Harvey CEO Winston Weinberg says he does his best work when he's stressed out about the next day

• Harvey CEO Winston Weinberg said he does his best work during weeks when he goes to bed stressed.
• He said the times when his startup has stagnated are "every day I don't have something that's really stressful."
• Keith Rabois, a managing director at Khosla Ventures, has long advocated for the benefits of stress.

Harvey CEO Winston Weinberg wants to be under pressure.

Weinberg said that he's realized he does his best work when he goes to sleep, dreading just how busy he'll be the next day.

"The weeks that I do the best work or feel like I did the best work is every single night before I go to bed, I'm like, 'Ah, shit,'" Weinberg told investor Harry Stebbings during a recent episode of Stebbings' "20VC" podcast.

Harvey is one of the hottest names in the closely-watched legal AI startup space. In December, Weinberg's firm said it had reached an $8 billion valuation.

Weinberg said he had heard PayPal mafia member Keith Rabois, managing director at Khosla Ventures, discuss his views on stress. While they have never met, Weinberg said he strongly agrees with Rabois' belief in the power of stress.

"I think the times that I've stagnated, or the company has stagnated, is every day I don't have something that's really stressful," Weinberg said.

Weinberg said that he wants his employees to "resist complacency," which he called "the enemy of any startup."

"At Harvey, we have a value called Job's Not Finished and it's essentially just always holding yourself to a higher standard and believing we have an obligation to improve. I believe in progressive stress," Weinberg said in a statement to Business Insider. "If you consistently seek out the highest amount of stress it makes you better at the fastest rate possible, what stresses you out the first time doesn't stress you out as much the second so you have to keep raising the bar."

Harvey doesn't want its workers to be "stressed out 24/7," Weinberg said.

"It does mean that I think startups reward people who can rapidly adjust and calibrate to change," he said.

Stress is highly valued in Silicon Valley

Rabois has repeatedly professed that properly managed stress is the key to "health, wealth, and happiness," as he put it in 2024. Rabois is a huge fan of Stanford lecturer Kelly McGonigal's book, "The Upside of Stress: Why Stress Is Good for You, and How to Get Good at It."

"It confirms what I've always believed," Rabois told Stebbings in 2017 when he described why he loves McGonigal's book, "that stress is actually a great thing for people, that taking on more difficult challenges makes you more successful, makes you happier, and ironically, it makes you healthier."

Nvidia CEO Jensen Huang has said that he's in a constant "state of anxiety."

"I have a greater drive from not wanting to fail than the drive of wanting to succeed," Huang told Joe Rogan in December.

Snap CEO Evan Spiegel said he has tried to reframe how he views stress.

"How do we approach stress in our minds?" Spiegel said on the "Grit" podcast in December. "Do we call it out as stress and something that's bad, or do we say, 'Actually, this is a gift, this is a learning opportunity, this is a growth opportunity.'"

Mike Steib, now the CEO of Tegna, previously told Business Insider that it is all about striking the right balance.

"There is an optimal point — you feel urgency. You're working on something important, but it's not freaking you out," Steib said in 2017.