WHY became I a coach, mentor, flight instructor

The stroy of my life wrappen up.

1. StartupDay 2019

I was usually on some snowboarding trip with my friends in the end of January, but in 2019 we went later. So I participated StartupDay, because we pitched for ticketing, badges, sales and other technical solutions with my company Mailbow and didn’t win. So I wanted to make sure my solution was more complete and exceeded what was used there. Well, I was right in lots of apects and I intended to use all that knowledge while providing my services to JCI World Congress 2019 what was held in Tallinn November 4-9-th. I knew we could do better in so many angles. It was in my interest to see, how others do event big like this. What is good, what was bad. I paid high attention to every detail.

To be completely honest, there were 2 words I probably hated the most. Innovation and startup. Therefore all events that were promoted using these words didn’t get my attention at all. 

Innovation was practically all what I did as a work since 1998. I investigated businesses and verified what clients were telling us that they think they needed. Through pain I learned that in order to deliver I needed to do my own investigation and question clients far more than tehy expected us to know. It is impossible to solve any business problem without knowing goals and processes and bottlenecks and then develop a custom infosystem, CRM, ERP or even simple enough a webshop. It ain’t.
Startup was for ma and still is a fancy name which is more like an excuse why you can’t be break-even and need to burn investors’ money with high flames fast. Yet again all my businesses never grew out of that phase. We were bootstraping all the time. All resources at use all the time. Some employees didn’t like it at all, but it kept me alive and on edge all the time. I was never bored.

Anyhow, there I was, lurking around looking at fascinated people listening what smart people were sharing at stages, having meetings with other startuppers. But I, instead met and made new friends, talked with basically random people. Visited university startup pitches, all possible side events one could. Walked into investor’s event, and I loved it. Not that I met lots of clients and friends there, but also problems addressed and discussions. People were asking me if I was investing myself. I wasn’t. I was nose deep into my businesses keeping them afloat. The best advice I received was – Why don’t you let others do the harsh work, have sleepless nights, put all their energy, time, money, network, and other resources into game and risk only with my money and have goodnight sleeps, as I was going to invest anyhow to test out new ideas that popped up during daily business?

Well, that wasn’t enough. Another friend and known investor asked why was I not looking too happy. I had to say, well things weren’t the same anymore. I was tired of my business. Why don’t you exit then, I was asked. To whom? Asked I. To a comeptitor, if you want to get rid of it fast. Noooh, I couldn’t. I hated these guys for 10 years fiercly. 



2. Skinnovation.io 2019

One day I noticed strange ad in Tehnopol‘s newsletter. An startup event in Innsbruck, Austria, guys have half time on slopes skiing and half indoors. As I had gotten over from my fear of innovation and startup I thought – well, must be my kind of people. Not thinking too long and having StartupDay experience freshly in my head I bought the ticket and flew there. But this time I thought I fake I am an investor, giving myself an opportunity to try out something different. 

These were I think the most intense days ever of any conference I’ve been participating. I assume it was more me than organizers who created that feeling. I could write a long post about the event and it’s learnings for me, starting from fabulous host Hannah Klose whom I fell love with immediatly, but not only.

Setup and format of the event were completely new to me. I remember pitchings from where I hated the most ex-office supply sales manager with his electric snow cart Bobsla.com and some dutch guy with his funny accent having crazy idea of Indoor Skiing. A year later we got no snow in Nordics plus Bobsla has received number of awards and sold a lot. But back then I thought – who the idiot would invest into these ideas. Actually I found all these ideas dumb and too far from business I knew. 

But then after 2 beers I ended up developing business around Bobsla electric snow cart. Sergey is very humble and nice guy. In summer I was visiting him and I had 2 broken tires, so without him I would never gotten to lake Garda. But that’s another story. Also turned out, that Ron and I share a lot common values yet are very different. His indoor skiing innovation makes more sense day after day. What happened – I changed during these 3 intense days. 

And then back at my own work, 2 weeks later I just had enough. I had nothing new and fascinating in it for me anymore. I could not continue without hurting my employees, my clients. I had to make a decision. And I decided to exit and hand over my beloved co-workers and clients. 
What happened next was like in a book of sale. Found 3 potential buyers, eliminated 1. Continued discussions with 2. Sold to better match and offering. And I got a better person to all people around me.

Yes, it’s funny that we don’t see – sometimes it’s worth work together instead of against. Turned out my competitor was rather nice and ethical guy. Should have done that long time ago. We both lost great deal of money in this pointless war. Perhaps that was my greatest lesson.



3. Entrepreneur for 20 years

I created a dream job for myself that allowed to interact with interesting people, to travel, to visit conferences World wide, to study a lot, to creat a lot of value for me, my collegues and our clients. I started with selling online internet conections, then moved to web development, custom CRM, ERP softwares, ecommerce, payments, inventory, tickets, email marketing, the list seems endless.

I had the luck to become mentor for Enterprise Estonia, universities and later on for startups. Teaching is the best way to learn yourself. Right. Therefore I am thankful to Hando Sinisalu who asked me once to take the stage and present email marketing current status, which led to 9 years of my hosted conference series + number of other public speaking events, seminars, conferences, etc.

When opportunities present themselves – one should always grab the chance. Looking back, I took almost every chance I had & if I didn’t, so I was left aside.


4. Lecturer & consultant

Over the years it became clear, if I say anything, it has to contain something valuable. Performing as a funny guy on the stage is still kind of challenge for me. Presenting my point of views on yearly conferences ran by Äripäev and other event organizers I got the experience and confidence I could present anything that has value for me. Yet I always limited it to the business I was doing at the time. Not anymore.

As an opportunity presented I took the chance and presented story of my entrepreneurial career as “20 buckets to step into or onto“. That presentation wrapped up my experiences as an serial entrereneur. And also made me think – maybe I am not just an email marketing expert & software development company owner. Maybe I am bigger than my current work and it’s time to move on… 

After the last exit I had time for friends and kids. I took the summer off completely, did stuff I loved. And it felt great. Until I felt the urge to create value and to be respected once again. 

It’s time to do something what makes me feel great and provides value to ones seeking for it. Going back and analyzing where I provided and where we had troubles, it came clear to me. My job has always been – to understand the business and to provide solutions how can I improve it. The only thing different from now on is that I am focusing on doing the first part: analyzing business, evaluating ideas/service/product, help to make it fly having workshops and brainstorming, then optimizing and/or developing processes existent or new, helping to setup implementation plan, networking and matchmaking with third parties. It might be defined also as a business development by some. AND not doing the other part: developing the software by any of my companies anymore.

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