30-Year-Old CEO Built $11B Startup by Embracing Failure

A 30-year-old lawyer just proved that failing a million times might be the secret ingredient to building an $11 billion company.

Winston Weinberg left his comfortable law firm job in 2022 to launch Harvey, an AI startup that builds tools for lawyers. Today, the company has backing from OpenAI, Sequoia Capital, and Kleiner Perkins, with a valuation that would make most founders' heads spin.

But Weinberg's path to success looks nothing like the polished LinkedIn stories we're used to reading. Instead of hiding mistakes, he hunts for them relentlessly.

"I think it's really hard to figure this out without failing. You just have to fail a million times," Weinberg shared on Fortune's Term Sheet podcast. His co-founder Gabriel Pereyra, a former Meta and Google DeepMind researcher, joined him on this failure-friendly journey.

The young CEO points out 15 failures to his team every single day. New employees often find this jarring because they're striving for perfection, but Weinberg has different priorities.

"I do not care about perfection. I care about rate of improvement," he explained. In an industry moving at breakneck speed, yesterday's perfection becomes tomorrow's obsolete.

This philosophy extends beyond just accepting mistakes. Weinberg believes in "destroying your ego 24/7" to truly learn from what goes wrong. He takes time after each failure to analyze what worked and what didn't, treating setbacks as data points rather than defeats.

Why This Inspires

Weinberg's approach flips the traditional success narrative on its head. Instead of waiting until everything is perfect, he celebrates rapid iteration and continuous learning. His team has to "re-earn" their positions every six months, not as punishment but as a natural response to how fast their industry evolves.

The culture he's built prioritizes quick decision-making over endless deliberation. Making mistakes isn't just tolerated at Harvey. It's expected, analyzed, and transformed into fuel for growth.

His message resonates beyond the startup world. Whether you're launching a company, changing careers, or learning a new skill, the willingness to fail repeatedly while maintaining high standards creates a powerful engine for improvement.

Weinberg joins a chorus of successful founders from Bill Gates to Mark Cuban who credit failure as their greatest teacher. But he takes it further by building an entire company culture around this principle, proving that embracing imperfection might be the most perfect strategy of all.