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Gabriel Engel is the CEO and Founder of Rocket.Chat, the leading open-source team communication platform that allows users to chat securely on the web, desktop, or mobile. Previously, he founded four other businesses, including Konecty, a CRM focused on facilitating the management of any business process, and Intelimen, an agency.

Gabriel is a very special person to me and I’ve had the honor of partnering with him a few times. We talked about Gabriel as a founder, a leader, and a CEO who raised a $19MM Series A. Also, we went deep on his personal story and how his father mentored him to become who he is. Besides, we talked about technical topics such as open-source as a go-to-market strategy and all the typical struggles that an early-stage entrepreneur would go through as he built his empire.

In this episode, I asked him:

  • After you entered college in 1998, you started to work at your father's company. There you created Agrol, a portal about agribusiness. How did that first experience as an entrepreneur change you?
  • Agrol was acquired by Grupo RBS, which is huge in Brazil. Then, you could be hired there. Yet, you decided not to, and choose to, because you wanted to be an entrepreneur. Was that an easy decision, or did you fear choosing a different path from working at a big corporation?
  • During your early days as an entrepreneur, you were working with your father. How important was he to the beginning of your career? Besides, you were mentored by people such as Sergio Pretto, founder of Nutec, a software company that later became Terra, a web portal that played a key role in the early days of the internet in Brazil. Who were the mentors who guided you back then, when there was no playbook on how to build a tech company?
  • After selling Agrol, you gathered two friends from college and started Intelimen, an agency that developed websites, applications, and enterprise server solutions. How was your experience bootstrapping an agency that provided such services in 2001, a time when a huge chunk of the Brazilian population didn't even have internet access?
  • In 2004 you moved to London. There, you sold the agency you founded years later and worked as a developer at local companies. How was your decision to move there?
  • During your 6 years in London, you build a life there, worked as a freelancer and at companies such as Vodafone. Eventually, you got fed up and quit your job to build another company. Why?
  • At this stage of your journey how already had multiple companies, projects, and vast experience. So, the mentors and books who guided you then probably weren't the same who guided you when you started. Who helped you the most at this stage of your life?
  • In 2011, you founded Konecty. At that time, you were way more experienced and working at tech for more than a decade. What did you do differently in the way you managed yourself as a founder, managed people, thought about strategy, etc?
  • When you were young, you wanted to grow up to become an “inventor”. Back then, you learned that creating a company was the best way to get your inventions out into the world, so you have been inventing things and starting businesses to turn them into products ever since. When the idea for came along and you started it as a side-project from Konecty, was it clear to you that it could be your greatest invention and your Ikigai, or was it just an "invention" idea like any other?
  • You decided to make open-source. Did you fear you could be making a mistake by not following the tech entrepreneur playbook in this sense?
  • For a while you ran Konecty and at the same time. When was the moment you realized could be huge, and not just an idea you'd pivot later?
  • In your early days, Sid Sijbrandij, co-founder of GitLab, made an offer to buy Why didn't you sell?
  • Besides Sid, throughout your journey, you met high-profile people such as Eliot Horowitz, an early investor in Duolingo and Groupon, and Harry Weller, founder o MongoDB. Which are some of the lessons you learned from them?
  • How do you manage to dedicate time to spend quality time with your family and play with your kids?
  • What does the future hold for you and