40 Years of Life Lessons: Failures, Successes, and Estonian Journey to Global Impact
I was born in Tallinn, the capital of Estonia—a digital nation with 1.3 million people and 70% forest coverage. Today, Estonia boasts 10 unicorns and ranks as the top country in the world for startups and unicorns per capita. But when I was born, it was a different story. We were poor—super poor.
In 1991, when Estonia regained independence, the average gross salary was around €10 per month, and GDP per capita was just $3,000—placing us in the lower third globally. The 1990s were tough: mafia-run wild west times where nothing felt safe, and everything was up for grabs.
Thirty years later, Estonia is a beacon of innovation: the most advanced digital society in the world with e-governance and e-residency, a thriving startup ecosystem, and one of the safest countries to raise a family.
“It doesn’t matter where you start—it matters where you end up.”
The Unexpected Pianist
My parents enrolled me in a classical music school to learn piano. Why? To this day, neither I nor my parents know. I vividly remember the admission test. There was no sound coming from my mouth neither from my back. I couldn’t play a note to save my life, but somehow, they took me in.
After 10 years of learning classical music, I often had philosophical discussions with my piano teacher. Not because I was an exceptional student, but because I frequently skipped practice. Around that time, my real love—basketball—took over. It was the NBA highlight era: Jordan, Bryant, O'Neal, Hill. I decided to transfer to a school that had produced Estonia’s first NBA player.
“Nothing is fixed. Enjoy the journey and change course when you feel it’s right.”
Dreams Meet Reality
At my new school, I joined the basketball team, competing for championships with an incredible group of classmates. We had so much fun during our teenage years—sports, “some” studies, and parties. I enjoyed the delicate balance of all three. During this time, I met my first true friends, and to this day, we’re still a gang. My dream? The NBA. My idol? Kobe Bryant (RIP). And Allen Iverson, who inspired me with his "short" height of 183cm. I thought, “If he can do it, so can I.” But I was 176cm—and white men can’t jump.
“Dreaming is free, but achieving it isn’t. When reality doesn’t align with your dream, adapt and move forward. Never settle.”
The Soldier’s Challenge
I developed a strong interest in hiking and military sports in high school. The toughest competition I participated in was a gruelling 110km patrol with complete military equipment under simulated enemy fire. My team of four barely adult guys. Heat. Mud. Heavy sprints. Exercise checkpoints.
Despite the odds, we ranked in the top 11 out of 30 teams, beating professional soldiers from way larger countries. One-third of the teams didn’t even finish. It was brutal, but the experience strengthened our bond as a team and gave me another lesson.
“The right team is your real unfair advantage.”
Into the Army
Riding the wave of militarism, I joined Estonia’s nine-month compulsory military service immediately after high school. The first three months are known as rookie months, a time when, back in the day, sergeants could push your physical and mental limits as much as they wanted. It was tough, especially since leaving the barracks to see family or friends wasn’t allowed during that period.
About a month in, we faced a 24-hour-long military sports competition, where the best squad would earn a free weekend outside the barracks. Who wouldn’t want that? Our squad of 12, living together in a cramped 12m² room, was dreaming of winning. With waist-high snow and relentless challenges, teamwork became our lifeline.
Guess who won the competition and got the free weekend? ;)
“Hang on. Your time will come. Be ready to execute when the moment arrives.”
From Rookie to Officer: Rising Through the Ranks
My initial nine months of service were extended to 11 because my superiors in the army believed I had the potential to become a good officer. They offered me courses to become a sergeant and then advance to an officer rank. I thought, Why not? If I was already there, I could go all in.
Out of 108 brave and strong men in our “flight,” I was the only one given the opportunity to attend all these courses. I felt humbled and deeply thankful that they saw a little Napoleon in me. :)
The courses were fascinating—we learned it all about leadership, navigation, communication, military strategies and tactics, weapons, bazookas, grenades, machinery. After completing the courses, I returned to my base feeling 10cm taller and wider. I was so proud. By then, I was about 99% soldier.
“Whatever you do, aim to take the best out of it.”
Fork in the Road
After the army, I faced a choice: military school to become a professional soldier or university to study economics and business. Coming out of the army with a positive experience, I was more inclined to pursue the military school. However, I didn’t get in. Despite being ranked #5 on the list, I was rejected. So, I pivoted to option #2 and began studying economics and business, eventually specialising in finance and leadership.
Looking back, I’m deeply grateful it turned out this way. I love my journey as an entrepreneur and investor and wouldn’t trade it for anything else.
“Everything happens for a reason. You’ll understand it in time.”
The Hustle Begins
During my university years, I quickly grew bored and decided to find a job to earn money and gain experience.
As a side hustle to pay the bills, I joined a security firm as a security guard. Ironically, my post was at the same university where I was studying. After three months of part-time work, I wanted to advance in my career at the firm.
I asked my boss about growth opportunities. He told me there were two options. The first was to become a senior security guard. I wondered what that entailed. He explained it meant getting more stripes on my badge and earning 1 kroon (€0.07) more per hour. I asked about the second option. He said I could become a team leader, which came with a slightly higher salary but required me to be available 24/7.
I thanked him—and resigned.
“Seek opportunities that challenge you. Comfort zones are for standing still.”
Learning to Sell
During my three months as a security guard, I spent countless hours behind the security screens reflecting on what I wanted from life. Freedom, independence, and the financial means to enjoy life to the fullest. I wanted to experience the world and connect with people. But I realised none of this would come overnight—I needed to start somewhere. A right part-time opportunity that could build a strong foundation for my future seemed like the right step.
I thought that a sales job might do the trick. I joined a newly established distributorship for an international direct sales company specialising in household appliances. And oh boy, was it tough. My job as an independent contractor involved knocking on doors, getting inside, delivering product demos, and convincing people to buy a product that cost three times the average monthly salary—on the spot.
After 30 demos without a single sale, I was close to losing hope. But one question kept driving me forward after every failed attempt: What can I learn from this demo to make the next one my best yet?
And then it happened. Demo number 34 was my first sale. I was in heaven!
“Learn from your mistakes and improve step by step. Nothing comes overnight.”
All In: The Leap from Sales Rep to Entrepreneur
The next day, the customer decided to return the product. Surprisingly, this didn’t bother me. I had already tasted the incredible feeling of closing a deal and wanted more—much more.
The company I teamed up with soon offered me an opportunity to build my team and contribute to the development of the business. After six months of working part-time and achieving great success as a sales rep, I made a bold decision: I put my studies on hold to focus 100% on this business opportunity.
It was a chance to develop my skills, gain experience, and embrace entrepreneurship. The opportunities ahead were too good to pass up—and I didn’t disappoint.
“When you find something you desire and have nothing to lose, go all in. Focus. Nothing else matters. ”
Building a Blueprint: Turning Failures into Success
After mastering the sales game, I felt ready to take on a new challenge: building my branch. This meant recruiting, training, motivating, promoting—and sometimes firing—people. The beginning felt like my early days as a sales rep: full of trial and error.
I recruited 3–5 new trainees each month, training and motivating them to get out there and do the job. And month after month, they failed—not because they weren’t capable, but because I wasn’t good enough as a leader yet.
I realised I needed a system—a blueprint that could turn almost anyone off the street into a sales machine. So, I got to work. I tested scripts day and night, refining them constantly. When I ran my sixth training session to new trainees, it finally clicked. Two real superstars emerged from that group, and I’m proud to say they’re still my friends today.
The game was on, and my scripts and strategies worked like clockwork.
“Sometimes you lose. Sometimes you win. Both are needed for progress.”
Earning Beyond Money: The True Wealth of Developing Others
Fast forward six years, and I had built a team of over 300 people. I had the honour of recruiting, developing, and working alongside multiple top 25 sales reps globally within a company of over 12,000 reps.
My branch broke a world record in sales and was repeatedly awarded as the #1 branch in a competition of more than 2,000 branches worldwide. But the true highlight of the experience wasn’t the awards or records—it was learning how to develop leaders who could surpass me. I recruited, trained, and helped multiple leaders rise to the very top of the company.
As Zig Ziglar famously said: “You can have everything in life you want, if you will just help other people get what they want.” This principle guided everything I did, and the results were extraordinary. My team and I proved that a small, relatively poor country like Estonia could deliver world-class results if you poured your heart and mind into the game.
The money earned was beyond anything I had imagined—I was earning sums I never thought possible. But the real wealth came from the journey itself. Over those years, I travelled to 30 countries for business and leisure and attended countless trainings on leadership, direct sales, psychology, telemarketing, customer service, communication, personal growth, and others. By age 25, I had gained an education and experience that no university could have provided.
“A piece of wisdom from my first coach: Don’t chase fame or money. Those things will come naturally if you do what you love and pursue it passionately.”
From Sales to Digital Dreams: Embracing a New Era
Every story has an end: most of the time, that ending comes when progress stalls. That’s exactly how I felt after years in the direct sales industry. It was incredibly intense and demanding—nothing was recurring. Each day, you had to start from scratch, build momentum, and fight for results.
The final straw was my failure to break into the Polish market. That setback was the nail in the coffin, and I knew it was time for something new. I was looking into emerging trends. The internet was booming, and digital marketing was on the rise.
After analysis and planning, I invested in a franchise license from Canada and co-founded a digital marketing agency. The idea of leveraging the internet for continuous sales & marketing on a much larger and more predictable scale was exciting. However, the first two years were incredibly challenging.
We quickly realised that our region's digital marketing industry was still in its infancy. There wasn’t an established market. So, we pivoted to focus on training and raising market awareness. It was a long, uphill battle, but it paid off.
After a couple of years, we became one of the top digital marketing agencies in the region, consistently ranking in the TOP 25 franchisees globally.
“If you fail to plan, you plan to fail. And even with a solid plan, life doesn’t always follow the script—be ready to adapt.”
The Cost of Greed: A Lesson in Misjudging the Market
Inspired by the potential of the internet industry—and with dollar signs practically dancing in front of my eyes—I got greedy. I decided to make a significant investment to purchase a master franchise license for the entire region of the Baltic States. My goal was twofold: protect the market on one hand and scale it on the other.
I thought I was being clever. It turned out to be the dumbest investment I ever made.
In a year’s time, we sold exactly zero franchises. The market needed to be more educated, and the barriers to starting a digital marketing agency on your own were nonexistent. And if you know people from the Baltic countries, you’ll understand—they prefer to figure out everything themselves. It was a huge mistake.
“Learn from your experiences. If you repeat the same mistake twice or more, you’re lazy or not focused enough.”
Karma in Action
I had dreamed of having a son for years. I even had his name ready long before he was born. When the time finally came, the doctors told us he needed to be delivered much earlier than expected because he was too little.
One minute after his birth, I held my son in my arms—but only for a moment. He had to be placed under machines immediately. Those were the most intense two minutes of my life. His vital functions didn't start, and all I could do was wait. Then, by some miracle, his system started showing signs of strength. The numbers on the monitors, which had been dropping, began to climb. Slowly, he stabilised.
The following months were spent in and out of hospitals, taking things one day at a time. I will always remember one specific moment. My son urgently needed the help of a unique medical machine. The odds hit me like lightning—a few years earlier, when running my digital marketing agency, we had fundraised to help that same hospital purchase that exact machine. And now, it was saving my son’s life.
“Be kind. Be humble. You never know when life will come full circle. Karma is a bitch or an angel.”
The Costly Mistake of Ignoring My Own Advice
As our digital marketing agency continued to thrive, my co-founder and I began to feel it was time to move on after 10 years of running the business. We started preparing the company for sale—streamlining internal processes, securing a strong team, maintaining solid sales, and finding the right managing director to lead the business forward.
From past experiences, I learned that the best leaders often emerge from within the team. These are people you know, trust, and can guide you in the direction you envision. But this time, I didn’t follow my own Lesson #14. Instead, we decided to headhunt an external candidate—a so-called “A-class player.”
Oh boy, how wrong we were.
We found someone with a strong track record on paper, and everything seemed great—until the results didn’t come. In fact, the opposite happened. My biggest mistake was letting the situation drag on for far too long. By that time, I was already focused on other new projects, and this was no longer my main priority.
This poor decision ended up costing us a 6–7 figure sum.
“Hire slow, promote from within, and fire fast.”
Between Birth and Death: Choosing a Life Full of Purpose
After selling the business, I decided to take some time off. Easier said than done—the universe doesn’t tolerate empty space. Offers and opportunities came flooding in. While I rejected most of them, a few stood out as exciting challenges I couldn’t resist.
By then, I had already been mentoring international teams for several years and absolutely loved it. Alongside mentoring, I collaborated with global companies, helping them develop training programs and training their teams. I even (co-)founded a couple of businesses in the field of education.
This was an enjoyable and fulfilling period in my life—meeting incredible people, exploring new opportunities, and travelling the world. From east to west, north to south, I saw it all while doing work that genuinely energised me.
“Life happens in the space between B and D—Birth and Death. In between are the C as Choices you make. Those choices will make or break your life.”
From Founder to Funder: Embracing the Angel Investor Role
While making money, I was smart enough to start investing in different asset classes back in 2006, but the concept of angel investing was entirely new to me. While mentoring and training numerous startup teams, I kept hearing about these mysterious creatures called angel investors. The idea intrigued me—investing time and money into teams you believe in, working closely with them, and, if you’re lucky, reaping long-term financial rewards while enjoying and learning from the journey.
I knew this was something for me.
Some people call angel investing an expensive hobby. I disagree. If you commit to it full-time and approach it professionally, it’s far from a hobby. It’s a delicate, focused job that allows you to contribute without the operational burdens of being a founder. And I love that role! As Richard Branson used to say, “Screw it, let’s do it!”
Fast forward five years, I’ve reviewed over 1,500 investment decks, personally invested in 30 early-stage impact startups, led seven investment rounds as a lead investor, helped raise millions of euros from hundreds of investors, and have been advising incredible teams across the globe.
This track record earned me the "Rookie of the Year" award in the angel investor network, which I later had the honour of chairing as President.
“Trust your gut—and your butt.”
People, Planet, Profit: My Journey Into Africa
Over the years, my journey has brought me to Africa time and time again—South Africa, Ghana, Uganda, Kenya, Morocco, and Egypt. Along the way, I developed a deep interest in impact investing and purpose-driven projects. Everything we do has an impact, and it’s up to us to decide whether that impact will be positive. For me, that means contributing to the planet, the people, and making it financially sustainable through profit.
I had a dream of doing business in Africa.
One thing led to another, and soon, we established an international team of game changers working in the climate and carbon markets space. Our mission? Plant fast-growing bamboo to restore degraded lands, sequester carbon, sell high-quality nature-based carbon removal credits, and generate sustainable, regenerative biomass.
While doing all this, we also work closely with local communities, improving their livelihoods and creating job opportunities. Our project is the largest intact commercial bamboo plantation in East Africa. Advocating for Africa and bamboo has opened doors to incredible global platforms like the World Economic Forum, COP, the African Climate Summit, and more.
This journey has connected me with amazing people who care equally about people, the planet, and profit. Africa’s potential is immense, but it also comes with significant challenges. Without a doubt, this has been the most complex journey and project I’ve ever undertaken, but I hope it will prove to be worth it.
“Don’t judge a book by its cover—or its reviews. The only way to truly understand is to experience it firsthand.”
Beyond the Wins: What It Truly Takes to Succeed
If you’ve read it this far, you might think I’ve been incredibly lucky, and that success has always been a natural part of my story. My dear friend that couldn’t be further from the truth.
Everything in life comes with a price.
First, I firmly believe that luck is where preparation meets opportunity. I’ve worked tirelessly, often to and over the brink, and I’ve had far more losses than wins. As Winston Churchill famously said, “Success consists of going from failure to failure without loss of enthusiasm.”
Second, all this striving and achieving can take a toll if you don’t prioritize self-care. For many years, I didn’t. I faced burnouts and battled depressive states because I was so focused on chasing the next goal, thinking, Once I accomplish this, everything will be good, and I’ll be happy. In the process, I often forgot to relax, enjoy the journey, and genuinely appreciate the people around me. Even now, I remind myself daily that good sleep, regular exercise, healthy food, and meaningful relationships are essential for living a great life.
This brings me to a beautiful poem by David L. Weatherford, which I offer as Lesson #20. Take a moment to read it.
“Have you ever watched kids
On a merry-go-round?
Or listened to the rain
Slapping on the ground?
Ever followed a butterfly’s erratic flight?
Or gazed at the sun into the fading night?
You better slow down.
The music won’t last.
Do you run through each day
On the fly?
When you ask: How are you?
Do you hear the reply?
When the day is done,
do you lie in your bed?
With the next hundred chores
Running through your head?
You’d better slow down.
Don’t dance so fast.
Time is short.
The music won’t last.
Ever told your child,
We’ll do it tomorrow?
And in your haste,
Not see his sorrow?
Ever lost touch,
Let a good friendship die
Cause you never had time
To call and say, “Hi”?
You’d better slow down.
Don’t dance so fast.
Time is short.
The music won’t last.
When you run so fast to get somewhere
You miss half the fun of getting there.
When you worry and hurry through your day,
It is like an unopened gift thrown away.
Life is not a race.
Do take it slower.
Hear the music
Before the song is over.”
