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How to start your chess business – meet CEO of, a successful start-up story

Outpostchess is an awardee of 3 prestigious accelerator programs: Raising Starts, SmartStart, and Katapult accelerator. Feel the story inside, and learn chess from one more angle – the business one. Get inspired on how to start your business from the CEO Lena Miladinovic and visit Outpostchess app here

A word from CEO

Hello, my name is Lena Miladinovic. I am the Founder & CEO of Outpost Chess. I’m a professional titled chess player (WIM), coach (FI), arbiter (IA) and organizer, 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 start-up 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. Anyway, chess business is a new angle for me, I found it so interesting, wish you can join my venture by signing up!

Company Name: Outpost Chess Location: Belgrade, Serbia Operating since: 2021 Website: Socials: @outpostchess (Instagram), @OutpostChess (Twitter), follow us for up-to-date information about Outpost

About the company

Outpost is a digital and interactive chess platform that connects chess professionals (players, clubs, organizers, arbiters, coaches, streamers) where they can easily find, engage and pay each other. This will speed up communication, transactions, and enhance the organization of any kind of chess event. Chess people will finally have chance to monetize their chess skills.

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

We are currently focused on tournament organizers. With Outpost Chess, tournament organizers can now effortlessly create and manage chess events, from player registration and fee collection to award pay-outs, all in one streamlined digital platform that takes their organizing experience to the next level.

Features – Hmm what is this platform for?!

Create a profile – represent yourself in a specific chess way, be visible so you can be enaged.

Blog – write a Blog, keep record of your chess life, be popular!

Wallet – Receive payments and awards via Outpost payment service

Intelligent Search – Find your chess bodies: players, clubs, organizers, arbiters, trainers, streamers and get in touch so you can explore more options in the chess world!

Tournament Calendar – Find or Create your own tournament in our 1000+ tournaments’ base

Inbox – talk to your friends, connect to GMs

Registration – register for tournaments and pay participation fee in a smooth way

…and many more, feel free to explore –

We are hiring and thrilled to have You, get in touch

Team behind the idea

Besides me as a Co-founder and CEO as well as WIM, IA, FI in chess, there are 4 more key Outpost players here:

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 :) He also traded banking system for the chess world.

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

Maja Borkovic as a Social media manager, with Outpost Chess from the day 1, engaging with the chess community daily which is priceless for Outpost. She is that big secret behind our profiles 😉


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.

Lena’s Biggest obstacle

Leaving ego aside.

Future plans

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. Outpost is an awardee of 3 accelerator programs: Raising Starts, SmartStart and now Outpost is one of the Katapult accelerator awardee. This program will match our next (seed) round from 50K to 300K in EUR with no equity taken, which make us pretty investible. Schedule a call with us to find out more:


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. Step by step. 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


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