Vadim Rogovskiy On Building & Exiting Companies And Now Creating An AI Executive Assistant To Extend Human Capabilities

Some entrepreneurs build one company. Others become serial founders. Then there’s Vadim Rogovskiy — a rare breed who has built, scaled, sold, shut down, invested, and started all over again. His journey involved switching industries and switching sides on both sides of the table.

Vadim’s latest venture, Stealth Startup, has developed EVE, an AI assistant that allows humans to focus on high-impact decisions while it handles the rest. AI can filter 80% of noise, 80% of less important threads, conversations, etc., thus extending human capabilities.

In this episode, you will learn:

• Vadim’s journey spans industries and roles — from ad tech founder to AI innovator and from VC to micro-PE investor.
• He built and sold multiple companies, learning early on that building, not just outcomes, brings lasting fulfillment.
• With Clickky, he scaled to $13.5M ARR but learned the hard way that waiting too long to sell can be costly.
• 3DLook showcased his ability to pivot into computer vision, and he stepped aside as CEO when the company needed new leadership.
• Vadim’s stint in VC left him disillusioned, reinforcing that he’s a builder at heart, not just an investor.
• He explored “entrepreneurship through acquisition” through micro-PE to help overlooked startups unlock value.
• His latest venture, EVE, aims to revolutionize executive support with AI — making high-quality assistance accessible and scalable.

 

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About Vadim Rogovskiy:

Entrepreneur and investor Vadim Rogovskiy is currently focused on building his new AI startup, Stealth Startup. The company is developing a transformative product for the productivity/future of work for individuals and enterprises. It has already been backed by some of the most prominent VCs and angels investing in AI.

Vadim is a Co-Founder & formerly served as a Board Member at 3DLOOK. He also served as a Partner at Geek Ventures and as an Advisor at GT-Protocol.

Before launching 3DLOOK, Vadim founded Clickburner, later renamed Clickky, which was partially acquired by a private equity fund, and AdCenter, which VertaMedia acquired.

Vadim is the Co-Founder and  Partner at Wanna Biz. A serial technology entrepreneur, he launched his first company at age 18. Then, he ran a web design studio and a gaming company before focusing on the mobile ad tech industry.

Connect with Vadim Rogovskiy:

• LinkedIn
• Crunchbase
• PitchBook
• NFX

Read the Full Transcription of the Interview:

Alejandro Cremades: Alrighty, hello everyone and welcome to the DealMaker Show. Today, we have a founder who has done it multiple times—been on both sides of the table. We’re going to talk about switching industries, switching roles, you name it: building, scaling, financing, exiting. He had a really nice exit that we’re going to be discussing.

Alejandro Cremades: But again, without further ado, let’s welcome our guest today, Vadim Rogovskiy. Welcome to the show.

Vadim Rogovskiy: Hi, everyone. Happy to be here.

Alejandro Cremades: So, originally born in Ukraine. Give us a walk down memory lane. How was life growing up for you?

Vadim Rogovskiy: Well, I was born in Odessa, Ukraine. It’s a city actually pretty similar to San Francisco—I realized that when I first visited San Francisco a long time ago. It’s a small city on the Black Sea coast, also located on hills with trams going up and down, and very diverse areas.

Vadim Rogovskiy: There were people from lots of different cultures and countries—lots of influence from different places. It’s very cosmopolitan.

Vadim Rogovskiy: So yeah, I think I had a heavy childhood. My father had a career in telecom, and now he’s actually a professor at Polytechnic University. He’s still there, in Ukraine.

Vadim Rogovskiy: My mother is a music teacher—she teaches kids how to play piano. I earned a business management degree from one of the most well-known Ukrainian universities back then.

Alejandro Cremades: Well, in your case, talking about the early years—when you were 18, that’s when you started experimenting with startups. So how did the whole startup world come knocking?

Vadim Rogovskiy: That’s a good question. Because before I turned 18, I never actually had a clear conviction that I wanted to become a founder. My dad had been building a career his entire life, so I always thought I was going to be like him—and I tried.

Vadim Rogovskiy: I had a few early jobs. When I was a freshman—or maybe in my second year at university—I worked with a couple of software companies. I worked at an online casino, and I worked at a software development shop. But I didn’t like it. I was probably fired a few times because I disagreed with my bosses.

Vadim Rogovskiy: Then I just got fascinated with the idea of having some pet projects. The internet was a lot of fun. I didn’t even think about money or any kind of monetary outcome—it was more about fun. It was cool and interesting. That’s how I started playing with it, treating it like a game, before I even realized it could become something serious.

Alejandro Cremades: Well, it became serious with AdCenter. So tell us what happened there.

Vadim Rogovskiy: Yeah, so actually, one of the software companies I worked for had a project that was basically an ad network—connecting advertisers with websites where they wanted to place ads. I was responsible for creating documentation that described the functionality for the development team.

Vadim Rogovskiy: And I became kind of an expert in design—auctions, ad placements, dynamic pricing, etc. That’s when I started learning more about the industry overall.

Vadim Rogovskiy: During that time, I had a few businesses already. One of them was a social media marketing agency called Face-to-Face Media. It was a small agency—my pet project. We were helping Ukrainian local businesses promote on Twitter, Facebook, and the local social network VK.com.

Vadim Rogovskiy: I became an expert in social networks and how to promote a business there. Then I realized there was an opportunity to help businesses use ad networks built into social media platforms—like Facebook ads or LinkedIn ads. This was back in the early days when they had just added APIs that could be used remotely.

Vadim Rogovskiy: The interfaces back then were really bad. If you remember the interface for Facebook ads or VK.com ads from 14 years ago—they were super primitive.

Vadim Rogovskiy: So, I went to VK.com’s headquarters. We struck a deal to use their API—we committed to bringing them more revenue, as I already had access to small businesses.

Vadim Rogovskiy: Locally, we built a platform and started promoting local businesses there. We tried to scale it outside Eastern Europe, but at the time I didn’t have enough experience.

Vadim Rogovskiy: Around that time, smartphones were becoming more meaningful. iPhone and Android apps were on the rise. We started exploring the idea of running ads there. That gradually evolved into a separate company, which we later called Clickky.

Vadim Rogovskiy: At some point, I realized I was working on two companies. AdCenter was doing fine, but we couldn’t scale it beyond Eastern Europe.

Vadim Rogovskiy: So I decided to sell it. One of the companies I had worked at before AdCenter was a US-based company called Vertomedia, which later became IntelliGen. When I decided to sell, I reached out to a few people, and one of them—the owner of VPN—agreed to buy it.

Vadim Rogovskiy: They had display ads, pay-per-click, contextual ads, but nothing on social. So it was a very relevant add-on for their product and team.

Vadim Rogovskiy: For me, at 25, it was very meaningful. I bought a house, a Porsche, and a few other things. I was having fun.

Vadim Rogovskiy: Then I switched to Clickky. So maybe you have some questions on that?

Alejandro Cremades: I mean, probably the listeners are wondering—what kind of Porsche did you buy?

Vadim Rogovskiy: I bought a Cayenne Sport—and I also upgraded it.

Alejandro Cremades: Very nice.

Vadim Rogovskiy: It was one of the loudest Cayennes in Odessa at that time.

Alejandro Cremades: Good choice. Now, your next company was Clickky, which you actually started before AdCenter had even wrapped up.

Alejandro Cremades: So tell us about Clickky. What was that journey like? Because with Clickky, you guys even tried M&A, but the timing was off. So, before we get into that—what’s the origin story of Clickky, and how did you go about building the ARR? Because you stayed away from raising money until you already had millions in annual recurring revenue.

Vadim Rogovskiy: Yeah, so the idea was that Clickky didn’t use any APIs. It was specifically a marketplace for publishers and advertisers.

Vadim Rogovskiy: We didn’t even start in mobile. It really took off in mobile later. But initially, while I was still working on AdCenter, the same team and I did some experiments—we tried placing ads inside social media and gaming apps on Facebook and VK.com.

Vadim Rogovskiy: It went well, but the market was very small at the time. We grew fast at first, but when we hit $20,000–$30,000 a month, we got stuck. There was a lot of competition—we were one of the first, but I didn’t know how to scale. I didn’t feel the market dynamics yet.

Vadim Rogovskiy: I couldn’t zoom out and get a helicopter view like I can now. Back then, I was just in a race—without stepping back to look at the opportunity holistically.

Vadim Rogovskiy: Then we saw the mobile opportunity. App developers were launching apps for mobile—it was even earlier-stage than social apps. So we quickly built a proof-of-concept ad server for mobile, and it took off immediately.

Vadim Rogovskiy: Basically, imagine you’re an app developer—you have a game or a taxi app—and you need targeted users installing your app in the U.S., in New York, for example. You come to Clickky, we quote you $3 per install, and we place those ads inside other apps or websites with mobile traffic and available inventory.

Vadim Rogovskiy: We built the platform with our own IP. At the time, there were no third-party ad servers—you had to build everything from scratch. And that’s what we did.

Vadim Rogovskiy: It was a bootstrapped company. At the time, I didn’t even know it was called that. I thought that was the only way to build a business. It was profitable—but not by much—because we had to keep reinvesting in growth.

Vadim Rogovskiy: At that time, I also thought I needed to have a bigger team.

Vadim Rogovskiy: I had ambitions to build a very big team. I believed that people were the solution to every problem. So, as our revenue grew, our costs grew as well.

Vadim Rogovskiy: But still, we were profitable and growing very fast. We went from zero to almost $4 million in annual revenue in just three years.

Vadim Rogovskiy: And then, yeah, some VCs started to approach me because we started to gain visibility. I began speaking at conferences, and I was also running…

Vadim Rogovskiy: …the biggest conference on mobile marketing in Eastern Europe—called Mobile Beach Conference—because it took place on the beach every summer in Odessa. The largest one had around 1,000 attendees. We brought in a lot of speakers, many of whom were visiting Ukraine for the first time—from Facebook, Google, you name it.

Vadim Rogovskiy: So yeah, we became visible, and some people started to approach us about investing. I didn’t really understand why I should raise capital, because I didn’t yet realize we could grow even faster or get expertise we didn’t have.

Vadim Rogovskiy: But one VC was very persistent. They offered us secondaries.

Vadim Rogovskiy: At that time, I had only one investor. It was the same person who acquired AdCenter—part of the deal was that he could invest in Clickky. So, he put a small check into Clickky and was the only investor.

Vadim Rogovskiy: The fund offered us secondaries, and we raised $2 million. Half of the round was used to buy shares from us, and the other half went to the company.

Vadim Rogovskiy: Then we grew 3x from that moment over two years. We closed the round in 2015. By 2017, we had $13.5 million in revenue.

Alejandro Cremades: So, at this point, you started receiving inbound M&A interest—and you learned a tough lesson. That lesson was all about timing. Tell us what happened.

Vadim Rogovskiy: Yeah, that’s a very good question. We were growing super fast, and I was receiving interest—not formal offers, but discussions. Either it wasn’t serious or the offers were below our expectations.

Vadim Rogovskiy: But I wanted to sell. Ultimately, with Clickky, that was the outcome I wanted. But I wanted to sell it later—after hitting $20 million in revenue.

Vadim Rogovskiy: Then the market started to downturn. Around 2017, there were so many companies competing to deliver mobile installs to apps growing in the App Store and Google Play that bad actors started to enter the space.

Vadim Rogovskiy: By bad actors, I mean fraudulent players—like bot farms. You’ve probably seen pictures of warehouses full of thousands of iPhones in China.

Vadim Rogovskiy: These iPhones were running 24/7, constantly installing different apps. Because of that, big advertisers started pulling out of the channel entirely and began suing their agencies.

Vadim Rogovskiy: The structure worked like this: you had companies like Uber or major gaming publishers working with agencies, and those agencies worked with companies like us.

Vadim Rogovskiy: So when advertisers—like Uber, whom we promoted, though not directly—started pulling out, it affected the entire industry. Multiples dropped. Budgets dropped.

Vadim Rogovskiy: That’s when we realized it was time to sell. But by then, it was already too late. Multiples were in free fall. Even public tech companies were being valued at just 0.1–0.5x revenue.

Vadim Rogovskiy: We got a decent offer—considering the circumstances—but mostly in stock, from a company planning to IPO soon.

Vadim Rogovskiy: We accepted the offer. We entered due diligence. But then their business began to struggle.

Vadim Rogovskiy: They also started behaving unethically. They solicited my top managers. By that time, I had already introduced a new CEO—though I remained highly involved—and they even solicited him. He began consulting for them. It was a bad story.

Vadim Rogovskiy: A series of unfortunate events led to us closing the business. Once the deal fell apart…

Alejandro Cremades: Wow.

Vadim Rogovskiy: …the team was demotivated. We didn’t have enough runway. I tried to save it, but by then, I already understood—yes, that’s it.

Vadim Rogovskiy: What helped me get through that tough lesson more easily was that, by then, I had introduced the new CEO and transitioned to a chairman role. I had already begun investing in a new company.

Vadim Rogovskiy: My main takeaway was: it’s never too early to sell.

Vadim Rogovskiy: I later spoke with many founders who had sold their companies. I was curious about their perspectives. I never heard anyone regret selling too early.

Vadim Rogovskiy: But I met so many people who regretted trying to sell too late.

Alejandro Cremades: No kidding. Timing, timing.

Alejandro Cremades: So, after this, you did a bunch of things—a venture studio, startup accelerator called Wannabies.

Alejandro Cremades: But one thing led to the next. As you said, you began investing in startups. And one of those investments became your next chapter—3DLook. So how do you go from being an investor to suddenly becoming the CEO of the company? What were you guys doing at 3DLook?

Vadim Rogovskiy: With 3DLook, it was more of a venture studio track. I had the idea: what if we…

Vadim Rogovskiy: I was looking to incubate a company while still running Clickky. But I wanted to find something interesting outside of ad tech because I was exhausted from that market.

Vadim Rogovskiy: I was fascinated with augmented reality, computer vision, and what could be done with a smartphone camera. This was early 2016.

Vadim Rogovskiy: Around that time, Snap acquired a Ukrainian-born company called Looksery—it was founded by my friend. That also inspired me because they brought the lenses to Snap—the facial masks.

Vadim Rogovskiy: I thought, okay, what can we do with computer vision, using deep technical talent from Ukraine and my experience selling to big businesses outside of Ukraine?

Vadim Rogovskiy: That’s how the idea for 3DLook was born: what if we create a solution that allows anyone to scan their body with a smartphone—just by taking two pictures, front and side—

Vadim Rogovskiy: —and then generate a very accurate 3D model with all the measurements, etc. Luckily, I had a friend who was an experienced product manager.

Vadim Rogovskiy: He left his previous company and offered to run the project in the early stages, which was very technical.

Vadim Rogovskiy: So I started financing it. He hired developers and built early prototypes. Only about a year later did I realize how fascinating and promising it was.

Vadim Rogovskiy: I saw the future potential and decided to join full-time. I was already the major shareholder since I was financing it, but that’s when I joined as CEO.

Alejandro Cremades: Quite the journey. You guys raised $16 million, and things seemed to be heading in the right direction. But one thing I want to ask is: when do you decide it’s time to step down as CEO of a company?

Alejandro Cremades: You were leading for—what, eight years or so? That’s quite a long time. When do you realize it’s time to turn the page?

Vadim Rogovskiy: Yeah, I mean, it’s a very controversial topic for many founders. But in my case, I knew…

Vadim Rogovskiy: At one point, 3DLook was growing fast. We went from $100K in ARR to $1 million in just one year.

Vadim Rogovskiy: We raised a $10 million Series A on top of that growth in 2021. But then we got stuck because the mobile body scanning market was still early.

Vadim Rogovskiy: Our bet was that it would become pervasive—every consumer scanning their body with a phone to buy clothes, use it in fitness apps, send the data to doctors, etc.

Vadim Rogovskiy: That did start to happen—but only in niche use cases. For example, every policeman in the U.S. can now order properly fitted body armor using our tech.

Vadim Rogovskiy: But those are narrow use cases. Only early adopters and innovators were using it—even among big enterprises.

Vadim Rogovskiy: It didn’t become pervasive.

Vadim Rogovskiy: The company had to reach break-even to remain sustainable. I realized I wasn’t having fun anymore—and hadn’t been for a while—because the company needed something else.

Vadim Rogovskiy: It wasn’t just about fun. I realized I wasn’t bringing enough value anymore. The company needed a different type of CEO—more operationally focused.

Vadim Rogovskiy: Someone to operate the business like a business, not a startup. I realized it was time to move on.

Vadim Rogovskiy: I spent time negotiating with my board last year. Eventually, we agreed on everything—they supported me.

Vadim Rogovskiy: One of the main reasons they supported me was because I had a great candidate for CEO.

Vadim Rogovskiy: Kate. She worked with me from the early days of the company. She tried many different roles and grew with the company.

Vadim Rogovskiy: So she was a great candidate, and now she’s—actually—she’s killing it. I mean, she’s doing great, and she’s doing some things better than I did.

Vadim Rogovskiy: And it’s, of course, a new experience for me—watching someone else run your company from the sideline—and feeling happy about it. Yeah.

Alejandro Cremades: Now, in your case, after this, you tested the whole venture capital thing. You went at it. You invested in like 60 startups yourself, and then you also dove into it from the VC side with an early-stage fund.

Alejandro Cremades: Why did you realize that wasn’t for you?

Vadim Rogovskiy: Yeah, I always wanted to try being a VC. I always thought VC was the best job in the world because, you know, you tap into different industries, you learn a lot, everyone wants you, you’re the most popular person out there.

Vadim Rogovskiy: But the thing is that—yeah—I mean, it was a great experience, and I really learned a lot about different industries. I had a holistic view on all the industries, trends, etc. But what I didn’t like was that…

Vadim Rogovskiy: I’m still a builder. I still have a founder’s mentality.

Vadim Rogovskiy: And I just didn’t feel like we were actually creating any value…

Vadim Rogovskiy: …outside of the relatively small checks we were giving to founders. I was responsible, as a partner, for our portfolio. So as soon as we invested, I would jump in and coach founders. Some were coachable, but many just wanted the check and didn’t want to hear from us again.

Vadim Rogovskiy: I just didn’t feel like we created any new value. And I realized—yeah—I still want to create value by operating. That’s why I decided that even though I had a choice to become a full-time VC for the next 10–20 years, it’s probably not the journey for me.

Alejandro Cremades: Now, in your case, you decided to take on two things at the same time. One is riding the whole AI wave. The other is buying and optimizing for cash-flowing companies.

Alejandro Cremades: Tell us about those two routes. Doing just one thing is already tough—you’re doing them both in parallel.

Vadim Rogovskiy: Yeah. I mean, I realized that last year was a year of transition for me, right? I was leaving my company as CEO. It wasn’t easy to make that final decision.

Vadim Rogovskiy: I went through a lot of self-reflection and realized—yeah—first of all, the founder mindset of building companies, especially from zero to one, is what I want to do for the rest of my life.

Vadim Rogovskiy: Secondly, I’m still a happier and more fulfilled person when I’m doing something on the side. And by “something,” I mean more like investing or mentoring—because it allows me to switch context. It allows me to zoom out and look at my company from a different angle.

Vadim Rogovskiy: That’s my recipe, right? So my main focus is still running my new startup as CEO. But I also discovered a new asset class, a new opportunity. Because when I was a VC, we had a bunch of startups that…

Vadim Rogovskiy: …built good, healthy early-stage businesses, but they weren’t investable. They raised money from us, but couldn’t grow fast enough to attract more capital.

Vadim Rogovskiy: And they got stuck for a few years. These founders had very limited liquidity options. If you’re making $1–2 million in ARR, it’s hard to sell to anyone—even strategic or financial investors.

Vadim Rogovskiy: That’s why I realized—what if there was a kind of vehicle, like a micro-PE fund, to buy these businesses? Let the founders be free so they can do something else. Maybe at least provide some return to investors.

Vadim Rogovskiy: Of course, it’s not just about making money—it’s about closing that chapter gracefully and growing these businesses. What my team and I do well is moving upmarket—building a go-to-market machine to sell to enterprises.

Vadim Rogovskiy: That’s the thesis. I have a business partner in London—she brings strong corporate finance and VC experience.

Vadim Rogovskiy: We’ve looked at more than 100 companies in the $1–5 million ARR range. And hopefully, soon, we’ll be announcing the first few.

Vadim Rogovskiy: So this, for me, is a combination of entrepreneurship and investment. It’s called entrepreneurship through acquisition.

Vadim Rogovskiy: I believe in this model because there are lots of startups that overraised—especially in 2021 and 2022.

Alejandro Cremades: Oh yeah—the COVID valuations. Those were something else.

Vadim Rogovskiy: Yes. And now you have so many opportunities to buy these assets, buy these companies, and help set the founders free.

Vadim Rogovskiy: Because at some point, for founders, the main thing is…

Vadim Rogovskiy: …letting go of ego. Ego is always the main enemy for founders. When they let go of their ego, they realize it’s about…

Vadim Rogovskiy: …gracefully finishing one chapter and properly switching to another. Yeah.

Alejandro Cremades: For sure. I think one of the problems with founders is when they become the company—when they’re attached to being the company. That can become toxic and really bad.

Alejandro Cremades: So in this case, the other route you’re pursuing in parallel is EVE. Tell us about EVE.

Vadim Rogovskiy: Yeah. EVE is my main focus—my startup number four. We want to replace executive assistants. Meaning, we want to replace humans in EA roles.

Vadim Rogovskiy: Right now, you can get an executive assistant from an offshore country for $3,000 a month, on average. We want to give it to you for 10% of the cost.

Vadim Rogovskiy: And we want to replace at least 80% of the functionality.

Vadim Rogovskiy: We already have our first use case in private beta: autopilot schedule management. EVE manages your schedule—scheduling, rescheduling—based on your preferences. It’s not like Calendly or Cal.com, which just fill open slots.

Vadim Rogovskiy: No—here, it’s like working with a human.

Vadim Rogovskiy: EVE remembers your preferences, gets better with every conversation, and keeps everything in memory.

Vadim Rogovskiy: We’re going to add more use cases. We started with individuals through a waitlist—we already have one. Then we’ll go after teams.

Alejandro Cremades: So obviously, in a world where EVE’s vision is fully realized, what does that world look like?

Vadim Rogovskiy: It’s a world where every human has an AI extension…

Vadim Rogovskiy: …sitting in all your communication channels, representing you—filtering out 80% of noise, low-priority threads, conversations, etc.—so you can focus only on what truly matters.

Vadim Rogovskiy: Everything else runs on autopilot. It’s about extending human capability.

Vadim Rogovskiy: I believe in that future—and we’re trying to make it happen.

Alejandro Cremades: Talking about the future, I want to talk about the past. After doing four startups, being on the VC side, all of it—let’s say I bring you back in time to when you were 18, just starting to experiment in the venture world.

Alejandro Cremades: If you had a chance to sit down with that younger self and offer one piece of advice for launching a business, what would that be—and why?

Vadim Rogovskiy: Hmm. Great question.

Vadim Rogovskiy: I would probably tell myself to launch my first company in the U.S. and move there much earlier than I did.

Vadim Rogovskiy: It would’ve definitely accelerated my trajectory.

Vadim Rogovskiy: And I’d also say this: a founder fails only when they stop building.

Vadim Rogovskiy: It’s not about the outcomes. It’s not about exit sizes—or even exits at all. It’s about the path. It’s the journey.

Vadim Rogovskiy: If you keep building, you’ll always be happy and fulfilled.

Alejandro Cremades: For those listening who’d love to reach out and say hi—what’s the best way to do so?

Vadim Rogovskiy: I’m regularly posting useful stuff on LinkedIn, and I’ll soon be launching my email newsletter. So, find me on LinkedIn.

Vadim Rogovskiy: And we also have a waitlist for EVE—maybe I can share that as well.

Alejandro Cremades: Amazing. Well hey, Vadim, thank you so much for being on The DealMaker Show today. It’s been an absolute honor to have you with us.

Vadim Rogovskiy: Thanks, Alejandro.

*****

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