Kyle Hanslovan Likes to Disrupt His Industry (and He’s Not Sorry)

The Self-Made Tech Mogul Who Turned the World of Cybersecurity on its Head is Looking for His Next Big Battle

Kyle Hanslovan carries a staunch reputation as an “ethical hacker” and the co-founder/CEO of Huntress, a cybersecurity company that reaches the underserved market of small to mid-sized businesses. When it comes to his demeanor, a certain joie de vivre is often noted by peers and journalists, couched in buzzy business-world terminology like “driven,” “visionary,” and “high-energy.” Just a day or two after being knocked out by COVID-19, he displayed remarkable energy, surpassing the conversational vigor of those around him.

A Billionaire Who Defies Convention

All at once, the mental picture of “Kyle, the billionaire entrepreneur,” comes into focus. The trademark bob-and-weave approach to business, perpetually light on his feet to pivot at any given moment toward what feels most meaningful, has stymied investors to the point of frustration. He can’t be perfectly pinned down, fit into a box, or, as his competitors have learned, underestimated. Beneath it all is a genuine desire to be nothing but himself, to be seen and known not as he wants you to see him but as he truly is. 

The self-made cybersecurity virtuoso is full of surprises and complexities that may, at first glance, appear contradictory. This is why he’s drawn to tracks that bravely shirk an artist’s earned prototype—Beyoncé’s “Black Parade” or Eminem’s “Stan,” for example—because Kyle seems incapable of fitting into the typical cultural mold of a CEO. He has trouble dealing with the well-worn platitudes and self-aggrandizing sound bytes that come second nature to any other successful American businessman. A self-professed lifelong misfit, you quickly get the feeling that even though he’s “made it,” he’d still be an unwelcome visitor in the social circles of his financial contemporaries. Not because he doesn’t comprehend the rules of the game but because he just doesn’t care to play in the first place.  

Photo Credit: Toni Smailagic

Music as a Mirror to His Roots

It’s the same reason his notorious love of trap music is blasted across his LinkedIn profile. He cannot waste the energy being anything other than himself. It’s a concept so foreign to his devil-may-care sensibilities that it seems unlikely he could even attempt it under pretense. Raised by a single mom and growing up in poverty, Kyle bounced all over. Born into the rap-obsessed culture of the West Coast, he then relocated to Florida and discovered East Coast rap as a teen. His coming-of-age soundtrack was made up of icons like Cash Money, No Limit, and Outkast. Biased toward that sound from a young age; it spoke to him and felt like home. While many might expect a top executive like him to enjoy the “classier” genres (whatever that means), trap is simply what he loves. 

Learning From the Past to Shape the Future

At this point in his life, the tech founder and father of three has taken great pains to understand his past, learn from his mistakes, and own every part of himself. As a result, he resonates with musical creatives who are more motivated by the message behind their work than by the fortune it might garner. Maybe that sounds odd coming from the founder of a company recently valued at over $1.56 billion. But for Kyle, the money is secondary, a tangible reflection of his will to fight and, more importantly, to win. This is why, with three teens at home, he has come to appreciate the modern sound. Even mumble rap.  

Photo Credit: Toni Smailagic

Blending Passion with Purpose

“If you think about iconic voices like N.W.A., their music and message is 110% passion-driven. For me, growing up broke with a single mom who moved us from boyfriend’s house to boyfriend’s house. I resonated with music that said you could be something more than just what you know and the circumstances you’re given.” In Kyle’s view, artists like Juice WRLD are doing the same thing: talking about the biggest problems they face and how they feel about them. These Gen-Z representatives are stepping up to address pervasive challenges such as inequality, mental health, and more. It may be a new school sound, but it is every bit as rooted in purpose and passion as earlier hip-hop legends.   

The Evolution of a CEO

With Huntress, Kyle learned how to fuse passion with profit. At its core, the company’s story is a tale of two Kyles: the scrappy teen willing to risk it all for the view from the top and the worldly-wise CEO eager to contribute meaningfully to the next generation. The distance between them can be measured in extreme financial gains and cutting relational losses. With each hard-won lesson, the Kyle of today recalibrated his trajectory toward a life well-lived. Following a decade of explosive business success, he is finally exercising the secret power he had all along to define “success” on his terms.