In Silicon Valley’s current culture of extreme performance, Winston Weinberg, CEO of AI legal unicorn Harvey, has come to the forefront. He believes that high stress is crucial to successful startup life. 

In a recent interview with the 20VC podcast, Weinberg described his best weeks as the ones where he goes to bed dreading how much he has to do the next day. He argues that “progressive stress” is the fastest way to grow as a founder. 

“You should be constantly stressed and do things that make you stressed every day,” Weinberg said on the podcast. “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.”

That viewpoint has translated into real business outcomes. Weinberg co-founded Harvey in 2022, and the startup has since emerged as one of the leading companies in the legal AI space. It automates tasks like legal research, document drafting and contract analysis. Harvey has a valuation of around $8 billion and claims more than 1,000 clients across law firms and corporate legal departments. It reached $100 million in annual recurring revenue in August. 

Weinberg’s view is that complacency is the real enemy, not stress. Internally, Harvey codified this principle into a value called “Job’s Not Finished,” which frames constant improvement and raising the bar as an obligation. Weinberg says that if you consistently seek out the highest amount of stress, what once felt overwhelming becomes normal, forcing you to keep elevating the challenges you take on.  

On the 20VC podcast, Weinberg connects this mindset to his personal routines. He describes getting up early, “destroying” himself with a hard run and using that intense physical challenge to soak up stress so that the rest of the day feels more manageable. “If you start your day off with something that is very challenging in a physical way, you have this stress relief through the rest of your day,” he said. “Your body has absorbed that stress.” 

For Weinberg, company-building is mostly about making very good decisions under pressure. He believes that deliberately training stress tolerance, by deliberately taking on stressful things and adhering to strict routines, is a competitive advantage.

“I try to do a stressful thing every week because I [want to build] stress tolerance over time,” he said. 

While Weinberg touts the benefits of stress, another high-profile founder has spoken about how it can be debilitating. Jensen Huang, the co-founder and CEO of AI chipmaker Nvidia, said last month on The Joe Rogan Experience podcast that he works seven days a week in a constant “state of anxiety” driven by fear that the company will go bankrupt — even though Nvidia is the most valuable company in the world.

“It’s exhausting,” Huang admitted on the podcast. “Always in a state of anxiety.”

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