AI needs more uncertainty
AI has a confidence problem. Human intelligence was shaped by an uncertain world, and uncertainty is exactly the ingredient AI is missing.
The blog · since 2015
Insights for founders,
CTOs & investors.
Essays, playbooks and field notes from our CTOs, architects and leads. Written for people shipping real product.
Featured articles
What will the state of AI be like by this time next year?
Pricing strategies in the era of AI: why hourly billing no longer works
5 red flags for VCs when planning to invest in Seed or Series A companies
SaaS due diligence report: 12 learnings for founders that want to secure their next funding round
Things we do in our first weeks as Fractional CTO
Latest posts
AI needs more uncertainty
AI has a confidence problem. Human intelligence was shaped by an uncertain world, and uncertainty is exactly the ingredient AI is missing.
Your codebase is part of the prompt
Agents follow the patterns in the surrounding code more reliably than they follow your rules, so every inconsistent naming scheme and half-migrated architecture is a lesson you're teaching them. The fix isn't another rule file. It's deleting the bad example.
Three Codexes walk into a codebase: The return of the king
Two agents implemented and reviewed a full architecture refactor across five iterations, with zero lines of production code written by hand. What neither agent caught was four innocent lines in a coordinator that had quietly started making policy decisions.
The Claude desktop app just killed fifteen years of waiting for an Android emulator to boot
The Android emulator was never the real cost. The setup was: SDK paths, JDK versions, licence acceptance, a hand-edited config file, repeated on every machine and every new joiner. Claude Desktop takes that off your hands, and the wait that's left is spent reading a plan, not a stack trace.
Three Codexes walk into a codebase: The two agents
Codex got the same god class Claude had failed to remove, plus one thing Claude never had: a target architecture. An implementing agent and an independent reviewer then took three rounds to converge, because agents renovate around bad architecture rather than delete it.
A dial, not a switch: staging a risky migration with hash-bucket cohorts
A boolean feature flag starts a risky migration everywhere at once. Hashing a stable tenant ID into 100 buckets turns the flag into a dial that only ever widens, and the thresholds matter: percent-of-tenants is not percent-of-work.
Three Codexes walk into a codebase: The fellowship of the god class
Handing an AI your engineering conventions cleans up the code without fixing the architecture. A 5,000-line god class shrank to 500 lines across tidy domain files, and an independent reviewing agent still returned FAIL: authority never left the central object.
How to become an AI-native SaaS company in the next 3 years
Becoming AI-native in three years does not need a three-year technology roadmap. It needs a usage policy, a map of your data, one bounded experiment, and both the enthusiasts and the sceptics in the room. Build the ability to change, not the overhaul.
The architecture diagram is dead
Infrastructure documentation goes stale because it is a second thing to maintain. Terraform plus cloud discovery plus a few query tools describes the system better than any diagram, and leaves humans to document only the why behind the odd decisions.
AI chat is a brain in a jar
Hitting a wall with AI usually means hitting the wall of the chat box, not the wall of AI itself. Give a model memory, tool access and a browser, and the interfaces we built for humans become the integration. The bottleneck stops being the model and starts being your imagination.
When Sentry eats your transactions
Sentry silently drops transactions that blow past its span and payload limits, so the heaviest background jobs are exactly the ones missing from your dashboard. Capping span count and truncating span descriptions on bytes brings them back.
Your second brain knows more than you do
An AI-assisted note system captures faster than you can understand, and the gap compounds into internalisation debt: a dense graph of links attached to a thin mental model. The test of a knowledge base is not how much it holds, but how much you could still explain with the file closed.
How to choose a fractional CTO in Belgium: a guide for non-technical founders
A practical guide to evaluating fractional CTO providers in Belgium: the three criteria that matter most, how the four provider types differ, what an engagement should cost, and when a full-time hire is the better call.
The learning debt: what happens when delivery always wins over development
Teams accrue learning debt when shipping always beats getting better. It stays invisible on every dashboard, compounds fastest under AI-speed change, and quietly caps the ceiling a buyer is willing to price.
Curl says it's fast. Your users disagree.
Synthetic checks like curl and Lighthouse measure a request your users never make. A HAR file captures the real logged-in flow, and handed to Claude alongside the codebase it turns a wall of JSON into a ranked list of fixes that get implemented in the same conversation.
AI & agentic tooling
AI-first engineering
We use AI and agentic workflows daily. From coding agents to AI strategy, we help teams adopt what actually works.
Read our AI insightsEngineering leadership
CTO Insights
We <3 sharing content for CTOs, senior engineers and founders with real-world insights.
40+ expert authorsFor investors & VCs
Due diligence done right
Technical audits, codebase assessments, and risk analysis for portfolio managers making investment decisions.
Explore our investor content
How we help
Software engineering
Our staff engineers will get your software (back) on track and lead your engineering team. We prepare our exit from day one: our goal is to bring the software and the team to the right level for us to get out again.
Learn more about software engineeringCTO as a service
Our CTOs in residence (or fractional CTOs) inject technical leadership into your team, ensuring the technical aspect of your business gets exactly the right attention.
Learn more about CTO as a serviceAuditing
We're the market leader for technical due diligence of SaaS companies in Belgium and The Netherlands, servicing clients all over the world. Investors appreciate our smooth process, sharp opinions and top-notch reports.
Learn more about auditingCTO Coaching
Behind-the-scenes support for your CTO or technical lead to enhance their skills, drive effective change, and grow their teams confidently.
Learn more about CTO coachingRecruiting
We can help you find the best talent to join your team. Unlike other recruiters, we are CTOs and software engineers ourselves, and through getting our hands dirty, we know the skills required to make an impact.
Learn more about recruitingProduct management
Sometimes your struggles go beyond the technical. Do you need help evaluating the roadmap or sharpening the vision? What should you build in order to scale? Our product management experts know the way.
Learn more about product management