In today’s uncertain job market, Gen Z keeps hearing the same advice: don’t plan your entire career now; follow your instincts and trust that the salary and stability will come later.
Kyle Hanslovan is proof that this can work — but not exactly in the way you imagine. Now CEO of Huntress, a cybersecurity company valued at US$3 billion, his path to the top didn’t start with a degree from an elite university or an internship in Silicon Valley. Instead, it all started in AOL chat rooms and internet hacker forums.
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Hanslovan described his younger self as a “suspicious” kid who spent his time pirating video games while living with his single mother in Florida. This self-taught curiosity caught the attention of the U.S. Air Force, which recruited him at age 17 to put his hacking skills into practice — this time, legally.
“When you grow up with very little money, you have to learn and experiment,” Hanslovan told Fortune. “Sometimes you learn by being scolded, and sometimes you learn by succeeding.”
He spent years in offensive cyber operations before moving into the private sector, supporting missions linked to the National Security Agency (NSA). It was there that he began to realize how drastically the threat landscape was changing.
What once seemed like a clever way to bypass corporate firewalls or download a free game had evolved into something much more serious. Hackers began targeting critical infrastructure, hospital systems and small businesses.
This realization led Hanslovan to take a leap. In 2015, he left a stable career to co-found Huntress, a cybersecurity startup focused on protecting small and midsize organizations that large companies often ignore — from small-town accountants to innovative technology startups.
After living on instant noodles and sleeping in his car while growing the company to $3 billion, Hanslovan admits he “wouldn’t do it all over again”
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The cyber threat has only gotten worse in recent years: Americans lost $16.6 billion to internet crime in 2024, a 33% increase from the previous year, according to the FBI’s most recent report.
Ongoing geopolitical tensions and the rapid adoption of AI tools could make attacks even more sophisticated and damaging in the coming years.
For Huntress, this threat was a positive for business: the company grew to more than 700 employees across five countries and reached a $3 billion valuation. But, according to Hanslovan, this has not come without significant sacrifices over the past decade.
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“I slept in my car for a lot of the early days of Huntress; we couldn’t get venture capital,” the 40-year-old executive recalled to Fortune. “I had 60 investors say no, and we had already exhausted all the founders’ money.”
Hanslovan acknowledged that entrepreneurial resilience alone is not unique — many founders have faced rejections from investors or started from scratch, at home. Instead, he believes that turning childhood hardships into passion can be a real advantage.
“I really think that a lot of people who get there had some unusual level of hardship in their childhood that helped them persist through those difficult times,” Hanslovan said. “So, even though it wasn’t the best time of my life, I don’t regret it at all.”
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Still, he would make some changes. When he founded Huntress, his three children were 5, 9 and 11 years old. Today they are 15, 19 and 21; two have already gone to college, and there was a divorce along the way.
“I overworked too much. For the first eight years, I totally believed in this culture of working non-stop,” he said. “I missed a lot of the best years of their lives.”
“I probably wouldn’t do it all over again if I could,” he added.
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Hanslovan’s advice for Gen Z: You don’t have to become Mark Cuban
Despite all the success, Hanslovan also admits that it doesn’t necessarily bring automatic satisfaction.
“All the money, all the glamor and all that didn’t make me happier. If anything, it made me more disconnected,” he said.
Part of this dissatisfaction, he added, came from a mentality he internalized early on: that building a billion-dollar company was the standard for ‘having made it in life’.
“I wish I had known sooner that I would still be successful even if this hadn’t turned into a $3 billion company,” Hanslovan said. “There are many ways to make a difference that don’t just involve money.”
He also advises Generation Z to undertake — but only if they define success on their own terms.
It’s a message that could make sense for a generation that is already heading in that direction. Nearly two-thirds of 18- to 35-year-olds say they have started a side job or plan to, according to a 2024 Intuit survey, and nearly half say their main motivation is simply to be their own boss.
Still, Hanslovan cautioned against aiming too high unnecessarily.
“You don’t need to become [o bilionário] . You don’t need to create a $3 billion Huntress to have a good life and support your family,” said Hanslovan.
“There’s nothing wrong with growing a lifestyle business, a local business of your own or something like that that allows you to fill that gap.”
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