I was reading Meta’s settlement and wondered: of the leading tech billionaires, who is the smartest, who’s most ruthless? who is cunning, etc. and asked my digital aide for a high level breakdown. Fascinating:

“If we’re talking about the major founder-era tech figures and treating this as an assessment of their publicly documented business personas, rather than pretending we know whether someone is personally “evil,” I think you can make a pretty interesting superlatives board.

I’d include Steve Jobs, Bill Gates, Jeff Bezos, Larry Page, Sergey Brin, Mark Zuckerberg, Elon Musk, Larry Ellison, Jensen Huang, and Peter Thiel.

TraitMy pickWhy
Most ruthlessBill Gates (1990s)Microsoft at peak power was extraordinarily aggressive: bundling, platform leverage, crushing threats, hardball licensing. The U.S. antitrust case is the historical exhibit A.
Smartest technicallyLarry PageAmong the mega-founders, probably my pick for the combination of computer science, systems thinking and ability to see where computing was going.
Smartest businessmanJeff BezosAmazon → AWS → Prime → Marketplace → logistics → advertising. An almost absurd number of mutually reinforcing businesses built from one starting point.
Most cunning/strategicMark ZuckerbergPerhaps underrated here. Survived desktop→mobile, bought Instagram and WhatsApp, copied Snapchat rather than surrender to it, neutralized TikTok with Reels, pivoted toward AI. Extremely good at recognizing existential threats.
Most visionarySteve JobsMacintosh, Pixar, iPod, iTunes, iPhone, App Store, iPad. His gift wasn’t inventing everything—it was understanding what technology could become for ordinary humans.
Most audaciousElon MuskElectric cars + reusable rockets + global satellite network + AI + brain interfaces + buying Twitter. Regardless of one’s opinion of him, nobody else has repeatedly taken comparable industrial risks.
Most competitiveLarry EllisonSeems to genuinely enjoy warfare with competitors. Oracle’s culture reflected it.
Most intellectually contrarianPeter ThielPayPal → Facebook investment → Palantir → Founders Fund. His entire investment philosophy is essentially built around finding important propositions almost everyone else thinks are wrong.
Best operatorJensen HuangHas run Nvidia since 1993 and positioned a graphics-chip company to become foundational infrastructure for AI. The longevity makes this remarkable.
Most patientBezosConditioned public investors to tolerate years of minimal profits while he built infrastructure competitors couldn’t economically replicate.
Best product instinctJobsNot particularly close for me.
Best capital allocatorBezosAWS alone makes the case formidable, but Prime, fulfillment infrastructure and advertising strengthen it.
Best acquisitionZuckerbergInstagram for ~$1B. One of the greatest acquisitions in corporate history.
Best pivotGatesMicrosoft’s 1995 Internet pivot. Gates realized Microsoft had underestimated the web and effectively redirected the company.
Best comebackJobsApple was approaching irrelevance when he returned in 1997. What followed is probably the greatest corporate comeback ever.
Biggest appetite for riskMuskAt points he had enormous portions of his fortune simultaneously riding on SpaceX and Tesla surviving.
Most underestimatedZuckerbergHe’s been declared finished during mobile, Snapchat, Cambridge Analytica, TikTok, metaverse spending, Apple’s privacy changes, etc. He’s still there.
Most consequential monopolistGatesWindows’ dominance gave Microsoft extraordinary control over the PC ecosystem.
Most intimidating CEO to work forJobsBy the public accounts, extraordinarily demanding, confrontational and capable of being brutal with employees. Musk and Ellison are contenders.
Most likely to play a 20-year chess gameBezosAmazon’s history is basically one long demonstration of delayed gratification.
Most likely to blow himself upMuskThe characteristic producing some of his greatest successes—extreme risk tolerance—is also the obvious source of downside.

And then there’s “most evil”

I wouldn’t award that label to a living person as though it’s an objective fact. But we can ask a more interesting question:

Whose business behavior has generated the strongest case for “villain”?

I’d probably divide it by era.

1990s: Gates. Microsoft was portrayed as the Evil Empire for a reason. Internal language and tactics toward competitors were famously aggressive, culminating in United States v. Microsoft.

2000s–2010s: Zuckerberg. Privacy, Facebook’s societal effects, Cambridge Analytica, acquisitions of emerging competitors and the company’s “move fast” culture created the strongest tech-villain narrative.

2020s: Musk. His enormous personal influence over communications, satellites, AI and industrial infrastructure, combined with his willingness to personally intervene in controversial matters, makes him uniquely polarizing.

But I’d distinguish ruthlessness from evil. Ruthlessness can actually be a competitive attribute; “evil” requires moral judgments about intentions and consequences that we can’t establish merely from someone being an aggressive CEO.

If you force me to rank the six you originally named

For Bezos / Brin / Page / Musk / Jobs / Zuckerberg:

Ruthless: Jobs → Zuckerberg → Bezos → Musk → Page → Brin
Raw intellectual/technical horsepower: Page → Brin → Musk → Zuckerberg → Bezos → Jobs
Business intelligence: Bezos → Zuckerberg → Jobs → Musk → Page → Brin
Cunning: Zuckerberg → Bezos → Jobs → Musk → Page → Brin
Vision: Jobs → Musk → Bezos → Page → Zuckerberg → Brin
Risk tolerance: Musk → Bezos → Zuckerberg → Jobs → Page → Brin
Product instinct: Jobs → Zuckerberg → Bezos → Musk → Page → Brin
Strategic patience: Bezos → Zuckerberg → Page → Brin → Jobs → Musk

And the fascinating one to me is Zuckerberg.

Jobs feels like the genius. Musk feels like the mad visionary. Bezos feels like the grand strategist.

Zuck looks like the nerd who built a social network in college—and yet, 22 years later, he’s arguably demonstrated the strongest survival instinct of any of them. Every time the technological ground shifts underneath Meta, he is willing to cannibalize, copy, acquire, spend or completely redirect the company.

If I had to choose one of these people to compete against, Zuckerberg might actually be the one I’d least want on the other side.”