Community Highlights: Meet Ilija Dragisic of Outpost Chess

Today we’d like to introduce you to Ilija Dragisic.

Hi Ilija, so excited to have you with us today. What can you tell us about your story?
I started my career early, during college. Since I was studying marketing and graphic design, I launched a branding agency in 2005. I was attending classes and handling client requests during the breaks. This experience allowed me to work with a wide range of brands—both small companies and major ones like Coca-Cola, the United Nations, Swisscom, and Tetra Pak. Because branding services are usually done at the early stages of a company’s journey, I had the opportunity to learn about many different industries, niches, and the specific challenges businesses face when entering the market. That agency is still operating today.

In 2013, I became one of the founders of the Association of Young Entrepreneurs of Serbia and served as its president for six years, until 2021. I’m proud of this organization because we managed to gather more than 100 companies whose founders were 30 years old or younger, and the association continues to grow each year. I can say that the initial mission has been achieved.

In 2015, I founded my first startup, Buildcon, together with my high school friends. We reunited after college and became interested in construction tech thanks to a friend who worked in the industry. Buildcon became the second startup from Serbia to receive investment from 500 Startups in San Francisco. We still operate this product, and over time, the company has expanded its expertise into logistics as well, helping companies from these industries build digital products.

Outpost started purely from my passion for chess. I love the game, and my co-founder Lena is a former University World Champion. She often talked about the challenges chess players face when trying to find clubs or tournaments—and the challenges tournaments face when trying to find players. So we decided to build a platform that could bring the entire chess community together and make communication easier. Outpost has since evolved into a gaming platform and an AI learning hub where players can play, learn, and even earn from their chess skills. Our goal is to keep people engaged with chess and help them grow.

Would you say it’s been a smooth road, and if not what are some of the biggest challenges you’ve faced along the way?
Hah, from my experience, there is no smooth road in business; you need to learn every day and to adapt quickly. I guess the hardest part is to start, but for me, this is the most interesting, to build something from scratch. At each start, it’s important to define the idea what you would like to do and how you would like to do it. After this, you need to figure out who will help you along the way. These three puzzles are important to match from the beginning; of course, it won’t be perfect with each piece, then adaptation to the new circumstances comes into play. However, if you do those 3 right, usually you’ll find the way to get things going, to make an early traction, fundraise, and to push your idea to the next phase.

As you know, we’re big fans of Outpost Chess. For our readers who might not be as familiar what can you tell them about the brand?
Outpost Chess is a modern gaming and learning platform built for the global chess community. We started with a simple idea: chess players around the world struggle to find clubs, tournaments, and opponents, while organizers struggle to reach players. We wanted to solve that and create a single home for everyone in the chess ecosystem.

What we do today goes far beyond that initial idea. Outpost combines competitive play, AI-powered learning, Chess Puzzles, and community in one platform. Players can compete in skill-based challenges, analyze their games with advanced AI tools, train with their personal AI coach, and join a community of people who share the same passion. It’s a platform where you can truly play, learn, and earn from your chess skills.

We specialize in making chess more accessible, more engaging, and more rewarding—especially for the new generation of players who want more than just a board and timer. What sets us apart is the blend of gaming mechanics and serious training tools. You can play fast games for fun, but you can also dive deep into interactive AI lessons, game reviews, puzzles, and personalized recommendations designed to help you improve.

We’re most proud of the fact that Outpost brings together players from over 90 countries, including complete beginners, experienced club players, and even titled professionals. It has become a place where anyone can feel included, motivated, and supported on their chess journey.

For readers, I’d highlight this: Outpost is more than a chess app, it’s a platform built for real progress. Whether you want to get better at chess, enjoy more competitive play, or find your community, Outpost gives you the tools to grow. It’s designed for people who love chess and want to get the most out of every game they play.

What has been the most important lesson you’ve learned along your journey?
The most important lesson I’ve learned is that choosing the right team and colleagues at the very beginning matters more than anything else. Early-stage companies live or die based on the people behind them. If the team doesn’t have the drive to grow, solve problems, and push through obstacles, the company simply won’t take off. This is the trickiest part of building a business, and it requires a lot of attention, honesty, and transparency from day one.

To avoid misunderstandings and maintain momentum, it’s crucial to define roles, expectations, and terms as early as possible. Clear agreements remove noise, prevent frustration, and help everyone stay aligned around the mission.

Today, with the help of AI, it’s even easier to get an unbiased, third-party perspective when drafting fair terms, evaluating contributions, or structuring agreements. That objectivity helps ensure that everyone on the team feels respected, motivated, and confident in the journey ahead.

Contact Info:

• Website: https://outpostchess.com
• Instagram: /outpostchess
• LinkedIn: https://www.linkedin.com/in/ilijadragisic/

Image Credits
Natalija Miladinovic
Raising Starts
Outpost Chess