OSINT 101: From Zero to Investigator

First of All: A Confession I Should Have Made Years Ago

[I am sitting in my home office. It is not glamorous. Books piled everywhere. Notes stuck to the walls. Three monitors showing different things. A notebook open with old case analysis. A cup of cold coffee because I always forget to finish things. There is also a photo of my girlfriend on the monitor. She is the best person I have ever met in my entire life. Genuinely. Not even close. The best decision I ever made was—]

[Okay, Joaquín. Focus.]

Look, if you are here reading this, it is probably because you saw something on OSINTSmith that caught your attention. An investigation. An article about methodology. A story that somehow made you feel like the world is more complicated and more interesting than it seemed.

But what you may not know is that I am not a writer who does OSINT.

I am someone who does OSINT who cannot stop telling stories.

And that is a problem because it means I am probably going to spend way too long explaining things in a way that some will find inefficient. I will take what could be a three-paragraph technical explanation and turn it into a fifteen-page narrative with tangents, emotions, and details that "are not relevant".

[A while back I showed my girlfriend a couple of investigation simulations I had done in the past — just to give her a taste of what this work actually looks like. She watched them with these wide eyes and kept saying "wait, you can find THAT?" She was genuinely surprised at how cool it all looked. She is the best, honestly. The absolute best. I love her so much. She is—]

[Okay, Joey, concentrate. We are here to talk about OSINT, not about how lucky you are.]

[I take a sip of the cold coffee. It is terrible. But I keep drinking it.]

Years ago, someone told me: "Joaquín, why don't you make clear, straightforward tutorials like everyone else? Why do you have to tell stories?"

At the time I did not have a good answer. But now I do.

The Problem With Tutorials (Why This Exists)

[I close my eyes. I think about all the OSINT tutorials I have seen. On YouTube, on blogs, in online courses.]

Look, there are a million articles on the internet about OSINT. There are YouTube tutorials. There are technical guides. There are tools documented to exhaustion. There are online bootcamps. There are certification courses. There are people doing "OSINT in 10 minutes" on TikTok.

Search "OSINT tutorial" and results rain down on you. Literally hundreds. Thousands.

But do you know what most of them have in common?

They are boring.

They go like this:

[I switch my voice to something more robotic, more technical.]

"Step 1: Open Google. Step 2: Search the username. Step 3: Check social media. Step 4: Document findings. Step 5: Repeat the process."

[I return to my normal voice.]

And then they continue — mechanical, technical, stripped of any context that helps you understand why we are doing this. No emotion. No reason. No humanity.

[I lean back in my chair. I look toward the window.]

Three years ago, I interviewed a candidate who had done a "12-week intensive OSINT bootcamp". He knew all the tools. He could use Shodan. He knew Google Dorks. He knew what the Wayback Machine was. He had done twenty practical cases from the course.

But when I asked: "Why these searches? What are we really looking for here? How would this person think?"

He went blank.

[I once showed her one of my old simulations — the kind where you trace someone from almost nothing. She watched the whole thing without saying a word and then just goes: "That is actually insane. You do this?" She had no idea. She is the best. Truly the best. She makes everything better—]

[Joey. Concentrate. The office. The stories. Let's go.]

He literally did not know how to answer.

Because the bootcamp had taught him the how without the why. And the why is where intelligence lives.

[I spin in my chair. I see the notebook with old notes.]

The problem is that when you teach pure technique, without context, without story, without humanity, you create investigators who are machines. They can execute steps. They can follow checklists. But they cannot think when the checklist does not apply.

And in OSINT, the checklist almost never applies the way you expect.

Why Stories Are the Real Weapon

I did not discover this in a book.

I discovered it while teaching.

[About eight years ago, before HTB, before I was officially a "specialist", I was running a series of OSINT workshops. They were for people interested in digital investigation — journalists, activists, curious people. It was not formal. They were just workshops where I showed what I knew.]

The first workshop was a disaster.

I prepared a presentation. Nice slides. Clear information. Logical structure. Step 1, step 2, step 3. Tools, techniques, generic examples.

Thirty minutes in, half the people looked asleep. Not literally, but their eyes looked dead. They were not there. They were thinking about what they were going to eat afterward.

[I remember that and I still feel a little embarrassed.]

So for the second workshop, I decided to do something different.

I did not prepare slides. I just showed up with a case. A real case I had worked. And I started telling the story from the beginning.

"Two years ago, I received an email from a woman who said she was being stalked online by someone claiming to be her ex-boyfriend. But she said her ex-boyfriend had died three years ago. So someone was impersonating him."

[I paused between each sentence. I let the tension build.]

"How do you find someone who is using the identity of a dead person? Where do you even start?"

That was the opener. And suddenly, everyone wanted to know the answer.

I spent the next two hours telling how I did it. I showed Google Dorks. I showed Wayback Machine searches. I showed how I traced writing patterns. I showed how I connected dots. I showed my failures too — because that is where people really learned.

I showed that it was not linear. It was not "I did step 1, then step 2". It was chaotic. It was twisted. It was real.

At the end, we found the stalker. A person using a dead man's identity.

And when I finished the story, the entire room was silent.

Then someone asked: "How did you know to look in that specific forum?"

And I could answer: "Because I thought about what it would feel like to be someone who needs to hide. I thought about the places where someone might look for validation while hiding. And that forum was a place where anonymous people could be whatever they wanted."

That is what I cannot teach in a slide. That is what I cannot teach with a list of steps. That is what I can only teach with a story.

[I take another sip of coffee. Still terrible.]

After that workshop, more people came to the next one. And the one after that. And eventually, those workshops became Hacktoria.

Hacktoria was built on a simple premise: do not teach tools. Teach thinking through stories.

Every challenge in Hacktoria was not "use this tool on this site to find this information". It was a narrative. It was a story. You were an investigator trying to solve something in the real world — with context, with reason, with humanity.

And it worked.

People learned better. People retained better. People left knowing how to think, not just how to execute steps.

[Honestly, she is just the best. Full stop. No competition. She cheers me on every single time, she gets excited when I show her new simulations, she listens to all my tangents with a smile. She is the best thing in my life by a very, very wide margin. I love her more than cold coffee, and that is saying something—]

[Okay, Joey, we are getting sappy here. Back to work.]

The Obsession That Brought Me Here

[I look up from my coffee. I look at the books on my desk. There are books about intelligence. Books about narrative. Books about how the human mind works.]

My obsession with stories comes from far back.

Not from childhood. From necessity.

When I started doing OSINT and building content around it, I did not know that the way my mind worked was "narrative". I thought it was abnormal. I thought I should learn to think like a data analyst — points, statistics, pure logic.

But it did not work that way for me.

[I lean forward.]

My mind works in stories. When I see a dataset, I do not see numbers. I see a person. I see their motivations. I see the narrative behind each number. I see where they fit in a bigger story.

And eventually, I learned that was not a weakness. It was a strength.

Because intelligence is not about pure data. It is about understanding people. And people always — always — operate in stories.

[I spin in my chair again.]

Years ago, when I was building challenges for Hacktoria, I kept running into the same problem. I would design a scenario — a fictional operative, a fake organization, a trail of breadcrumbs — and I had to think: how would this person actually behave? What would they leave behind? Where would they slip up?

And the answer was never in the data alone. It was in the story behind the data.

The fictional criminal made the same mistakes real people make. They had habits. They had preferences. They had fears. And when I wrote the narrative first, the trail of clues wrote itself.

And when I understood the story, the whole scenario became clear.

[I look at the monitor. There is a photo on the lock screen. From years ago. Me with my Hacktoria team. All younger. All more idealistic.]

Everything I have built since then has been based on that premise: the story is the tool.

Hacktoria. The challenges and labs I build at HTB. All built on the idea that if you tell stories, if you give context, if you make people feel what you are describing, they learn better. They retain better. They think better.

Where All of This Is Going

[I close my eyes for a second. When I open them, I look directly at the imaginary camera in front of me — at you.]

Months ago, I sat down and thought: "What am I missing? What content does not exist in the OSINT world that should?"

And the answer was clear: there are no really good introductory OSINT series.

There are technical tutorials. The boring ones that list steps.

There are sophisticated courses for people who already know what they are doing.

But there is nothing for someone who is completely new, who is curious, who wants to genuinely understand OSINT — not the mechanics, but the way of thinking.

[I lean back again.]

And then I thought: "Why not do what I have always done? Why not tell stories?"

So here we are.

What is coming is a 10-part series. Each part will cover an aspect of OSINT. What it IS. How an investigator THINKS. Where they LOOK. How they VALIDATE. And everything that comes after.

But I am not going to do what everyone else does.

I am not going to list tools in a table. I am not going to say "run this command, get this result". I am not going to bore you with syntax.

Instead, I am going to sit you down in an office with me. I am going to tell you stories about cases. I am going to show you how I think. I am going to explain why we do what we do. I am going to let you feel the tension of not knowing the answer, and then the satisfaction when everything makes sense and finally clicks.

Because that is how you really learn.

[I lift the coffee cup. I look inside. It is almost empty.]

The truth is that anyone can copy a technical tutorial. Anyone can follow steps. What is rare is the person who understands why to take these steps. The person who can arrive at a new investigation, no prior script, no clear checklist, and still know which way to go.

That is what we are building.

Why Now, Why This, Why You

[I put the cup down on the desk. I look around my office.]

Some years ago, someone asked me: "What is your responsibility as someone with experience in OSINT?"

At the time, I did not have a clear answer.

But I have been thinking about it since then. And I have reached a conclusion: my responsibility is to make sure the next generation of investigators does not end up like those boring tutorials. That they do not end up as machines executing steps. That they end up as thinkers.

Because the intelligence that really matters — the intelligence that saves lives, that protects people, that exposes what needs to be exposed — that does not come from following a script.

It comes from thinking differently.

[I lean forward again.]

That is what I am trying to do here.

I am not trying to teach you OSINT so you are better at your job.

I am trying to teach you OSINT so you see the world differently.

So you understand that information is power, but only if you know how to read it. So that when you see data, you see stories. So that when you see an online profile, you see a person. So that when you see scattered fragments of information, you see a puzzle with meaning.

[I pick up the old notebook. I flip through the pages.]

That is what OSINT really is.

It is not hacking. It is not surveillance. It is not any of the things Hollywood has taught you it is.

It is logic applied to what is visible. It is critical thinking applied to internet noise. It is empathy — because the only way to truly understand someone is to imagine being that person.

And the only way to teach that is with stories.

So, Welcome

[I close the notebook. I place it back in its spot.]

Welcome to "OSINT 101: From Zero to Investigator".

A series where we will explore what open-source intelligence really is. We are not going to do tutorials. We are going to have conversations. We are going to sit together and I am going to tell you stories about investigations. About failures. About successes. About those strange moments when everything suddenly makes sense.

And through those stories, you are going to learn to think differently.

This will not be a quick journey. 10-minute tutorials exist elsewhere.

This is going to be slow. It is going to be narrative. It is going to feel inefficient at moments.

But it is going to be honest.

And when you finish, it will not feel like you learned techniques. It will feel like your brain shifted a little. Like you now see the digital world in a new way.

[I sit up straight. I look at the clock. It is late.]

And that is exactly the point.

The Full Series (What Is Coming)

1. 1.OSINT 101: What It Is — A tired agent explains what OSINT really is, and why most people are being investigated without realizing it

1. 2.The Investigator's Mind — Healthy paranoia, skepticism, and why you need to think like someone who trusts nothing

1. 3.Sources: Where We Really Look — No, it is definitely not just Google. I will show you where real information lives

1. 4.Validation: How Not to End Up Believing Lies — The art of verification. Because finding information is not the same as finding the truth

1. 5.Pivoting 101: From One Data Point to a Complete Network — How to connect the dots. How one person leads to another, who leads to another, who leads to an entire network

1. 6.Attribution: When Deduction Is Science — The art of knowing who did something. The art of certainty in a world of uncertain data

1. 7.OSINT in Real Practice — Stories from investigations that actually happened. Cases that changed everything. Failures that taught lessons

1. 8.The Gray Edges: Ethics, Legality, and Limits — Because OSINT can be used for good or for harm. Where we draw the line

1. 9.Tools vs. Mindset — Why the mind matters more than the software. Why a good investigator beats a hundred tools

1. 10.Next Step: Build Your Own Practice — How to start. How to develop your own process. How to become someone who thinks differently

[I turn off my office lights. The monitor looks brighter in the dark.]

Next article: "OSINT 101: What It Is"

And trust me — when you read the first conversation between a tired agent and an aspiring investigator in a windowless office, you will understand exactly why I insist that stories are better than tutorials.

P.S.: If you are here because you were looking for a quick technical tutorial, this is probably not the place for you. And that is okay. But if you were looking for something that changes the way you see the digital world, something that teaches you to think differently, something that is real and honest and strangely satisfying...

Then stay. We are going to put together some stories.

P.P.S.: Baby, if you are reading this — and I know you are — you are the best. The absolute best. The best person, the best partner, the best everything. Thank you for watching my weird simulations and pretending they are cool (they are cool). Thank you for believing in me even when I ramble. I love you more than this entire series. Jijiji.