The Most Expensive Mistake After an "Exit": Confusing Liquidity with Freedom

A few days ago, I was invited to talk with a group of entrepreneurs about wealth and investment. Personally, I like to speak from my own journey. I prefer sharing what I’ve lived—the stumbles, the mistakes, and those lessons that don’t come in books but leave a permanent mark.

I started in 2005, earning $200 a month. Yes, two hundred. With that, I paid rent, food, college, transportation, and dreams. Through work, mistakes, and a few well-placed bets, I eventually reached a point where I no longer work for money, but for enjoyment. Yet when I reached that independence, a question arose that no one teaches you how to answer: what do I do now with the capital?

Many entrepreneurs dream of the exit. Few understand that the hardest part comes after. Because when you finally have money in your account, the adrenaline of growth fades... and the vertigo of emptiness appears. You wake up and think: what should I invest in without losing what took me years to build?

And no, my advice isn’t to buy a house. That’s the easy answer. The real question is how to turn that capital into freedom—not into anchors.

I have a personal rule based on three words: protect, multiply, liberate. Because having money without knowing how to take care of it is like winning a game and losing the trophy in the locker room.

In these years in venture capital, I’ve learned something we often forget in Latin America: every investment carries risk—even the ones that seem “safe.” The key is not eliminating risk but managing it. And that’s where a strategy changed the way I think: Nassim Taleb’s barbell concept, from The Black Swan.

Taleb suggests dividing your wealth into two worlds: one boring and stable, and another wild and potentially explosive. It’s a balance—training your financial muscle with two weights: security and opportunity.

In simple numbers: 80% in safe assets, 20% in risky ones. The safe side might be bonds, fixed deposits, or index funds. They won’t make you rich overnight, but they’ll let you sleep peacefully. The remaining 20% is your playground: invest in startups, the idea that keeps you up at night, or crypto if you truly understand the terrain. That 20% is where you learn, reinvent yourself, and stay connected to the creative energy of entrepreneurship and work.

Unfortunately, in Latin America, the biggest risk isn’t in the investments—it’s in the advice. Our region is full of “experts” who speak without knowing. Everyone has a magic formula, an unmissable opportunity, a friend who “made a killing” with some fund or business. But let’s be honest: would you take flying advice from someone who’s never piloted a plane? Then don’t take investment recommendations from someone who’s never lost their own money in the market.

Taleb has a phrase that captures it brilliantly: if the advice is free, you’re the product.

I had to learn that the hard way. With an engineering background, I knew nothing about finance, and my first decisions were a disaster. I lost more than I care to admit. That’s why I became obsessed with learning—postgraduate studies, courses, certifications in finance and investing.

Today, I understand that financial education is an entrepreneur’s shield. Not to become a "money guru", but to avoid being naïve about it.

This column doesn’t pretend to be the Holy Grail of investing. It’s just meant to remind you that your capital is not only the fruit of your work, but the symbol of your battles. And if tomorrow you finally achieve that exit you’ve dreamed of, don’t make it your finish line. Make it the beginning of your freedom.

Jose Kont is an entrepreneur in the media industry and a venture capital investor, currently serving as a Venture Partner at Impacta VC and CEO of Cuantico VP.