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In entrepreneurship and life, I’ve learned that sometimes the most courageous act is letting go.

I founded my first successful startup when I was 39 years old, after trying my hand at five other ventures.

I remember multiple times along my entrepreneurial journey, looking at my situation and thinking that there was no way out. And it is in those moments when you are truly at the bottom, that you find a way forward.

There’s a scene in an old mountaineering film, Vertical Limit. This father, his son, and his daughter fall off a gigantic mountain and are hanging from one rope. They quickly understand that the rope won’t hold the three and that if they don’t do something, everyone will die. The father at the bottom asks his son to cut the rope to let him die, and, in doing so, allow him and his sister to save themselves. The son cuts the rope. He and his sister survive. 

Vertical Limit
The scene in Vertical Limit right before they cut the rope.

As an entrepreneur, I’ve faced my share of “cut the rope” dilemmas.

Six months into the launch of my fifth start-up “Imperdível” (a Groupon-type site), I came face to face with a harsh reality: our business model was fatally flawed. With both client quality and customer experience out of our control, there was nothing we could do to salvage the venture, even after pouring in most of my savings and borrowing additional money from my father.

We had 100 employees, we were earning millions per month and it seemed like we had the best business in the world in our hands. It was a business model that I believed in 100% when I started. I convinced investors, partners, and my family that it was the way forward. I put all of my time, effort, and belief into this business. But, suddenly, after all of that work, it was just over?

Paulo in front of the Imperdível logo.

The day I realized this, I went home and sobbed in the shower.
I cried and cried.

The burden of disappointment weighed pretty heavily on my shoulders. I felt I had disappointed my family, my partners, and my employees. I felt awful.

The next day, I talked to my partners about liquidating the business. They refused to do it — “It’s still too early to throw in the towel! We barely started!”. But there was no light at the end of our tunnel. With zero faith left, there was nothing I could do to get unstuck, except to shut down the business or sell my share and move on. I did all that I could do, and at that point, I had to cut the rope.

And there I was: 39 years old, two young daughters, and not much money left. I had to start over from scratch.

My wife offered to support the home while I got back on my feet. Summoning the courage to start over required me to understand that while I had bet on the wrong business model, the business was what failed, not me. There was no time to ruminate about what it could have been, no looking back.

Inspiration came in 2012, while I was mentoring two entrepreneurs on their business plan. They were pitching a company that didn’t have much growth potential, but I saw potential in the entrepreneurs, Ariel Lambrecht and Renato Freitas. We began brainstorming ideas to improve their business. And it was there, that the idea for 99 Taxi came along, which would become the biggest Brazilian e-hailing app.

99 Founders 1
Paulo, Renato Freitas and Ariel Lambrecht.

We launched in August 2012, starting as a taxi-and-rideshare service. After six initial slow months, we suddenly started to grow a lot. In our first year we already had 25% of the total of taxis in São Paulo available in the app, and growing up to 50% per month in number of rides and passengers. There was no point in trying to set a goal because we would put a ceiling where there should be none, only the sky. So, the most important thing there was finding the path to sustain growth.

By 2015, we closed a big round and finally had some money to compete with Uber, which got to the country in 2014. It was a perfect year for 99. We started the year with around one-third of the market share, and we ended the year with more or less two-thirds. 99 hit its first million rides through the app. Everything was going incredibly well.

And then a threat came that could have destroyed everything.

An unscrupulous financial coup took place. While a legal settlement prevents me from disclosing details, it was such a threat that my entire business was at risk of going down, or not able to fundraise for years until the issue was sorted out. This was my sixth startup, and it was an exceptional one. I was not going to let this happen. 

99 Team
Paulo with his daughter and the 99 team.

I never wished anything bad on anyone, but there I was, in the depths of my rage, wishing that this unscrupulous person would get hurt or sick — a visceral response born out of pure indignation. Anger boiled within me like a poison eating me from inside. And while this anger ignited my determination to fight, the truth is that the intensity of my fury was overwhelming. This rage consumed me day and night. I couldn’t believe the first time I had a successful company in my hands, it could all be gone because of someone else’s evil intent. I let the anger consume me like I had never let anything consume me in my life.

And then, suddenly, when this situation was still unfolding, the world stopped.

It was August 2015, and I was sitting at my doctor’s office.
The diagnosis was leukemia.

And there I was again, hanging off of the cliff bound by a rope that was about to snap. The anger was weighing so heavily on me. It was such a heavy feeling that I could not cope with it. I had to cut the rope and let go of that anger, or myself and everything I had worked for would be done.

Cancer was not going to stop me from fighting. I mustered up all of my strength to hold onto the rocks and climb my way up. I had no more safety net. If it didn’t work out, it would be a free fall. But I would find my way back to the top of the mountain.

99 Founders 2
Paulo and his co-founders.

I worked relentlessly from the hospital to ensure the business stayed afloat. We signed our Series B round from there. I was undergoing treatment and holding meetings with everyone via Skype, while my two co-founders came to visit once or twice a week.

Looking in hindsight, I bet my cancer was the psychosomatic result of that anger episode that consumed me alive. To this day, when my wife sees somebody holding a grudge, she says: “watch out because anger gives you cancer”. I believe she is right.

The culmination of our efforts materialized in the form of monumental achievements. We eventually got the approved regulations for private cars in São Paulo, and later other cities in Brazil. We became the only company in Brazil that had a complete mobility portfolio, you could choose whether you wanted to use a taxi or a private car.

In 2017, we closed the largest round of venture capital in the history of Brazil, with investments from DiDi and SoftBank. One year later, we sold 99 to DiDi and went on to become Brazil’s first unicorn.

99 Unicorn
Paulo and his co-founders celebrating becoming the first unicorn in Brazil.

Reflecting on the trials and triumphs of my journey, one lesson stands out: tomorrow is always another day. I thank the entrepreneurial mindset for getting me through some of the toughest challenges in my life and pushing me to keep thinking ahead.

And should the time come when I have to let go once again, I’m not going to hold on to the point of destroying myself. Holding on to resentment, holding onto things that weigh you down, will consume you in a way that will unbalance everything. Sometimes you have to let go of these heavy things to find the
way out.


Paulo Sig