This 4x Founder-Investor Built & Exited Companies And Is 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.

Born in Odessa in Ukraine, Vadim’s journey spans ad tech, computer vision, venture capital, AI, and even micro-private equity. Through it all, he’s kept the same compass: a passion for building, a bias toward action, and a growing sense of perspective — forged through both wins and scars.

Listen to the full podcast episode and review the transcript here.

From Odessa to Ad Tech: Early Days and First Wins

Vadim’s roots shaped his drive. Raised in a coastal city similar to cosmopolitan San Francisco with a heavy mix of cultures, he came from a humble background. His father is a telecom engineer turned professor at Polytechnic University, and his mother is a piano teacher.

Vadim studied business management at a Ukrainian university, but his real education came when the internet sparked his imagination. While at university, he worked a few jobs at a software company, an online casino, and a software development shop.

Vadim recalls, “Before I was 18, I never thought I’d become a founder. My dad had a stable career, and I thought I’d follow in his footsteps. But I kept getting fired from early jobs — I just didn’t like taking orders.”

Building AdCenter and Face 2 Face Media

Fascinated by the internet, Vadim started building pet projects. What began as a creative outlet turned serious with his first real startup: AdCenter, a social media ad platform that helped local Ukrainian businesses advertise on networks like Facebook, Twitter, LinkedIn, and VK.com.

Vadim was responsible for creating ads describing the development team’s functionality or documentation. He soon became an expert in designing, auctions, ad placements, dynamic pricing, and more, learning about the industry.

By then, Vadim had already founded a social media marketing agency, Face 2 Face Media. Between running his two companies, Vadim gained extensive experience in social networks and promoting businesses on them.

Vadim negotiated API access from VK.com, built an interface to support local SMBs, and sold the company to VertaMedia, a US-based ad tech firm. Although AdCenter was doing well in the local market, Vadim found it challenging to expand beyond Eastern Europe; an exit seemed like the perfect option.

Before building AdCenter, Vadim had worked for VertaMedia, which later became Adtelligent. He knew the owner well, and they expressed interest in purchasing the company since they wanted to display ads. VertaMedia had pay-per-click and contextual ads but wanted to move to social media.

At 25, with his first exit under his belt, Vadim bought a Porsche Cayenne Sport (“the loudest in Odessa,” he jokes) — and rolled into his next venture.

Clickky: From Zero to $13.5M ARR

Vadim’s next venture, Clickky, started as a side project while AdCenter was still alive. Initially focused on placing ads in Facebook and VK apps, Clickky hit its stride in mobile advertising, connecting iPhone and Android app developers with publishers to drive installs.

Clickky didn’t use any APIs and was basically a marketplace for publishers and advertisers. Vadim started the company with the same team he had worked with at AdCenter. Their initial attempt was to place ads inside social media and gaming applications on Facebook and VK.com.

Although the market seemed to take off initially, Vadim hit the competition roadblock. He was unsure how to scale the company and the market dynamics. However, he recognized the opportunity of placing ads in mobile phone apps.

Clickky offered performance-based installs for app developers—$3 per user, for example—and handled the backend infrastructure from scratch. With no third-party ad servers, Vadim and his team built their own ad tech stack, growing revenue to nearly $4M ARR within three years.

Vadim’s strategy was to grow the team, and although their costs were increasing, the company was also generating revenues and was profitable. It grew quickly, attracting attention from VCs.

Vadim also recalls running the Mobile Beach Conference, the biggest conference on mobile marketing in Eastern Europe. It had 1,000 attendees, with speakers from the top tech companies globally, including Google. The exposure was tremendous.

The M&A That Got Away

“Clickky was 100% bootstrapped. I didn’t even know the word ‘bootstrapped’ — I thought that’s just how you built a company,” Vadim explains. In 2015, they raised $2M, with half of it going toward secondaries.

After that, Vadim and his team scaled 3x in two years, hitting $13.5M ARR by 2017. But while inbound M&A interest started appearing, Vadim hesitated. He preferred waiting to hit $20M before selling. “That was my biggest mistake. We should have sold sooner,” he concedes.

By late 2017, the mobile ad market was imploding. Fraudulent bot farms were churning fake installs at scale, causing major advertisers to pull back. Multipliers and budgets collapsed. Even public tech companies were selling for 0.5%, 0.1%, 0.2%, or 0.3% to revenues.

Although Vadim got a promising M&A deal — mostly in stock — it fell apart when the buyer started poaching Clickky’s leadership. Morale dropped. Runway vanished. And Clickky was shut down.

Vadim’s biggest takeaway? “I’ve never met a founder who regretted selling too early. But I’ve met so many who regretted selling too late.” That insight would guide his next chapters.

3DLook: Scanning Bodies and Building the Future

After Clickky, Vadim shifted to a venture studio model, incubating new ideas while investing in startups. These projects included WannaBiz, Cash Cow Labs, and Geek Ventures.

One was 3DLook, a startup that leverages smartphone cameras and computer vision to scan bodies in 3D. Using just two photos, it gets an accurate 3D model with precise measurements.

Vadim recalls that, at that time, he was fascinated with everything related to augmented reality and computer vision. The concept was inspired by Snap’s acquisition of Looksery in early 2016. Looksery was an AR startup with Ukrainian roots, and Vadim firmly believed in deep Ukrainian technical talent.

What began as a side project eventually pulled Vadim back into the CEO seat. “It was just too exciting. The potential was huge — imagine people scanning themselves to shop online, get fitted uniforms, or track fitness progress.”

3DLook raised an initial $16M round and grew fast–from $100K to $1M ARR–in a year. It then raised a $10M Series A in 2021, finding traction in niche verticals — like helping US police officers get body armor that fit — but mass-market adoption lagged.

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Eventually, 3DLook had to reach a break-even point and run like a business. Vadim realized it needed a different kind of CEO — one who could scale an operationally intensive company.

He stepped down, replacing himself with Kate, an internal leader who had grown within the company. Today, she runs the business — and is “killing it,” according to Vadim. “It was hard to watch from the sidelines, but also a proud moment. She’s doing some things better than I did.”

The VC Experiment: Popular But Powerless

Vadim always believed being a VC would be the dream job: smart people, exciting industries, trends, and access to everything. He joined an early-stage fund and invested in 53 startups there. But he quickly found it unfulfilling.

“We weren’t creating real value. Some founders were coachable, but many just wanted the check. I missed building.” Vadim realized he was still a founder at heart — not an observer. So, he moved on, taking on two ventures simultaneously–both deeply rooted in his founder identity.

Reflecting on his VC stint, Vadim came across several healthy, early-stage startups that were not investable since they raised funding but could not grow fast enough so other people could invest in them. In a few years, they would stagnate because they had minimal liquidity options.

These companies were just too small, making $1M to $2M ARR, which is hard to sell to strategic or financial investors. That’s when Vadim thought of creating a micro PE fund to purchase these companies and let the founders exit. The objective was to ensure that investors got some returns.

Vadim connected with his partner, who has experience in VC and corporate finance. Together, they would grow the small companies and develop their go-to-market infrastructure before selling them to enterprises. The duo considered more than 100 companies with an ARR of $1M to $5M.

From Vadim’s perspective, their strategy was like a combination of entrepreneurship and investment. He calls it entrepreneurship through acquisition.

EVE: The AI Executive Assistant

Vadim’s fourth startup, EVE, aims to replace human executive assistants with AI. Unlike basic scheduling tools, EVE learns your preferences, understands context, and handles 80% of a VA’s tasks — from scheduling to prioritizing messages. It can even improve with every conversation.

“At present, you can get a remote executive assistant from an offshore country for $3K a month. We want to give you an assistant for 10% of the cost of a human. Not just a calendar tool — a real assistant that gets better with time.”

EVE is in private beta now–autopilot schedule management–starting with individuals before expanding to teams. The long-term vision? Autopilot for your professional life—so you can focus on high-impact decisions while AI handles the rest.

AI can filter 80% of noise, 80% of less important threads, conversations, etc., thus extending human capabilities.

A Founder for Life

Through each chapter — from Odessa to AI, from mobile ads to body scanning, from VC to acquisition — Vadim Rogovskiy’s story is one of evolution. But the core has never changed. He’s a builder. A zero-to-one guy. Someone who prefers creating value over chasing prestige.

“The founder mindset — that’s what I’ll keep for life. And now, I’ve found my rhythm: run one company, and always have something else on the side to zoom out, learn, and reset.”

In a world of hype cycles, boom-and-bust valuations, and exit FOMO, Vadim’s story is a rare, honest reminder: startup life isn’t just about winning. It’s about learning, letting go, and building again.

Listen to the full podcast episode to know more, including:

• 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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