The Perfect Exit, Founder Stress & Why "Nice Guys" Fail | Bart Vandekerckhove - Collibra

Shamil Malachiyev: Good morning, everyone, and welcome to this week's episode of the Founder's Code. My guest this morning is a data analytics guru who, after leaving the data intelligence company Collibra, started a data security startup called Raito. And guess what? He sold it back to Collibra just four years later. Please welcome Bart Vandekerckhove. Hi, Bart.

Bart Vandekerckhove: Hey Shamil, thank you for having me, and congrats on pronouncing my last name correctly.

Shamil Malachiyev: I've put a lot of effort into making sure I pronounce it correctly. Can you tell our listeners and the viewers a little bit about the work that Collibra does and the work that Raito did?

Bart Vandekerckhove: What Collibra does is it basically helps organizations consume their data. Either it's by exposing their data to AI agents and large language models, or by more traditional ways, like reporting and insights and so forth. That's the way I try to explain what Collibra does, because that's what data governance does. I try to avoid the term data governance, because people's eyes glaze over, and when you go into the details of what data governance is, they get even more bored. That's why I talk about what our customers try to achieve with Collibra and its suite: to get value from data. And a lot goes into that before you really can get value from data. It's often underestimated. But what we see now with AI is that people are starting to understand that in order to get value from data, we actually have to do data governance. Hence you need Collibra, which is the best in the market.

Shamil Malachiyev: And regarding Collibra, can you first explain the scope of the company, how big it is, which markets it operates in? Let's start with that.

Bart Vandekerckhove: Collibra, the last time it was valued, it was multiple billions, so it's definitely beyond a unicorn. A well-established market leader in data governance. In terms of employees, we are more than a thousand people, and we operate globally. In terms of customers, it's typically the large enterprises that need to use data to be productive. But we also see smaller organizations. Well, still large. We see, for instance, a player like Zalando: a pure data-native, cloud-native company. Data is core to their business. If you go to their website, it's all about data, it's all highly customized to you. In order to make that work, they need data governance, and they go for a product like Collibra. So large banks, large pharmaceuticals, large governments, but then also very agile, smaller vendors. For each of them, data is at the core of their business.

Shamil Malachiyev: In simplistic terms, when you refer to governance, how would you explain it? What does governance involve, especially with an enterprise-level customer holding a lot of data?

Bart Vandekerckhove: I'll start where it used to be, and what organizations are pivoting away from. What governance used to be really is in the word: trying to govern, trying to police. That's what it was like five to 10 years ago. Data governance sat in their ivory tower and was policing you on whether you were using data in a compliant way. It was all regulatory-driven, and that's no surprise, because the main push for data governance was initially regulatory, after the financial crisis. You had BCBS 239, a regulation for banks on how to properly govern data. So if you're listening now and you're already starting to fall asleep and your eyes are glazing over: I get it. That's where data governance is coming from. It's really from policing, bean counting, trying to get hold of the business, and in that motion, slowing down the business.

But in the meantime, a lot has changed. When data governance started, data was still largely a by-product of business. In the meantime, data is core to the business for a lot of organizations. So data governance is shifting from being a police officer to being an enabler. A lot of people say that: we need to be an enabler, not the police. Security says similar things. And for data governance it means supporting the business. It means making sure that your data is trustworthy and of high quality. In essence it means: each time somebody needs data, and it can be your AI agent, or it can be you needing to build a report, you're putting all the effort in place for that person to find the data, the right data, with the right definitions and of sufficient quality. And you need to make sure that when you're using that data, you're in compliance with regulations, whether it's privacy regulations or security standards.

Now, what does finding the right data mean? Because it can sound abstract: I just go to my database and there's a customer table. Well, a customer is a good example. Depending on who you ask in the business, a customer is somebody else. If you ask sales, and if there are salespeople listening, they will hate me for this: sales quickly qualify somebody as a customer, because it drives up their quota. For finance, a customer is somebody who has paid the actual invoices. So it's a world of difference what that is, and it's also reflected in the data. If you have to build a report for finance on customer performance, you're going to use different tables. You really need to understand what the data is, who owns it, what's the definition, where in the life cycle of that customer this customer is, because that really impacts performance. If you don't do that, and management asks three people for a number, what was revenue this year, all three will come back with different numbers. That's not good if you want to really make data a cornerstone of your business.

Shamil Malachiyev: Not long ago I was reading a post on LinkedIn about a guy who uncovered that for the last three months the whole company had been operating on data which was hallucinated by one of the LLM models. They were even putting out forecasts and having meetings around that, and only recently he realized. Just to show how important having the right data and securing the data is in today's world. And can you tell us then about Raito?

Bart Vandekerckhove: The initial idea came into existence when I was still a product manager at Collibra, in 2017, 2018. By the way, I'm a big privacy nerd, big security nerd. I saw that you had GDPR coming, with very strict requirements on how to use personal data. And the fines are huge. People are underestimating the fines, but the last time I checked, several months ago, they are raking in the fines. It's a data tax.

So I was working on privacy and I was talking to privacy teams, and what I noticed was that privacy was also managed in a siloed way. The legal team were using their tools to get consent, their register of processing activities, their privacy policies and so forth. And they were just documents, paper tigers almost. I thought: there's a huge distance between privacy policies and how the data is being consumed. In terms of systems, there's a complete disconnect. So I thought: hey, we need to find a way where it becomes very easy to immediately, dynamically enforce those privacy policies where the data consumption happens. Because now there's this huge translation, it costs a lot of effort, the wrong people have to do it, you don't have visibility, there's no ownership. So it doesn't really happen. Or when it happens, it's too repressive: if people manage to enforce it, it really prevents people from accessing the data, consuming it and being innovative. And that was the balance: either you were compliant with your privacy and security policies, or you weren't, but then you could use the data. This was a false dichotomy in my mind. You need to be able to consume data while also being privacy and security compliant. That's where the idea initially came from, as a product manager at Collibra.

I didn't really get it as a priority at Collibra at the time. Most organizations weren't there yet. Most organizations weren't thinking of operationalizing their privacy policies. In terms of timing, it wasn't the ideal moment for Collibra, so I couldn't get my engineers. And as a PM, if you don't get your engineers, you get frustrated and you throw tantrums. And it was also COVID, so I was at home. I had a lot of time to think. And I remember vividly, I was thinking how huge this opportunity was. I was also thinking: well, I've been an employee for 10 years, the past 10 years since graduation. What do I want to do the next 10 years? And with COVID, I thought: let's go for it. Let's just start a company. So I immediately gave my resignation at Collibra and started Raito. At the time, Raito was just me and my idea, which was very conceptual. I had no understanding of how data warehouses worked. I didn't know what Databricks was. I didn't know what AWS S3 was, or Redshift. Zero technical knowledge. And I started selling it.

Shamil Malachiyev: Can you go to the start? As a founder, I know the initial stages are research: the first thing is to know what you don't know. You identify: okay, I have nothing on these kinds of concepts and companies. What was that initial experience like, needing to study all of these things and put them together? This is, by the way, before we had Claude, where you can just throw things into it and it explains everything to you. You had to do all of that research manually back in the day. Can you talk about how those days used to go for you?

Bart Vandekerckhove: They were fun, man, they were a lot of fun. How did I do it? Let's say I was not the brains in the operation. When I found my co-founder, I found the brains in the operation: a very, very brilliant CTO co-founder. My approach was just try and sell. Because I knew the problem was there. That was validated at Collibra. Well, no, it wasn't validated at Collibra: I knew that it was going to come. So I believed firmly in the problem. I knew that data consumption was only going to increase; we're going to use more and more data. But I also knew that the importance of privacy and security was going to grow. At the time, people were using Excel files, and people called me crazy. They said: we just do it with Excel. But I was convinced that with consumption of data becoming so important, privacy and security would also become more important. So I didn't doubt the problem. How to validate the solution: there, honestly, I was shooting blanks. I just went and tried to sell it. I went everywhere and started making noise. I would engage in fora, I would talk to people, I would write, I would try to sell it, I would try to find partners. I was just talking, talking, talking to people. And in these first conversations, I should have taken some screenshots: people were, in the most polite way, correcting me, because I would say the dumbest things, and they would correct me, and I would learn from it.

So that's my approach: really just go and sell it, try to sell it, and learn and adapt and improve. And in the meantime, of course, work on the technical knowledge. In the meantime, I know how Snowflake works, I know how Databricks works, I know how the systems work, I know how the architecture is set up. I didn't know that then, but that shouldn't prevent you from starting. You can learn that stuff. You just need to buy the time to learn. So if I would have to summarize it: make sure that time is an ally, because you need time to learn and improve. That's basically it.

Shamil Malachiyev: And how long until you found a CTO and you made the decision that you were going to do it together?

Bart Vandekerckhove: It took me almost a year. So imagine: I'm selling this stuff, or trying to sell this stuff, for more than a year without a CTO. The objection that always came back, and I was even trying to raise funding without a CTO, was: where's your CTO? Who's going to build this? But from the start, I knew it had to be Dieter. That was the former CTO, now our engineering manager on data access. I knew it had to be Dieter because of what he did at Collibra: he basically built the modern version of Collibra. This guy can build. He's a machine. The engineers beneath him operate like crazy. So I knew: this has to be the guy. But it took me a long time to convince him. In the meantime I was trying out with other people, but it needs to be a match, and I couldn't find an exact match.

Shamil Malachiyev: What were the qualities you were looking for, and what were the red flags with the other matches that didn't come through?

Bart Vandekerckhove: The drive. The drive to just do it, basically.

Shamil Malachiyev: Because during interviews everybody's like: yeah, I'm ready to work 24/7, this is a cool topic. But then when you start working...

Bart Vandekerckhove: Yeah. But you start working. So there are different gradations of how involved they are. Some are just talking: let's do something, and it stops. Naturally, they follow the funnel. Other people, you start playing around with a project together. I was talking to somebody who was the CTO profile, but he got a very nice position, so he went for that position. That didn't work out. Other people are in it for the job security. And you have to understand, for a lot of technical people, definitely the CTO profile, they can easily have job security with a very nice salary. So finding that person that is a very good CTO, who will often have that job security, willing to do this, in a country like Belgium, is very, very hard. Now there are a lot of young entrepreneurs that are doing this, and I love that. But when you look at people of my generation, and in the meantime I'm not the youngest anymore, you'll see that among us we're a bit more conservative in making that jump.

Shamil Malachiyev: Yeah, we appreciate the stability, especially after surviving COVID, the AI age, the financial crisis. All of those steps teach people to be more risk-averse, to be more careful.

Bart Vandekerckhove: Crisis after crisis after crisis. Yep. I look at it a different way. For me, crisis is volatility, and hence opens up opportunity. But I also understand that you're a bit more careful with all those crises. Makes total sense.

Shamil Malachiyev: To understand your psychological portrait, can you tell us a bit about where you come from? What were you like growing up? Did you show any signs of: risk? Love it. Let's go do some entrepreneurship.

Bart Vandekerckhove: No, opposite, opposite. I was a daydreamer. I spent a lot of time outside climbing trees and stuff, but most of the time I was just in my mind, fantasizing. That's what I did as a kid. As a kid I always wanted to go into the arts. First I wanted to be a graphic designer. Then I wanted to be a movie maker. Until my twenties I had my rock band; I wanted to be a musician. I always wanted to be in a field where you connect with people through art, where you share emotions. That's what really interested me. Of course my mother, who did most of the upbringing and the raising, bless her heart, she had so many stressful moments. She was always pushing me toward more common sense, toward getting a solid degree first, which I did, in business, and then you could always venture. And I do feel I would have made a crappy artist. So in that sense, my mother was definitely right.

But a lot of entrepreneurship really requires creativity, and that brings me back to your previous question about the CTO, about who you work with. I think you need stellar opposites. Where I was more about connecting with people, trying to sell it, trying to market it, trying to find the right colors and messages and words, in as short a space as possible, to bring you to the vibe and the values that we stand for, my co-founder was about: how do I build this? He had to be way more practical. If you're both dreamers, it doesn't work. If you're both about how do we get shit done and make this in practice, it also doesn't work. So when looking for a co-founder, I think you need to find a person that is the stellar opposite of you, but shares the values. Dieter and myself, although we're in almost every way opposites, we do share the same values. Values like honesty are very important. When it became very difficult, and we've had difficult times, like all startups, you go through times where you're just grinding your teeth from the pressure...

Shamil Malachiyev: Why the hell am I doing this?

Bart Vandekerckhove: Yeah. In those moments you're exhausted, you're emotional, you can get into conflict with your co-founder. But even in these very, very difficult times, where we were close to opposites, we still went for communication. Because we had those shared values, we could still communicate in those very, very difficult times. And I think that eventually was a foundation for, I would say, the success of Raito, because we did eventually a nice exit.

Shamil Malachiyev: Can you talk about those foundational values? You've mentioned honesty is one of them, being able to have tough dialogues with your co-founder. Maybe there are some others you can pinpoint that helped your co-founding relationship survive those tough times.

Bart Vandekerckhove: I think honesty was the most important one. We had some other values where we talked about openness and directness, and being kind, I would say that one as well. So openness, being honest, but also being kind and respectful.

Shamil Malachiyev: What is being kind, for you?

Bart Vandekerckhove: Everybody's flawed. Everybody has a day when they're down, tired, not thinking straight. And you might try to say your opinion, but instead of saying your observation, you say your interpretation of the observation, and you attack that person as a person. There you have to be careful. You have to think about being kind: how does what you say affect that person? And this is not wishy-washy, tree-hugging hippie stuff. I think it's important to be kind, in that you pause and reflect before you say something. Even when you're being open and transparent, you need to pause and think: how will that affect that person? Of course you don't want to hurt people just for the sake of hurting them, but it also requires you to think: what am I saying? Do I stand behind that? Is it an objective observation, or is it my interpretation, or am I just being an asshole? That requires you to really think about it, and that allows you to go to the core of the problem. Just saying random shit like: you're to blame. Okay, what does it solve? Great, you've vented, you're lighter. The other person is pissed off, but most of all, you haven't touched the essence or the core of the problem. So that's why: be open, communicate, think about what you say. At the company, everybody was saying what they were thinking. You could just say it. But then be kind, and do it in a way that you talk to me about the topic and the object, and don't attack somebody as a person.

Shamil Malachiyev: Did you have a difference between being kind and being nice? I think a lot of founders struggle with this: they try to be seen as good by everybody in the company. They want everybody to like them. And instead of being kind, they sometimes start being nice to everybody, when in reality the kind decision would be to tell the person the hard truth, rather than just being nice and smiling.

Bart Vandekerckhove: I don't give a fuck. No. Sometimes I am careful in what I say, but I will say it nevertheless. And with some people I know I have to repeat it a couple of times, and I have to shape it in such a way that they're not pissed off. Look, if you say stuff that pisses people off, they're not going to listen. So sometimes you have to say it a couple of times, you have to say it nicely, gently, but you've got to repeat it. It can still be honest.

For me, I don't care about being nice. I don't care about people liking me. What I care about is: am I being a kind person? That's what I care about. And sometimes the truth is the nicest thing to say. I wasn't trying to be nice: I had to let go of people. I had to let go of several people because there was not a fit. And you've got to bring that conversation. And before that, you have to bring it up a couple of times, to see whether you can find a solution: can we find a way that there is a fit, that you bring value? But for that you need to be honest.

Shamil Malachiyev: Love it. We'll just put it on the wall: be brutally honest. It doesn't come easy to all people, and something has to happen in life to teach that lesson, for people to change and be more focused on reality. Did you have any experiences that helped you find out that this is the correct way to run a business, to build a company? What were those moments?

Bart Vandekerckhove: Yeah. A good company like Collibra, a good company that has motion, irons out the kinks in your personality. A good company makes sure that their employees can use their strengths to excel, and makes sure that their weaknesses are ironed out through process and structure. As an employee, before starting Raito, I was completely oblivious to my weaknesses. I thought I was this brilliant hotshot. When I was pissed off, I would directly attack you. Because I thought that's what you do when there's a problem: you go straight on. Of course I was not productive, but the organization just ironed out the inefficiencies of my character. As such, I was never directly exposed to my flaws. I really thought that being directly, head-on, aggressive was productive. No, it was the organization that was productively working around me.

So when I started Raito, I thought: okay, this is the way to go. I went in, I headbutted. I remember one meeting where I just threw chairs. After the meeting, when people left, I was so pissed off because I didn't get what I wanted, so I threw chairs.

Shamil Malachiyev: During the meeting?

Bart Vandekerckhove: After the meeting, when people had left. And it's not productive. It's just not productive. The great thing about a startup is you are immediately confronted with who you are. Your strengths, your weaknesses, you see them immediately. The feedback is immediate: if you fuck something up, it blows up in your face the same day, and if not the same day, then within the week. So you really get to know yourself, and you really have to think about yourself: how are you in the world, how do you work with other people, how do other people operate? You greatly improve your self-awareness and also your people skills. That's something I really developed at Raito.

Shamil Malachiyev: Before joining Raito, you worked at a couple of very structured organizations, like BNP Paribas and Deloitte. Can you talk about how that experience shaped the way you see the structure of a company? Did it help you become a better founder, where you have to merge all of the different positions and make all of these different decisions? Because we see founders who jump into a startup as their first career, and they have no experience working with larger companies' structures, motivational structures, operations. What were the benefits of having gone through all of those structured places?

Bart Vandekerckhove: I think it's just relative experience. I wouldn't say that working at a corporate is going to get you ready for a startup. No way. What it does help you do is understand how your buyer works and how they operate. You lose some of the naivete. Your buyers are typically not startups. They go through a buying process, they're slower, they work with political games. Your buyer has political capital. So having that experience, and being somewhat older, helps you understand better the world that you're trying to sell to. As in helping you be a startup employee? Not really. Though I must say that the experience at Deloitte, I worked four years at Deloitte, was very good. Because there you just learn to shut up and do the work. But that's something you also learn at a startup.

Shamil Malachiyev: Can you talk a bit about political capital? Very few people I speak to actually understand that within their buyers there are politics being played. At large companies it's a different scale: when you have thousands of people working for you, there is a lot of politics going on within. Can you speak about that? It's going to be helpful for a lot of viewers and listeners when they approach their business development game.

Bart Vandekerckhove: I myself am very bad at politics, so I always lose in the political game. But in organizations, you have to step away from the idea that the most productive person is the person that goes up in the organization. That's not the case. Even if you bring the most value, or you're the smartest, the most productive employee, it doesn't mean you move up. The person that moves up is the person that is very good at playing politics, even if those politics go against the values of the organization.

Shamil Malachiyev: What is involved in playing politics at those company levels?

Bart Vandekerckhove: Like I said, I'm very bad at politics, so it's very hard for me to understand what they're doing, but it largely means positioning yourself very well: making sure that you really are perceived by the persons above you as a very valuable player, without being threatening to them. That's a balance political players know how to play. They have a strong network of allies in the organization. And I also think they don't always openly speak their minds. I talked about my values at the startup; the political player in a large organization is in almost every way the opposite of the values of a startup. So if you are an employee in a startup and you try to understand how your buyer thinks, a successful buyer, it's almost the opposite of you. I'm being borderline cynical and negative here, but use this rule of thumb: if you engage with a buyer and it's nice and you really connect, they are not always the people that are going to bring you in.

Some sales cycles can take six months to a year. That's a very long sales cycle. It's your champion that has to bring that solution in. While they're playing Game of Thrones in their organization, people are getting stabbed in the back. They have to bring you in. So you are part of a political play. And that requires political capital, because if they bring you in and the project is a complete dud, it costs them political capital. They're going to lose in the game of chairs, the Game of Thrones. That is the concept you have to take into account: how much risk does it cost for your champion to bring you in? One. And two, most importantly: does that person have the sway in the organization, do they have the political capital to bring you in in the first place? And that's not always going to be the person that you vibe with or connect with most. Although with some of our first customers, we did find them. We found some people that had the capital to bring us in, they had the capital to drive the change, and they weren't assholes. If you can find these, awesome. They are great to work with. These visionaries that have the political sway, that can bring you in, that can drive change. But they are rare. They are very, very, very rare. If you find these: awesome. You're good to go.

Shamil Malachiyev: I would just suggest people look at people within the companies who are just starting their journey on something new, who need a lot of support from outside companies and potential partners, versus somebody who's already been embedded for a few years within the company.

Bart Vandekerckhove: The person that drives the change, that will successfully bring you in: I think it's a person that either has been there for a while, knows how everything works, who to talk to, how to bring you in, so they have some awareness of the company. Or it has to be some kind of rising star that comes in, that is really hired to bring in change, has budget, has basically free play to drive change. If you can attach to that person: great. But you have to test it. And how do you test it? We had long sales cycles, six to 12 months. Data security, a lot of change, big impact, deep in infrastructure, so a long sales cycle. How do you test it? You're a founder, you have your call with your buyer, your champion, you're vibing, there's this great connection. Second call: it's still the same guy. Third call: still the same guy. So this is going nowhere. This is a person with too much time on their hands, and we've talked to plenty of them. Bored. They're going to waste your time. So you need to qualify as soon as possible. You can ask questions: Is there a project? Is there a budget? Who is in charge of that? If they know that, great, they know what's happening. But more importantly: can they bring people around the table? Can they bring the CISO? Can they bring, in my case, a data architect, a head of data platform, a head of data governance? Can they bring people to your call? If not: cut it.

Shamil Malachiyev: Yeah. I know that seeing somebody from legal show up on one of those calls is not usually a very good sign either, because compliance kills a lot of deals at that scale. And do you remember, for Raito, when you were getting some of the first clients and you thought: this is going to work, we're actually moving? Do you remember the first moments where, after a lot of struggle trying to get through those cycles, you thought: I think this has a good chance of working now?

Bart Vandekerckhove: When you start and you close your first deals, that's like a drug. Convincing somebody to pay you money for your product, that's a drug. So yeah, definitely celebrate that. I remember one time we had an inbound lead that found us, and we closed him in a couple of months. For me that meant we not only had a product, but we also had a good website that drove people to find us; they went through the sales cycle and we closed them in a couple of months. I remember that. That is a rush that you're going to keep chasing for the rest of your life, I think. It's an amazing feeling.

Shamil Malachiyev: Can you tell us about your experience raising money as a startup? Is there anything to know about when to raise? What kind of things do you need to have in place to do a good raise and not waste your time?

Bart Vandekerckhove: I only did it once, so I can only talk from my experience. But we raised at the peak. This was end of 2021, the peak of a lot of money being in the markets. I don't think we would raise now. Why? It was just two guys and a vague idea, basically, at the time. We had a good background, we had our pedigree, but that was definitely a challenge. At the time it was easier to raise than now. If I would do it now again, I would have more proof, proof that it works. Why is that? Gathering that proof that it works is also important for yourself. It's navigation. When we raised, we had some sense, and eventually it worked. But as soon as we raised, we had to start hiring. And then you've got to keep these people busy, these engineers. So there need to be requirements. It becomes very practical. The room to navigate and completely pivot was greatly reduced.

Raising capital, opposite to what people say, is really to accelerate, and you need to have a clear trajectory to accelerate on. Of course you can still learn along the way. But if you were like us, still figuring out what the basic idea of the solution is, who the buyer is, what the exact problem is, what political problem in the organization you're solving, that's hard. When we raised some money, we already had to do a small pivot in terms of product priorities. We completely changed the priorities, threw it upside down. But you can't do many of these big pivots after you're raising, unless it was clear at the time you raised that you were going to do such a pivot. So that's what I'm saying: when you're raising, know, or try to know, as much as possible what you're going to spend the money on and which direction you're taking. Or, now, I would just say: thank you for the money, come back in a couple of months' time.

Shamil Malachiyev: Growing as a person, as a founder, as a leader is very hard to do on your own. Some of us need, let's call them mentors: somebody we look up to, somebody who gives us advice, somebody who cuts through the bullshit with us and tells us straight: dude, check this out about yourself, try to fix this. Who were the people that made you believe in yourself, that drove that self-confidence, and who told you straight to your face what you needed to do to get better? What role have they played in shaping your path?

Bart Vandekerckhove: Great question. I really believe in the importance of mentors. I really, really believe in it. One of my mentors, I would say our mentor for Raito in general, was Stan Christiaens. He was one of the co-founders of Collibra. He lives here in Brussels, and he's trying to really build out the entrepreneurship here. He's on a mission to help entrepreneurs.

Shamil Malachiyev: I think Stan is coming to the podcast in a couple of weeks too. We'll probably hear his story too.

Bart Vandekerckhove: So definitely Stan, and I was lucky enough to really get his mentorship. One of the things he always said is: you need a good corporate structure, you need a good board of directors. And it's exactly that. You'll have people telling you how it is. You have people that will help you in terms of founder conflict. You have people that help you with experience. I didn't yet have that board of directors with that structure, but I did add a couple of mentors. Stan was there giving me a lot of advice, listening. That was very, very important. Super grateful for that.

Then one of my mentors, also a coach, was Benny. Benny was the guy that brought Collibra from zero to 100 million ARR. He was the head of sales that brought them there. So Benny was a mentor helping me figure out how to sell this. But he went a bit higher: he was mentoring me as a startup CEO. It was not just about sales, it was the broader picture, and I could talk to him. Sometimes we had sessions where he just listened, didn't say a thing. Next session, he came back and gave me feedback. Even just the talking helped, but then he listened and gave very targeted feedback. At the time it was primarily about working with my investors, my VCs, focusing on the sales cycle: who is the buyer, what problems are they having, and what product do you need to build to help them out. With Benny the pointers were mainly on how you sell this, today and in the future: who's your buyer, and then what product are you going to build. And don't forget the product. It's all about the product. Though he was initially just helping me out with sales, he really brought that broader picture: don't forget product. Product is the main driver for your sales.

And then I had a third, very unlikely mentor, and that was my lawyer. I had my lawyer here in Brussels, Luc. He was officially my lawyer. But in very, very difficult times, where I would really call Luc on the weekends for legal advice, he would not only give me legal advice, he would also give me counseling. He's a well-established lawyer with a big office that mainly works with startups and scale-ups, so he really knows the journey of a startup founder, of somebody working on a scale-up. He has a broad network, a lot of experience and insights. So he would give me advice beyond just the legal. And that was extremely, extremely helpful in very difficult times, where I could fall back on Luc and he would give me sane advice. Not just what's legal, but what to do as a CEO and how to best move forward. So with these three mentors: I would say they were extremely important in the success of Raito, and just in my mental wellbeing.

Shamil Malachiyev: A lot of people I talk to, I tell them it's important to have mentors around you, because people are willing to give, to share, to help. The world is not cruel. We're all humans, we've all been through different stages, we want to help others grow too. But most people ask me: where do you find them? How do I identify who I need as a mentor, and the direction in which to look? What would you tell those people?

Bart Vandekerckhove: I think I was fortunate. Everything happened through my network. All the connections were made through the network, and it helps: if it comes through your network, you can trust it more. Just a simple example: my lawyer was recommended through Stan, because he used to work with Luc. That's pure network. If I had had to find my lawyer on Google, it wouldn't have been the same story.

Shamil Malachiyev: After four years building Raito, you do a sale back to Collibra. Can you tell me how that happened? Did you build Raito from the start thinking: what is our exit strategy, what do we need to build and integrate with the current capabilities at Collibra to be attractive and easy for them to absorb in the future? Or did it just happen naturally?

Bart Vandekerckhove: I was really thinking of making a big company. I was really striving for the future. I was thinking about managing privacy and security for in-body devices; that was how far in the future I was thinking. I was already going sci-fi with the long-term vision. But of course, the initial idea was shaped at the time I was at Collibra, so the experiences at Collibra shaped my thinking. I was at a party with Stan where I said: hey Stan, I'm leaving Collibra, I'm going to start my own thing. And Stan said: well, be careful, because your opinions and your views are shaped by what you've seen at Collibra. It largely determines what you're seeing, and it's also the product you're building, and it's also the market you can tap into. And data governance is not as big a market as, I would say, other products. So he kind of warned me: watch out, the way you look at the world is very much shaped by what you experienced at Collibra. And although I had my long-term vision, I'm now back at Collibra, so Stan was right in a way.

But I was not building a product to get acquired. I was building a product to really build my own company, something I really wanted, and I guess still want, to do. But while I was building it, that was plan A. And I always worked on my plan B. Plan A was: aim for the stars, go for it. Plan B was: if you don't get there, make sure you land on the moon. And that was an acquisition. So throughout the time period, I kept in touch with Collibra, with the product managers. I also kept in touch with some of our direct competitors. We were friends with our competitors. Throughout the time, we even had discussions with competitors around acquiring us. Just keep working on those options. It doesn't mean you have to go for it, but keep them alive, in case plan A doesn't work and you can fall back on plan B. And then gradually we saw that the need for what we built with Raito was reaching a point at Collibra where it was so important as a priority that the acquisition almost came directly, immediately, from that.

Shamil Malachiyev: You talk a lot about networks. Networks of people, how you are lucky to have people in your network. How do you build those networks, in terms of building relationships, investing in relationships, picking the right relationships to invest in, making sure each part of your network gets at least a once-a-year "how are you" update? How do you approach building networks?

Bart Vandekerckhove: You've got to tell me, Shamil. I'm very bad at networking. Very, very bad at networking. Like I said earlier, as a kid I was living in my head, and that's where I like to be. I love talking to myself. These are the best conversations. I always agree. I'm very much an introvert, so networking for me is something I haven't figured out quite yet.

Shamil Malachiyev: We're doing quite well here on the podcast, by the way. Great job.

Bart Vandekerckhove: Yeah. So I just hang out with people I like, that I admire, that are interesting. And if something comes out of it, who cares. The people I stay in touch with are the people that mean something to me, that I like. I honestly don't expect to get something from it. And if I can help them out, even better. That's how I approach it. I don't see it as something transactional. Maybe I should. But people I find interesting, I like. If I can help you out, even better. Awesome. That's how I approach it, and we'll see if it's the right way. I don't know.

Shamil Malachiyev: Some of my friends basically have this vision: if I cannot help you succeed more, in terms of business value, then I'm not a good friend to you. They focus friendships and relationships a lot around adding monetary, financial, business value to each other. While for others, friends and work are completely separate: friends are where you go and chill, you have a steak, and you don't talk about work. As a person who's deep in the industry and does a lot of high-level work, how do you juggle keeping your personal and work relationships together?

Bart Vandekerckhove: I think there's a spillover. There's a spillover, one hundred percent. If you're serious about entrepreneurship, there's always going to be, with a lot of your friends, a business side around it. But you also need to be able to separate it. It can't be that with your friends it's always about business. That would be boring, I guess. But there's always going to be a spillover.

A word of advice that my mother gave when I started Raito. She said: you've got to give your wife a percentage of the company. Because if you want her to support you, to help you out with the family while you're doing this business, there needs to be some kind of monetary incentive as well for her.

Shamil Malachiyev: Interesting. So did you?

Bart Vandekerckhove: I did not. And I will do it next time. Because there were periods where I was so stressed, I was so unpleasant to be around at home. Your wife has to counterbalance that. You've got kids that are highly in tune with your emotions: when you're stressed, they're stressed, and then everything just breaks down in the house. So in that sense, the next venture I do, I'll give my wife a percentage of the venture, just because she deserves it. And I would never separate them. You need to find this healthy balance between what you're doing business-wise and what you're doing in your personal life. There needs to be a nice balance in between, and that means there will be spillovers.

Shamil Malachiyev: You've mentioned there are moments where there is a lot of stress. Most of the time it's a situation where there's a shit-ton of stress. Do you operate well under stress, or do you have some methods to reduce the cortisol level, to function better without having too much anxiety in your system? What works best for you?

Bart Vandekerckhove: Like go club seals, or drown kittens.

Shamil Malachiyev: Well, maybe not to that extent.

Bart Vandekerckhove: I like to operate in the unknown. I'm perfectly comfortable not knowing. Fuck it, you never know. All you can do is just try and make sure you live another day. And that means living the other day: if you exhaust yourself from rushing and stressing, you're not there the next day. Like I said earlier, you have to make sure that time is an ally, and I always work towards that. You're in uncertainty, you don't have all the answers. Just go, use the information you have, take a jump, move forward, learn and adjust. That's it. That's how I dealt with stress. I'm perfectly happy not knowing. I'm perfectly happy making mistakes and then just adjusting afterwards. It's just a learning process.

If you look at how they describe fundraising: each time you get money, the money is really just to learn. You've proven initial market fit, there are buyers for your product, you raise capital. Why that capital? To learn if you can build out a repeatable sales process. And then you go to a Series B, you raise capital again. Why? Can I build out that repeatable sales process in other regions, other markets? So that's what it's all about. It's really about making time your ally, and accepting that you are a person with flaws that makes mistakes, and most of all, accepting that the people around you also make mistakes, but everybody is there making decisions with their best judgment and with their heart in the game. This is also how I operated at Raito. I gave high degrees of independence to the people I worked with. I really put a lot of confidence in the decisions they made. But then we would regularly re-evaluate those decisions, and we would adjust where needed. That's it.

Shamil Malachiyev: With the high-performance friends of mine who operate well in uncertainty, I've noticed two things that generally connect them. One: some have nothing to lose. Literally, they're at the bottom level, and if everything fails, they don't lose anything, so they're just out there and uncertainty doesn't matter. And there's a second version, who are more spiritual, not religious but spiritual, and they believe they're unbeatable: I know things will work out. I have no clue what's out there, but I know I'm going to go, and things are going to go my way. Do you have either the first or the second? What are those secret ways in which you view the world and the universe that help you stay confident in those environments?

Bart Vandekerckhove: Good question, man. Definitely not the first one. I had a house, a mortgage, a wife and two kids. Young kids, that grow, that you need to feed, and you need to buy a lot of clothes. So I had a lot to lose. But indeed, I would guess more the spiritual way. I knew it was going to end well. I just knew it. I really believe in this. It's something I said at an offsite a while back. You know this phenomenon with motorcycles? Have you seen these videos where there's a motorcycle rider, they're driving in the mountains, and they drive off a cliff? That is because they're so focused on the cliff that they don't want to drive over, they're so focused on it, they're looking at it, and then you drive in that direction. That's what I believe in. You go where you're looking. If you're always looking at what's gonna go bad, that's where you're gonna end up.

And I also believe that the outcomes in front of you, one year, two years, three years, four years out, are never binary. It's not one or the other. It's a distribution of outcomes. And you're going to end up somewhere in the middle of that distribution, the most likely outcome. But that most likely outcome is going to depend very much on where you look. In the distribution of possible outcomes, if you constantly focus on the bad outcomes, that's the outcome you're going to get. Whereas if you focus on the good outcomes, it might not be exactly the outcome you want, but you're going to implement all the steps necessary to get there. And implementing those steps takes time, takes energy, takes somebody who's level-headed. You just have to do it every day. Just put in the work, be cool.

Shamil Malachiyev: What is your process? Thinking about bad stuff is easy: our minds are in survival mode from the old days. We think about how we survive, what could go wrong, how we make sure we're okay. Do you have some sort of practices within yourself, like if you're worrying too much, you do this, or every morning you wake up and do that? Practices to put yourself in that positive state, to visualize the goal and keep it in perspective without getting distracted?

Bart Vandekerckhove: The answer is: I don't know. But maybe I don't know because I already implemented the frameworks to get there. Having a family keeps you grounded. I had to be home to cook and feed my kids, so you have to stop thinking about work for a moment. That's one thing: it keeps you grounded, it keeps you from spending too much time on work, it helps you reframe things. Another thing is eating healthy. I would almost cut back drinking to nothing; I didn't consume alcohol, or very, very little. I would eat healthy, and then I would exercise. Every day I was in the office, and it's a bicycle ride, so every day I was outside cycling, and at night I would come back. I think because of a lot of these building blocks in my life that force me to be healthy, to be disciplined, to think of other things, it immediately helped me have a good sense of the risk, of the uncertainties, and not be too bothered about the downsides.

Now, also bear in mind, there are weaknesses I have. I tend to be a bit sloppy with details. I tend to be over-optimistic. And that's where my co-founder helped. He would see where things could go wrong, because again, he needs to build that stuff. So that's where we had a good, healthy balance. If you would have combined two of me, with our visions and our optimism, nothing would have been built and we would have gotten nowhere. So it's also the combination with your co-founder that helps you.

Shamil Malachiyev: And here is the last question I want to ask you. In the world right now, with AI, with everything, we've seen a lot of people either losing their jobs after 10, 20 years in the industry, but they have all this great experience, they know how these companies function. And a lot of them are thinking: maybe I should join a startup, maybe I should start a company. What three pieces of advice would you give them, if they want to take the path of actually starting a company of their own, after having a lot of experience in a large company?

Bart Vandekerckhove: So the person you're describing is a person with 20 years of experience in the industry that lost their job, basically for whatever excuse, because companies laying off for AI is a lame-ass excuse. I've never been laid off, but I would think getting laid off emotionally scars you. So first of all: process it. Don't take it too much to heart. Don't beat yourself down over it. I think getting laid off is in no way a statement of your value. That's one. Pick yourself up, gather your bearings.

And then two: I'm sure there's an idea. If you've worked 20 years in the business, you know all the opportunities. There are so many opportunities, there are so many processes that don't work, where you can just come in with a simple solution. So think about your experiences, see where you see the opportunity in the market, I'm sure there are, and start selling it. I would not say start building it. I would say start selling it. And that is probably, for a lot of people, the hardest part: go start and sell it. Go out there, make yourself a fool, write that post that is ridiculous, get rejected, but meet people, talk to them, learn, improve. But of course, it all depends also on your financial situation. It's hard to give generic feedback, but if you have a good financial situation and you don't have to worry about money, then I would say: nice, fuck yeah, let's go. Awesome opportunity, man. Or woman.

Shamil Malachiyev: And what are you personally most excited about for the next five years?

Bart Vandekerckhove: I have mixed feelings. I think we're at the dawn of a rupture in the social contracts and the economic and political agreements. A lot of people have been fucked over that are angry now, rightly so. I think we're going to go through seismic changes in social life and political life and so forth, as you see around. A lot of people are dying, more will die, unfortunately. But I think it's also a time of immense opportunity. If you're fortunate enough that you have enough money to feed you and your family, and you have a roof over your head, I think there's so much opportunity ahead. Like I said earlier, outcomes are a distribution, and the distribution is very wide. There are a lot of potential outcomes, both bad and good. So what I'm doing is hedging my bets. I'm taking measures in my life where, if the worst happens, my family and myself remain in relative safety, but then also looking for ways to enjoy and benefit from the uncertainty, the variance that's coming.

And you mentioned AI. AI is really going to change the world in the coming 10 years. And you want to know why, or how? You don't. But you want proof that it will change the world? Look at the dot-com crisis we had, where the internet had a shit-ton of funding and was extremely overvalued. We hear the same voices about AI now. Surely it's overvalued, but we're not even at the same size as the dot-com bubble. It's going to burst, a correction is going to happen. But look at where we are now. We have cloud-native, data-driven companies that don't have brick-and-mortar stores. This was unthinkable in the 90s. In 10 years' time, we're going to have companies that are AI-first. I don't know how to imagine what that looks like. So I would say: try to position yourself in a way where you can find a place in that brave new world.

Shamil Malachiyev: Thank you. And on this note, I can say that was a fantastic session. I think a lot of people will find a lot of value in your optimism, your confidence, being able to interact with other people out there, look for mentors, challenge your weaknesses, be honest. Thank you so much for coming to the show. And I guess from all of the listeners too: thank you for showing up authentically and letting us see the real Bart out here.

Bart Vandekerckhove: Thanks, Shamil. It was great being here, so thanks for having me.