Dag Ainsoo

Could you tell us about yourself? Imagine you have amnesia and have forgotten all aspects of your life. To bring everything back, you need to remind your future self about what type of person you are today, the principles, and other important things of your current life.

Because it's both work-related and personal life-related, I would like to emphasize that I deeply care about my family. My wife and kids are incredibly important to me, and they are my top priority.

Additionally, it's important to note that I am hard-working and ambitious. I'm far from being lazy. I engage in various activities, I do a lot of things outside of work, for example, I do sports and so on. This reminder is necessary to understand my commitment beyond professional responsibilities.

However, I also recognize the importance of balance. That's why I mentioned family first. I don't work solely for achieving goals or fulfill obligations. I genuinely enjoy my work and do it because I love it. I'm not doing it for someone else or any other reason. It's a reminder that my passion drives me, or else I probably wouldn't pursue it. These aspects hold significant value to me.

Trust in my working partners is equally crucial. They are like a second family to me. The main focus for me is building something together with people I genuinely enjoy collaborating with. Working with Herty and Cristobal, for instance, has been particularly gratifying as we complement each other and learn from one another in various ways. I learn different things from different individuals, even those who are quite different from me.

An important principle I adhere to is the commitment to continuous learning. Learning should be an everyday practice. If we stop learning, we cease to truly live. I have to consistently seek new knowledge. Fortunately, in my line of work, continuous learning is necessary due to evolving technologies and dynamic circumstances. This constant adaptation to new things is something I appreciate. It keeps me engaged and enables me to handle different situations without falling into a routine.

Beyond business, I also seek personal growth through learning. For example, last year I took up sailing, despite having no prior knowledge of it. This year, I have embarked on learning Spanish. Every day, I embrace new endeavors. It doesn't always have to be logically driven. Spanish may not be essential to me, and I could manage without it if I would need to live in Spain. However, I feel an urge to study it, possibly influenced by my desire to immerse myself in the Spanish way of life. Learning a new language opens up a whole new world that was previously closed.

I could continue elaborating, but I believe these are the main points I wanted to convey.

Have you had anything in your life that changed you completely? Some events, some realizations, something that changed the direction you go?

I never considered it from this perspective before. I'm certain that all the events throughout my life have influenced me in some way. Childhood, in particular, is often seen as the most influential period. While I don't have any particularly dramatic childhood events or significant moments from later in life that completely changed me, there are instances where I made decisive decisions.

For instance, during high school, before university, I didn't prioritize studying. It wasn't important to me at the time. Looking back, it's strange to think about it, but I was more focused on sports and other activities. However, there came a point when I had a realization. I stumbled upon a random booklet about universities and the subjects one could study. It sparked my interest, and I decided to redirect my energy towards studying and striving for success. It wasn't that I consciously thought about needing to be successful; it was an internal shift. This realization came rather late, but I began studying diligently and eventually graduated cum laude from university. It all happened in a single day, without any specific trigger or external reason. It could have been a result of personal maturation, but I haven't experienced any dramatic events like that in my life.

What drives you?

I feel the need to always give my best effort whenever I undertake something. Not necessarily to be the best in the world, but to do the best I can at that moment, with the resources available to me. It's a feeling I can't quite explain. Perhaps it stems from my childhood. My parents always emphasized the importance of good grades and success. It could be a psychological need I have.

However, now I think about the reasons behind my actions. There is always a purpose. I don't simply do things for the sake of doing them. One reason that motivates me is the pursuit of financial independence and personal freedom. It holds great importance to me. I want to be able to live life on my own terms, without answering to anyone. I value freedom, and I believe most people do too. It's what drives me to work. Although I have achieved some financial security as I've gotten older and don't necessarily need to work as much, I still choose to because it has become more like a game or a passion for me.

As I mentioned before, the people I work with and the nature of the work itself are crucial to me. I truly enjoy working alongside my partners and continually learning from them. It brings me joy. Of course, there are challenging times, but overall, I genuinely appreciate what I do. I look forward to going to work because it presents new problems to solve and fresh challenges to tackle. The field I'm currently involved in is investing in startups and supporting founders. It feels like a mission in a way, knowing that I'm helping people. As I grow older, these aspects increasingly drive me. It's gratifying to see the impact I can have and to collaborate with like-minded individuals who share a long-term mindset. I want to make a lasting difference and contribute to something meaningful, all while working with people I genuinely admire. That, to me, is the most important thing.

What is more important the process or the outcome?

For me, it's all about the process. I firmly believe that if I concentrate fully, 100%, on the process, the outcome will take care of itself. I don't set specific goals or deadlines, like achieving something by the end of the year or attaining a particular net worth. Instead, I focus on enjoying the process itself, doing the things I genuinely enjoy. By doing so, I trust that the desired outcomes will naturally follow.

It always was like this?

I think the realization came later for me. It was when I started reflecting more on why I do things and why I have a preference for certain activities. I discovered that it's crucial for me to genuinely like and love what I do. This brings to mind a quote by Steve Jobs that resonates with me: "The journey is the reward." To me, this quote encapsulates everything. It emphasizes that the journey itself is what truly matters—there is no other ultimate reward waiting at the end. Have you ever come across this quote? Even if you haven't, I believe you can understand its essence. Steve Jobs actually wrote this on a whiteboard during one of their strategy meetings. I've always held this belief, and I find it incredibly well-articulated. After all, what is the reward? There isn't a tangible prize awaiting us. The reward lies within the journey itself. If you can't derive enjoyment from it or comprehend its significance, then you're approaching it the wrong way. There are numerous cases where individuals achieve something but ultimately find themselves unhappy. They may experience a fleeting sense of joy for a day or two, but it quickly fades away. However, the memories of the process remain—the challenges they faced, the people they collaborated with, and the emotions they felt. These aspects hold far greater importance. It's all about embracing and savoring the journey, but it's crucial to do it in the right way.

Very theoretical question. What would it mean for you to lose your business?

First and foremost, I have diversified my assets. This way, even in the worst-case scenario, where there is a significant downturn, I have spread my investments across various areas, reducing the risk of losing everything. While it could still be a substantial blow if something were to happen unexpectedly, such as a downturn in the market, it wouldn't completely devastate me. I would take it as an opportunity to start anew, venture into a different business or pursue a fresh endeavor. After all, I have investments in other sectors as well. Being diversified is of utmost importance to me as it provides a sense of peace of mind and security, allowing me to avoid finding myself in a precarious situation.

Even if I were to lose everything, it would present a new chance—a chance to build something new from scratch. Rather than wallowing and seeking solace in alcohol or despair, I believe I would be energized and motivated to tackle the situation head-on and find a solution.

I prefer starting over rather than sitting idly. It can be seen as both a positive and a negative trait. On one hand, it means I can't simply do nothing, which is also important at times. People should have moments of rest. However, personally, I find it challenging to stay idle. Even during weekends or leisure time, I tend to have my schedule fully planned, engaging in various activities. Nevertheless, I strive to maintain a balance. It's not solely about work-related tasks for me. I also prioritize sports, spending time with my family, attending to household matters, and traveling. I'm not much of a TV watcher, although I do occasionally watch shows. I find it beneficial as there's always something to learn from these shows as well. Currently, I'm recommending the HBO series "Succession."

Do you a proactive or reactive person?

I believe that I embody both proactive and reactive qualities. It's essential to possess both traits. Being proactive means taking initiative, not waiting for someone else to act, and recognizing the need to solve problems. On the other hand, being reactive is crucial when unforeseen issues arise; you must respond and take appropriate action.

In my experience, I have demonstrated both reactive and proactive behavior within the business realm. Reactive situations often arise in the course of business operations. For instance, we encountered a significant setback when a major investor, who was expected to sign, withdrew, leaving a substantial budgetary gap. It happened a while back, and we had to swiftly find alternative solutions to secure funding. I took the lead in tackling the problem, dedicating myself fully to its resolution. Within a few weeks, we were able to raise the necessary funds from different sources. There is always a solution, and having a supportive team to work with is crucial. Personally, I thrive in a collaborative environment and find working alone to be more challenging.

Do you make decisions based on your feelings, emotions, or some constructive analysis?

It's challenging to determine definitively. I believe that everyone experiences some level of emotion when making decisions. Personally, I strive to be practical and rational, although I acknowledge that emotions often play a role. However, I make a conscious effort to take a step back, breathe, and remind myself to make decisions based on reason. Fortunately, our team possesses a valuable dynamic in this regard. Some of us lean more toward rational calculations, like analyzing facts and figures. On the other hand some of us bring a strong emotional perspective. This combination allows us to complement one another effectively. There is importance of maintaining a balanced and rational approach. Having a team with varied perspectives is advantageous. Emotions should not solely dictate decisions as they can lead to hasty and potentially flawed choices. Sometimes, it is wise to take a step back, give ourselves a day to reflect, and revisit the decision with a clearer mindset. I have learned the significance of this approach through my experiences in helping others, and I find it to be highly beneficial.

How do you feel about people in general?

Generally, I enjoy being around people and have good interpersonal relationships. In fact, I have earned the nickname "Chief Friendly Officer" because of my ability to connect with others. Despite this, I consider myself an introvert. I recharge my energy when I am alone rather than in the company of others. Well, let me correct that statement slightly. I also can recharge my energy in smaller groups, such as with close friends or business partners. However, being in large groups tends to drain my energy. While I am skilled in dealing with people and possess good social skills, it does require effort on my part. I don't naturally engage in conversations with everyone I encounter; it's something that has developed over time. I believe my inclination towards people stems from my overall positive outlook. I tend to assume that people have good intentions, and I make an effort to understand their perspectives by putting myself in their shoes. This approach may have its roots in my childhood experiences. As a small child, I had to develop diplomatic skills to navigate social situations and avoid conflicts. Building strong friendships became crucial, and I believe that has influenced my ability to connect with people today.

Do you hold onto negative emotions towards someone who has treated you poorly or behaved inappropriately towards you?

Yeah, I don't have many people like that in my life. I don't have many enemies that come to mind, which is quite strange. Moreover, it doesn't really bother me. I tend to pay little attention to such matters. If there's someone who seems genuinely angry or upset with me for some reason, I simply move on. I'm not the type of person who would go looking for a fight, unless it's necessary to protect my business or family. If there's nothing to be gained from it, I see no reason to engage. Even if someone says something negative about me, I don't feel the need to seek revenge. It's just not my way of handling things. I'm aware that some individuals always feel the need to get even or prove themselves right. However, I personally assess whether it's worth my time and energy. I prefer to approach such situations in a rational manner and avoid getting overly emotional about them.

Do you do any charity work? If yes, do you share information about this with everyone, for example, on social media?

I keep it for myself. I don't think I've published any of my charities.

Why you didn't publish?

Why do I have to do it? I'm not the type of person who feels the need to constantly talk about myself or share everything on social media. I know, maybe I should be more active on social media, but my focus is on doing my work well and delivering good returns for my LPs (Limited Partners). That's what truly matters to me. I don't care about everything else. Besides, we have a PR team who can handle those aspects. I'm not the kind of person who would excel at being a presidential candidate or anything like that. I'm not very skilled at presenting myself. Perhaps I'll learn it at some point, but for now, it's not my strong suit.

Do you regret anything in your life?

I mean, sometimes I catch myself thinking that I should have done something differently, but I don't dwell on it for too long. It doesn't bring me any benefits or productive outcomes.

What makes you happy?

Yeah, what truly brings me happiness is being able to do the things I do every day. It's like having a routine where everything goes as planned and I take the time to appreciate and enjoy it. My family, my wife, and kids are doing well, and that adds to my happiness. Additionally, working with great partners brings me joy, even when we face challenges. I always remind myself to consider the alternatives, like being in a war-torn place such as Ukraine. Right now, I'm content and fulfilled with what I'm doing. Investing in startups and being in the venture business feels like my true calling. I have a genuine passion for it, and I don't see myself pursuing anything else. I find happiness in the process itself and don't measure it by accumulating vast amounts of wealth.

Do you eat a lot? Do you sleep a lot?

Yes, I have a healthy appetite, and I prioritize getting enough sleep too. I aim to sleep for at least eight hours each day and prefer going to bed early and waking up with the sunrise. In terms of eating, I practice intermittent fasting, but I also don't impose strict restrictions on myself. When it's time to eat, I eat. However, I do have some guiding principles regarding the type and quantity of food I consume.

What is one of the food principles?

I make an effort to eat healthy food by avoiding processed foods. I try to limit my consumption of bread and similar items. However, I do indulge in treats like cake occasionally, although I don't make it a regular habit. My focus is on eating real, whole foods. I include meat, vegetables, and salads in my meals. The key for me is to maintain a balanced diet, and there are times when I eat more than usual.

Why are you fasting?

To feel better. I don't know if you ever tried it, but actually, it gives you very good well-being.

Currently, it has been a couple of months since I significantly reduced my alcohol consumption. I have also been making an effort to consume less sugar. It's all part of maintaining a balanced lifestyle. When you feel good physically, it positively impacts other areas of your life. It holds great importance for me as it allows me to truly enjoy life and find happiness. These aspects cannot be overlooked.

How do you recharge your batteries?

Yes, I actively participate in sports, specifically orienteering. It requires a lot of training in activities. I always strive to improve my skills in orienteering. In fact, I used to be part of the Estonian national team for junior orienteering. There were a few years when I shifted my focus more towards university studies and work, but for many years now, I have been engaged in orienteering. It's an activity that allows me to completely switch my mindset.

After spending an hour participating in a forest orienteering competition, my mind feels refreshed and rejuvenated. It's like hitting the reset button and being fully present. I believe it's important to engage in some form of physical activity. During the summer, I enjoy sailing and exploring different places through travel.

How do you understand the term - 'call of the soul'?

That's like something that feels natural to you. It's not a forced effort. You don't have to exert extra effort because it's aligned with your soul. This aspect is crucial because if something isn't connected to your soul, you won't excel in it. You'll be outperformed by individuals whose work is driven by the call of their soul.

How can people feel the 'call of the soul' and not select the wrong path?

I believe it's important to pursue what comes naturally to you. Otherwise, you won't find true happiness. I understand that in certain situations, it may not bring immediate financial returns, but perhaps there's a way to find opportunities along the journey. You never know until you start. Initially, you may not see the possibilities, but taking that step is crucial. You must follow the calling of your heart. Sometimes, you can even learn to love things. Some people argue against this notion, that you start doing something and eventually grow to enjoy it. It could be any kind of business, even something as simple as being a bus driver. Through gaining knowledge and understanding all aspects of it, you can strive for improvement. It's a possibility worth considering. I don't have a definitive answer, but if it aligns with your plan, I would always encourage pursuing it.

Please share your inner wins because those are the most challenging in our life.

I believe it's more about personal growth and acquiring new skills. It's an inner journey because these skills may not be immediately visible to others. I remember when I had zero knowledge about finance and accounting. It was like entering a completely foreign world, similar to nuclear physics. But I made a decision to learn and excel in it, and that's what I did. There wasn't a specific moment of mastery, but each step of progress felt like a personal victory. For instance, I started as a finance person, but then I realized I needed to learn about business development and sales. So I did, and now I'm confident in raising funds and closing significant deals with investors. It's a visible accomplishment, but it also holds personal significance for me. Looking back, there was a time when I couldn't have done it, but now I've reached this point. It's crucial to put yourself in positions where learning is necessary. We haven't discussed it yet, but I believe it's essential. If you want to excel in something, you have to challenge yourself and embrace the learning process. It's like jumping into a pool without knowing how to swim. You learn because there's no other way. That's the only way I know how to learn. So these victories are more related to the skills I've studied. I learned how to sail and obtained my license, and that was a personal win for me. However, I'm not solely focused on these wins. As I mentioned before, I'm more of a process-oriented person. But it's still satisfying to have these achievements along the way. Currently, I'm trying to learn Spanish, and my ultimate victory would be to have a conversation with Cristobal in Spanish. That would be a significant accomplishment for me.

Could you please share with us the principles you are following?

1. There is no secret to success, only hard work. There is no secret.
2. Don't half-arse, do the work. If you do something, do it properly.
3. Even if everything is going terribly and you have no reason to be confident, just decide to be whatever you want to be. Always stay confident, everything is a game, and we are actors in that game.

Regarding the last principle - many people have a lot of doubts, and that guide talks about avoiding this. Can you share more details?

I believe having doubts is natural, but it's crucial to maintain self-confidence and the belief that you can overcome challenges even in the face of adversity. For example, when you're in sales and facing constant rejections or running low on funds, maintaining confidence is key. Trusting in yourself and your abilities can make a difference, and I have personally seen it work.

3. Take risks, and you will get the payoffs. It may sound simple, but taking risks is essential. Without taking risks, it's difficult to accomplish something significant in life. Risk-taking is crucial. It involves putting your money and reputation on the line, and that's the only way.
4. Learn from your mistakes until you succeed.
5. If bad things happen, see them as opportunities. Instead of reacting negatively, I view it as a positive occurrence. It happened for a reason, and it provides a fresh opportunity and chance for growth. It's not easy to think this way, but it's the truth.

I strive to adhere to these principles, although I'm not perfect at them. It's something I consciously try to do. As I mentioned earlier, it's important to remember that the journey itself is the reward. If you're not enjoying it or having fun, perhaps it's time to consider doing something else. Ultimately, it's all part of the game of life.

6. It's crucial to have a winner's mindset, even during tough times or when faced with setbacks. Consider it a victory to keep pushing forward, refusing to stay defeated. Regardless of the outcome, maintain a mentality of resilience and determination.
7. Additionally, it's important to think big in everything you do. When embarking on a new endeavor, challenge yourself to envision grand possibilities. There's a saying that encourages thinking even bigger, and I often remind myself to adopt this mindset when making decisions.

Do you have any person, or have you had someone who influenced you a lot?

I believe my parents have had a significant influence on shaping who I am today. Their impact on me cannot be overlooked. They are definitely the biggest influencers in my life. Moreover, my wife has played a significant role in inspiring me to become a better person. Additionally, I mentioned earlier that my partners have influenced me greatly, and I make it a priority to spend ample time with them. There are also individuals I have read about in books who have left an impression on me. I can't neglect the influence of my friends and co-founders in my first startup, Rando and Priit. Rando, who is now leading CMO secondary fund, has taught me valuable lessons in networking and sales. Priit, on the other hand, has helped me develop my problem-solving skills, particularly in complex situations. Now I am learning a lot from my partners Herty and Cristobal. I firmly believe in learning from everyone and try to gain insights from each person I encounter. Ultimately, it's about improving my decision-making abilities, which encompasses all aspects of life.

Do you read books?

I make an effort to read, although I often find myself lacking sufficient time. There are occasions when I manage to read just a page or two before dozing off. Nevertheless, I strive to read on a daily basis, even if it's only for a short while. Currently, I'm engrossed in Annie Duke's "Thinking in Bets," a book that explores decision-making through the lens of poker and its application in everyday life. I have a penchant for reading biographies of various individuals to understand the factors that influenced their lives, their driving forces, and their decision-making processes. I find it fascinating to delve into real-life stories, discovering what truly unfolded.