Dear readers,

This week’s edition focuses on a theme that increasingly defines the SEE startup ecosystems: founders from relatively small markets building companies with global ambitions. 

From Bitola-born entrepreneur Aleks Tomovski becoming the first Macedonian founder accepted into Y Combinator while taking on enterprise software giant ServiceNow with AI agents, to a wave of funding rounds, exits, and acquisition milestones across the region, the message is becoming harder to ignore. 

Geography matters less than it once did, but mindset still matters enormously, and in that sense we also look at Nvidia’s acquisition of Kumo.ai, giving Macedonian entrepreneur Vanja Josifovski a major exit, new capital flowing into Bulgaria’s fintech sector, the first exit milestone for Zephyr Angels, and the launch of a new European social platform from Romania. 

To round things off, angel investor Gogo Rafajlovski shares where investors are placing their bets in 2026, why conviction is becoming more concentrated, and why traction is once again speaking louder than hype. 

Enjoy the read!
Bojan Stojkovski
Editor-in-Chief, IT Logs

I first met Aleks Tomovski in a Greek restaurant in San Francisco’s Dogpatch neighborhood, a part of the city that still carries traces of its industrial past but now sits inside one of the most expensive and competitive experiments in modern capitalism. 

Warehouses have been converted into offices, startups occupy former loading docks, and venture capital firms sit a few blocks away from AI labs running models that are already changing the way how software is written.

At first glance, he didn’t stand out in that environment. Aleks has the familiar rhythm of someone deeply embedded in startup culture: fast speech, constant mental switching between product, engineering, and market dynamics, and an ease with technical topics that suggest years of experience in the same ecosystem. 

In San Francisco, that profile is common enough that it becomes almost invisible. You assume he’s in his early 20s and has gone through Stanford, or Berkeley, or a long line of Bay Area startups.

So I asked the questions.

How old are you? “Thirty-six.”

Stanford? He laughed. “No. Technical Faculty in Bitola.”

How long have you been in San Francisco? “Since late March.”

Bitola and the absence of a startup default

Bitola is a city of roughly 70,000 people in N. Macedonia. It is large enough to function as a regional center, but small enough that social and professional expectations remain relatively constrained. In environments like that, career paths tend to be familiar ones - you become a doctor, an engineer, a civil servant, or you leave. 

Aleks grew up inside that structure, where stability is often treated as the rational objective function. Not because people lack ambition, but because the system rewards predictability, and risk-taking is seen as deviation.

What makes his trajectory unusual is not that he rejected that framework, but that he encountered an alternative one early enough to make a difference. As he explains, his father made a decision that would quietly change everything. Rather than buying a nicer family car, he used that money to fund Aleks' exchange year in the US, a deliberate act of belief that ended up reshaping how his son saw the world. 

That year became a reference point for how he evaluates work and opportunity. In the US, he encountered a labor market logic that was almost opposite of what he had known.

What followed over the next years was a sequence of environments that functioned more like distributed case studies in startup dynamics.

Vilnius, Riga, Denver, Tel Aviv, Singapore, Hong Kong, Kuala Lumpur, Melbourne.

Each ecosystem had different constraints, but the underlying patterns were similar: small teams trying to build under uncertainty, limited resources forcing prioritization, and repeated cycles of product iteration driven by market feedback rather than internal planning.

At one point he returned to N. Macedonia and joined another startup during a growth phase, working inside a company that was transitioning from early-stage ambiguity into more structured execution.

Then came Australia, and with it a different type of constraint entirely: not product-market fit, but immigration systems. A visa process that was expected to take days stretched into nearly two years due to shifting rules and administrative delays. Instead of pausing his trajectory, he and his family moved across Asia while waiting.

That period removed any remaining assumption that external systems would align with personal timelines. “You realize at some point that planning is not a guarantee, simply because of the passport you were born with.” Aleks tells IT Logs.

Wix, Canva, and learning from failure loops

At Wix, where he joined as one of the early employees working on Wix Code, he saw startups from a different angle: execution under real operational constraints, including enterprise clients and production systems that could not afford instability. This was also where he developed a more grounded understanding of how product decisions actually accumulate over time.

Canva represented a different stage entirely. By the time he joined, it was already a global-scale company. For many engineers, it would have been a destination role: strong compensation, high-caliber teams, and technical problems at scale.

He spent three years there, eventually becoming a senior engineering manager working on the core editor, one of the company’s most important product surfaces. Externally, it looked like a stable endpoint, but internally, it created a different kind of tension.

During this period, he also witnessed the early emergence of AI tooling that would later redefine software development speed. That shift acted as a signal that the cost structure of building products was about to change.

Over roughly two years, the focus gradually narrowed toward enterprise software and automation, particularly workflows that were still heavily manual and fragmented inside organizations.

In January 2025, he made the decision to leave Canva. On paper, it looked like a founder leaving a successful company at the top of its curve, which is often how these decisions are later simplified. Internally, however, the logic was more structural than emotional.

Modern began building its product in late 2025, entering the enterprise service management space dominated by systems like ServiceNow. Aleks describes the starting point in simple operational terms. “Every company has an internal service desk. All requests, questions, and issues end up there.”

Modern’s bet is that this model is shifting from tracking work to executing it. “What we’re building is a system of action. Agents don’t just manage tickets, they drive them to completion.” he explains.

The idea is to introduce always-on/ambient agents that actively work each request toward resolution. But unlike consumer AI tools, enterprise environments require determinism. “If someone asks for AWS access, it has to be exact. You cannot afford probabilistic behavior.” he explains.

To solve this, Modern combines AI reasoning with a deterministic execution layer made up of structured workflows expressed as code, or “skills,” built on top of its own SDK and runtime. “You want the AI to understand the problem, but the actual execution has to be controlled and reliable.” Aleks explains.

On top of this sits what the company calls ambient agents. These are persistent systems that do not wait for prompts but actively orchestrate ticket resolution, coordinating systems and escalating to humans when needed.

50 investor calls, bunch of NOs and a Y Incubator YES

Fundraising introduced a different kind of system entirely. Over roughly 50 investor conversations, spread across regions and time zones, the pattern initially looked uniform. A pitch, a follow-up question or two, and then a version of no that rarely felt final, but rarely turned into anything else either.

The early phase of fundraising is less about capital and more about calibration. Founders are effectively testing how their narrative lands across different mental models of risk. Some investors react to traction, others to timing, others to founder-market fit, and many to combinations that are not explicitly stated.

During that process, patterns eventually emerged. In Europe and parts of Asia and Australia, conversations tended to move more slowly, often requiring longer validation cycles and additional proof points. In the US, the decision curve was much more compressed.

Their first Y Combinator application was rejected after the interview step. At that stage, the company was still forming. There was direction, but not yet enough execution evidence to make it happen. Y Combinator, like most structured accelerators, is less interested in ideas and more interested in demonstrated motion.

The interview request arrived much later, when they were close to closing their initial pre-seed round. YC interviews are famously short, but not casual, as they squeeze decision-making into a very small window.

However, arrival at Y Combinator does not function as a finish line. If anything, it removes the last layer of ambiguity about whether the company exists in a serious ecosystem. Suddenly, founders are exposed to companies operating with different assumptions about growth, capital, and ambition. 

In Silicon Valley, the default expectation is different. Ambition is not something to be justified upfront - it is something to be assumed and then validated later through execution. “You can get into a Waymo, drive around the city and go sell to the biggest companies you can think of. And the Y Combinator logo does open lots of doors.” 

From observation to participation

At one point, he describes his earlier career using a metaphor that captures a deeper psychological transition about becoming a part of Y Combinator. “It felt like I was always watching the match from the bench. I could see everything clearly, the tactics, the mistakes, the opportunities, but I wasn’t actually part of it.”

However, Aleks’ home town of Bitola remains a reference point throughout the conversation, as it represents a scale where ambition is often socially visible and structurally constrained at the same time.

But, he is careful not to frame it as limitation and instead, he describes it as context. “There are now founders in Macedonia who think globally from day one. That wasn’t common before. So, something has changed in how people define what is possible.”

The change in mindset though is not uniform, and it is not complete. Access to global tools, global markets, and global distribution has begun to remove some of the traditional constraints of geography. Still, the change of mentality is slower than the technical one and the final image he returns to is simple.

2026 will redefine IT as a strategic driver of global growth. Automation, AI-driven support, unified platforms, and zero-trust security are becoming standard, especially for distributed teams. This toolkit helps IT and HR leaders assess readiness, define goals, and build a scalable, audit-ready IT strategy for the year ahead. Learn what’s changing and how to prepare.

Download the Toolkit

IT Logs: Where is the smartest money going this year?

IT Logs: Bigger bets on fewer startups, or smaller checks spread wider?

IT Logs: What is moving valuations more in 2026: real traction, AI buzz, or solid unit economics?