An Interview with Volodymyr Demianenko
What makes a startup investable, not just in theory, but in practice?
How do top investors decide who gets their money, time, and trust?
Few people can answer those questions as clearly — and honestly — as Alex Vitchenko. With over 20 years in tech, around 40 startup investments, and multiple successful exits, Vitchenko brings the rare combination of entrepreneurial grit and investor insight. As the founder of Digital Future, a Ukraine-born VC fund backing early-stage, globally oriented startups, and CEO of the fast-growing mental health platform Calmerry, he’s seen every side of the startup journey.
In this insightful conversation with Volodymyr Demianenko, Alex shares:
- How investors evaluate startups (beyond the hype)
- The founder traits that turn him off — and the ones that seal the deal
- Why smart money is more about staying out of the way than micromanaging
- And the realities of building scalable companies in today’s ecosystem.
Let’s start with your backstory — briefly. Where did your project come from, what were you doing before, and why did you decide to get into investing? In other words, how did it all begin?
Well, I’ve been an entrepreneur before, and I still am — running several businesses, mostly focused on Western markets. Back in 2014, investing was part of my diversification strategy. At that time, we were launching several new directions, and one of them was venture investment.
It was an interesting moment — the war had just started, not a full-scale one yet, but the first phase. A lot of players fled the market. We went against the tide and ended up building a really strong portfolio. Many incubators and accelerators shut down, and Western investors pulled out.
So, we stepped in. And one thing led to another — it drew us in. I’d say our investment activity came in waves, but overall, we remained stable. At that time, very few Ukrainian funds were able to operate successfully.
Since I had a lot of experience in Western markets, I had real expertise to offer. At the beginning, we were quite hands-on with the start-ups. Later, we stepped back a bit — it came in phases. But we always tried to offer what’s known as 'smart money.'
My philosophy is that the main thing is not to get in the way. Offer guidance when needed, but let them drive. Some founders listened to our advice, others didn’t — that’s their choice.
But we managed to pull off our first exit pretty quickly — within about a year. That one was a project called Jeapie Inc.
So, in one of those years — if I’m not mistaken — we made 13 investments and became the most active Ukrainian investor.
What was the typical investment size?
Anywhere from $50K to $ 1 M. But we figured out that we’re most comfortable at early stages investing $100K, $200K, $300K, or $ 400 K. Even at slightly later stages, we still prefer to stay in that $100–$400K range. Things have changed over time, of course, but that range is still roughly where we operate.
At the beginning, we were heavily focused on my own area of expertise — Western marketing. That’s why we had a lot of martech startups in our portfolio. I found that space exciting — great businesses, really. But over time, things evolved. Now, I don’t enjoy tech or health tech as much as I used to.
It’s great when a project is growing, but I’m most interested in how to exit from it. That’s the more intriguing part for me.
So now, you primarily look at projects that you believe have a strong chance of being acquired?
Not necessarily. For me, an exit can simply mean the company survives and grows to a Series A round.
So, just reaching that milestone is enough?
Yes, by that stage, the company is already in a relatively liquid position. Acquisitions are often being offered. But M&A is incredibly hard to predict — everyone builds their own hypotheses, but it’s often impossible to see what's really happening under the hood of an enterprise or what they’re struggling with internally.
What happens a lot is that an investor comes in at a $15M valuation, but the startup sells at $ 10 M. That’s a frequent situation, unfortunately. Best-case scenario, the investor just breaks even, depending on their entry point.
From the founder’s point of view — especially if they didn’t invest their own money — they still get real cash. Sure, it might be less than they hoped for, but it’s cash. The final amount depends on a lot of things: how much equity they hold, how many investors there are, what the cap table looks like, and so on.
In general, founders usually get something out of it. But when founders put in a lot of their own money, it’s psychologically harder to sell. They think: “I can’t sell this startup for less than I put into it.” That emotional barrier is real.
And even though the money is technically just capital, they’ve also put their heart and soul into the company.
They’ve been grinding 18 hours a day — and while few people calculate that as an investment, some do. If they also put in a lot of their capital, then exits become even harder emotionally.
And the reality is, many startups do get acquired — but often at low valuations. That’s the unfortunate part investors have to deal with.
Let me clarify something, earlier, you mentioned that your goal is to find projects that can make it to a Series A round?
Yes, for example. Or projects that have a truly unique technology. Even better, if there’s a real roadmap toward an IPO, though that’s rare. If you don’t have IPO ambitions, serious money won’t come your way.
People just assume they’ll inflate the numbers somehow and get a good liquidation event. Then you hear, “Okay, let’s give them $100 million” — like Tiger Global used to do. Remember how many such deals they made? They weren’t even a classic VC — more like a late-stage player that rushed into the market. I’m not sure how all that ended for them, but it doesn’t seem like it ended too well. They invested a ton of money during the boom, and then just went quiet.
Speaking of Digital Future, we were actively investing from 2018 until we decided to take a pause. Why? Our portfolio had grown too big. It’s one thing if you have just one investment, but when you have many companies, it becomes a lot. I’m still an entrepreneur, and like many, I launch something and expect results tomorrow. But it doesn’t work that way in VC. A very good question is: how long are you willing to wait?
The stats say that for emerging markets, the average VC holding period is 13 years. Not every investor has patience for that.
What are some characteristics you look for in a founder? What would you say are positives, and what are red flags?
Well, one clear negative is when there are unresolved conflicts, especially between co-founders. We’ve seen this in some of our portfolio companies. Sometimes we found out indirectly, through third parties, and we had to try and step in to mediate. It’s a serious issue and a deal-breaker for us if it isn’t addressed.
What about expertise — say someone has little experience?
That’s rare, but yes, we’ve seen it. Life happens. But beyond experience, location, and basic capabilities also matter — for example, if you're targeting international markets but don’t speak English, that raises questions. It's ambitious, sure, but how will you actually execute?
Does age or background matter — say a 20-year-old student versus a 40-year-old corporate employee?
I currently lean more toward experienced people — they tend to be more stable. But they often lack the burning energy that 20-year-olds have. That said, sometimes young people surprise you. If someone learns quickly and performs well, they can be the right pick, even if they lack a formal track record. You just have to be open-minded and look at their potential.
Once someone is on your radar, how long does it typically take before you invest?
It really varies — sometimes it's fast, sometimes it takes a long time. But ideally, we like to observe for at least a few months before making a decision.
And what types of founders dominate your portfolio?
Sometimes they come through recommendations — like when another investor says, “This founder is amazing,” or they win some competition and people say, “This founder knows everything.”
But here’s the thing — being a “great founder” can mean different things. Some people are just really good at selling themselves — at speaking well. But performing is a different story.
I prefer the quiet types — the ones who don’t talk too much but get things done. That’s more valuable to me. Of course, it depends on the business type. In B2B, for example, founders don’t always need to be public-facing — they just need to understand their product and how it works.
Some of the most interesting founders are technical—introverted engineers or programmers who sit quietly but build amazing things.
And in terms of product types, what dominates your portfolio?
Historically, we've ended up with a lot of B2B SaaS and marketplaces. There’s not much B2C in our portfolio. Personally, I like B2C from a consumer point of view, but not so much from an investment perspective — it’s tough. User acquisition costs are high, competition is brutal, and monetization can be tricky.
Investors often don’t value revenue that much — instead, they look at the technology, the strategic fit, and whether the business complements an acquirer’s goals. Sometimes companies are acquired just for the team, and that’s a valid reason too.
For a while, I used to think recurring revenue (rev/multiplier) was the most important thing. But it turns out it’s not always that critical, at least not at earlier stages. It only becomes a major factor at very late stages, like Series B or C. But you have to survive to reach that point first.
A couple of questions — first, do you often act as the lead investor in deals? And second, how many startups have you invested in so far? What’s the total number in your portfolio?
Let me check for an exact number, but roughly around 40. Somewhere between 38 and 40 companies. We’ve had 11 exits.
And those exits — did they actually generate real returns?
Yes, some of them brought in solid returns, others less so. It varies from case to case.
What would you say are the most prominent or defining projects for your fund?
Alex Vitchenko: One of the standout ones was Attendify — we invested heavily in it, and it was acquired. It’s a fairly well-known case, and we’ve already exited from it.
But honestly, our biggest returns came from a cybersecurity project that unexpectedly took off. There's another company in our portfolio right now that has grown in valuation by 25 times since we invested. That’s exciting too — we haven’t exited yet, and it might grow even further. That one could be a big win.
Looking back at your 40 investments, are there any patterns? You've mentioned a few successful ones — is there something they all had in common, or was it just luck and timing? Are there specific factors that made the difference?
Yes, there are certainly factors — what, where, how — but honestly, venture capital follows the law of large numbers.
Until you’ve made at least 10 investments, it’s too early to draw conclusions. I know investors who’ve made two bets, and they're thrilled because valuations went up. But they haven’t seen any money back yet. It looks great on paper — but that doesn’t make it a sustainable business model.
As for patterns, sure, it helps to start with what you know. But you shouldn’t limit yourself to just one domain. Just because you sold one startup in a certain field doesn’t mean you should go all-in and fund ten more in the same space. That rarely works out.
You need to look for diverse themes and untapped niches — places where there’s real growth potential. That can come from either:
- Organic growth — you invest money, it pays back with profits, and you reinvest.
- Or inorganic growth, where a large strategic player acquires the startup before it scales fully.
With organic growth, the idea is: you put in money, get a return, reinvest, and repeat. That shows you’ve found product–market fit. It means you can scale in a healthy way — and that’s what you want.
One more question — since your focus is mostly on Ukrainian founders, do you think that limits your perspective? Why don’t you invest more in American or Asian founders?
It comes down to personal philosophy. We have invested in various foreign startups, but honestly, we weren’t fully satisfied. There was no real chemistry — we didn’t feel connected. We ended up acting like passive investors, unable to offer much value. We tried, but something just didn’t click.
So being involved matters?
Not necessarily. But even basic things like checking someone’s reputation or verifying their background become much harder. Of course, the ultimate goal is to earn money. But maybe because of my entrepreneurial background, I don’t want to feel like I’m just putting money in and waiting for it to come back like at a bank. I want to help — without interfering — and be a meaningful part of the process.
When the entire interaction happens in English and at a distance, it doesn’t feel the same. Plus, it’s difficult to gather reliable information. Everyone presents well on the surface, but it’s not always easy to see what’s really going on.
We’ve looked at other markets. They often raise a red flag: if there’s so much local capital, why couldn’t these startups raise money there? Why are they coming to us? And often the answers don’t inspire much confidence. That’s when you start to feel like there’s something off and you need to dig deeper.
Many of our investments come through our network, from other investors who’ve already done some due diligence. They might say, “We haven’t invested yet, but if you do, we’ll join.” So we take the first step, start digging, and see where it goes. It’s often built on informal trust.
And you compare notes on how promising the founder or team looks?
Yes. There’s also this community aspect, especially in angel investing. On one hand, it’s fun. But it’s definitely more about engagement than making serious money. It’s about meeting people, sharing ideas, and feeling like you’re part of something.
I am in angel investors community. We socialize, talk startups, have drinks, and stay in touch. The vibe was always, “Soon something big will happen.” But it’s not really about short-term returns — it’s more about relationships. Once you’ve invested in a startup together, there’s a bond. People start saying, “Let me introduce you to someone,” and those connections lead to real collaboration.
Can you get rich doing this? Maybe not. Some people did make tens of thousands, sure. But they also spent hundreds of hours networking, vetting, and communicating. If you factor in the time, it’s a long game.
Still, it’s incredibly interesting. A lot of angels are entrepreneurs or people just looking for creative energy. You hear a pitch and think, “Wow, I hadn’t thought of that — maybe I should try something similar.” Or you think, “They’re making it way too complicated; this could be done much more simply.” It becomes part of your personal and professional growth.
And then there are the super angels — the ones with 100+ investments. That’s a whole different level.
In the U.S., some angels get really deep into investing. Eventually, for many of them, it becomes a full-time commitment. They might not invest their entire fortune, but a significant part of their capital ends up going into start-ups.
Now, traditionally, the recommendation is to allocate no more than 5–10% of your capital to start-ups, because it's such a high-risk asset class. But despite that, I often meet angel investors who’ve only done one or two deals, and they’re already like, “That’s enough for me.” They’re not that engaged. They might say, “If the startup fails, whatever — I didn’t invest that much anyway.” They’re not watching the project closely or emotionally invested in the outcome.
Not everyone’s doing 100 investments. I think the sweet spot is usually 5 or 10, depending on their financial capacity.
Sometimes, funds launch with a lot of noise, invest for a few years, and then just disappear — either because of issues with their backers, or they simply stop investing. On the other hand, some funds stay active, but despite making a lot of investments, they haven’t seen real returns — sometimes due to external reasons like unfavorable market conditions.
Newer funds tend to act more energetically and take more risks. But experienced funds — well, they’ve been burned before. They’ve seen the downside, so they look at everything through the lens of risk, past lessons, and a bit of healthy skepticism.
So, if someone reads this interview and feels they meet the criteria Ukrainian funds are looking for, should they expect to raise their first round entirely from Ukrainian investors, or do they need to combine that with U.S.-based capital?
That always depends.
Let’s say it’s a pre-seed or seed round...
If there’s real traction or something to show — why not? It’s doable.
Yeah, a round could be closed entirely with Ukrainian capital — some from funds, some from angels. That does happen.
For a founder who wants to work with Ukrainian funds like yours, when should they start building relationships? At what phase in the startup’s journey is it best to begin connecting with a fund like yours?
We generally prefer to work with startups at the Seed stage, because the risk is more manageable. But Pre-Seed is also possible — founders just need to be prepared that we won’t immediately fund something based purely on an idea. Typically, angels invest at the idea stage, and then funds like ours come in later.
We start paying attention when there’s some traction — it draws our interest. For example, if a startup is already generating over $10K a month, that definitely gets us excited. But even $10K or $50K in monthly revenue isn’t always enough — some companies grow to that level and just stall. They don’t get acquired, there’s no exit — and sometimes they can’t scale further.
At that point, things can get shaky. Founders start burning out, team morale drops, and they begin to struggle. That’s when I put on my “coach hat.” I try to talk to the founder, act like a bit of a psychologist, and help them think through what’s next. Some founders are open to that. Others keep it all inside and end up making emotional, and sometimes poor, decisions.
You can find yourself in a situation where the company has value, but you can’t extract that value — you can’t liquidate your position. And even though the business is generating revenue, you can’t pull much money out either.
For me, a red flag is when the founder starts talking about dividends — that’s usually a sign the startup has hit a dead end. If we were talking about a cash-flow business with different expectations and valuation models, maybe. But in venture capital, we don’t approach it like that. We approach it as a startup: scale first, exit later.
Just to clarify — when you say “exit,” do you mean after the next big round is closed?
Not necessarily. For us, it’s when we can sell our stake — that’s what defines an exit.
So it doesn’t have to be in the next round — you might stay in longer?
Exactly. We don’t always sell at the next round — sometimes we stay in. What matters is that we believe the founder can grow the company to a Series A or beyond, attract bigger funds, and create an opportunity for us to exit if needed.
That makes sense. So for you, the key is spotting a founder who, by your instincts or due diligence, can make it to the next level. That way, a larger fund comes in, and you get your opportunity to sell. That’s one option.
Right — or someone might acquire the company. Or, in the best-case scenario, they reach an IPO. That’s the hardest and most rewarding path. Acquisitions happen too, but they’re harder to predict — not something you can base your whole strategy on.
And sometimes, the company shuts down, and all you get back is whatever’s left. In rare cases, there’s a soft-landing — like the startup folds, but the investor is offered equity in the founder’s next project. These scenarios do happen.
So ultimately, your decision-making comes down to a few key scenarios.
Of course, the most exciting case is when everything is working, the startup is growing rapidly, and the metrics look great. But then comes the big question — should we exit?
When everything is going well, it’s tempting to stay. But sometimes you shouldn’t. I have two examples: in one, I exited and the company kept growing and thriving; in the other, I exited and it began to stagnate. I won’t name them, but I made a decent return in both cases.
But that’s why we’ve decided: we’re not in it to sit until the very end. That’s just not our strategy or focus. We don’t have controlling stakes, especially in late-stage rounds, and the rules of the game change completely at that level. There are new legal complexities and power dynamics, and we understand that we’re not equipped for that yet.
Dealing with elite U.S. funds at that stage means playing by their rules — and that takes a lot of experience and leverage.
