About

Hi there! I'm Dui Toledo. It's great to meet you!

I'm a startup executive, a mix of CTO and COO, and I've led several US tech startups with tens of millions of dollars in revenue for the past 10 years.

You can reach me by replying to one of my emails or on www.linkedin.com/in/dui-toledo.

Thanks for reading,
Dui

Story

If you want to learn more about me, here's my story painted through my professional opportunities and growth.

My background isn't unique. I made several mistakes, got lucky sometimes, and did a few things right.

This makes my advice more applicable. You don't need to have been born in New York City or have gone to MIT to do what I did.

Books and their absence

I live in São Paulo, Brazil, where I was born and raised by two loving parents, neither of whom completed high school. My dad completed grade 7, and my mom grade 4.

Growing up, we had no books, like a typical Brazilian household.

I wasn't taught the habit of reading in school. Our teachers didn't assign books for us to read. When they did, no one even bought them.

The schools in Brazil don't provide students with free books, and we had to buy them ourselves. Money was always short. Why buy books we wouldn't read?

I had no access to libraries growing up.

There were libraries, but nobody I knew would go to them. They were unmaintained, and all books had to be in Portuguese, limiting the available titles.

By the time I finished high school, I hadn't yet read any books. Not fiction, not non-fiction, not even children's books.

Nothing.

College and libraries

I studied Computer Science at a local college.

I got my first video game console when I was 3, which awakened an interest in computers that never went away.

Despite that, I didn't know anything about programming computers until I went to college. I didn't know where to begin and knew nobody to learn it from.

We had dial-up Internet a couple of years before, but I used it mainly to chat online with people and play online games.

That all changed in college. I was now going to study Computer Science and have teachers who knew how to program and would teach me.

But going to college had another, much more significant impact on my life: I finally got access to a library with textbooks, non-fiction, and fiction, all in English.

Education and learning

To explain why access to a library was pivotal to me, I need to tell you about my education.

My professors weren't bad, but my education was terrible.

In Brazil, the majority of universities are private. They compete fiercely for students and have meager admission requirements.

The pace in class was whichever lowest common denominator allowed all students to follow them. Brazilian private universities sell commoditized degrees and must keep students from transferring or dropping out until graduation to maximize revenue.

With the library and its books, I could shape my education and pursue it at a much faster pace. For the first time, I had access to knowledge that wasn't what my teachers told me.

Books freed me from my cultural and economic educational chains.

First job and social skills

In my senior year, I got a full-time internship as a software engineer at the R&D labs of a multinational telecom corporation.

This meant that at 21, I was by far the most successful person I knew in person. I had an entry-level job in a high-tech company and was paid to do what I loved: programming.

They almost exclusively hired interns from the city's top public university, and I was one of the only interns not to come from there.

I got in because of the books I read.

Once hired, I committed every gaffe someone clueless about corporate culture could, including talking about salary with people I didn't know. I even came to work wearing a tank top shirt once.

Nobody I knew and trusted had gone through this before for me to ask for advice.

But books were a new trusted source of information. I even had money to buy books now.

I read books on getting your first corporate job, communication, body language, and anything else I thought could help me.

It wasn't quick: I was bullied as an intern, and between my internship and getting a full-time job offer, the HR manager at an IBM interview told me, "You got the job. But next time, dress appropriately".

But I could now use books to make progress when I got stuck and had nobody to help me.

Jobs with new technologies and models

Working at the R&D lab was exciting and challenging. I was progressing quickly and being recognized through awards and team lead responsibilities.

Internet programming was becoming more popular, but there was no need for it at a telecom R&D lab, so I started studying it through books in my own time.

A few years later, my then-girlfriend (now wife) had to move to a different city for her job, and when looking for a new job to move with her, I applied for a role focused solely on Internet programming.

The interview covered materials I learned through books, none of which I had professional experience with, and I did well. They hired me "even though you have no specific experience. We'll take a bet on you". My salary doubled.

This new job was at a health insurance company, the biggest in Brazil. I continued to learn much through books and to apply it to my work to progress quickly.

A similar job transition happened a few years later. I was learning new technologies and tried and failed to get our big company to use them.

This led me to a remote job in the UK at a small startup using those new technologies. I passed my interview thanks to my self-study, and they gave me a job "even though you have no specific experience. We'll take a bet on you".

I kept learning. My new coworkers' median talent and skill levels were now much higher. I was the worst person in the room, which gave me new benchmarks.

After a long history of bets others made on me, I now had access to great models.

From Engineer to CTO and COO

I had the opposite of entitlement: the feeling that I didn't deserve it, that life was generous and kind to me, unlike everybody else I knew. I was fortunate.

This gratitude made me easy to work with despite my cluelessness at things I had no business doing. Being easy to work with and a quick learner in a small startup meant many opportunities.

I now had models, feedback, and books as sources to get out of confusion and into competence, given enough time and effort.

I started getting more disciplined about how I spent my time, optimizing my productivity during work hours and learning after hours.

Eventually, I was offered a position at a startup to join the co-founders as their first engineer. This was the first job I got that wasn't a bet on me: I was good. By then, I had ten years of professional experience. There was no interview.

The company grew and succeeded thanks to everybody's hard work and some luck. I was offered more responsibility thanks to the trust I built to step up to new challenges and grow, and I was the obvious choice for new opportunities. That was my first CTO job.

Everything changed when my father had a hemorrhagic stroke. With my newfound personal responsibilities, I struggled to manage my leadership role in a growing and successful company.

I left my leadership position and decided to work as a software engineer again. Way overqualified for the jobs I applied for, I cruised through interviews and chose a great company to work for.

For the first time in my professional career, I was betting on my employer more than they were on me. By then, I had 12 years of professional experience.

I needed to learn new technologies and picked them up quickly. One of my first messages in the company Slack was, "what's a good React book?" to which the reply was, "one of our colleagues wrote the book on it." I was again lucky to have access to unique models.

My father passed away about eight months later, and I soon got new responsibilities as the company grew. We were hiring a Director of Engineering, and once I was available to take the role, I again was the obvious choice for it.

At this point, I was reading books frequently, almost constantly. Luckily, the books on management, leadership, project management, product management, collaboration, and software development were numerous.

Since then, I went back to my previous company for a year and oversaw new departments like Product, Customer Support, and Marketing. Then, I returned as COO and managed People Operations, Business Operations, and Finance.

In summary and next steps

The theme is using books and self-study to get a relative edge in skills as a gateway to opportunities I would otherwise not have access to.

Books today are more accessible than ever through online bookstores and libraries. Remote work has created numerous new professional opportunities, no matter where we live. We spend much of our time online in ways that can be spent more purposefully.

We have an unprecedented opportunity to grow and use our skills.

I hope sharing this story and my writing with you helps you do it.