Learning from Startup Leadership Failure: A Career Pivot Story
In this edition, we explore startup leadership and career reinvention through the experience of Federico Gómez, former VP and General Manager at PayPal LATAM, who left a corporate career to navigate chaos, misalignment, and unexpected lessons in the startup world.
This story was first seen in our The Failure Institute Newsletter, where each month we share one of the best failure stories from our global community. Get these stories in your inbox before anyone else—subscribe to our newsletter here.
About Federico Gómez
Federico has dedicated his entire career to operating and scaling companies in financial services and Fintech areas. He mentors entrepreneurs and advises investment funds. His most recent position was VP and General Manager of PayPal LATAM.
Learning from startup leadership failure is something I never expected would define a key moment in my professional journey. My experience—leaving a stable corporate job for a chaotic startup—completely changed how I view leadership, decision-making, and failure.
Defining Failure
The Failure Institute: What’s your personal definition of failure?
Federico: For me, failure means not achieving the goals you set for yourself.
Why I Left a Global Corporate Job
Taking the Risk: From AMEX to Startups
After graduating university, I joined American Express in Mexico. It was the beginning of a promising corporate journey. I worked on global projects and eventually transferred to the New York office. Life was stable and filled with prestigious opportunities.
Still, I couldn’t ignore what was happening in Silicon Valley. Startups were challenging the norm. I felt drawn to this world. When a startup in Mexico offered me a leadership role, I took the risk. I left behind a global career to chase impact and growth.
The traditional corporate lifestyle was no longer fulfilling.
💩 The Actual Failure: Misaligned Startup Leadership
Initially, I found the startup world refreshing. I contributed to fundraising and built new products from the ground up. I saw how quickly startups could adapt, something rare in corporate settings. We were helping underserved communities access affordable financial tools.
But learning from startup leadership failure soon became a reality.
I began to notice severe cultural mismatches. The leadership, centered around the founder, didn’t align with my values. I believe leadership should be earned, not enforced. We lacked focus. We were juggling too many priorities with no discipline.
I hadn’t taken the time to research the founder’s background or understand the company’s internal culture.
When Leadership Styles Don’t Align
Conflict and Chaos: The Turning Point
The wake-up call came during a critical three-year planning meeting. Tensions exploded between executives. One quit mid-meeting. That moment exposed how misaligned the leadership team truly was.
I had left a stable global career and moved my family from New York to Mexico for this. The failure felt overwhelming.
Fortunately, being back in my home country surrounded by loved ones gave me the emotional support I needed to navigate the setback.
Getting Unstuck and Moving Forward
Rebuilding and Reinventing Yourself
Despite the misalignment, I still enjoyed working with the broader team and clients. I didn’t quit right away. Instead, I started looking for a new opportunity.
Eventually, I accepted another role that allowed me to keep growing. Months later, PayPal offered me a leadership position to launch a new market. My experience in that failed startup helped me land the role.
Lessons Learned from Startup Leadership Failure
If I could go back, I would’ve invested more time understanding the founder’s values and the company’s culture. I would’ve sought references and examined how others had fared.
Still, I don’t regret taking the risk. The experience taught me lessons I wouldn’t have learned in a corporate environment. Those insights still shape my decisions today.
In Conclusion…
This experience was filled with unexpected turns, but also with valuable takeaways that continue to shape my professional decisions. Reflecting on the journey helped me identify the insights that I now carry into every new role and challenge.
Don’t forget:
Always research the company’s culture, leadership style, and founders before committing to a new role.
Leaving your comfort zone can lead to unpredictable results—but also to powerful personal and professional growth.
Even after setbacks, your skills and experience remain valuable assets that open new doors.
It’s never too late to redirect your path and find opportunities that align with your values.
Sometimes the toughest failures hold the seeds of your next big opportunity.
Failing in a startup taught me lessons I couldn’t learn in a corporate job. The most important one: every experience—good or bad—helps you grow and move forward.
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