From Chess Strategies to Business Success: How Ivan Kraynov Builds Winning Teams Across Global Markets

Ivan Kraynov is a serial entrepreneur and investor whose diverse portfolio spans from premium lounge bars in Dubai to specialty coffee ventures and innovative wellness brands. With a strategic mindset honed through years of competitive chess, Kraynov has mastered the art of thinking several moves ahead in business. As co-founder of international consulting agency ZenVIND and driving force behind ventures like TIMELESS lounge bars, ABC Coffee Roasters, and wellness brands including Little Death and WitiWiti, he has built an impressive track record across IT, hospitality, and wellness sectors.

In an exclusive interview with Entrepreneur Loop, Kraynov shares his unique philosophy of investing in people over ideas, revealing how his chess-playing background shaped his approach to business strategy and team building. From launching premium venues in Dubai’s competitive market to expanding coffee concepts across the UAE, his journey offers valuable insights into building and scaling diverse business portfolios while maintaining operational excellence across multiple industries.

Please provide a brief introduction of yourself and your professional background.

My name is Ivan Kraynov, I’m an entrepreneur and investor currently engaged in several major ventures across different industries, with a focus on IT, business consulting, hospitality, and wellness. One of the key initiatives in the consulting space is the launch of ZenVIND, a new international agency. The hospitality sector is also part of my business focus. Among the projects I’m especially proud of is TIMELESS, a high-end lounge bar brand set to open its first location in Dubai this autumn. It’s a bold concept with uniquely designed hookahs and an immersive atmosphere tailored to surprise even Dubai’s sophisticated audience. I’m also involved in the international growth of ABC Coffee Roasters, a specialty coffee company that has launched in the UAE and continues to expand. A number of other restaurant ventures I’ve invested in are currently in development, with new openings planned in London and Los Angeles. Alongside this, I continue to support innovative wellness brands such as Little Death, which produces natural sleep gummies, and WitiWiti, a line of organic daily nutrition shakes.

What inspired you to start your own business? What was the “aha” moment?

There was never really such a moment, because for as long as I can remember, I knew I wanted to run my own business and could not picture any other path forward. I also played chess from a young age, enjoying the process of building strategies and thinking a few moves ahead. And business communications always have something in common with chess.

How did you identify a gap in the market or need that your business fulfills?

I don’t approach business by looking for gaps in the market first — I look for strong teams with passion and capability. The market gaps reveal themselves naturally when you have the right people asking the right questions. But the core strategy is always the same: find exceptional people, give them the resources they need, and stay close enough to operations to adapt quickly when the situation demands it.

What have been some mistakes or failures you’ve made along the way as an entrepreneur? How did you recover and learn from them?

There have been lots of challenges, but the biggest lesson I’ve learned is this: in business, everyone makes the same mistakes, no matter the industry. These missteps might be due to a lack of knowledge — about laws, tax specifics, relationships with partners, and so on. If you study and analyze those patterns, you can learn how to make fewer mistakes.

What are the most important skills someone needs to be a successful founder, in your opinion?

Discipline is the most important quality. I believe anyone can become an entrepreneur, the main thing is to be disciplined and to use hypotheses to find your true passion. But success is a chain of coincidences, so it’s not enough to be well-read, educated, active, or the most skilled in your field. The thing is, everyone gets an opportunity at some point, but you have to be ready and not miss your chance. And it’s good to keep in mind that an entrepreneur is someone who moves forward by taking risks. What really matters is knowing how much you’re ready to risk.

What do you find most rewarding and most challenging about being an entrepreneur?

The most rewarding part is seeing your project grow. As someone who has been involved in sports all my life, I remember well the feeling of pride for earning a medal in competitions when I was a kid. I still experience similar feelings today: when you see financial results that reflect business success, it feels like a reward. The most challenging part for me personally is the routine — small daily tasks related to operational work. Another difficulty is accepting the fact that success, including in business, often depends on plain luck.

What are some future goals or plans you have for your business in the next few years?

To continue investing in interesting projects and exploring new industries. I don’t focus on just one area and can become interested in a project from any field if I truly see potential in its team. I enjoy building teams, improving them, motivating people, and moving forward. If the team is flexible, goal-oriented, and understands the purpose, it will be able to adapt to changing trends and reach its goals.

What advice would you give to aspiring entrepreneurs who want to start their own company?

Be prepared for the fact that no business or startup ever looks exactly like it was originally planned. Business evolves around client and partner needs, and if you’re not ready to adapt, you’ll lose your audience. And the main advice: never give up and never stop moving forward. If you burn out, take a break and rest, but then keep going.

Ivan Kraynov’s approach to entrepreneurship—rooted in strategic thinking, team-first philosophy, and adaptability—offers a refreshing perspective in today’s fast-paced business landscape. His emphasis on discipline over talent and his understanding that success often involves calculated risk-taking provides aspiring entrepreneurs with a realistic yet optimistic roadmap. As he continues to expand his portfolio across continents and industries, Kraynov’s story reminds us that sustainable business success comes from building strong teams, staying flexible, and never losing sight of the bigger strategic picture.