Between Top Executive and Startup Founder: Rain Vääna’s Honest Comparison of Two Worlds
Rain Vääna, a man who knows exactly what it means to start from scratch, will take the sTARTUp Day stage. After more than 15 years as a top executive, including nine years as CEO of Ragn-Sells, he decided to leave the safety of corporate life behind and dive into the uncertain yet exciting world of startups.
Before stepping on stage, Rain shared his thoughts with us about the meeting points of two very different worlds — corporate leadership and startups — as well as about fear, starting over, and what a good life means to him.
The reason was actually quite simple — we all want and need to grow. One way to do that is in the corporate world, and another is by becoming an entrepreneur. I had long felt internally that I wanted to become an entrepreneur. Before leaving Ragn-Sells, I attempted to facilitate a management buyout of the Estonian branch, along with another board member, to acquire the company and continue leading it independently. That was my initial preference for entering entrepreneurship, but when it didn’t work out, I had to find an alternative path. The logical next step was to start a startup, because in that world, you can immediately think and act internationally.
I had a clear desire to do something that wouldn’t be limited to Estonia or the Baltics, but would instead have a European or even global reach. The idea that what we were building could grow into an international success story was deeply motivating.
In reality, the decision wasn’t an impulse. I had been turning that thought over in my head for years – in parallel with my developments at Ragn-Sells. For example, the management buyout process itself took a couple of years, and during that time, I had to look in the mirror and ask: What if it doesn’t work out? What are the next steps? Do I stay in the corporate world or finally take the leap into entrepreneurship?
There were many ideas during that time. KWOTA just happened to be the concrete expression we gave a name and shape to in the end. But the thinking behind what to do, what I’m good at, and what could be truly meaningful globally – that was constantly in the background. I wanted to build something that creates value internationally, not just for Estonia.
What was the biggest culture shock when moving from the corporate world to startups, where there’s practically no certainty?
That shock comes quite naturally. When you’ve been at the top of a large organization for a long period, a kind of learned helplessness inevitably develops. You’re surrounded by people with all sorts of specialized skills to whom you can delegate tasks, and the system works. But when you start building your own company, you will need to provide all those skills – especially in the beginning. You can’t delegate anything because you simply don’t yet have a team. You have to handle sales, finance, marketing, communications, strategy and everythign in between, yourself – and that’s a huge change.
It could be called a shock, but for me, it was more a joy of rediscovery. It was exciting to realize how many things I had to remember how to do again – tasks I used to handle long ago but hadn’t touched in years because someone else had taken care of them.
Another major difference is the pace. In the corporate world, implementing change is a slow process – there are layers, processes, and numerous people to consider. In the startup world, everything moves much faster. If you want to make a change, you can do it immediately. If you want to test a new direction or strategy, you can experiment with the following week.
At the same time, it also means there’s no safety net – if you make a mistake, it’s entirely on you. But I like that pace and direct impact. I don’t have to wait for approvals. I can make a decision with a small team and act immediately.
In the corporate world, you always have some level of safety net: the company is running, profits are growing, and small mistakes don’t shake the whole ship. In a startup, there is no such thing as a net. You must react much faster because situations and markets change in days, not months.
What skills did you feel confident in as a top executive, but realized as a founder, no longer worked the same way?
I realized quite quickly that some skills I considered strengths – such as thorough analysis, broad involvement, or patient strategic planning – simply don’t work in a startup’s early phase. There, you must make decisions much faster and tolerate a much higher level of uncertainty.
Another key difference is that in a large company, you shouldn’t and can’t do everything yourself – you lead people, not processes. In a startup, it’s the opposite: you have to do everything yourself. You can’t say “that’s not my job” because everything is your job. It means you must be ready to jump into a new role every day – one day you’re a salesperson, the next a CFO, the next Product Manager.
It was a significant mental shift – realizing that being a leader no longer means giving direction and control, but relatively constant learning, adapting, and taking action. Yet it’s incredibly liberating. In a startup, you see the impact of your decisions immediately. If something works, you see results within a week. If it doesn’t, you can change course right away. That speed and the direct link between action and outcome were something I missed in corporate life – and what reignited my drive in the startup world.
Please briefly explain what KWOTA did and what the most significant lesson from that venture was.
KWOTA focused on measuring and monetizing carbon savings achieved through increased material reuse. We aimed to develop a system that enables material manufacturers to generate additional revenue by increasing the proportion of recycled materials in their products. The goal was to make carbon savings financially measurable and tradable.
The biggest lesson was that in a completely new and globally unique field, you must find a real paying customer as quickly as possible – even if it’s just a small amount. Free trials don’t prove real market demand. I also learned that while having a plan is essential, flexibility and readiness to adjust your idea quickly based on market feedback are even more critical.
KWOTA’s operations ended, but you started again quite soon with Gritnord. How do you mentally and practically start over?
That’s always a big question – how to start again after failure. In entrepreneurship, failure is simply part of the process. Every founder who genuinely builds and experiments will face it sooner or later. What matters is having an agreement with yourself in advance about when it’s time to draw the line. If something doesn’t work, you must be honest about it and move on. Otherwise, guilt and burnout creep in, and eventually, you don’t even want to hear the word entrepreneurship.
What helped me was taking it in a realistic perspective. KWOTA closed, but several things went well. Within a year, we built partnerships with nearly 50 international companies that voluntarily shared their data with us and placed great trust in our work. We reported on more than 1 million tonnes of recycled materials reused. That gave me confidence that I could create value and energize a team, even if the specific business model didn’t work this time.
Gritnord was a natural continuation — some members of the KWOTA team wanted to move forward together, and we already had a clear understanding of our strengths and what we could do better this time. From the start, we decided not to focus on raising funds but on building a business with paying customers and real revenue. Our priority is to prove the model through traction and profitability, ensuring stability and independence from day one.
Mentally, what helped was accepting that failure isn’t the end – it’s just part of the journey. Each new beginning is a bit easier because you already know what to avoid and how to take better care of yourself.
What helped you choose action instead of fear?
Fear is a natural part of entrepreneurship – the question isn’t whether it exists but how you handle it. I always try to distinguish between two types of fear: panic, which paralyzes you, and healthy fear, which sharpens your focus and forces you to prepare. When you understand and acknowledge the risks and plan consciously, fear actually becomes a driving force.
A clear plan and the first paying customers helped me focus on action. When customers are willing to pay for your product or service, that’s the best proof that you’re on the right track – and it immediately reduces uncertainty.
It also helps to accept that in entrepreneurship, you can never know or control everything. Failure isn’t the opposite of success — it’s part of it. You can’t test your limits without occasionally falling short. The real question is what you do with that new knowledge: do you get up, learn, and improve, or do you let self-pity take over and drag yourself — and those around you — down?
What are Gritnord’s growth goals?
Our purpose is to make B2B business growth predictable. We are in a clear growth phase, building on strong foundations and real customer demand. In 2025, our focus is on the Baltic, Nordic, and wider European markets, followed by expansion into the U.S. and, over time, eastward into new regions. Our long-term ambition is bold but clear: to become the leading B2B meetings delivery platform in the world by 2030 — a trusted system that helps businesses everywhere connect faster, smarter, and with purpose.
The goal is steady and profitable growth from the very beginning. We want to build a company that is the best in its field — not necessarily the biggest, but one with the strongest culture and the most reliable service. We want to be recognized for delivering the highest-value meetings in the market and enabling our customers to achieve exceptional closing rates.
This year's sTARTUp Day one topic is “What is a good life.” What does a good life mean to you?
For me, a good life consists of three words – faith, trust, and balance.
Faith means having something or someone to believe in — whether it’s God, nature, your family, or your own mission. It’s the quiet confidence that life has meaning beyond the moment you’re in. When that faith is present, there’s a sense of peace — and with it, a deeper kind of happiness.
Trust means not living in constant defense mode, but believing in the people around you — your family, friends, colleagues, and business partners. When trust is present, life feels lighter, calmer, and undeniably more beautiful.
And finally, balance — between work, family, yourself, and rest. It’s the foundation beneath everything else. Without it, even the most impressive achievements lose their meaning. Balance means taking care of your body and mind — moving, training, eating well, and allowing yourself to rest. It’s about spending time with people who matter, learning new things, and finding joy in small moments that don’t need to lead anywhere. Sometimes that means being happy doing nothing at all — letting your thoughts wander, giving space for creativity and calm to return. True balance isn’t about perfection; it’s about rhythm — knowing when to push forward and when to let go, when to act and when simply to be. It’s what keeps ambition alive without losing yourself in the process.
Faith, trust, and balance – these three are the foundation of a good life for me.
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sTARTUp Day Classics: Milda Mitkutė keynote in 2020