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Reading: Harvey’s 30-year-old CEO says failing is a ‘good way to learn’ and says ‘destroying your ego’ led him to an $11 billion success | Fortune
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Asolica > Blog > Business > Harvey’s 30-year-old CEO says failing is a ‘good way to learn’ and says ‘destroying your ego’ led him to an $11 billion success | Fortune
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Harvey’s 30-year-old CEO says failing is a ‘good way to learn’ and says ‘destroying your ego’ led him to an $11 billion success | Fortune

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Last updated: April 16, 2026 5:39 pm
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3 hours ago
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Harvey’s 30-year-old CEO says failing is a ‘good way to learn’ and says ‘destroying your ego’ led him to an  billion success | Fortune
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How do you construct an $11 billion startup? For Winston Weinberg, CEO and co-founder of AI authorized 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 stated on a current episode of Fortune’s Time period Sheet podcast. 

The 30-year-old founder is a lawyer by coaching. However that each one modified in 2022 when he left his job at a securities and antitrust regulation agency to begin Harvey, a startup that builds AI instruments for legal professionals. Since then, he andGabriel Pereyra, a former Meta and Google DeepMind AI analysis scientist, have earned the backing of the OpenAI Startup Fund, Sequoia Capital, and Kleiner Perkins. 

However that success didn’t come with out loads of failures alongside the way in which. And that, he stated, is what modified his relationship to wins and losses.

“It’s not just you have to have a bunch of wins and then have a lot of failures. But you have to get good at taking some time to actually analyze: What did you do right? What did you do wrong?” Weinberg defined. “Most of that is destroying your ego 24/7.” 

He doesn’t draw back from failing, he stated, including “it’s a very good way to learn.”

His feedback echo a long-held mantra of profitable founders, from Invoice Gates to Mark Cuban: study out of your failures. Weinberg offers with failure by having excessive ambitions, and excessive requirements. Wins and losses maintain much less weight when there’s a long-term aim in thoughts, he defined. He takes this tack together with his workers as effectively. He defined that it may be an adjustment working with him as a result of he’ll name out 15 failures in a day, which may shock some folks as a result of they’re striving for perfection. 

“I do not care about perfection. I care about rate of improvement,” Weinberg stated. “That’s all that matters because otherwise, what you’re going to end up doing is you’re going to hire a bunch of people that are really good for six months, and then if they aren’t improving, then it’s irrelevant, because your business has changed massively.” 

Weinberg stated that Harvey’s workers, together with himself, should “re-earn” their positions each six months to outlive in an business the place if an organization isn’t innovating quick sufficient, it’s going to lose, he defined. Greater than the know-how, Harvey’s decisive tradition is what issues to him most, he stated.   

“I think you have to basically build a company that has a culture of making decisions very quickly and being okay to make mistakes.”

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