Inside Hack The Box: Community, Grit, and Growth

Our recent visit to Hack The Box HQ as part of the Scale-up Greece Meetup was nothing short of inspiring. In a room full of scale-up entrepreneurs and aspiring founders, the team at Hack The Box, including its CEO, Haris Pylarinos, and SVP of Product, Gerasimos Marketos, reminded us that meaningful growth sometimes begins as a side project, driven by a growth mindset and a tight-knit community. 

From Side Hustle to Global Force

Hack The Box didn’t start with VC money. In fact, Haris candidly shared that risk financing was a new concept to him. Instead, the platform began as a side hustle while he was working full-time; “If it makes €1,000–2,000 a month, we’re good”, he reflected on the early days. But that humble spark quickly spread. Fueled by the enthusiasm of a fast-growing user base and a deepening passion for the product, the team found themselves turning down a 7-figure acquisition offer before even raising their seed round. Talk about having the guts to bet on growth.

The Power of the Community

For me personally, one of the most powerful takeaways was this: “You don’t engineer community, you participate in it”. Hack The Box didn’t just build a platform. They joined forces with like-minded security enthusiasts, solving real problems, sharing knowledge, and continuously learning together. This organic participation led to what is now a 4-million-strong global community of ethical hackers, professionals, and learners.

From individual enthusiasts subscribing at $10/month to those same users becoming internal champions who brought HTB into their organizations, the community became their go-to-market strategy; not because of a marketing plan, but because of trust and word-of-mouth.

Lessons in Scaling

Haris described the company’s journey as a series of milestones, always setting the next goal as soon as the previous one was reached. That mindset of growth as a journey, not a finish line, came through clearly in the conversation. When asked what he’d do differently, he reflected: 

“I would raise sooner. Capital fuels growth”.

At Scale-up Greece, we often say that funding isn’t the goal; it’s a tool. Money can validate your impact and give you the means to scale it, but if your only motivation is financial, it’s rarely enough to sustain you through the tough times. As Haris put it:

“Money is a byproduct. It comes along the way, but it’s not the why. Giving back to the community and seeing all these people grow alongside you… that’s more satisfying than any amount of money”.

Hack The Box exemplifies that growth happens by staying close to the people you serve. What truly matters is clarity of purpose, a commitment to solving real problems, and surrounding yourself with people who share your belief in the mission. Sometimes scaling comes quietly, one user, one conversation, one solved problem at a time.