In today’s uncertain job market, Gen Z keeps hearing the same advice: don’t map out your whole career now, just follow your instincts and trust that salary and stability will follow.
Kyle Hanslovan is proof that can actually work—just not in the way one might expect. Now the CEO of Huntress, a cybersecurity firm valued at $3 billion, his path to the top didn’t start with an Ivy League degree or Silicon Valley internship. Instead, it all started in AOL chatrooms and online hacker forums.
Hanslovan described his younger self as a “shady” kid who spent his time pirating video games while living with his single mom in Florida. That inquisitive, self-taught nature caught the attention of the U.S. Air Force, which recruited him at 17 to put those hacking skills to work—this time, legally.
“When you grow up pretty darn broke, you have to learn and experiment,” Hanslovan told Fortune. “Sometimes you learn by getting your hands slapped, and sometimes you learn with success.”
He spent years in offensive cyber operations before transitioning to the private sector, supporting missions tied to the National Security Agency. There, he began to see how dramatically the threat landscape was changing. What once felt like a clever way to outsmart corporate firewalls or download a free video game had evolved into something far more serious. Hackers were increasingly targeting critical infrastructure, hospital systems, and small businesses.
That realization pushed Hanslovan to take a leap. In 2015, he left a stable career to cofound Huntress, a cybersecurity startup focused on protecting the small and midsize organizations that larger firms often overlook—from small-town accountant to the innovative tech startup.
After eating ramen and sleeping in his car while scaling to $3 billion, Hanslovan admits he ‘wouldn’t do it again’
The cybersecurity threat has only worsened in recent years: Americans lost $16.6 billion to internet crime in 2024, a 33% jump from the year prior, according to the FBI’s most recent cybercrime report. Ongoing geopolitical tensions and the rapid adoption of AI tools could make attacks even more sophisticated and damaging in the years ahead.
For Huntress, that threat has been great for business: it has scaled to over 700 employees across five countries and a $3 billion valuation. But according to Hanslovan, it didn’t come without serious sacrifice over the last decade.
“I slept in my car for most of Huntress in the beginning—we couldn’t get venture capital,” the 40-year-old recalled to Fortune. “I had 60 venture capitalists tell me no, and we had burned all of our founder cash.”
Hanslovan acknowledged that entrepreneurial grit alone isn’t unique—plenty of founders have weathered VC rejections or bootstrapped from a parents’ basement. Instead he believes that funneling early-life hardship into passion can be a genuine advantage.
“I actually think a lot of people that make it have some weird level of dysfunction as a child that just made them they could pursue through these hard times,” Hanslovan said. “So even though it wasn’t the greatest part of my life, I don’t regret it at all.”
Still, he’d make some changes. When he started Huntress, his three children were 5, 9 and 11 years old. Today they’re 15, 19, and 21—two have left for college, and a divorce has come and gone in between.
“I overrotated on work way too hard. The first eight years I believed in that hustle culture, grind culture,” he said. “… I missed a lot of the greatest years of their lives.”
“I probably wouldn’t do it all over again if I could,” he added.
Hanslovan’s advice to Gen Z: you don’t have to become Mark Cuban
For all his success, Hanslovan also admitted that it doesn’t necessarily come with automatic satisfaction.
“All the finances and all the glamor and all that has not made me any happier. If anything, it’s made me more disconnected,” he said.
Part of that dissatisfaction, he added, stemmed from a mindset he’d internalized early: that building a billion-dollar business was the benchmark for having made it.
“I just wish I would have known in the earlier days that I would have still been successful even if this didn’t turn into a $3 billion company,” Hanslovan said. “There are a lot of ways to make a difference that doesn’t just come with the dollars.”
He’d still advise Gen Z to pursue entrepreneurship—but only if they define success on their own terms. It’s a message that may land with a generation already moving in that direction. Nearly two-thirds of young people aged 18 to 35 say they’ve either started a side gig or plan to, according to a 2024 survey from Intuit, and nearly half say their primary motivation is simply to be their own boss.
Still, Hanslovan stressed against reaching for the moon if it’s not absolutely necessary.
“You don’t have to become Mark Cuban. You don’t have to create $3 billion Huntress to have a good life and provide for your family,” Hanslovan said. “There’s nothing wrong with progressing with a lifestyle business, a local business of their own, or something along those lines that allows them to be able to satisfy that gap.”
