People know you as a former startup founder. Many saw you on a stand-up comedy stage a few months ago and heard you give a keynote at the last sTARTUp Day. How would you introduce yourself? Who are you?

I take on roles in these activities, but they are not me. For example, I am a startup founder but that is not what defines me, it's just one of the roles I have taken. A year ago, when I left my startup, I thought about this a lot.

When I compare myself to my past selves, I haven't changed much. My roles, mindsets, and actions have changed. I think it's true that people don't change, but their mindsets and actions do.

I'm interested in many things and have a great desire for discovery and creation, which is reflected in various DIY topics—cooking, woodworking, and construction. I enjoy creating things myself during the discovery process.

For me, design is about thinking up something and solving a problem, but design, by definition, does not involve execution, although I’ve always coded as well. For example, if you are an architect, the house is ultimately built by the builder. In my case, I also have a passion for executing the design myself, for example, by designing and building furniture.

I am better at starting things than operating large-scale projects. In the startup world, it's rather rare for someone who is good at starting something new to also lead a 1000-person team. Inevitably, different types of people are suited to fill these roles.

When you think about design, do you see yourself more as a specialist or a generalist?

Definitely a generalist. I've had specific titles like UX designer, but in practice, I do a mix of everything and tend to lean into different areas during different periods - products, branding, websites, and storytelling. Professionally, I've always liked identifying as a designer, even though I don't fit into the traditional design roles anymore. I need some variety.

However, the designer title can cause confusion, especially outside the tech sector. People might think you're a fashion designer. But I like the broad term and have kept it general. I usually introduce myself as a designer and entrepreneur.

People often see design as making things beautiful. While that's important, design is primarily a problem-solving methodology. The problem might be an unattractive brand that doesn't connect with customers, so it needs to be made appealing. In user experience design, the focus is on user journey and convenience, not just aesthetics.

For me, creating a startup was a design project on a larger scale. It starts with a problem that you want to solve, then you explore user behavior and desires. Then you design a product or service as the solution. Next, you design your team and an office that's comfortable for everyone. You need to design meeting structures that are effective and time-efficient. You design an imago, recruit, and so on. Its all a creative process involving lots of design and craftsmanship.

You were interviewed on the sTARTUp Day podcast when you had just left Remato and were preparing to go on the sTARTUp Day stage. If anyone wants to know more about your startup journey, I recommend listening to the podcast.

You left the position of CEO at Remato a year and a half ago because you felt burned out and needed a break. Is a year enough to recover from burnout? What has this year given you?

A mentor once told me that burnout is the body's reaction to being in the wrong place and needing a change. The way you're currently operating isn't working, and if you don't consciously make a decision to change, your body will eventually hit the brakes and force you to deal with it. If you go through burnout by simply resting until you feel better and then return to the same situation, it's only a matter of time before you're back in the same or even deeper trouble.

It's easy to develop substitute activities that help numb the feeling. For me, it was computer games and, to some extent, alcohol, which I didn't consume excessively but for the wrong reasons.

About a year before the decision, I realized that something was wrong. At first, I didn't dare admit it to myself and swept it under the rug. There were many aspects, but mainly, I felt that the construction field wasn't for me. The potential to eventually make a lot of money was tempting, but it wasn't actually motivating for me.

Another thing I discovered was the desire for external praise and recognition. If you do anything well in the startup world, you inevitably get attention. It helps the business if you enjoy the attention. I've always had a bit of a drive to be on stage—I made music in school, then got into startups and stand-up comedy. But doing things just for that reason is not good..

Today, I'm not burned out; I have energy and motivation.

You recently participated in an exciting project where ordinary people were trained to become stand-up comedy performers in six weeks, and together you put on 15 sold-out shows. What did you learn from this process?

This was a joint project by Kinoteater and peaasi.ee. Initially, it was a mental health comedy writing workshop that caught my attention because mental health is important to me, and making jokes seemed like an interesting new topic. I applied, went for an interview, and out of hundreds of candidates, I was chosen along with 21 others.

The six weeks of training began with mental health first aid lectures and continued with exploring the structures and setups of jokes. It was fascinating to look at jokes from a technical perspective. I used to think some people were naturally better at making jokes and telling stories, but this workshop proved to me that everything is learnable. Secondly, it's much more technical than it might seem on the surface.

So, how do you write jokes?

A joke should be a surprise, create a small shock, or push boundaries. You can make a joke by saying something or telling a story as the set-up and then follow with a punchline, or you can build a long setup with a series of jokes. Later on, you can refer back to the earlier parts and do callback jokes.

In the beginning, we were told not to force ourselves to write jokes right away but to simply explore topics and look for absurd connections. We were taught many different practical tips on how to explore topics and search for jokes, one of my favorites was mind mapping – you start with a topic and write down various keywords. Then you make another round where you take each keyword and write down more keywords related to it. Now, you cover the middle circle and try to create connections between the first keyword and the outer circle's keywords. Then you add a new layer, cover the middle keywords again, and try to find a way to connect them.

In the end, each participant wrote about a 5-minute set, which we performed at the end of the course. A few weeks later, we received an email saying that the project had gone so well that they wanted to put together a stage program and asked if I could join. Twelve people were selected for the stage program.

When you participate in a pitching competition, you only have one chance. Here, it was interesting to really experience the process – every audience and performance was different. When I changed the wording, the audience reacted completely differently. Sometimes just changing my posture or tone of voice was enough to get a completely different reaction. The first and last performances were entirely different.

For startups, I also recommend that you don't begin talking to investors and raising funds with the most valuable investor. Start by doing your homework and compiling a list of contacts, working your way up from the bottom, leaving the best for last. In the meantime, you'll have a chance to practice your pitch and make significant progress.

You have a strong background in design, having worked as a UX designer at Booking.com. What unique advantage does this skill give you as the new program manager of sTARTUp Day? Are there transferable skills?

The most transferable skill is probably the designer's mindset. I look at the profile of the sTARTUp Day attendee, what interests them, and what their motives are, and then start shaping the experience and solving problems. To solve a problem, you need to do the preliminary work and get to know the attendee and their problems and goals as well as possible.

If the ideal client isn't defined, it's like you're trying to cater to everyone, resulting in a mixed-up offering where each customer finds only a small corner of the product suitable. I view the stage program in the same way, ensuring it has a focus but maintains some flexibility by including topics that resonate with different people.

A common mistake, especially among younger designers, is giving too much weight to their own opinions. The only important thing is what the user group likes. In designing the program my advantage is that I can use my experience as a startup founder.

It's definitely challenging to draw the line between personal preference and trusting your own intuition. Over the years, you develop a gut feeling based on experience.

It's important to have the courage to make changes if something that has already been done turns out not to work for the client. Sometimes it takes three months of work, but if the solution isn't actually of interest, it needs to be scrapped. The true value is in being able to make such decisions.

It's crucial to have one person with a clear vision in mind, otherwise, it's easy to end up with compromised solutions. These compromises are confusing for the end user because they are neither one thing nor another. Of course, teamwork and collective contribution are very important, but at some point, decisions need to be made, and lines drawn to determine which option best fits our vision.

What are your ideas and wishes for the sTARTUp Day 2025 program? What new elements would you like to introduce? What do you think already works well?

I want to bring in international experiences and stories that aren't always pretty because behind these non-success stories (and success stories) are really tough journeys. I'd like to bring some major failures to the stage. Success itself doesn't teach people much.

I remember waiting for someone from the outside to tell me what to do next. But no one does – you have to experiment on your own. It's worth absorbing as many stories from other entrepreneurs as possible because there's so much to learn from them. But often, people don't want to share these stories freely; they come out after a few beers.

You're a veteran when it comes to attending startup events. What is your advice on how to best hack a startup event?

The most important hack is to build relationships. Talk to people, share your stories and concerns, listen to others' stories, and join the conversations. You'll find many like-minded people around you, which helps in creating natural relationships. Opportunities happen when you let them happen. Show up with an open mind and go along with the things happening around you.

You don't have to be the one who is always actively talking. Just being in the circle and listening to how others talk is enough. Especially when you're new to this sector, start by getting to know some people, even just by name, or see them on stage and remember that this person with this name and face is running this type of company.

I saw this repeatedly at the beginning of my journey – I learned that certain people existed in certain fields, and later, when I felt the need, I could reach out to them and ask for advice. Fortunately, the Estonian community is very open and supportive.

What has been your most memorable sTARTUp Day moment?

I’m not sure if this is the most memorable but the first thing that came to mind was from the last sTARTUp Day. It was one of the traditional unofficial investor parties, and it was around 1 AM. There was a group of founders just joking around and sharing stories about how hard 2023 was, and then Kristjan Maruste quoted I think Indrek Kasela saying, "Running a startup is so twenty twenty two," which was so fitting and funny at that moment. For some reason, this simple moment came to mind.