Entry 15 - Askara Year One: A Full Circle Review
Hey there,
As 2025 closes, I find myself looking back at a year that started with a simple idea and ended with something far more substantial than I could have imagined. What began as Certaify, a concept for automating cybersecurity compliance, has transformed into Askara: a team, a methodology, a vision for how AI can genuinely serve organisations.
This entry is my attempt to honour that journey. To show gratitude for what worked, learn from what didn't, and extract the lessons that will shape 2026.
The Return
The most satisfying moment of the year came in my final week working with our first client. We had finally deployed the agentic AI automations that started this whole adventure: handling cybersecurity incidents, reading audit reports, tracking awareness training. Simple workflows, but exactly what I'd envisioned when I first sketched out Certaify over a year ago.
Watching the staff interact with these systems gave me goosebumps. Not because the technology was flashy, but because it worked. People were using it. It solved real problems. That moment of product market validation is something every entrepreneur dreams about, and experiencing it felt genuinely magical.
The irony is that these automations could have been built much sooner if we'd focused purely on product. But that would have missed the point entirely. The year wasn't just about building software. It was about building everything else that makes software meaningful: a team that trusts each other, a methodology that actually works, a vision worth pursuing.
Along the way, we developed something I hadn't anticipated: a novel approach to risk management with AI at its core. We came to understand that risk is the discipline most cybersecurity standards hinge on. This insight now sits at the centre of everything we're building.
The Foundations
What surprised me most was how much foundational work the year demanded. We shaped our WHY and formalised our commitment through Slicing Pie methodology. We grew the team and, through our retreat in Tallinn, merged into something that feels like a genuine unit. We embraced a phrase that's become central to how we operate: "Extraordinary trust fuels extraordinary results."
We established rhythms at every scale: yearly, quarterly, monthly, weekly. Finding that balance between synchronicity and structure took real effort, but now it feels natural. The Shape Up cycles aligned with seasons. The check-ins that respect deep work. The retrospectives that actually teach us something.
The Cyber Accelerator deserves special mention. It didn't just provide funding. It created the space to refocus on our core idea after months of necessary experimentation with different services and products. Some of that experimentation was about finding revenue for financial feasibility. But the accelerator freed us to come full circle and deliver what we'd set out to build from the beginning.
That freedom also reshaped how we think about growth. Rather than pursuing venture capital with its pressure for rapid scaling, we've leaned into the European subsidy ecosystem. This approach lets us build without compromising on quality or autonomy.
The Edge
Not everything received the attention it deserved.
Content creation and marketing fell behind. Software and content are the two pillars of IP and knowledge leverage in our age, as Naval Ravikant teaches. From the very beginning of my freelancing journey, I've aspired to develop these skills. Behind the scenes we've been crafting and experimenting, but nothing substantial has seen the light of day yet.
This matters because you can never start early enough building an audience. It's the one area where I feel genuinely snowed under from the transition between freelance life and startup building. But with Andrew now leading such a strong software development team, I can finally shift more attention to content development in the coming year.
The Trade Mission to Toulouse opened strategic terrain I hadn't fully anticipated. Exploring the defence sector as a direction for partnerships left a lasting imprint. Trust sits at the core of everything we do with Askara, and profiling our product as "military grade software" aligns perfectly with that.
Whether we actually penetrate the defence market remains to be seen. But the exploration clarified something important: we need to start immediately on industry standards and norms that demonstrate trustworthiness. ISO9001 lies at the foundation of many of these certifications. So we'll pursue it straight away in 2026, practising what we preach as a compliance automation company. Over the years, we'll collect the strategic certificates that radiate trust to the business world.
For 2026, we've applied to two additional cybersecurity innovation funds, creating budget for both backend and frontend innovation. Building the network to play this European game has been its own reward. Participating in EU events with Reinier reminded me of my student days with IAESTE and the international conferences that were highlights of that time. There's a playful attitude we're rediscovering: the recognition that all aspects of work can become play when approached with the right spirit.
The Harvest
Looking back, I can identify clear peaks and valleys:
Biggest Win: The Cyber Accelerator programme. It created the conditions to refocus and deliver on our original vision by year's end.
Biggest Miss: Content creation and marketing. The audience building we should have started months ago.
Biggest Mindset Shift: Moving from pursuing client revenue to stay bootstrapped, toward non-diluting subsidies. Learning to play the European game.
Top Three Highlights:
What strikes me most is how the original spark, that simple idea for compliance automation, had to travel through so much transformation before it could land properly. The detours weren't distractions. They were the work of building something that could actually hold the vision.
2026 begins with foundations in place that didn't exist a year ago. A team operating with genuine trust. A methodology that balances structure with flow. A product that people actually use. And a strategic direction that lets us build on our own terms.
Full circle, but at a higher altitude.
With care,
Ben