Behind the scenes with Frank from Hacktoria: Coffee, cartels, and conspiracy theories

When you talk to Frank Diepmaat, the founder of Hacktoria, you get more than just insight into a cybersecurity project. You get anecdotes, laughs, and a whole lot of passion for storytelling, OSINT, and community-building. In our first article, we focused on the professional and technical journey of Hacktoria. Now, let’s take a more laid-back tour through the behind-the-scenes chaos, charm, and creativity that makes Hacktoria such a unique space.

Meet the Founder: Frank Diepmaat

Before launching Hacktoria, Frank spent over a decade in the IT world—working everything from sysadmin roles to cybersecurity in the telecom space. But behind the keyboard, he had a parallel passion: storytelling. He ran an online magazine and later a publishing platform, merging a love for fiction with his tech-savvy background. That unique combination led to Hacktoria, a story-driven OSINT playground where players become digital detectives in interactive, immersive challenges.

By day, he works in marketing. By night? He’s deep in the Hacktoria universe—building CTFs, brainstorming and sipping on energy drinks. His favorite challenges often come from spontaneous scribbles in the Notes app, inspired by games, movies, or just random “what if” ideas.

Frank’s vibe is equal parts hacker and creative—he’s more “deep house music and cyberpunk noir” than “red team ops and spreadsheets.” His go-to OSINT tool? Google. His most underrated cybersecurity skill? Understanding how systems are built before trying to break them.

Despite the mixed aesthetic of Hacktoria, Frank’s mission is clear: create a welcoming, troll-free space where people can learn, explore, and have fun with OSINT. Whether it’s through fake cartels, interactive stories, or brag-worthy Discord loot, Frank’s world-building turns CTFs into experiences—and makes cybersecurity feel a lot more like a game worth playing.

Say hi to Frank. Whether he’s crafting a digital spy mission, talking about conspiracy theories, or giving water to a horse from a bowl (yes, really—see below), he’s the creative brain keeping Hacktoria weird, welcoming, and one step ahead of the curve. Say hi, Frank :)

From Argentina with Love

One of the most endearing surprises during our chat was revisiting a Hacktoria challenge that used real vacation photos I had taken in Argentina —photos I had completely forgotten about!. Frank had built an entire CTF around a fictional Instagram account populated with these images. “It never got taken down,” he said, laughing. “But now we always take screenshots, just in case.”

That challenge became a fan favorite, not only for its authenticity but because, as Frank put it, “it really made people feel like detectives. They couldn’t reverse image search their way out."

Building Hacktoria, one espresso at a time

Frank shared that many of Hacktoria’s CTF ideas are scribbled on notepads or in the Notes app, often while sipping coffee and blasting deep house music. “I usually already have a few CTF ideas written down,” he said. “It’s just me in front of my laptop, drinking White Monster or coffee and building things.”
I couldn’t help but make a face. “White Monster? How could you,” I joked. “Mango is clearly the superior choice.”

We also talked about his co-founder, Joaquin Iglesias, a familiar name in the CyberSecurity space. Frank recalled how they connected on Instagram and eventually joined forces. "Now we brainstorm, manage the community, and run Hacktoria together."

Trolls, toxicity, and teaching moments

Running a community isn’t all spy plots and Easter eggs. Frank has a firm stance on toxicity: “We ban trolls immediately.” But what stood out was his commitment to “social learners” — people who learn by asking and interacting.

Hacktoria was built to be a welcoming space for people who thrive in collaboration.

And the community gives back. When a questionable image with a child appeared in a geolocation challenge, players flagged it immediately. “It turned out to be the player’s own kid,” Frank clarified, “but I loved how quickly people reacted. It shows the culture we’ve built.”

When the plot breaks the platform

Sometimes, creativity backfires. One memorable CTF featured a fake shipping company. Players were supposed to social-engineer a tracking number and plug it into a site Frank built. Instead, they brute-forced the form and broke the site. “DigitalOcean sent me a usage warning 10 minutes in,” he said, grinning.

Another time, a player accidentally stumbled upon a real medical scam in Argentina while investigating a character photo. “They messaged me like, 'Hey, is this part of the CTF?' Nope!” Frank laughed. “But that’s OSINT — sometimes, reality gets weirder than fiction.”

Aliens, Appalachia, and the future

One of the newer CTFs, Appalachian Aliens, involves a conspiracy website filled with real imagery and completely fictional storylines. Frank calls it "environmental storytelling," and it’s the direction Hacktoria is heading: deeper plots, richer context, more immersive experiences.

"We're moving away from quick wins. We want players to feel like they're uncovering a universe."

He hinted at an upcoming horror-themed challenge involving a shady murder hotel and teased long-term dreams of a physical geocaching component. “Imagine hiding Hacktoria geocaches around the world and having players find them in real life. That’s the dream,” he said.

AI, authenticity, and a dash of sarcasm

Naturally, we veered into AI. Frank, who has worked in the AI space, had sharp insights. “AI is just a tool. A powerful one, sure. But it’s only as smart as the data we feed it."

We riffed about AI-generated images (especially its struggles with guns), Microsoft’s use of PowerShell under the hood of Copilot, and the risks of relying too heavily on automated tools.

“If people stop learning, AI stops getting smarter. That’s the irony,” he said. “It needs us more than we need it.”

Frank Diepmaat is many things: a builder, a storyteller, a community wrangler, and a caffeine-fueled creative force. But most importantly, he’s someone who believes learning should be engaging, accessible, and maybe a little bit absurd.

Whether you’re hunting clues across Instagram, dissecting conspiracy theories, or roleplaying as a digital detective, Hacktoria offers more than just puzzles — it offers a place to belong.

And if you’re lucky, maybe you’ll end up in a future CTF. Just don’t try to brute-force the server.

Curious to dive into the Hacktoria world? Start your first contract at hacktoria.com and join the Discord for non-stop puzzles and banter.

Special thanks to Frank for the stories, the sarcasm, and the inspiration. I had a blast.