Chiper and Carolina García’s Hardest Lesson: Resilience Isn’t About Enduring. It’s About Deciding How to Move Forward

Carolina García had never planned to become an entrepreneur. She wasn’t the one selling things at school or dreaming of starting a company from a young age. In fact, she came to entrepreneurship by accident.

While working in consulting, she had the chance to get an up-close look at Colombia’s traditional retail channel: neighborhood shops, which remain the primary source of supplies for millions of people across Latin America. Something about that world captivated her.

It wasn’t just the scale of the opportunity, but also the impact she could have on the people behind the counter. Her first venture aimed to turn these shops into a financial hub for people at the base of the pyramid.

Years later, after studying at MIT and gaining more experience building companies, she returned to the same problem from a different angle. That’s how Chiper was born.

What began as a platform to help shops stock up more effectively eventually evolved into a company that now helps manufacturers, distributors, and wholesalers operate more efficiently using artificial intelligence.

But the company that exists today is very different from the one she first imagined.

Along the way, Carolina discovered something that sums up much of her experience as a founder: Entrepreneurship isn’t about building a company. It’s about managing uncertainty.

And perhaps that idea explains better than anything else how Chiper has evolved over the past few years.

What led you to become an entrepreneur?

I never had a life plan that said, “I’m going to become an entrepreneur.” I came to entrepreneurship after graduating from university, while working at a consulting firm where I had the chance to get a very close look at neighborhood shops in Colombia.

I found them fascinating economic actors. They’re small businesses, but they have an enormous impact on the communities where they operate. That’s where my interest in building solutions for them began.

My first venture aimed to turn these shops into a financial hub for people at the base of the pyramid. And although the company evolved over time, my determination to understand shopkeepers and help them operate more effectively is something I still carry with me today.

Chiper began by helping shops directly. How did you become a platform for manufacturers and distributors?

At first, we focused entirely on solving shopkeepers’ problems. We built a platform where they could buy inventory whenever they wanted, get it delivered quickly, and access better prices and product ranges.

But to make that work, we had to build all the infrastructure behind it: inventory, warehouses, logistics, pricing, and distribution. And in the process, we discovered something interesting. We weren’t the only ones with that problem.

Manufacturers, distributors, and wholesalers faced exactly the same technological challenges in reaching shops. So we started asking ourselves whether our technology could help them, too.

The answer was yes. Eventually, we realized that a much bigger opportunity lay there: helping those who already have relationships with thousands of shops operate better, sell more, and make better decisions. That was the origin of the pivot.

Who is Chiper’s ideal customer today?

Today, we work mainly with distributors, wholesalers, and manufacturers that sell through the traditional retail channel. They’re companies with broad product ranges, hundreds of SKUs, and sales teams that regularly visit shops.

Although each market has its own characteristics, their needs tend to be very similar. They all want to sell more efficiently, develop digital channels, better understand their customers, and optimize operational processes.

What differs from country to country is the market structure. For example, wholesalers have a much stronger presence in Mexico, while distributors predominate in Colombia. But the problems they’re trying to solve are quite similar.

You’ve spoken publicly about lessons learned during difficult periods. What was the most costly lesson Chiper taught you?

For a long time, I confused resilience with enduring. In the startup world, people talk a lot about not giving up, carrying on, and pushing harder when things get tough.

And I think for years I understood resilience that way. Over time, I realized that sometimes the problem isn’t execution. It’s direction. And the more a company grows, the harder it becomes to question the decisions that got you there.

Looking back, I think the costliest mistake was not having some difficult conversations when we should have. Conversations about expansion, strategy, priorities, or incentives.

We eventually had them, but only after investing far more time, money, and energy than necessary. Today, I believe one of a founder’s most important responsibilities is to dare to question difficult decisions before it’s too late.

What changed in the way you view entrepreneurship after Chiper?

At first, I thought entrepreneurship was simply about building. Over time, I realized it’s about managing uncertainty. I used to believe that if you worked harder, executed better, and made good decisions, the results would eventually come.

But then you come up against things you simply can’t control. The pandemic was a very clear example for us. There are also investment cycles, market changes, and external decisions that completely affect the context in which you operate.

That taught me that entrepreneurship isn’t just about controlling the outcome. It’s about making the best decisions possible with incomplete information. And then doing it again and again.

What’s next for Chiper this year?

Our focus is on expanding the use of artificial intelligence across all the platform’s modules. Today, we help our clients manage e-commerce, sales, inventory, warehouses, and various commercial operations.

What we want now is for artificial intelligence not just to display information, but to actively help people make decisions. The vision is for users not to have to spend time building reports or analyzing dashboards. We want the product to be able to interpret that information and deliver actionable recommendations to continually improve business results.

Is there anything you learned outside work that helps you as an entrepreneur today?

One thing I learned outside work was the importance of empathy. When you’re building a company, it’s very easy to become obsessed with results, metrics, and goals. And sometimes you forget that there are people behind all of it.

I developed that perspective mainly in women’s communities and spaces outside work. That’s where I realized that reaching a goal matters, but so does how you get there.

Today, I try to apply that not only within Chiper, but also in other kinds of initiatives I work on. Because ultimately, we build companies to make an impact on people. And often what lasts isn’t the results, but how we made the people who worked with us feel.

When resilience stops meaning endurance

Chiper’s story began by helping neighborhood shops.

What began as a platform to help shopkeepers stock up more effectively eventually evolved into a company that now helps manufacturers, distributors, and wholesalers operate more efficiently using artificial intelligence.

But after all the pivots, expansions, and strategy changes, one thing remains the same: Carolina’s obsession with understanding how the traditional retail channel works and how technology can help the people who make it possible.

Perhaps that’s why the most valuable lesson from this conversation has nothing to do with artificial intelligence, distribution, or technology. It has to do with something much harder.

For years, the entrepreneurial ecosystem celebrated the idea of carrying on at any cost. Work harder. Resist more. Endure more. But building a company also means questioning decisions, changing direction, and accepting when a strategy is no longer working.

And sometimes, the difference between a good decision and a bad one isn’t how much effort you put in, but how willing you are to have the difficult conversation you’ve been avoiding for far too long.

Because resilience doesn’t always mean continuing to push forward. Sometimes it means stopping, rethinking the path, and making a different decision before it’s too late.

Interview by:

Eduardo Hernández, Head of Startup Avenue at Volcano Summit and Partner at Leapstart, where he drives startup growth and the development of the entrepreneurial ecosystem. A former entrepreneur in the insurance sector, he has actively participated in initiatives such as Startup Weekend, Emprendedores Anónimos, Hackers/Founders, and Magma Partners.