30-Year-Old CEO Says Failing and Destroying His Ego Led Him to $11 Billion Success

How do you build an $11 billion startup? For Winston Weinberg, co-founder and CEO of AI legal startup Harvey, it’s all about failure.

“I think it’s really hard to figure this out without failing. You just have to fail a million times,” Weinberg said on a recent episode of Fortune’s Term Sheet podcast.

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The 31-year-old founder has a law degree. But everything changed in 2022, when he left his job at a firm specializing in corporate and antitrust law to create Harvey, a startup that develops AI tools for lawyers.

Since then, he and Gabriel Pereyra, a former AI research scientist at Meta and Google DeepMind, have won support from the OpenAI Startup Fund, Sequoia Capital, and Kleiner Perkins.

But that success didn’t come without many failures along the way. And, according to him, that’s what changed his relationship with victories and defeats.

“It’s not just about having a few wins and then a lot of failures. You also have to get good at taking the time to really analyze: what did you do right? What did you do wrong?” explained Weinberg. “A big part of it is destroying your ego 24/7.”

He doesn’t shy away from failure and adds: “It’s a really good way to learn.”

His comments echo a long-standing mantra among successful founders, from Bill Gates to Mark Cuban: learn from your failures. Weinberg deals with failure by maintaining high ambitions and standards.

Wins and losses carry less weight when there is a long-term goal in mind, he explained. He also applies this approach to his team.

According to Weinberg, working with him can require adaptation, because he tends to point out up to 15 flaws in a single day — which may surprise some people who seek perfection.

“I don’t care about perfection. I care about speed of improvement,” Weinberg said.

“That’s all that matters, because otherwise you’re going to end up hiring a bunch of people who are really good for six months, and if they’re not improving, it becomes irrelevant because your business has changed massively.”

Weinberg said Harvey staff, including himself, need to “re-earn” their positions every six months to survive in an industry where, if a company doesn’t innovate fast enough, it loses.

More than technology, Harvey’s decisive culture is what matters most to him.

“I think you basically need to build a company with a culture of making decisions very quickly and being comfortable with making mistakes.”