The Self-Made Tech Mogul Who Turned the World of Cybersecurity on its Head is Looking for His Next Big Fight
Kyle Hanslovan carries a staunch reputation as an “ethical hacker” and the founder of HUNTRESS, a cybersecurity company reaching 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, 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 so as to pivot at any given moment toward what feels most meaningful, that 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 besides himself, to be seen and known not as he wants you to see him but as he truly is.
In fact, the self-made CEO of HUNTRESS cybersecurity 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, dealing in 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. He won’t waste the energy. It’s a concept so foreign to his devil-may-care sensibilities that I’m not sure he could even do so under pretense.
At this point in his life, the tech founder and father of three has taken great pains to understand himself, learn from his mistakes, and own his fallibility. As a result, he resonates with musical creatives more motivated by the message behind their work than 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.
Q: Your notorious love of trap music is so ingrained, it even appears as a headline on your LinkedIn profile. Why does that genre speak to you more than others?
As the kid of a single mom growing up in poverty, we bounced all over. I was brought up in the rap culture of the West Coast, then relocated to Florida and East Coast rap as a teen. My coming-of-age soundtrack was made up of icons like Cash Money, No Limit, and Outkast. I was just biased toward that sound from a young age. It spoke to me and felt like home. It still does. I’m sure many people expect someone like me to listen to “classier” genres, whatever that means, but trap is what I love.
Q: Many 40-somethings struggle to appreciate today’s music, but you’re known for embracing the uncomfortable. As a father of three teenagers, what’s your take on their current playlists?
Look at the things old-school hip-hop artists like N.W.A. stood for. The music actually had a point. It was 110 percent passion-driven. It had a voice: here’s the oppression, here’s where we’re getting pushed down. For me, growing up broke with a single mom who moved us from boyfriend’s house to boyfriend’s house, I could resonate with stuff like that. Music that said you could be something more than just what you know and the circumstances you’re given. I think Gen-Z music is the same. Artists like Juice WRLD are talking about the biggest problems they face: inequality, mental health, and obstacles that still affect this generation. I can get behind that purpose, even when it's in a different form like mumble rap. Some of the new-school music is just as deeply rooted in purpose and message as the original hip-pop I love.
Q: Founding HUNTRESS earned you the title of “disrupter” in the cybersecurity realm. What motivates you to keep pushing the envelope and sustaining a level of relevance?
First of all, “disrupter” is such a played-out term. I didn’t set out to change the game, necessarily. I just like to start sh*t. I saw an opportunity to use my somewhat controversial skillset in the service of companies who needed it, and I wouldn’t listen to anyone who said it couldn’t be done. Look, to successfully found a business, start a movement, or create something meaningful, you have to own a level of delusion. You have to believe “I can do this” and be willing to be the only person in your corner for as long as it takes. And 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 that dopamine hit of bringing your vision to life and making it work. F*** the haters.
Q: Your unapologetic approach to business is part of what landed you here. How does it play out in your personal life?
Hey, I’ll apologize where and when I need to. I’m not trying to be an asshole. But something I’m trying to teach my kids - and especially my two girls - is that you shouldn’t say you’re sorry just for living your life. I notice way too many women apologizing for things like kids interrupting a Zoom call or arriving a few minutes late to a meeting. These diminish your position of power, and they’re not anything you can control. I believe in standing behind your choices, saying what you mean, and taking up some space in the room. And I expect my kids, partner, team members, and colleagues to do the same.
Q: So as a tech guy, talk to me about the role you see artificial intelligence playing in the music industry.
If you are in the music industry, AI is about to crush you. From my vantage point, that’s not a bad thing. AI is about to completely democratize a lot of the production behind the music. Previously, you had to somehow get the capital to create a sound polished enough for mainstream play. Today, AI is going to empower a completely new, diverse group of artists to tell fresh stories and honest perspectives we haven’t yet seen. I’m most excited to see how artists stand on the shoulders of AI and take it to the next level, showing us an entirely different music model.
Q: Now that HUNTRESS is running like a well-oiled machine, your kids are getting older, and you’re looking to the next phase of life, is there a particular mantra or perspective that guides your approach?
I want to give back more than I take - literally. By that, I mean 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. These are folks who wanna 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 advancement but for the greater good of humanity. I'm not a super religious guy, but I am spiritual in the sense that I do think we all have a bigger purpose. Part of that is leaving things better than we found them. I started out in this game with something to prove, and now that I’ve accomplished that task, I want to help others prove to themselves the amazing feats they can accomplish. I joined the military at seventeen to gain better opportunities and to prove that I could be more than what everyone (including me) thought. That choice helped me to see the world - and our purpose in it - as so much bigger. There is so much we can do with our time to give back and not just chase dollars. But with HUNTRESS, I learned we can fuse our passions and plans to achieve both.
The story of HUNTRESS is, at its core, 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 success in business, he is finally exercising a secret power he had all along: the ability to define “success” on his own terms.