What 20 years of entrepreneurship taught me

15 years ago, I was starting my first company. And if I take last month as a reference, it is 20 years since my first venture. I feel very lucky to have found many records of this whole period. From photos, emails, notes, and many other things that helped fuel not only nostalgia and gratitude but reflections. Making this a humbling moment to ponder about how much my way of thinking has changed.

Needless to say, this is an essay centered on me. Unlike most of the time, I’m not trying here to generalize or aggregate different points of view. So, do not expect these to be a set of rules that may apply to you, but it’s just a way for myself to celebrate this moment, share my reflections about this arbitrary date and dump it on the web.

So let’s go

It’s my privilege

In general, less than 20% of companies survive their second year, for startups, this number is less than 5%. Most companies won’t be able to pay back the spent effort for at least 4 years (or ever). Being able to take such risk is a privilege accessible for very few in our society. Some may think that the drive to venture such a path is a matter of personality. But looking back, I can see clearly that it was not only a matter of actively taking the opportunities but also being enabled to do so.

Keeping a lean lifestyle

Even though my first venture may be comprised of voluntary work, none of the following were. Nevertheless, none of them ever managed to pay back the invested effort. Working on my own business, especially high-risk ones like startups involves taking a huge cut in my paycheck. On average, my cut around 75%, which means that if I had chosen to work in the market, I’d make 4 times what I was making. Since none of my companies reached an exit, IPO, or huge breakthrough, this difference never came back to my pocket. On the plus side, none of my business was closed on a loss. Which is a huge plus, since I know a few people who lost a good amount of money due to business debt.

Keeping a lean lifestyle and a good reserve was a key component of my life. Mainly because when the business fluctuates — at probably it will — your payment fluctuates as well. Once I went through six months without getting a single dime in my account. These uncertainties thought me to avoid living a large life and always keep my finance under conservative control. This was easy in the beginning, being a single teenager in my parents’ house. But as time went by and I grew up, more and more responsibilities piled up. Rent, marriage, children, and other costs accumulate and make it harder to live a life with plenty of slack. For sure, if I haven’t started early and kept until now, I wouldn’t be able to be running into the risks I’m into today.

It’s my choice, I shouldn’t complain about it

I don’t appreciate it when entrepreneurs complain about how hard it is. Be it complaining about the lack of help, to the hardships of bureaucracy, government, laws, market, or even to the lack of sympathy by society. As I told before, I see this path as a privilege and a choice, so I see no point in externalizing the blame. When things are hard I face them as the rules of the game, I can either act or just chose another game. It’s a solitary choice, and I accept it without delegating it to others. This has helped me always think about what I can do about the situation at hand, always assuming that if it affects me it’s my responsibility, no one else.

Appreciate the journey

Although the choice is solitary, my journey was always surrounded by good people. These were a big chunk of why I stayed so much time in each venture (my average is 7 years on each). A mic of luck and choice took par on it, making it key, not only for the businesses for my personal and professional growth. I had contact with extraordinary people, learned many different skills. I had many good and especially hard moments. I lived through a company breakup that thought me a lot about how team and principle alignment is a key component to move forward. I’m pretty sure It’d be very hard to be the professional I am today if it wasn’t for the richness of the journey I was able to walk through.

Accepting change

I consider myself a stubborn person but there were key moments when changing my mind proved to be very important. I was educated as an academic, in search of a single answer for every problem. But the uncertainties of life thought me that there is plenty of answers out there. I remember clearly not only when I was right, but when I was wrong. This thought me to embrace other people’s opinions with much more ease, even when they sound absurd. Today, I’m much more open to exceptions and to give a chance for new ideas. This paid back much often, especially when we’re talking about people and businesses.

I find this important because I feel successes compound exponentially while failure costs are usually incremental. Being stagnant feels safe, and proves to be in the short term. But embracing change is scary and unstable in the short term, but very profitable in the long term.

There’s no formula for your Yes/No

Common wisdom states that I should say more “no” than “yes”. And it’s about right. If I’d say “yes” to everything I would not have time to do anything at all. But, such a rule does not help me regarding “when” to say yes. Knowing this is as important, and I’m pretty confident there’s no way to know for sure. There were occasions when I was in the right place, but at the wrong time, or the other way around. But other times I was lucky to be in the serendipitous spot. The only way to know was to try it out. When it seemed to be working, keep on, if not abort.

Looking back, I can see a lot of these moments in my life. I got my first job because I had nothing to do during lunch and a friend invited me to visit where he worked. By the end of a hall conversation, I was hired. I started my current company because I and my co-founders managed to be transitioning from our previous companies at the same time. But not all goes well, I had many encounters and invitations to projects that I said no. Either because I thought it was not the time or because I did not saw the chance when it was presented. I try not to overthink about it, but to be thankful for how lucky I am and move on.

Closing

I have been a great journey. I could not picture myself as the entrepreneur kind, especially at the beginning of my life. Coming from a family that always valued stability, I always viewed the goal of a comfortable life as the default path. I’m very grateful for all the people that took part in my story, my co-founders, my co-workers, my friends, and especially my family. There is a lot more to come ahead, much more to learn yet.