I'm Richard Halldearn. I spent a decade building trading systems and market risk platforms at Morgan Stanley, Deutsche Bank, and Credit Suisse before leading PE-backed technology companies as CTO and CEO. Now I advise PE firms and portfolio company boards on technology strategy, M&A due diligence, and AI implementation.
I still write production Rust, build AI agents, and run my own infrastructure. That combination means I find things other advisors miss.
I work at the intersection of technology, investment, and operations. Every engagement is grounded in hands-on technical depth.
When you're evaluating an acquisition, I go deeper than most tech DD providers. I read the code. I review the architecture. I assess the engineering team's capabilities firsthand. I quantify technical debt in terms that map to your value creation plan. My reports include specific, costed remediation roadmaps — not just traffic-light risk matrices.
Most AI strategies presented to PE boards are aspirational at best. I help portfolio companies develop AI roadmaps grounded in what actually works — because I build AI systems myself. From LLM integration to agent architectures to prompt engineering, I bring hands-on experience to strategic decisions.
Some portfolio companies need a technology perspective at the board level but aren't ready for a full-time CTO hire. I provide ongoing advisory, attend board meetings, review technology strategy, and ensure the engineering team is aligned with the business plan.
I started my career building trading systems and market risk platforms at Morgan Stanley, Deutsche Bank, and Credit Suisse. That decade in Tier 1 investment banking taught me what it means to build mission-critical systems — where latency matters, regulatory requirements are non-negotiable, and architecture decisions have real financial consequences. I then led PE-backed technology companies as CTO and CEO, navigating turnarounds, global enterprise sales, and the full M&A lifecycle from every seat at the table.
I studied Computer Science at Imperial College London — where my dissertation applied machine learning to endurance training analysis — and have published research on Google Scholar. But what actually sets me apart is simpler than credentials: I still build things. I write production Rust. I build and deploy AI agents. I run my own mail server and infrastructure.
When I assess a company's technology during due diligence, I can read the code, evaluate the architecture, and talk to the engineers in their own language. Having built trading platforms under regulatory pressure and scaled SaaS products through acquisitions, I know what good looks like — and I know what "good enough for a slide deck" looks like.
A decade building trading systems and market risk platforms at Morgan Stanley, Deutsche Bank, and Credit Suisse. I know what mission-critical means.
Experience as target company exec, integration lead, and PE advisor. I understand every side of the deal.
Production Rust, AI agents, infrastructure. I still write code and ship systems — not just slide decks.
Every engagement is different, but most fall into one of these patterns.
Deep technical assessment of a target company's technology, architecture, team, and technical debt. Deliverable is a detailed report with costed remediation roadmap, aligned to your investment thesis and value creation plan.
Post-acquisition technology strategy and execution support. I work with portfolio company leadership to build AI roadmaps, modernise platforms, and align engineering efforts with financial goals like ARR and EBITDA growth.
Board-level technology perspective on an ongoing basis. I attend board meetings, review strategy, assess engineering capability, and provide the technical lens that many PE-backed boards are missing.
I write about what I build and what I learn. These posts are the best proof of how I think about technology.
Why I see email as the secure front door for AI agents, and how wiring Mailbuttons into OpenClaw lets me automate everything behind that inbox.
My journey creating AI agents for email processing. The proofreader agent worked flawlessly, while the games agent taught me hard lessons about prompt engineering and state management.
Setting up an email server reveals the harsh reality of internet security. Within hours of opening the firewall, automated scanners were already probing for vulnerabilities.
Whether you have a deal in diligence, a portfolio company that needs technology direction, or a question about AI strategy — I'm happy to have a conversation.
4 Plough Yard, London, EC2A 3LP
Unit 96 The Maltings Business Centre, Stanstead Abbotts, Ware, Herts, England, SG12 8HG