We recently connected with Gabriel Felipe Osorio and have shared our conversation below.

Gabriel Felipe, thanks for joining us, excited to have you contributing your stories and insights. Being a business owner can be really hard sometimes. It’s rewarding, but most business owners we’ve spoken sometimes think about what it would have been like to have had a regular job instead. Have you ever wondered that yourself? Maybe you can talk to us about a time when you felt this way?

I’ve experienced both sides, and for me, entrepreneurship is infinitely more rewarding. When I began my entrepreneurial journey, I was on my own—figuring out everything. Marketing, sales, operations, finance, management—you name it. That experience alone accelerated my knowledge and deepened my passion for business.

I spent countless hours reading, networking, researching, building websites, crafting content, launching marketing campaigns, and managing finances. But you might wonder: Why would anyone choose to work 14+ hours a day? What’s the motivator? How could that possibly be fulfilling?

Here’s the thing: as an international college student with limited work hours (20 hours a week at $8/hour), financial instability was my reality. My soccer scholarship covered tuition, and my family helped with some expenses, but I was barely scraping by—capped at a mere $600/month. That’s when the existential questions hit: Why is someone else deciding how much my time is worth? Who made that rule, and why am I abiding by it?

That wake-up call changed my life. I realized I had to figure out how to take control of my income and stop letting others dictate my worth.

That’s where my entrepreneurial journey truly began, and it has been transformative. Since then, I’ve started five businesses—four of which failed. Despite those failures, I’ve worked alongside incredible professionals from Peru, Colombia, the U.S., and beyond. Those experiences have fueled both personal and professional growth in ways I never imagined.

In 2022, after years of running my businesses, I took a role at a boutique consulting firm. It was an incredible opportunity that taught me so much about business operations—SOPs (standard operating procedures), systems, turning insights into action, networking, and professional etiquette. I loved the work: creating business plans, developing strategies, analyzing data, and, for the first time, earning a decent income doing what I loved.

But here’s what I realized: no matter how much I enjoyed consulting, there was a ceiling to my impact. I wasn’t the business owner implementing the strategies. I wasn’t the one creating value for customers, jobs for employees, or opportunities for stakeholders. That gap left me frustrated and craving the sense of ownership and responsibility that only entrepreneurship could offer.

There’s something extraordinary about being a business owner. Yes, it’s challenging—stressful, even. But the impact we create in our communities, for our employees, and in our own lives is incomparable. It’s a trade-off, but for me, it’s one that’s worth it.

Entrepreneurship isn’t just about the work. It’s about the purpose, the growth, and the ripple effect we create in the world. That’s what makes it fulfilling.

Awesome – so before we get into the rest of our questions, can you briefly introduce yourself to our readers.

I’m an entrepreneur with over five years of experience building businesses, complemented by a year in consulting. My journey into entrepreneurship began during my college years when I was navigating financial instability as an international student. The experience pushed me to question traditional structures and seek ways to control my income and time. Over the years, I’ve founded multiple ventures, faced challenges, embraced failures, and gained invaluable insights that have shaped my approach to business.

Today, I form part of the founding team of Wesdom, a software solution company focused on facilitating organizations to achieve digital transformation. At Wesdom, we specialize in offering software solutions to streamline operations, enhance digital experiences, and solve complex business challenges. Our expertise lies in offering SaaS applications, Mobile applications, and other cutting-edge solutions designed to simplify and optimize processes.

At Wesdom, we aim to address the hurdles businesses face in adopting modern technology. From inefficient workflows and siloed systems to cumbersome integration processes, our solutions are designed to help organizations:

Improve operational efficiency.
Enhance communication between applications and third-party services.
Deliver superior digital services to their clients.
We focus on flexibility and scalability, ensuring our clients can adapt and thrive in dynamic markets.

Our strength lies in combining technical expertise with a deep understanding of business strategy. We’re not just software providers; we’re partners who work closely with our clients to craft solutions that align with their goals and long-term vision. Our commitment to agility ensures that implementations are swift and effective, minimizing downtime and maximizing value.

I’m proud of the impact I have had in the organization in recent years. Along with executive members we promoted a shift in the business model and how we were offering our solutions to businesses. We are launching our first open to the market software solution called UnityFlow with teams across the U.S., Colombia, and Peru. Building Wesdom has allowed me to work with brilliant professionals across the globe and tackle projects that deliver real, measurable results. I’m particularly proud of the way we’ve helped organizations modernize their operations, empowering them to grow and compete in an increasingly digital world.

At Wesdom, we’re driven by a passion for solving problems and creating opportunities. We believe digital transformation isn’t just about technology; it’s about unlocking the potential organizations have. Whether you’re looking to streamline processes, improve customer experiences, or explore new possibilities, we’re support organizations to achieve goals with software solutions and a team of technical experts to support business leaders and technical teams.

How about pivoting – can you share the story of a time you’ve had to pivot?

For over 20 years, my dream was clear: to become a professional soccer player. Soccer wasn’t just a sport for me; it was my identity, my passion, and the driving force behind everything I did. I poured countless hours into training, dreaming of the day I’d play on the world’s biggest stages. But life doesn’t always unfold the way we plan.

After a devastating broken hip and hand, my dream came crashing down. It was a heartbreak like no other—the kind that forces you to question everything. What happens when the very foundation of your life is pulled out from under you? For a while, I didn’t have the answer.

But challenges, as I’ve learned, often hold the seeds of opportunity. After seven surgeries and months of physical recovery, I made the decision to channel my passion and discipline into something new: martial arts. It wasn’t just a hobby or a way to pass time—it became my second calling.

In just three years, I’ve climbed to the rank of red belt in karate, a journey that has tested me in ways I never imagined. Martial arts demanded resilience, adaptability, and an entirely new mindset. Where soccer taught me teamwork and strategy, karate has instilled a deep sense of focus, self-discipline, and inner strength.

The lessons from this journey have shaped not just my personal life but also my professional one. In martial arts, just as in entrepreneurship, you must face challenges head-on, adapt to changing circumstances, and remain disciplined in the face of uncertainty.

That same mindset drives me as the founder of Wesdom. Whether it’s crafting solutions for businesses or navigating the complexities of digital transformation, I approach every challenge with the resilience and adaptability I’ve honed both on the field and in the dojo.

For me, martial arts is more than a sport; it’s a way of life. It’s a testament to the power of reinvention and the idea that when one dream ends, another can begin. If there’s one thing I want others to take away from my story, it’s this: setbacks don’t define us. What defines us is how we respond—how we choose to rebuild, adapt, and move forward stronger than before.

Whether it’s breaking boards in karate or breaking barriers in business, I’ve learned that the key to success lies in resilience, reinvention, and an unshakable belief in the power of persistence.

Are there any books, videos, essays or other resources that have significantly impacted your management and entrepreneurial thinking and philosophy?

Over the years, certain books and resources have profoundly shaped my entrepreneurial philosophy, management style, and approach to both business and personal development. I truly believe that books are more than just sources of knowledge—they are mentors, catalysts for growth, and keys to unlocking new perspectives. Each one has provided invaluable insights that I’ve applied to my career and life, often changing the way I approach challenges and opportunities.

Here are some that have significantly impacted my journey:

The Way of the Superior Man by David Deida
This book goes beyond traditional self-help, offering profound insights into purpose, relationships, and personal growth. It’s been instrumental in teaching me how to lead with authenticity and balance, qualities that are vital in both life and leadership.

Building a StoryBrand by Donald Miller
This book revolutionized the way I approach communication and marketing. It taught me how to simplify complex messages and create compelling brand narratives that resonate with customers by making them the hero of the story.

The One-Page Marketing Plan by Allan Dib
A practical, no-nonsense guide to marketing that breaks down the complexities into actionable steps. It’s a go-to resource that has helped me build strategic marketing campaigns that deliver measurable results for my business.

Twelve Months to a Million by Ryan Daniel Moran
This book was a powerful motivator in helping me understand the mechanics of scaling a business to seven figures. The focus on mindset, execution, and creating value-driven products has been transformative.

DotCom Secrets by Russell Brunson
In today’s digital age, understanding online sales funnels and conversions is essential for business success. This book taught me how to design and optimize systems that drive consistent growth and revenue—skills that have been vital in my software business.

The Death of Strategic Planning and the Emerging Strategy by Reed Deshler
This book reshaped my perspective on strategy and planning. It highlights how traditional approaches to strategic planning are becoming obsolete and introduces a more dynamic, adaptive approach to navigating today’s rapidly changing business landscape. It’s a powerful resource for any entrepreneur looking to stay ahead in a competitive world.

Beyond these books, I’ve also gained valuable insights from thought leaders like Simon Sinek, Naval Ravikant, and Seth Godin through their videos, essays, and podcasts. Their work complements the lessons I’ve learned from these books, offering fresh perspectives on leadership, innovation, and strategic thinking.

For anyone aspiring to grow personally and professionally, I’d say this: immerse yourself in books and resources that challenge your thinking. They’re more than just knowledge—they’re tools to reframe your mindset, solve problems creatively, and lead with purpose. These resources have been pivotal in shaping who I am today, and I continue to draw from their wisdom in my journey as an entrepreneur and leader.

Contact Info:

• Website: https://wesdomtech.com
• Instagram: gabrielosoriohenao
• Linkedin: https://www.linkedin.com/in/gabrielfelipeosorio/

Image Credits

No credits needed.