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Broken Glass and Eight Attempts at Pregnancy

Gabriela Rosas shares two stories of resilience, launching a business in México and motherhood.

By:
Fuckup Nights
September 24, 2025
Gabriela Rosas shares with us her story of failure

This month's story is unique. It was part of one of our most memorable corporate events in 2025: a special edition with BBVA Bank to celebrate motherhood.

On that occasion, Gabriela Rosas stood in front of nearly 500 bank employees (and now in front of us as well) to tell not one, but ttwo stories connected by the same thread: persistence.

‍Stories that range from thefts, vandalism, a kind of "Hunger Games with the government," to eight attempts at in vitro fertilization. Stories with very different outcomes, but with the same lesson that Gabriela decided to share with us.

This story was first featured in our newsletter Speakers Stories, where every month we share one of the best failure stories from our global community. Be the first to receive these stories in your inbox—  subscribe to our newsletter here.

Who

Gabriela Rosas is the mother of one child and stepmother to three. She has spent over 10 years focusing on working with startups and technology companies, particularly on launching foreign businesses into Latin American markets. She's passionate about coachingand working on the human "being" to achieve results in demanding corporate environments.

She currently works with women and men in leadership positions as well as with couples dealing with fertility issues or doubts about parenthood.

Defining failure

FuN: What is your personal definition of failure?

Gabriela: It took me several years to distinguish "failure," because I grew up with the idea that failure or being a failure was directly related to who you were — whether you were or weren't a loser. However, today my favorite definition of failure is: the distinction between a desired outcome being achieved or not achieved, period.

FuN: What was everything like before the failure?

Gabriela: I worked at a lovely company called Hotel Tonight. Part of my job was to go to hotels, stay in them, and negotiate deals with hoteliers. It was a lovely life.

At some point, Airbnb acquired the company, and that made me reconsider the next step in my career. That's when someone reached out and asked me to do what I'd done at Hotel Tonight for Bird: bring the business to Mexico.

It was a company I found extremely sexy, with a very innovative model, and both the company and the brand were on everyone's lips. Their business was electric scooters — the ones you can rent with your phone on the street.

For me, it was a challenge to go from that world of luxury hotels and cocktails to working with mechanics and spending hours in parking lots.

One thing you should know about me is that I get myself into trouble like that. I get excited about projects that sound innovative, disruptive, or strange, and I want to see how I can participate.

Making a parenthesis: on a personal level, at that time, I had a passing little doubt about whether or not to be a mother. And even though it popped into my head now and then, my doctor reassured me, saying I had until my 40s to try. At that professional transition moment, it didn't seem like a near-term problem.

The real F*up 💩

Gabriela: I was responsible for absolutely everything related to Bird's operations in the country and Mexico City, the most important one. Although we started with a great attitude and all available resources, we didn't anticipate the many challenges we would face along the way.

To begin with, Mexico City had just undergone a government change, and the new person in charge of mobility came up with a Hunger Games–style model to grant permits.

With more than eight scooter and bike companies operating, they launched a competition to reduce the number of companies to only two at a time. Whoever was willing to put up to 800 scooters in circulation and pay more per scooter would win.

Those were weeks of biting our nails and waiting. Although we had lost by a few cents, one of the companies didn't pay, and we managed to obtain the permit.

But despite that victory, things kept happening. If it wasn't the permit, it was theft by a criminal organization that resold them or even by our own mechanics or "birdwatchers," the attendants.

I would spend hours late into the night tracking scooter movement, trying to figure out who on the team was sabotaging us.

Even during the protests that often happen in the city, people used our scooters as weapons to vandalize shops.

I began to feel paranoid, and I remember a couple of occasions when I burst into tears in front of the team, even though I didn't want to be the dark cloud, and tried to swallow my emotions. A disaster!  

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FuN: How did this experience shape your future coaching work with leaders who deal with fertility and parenthood issues?

Gabriela: My experience with Bird has a parallel with the story of my own motherhood: everything was against me.

When I finally started trying to get pregnant, thanks to other doctors, I realized I should actually have tried before 35 and not at 40, as the first doctor had told me.

I was already 37 and had an army of doctors telling me I would never be able to get pregnant. Also (I tell you, I like getting into complicated things), my husband already had three children and had had a vasectomy that, despite being reversed, didn't work.

Now, the only alternative I had to get pregnant was through in vitro fertilization. For me, this felt like a failure of being, of identity— something that your body is supposed to be designed to do. It was an emotional roller coaster.

Honestly, I wanted to give up on each of them, both at Bird and in my desire to be a mother. I thought those were worlds I could handle with strength, money, and resources, when in reality, it was necessary to take a step back and use both head and heart.

I had to go against what doctors knew from studies and statistics.If there was a one percent chance of getting pregnant, I decided to stand in that one percent.

At Bird, everything was wrong, but we focused on that small window where we could make a difference, and with that, we managed to be in the company's top ten cities.

From that point on, I decided to make a difference to help many women avoid going through everything I experienced.

FuN: How did these parallel stories end?

Gabriela: Bird died. The big-fund bubble (like SoftBank) burst, and many companies, Bird among them, decided to withdraw their operations from markets where they weren't profitable.

And regarding my commitment to becoming a mother: despite trying for a pregnancy at 36 (which to the world seems crazy), after eight cycles (that is, attempts), four clinics, three years of my life, and more than a million pesos, my son is alive.

Sometimes it's easier to give in to "what you already know or believe to be true" and decide to quit. In the end, there's something wonderful in learning to navigate the unpredictable.

At some point, I got used to failing. But as long as you befriend failure and say, "I'm going to fail 500 times," and in the end you fail only 250 times, that's already a win.

In conclusion…

  1. Failure is not identity; it's an outcome: Failing does not mean being a failure. It only means that in that moment and in that way, the expected result wasn't achieved. Separating who you are from what you achieve opens up the possibility to choose: Will you try again? What will you change along the way? What will you do differently next time?

  1. Counterintuition is also a muscle worth training: Many times, the most effective thing is what seems to go against immediate common sense. Daring to decide from counterintuition, even if it seems illogical or risky, develops the ability to find creative solutions and to discover opportunities where others only see obstacles.

  1. Navigating the unpredictable is a way to build resilience: Life and projects are never linear. Learning to stand firm in uncertainty, to adapt, and to keep moving forward without guarantees strengthens character and builds resilience. True strength is born from daring to walk even when the path is unclear.

Connect with Gabriela!

On Linkedin

‍On Instagram

‍On its website

Remember, our channels are open for your questions, complaints, feedback, or collaboration at: rich@fuckupnights.com.

Edited by

Ricardo Guerrero

Edited by

Ricardo Guerrero

Broken Glass and Eight Attempts at Pregnancy
Gabriela Rosas
Co-Founder @ Cascade Leadership | Business Ontological Coach | Former General Manager at Ipsy Mexico, Bird Mexico, Airbnb/Hotel Tonight
Experienced General Manager and Certified Ontological Coach, with over 10 years leading international business expansion, launching US and global startups in México and LATAM, and building high-performance mission-driven teams.
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