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Kyle Hanslovan: The S--- Starter Leveling Up the Game On and Offline

kyle hanslovan the s starter leveling up the game on and offline
Source: Toni Smailagic

Jan. 23 2025, Published 3:00 a.m. ET

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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 midsized businesses. Peers and journalists often note a certain joie de vivre in his demeanor, couched in buzzy business-world terminology like "driven," "visionary," and "high-energy." Just a day or two after being knocked out by COVID, he not only met but even exceeded my conversational vigor.

All at once, my 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.

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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 our cultural CEO typology himself. He has trouble dealing with the well-worn platitudes and self-aggrandizing sound bytes that come second nature to any other successful white 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.

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kyle hanslovan the s starter leveling up the game on and offline
Source: Toni Smailagic
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It’s the same reason his notorious love of trap music is blasted across his LinkedIn profile. He cannot waste the energy by being anything other than himself. It’s a concept so foreign to his devil-may-care sensibilities that I’m not sure he could even do so 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. Icons like Cash Money, No Limit, and Outkast comprised his coming-of-age soundtrack. 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.

At this point in his life, the tech founder and father of three has taken enormous 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.

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“If you think about iconic voices like N.W.A., their music and message is 110 percent 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.

Like him, such artists are seen as disruptive. That is a label Kyle has borne for over a decade, and proudly—though he isn’t a huge fan of the term itself. “‘Disrupter’ is such a played-out word,” he shares. “I didn’t exactly set out to change the game. I just like to start s---.” Seeing an opportunity to use his somewhat controversial skills in the service of companies who needed them, he refused to listen to anyone who said it couldn’t be done. After all, successful business building requires what Kyle deems “a certain level of delusion.” Willing to be the only person on the trail, even with nobody in his corner, he endured for as long as it took. “When you’re operating in that place of pure passion, you aren’t worried about questions like ‘Is this relevant?’ You just keep pushing to get the dopamine hit from bringing your vision to life and making it work.” F--- the haters.

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kyle hanslovan the s starter leveling up the game on and offline
Source: Toni Smailagic
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It’s precisely this unapologetic approach to business and life that has landed Kyle here. He isn’t trying to be an a--hole. He simply takes himself and his work seriously, and he expects those around him to do the same. He will be the first to own up to any mistakes made along the way, but he doesn’t believe in apologizing for living your life. “Something I’m trying to teach my kids, and especially my two girls, is that you don’t need to say sorry just for existing. I see too many women apologize for things like their kids interrupting a Zoom call or taking up space in the grocery aisle. When you do that, you diminish your position of power.” Instead, Kyle encourages his kids and peers alike to stand behind their choices, say what they mean, and fully inhabit their space—at work and at home.

He is also a staunch advocate of the AI movement, but not for the reasons most might think. He sees this burgeoning technology as an equalizer of sorts, empowering those across multiple industries to achieve bigger and better things with little to no access to capital. “When it comes to the music industry, AI will ultimately democratize the production process, enabling a completely new and diverse group of artists to share fresh perspectives we haven’t yet seen.” Even in his own cybersecurity field, Kyle eagerly anticipates the advancements that will come from standing on the shoulders of AI to reach the next level of what’s possible. Not exactly an anarchist in the true sense of the word, he still loves nothing more than to see traditional or outdated systems deconstructed and improved upon. It’s his entire MO.

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Plus, now that Huntress is running like a well-oiled machine and his kids are getting older, Kyle is seeking out his next big battle. When he says he’s ready to give back more than he’s taken, he means it. “I want to support others who seek to do what I did: prove absolutely wrong the way certain things are done by destroying and rebuilding.” He’s looking for innovators who like to drive a little bit faster than what’s currently allowed and refuse to stay inside the lines that are painted—not just for their own personal gain but for the greater good of humanity. “I'm not a super religious guy, but I am spiritual in the sense that I believe we all have a bigger purpose. Part of that is leaving things better than we found them.”

Kyle started out in the tech game with something to prove. Now that he has accomplished that task, it’s his turn to help others prove to the world the amazing feats that can be accomplished. Each pivotal life decision, from joining the military at seventeen to turning down multiple Fortune 500 roles in favor of building his own empire, reinforced the belief that he could become more than everyone expected. Along the way, he discovered more about the world and his purpose—the bigger picture of his one brief life. “There is so much we can do with our time here on earth beyond chasing dollars.”

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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.

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