Coaching with AI: combining theory and practice in Upbeat

When Ilya Vasilyev steps into a training session, he doesn’t just launch into theory. Instead, he sets the stage for participants to dive into practice. As both an AI coach in the Start Smart learning programme and the co-founder of the start-up Cyborgs, he believes the best way to learn is to try learn from the experience.

“I didn’t want to be a talking head,” Ilya says. “In Start Smart, we focus on the participants’ projects. We use real tools, test ideas and talk to users. That’s where the real learning happens.”

Project as a living laboratory

The Upbeat project supports young people with immigrant backgrounds in building entrepreneurial and AI skills. For Ilya, joining as a coach felt natural, as he had already mentored startups and worked as a teacher. But what makes his role special is how it connects to his start-up.

With Cyborgs, Ilya and his team develop AI-powered workplace simulations where learners practise soft skills, the interpersonal and emotional abilities like empathy, teamwork, and conflict resolution that enable people to work effectively with others. Participants are placed in realistic scenarios where AI-driven characters behave like colleagues or customers, sometimes supportive, sometimes challenging, always unpredictable.

In Start Smart training sessions, young entrepreneurs in Finland and Estonia try the simulations in real training sessions, giving him immediate feedback on what works, what confuses them and what sparks genuine learning.

“Start Smart training is a great space for experimentation. I can see how learners respond to the simulations, and that experience feeds directly back into improving Cyborgs. It’s a feedback loop that helps both the students and the start-up,” he explains.

AI coaching is a growing trend

One of Ilya’s key insights as a coach is that effort, not shortcuts, drives meaningful learning. Simulations reinforce this philosophy. Learners are dropped into conflicts, cultural misunderstandings or high-stress scenarios.

AI coaching is a growing trend where AI systems create challenging, realistic situations for learners to practise in. The human coach then helps participants reflect, contextualize, and transfer those lessons into real life.

“AI can’t replace learning. But it can create the right challenges for people to grow. That’s what we’re doing in Start Smart – giving young entrepreneurs a chance to practise, to fail, and to succeed”, Ilya explains.

Benefits for learners and entrepreneurs

For Start Smart participants, having a coach who is also a founder adds extra authenticity. Ilya doesn’t just talk about entrepreneurship; he lives it daily in his own start-up journey. His guidance comes with real-world examples, from pivoting product ideas to navigating customer discovery.

For Cyborgs, Start Smart provides a chance to test new features with real users. Instead of waiting months for enterprise clients, Ilya can see immediately how learners engage with the simulations and use that insight to refine the product.

This dual benefit is what makes joint projects so powerful. They don’t just prepare young people for entrepreneurship. They also give entrepreneurs a place to test and improve their innovations.