Oracle founder Larry Ellison has an interesting take on what it takes to build generational companies.
The billionaire tech mogul, who recently briefly became the world’s richest man following a surge in Oracle’s stock price, offers unconventional wisdom about entrepreneurship that challenges the typical startup playbook. His perspective comes from decades of experience building one of the world’s largest enterprise software companies, and his advice cuts straight to the heart of what separates successful entrepreneurs from the pack.
According to Ellison, the path to entrepreneurial success requires a contrarian mindset. “My standard advice to entrepreneurs is you can’t be successful as a small company at doing the same thing everyone else is doing,” he explains. “So if you’re an entrepreneur, you have to find errors in conventional wisdom. You have to find where everyone says… when you tell them your idea, most people say you’re crazy.”
This reality check is something every entrepreneur faces, Ellison suggests. “When you hear that — ‘No one’s doing that. You must be crazy’ — there are two possibilities,” he continues with characteristic directness.
“One is you’re first with a really good idea. Unfortunately, the other is you’re crazy.”
The implications of Ellison’s philosophy extend far beyond startup advice. His framework suggests that true innovation requires entrepreneurs to operate in the uncomfortable space between genius and delusion — a place where conventional wisdom fails and breakthrough opportunities emerge. This approach has proven remarkably prescient in the tech industry, where many of today’s most valuable companies were initially dismissed as impractical or impossible.
Consider the parallels with other transformative companies: Amazon faced skepticism about selling books online when physical bookstores dominated retail. Tesla challenged the automotive industry’s assumption that electric vehicles couldn’t be commercially viable. Even Oracle itself disrupted the database market by betting on relational databases when established players were focused on different architectures.
Ellison’s recent ascent to briefly becoming the world’s richest person — driven by Oracle’s strong performance in cloud computing and AI infrastructure — validates his own contrarian bet. While competitors focused on consumer-facing technologies, Oracle doubled down on enterprise solutions and cloud infrastructure, positioning itself as a critical backbone for the AI revolution. This strategic positioning, once questioned by analysts, now appears prescient as demand for enterprise AI capabilities explodes across industries.
The challenge for entrepreneurs, as Ellison frames it, is developing the judgment to distinguish between revolutionary ideas that seem crazy and ideas that actually are crazy. This discernment often separates successful founders from those who remain stuck chasing obvious opportunities in crowded markets. In an era where technological disruption continues to accelerate, Ellison’s advice serves as both inspiration and warning: the biggest opportunities may well be hiding in plain sight, disguised as ideas that everyone else thinks are impossible.