The following is the conversation with… just kidding 😄
This year, I attended the Lviv IT Arena. I met a few founders there and asked each of them to describe the very beginning of their entrepreneurial journey. If you’ve ever daydreamed about starting something on your own but didn’t know where to begin, you’ll see that even successful founders once stood exactly where you are.
In this article, you won’t find polished success stories. This is where you’ll get to know how the leap from employee to founder truly feels like.
I don't dare to take more of your time, so the first question is…
How did you cope with the switch from employee to founder?
What did the transition period look like for you?
Anton Avrynskyi, CEO & co-founder of Liki24 (former Deputy Chief Executive Officer, IT-Enterprise): The first thing you need when moving from employee to business owner is a financial cushion.
This buffer won’t last forever, but it makes the transition manageable.
The second thing is understanding what truly excites you. I strongly recommend going to events like IT Arena and other startup competitions. Listening to pitches and hearing different founders speak is one of the best ways to discover what resonates with you.
Oleksandr Shcherbak, CBDO & co-founder of Lilo (former Chief Business Officer, HELSI): Frankly, it was both exciting and terrifying. You constantly wonder whether it will work or not. As an employee, you have stability, and giving that up is never easy. But I started to stagnate after the team of professionals, which I was a part of, made HELSI a major player and a market leader.
Everything was running smoothly, but I felt like the race was over.
I missed the drive and challenge, and at that point, I realized it was time to build something new.
Sergiy Danylov, Co-Founder of Anima (also Professor Assistant, Taras Shevchenko National University of Kyiv): The main challenge wasn’t the role shift. It was carrying responsibility for the people. You’re suddenly the one who has to make sure salaries get paid, and investments are found. This cycle of “I must, I must, I must” never really stops.
The hardest part is planning how long you can operate in that mode, and asking yourself whether you can bear it again and again.
Ivan Fedorenko, CEO of a few businesses: When I joined a French company, I felt comfortable, but I knew it wasn’t enough. Everything was fine, yet I felt pulled toward something different. I had so much energy at the time. I worked eight hours at my job, and in the evenings and on weekends, I was involved in two or three startups at once. Yet, I managed to avoid burnout and rarely felt exhausted.
Looking back, I think I rested by switching between different types of work, and that variety actually kept me energized during the transition from employee to founder.
Did you take a sabbatical or a long break to launch a company?
What helped you realize it was the right moment to stop and fully pursue your new career?
Anton Avrynskyi: I believe a sabbatical, when you stay employed but “take a break”, is a half measure. You’re still holding a safety net, a plan B that prevents you from going all in. For me, that approach doesn’t work. You need to make a clean break.
That’s what I did. After 15 years at the same company, first as an employee and later as a partner, I decided to leave completely.
To create something new, you have to stop doing the old thing entirely.
That was my mindset. I had some savings and sold my share in the company, which gave me a cushion.
Oleksandr Shcherbak: No, while working at HELSI, the same group that later became the founders of Lilo began discussing the idea and concept behind the new product. We held our first strategic sessions and started crystallizing the vision together with our key founder and shareholder, Samvel Akobyan.
I knew I had to switch completely once it became clear it would require full-time commitment and investment.
The transition took about six months. I worked as Commercial Director at the time, so I needed to find a replacement and hand over my responsibilities. The entire transition was smooth for both HELSI and me, and gave everyone time to prepare. Once I left, I focused on building Lilo right off the bat.
Sergiy Danylov: I didn’t take a sabbatical.
The real turning point came when I realized I couldn’t split my attention between working, teaching, and building something new any longer. I was simply running out of time.
The significant shift occurred when I was moving in a completely new direction. Around 2016, I recognized that the future of AI would rely on understanding human behavior, attention, and cognitive patterns, rather than merely on objects.
Once I identified this trend and clearly saw that the new field required my full commitment, I stopped juggling multiple roles and dedicated myself entirely to building my own company.
Ivan Fedorenko: I didn’t take a sabbatical because I felt tied to the company and responsible for delivering results. Only in the third year did I understand what was coming next. First, things finally started working the way I wanted them to. Second, I realized I could achieve more in my own company.
That clarity showed me it was time to rethink my path and build something entirely by myself.
Who did you consult with when making the decision?
Who gave you the most valuable advice? What communities or networks were helpful to you?
Anton Avrynskyi: I talked to many technical and business-minded people in my network. It’s important to share your ideas widely with developers, entrepreneurs, investors, and anyone who can challenge your thinking. I reconnected with old contacts and reached out to friends and family. I also met new people via introductions and steadily grew my talking circle.
Once I had a rough idea of what I wanted to build, I started meeting people involved in that space for feedback. You need these conversations because they help you see blind spots. Some people will tell you your idea is bad, and that’s fine. The key is not to listen to everyone, but to collect different perspectives and form a clear picture of what you want to build.
Once you find the idea that excites you the most, move quickly.
The discussion phase shouldn’t last more than a month.
I know many people who spend years exploring different notions without ever starting. As a result, their ideas just get outdated.
Oleksandr Shcherbak: I can’t name one single person who gave the most valuable advice. I gained many useful insights from different people and perspectives.
My network was crucial to my progress.
I relied on it a lot. My team and I ran informal surveys among our friends and acquaintances, asking questions like:
- “What would an ideal insurance look like for you?”
- “What pain points do you currently experience in healthcare?”
Those conversations helped us understand better the real user needs and shape our idea accordingly.
Sergiy Danylov: When people interview me about psychology and ask for advice, I always say the same thing:
The first rule is not to blindly follow anyone’s advice.
This doesn’t mean you should isolate yourself. You need to listen widely, stay in the field, absorb as many signals, ideas, and stories as possible. We are imitators by design. That’s how humans learn. The value comes from recombining what you see around you into something that fits your own context. So the most valuable “advice” is not a specific sentence someone told me.
At the same time, I am genuinely grateful to many people whose wisdom and experience have shaped how I think.
Ivan Fedorenko: I spoke with a friend who was one year ahead of me and had already founded his own IT company. He gave me top-notch advice:
Launch the first product version as an MVP (Minimum Viable Product) and don’t pour all your money into it.
I didn’t listen, and that was a mistake.
Later, I began studying in business schools, taking management courses, and joining accelerator programs. Those programs were especially valuable because of the networking. You meet people who fall into the same traps, and it’s easy to learn by watching peers face challenges similar to yours. And, of course, the mentors you meet along the way give you the knowledge that helps you move forward.
How did you manage your personal priorities?
Health, relationships, and personal life. What compromises did you have to make?
Anton Avrynskyi: In the first years of building my own company, I didn’t really have a life outside of work. I was obsessed with it, talking about it at home, living it every day. At that time, I already had two small kids. I tried to be present, but the reality was that 90% of my time and energy went into the business.
I don’t believe it’s possible to build something from scratch without being fully dedicated to it, at least, not in my experience. I was hands-on, creating everything from zero, and that required total focus. There was no balance in those first two years. It was roughly 90% work and 10% family, and you have to be mentally prepared for that.
The idea of balance simply doesn’t exist during the early stages.
Oleksandr Shcherbak: I used to work in a mode that doesn’t fit into the standard “9 to 5” format. I often have to adjust plans on the fly, work at a high pace, or postpone personal matters for the sake of urgent tasks. In that rhythm, launching Lilo wasn’t a dramatic shift, but it definitely increased the intensity.
The hardest part is maintaining balance between work and the time I want to dedicate to the people who matter to me - family, my close circle, and friends. The reality of building a startup means having less time to rest. But I consciously try to stay connected, pay attention to my personal life, and not lose the sense of life beyond work.
For me, it’s crucial to do something that genuinely inspires and energizes me.
When you love what you do, you have enough emotional resources even in a high-intense pace, and the rest you need is mostly physical, just to let your body keep up with the tempo your mind sets.
That’s what helps avoid burnout and stay productive without losing the support of the people closest to you.
Sergiy Danylov: Speaking as a neuroscientist rather than a founder, my general recommendation is to twist your life into a “rope of habits” that consistently pulls you toward your goals. And that rope must include plenty of rest, even though that’s especially hard for a founder.
You also need some physical activity. Unfortunately, startup life often means sitting all day, which isn’t healthy. At the same time, the very sense of purpose behind what you’re building provides enormous psychological protection.
There’s nothing more powerful for mental health than having a clear goal and meaning.
Ivan Fedorenko:
For me, startups and the process of founding companies became my main life.
Many of my friends were connected to the company, so relationships and work were intertwined.
I didn’t feel any discomfort at that time, but I often had to work nights and miss sleep, which definitely hurt my health.
How and when did you tell your colleagues about your decision to leave and start a company?
What emotional challenges came up, and how did you handle them?
Anton Avrynskyi: It was an incredibly difficult period, probably one of the hardest in my career. I had been thinking about leaving for several years before I finally decided to go. There were long months of preparation and reflection. Emotionally, it was devastating.
When I finally decided, I just had an honest conversation with the two founders. Of course, they were shocked, but we agreed I would stay for six more months to ensure a smooth transition. During that period, I worked at full capacity, covered various areas, trained colleagues, and transferred all my responsibilities.
A month before leaving, I shared the news with the rest of the team. They were also shocked, but I believe transparency and preparation are the key. You can’t just announce one day that you’re leaving tomorrow. It has to be handled carefully and respectfully.
Looking back, I’m proud of how it went. We’re still on great terms with the founders and the team. We stay in touch, help each other whenever possible, and remain friends.
My philosophy is simple: come in and leave with integrity.
Oleksandr Shcherbak: I spoke directly with the CEO of HELSI. Since I was an effective manager during my time at HELSI, we repeatedly tried to launch initiatives aimed at expanding cooperation with insurance companies, so the conversation wasn’t difficult. We had always had a good relationship, so I wanted my departure to be as smooth as possible for the company.
I approached it responsibly: trained the team, shared new ideas, and transferred all the necessary knowledge before leaving
Another important factor was that I had the best team under my leadership - mature, independent managers. By the time I left, I was no longer a “babysitter” for them, so the transition felt natural and comfortable.
This approach ensured a smooth process and helped avoid any disruptions for HELSI.
Sergiy Danylov: It was genuinely difficult.
After working for twenty years in the same place, you reach a moment when you simply stand up and walk away. That shift hits you hard.
We had an outstanding department head. He was disappointed that my partner and I were leaving, but he understood that we were stepping toward something we truly wanted. That understanding made the transition emotional but ultimately honest and respectful for everyone involved.
Ivan Fedorenko: I told my colleagues I wasn’t abandoning them. I assured them they could reach out to me anytime for questions or support.
I didn’t close the doors.
I thanked them, said I genuinely enjoyed working with them, and explained that I needed to move forward for the sake of my own path. There were no negative emotions. We ended things on an optimistic note.
Conclusion
In this article, I don’t want to provide the summary and disrupt your thoughts. I hope you will draw your own conclusions based on these conversations.
My personal takeaway can be described by this quote:
“And sacrifice scares you, but sacrifice brings growth and growth is exactly what you need. Define your priorities, forget your balance”
Continue reading
If these reflections made you curious about the practical side of building your first company, you may want to read my 10 mistakes I made as a first-time solo founder.
As usual, thank you for your time. I would appreciate it if you hit that like button, and I look forward to hearing your thoughts in the comments!
📰 Read me on the platform of your choice: Substack, DEV.to
Till next time! 👋
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