A 17 year old in Microsoft Imagine Cup: My story and what I’ve learned

Sergio Mattei Díaz
4 min readJul 27, 2017

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Photo creds the awesome photographers @ Microsoft

Two months ago, I woke up early for some errand I needed to run, and taking a look at my phone, I noticed there was an email regarding an application I made to Microsoft Imagine Cup with my project, Taleship. For a second there, almost disregarded the email — I thought it was a newsletter, since I didn’t expect results from the application. But something told me to open the email, maybe check it out.

I was selected for a second round for the Latin American Online Finals, and would have the opportunity to pitch my project to a panel of 3 judges. A few days later, I pitched them the idea and after a session of Q&A about the project, I was told I’d be notified the next day if I made it.

That quickly became possibly the longest day of my life so far. I did not sleep at all that night because of the nerves! Nearing two PM, I received a call from a seemingly unknown number; and lo and behold, I was told by the contact at Microsoft that I’d be going to Seattle! I jumped of joy with my grandparents who happened to be nearby.

Over the course of the following months, I would train with the great folks at Microsoft Puerto Rico to improve my public speaking abilities, fine tune Taleship to maximize scalability, and plan ahead on how my startup would unfold. Mentored primarily by the dream team consisting of Yamille Moralles, Ricardo Vila, and Ernesto Morales, I managed to improve the way I presented Taleship and pitched. Also, due to a note by Sharon Minelli (thanks so much!) on the Puerto Rican newspaper El Nuevo Dia, Taleship grew the userbase exponentially, preparing it even further. It was truly a life changing experience, and led me to meet some incredible people I look forward to working with sometime!

The final week came, and I left to Seattle to the Imagine Cup to represent my country and Taleship! I arrived at Seattle and everyone was very welcoming. I got to meet some amazing friends I will keep in touch and work with in the future. I got to Quarterfinals. I didn’t win, but the experience of just being there was incredible.

Here are some takeaways from my experience that I will definitely hold close to any competition I go to next.

  1. Say hi. A simple hello and a smile can take you places. Awesome places. And it will lead you to talk to some of the most brilliant people you will ever meet, and definitely make new friends. It doesn’t hurt, so when going to Imagine Cup or any community event where there’s a chance to meet people, just say hi. The worst that can happen is, well, not talking.
  2. Keep in touch. The next tip would be to add everyone you meet on social media and stay connected. The contacts you make in these events are invaluable not just as great friends, but as experts in their fields that might be able to help you sometime (and you help them too!). Even if you don’t win the event, the biggest takeaway you will have is the people you meet and the things you learn from them.
  3. Practice your pitch. Preferably in front of big crowds. I did not practice much with crowds, and it reflected in how I delivered and my nerves. Anything with practice becomes better, so practice in front of many people and you will be very fluid.
  4. Have a plan. Always have a long term plan for your startup and how you want to scale. And mention it too. These competitions want to invest in people with vision. One of my mistakes was I did not have enough time in my pitch to mention my plan, and forgot to explain how I planned to monetize.
  5. Just have fun! If you don’t pass a round, you will be naturally bummed. It’s normal, and part of the process. But just go and have fun then with the people you met! Go talk with them or play a board game or something. The fun I had with the people I met is something I will never forget.

Those are the biggest takeaways I had from this competition, and I hope these are useful for your next competition experience. This was a brief of my Imagine Cup experience representing Taleship, and I hope you love this article.

Shout-out to the incredible team of people I got to work with: Jonathan Agosto, Maria Luna, Mabel Geronimo, Carlos Rojas, Mariano Amartino, the ones I mentioned in the article, and my parents of course. You guys rock.

Also, another quick shout-out to the fellow competitors at Imagine Cup 2017, you guys absolutely rock! Can’t wait to see your projects unfold.

That concludes my latest article on Medium! Follow me in these sites to stay updated: Taleship, Twitter, GitHub, Portfolio

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