management tell you the company is more complex than it looks.

Bill Gates

His core framework: read obsessively, think long-term, and separate emotion from analysis. He takes annual Think Weeks — solo retreats to a lake cottage in the Pacific Northwest where he reads papers and books for two weeks with no interruptions.

He publishes a reading list twice a year at gatesnotes.com. He has said that the best investment he ever made was paying $100,000 to take Warren Buffett to dinner every year.

Carl Icahn

He concentrates. He uses leverage.

He''s comfortable with positions that make other investors deeply uncomfortable. He''s also comfortable being wrong in public — he''s had positions go spectacularly badly and he doesn''t hide from them.

His Hertz position went bankrupt during COVID. His Herbalife long was a very public, very watched position on the opposite side of Bill Ackman''s short.

He doesn''t bluff. When he says he''s going to fight, he fights.

Bill Gates

Gates's risk tolerance is intellectual and deliberate rather than impulsive. He takes genuinely large bets — TerraPower on nuclear fission, billions into climate technology, the Gates Foundation's campaigns to eradicate diseases that kill millions — but only after intense research.

His Think Weeks exist to force slow, rigorous thinking on big decisions. At Microsoft, he kept enough cash on hand to run the company for a full year with zero revenue because he never wanted short-term survival pressure to force a bad long-term decision.

That discipline carries into his personal finances.

Carl Icahn

He lives in Sunny Isles Beach, Florida. He works ferociously hard and has done so into his late 80s.

He''s a hands-on manager — not someone who delegates. He famously said: "If you want a friend on Wall Street, get a dog." He has a Maltese named Tiger.

He''s been a prolific poker player and was once considered one of the best amateur players in New York. He remarried in 2012; his current wife is Gail Golden.

He''s given some money to charity but not at the scale of Buffett or Gates — he''s made no secret of prioritising returns over philanthropy.

Bill Gates

He wakes up early, exercises on a treadmill while watching documentaries, and reportedly does the dishes every night. He has said dishes are meditative.

For a man worth $130 billion, the emphasis on routine is either deeply grounded or very good PR. He drove himself to work at Microsoft for years and lived in a normal house long after he could afford otherwise.

Carl Icahn

Apple. In 2013 he disclosed a $1.5 billion stake in Apple and published an open letter to Tim Cook urging a larger share buyback.

Apple eventually announced a significantly expanded buyback program. The stock rose.

Icahn made approximately $2 billion on the position. He didn''t have to engineer a hostile takeover — just making his involvement public was enough to move one of the largest companies in the world.

Bill Gates

Microsoft Windows. The decision to license MS-DOS to IBM for the PC while retaining the right to sell it to other manufacturers was arguably the most lucrative business decision in tech history.

Every PC manufacturer then licensed Windows. Gates captured the entire PC market without building the hardware.

By 1999, Microsoft's market cap hit $616 billion.

Carl Icahn

TWA. He took over Trans World Airlines in 1985 using a leveraged buyout, extracted cash from the company to pay back the acquisition debt, and sold the valuable London routes to American Airlines for $445 million.

By the time he was done, TWA was a financially gutted airline. It went bankrupt in 1992, again in 1995, and was absorbed by American Airlines in 2001.

Icahn personally made hundreds of millions. The airline''s employees and creditors did not.

He''s defended his actions as legal. Legal and good for everyone are not always the same thing.

Bill Gates

Missing the internet. Microsoft was late and initially dismissive of the internet as a platform.

Gates eventually course-corrected and wrote the Internet Tidal Wave memo in 1995, redirecting the entire company toward internet strategy. But the delay allowed Netscape to establish footholds, and Microsoft's browser monopoly tactics led to the landmark antitrust case United States v.

Microsoft in 2000, which threatened to break up the company.

Carl Icahn

Carl Icahn grew up in Far Rockaway, Queens. His father was a failed opera singer who became a synagogue cantor.

Icahn studied philosophy at Princeton — graduated 1957 — then enrolled in NYU School of Medicine before dropping out after two years to join the army. He became a stockbroker at Dreyfus & Co.

in 1961, saved $400,000, and bought a seat on the New York Stock Exchange in 1968.

He spent the early years running option arbitrage — finding and exploiting small mispricings. He was very good at it.

In the late 1970s he pivoted to a bigger game: buying large stakes in undervalued companies and forcing management changes. His first major target was Tappan Company in 1979.

By the mid-1980s he was feared by corporate boards across America. Oliver Stone''s Gordon Gekko in Wall Street is directly based on the era Icahn created.

Bill Gates

Bill Gates was born in Seattle in 1955. He taught himself to program on a PDP-10 at age 13.

He enrolled at Harvard in 1973, dropped out in 1975, and moved to Albuquerque with Paul Allen to found Microsoft. Their break came when they licensed an operating system to IBM for the original PC — and crucially, retained the rights to sell it to anyone else.

That decision made Microsoft. Windows became the standard operating system for the world.

Gates became the world's richest person in 1995 and held that title for much of the next 15 years. He transitioned out of Microsoft's day-to-day around 2000 and fully moved into philanthropy via the Gates Foundation.

Carl Icahn

Icahn Enterprises is his publicly traded holding company. He''s been chairman since 1987.

Some of his most famous investments: TWA, which he took over in 1985, stripped its most valuable routes to pay back the debt used to acquire it, and left financially hollowed out — it went bankrupt twice after his tenure. Texaco, where he forced a settlement that paid shareholders.

Apple, where he took a $1.5 billion position in 2013 and published an open letter to Tim Cook demanding a larger share buyback. Apple eventually expanded the buyback.

The stock rose. Icahn made roughly $2 billion on the position without engineering a hostile takeover — the threat of his involvement was enough to move a $500 billion company.

He''s also had notable losses. Hertz went bankrupt during COVID while he held a large position.

He lost hundreds of millions.

Bill Gates

Microsoft (co-founder, former CEO and chairman). Cascade Investment LLC (his personal investment vehicle).

Bill & Melinda Gates Foundation (co-chair). Major holdings through Cascade include Canadian National Railway, Deere & Company, and significant farmland.

Early Microsoft equity remains a massive portion of his net worth.

Carl Icahn

Princeton University, BA in Philosophy, 1957. NYU School of Medicine, dropped out after two years.

He''s credited Princeton''s philosophy training with teaching him to question conventional wisdom — which shows up directly in how he argues with corporate boards.

Bill Gates

Harvard University — studied mathematics and computer science. Dropped out in 1975 after his sophomore year to found Microsoft.