Breakfast News: 4 CEOs Playing the Long Game

SEPTEMBER 12, 2026

What separates a capable CEO from a great one? It’s not just vision or great timing. When you look closely at the architects of some of the biggest businesses, distinct patterns of greatness begin to emerge. Four Fools — two from Team Rule Breakers, two from Team Hidden Gems — each named one CEO they believe best exemplifies this rare tier of leadership.

None of these CEOs shares the same playbook. Yet, beneath their varying styles, all share something in common: ruthless execution, fanatic focus on moats, and the conviction to make big, contrarian bets.

Value in the Cloud(flare)

By Jason Moser
Team Rule Breakers

Cloudflare (NYSE: NET) co-founder and CEO Matthew Prince is not one to keep his opinions to himself. He is often seen as a polarizing figure in the tech world. I see him as a passionate leader who believes deeply in Cloudflare’s potential.

Here’s a fun fact: Prince wrote his first computer program at the ripe old age of seven! So, to say tech is in his blood would be an understatement. That early spark eventually led to 2009, when Prince teamed up with colleagues Michelle Zatlyn and Lee Holloway to found Cloudflare with the mission “to help build a better internet.”

One thing that stands out is Prince’s forward-thinking and competitive drive. He reminds me a lot of Jeff Bezos, as he’s equally relentless in his pursuit of the company’s mission.

Prince owns 75% of the company’s class B shares, giving him 39% total voting power. We Fools love to see leaders with skin in the game. It doesn’t mean an investment will always work out, but it signals leadership’s incentive to steer the business in the right direction. So far, it’s working out well for long-term owners of the stock; shares are up over 1,500% since its IPO in September 2019.

Adaptability Is Core to Greatness

By Tim Beyers
Team Rule Breakers

Adaptability is necessary for longevity, and a long, effective tenure is essential for greatness. Ted Sarandos has helped create many millionaires in his 26 years at Netflix (NASDAQ: NFLX).

He spent the first 20 years leading Netflix’s content operations, and he’s been co-CEO for the last six years. Four major strategic shifts have defined Netflix under Sarandos:

1. From bulk DVD by mail to streaming licensed content.
2. From streaming licensed content to producing original content, ushering in “binge watching” in the process.
3. From a regional U.S. streamer to a global provider with content in local languages.
4. From subscription-only to on-demand streaming subscription plus ads, including live events.

Netflix has faced dire competitive threats at every stage of its life. Sarandos has been around for most of them, and he’s on the hook again now.

Competition for attention has never been greater. It’s possible we’ll see another Sarandos-led Netflix pivot in light of this. If so, it would be fitting.

Ted Sarandos has adapted faster and more frequently than most of his peers in the entertainment industry when under threat. That’s what makes him great, and I expect him to prove it again.

A Steady Hand in Any Market

By Lou Whiteman
Team Hidden Gems

Michael Kehoe left a stable job as CEO of James River Insurance (a predecessor of James River Group (NASDAQ: JRVR)) because he saw an opportunity to use technology to reboot the insurance industry. He traded near-term stability for start-up chaos, betting that his conviction would pay off in the long term. It is a mindset that continues to guide Kinsale Capital Group (NYSE: KNSL) 17 years after its founding.

The numbers speak for themselves: Kinsale shares are up 1,870% since its 2016 IPO. (For the record, James River is down 88% during that time.) Kehoe built Kinsale by moving at his own pace, not the pace demanded from an established incumbent, and by thinking in terms of decades instead of quarters.

The mindset continues to this day. Kinsale is down 20% over the last year. A period of rising rates and few hurricanes or other natural disasters has led to a flood of insurer interest in Kinsale’s niche. Kehoe has refused to fight pricing battles, and as a result, new business has slowed.

As a shareholder, I hate to see my stock underperform. But I believe Kehoe’s strategy will pay off in the long term, and I have nearly two decades of results to back up that belief. No one plays the long game better than Mike Kehoe.

The Visionary Architect

By Rachel Warren
Team Hidden Gems

When discussing leaders who prioritize decades over quarters, Jensen Huang of Nvidia (NASDAQ: NVDA) stands in a league of his own.

For years, he directed resources toward accelerated computing and AI architecture long before the rest of the world realized its potential. This was not a gamble on a trend but a fundamental belief in the future of computing. He has successfully navigated market cycles by focusing on a singular, massive vision.

Huang’s mastery of the long game is evident in how he builds ecosystems rather than just products. By creating a software layer that developers rely on, he has built a moat that’s incredibly difficult to cross.

Foolish Final Thoughts

Did you notice a pattern? Four leaders, one phrase circled again and again: decades over quarters. Three founded the companies they run; the fourth has spent 26 years at his. Each placed a bet long before the payoff arrived, then held it while the doubters got loud.

Which CEO would you add to this great lineup, and what’s their claim to greatness?

Debate with friends and family, or become a member to hear what your fellow Fools are saying!

Jason Moser has positions in Cloudflare. Lou Whiteman has positions in Cloudflare and Kinsale Capital Group. Rachel Warren has no position in any of the stocks mentioned. Tim Beyers has positions in Netflix. The Motley Fool has positions in and recommends Cloudflare, Kinsale Capital Group, Netflix, and Nvidia. The Motley Fool has a disclosure policy.