Why I’m Building OleOle Again, Twenty Years Later
My first World Cup was Mexico 1986.
The truth is, I didn’t go because I loved football.
I went because I was selling tickets.
At the time I was an American ticket broker trying to fulfill hard-to-get ticket orders. Football wasn’t really on my radar. I knew baseball. I knew American football. I knew basketball.
Football, at least the version played everywhere else in the world, seemed strange.
I remember watching part of an Argentina match.
Maybe twenty minutes.
I wasn’t impressed.
The players just kicked the ball around.
Nobody scored.
The game felt slow.
I remember thinking, “What is the big deal?”
What I didn’t know was that I was watching one of the greatest teams in football history.
What I didn’t know was that Argentina would go on to win the World Cup.
What I didn’t know was that a player named Diego Maradona was performing magic on a football field.
Most importantly, I didn’t understand what football meant to the people around me.
That understanding came later.
Over the next four decades I attended World Cups, European Championships, Champions League Finals, league matches, derby matches, and international fixtures all over the world.
Slowly, football got under my skin.
It’s difficult to explain to Americans.
Football isn’t just a sport.
It’s an inheritance.
Many football supporters don’t choose their clubs.
Their fathers chose them.
Their grandfathers chose them.
The club becomes part of the family story.
Part of the local culture.
Part of personal identity.
In football, supporting a team isn’t a hobby.
It’s a lifelong commitment.
And unlike many sports, football teaches you how to suffer.
The beauty of football isn’t winning.
The beauty of football is surviving the losses.
Every fan loves their club when they’re winning trophies.
The real supporters are the ones who stay when everything goes wrong.
The ones who keep showing up.
The ones who travel.
The ones who believe next year will be different.
The ones who inherit hope generation after generation.
Somewhere along the way, football stopped being a business for me.
It became a passion.
I caught the same disease that billions of football supporters around the world have.
And once you catch it, there is no cure.
Only football.
That passion eventually led me to an idea.
An idea I called OleOle.
The First OleOle
I started OleOle in 2006.
Long before smartphones dominated our lives.
Long before TikTok.
Long before WhatsApp.
Long before anyone was talking about creator economies, AI, blockchain, stablecoins, or super apps.
I believed football fans deserved something better.
After decades of traveling the world, I had seen something most Americans never get to experience.
Football wasn’t just a sport.
It was a global culture.
Three billion people connected by a shared passion.
More than 20,000 professional clubs.
Hundreds of leagues.
Thousands of competitions.
Millions of stories.
The opportunity seemed obvious.
The problem was that I couldn’t figure out the product.
I knew what I wanted to accomplish.
I just couldn’t figure out how.
The Most Expensive Mistake I Ever Made
When I started OleOle, I had something I don’t have today.
Money.
I had enough money to hire people who were supposed to be smarter than me.
So that’s exactly what I did.
I hired one of the top marketing and design firms in the world. They worked with companies like Apple. I believed they would help me figure out the product.
After all, they were the experts.
I wasn’t.
The problem was that every concept they showed me felt wrong.
It wasn’t bad work.
It just wasn’t OleOle.
What they kept showing me were variations of products that already existed.
Different layouts.
Different navigation.
Different versions of somebody else’s idea.
Nothing revolutionary.
Nothing that truly reflected how football supporters experienced the game.
Then I met several highly respected executives from Yahoo! Sports.
These were talented people who understood sports media at the highest level.
Surely they could help.
They couldn’t.
What they delivered wasn’t any closer to the vision than the agency had been.
Years later I finally understood why.
I was asking other people to invent my product.
That was never their job.
Nobody could see what I was trying to build because it only existed in my head.
The most expensive lesson of my entrepreneurial life was learning that vision cannot be outsourced.
You can hire engineers.
You can hire designers.
You can hire marketers.
But the founder has to own the product.
The founder has to understand every decision.
The founder has to obsess over every detail.
Twenty years ago I didn’t understand that.
Today I do.
Eventually I shut OleOle down in early 2011.
At the time, it felt like failure.
Looking back, it was education.
Learning What I Didn’t Know
After shutting OleOle down, I spent years trying to understand why some products become part of people’s daily lives while others disappear.
I started reading.
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A lot.
One book in particular changed the way I thought about technology.
The Viral Loop.
For the first time I understood that Facebook, Twitter, and other social platforms weren’t growing by accident.
There were mechanics behind the growth.
There were systems behind the behavior.
There were deliberate product decisions that created network effects and viral loops.
What looked like magic was actually design.
The more I learned, the more I realized how little I understood during my first attempt.
Then I started studying China.
I read books about Chinese technology companies.
I traveled to China.
Most importantly, I experienced WeChat.
That experience completely changed my perspective.
In the West, we think of social media as separate products.
One app for messaging.
Another for content.
Another for payments.
Another for commerce.
Another for services.
WeChat showed me something different.
For the first time, I wasn’t looking at a social network.
I was looking at infrastructure.
I was looking at a platform that had become part of everyday life.
That realization fundamentally changed the future of OleOle.
I stopped thinking about building another sports website.
I started thinking about building a football ecosystem.
Why Now?
In 2024 I decided to start again.
Many people think that’s crazy.
After all, everybody says social media is over.
Facebook exists.
Instagram exists.
TikTok exists.
WhatsApp exists.
X exists.
Why build another platform?
Because I don’t believe social media is over.
I believe generic social media is over.
The future belongs to communities built around shared passions.
Football happens to be the largest passion community on Earth.
And unlike 2006, the technology now exists to build what I originally imagined.
Artificial Intelligence changes everything.
Real-time translation changes everything.
Blockchain changes everything.
Stablecoins change everything.
Cloud infrastructure changes everything.
Twenty years ago, if a Real Madrid supporter in Tokyo wanted to communicate with a supporter in Mexico City, language was a barrier.
Today it doesn’t have to be.
A fan writes in Spanish.
Another reads it in English.
Another reads it in Arabic.
Another reads it in Portuguese.
Nobody thinks about the translation.
It simply works.
The technology disappears and the conversation becomes the focus.
The same philosophy applies to many of the things we’re building.
Every user receives a Wallet ID whether they ever transact or not.
Most users won’t care.
That’s fine.
The infrastructure is there before it’s needed.
The best technology is invisible.
Users don’t care how it works.
They care that it works.
Starting Over With Nothing
The irony of this story isn’t lost on me.
When I started OleOle in 2006, I had money but no product.
When I restarted OleOle in 2024, I had a product vision but almost no money.
If you spend twenty years pursuing ideas and generating little income, eventually you run out of money.
That’s reality.
But something unexpected happened.
People started showing up.
Engineers.
Designers.
Architects.
Builders.
People who could work almost anywhere.
People who believed in the vision.
Not because I could pay them.
Because they wanted to help build something that doesn’t exist.
Every startup story talks about capital.
Not enough startup stories talk about belief.
At some point every company begins because a group of people decide to believe before success exists.
That is where we are today.
Slowly building.
One component at a time.
One decision at a time.
One step closer every day.
Why OleOle Exists
OleOle exists because I believe football deserves its own ecosystem.
I believe football fans deserve a platform that puts sports before advertising.
I believe language should never be a barrier between supporters.
I believe communities matter more than algorithms.
I believe football is the most global culture on Earth.
And I believe technology should bring people together, not divide them.
Will we succeed?
I honestly don’t know.
Building a platform is hard.
Trying to connect billions of football supporters may be one of the hardest challenges in technology.
But I know this.
Twenty years ago I had the dream but not the knowledge.
Today I have the knowledge, the technology, and a team of people helping turn that dream into reality.
Maybe that’s why the first OleOle failed.
Maybe it wasn’t supposed to work.
Maybe I needed twenty years of mistakes, lessons, books, travel, failures, and experiences to understand what OleOle was truly meant to become.
The funny thing about dreams is that they don’t always arrive when you expect them to.
Sometimes they come back eighteen years later.
And sometimes they’re bigger than you imagined the first time around.
