Ross
Haleliuk

He did not start in security. He started in history. Specifically, Russian history, in Ukraine, before the internet was much of anything and before "cybersecurity startup" was a viable career path. Ross Haleliuk has one of those careers that makes sense only in retrospect - a series of pivots that look like a straight line once you zoom out far enough.

At 22, he packed up and moved to Canada. Vancouver. He learned English properly, picked up business analysis, moved into project management, wandered through fintech, co-founded a B2B edtech company, and eventually landed in cybersecurity. He did not land gently. He landed with the kind of enthusiasm that produces newsletters, bestselling books, angel syndicates, and community organizations - all simultaneously.

The newsletter came first. "Venture in Security" launched on Substack with a simple premise: the cybersecurity industry is massive, complex, and opaque, and there is almost no serious analysis written specifically for the people trying to build within it. Not for hackers. Not for enterprise CISOs. For builders - founders, product managers, investors, and operators who need to understand the business before they can navigate it.

Ross understood that market because he was inside it. As Head of Product at LimaCharlie, a cybersecurity infrastructure company, he had spent years watching founders make the same expensive mistakes - not because they lacked technical talent, but because nobody had written down the playbook. So he wrote it.

"Cyber for Builders: The Essential Guide to Building a Cybersecurity Startup" landed in January 2024 and immediately hit Amazon's #1 in Cloud Computing. The 4.8-star rating from 100+ reviews tells you this was not a rushed cash-in. The book features forewords from Caleb Sima and Jeremiah Grossman, contributions from 50+ entrepreneurs, operators, investors, and thought leaders, and covers everything from understanding investors to why cybersecurity startups fail. It won Book of the Year at the SANS Cybersecurity Difference Makers Awards. That is not a small thing.

But the book is almost a byproduct of the method. Ross is a researcher first. In 2022, he analyzed over 800 cybersecurity products from more than 600 vendors to produce a product-led growth market map that ran on TechCrunch. That kind of work - unglamorous, granular, and genuinely useful - is what built his audience. By the time the book came out, 21,000 people were already reading his newsletter every week.

The community work runs parallel. Building Cyber Collective has connected more than 220 founders, advisors, and investors through a double opt-in system. No strings attached. Free. The Venture in Security Angel Syndicate, which Ross co-leads, is the world's first angel syndicate designed exclusively for security practitioners investing their own capital - not a fund with a 10-year exit clock, but practitioners who understand the problems they are solving from the inside out.

In June 2024, he moved from Vancouver to San Francisco. The timing was deliberate. Building a stealth cybersecurity startup requires proximity to the people and capital that make such things possible. He is now co-founder and CEO of that company - the specifics kept quiet for now, as is appropriate for anything still in formation.

What makes Ross unusual in the security world is not just the output volume - though it is considerable - but the cross-disciplinary range. He writes about product-led growth, angel investing, go-to-market strategy, industry dynamics, and founding psychology. He has been interviewed on Forgepoint Capital's Forgecast, the CISO Tradecraft podcast, Illumio's Segment podcast, Cyber GTM Talk, and a dozen others. Regular contributor to VentureBeat, Dark Reading, SC Media, and the World Economic Forum.

His published perspective on the current market is refreshingly direct: "There is no open opportunity in the market in 2025 and one has to go with what they know." That kind of honesty - which cuts against the relentless optimism typical of startup media - is exactly why people read him. He earned the audience by being accurate, not by being encouraging.

He describes himself as "super active on LinkedIn" and, almost as an afterthought, notes that his Twitter/X account exists but is essentially unused. This is a man whose primary medium is the long-form newsletter and the deep conversation - not the take machine. The newsletter's email engagement rate sits at 20-100 unique clicks per article, with LinkedIn shares driving 5K to 50K views. The archive runs to 70+ deep-dive posts.

The trajectory from history student to cybersecurity's most-read operator-analyst to stealth startup CEO reads like something a novelist would construct if they wanted it to feel implausible but earned. What is consistent across every phase of his career is the same instinct: find the thing that nobody has documented properly, and document it properly. The industry owes him a debt it mostly does not know it owes.