Lena Miladinovic



Hello, my name is Lena Miladinovic. I am the Founder & CEO of Outpost Chess.

I’m a professional titled chess player, coach, and arbiter, and I have been living in the chess world for more than 20 years so far. I was a multiple youth champion of Serbia, and a World and European University chess champion. I represented my country multiple times in European and World chess championships. My huge chess experience enabled me to see [the gaps] in the chess world which inspired me to start a new chess project and become CEO of a startup company (Outpost Chess).

I finished my education in the Faculty of Political Science. My Master's degree is also Political Science but here I am in the entrepreneur world. I love playing chess but my [other] passion is also a sport with a ball - like soccer, basketball, tennis, volleyball, etc.


Company Name: Outpost Chess

Location: Belgrade, Serbia

Operating since: 2021

Website: outpostchess.com

Socials: @outpostchess (Instagram), @OutpostChess (Twitter)


Tell us all about your company. What services do you offer?

Outpost (SaaS) is a digital and interactive chess platform that connects chess professionals (players, clubs, organizers, arbiters, coaches) and where they can easily search and find each other. This will speed up communication, transactions, and enhance the organization of any kind of chess event.

In short words - Outpost is “Linkedin for chess professionals”, where they can make personal profiles, represent themselves, connect with other chess users and organize their chess lives much better by virtue of the specific chess features Outpost offers. Chess professionals will finally be visible and fully engaged in the chess world.

Tell us a bit about your co-founders.

Ilija Dragisic - COO - He has been in business for more than 15 years. He has two active companies and one of them is a start-up; hence, he is my mentor through this entrepreneurial journey. He loves to say that he is a passionate entrepreneur, eager to make a business that will change the game.

Dragutin Miladinovic is our CTO, and also my big brother, who helped us improve our development side. He is enthusiastic about making innovations with his own hands :)

Matt Thomas is our CMO, he was a chess-boxing champion in 2018. He is also an influencer and a serial entrepreneur.


What was your mission at the outset? Was there anything in particular that inspired you to start at the time you did?

My chess life inspired me. Through 22 beautiful years and my childhood in chess, I've learned a lot about this specific wonderful world, but I also saw what lacks. As chess gave me everything, I decided to give my best to empower chess by transferring the traditional into the digital world so these beautiful people can connect worldwide. The 21st century is the best timing to start a tech company, also the well-known TV show - The Queen’s Gambit - seemed like a momentum to start.


Growing up, did you always intend to start your own company/organization?

I did. I did know where - in the chess world, but I didn't know when, and didn't know how, but learned through the process. The magic is in the process.

How have your past personal & professional experiences helped you to run your company?

As I am living in the chess world, that helps [to show me] how should my business act. My management skills and previous experience in being a manager are helping a lot in managing and organizing my team and our tasks.

What is the biggest obstacle you've had to overcome? Leaving ego aside.


What's your definition of success? Do you consider yourself a success? If not, when will you?

I would say that I am succeeding. It doesn't matter If some project fails/succeeds, the true point is in the process and the things you are learning on your way "there". I've learned a lot and the feeling is great. Learn, learn, learn and you'll be ready for either your 1st or 5th project to succeed. The point is that you are feeling great by doing it.


Have the women around you helped you to rise? How?

Yes. My mom and three sisters have been supportive from the moment I become conscious till now and hopefully forever. :)

What are some of your future plans? Are you working on anything else right now?

I keep on spreading my contacts in the chess world, so I can learn about market size and chess people's needs. I have no current plans except Outpost and chess activities. We are in the funding phase right now, so the focus is on fundraising and growing Outpost.


What advice would you give to a woman starting out in your industry or starting her own company/organization?

Just start. We'd never have the perfect time or momentum - you can never ever organize things that much ahead. Just start and do things on your way. Even though I am a chess player who thinks a lot ahead, this is a particular situation where you should just jump in and swim!


Describe yourself in ONE word. Enthusiastic

Complete this sentence: "To be a girl or woman today is..." a pride."


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