Bogdan Iordache on FOMO, self-improvement, and 15 years of the How to Web conference

“Developer turned founder, turned investor,” Bogdan Iordache, has a unique insight into the world of startups, especially the startup landscape in Eastern Europe. As the founder of the “How to Web” conference, one of the earliest and longest-running startup conferences in Europe, and now the founder of Underline Ventures, Bogdan is committed to working with and championing founders. From failing in his first attempt to set up a startup, to stepping in at short notice to pull off the first edition of the “How to Web” conference, to striving every day to do his very best, join me as Bogdan shares his stories, his fears, and his motivations for the future.

Thank you so much for joining us today.

Of course! I had to do this interview. Especially since I saw your LinkedIn post where you were presenting your ventures in Thailand. That struck me as something quite interesting for an investor to do. Although I totally agree that entrepreneurship is a hand-to-hand combat, very much aligns with what I think about being a founder. We also chatted over some calls and we finally met at “How to Web” (the first international start-up conference I co-founded in Bucharest back in 2009) last October. Your ability to connect people and think in terms of networks is a great gift.

Thank you, like-minded people always find each other. Can you tell us a little bit about your story up to now as founder and investor?

I’m a developer turned founder, turned investor, or as I introduce myself to fellow developers, a failed developer. I graduated from computer science studies, then studied at a university in France, then got back home and started my first company, which failed spectacularly after one year. Then I started my second company, which went a bit better, and I sold it in 2013. It was a small exit, nothing major, but the first exit is always the sweetest. And then I started working in investments at a local fund, then moved to the UK, and back to Romania. And from 2022, I’ve been running Underline Ventures.

So that's the backstory. I also started a conference “How to Web” with a bunch of friends back in 2009. The first international edition was in 2010, making it one of the earliest startup conferences in Europe and one of the longest-running startup conferences in Europe. And we're doing this in Bucharest, which is a difficult feat on its own. We are now organizing the 15th edition. We are super happy to connect founders and operators from the technology world. It has now become one of the top five startup events in Europe.

What drew you into the world of startups?

When I graduated in computer science, I didn't want to get just another job as a developer. I wanted to build stuff on my own, so I passed on whatever jobs were on the market back then and I just started tinkering with different products. I think that was one decision moment that pushed me into this new world, but back then I didn't know I was building a startup. It was 2004 and I was not that well connected. I didn't know that this was a startup that I was doing. What got me into the startup world was the LeWeb in 2008. This amazing startup conference was held in Paris and it was the biggest startup event in Europe, with 1,700 people – half of them were Americans, so it was a great place to connect with the startup world from the US. And quite expensive for that time. So I booked myself a ticket for LeWeb in 2008 and I met the startup world. Lucky enough for me, I also met two Romanian founders, who I didn’t know in Bucharest: George Lemnaru from Green Horse Games and Vladimir Oane from DeepStash, and those guys have become two of my best friends. I invested in George’s -startup in 2013, the one he had when he was at LeWeb. When he sold that company, he was my anchor investor for Underline Ventures. So I can trace what I'm doing right now with my life back to that moment 16 years ago. That world was so dynamic, so creative, so crazy, so fresh. Everybody was doing something exciting. My biggest worry back then was that I would not be able to be as good as all the others in the room. And that I would not be able to be part of this world for very long. I think the startup folks today are much more balanced and very much closer to normal people, but the pioneers from 20 years ago, half of them were mad - and that was beautiful in many ways.

Talking about the fear you mentioned before, it's a fear that many people share. There are a lot of smart people in the room and often people don't feel they are as smart, creative, or entrepreneurial enough. How have you overcome this?

I haven't, I'm not even joking. I haven't. I don't take for granted what I'm doing. My biggest fear is that what I'm doing is just not good enough, that I have to be better at what I do and I'm really honest about this. This is not some personal deterrence. I am doing my absolute best to do my best work to improve myself and help the others around me do better work. That's my 110% focus all the time.

Where does this mindset come from?

This fear of always missing out on something? Honestly, I just want at the end of my life to be at peace with myself that I've done my best most of my life. And that's it. It also comes from the fact that my parents were pioneers of entrepreneurship in the ‘90s in Romania. It's a period very hard to imagine what capitalism looked like in the ‘90s in Eastern Europe after the fall of the USSR. It was sort of like the gold rush in the US.

Everything is super risky. People were betting on their homes and even their lives on new businesses. So, if you go through that as a child, I think you are just more comfortable with taking risks, you don't feel too much pressure when you're taking risks. You probably wonder what that was like and whether it was wise for people to risk so much. It probably wasn’t.

When I started my first company, I had to send an invoice to a customer and I wrote my invoice on paper. That was the process back then in Romania. When I started my first thing, that was my level of competence. I couldn't even put together a basic invoice, but I still did it, right? So that's why you sort of ask yourself - was I prepared to start doing that? Probably not, but you do it anyway.

As you say, you're never 100% ready to start something, so you just start and see how it goes. What did you learn from your first attempts at building a startup?

I lost money, and that was not nice. I think I learned to be more customer-centric. And I, sort of, learned the discovery bit. Building something, then validating that, then building more, and getting it going in the right direction.

When I graduated from university, it was the biggest gig that you can imagine. I had no prior proper business knowledge or anything like that, so that was a process in itself. Figuring out how to make things that are valuable for your customers. Engineers are very much trained to focus on hard engineering problems. But to focus solely on this would be stupid, as these problems are insignificant for your customer. Hard engineering problems don't always correlate with business value, most of the time they don't, actually. Sometimes engineers can solve totally meaningless problems and they can become super important, 20 years later. So, learning to navigate what you're doing and prioritizing stuff based on business value and product value rather than just things that are difficult to solve is something that I learned, honestly, the hard way. I'm not that smart.

What are you running towards at the moment?

With Underline Ventures, ?I want to put together a fund that can deeply support founders when they build startups. You can split this into the support of more experienced versus inexperienced founders, founders who create companies that sell in the local regional markets versus the global market…. So there is a lot of variation about what a useful fund means, but that is my focus right now. I think that the world is moving forward with people who are not afraid to take significant risks and just bet their life or their careers on something that they are obsessed with trying to solve. I want to be a good partner to these people and help them achieve amazing things in their lives. This is what I'm doing right now. We work with founders who need an intellectual partner to discuss their priorities with, to understand their business better. Some founders need support in hiring key people faster… There's always a mix of everything. I haven't been able to cut this down to a very niche value proposition, and I'm not sure I want to do that. I’m not sure about verticalization and being super specific with what your fund is doing is what you should aim for.

For now, you're providing support in those different areas. How does it work between you and the founders?

So far, we've been doing well because even though we have a small fund, we have managed to put together a strong platform team. We have people on our team who help with hiring, communication, growth, market analysis, financials, and all these elements. Then you have our extended network. As a founder, I have 15 years of experience I can deploy, sort of a larger network that can help with any problem that you may face.

But for me, the rule of thumb with every founder that we work with is that I am allowed to tell them everything I can think of very directly, and they are allowed to ignore me if they think that what I'm saying is bullshit. And that's absolutely fine. I’ve got to have no limits to what I can tell the founders because in this way we can get to some relevant conversations. And that's also because, apart from very technical advice, founders also go through a personal journey. When you invest in a founder at pre-seed, most of the time, they don’t have the experience or the knowledge. The personal dimension is different from how that founder, if that business is successful, will look five, or ten years later… when he or she has to manage a company that's worth hundreds of millions or maybe billions. It's a personal journey, it's a journey in which the founder has to develop along with the company. And that's also a very important aspect that you have to address when working with founders. And that's even more relevant, I think, as in Eastern Europe- founders - don't have the context that a founder from London or Berlin has. They don't have thousands of people around them who have already done this. So they probably don't know what success looks like, how to reach success, how to put themselves in the right mindset, etc. That’s also important to address as that's how our relationships are built.

How does your work with Underline Ventures and How To Web help founders and entrepreneurs in Eastern Europe?

They're sort of two sides of the same coin. Because with both of them, I'm trying to build products that help founders build their companies, have a broader vision, a better understanding of the market, a bolder vision, and connections to people who are relevant to them. This is mostly the conference, right? And then with the fund, you provide them capital and more hands-on support to do the same to build that business. And at the end of the day, they build the best version of themselves.

What kind of sectors are the startups you are working with, working in?

Everything. So, we have a few areas that we are looking at more carefully right now, but we don't have a specific sector that we are exclusively interested in. So a few of the verticals that we have invested in are related to enterprise automation, cybersec, agritech, and a few AI startups. But we also have some stocks, for example, which are very different from all the others -in our portfolio that we are looking into more deeply, like industrial tech, and defense tech startups, which are super interesting for us at the moment.

What are the key criteria you're looking for when it comes to considering investing in some startups?

Our investment criteria revolve around identifying exceptional founders tackling significant problems in sizable markets. We place a strong emphasis on the founder's understanding of the market, their ability to build superior products, and their experience and networks within their industry to build a great culture going forward. Additionally, we evaluate market trends, business models, and potential for value creation.

I wanted to move towards the “How to Web” conference. So how did you decide to start it? And were you alone or with the two founders you found this conference? How did it work?

I was just really frustrated by the fact that we had no significant connection with the good world of technology back then. We had some events that were put together by great folks in Bucharest, but they were very much focused on local speakers in Romania. Somebody read a book about startups and they came and talked about how to build startups based on that book, but nobody did that thing. So, “How to Web” was just born out of that frustration. We wanted to do something that would help our peer founders in their work. It was put together by a larger group of friends, but after the first event, it became a bit smaller. I was not even the one who should have managed this, because I had a different company. I was running my own company. But we started things and then the person who should have been in charge had some personal issues and she had to drop out. I was too embarrassed to tell everybody that we were going to cancel and that's how we did the first edition. And actually, we lost money organizing for a long time.

In these 14 years of the conference, you also went through the COVID and post-COVID times, what do you think has changed for conferences like yours?

Back in Bucharest when we started the first conference, there was no investor in Romania doing investment in startups. So for my previous startup, I only got one investment offer, which was $10,000 for 51% of the company. And that was a company that had a product, customers, team, technology, etc., so it wasn't easy. That was the environment back then. Now you have multiple funds operating in Romania. You have tens, maybe hundreds in Eastern Europe and thousands in Europe. Let me tell you, everything has changed. It's a different universe. It's what we had back then multiplied by a million. It’s incomparably better for founders what they have right now.

15 years ago, it was unclear what a startup was. People would assume a startup is a company so they would keep this discovery process, which is very common now. When you started a startup, they would just assume that whatever they were thinking needed to be executed right and that was it. But in reality, what makes a startup special is their capacity to adapt very quickly and this is something that has been learned at scale everywhere. There are still mistakes being made but still, this is way more common knowledge than we had 15 years ago. So this is the main thing that has changed.

What skills do you think startup founders need today?

I think there's a much better understanding now of how to build super innovative products compared to 15 years ago. Back then, almost anything you did was new, addressing verticals that were just emerging, and there was a plethora of new technology to experiment with. However, the innovation component is less critical nowadays. With so much technology available, you have to deeply understand the value you're creating.

It's harder now to build something significantly better than what's already in the market. You also need to consider distribution from day one because different distribution channels can affect the market in various ways, even for the same product.

According to the How to Web 2023 Report, last year was a big one for AI startups. What do you foresee for the start-up world in 2024?

I anticipate even more focus on AI in 2024. The foundational AI models may become less interesting as they're costly to train, and differentiation is limited. However, the demand for data and AI infrastructure, including tools for creating data pipelines, customizing models, and testing model safety, will grow significantly. We'll also see more specific use cases of AI across different verticals. And then there are AI-generated videos, which is something we don't know how much will move forward, and how significant it will become. Will it be good enough? You can do commercials with it, you can do music videos, you could do entire movies. How good will that become I don’t know, but there are a bunch of other areas that could be impacted by that as well.

Looking ahead - how do you think the geopolitical situation will affect investments and startups in Eastern Europe in the coming months and years?

That’s a really good question, and I think about it daily. The past couple of years have been relatively calm in terms of investment in Eastern Europe, which was a positive development. However, the recent Russian invasion of Ukraine has created uncertainty. If Russia were to succeed in Ukraine, they wouldn't stop there, which could have significant implications for the region. In addition, with so many elections happening worldwide, it's hard to predict where we'll end up by the end of the year. Honestly, I have no idea what might happen.

Thank you so much for your time, Bogdan!