
Web3 CMO Stories
🎙️ Smart, strategic conversations at the edge of Web3, AI and marketing.
Hosted by Joeri Billast, this top 5% global podcast dives into how bold brands and founders grow with visibility, trust and storytelling – across tech, community, and culture.
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Web3 CMO Stories
Wisdom from a Young VC's Journey | S5 E29
Money shouldn't be your startup motivation: a profound truth that Violetta Chekan, VC and entrepreneur with over 13 years of early-stage investing experience, shares from the beginning of our conversation. "A startup doesn't have any money until the exit. Exit will happen like in five, ten years," she explains, highlighting why founders need deeper motivation to sustain them through the entrepreneurial journey.
Having started in venture capital at just 19 years old and closing her first deals by 21, Violetta brings a unique dual perspective as both investor and former founder. This combination has shaped her approach to evaluating startups, where she prioritizes team qualities over even the most brilliant ideas. "I try to have much more empathy as well to the founders, because I understand the journey," she reflects, describing the founder-investor relationship as a "marriage" that demands careful selection and mutual trust.
Throughout our conversation, Violetta reveals the green and red flags she watches for when meeting founders. Transparency tops her list of essentials, while she's immediately wary of those who claim numerous business connections but can't produce evidence. For blockchain ventures specifically, she differentiates between artificial hype and genuine traction, especially in B2B solutions where she focuses her investments. "You need to have either pilot contracts with companies, either existing agreements, either letter of intent for commercial adoption," she advises founders looking to prove real-world value.
Perhaps most valuably, Violetta shares how her own podcast journey has transformed from overcoming her fear of public speaking to becoming a powerful learning tool through conversations with experienced entrepreneurs and investors. Her story exemplifies the continuous growth mindset she values in founders—the willingness to listen, adapt, and evolve that sets successful startups apart.
Whether you're a founder seeking investment or an aspiring investor, this episode offers rare insights into startup evaluation from someone who's experienced both triumph and failure from multiple perspectives.
This episode was recorded through a Descript call on June 19, 2025. Read the blog article and show notes here: https://webdrie.net/wisdom-from-a-young-vcs-journey/
I tend to also have a red flag, which is money as motivation. So if you're doing the idea to earn money, this is the wrong place, because a startup doesn't have any money until the exit. Exit will happen like in five, ten years.
Joeri:Hello everyone and welcome to the Web3 CMO Stories podcast. My name is Joeri Bilast and I'm your podcast host, and today I'm really excited to be joined by Violetta. Hey Violetta, how are you?
Violetta:Hi Joeri, Nice to be here on the podcast and thank you for the invitation.
Joeri:Yeah, I'm happy to have you After we met. I think it was at CODA in Porto, where we were both speakers. I think we met at the speaker in Porto, where we were both speakers. I think we met at the speaker dinner. But, guys, if you're wondering who is Violetta, Violetta Chakan she's a VC, Violetta Chekan, and an entrepreneur, but with already, I think, 10 years of experience in early stage investing. You were very young, I think, when you were starting in that field. But for our listeners, Violetta, tell us a bit more and start where you want to start.
Violetta:Well, yeah, thank you so much for a great introduction. Yeah, so I've been very early in venture capital. So I found out about venture capital when I was 19 years old and actually my story is kind of interesting how I got into venture capital. It's not a very typical one, but if we have time I can tell a little bit more on that one. But then at my 20 years, I started working with the first deals and starting closing this Oregia 21.
Violetta:I was closing the first deals so when I was in Belarus so that's where I'm from, so I'm originally from Eastern Europe and then I came to Portugal. I won a scholarship from European Commission. So that's how I never chose Portugal. So that's one of the most common questions One why Portugal? No, I didn't choose Portugal. It just happened that Portugal chose me and I call it my adopted family because I love living here. And then I joined the biggest government funds here.
Violetta:So I've been working with Portugal Ventures and I've been working also with Banco PortuguĂŞs do Fomento, where I was leading VC investments for two funds 200M and Social Innovation Fund VC investments for two funds 200M and Social Innovation Fund. So, yeah, by now I've been a board member and observer at 11 companies closed 15 deals, 20 million across 15 deals and actually a little bit more just don't count some small investments. Yeah, and I'm also a podcaster as well, like you are, yuri, as well, so I have my podcast about Web3, so it's called Web2 plus One with VC. Actually, I just launched the season three, so that's on YouTube, spotify, apple podcast and I'm interviewing the top entrepreneurs and investors in blockchain and crypto space the top entrepreneurs and investors in blockchain and crypto space.
Joeri:Well, yeah, so it's actually interesting and we will put the link in the show notes. It's another angle that we talk about, you know, with people, leaders, from the same space, but from another kind of angle. Now for me, you mentioned in the beginning you can talk about different stuff. It's me all about the stories, entrepreneurial stories, web3, new technologies. Interesting that you have already this experience at your age. You know from as a VC, as a founder, so and then I'm curious you know because you are very young doing that, and then now you have the 10 years of experience. What did you learn in these 10 years? How did this all experience? How does it shape your approach? You know, when you talk to founders, new ventures- Well, thank you for this question.
Violetta:I think, yeah, I have been in startups and early stage investing for over 13 years now, so it's a lot of experience and definitely you have a very different approach from those who just came into this industry.
Violetta:And I also do believe that it's very important for any investor to have entrepreneurial experience, because this is very important, even if it's like a small entrepreneurial experience. But if you just come as like a student, as then entering as an analyst to the firm and then just starting to invest, you don't understand the other side of the story. So how the founders pass through the their challenges, so actually, uh, so yeah, I had my own startup as well, so that's also part of my story. So, 21 years old, so I I thought that, well, I've been already in venture capital and I knew it all. Yeah, so that's as many young people would also think the same. You know, because you are young, you just have this, you know passions and you have already a little bit of experience and I closed already the deals and I saw it already how it's done. So I read a lot. I've been already an entrepreneur myself from, actually from 18 years old, so I've been like individual entrepreneurship, so how it's like called, but I was doing like small jobs, so I had clients for tutoring and I had clients for bookkeeping and like financial services, like accounting, because I was very talented in math. So I started to do that. But, yeah, I had a startup which failed. But I learned so much because what you realize that you take decisions very differently once you are on a different side of the table, and this realization is very important to have because once you are sitting in investor shoes, you see the other person taking their decisions and how they affect the revenue, how they affect the growth, how they affect, well, your return on investment. So that's very different how you, as an investor, take the decisions over the company and I think having these both experiences it complements a lot the company and I think having these both experiences is compliments a lot.
Violetta:And, yeah, I try to to have much more empathy as well to to the founders, because I understand the journey. I try to be very supportive of them, and supportive meaning meaning like giving them straightforward advice. I'm eastern european, I'm ready very straightforward, uh, by myself, as as by nature, by culture and by nature, we, we, we used to to give a straightforward feedback, but the thing is that I think it's very important to to hear this out, and sometimes my feedback cannot be right. Of course I can be wrong as well.
Violetta:As well as we are humans, we, we all, don't know all the paths in. In reality, no one knows what we are doing. But I think it's also important to give the other perspective, because once you are emotionally biased in that baby that you are creating and you are building because that's exactly a baby and I've been in those shoes it's sometimes quite difficult to see outside of that, because you think that, oh, this is this, is this is what we do, but you sometimes kind of like narrowing down because you are like on an execution mode and you cannot see some, some other things. So it's very, very important to to see the uh, the other side as well yes, and then it's.
Joeri:It helps to uh, you know, to feel both of you know that you're not only like the founder, not only like the investor, but because it's different indeed, I also see this if I, you know, help a company with their marketing, or I come in with a fresh view. It's a fresh view that you have that they don't see because they are working in their company so long and actually it's a bit also like an investor. You look at it probably also you mentioned matt with you look at the figures and aren't. Probably there is also kind of gut feeling. I don't know if that plays with you, but if you talk to, you know to a founder, and there are certain signals or that you can see, okay, this is going to work, this is a really good company, or they're doing something wrong, there is a kind of a red flag if you can see, okay, this is going to work, this is a really good company, or they're doing something wrong. There is a kind of a red flag if you can say it like that. Yeah, I'm curious.
Violetta:Yeah, just to add on the previous one thing as well. So one thing that founders also need to have in mind that we investors, we also have the same interests in mind. So we want a company to grow. So that's one of the most important things, and that's what you also, when you talk about the potential and patterns, about the red flags. This is exactly the same, because this is a marriage and you want to grow together with this team, right? So and this is something that very important that I talk about it's values. That is very important to have.
Violetta:So, being very transparent, honest and having trust between each other, because if you are going to have this long-term partnership and this is actually very long-term partnership even marriages nowadays don't last like 10 years, right? So I mean like, yeah, you need to very carefully select whom you are going to be in business with. So if the founders are trying to hide something on the first meetings, this would be like definitely a red flag. So, from the first moment and I always say to founders they listen to me right now so I would love to say be honest, even if you failed in some things. It's like I had my startup. I failed as well. I know how it is and you just learn from it and you iterate quickly because you already learned from that mistake. So you can continue and and iterate and being faster and actually you can also ask for advice, because investors also like to have an advice, to give the advice, and it's also well. I will say how it is, but it's playing on ego as well of the people, because, well, when, when you are in a dating mode right so and you ask for advice, that is very yeah, so no one talks about that, but this is how it is, yeah. The other thing is like more straightforward things, like talking as a business model, obviously like this. This is a red flag. This, this is obvious, I guess, for for most of the listeners, I tend to also have a red flag, which is money as motivation. So, if you're doing the idea to earn money, this is the wrong place, because a startup doesn't have any money until the exit. Exit will happen, like in five, 10 years. So if the person has the motivation, money that would be probably the wrong motivation, because, yeah, at some point it's, the struggle will well, will hit and it will be very difficult to continue. So how, how will you continue. Besides the like, what will motivate you, right, and what will motivate your employees, what will motivate your co-founders? So that is a very good question on that. And, uh, obviously, on the positive signs, yeah, transparency, of course. Yeah, so, being a good listener and actually really listen, that is very good.
Violetta:Green flag adaptability so imagine there is something that they thought they will. It will work. For some reason, it doesn't work right, the market changes, the competition changes, or it was a hypothesis that didn't work, but they adapt quickly. So that is, and pivot quickly. And, by the way, you can come to me with one idea and I will invest and you will change to another idea. This is absolutely right to do, because you need to adapt to the market, you need to adapt to your customers, you need to. So adaptability is one of these important things.
Violetta:And learning, yeah, so, as I mentioned, uh, listening, uh, but not just listening, but also, uh, being able to learn. Sometimes we hear feedback that we don't like, right, so, but able to, to think about this and to learn and to see. Okay, so how is it done? Why, maybe there is something else? Should I try this and learn from this experience? So that's, I think, things that are the most important and, of course, execution. Execution is very different or very broad. I'm sorry, it's very broad term as itself, but I think I gave more or less the description already on the things that I'm looking for. Yeah, and, as you can imagine, I didn't mention idea, oh, that like multi-billion idea, like yeah, I didn't mention that. But team, team is the most important thing.
Joeri:Yeah, I heard it too when I was at the conference and the other investors were speaking not your panel, but another one. And they look at the team, they look at the founder, they look at the network that the founder has, and so on. That was also interesting for me to know. It's not only about the product and also the product. Sometimes they are so technical, those founders. They think they have a beautiful solution, but there is no demand. You said that they need to be able to pivot. Now, you know, in these times with blockchain, with AI you know we met at the Web3 conference Sometimes they are just happy because they have a blockchain solution. I know you are also looking for real world value, of course, because it's not because it's blockchain that it's, so it will be good for business. So how do you actually define if a use case in blockchain, for instance, is real enough to invest in?
Violetta:Yeah, well, as you mentioned real world, so it's yeah, it has to be attached right to the existing workflow and processes which already exist in the real world. So that's for me like the real world, as we say, right solutions in blockchain. So I'm focusing on business to business, because business models, I mean, because I, I do believe in enterprise, adoption of blockchain and I think this is really one that is growing right now. So I, I completely believe in that. So this could be goes to supply chain transability, business agreements, energy, so there is like multiple use cases.
Joeri:And yeah, so that's what I describe as real world. Okay, there's also, you know, these days a lot of hype, and then it's not always easy to you know, distinguish the narrative between noise or really something that can get traction on the market, and I mean maybe especially in B2B or B2B blockchain. I don't know, or do you do that? You know, make a difference between that. You mentioned it already. It should be real life, but are there any tips? You know how we can measure that it is really valuable in real life and not only about hype? Or they want to launch a token and they're only thinking about the token price, which I see a lot too, the short term, the token launch and nothing next. So, yeah, just curious to hear your thoughts, Violetta.
Violetta:Yeah, I think in the case of business to business, it's much more simple, rather than if you go to B2C yeah, b2c is all fun with tokens attached to the token, and also in B2C you also see a lot of numbers that pumped by engagement, farming, like quests, like airdrops, like you know, that is all like artificial, yeah, artificial pumping. But again, if you are like investor, and investor for a while, you can see this very quickly, like this is very easy to see. You know, like it's also the same, like I would just give you like Web2 example. So in Web2 example, you can just like put a lot of money in the marketing, you buy users who buy your product and you have revenue. So that's how you have the traction. And then you show to investor oh, we have this amazing spike, we have this, we are growing so fast.
Violetta:Look at our revenue because you just did this marketing thing. But what if you will stop putting the money into marketing? So that might go down. And that's very important to have organic traction. So that is also like if we transform this to uh, to web3, that is what you're looking for and uh, yeah, it's traceable, it's all traceable. And once you've been an investor for a while you can. You can see these dynamics and you can see these patterns. And for those who try to do this, they think they're smart but in reality it's like 10 minutes to check, so it's like very fast to check, yeah, and for B2B, obviously, it's much easier because you need to have contracts.
Violetta:So you need to have either pilot contracts with companies, either existing agreements, either letter of intent for commercial adoption. If we are talking about like very early stage and this is something that I always advise to B2B companies Even if you just start develop your product, you need to have a rigid traction. And what means traction is exactly letters of intent, because if no one is interested in your solution, how are you going to sell? So you need to know that there is someone that is already ready and interested to buy your product, and that letter of intent leads to pilots, and pilot can be paid, can be not paid, it depends. Sometimes it's just like reversing the costs. This is very typical for like, like a small pilot, and then sometimes you can get the commercial already, like it's an agreement, so you actually put this pilot as as a client. It's not full price, but it's already. It's already a revenue. So that's um, that's very yeah. So it's very easy to ask. You just ask agreements to show due diligence If you see that there is a potential.
Violetta:Often I see that founders claim oh, we talk with this company, we talk with this company. We talk with those, with those, and this is just like you know, like just blah, blah, blah. That's what we call hype or we call yeah. So they are like yeah, we and we close fast. We close now, just like in two weeks we are going to close. There is no time to. We are not like sharing.
Violetta:Like you know, I don't have time like yeah so that's a red flag, that's like immediate red flag. So I agree that good rounds closing very fast, but then you need to, you need to be able to show it very quickly. You need to be able to, as a founder, if you want to close fast, well, you need to be very transparent and you need to have, like one thing is having for, like, creating formal around the closing the round, but the other thing is transparency, and transparency and and honesty with communication. So that's very important as it goes along as well, and yeah and then yeah. So what I mentioned.
Violetta:So first, in growth, you try to see it goes to B2B, B2C in web two, web three. Patterns in growth, spikes, dynamics patterns, so why there is certain spike. So what is like the unit economics, like what you pay, what you have out of this. So how many people actually? What is the retention If we talk about like B2C, right? So how many people are engaging organically, staying organically?
Violetta:What is the life cycle of the of the customer? So the same with b2b. So what is like the life? How much time? How? What is the sales cycle? How much it costs for you to attract this customer, how long this customer will stay, will stay with you, why investors love subscription services?
Violetta:Because this is like. That means that a minimum year you will have this client. So that's a. That is a good, good, good contract, right. So with a with a client, yeah, so that's more like metrics. I'm very I'm very numbers driven person, because numbers don't don't like, and I'm also a math person, so I check always, like these patterns in growth and also the dynamic. And then, of course, you see the team and how the team also reacts to this and sometimes they can say, yeah, we invest in marketing, because, well, now we see this like absolutely amazing growth, because, yes, we do invest in marketing, but we know that from these paid users, this number will stay with us. So this is our retention, so this is how we will grow and this is how we, by volume, we can improve our unit economics and this will be a very good answer. That means they understand what they're doing, why they're doing this and how they will create the good, sustainable revenue.
Joeri:If you compare investors, those numbers are really important that they can explain them. But there is also a part which is less you know numbers, which is the story around everything that they are doing, how they tell their story to the outside world. How important is that for you? The storytelling aspect.
Violetta:Yeah, for me personally not really, but in general, storytelling has a very, very big role. Why? Because CEO has one role and has one skill to do. So this is sales. So it means selling to investor so he can raise money, selling to the employees so he can hire the best team and attract the best team and attract the best team and and retain the best team and he can sell to the customers and get the clients and and well, grow the revenue. So that's is, that's is one skill and storytelling is actually part of the sales.
Violetta:So, um, so, yeah, so that's is very, very important in general, but at the same time, because I'm in this industry for a really while, so a beautiful story perhaps will not work on me, although if it's a story which is how the person started the business, that's what matters for me. So, either, why there is a passion, why is? Uh? So there is a one company that I invested and the story started basically that his mother has has the problem, so he started to look for solutions. He couldn't find a solution and he was frustrated, and then he understood that there is many people that frustrated with the same, with the same problem, so he started to look for solution. That's how he invented the startup that he did. So that story, that matters, because that gives you a perspective of why. Why this team, why this person, why this product. Yeah, that matters.
Joeri:You see, from the background there, the book start with why so, indeed why is important, depending on you know the context, of course. What I'm also curious about is you have your own podcast. How does that so? What is the why for you behind your own podcast and how does that help you, you know, get maybe a front row seat of emerging ideas or something else?
Violetta:well, good question. So I, um, to be honest, my why actually has changed a lot. So I started this as a. So basically, yeah, the podcasting I, I I'm not very good public speaking. I would say I'm always afraid of that. I, I don't consider myself good, although people say, oh, you're natural in this. And when I was like my first interview with Pedro Oliveira from Talent Protocol and he was like, oh, you're so natural in this, like, ah, like it's so good, and I was like freezing inside me, so no, it's not, it's very difficult.
Violetta:And the thing is that it was just like I've been with, uh, very good friends and mentors. I've been, uh, having the conversation and they told me why don't you start a podcast? Why don't you start? Actually, it was not about podcast, it was about youtube. So why don't you start youtube? Uh, and I was like what I will be talking about? And like you have so much of experience and you give advices to the founders and indeed I did mentoring lots of founders and I'm a mentor as well in different accelerators and I give this feedback all the time, as I mentioned since the beginning that I try to give the feedback, so I try to give this outside. So and then it's a job of the founder hearing or not. And again, as I said, like I might be wrong, I might be right, it's, it depends. But it's just a different opinion, a perspective on, on the idea of business and yeah, so that's what, what they said and I, and I said well, well, but then if it's me just appearing there, I mean like, yeah, I did some of the things, but I'm still young, I'm still learning. I consider myself like I'm like, I'm very like, I'm very small, I'm very like I'm learning from this. And then I was thinking that there are people actually that have much more experience in building and I learn from those people. So I it's not like I give feedback to the founders. I learned from my founders all the time and indeed, even how I came to WebTree, that was from my founders.
Violetta:So one of the founders that I invested in Portugal Ventures it was not in blockchain at that time he entered blockchain. He started sending me things and he started to give me like this oh, you need to go to blockchain. So yeah, and uh, yeah, and I listened and I listened and I listened and I was like, oh, yeah, that's, that's the right, the right, the right thing for me to do. So. This was, like, also interesting, and I was thinking, yeah, so these founders have this, they build things, they build and they're building in real time and they can provide this value to the others. Then I have all of these investors as well in my network, who also can give that perspective not only my perspective, because each investor is also investing differently, and founders will need to attract investments from different people, and different people take decisions differently. The way I take my decisions, it doesn't mean that the other investor will take the decision the same way, so that would be fantastic to have maybe someone else on this YouTube channel.
Violetta:That's how the podcast thing was born, and it was literally in one day. The next day, I was already talking with my friend who is a video editor and videographer, and he said, well, I will help you out. And I was like, yeah, let's, let's, let's start this. And now, to be honest, I'm very, I consider myself so lucky because I learned so much from each of these individuals, and it's something that is incredible to do. And you know, yuri, you also learn from people a lot, yeah, and each time, you discover something new, something else, yeah. So now my why is more like I'm learning from them. It's not just for founders right For the others to give that perspective, but I'm also in this process right now. So I am the one who is just learning and I have this whole curiosity to ask these questions. That's why I also told you I always go with the flow with my questions, because I love to talk with people and I love to see where the conversation will flow.
Joeri:Absolutely. For me, it's also you know the why was in the beginning, to have interesting conversations with people, to learn to network. I just love to network, meet new people Can be online, but can also be at a conference, or it can be even on a walk. You introduced me to Oleg from Sweatcoin. Well, we went to Sintra, here where I live, and we went on a walk and it was really on brand for him, of course. So that was a really good introduction and, you know, we met at a conference. I love networking there, but it also works on a podcast. Well, Violetta, the time flies really fast. Now, if people want to check you already mentioned it, but feel free to say it again when can people reach you or where can they find the podcast?
Violetta:Well, you can reach me on Instagram, twitter, linkedin, all the social media. I even have TikTok as well, which I'm not really using much, but I'm also there as well. So, yeah, so you can reach me out on any of the social media and you will have all the links there as well. So what I'm doing and also how do I invest right now. So you can also send me a DM with your pitch deck about WebTree. So my blockchain B2B if you're building in this space pre-seed stage, seed stage Don't hesitate, if you're just starting building, to reach me out as well. So I love to start early and advise the team before I invest. So that's also great, and yeah, so. My podcast is on YouTube, spotify, apple Podcasts as well Amazing, that's also great and yeah so, and my podcast is on YouTube, spotify, apple podcast as well. So amazing.
Joeri:Well, I will put everything in the show notes so that people can find you. Yeah, it was an absolute pleasure to have you on the show, violetta thank you, appreciate this a lot yeah, guys, what an amazing episode.
Joeri:Like I always say with these episode issues for people around you, be sure to share the episode with them. If you're not yet subscribed, this is a good moment to do that so that you don't miss the future episodes. If you haven't given me a review yet on apple podcast or on spotify, feel free to do that, because if you give me these five stars, it gives me an even bigger reach and, of course, I would like to see you back next time. Take care.
Violetta:Thank you.