As workers deal with layoffs, AI disruption, and constant pressure to prove themselves, insecurity can feel like an inevitable part of building a career. But for Aravind Srinivas, CEO of AI giant Perplexity, operating under the fear of failure only gets in the way of success. He earned his place in the trillion-dollar technology race by focusing on the thrill of winning.
“I have nothing to lose,” Srinivas said recently on the 20VC with Harry Stebbings podcast. “I came from nothing. I never imagined I would be doing all this. So my life has already been extraordinary beyond any level of imagination.”
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In 2022, he co-founded Perplexity, which has since raised at least $1.5 billion in total funding. Its market value was estimated at around US$18 billion to US$20 billion in 2025.
But growing up in Chennai, India, in a lower-middle-class family, he said simply getting a job was the standard of success.
And the AI prodigy excelled in every measurable aspect, earning a bachelor’s degree specializing in electrical engineering from the prestigious Indian Institute of Technology (IIT).
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The year after graduation, Srinivas landed a research internship at OpenAI and then Google DeepMind — his family’s most desired job. Therefore, any additional achievement is just a bonus in a career that you already consider extraordinary.
“All we wanted was to get a job at Google. Being an engineer at Google was considered a victory,” continued the CEO. “I’m already doing exceptionally well compared to the ambition we had as a family, so I really have nothing to lose.”
“So whenever I try to act like someone who is trying to avoid failure, who is playing defense, I remind myself that this is the stupidest thing to do,” Srinivas said. “It’s better to go all in and do your best. Always play attacking. Attack, attack, attack.”
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Ryan Smith, former CEO and founder of cloud software platform Qualtrics, agrees that pushing boundaries is critical to achieving success. In fact, he regrets times when he didn’t follow his own advice.
If all of a company’s hires, products, and acquisitions are “safe,” it’s clear that nothing revolutionary is on the horizon. Smith says taking calculated risks to stay ahead of the curve is essential.
“My biggest fear as a CEO is that people will stop pushing boundaries,” Smith wrote for Fortune magazine in 2016. “Some of my biggest regrets have happened when I had a great idea and didn’t act on it fast enough or didn’t follow through because I was afraid of failure.”
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Even being placed in difficult, highly competitive work environments can present a huge opportunity for growth.
Amit Walia, CEO of software company Informatica, said being constantly challenged early in his career prepared him to lead a business valued at US$7.6 billion.
Walia spent almost five years at consultancy McKinsey & Company as a senior project manager and now sees that period as intense and intimidating. Still, he says the experience was extremely rewarding for developing his skills as a technology leader.
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“You really are put in difficult situations [na McKinsey]… You always have to maintain a very analytical mindset, capable of identifying the essence of the problem,” Walia told Fortune earlier this year. “You become a better person by living in an environment surrounded by many other intelligent people.”
Joanna Griffiths, CEO of the $400 million lingerie company Knix, even worked with a hypnotherapist to help “rewire” her brain — especially around her fear of failure. In fortnightly one-hour sessions, Griffiths has been learning to make smarter decisions “from a stance of optimism rather than fear.”
“We make a big deal out of the fear of failure,” Griffiths told Fortune earlier this year. “Often we don’t allow ourselves to think through and say, ‘Okay, if this really goes wrong, what’s the worst that’s going to happen? Do I still have my family? Do I still have my health? Do I still have the knowledge that I’ve accumulated?'”
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