Growing up in the city of Kolkata in India, a young Chet Kapoor, now the CEO of data and AI company DataStax, would often turn to the pages of A Little Kingdom, a book about the meteoric rise of Steve Jobs and his enterprise Apple, and dream big.
“I was fascinated. I wanted to work for Steve Jobs,” Kapoor tells Fortune—and that’s exactly what he did.
His first order of business was moving from India to the States in 1983 before taking on “a bunch of computer classes” to prime himself for any role in the vicinity of the late Apple founder.
Kapoor accomplished that dream just a few years later when he bagged an internship at NeXT Computer—although he admits he was essentially the intern to the intern.
“I was the guy that got coffee for the guy that made coffee,” he laughs. “It didn’t matter what I did. Janitorial services, dishes—I was 20 yards away from Steve Jobs.”
Pay to work with your hero
Even if Jobs didn’t know who Kapoor was, by his own account, he still thinks that working in the shadows of an esteemed entrepreneur was a formative experience—one he even advises graduates to pay for.
“What I tell college graduates is to find a set of people you want to really work with, convince them that they need you, and then pay them to let you work for them,” he says, insisting the first four years of your career shapes your personality and professional trajectory.
“The experience you will get from working with really smart people will pay you dividends that you cannot imagine,” he says. “It’s not the company you work for, it is the individuals you work with that define you.”
If you’re thinking the advice sounds unaffordable during a cost-of-living crisis (as well as elitist), he argues it’s better value for those who are already spending thousands of dollars on a degree.
“Think about it, right? College graduates have just paid $200,000 in tuition. And I’m talking to them at the end of the senior year saying, that’s actually not a great use of money,” he explains. “Let me tell you how you could have used it: Focus on the people that you work with, because that’ll change your career.”
That being said, Kapoor did go to college himself.
Start your entrepreneurial journey as soon as possible
While others were at frat parties, Kapoor was juggling his education with running his own consulting firm, working in fast food chains, and interning at Jobs’ NeXT.
A skill Kapoor was quick to learn at just 22 years old was how to balance profit and loss.
“It was not a ‘nice to have’ for me, it was important that I made money because that’s how I paid for tuition,” he explains. “So if I didn’t make money, I couldn’t go to school.”
Looking back on his life, Kapoor describes it as a “hand-to-mouth existence” but says that there’s “nothing” like being your own boss to prepare you for leadership.
After graduating, he climbed the ranks quickly from Jobs’ intern to the CEO of Gluecode, an open-source software he sold to IBM in a mere six months, in around 15 years.
“Every individual goes through three different stages in their career. They are individual contributors, they manage people, and then they lead managers,” he shrugs. “So, I believe everyone has to go through that journey.”
But with the average CEO over 50 years old, it’s clear he went through that process at lightning speed. He said he believes it’s down to how you show up in the early years of your career.
“There’s no magic bullet here, you have to lead yourself, then you can lead a small team, and then you lead leaders, right? And I think it all comes down to how you think about leading yourself.”
Kapoor says he concentrated on the team’s success over his own contributions and nailed the execution.
“At the end of the day, belief [in one’s self] is cheap. You can read leadership books, and this and that. But if you don’t lead yourself that way, you will not be able to lead people.”
Don’t prime your business for sale
After orchestrating the sale of Gluecode to IBM for an undisclosed amount, Kapoor became the CEO of the analytics software Apigee in 2007.
Under his helm, the company underwent a successful rebranding; attracted big clients like Netflix, Target, and Walgreens; and raised $87 million through a public IPO before being acquired by Google for $625 million in 2016.
Kapoor has one tip for priming a business for sale: Don’t.
“My take would be to focus on building a business, hiring great people, getting great customers, and then everything else happens around it,” he says.
Even now, he says that his motto is always: “We have an open-for-business sign, not a business-for-sale sign.”
A version of this story originally published on Fortune.com on July 10, 2023.
