In 2019, after visiting StartupDay and Skinnovation conferences, I redefined my own perception of value. Sending 350 million emails monthly didn't appeal to me anymore. I wanted bigger impact.
This ended our ten-year fierce competition. During the years of mentoring startups that followed, I realised how stupid we had been. Instead, we should have joined forces as soon as possible to go after bigger markets faster.
Grateful for the chance that liberated me from my obligations towards clients and employees, gave me back my freedom, and even some exit cash. Almost all employees from those days are still working in the united team. We could have been a very strong team. But it was time for me to switch scenery.
Grateful to all our team members from the early days till the last, to all our demanding clients requesting the impossible, to the Email Summit conference series keynote presenters over nine years, attendees, families and people close.
Erkki Markus, Mikk Orglaan, Tanel Rand 📧 — the first picture ever of us together, at Riga.comm.
Ten years of competition, one agreement and a new beginning
Sometimes in life it takes a very long time to understand one simple thing: the people and companies you fight with the most might actually be the ones you could have gone the furthest with — together.
For me, one of those stories is connected to Smaily. It's a story of ten years of competition, struggle, one-upmanship, wins, losses, and finally a very human realisation: maybe we should have put our bread in the same cupboard much earlier.
Ten years against each other
It wasn't an easy ten years. We competed in everything — sales, technology, customers, positioning, solutions, promises and capability. One did something, the other had to answer. One moved ahead, the other looked for a way to catch up or go around.
From the outside it might have looked like ordinary competition. In reality it cost us an enormous amount of energy. And the most paradoxical part was that we were both fighting on a small Estonian market. There were exactly as many customers as there were. They didn't suddenly appear just because two companies pushed harder against each other.
At the same time, neither of us was good enough at really going outside Estonia. So we kept clashing. For years. Both smart. Both hard-working. Both ambitious. But a huge amount of energy went into fighting each other instead of playing a bigger game together.
The real opponent was not the other company
Looking back, it's easy to see that the real opponent was not Smaily. The real opponent was a market that was too small. Thinking that was too narrow. Too little international ambition. Too much local measuring-up. Too much ego and too little strategic collaboration.
We could have understood much earlier that two strong teams don't necessarily have to weaken each other. They can complement each other. One company's strengths could have covered the other's weaknesses. One's clients could have supported the other's cash flow. One's technical capability could have supported the other's commercial capability. One's experience could have accelerated the other's growth.
But understanding that takes time. Probably too much time.
When hostility ends in calm
At one point we reached an agreement. That was the moment where ten years of competition could be put away in the same cupboard. Not with bitterness, but with the understanding that both sides had something valuable.
The two companies' teams got to complement each other. The two companies' clients got to support each other's cash flow. And the whole situation became simpler and more pleasant for everyone.
For me, it also meant a new beginning. That agreement helped me start a new journey — to step out of one long chapter and move on to the next. Not everything in life ends with an explosion, bankruptcy or great drama. Some things end with maturity, peace and understanding. This story ended well.
What I learned from it
This experience has shaped me as a mentor a lot. All the mistakes I've made myself, my mentees and advisory clients don't have to repeat.
I've seen what it means to spend years pushing energy in the wrong direction. I've seen how competition can turn into self-defence. I've seen how ego can block collaboration. I've seen how the market can be too small while the entrepreneur doesn't dare to think bigger in time. I've seen how technology doesn't save you if the strategic decisions aren't made. And I've seen how people, in the end, decide what happens next.
Technology always has limits. The market always has limits. Money always has limits. But in the end, decisions are still made by people. And people can make both very good and very bad decisions.
A mentor's baggage is made of stories like these
Today as a mentor I can pass on not just theory, but lived experience. To an early-stage founder I can say what not to wrestle with alone for too long. To a growth-stage founder I can show where competition and collaboration can get confused. In a larger company I can help see how people, roles, technology and strategy influence each other. To a company in crisis I can say honestly when it's time to fight and when it's wiser to come to terms.
Each stage has its nuances. But one thing repeats almost always: the biggest problems are usually not purely technical or purely market-based. Very often, people, decisions, fears, ambitions and relationships are behind them.
We could have been stronger together, earlier
Looking back at this story, the clearest thought is this: we could have collaborated much earlier. We could have put our bread in the same cupboard right away. We could have sorted out the Estonian market faster. We could have moved outside Estonia much earlier. We could have saved an enormous amount of time and money. We could have made a much bigger leap inside that window of time.
But life doesn't always work that way. Sometimes a person has to go through those mistakes themselves, the ones they later advise others against. And maybe that's exactly where the value of this experience lies.
Markets change, lessons stay
Today the market is completely different. I'm content not to be on that market anymore. They're content to be on that market. And I sincerely wish them well.
This story is no longer about who won or lost. This story is about how expensive a confrontation that lasts too long can be, and how valuable a mature agreement can be in the end.
Competition teaches. Loss teaches. Victory teaches. Collaboration teaches even more. And sometimes a new life begins precisely when you end the old fight.
#smaily #mailbow #challengist #sparklyhr