I'm Richard Halldearn. I advise PE firms and portfolio company boards on technology strategy, M&A due diligence, and AI implementation.
I also 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've spent 15+ years as CEO and CTO of PE-backed technology companies. I've been the target company executive during acquisitions, led post-deal integration, and now advise PE firms on the other side of the table. That full-lifecycle M&A experience means I understand what matters from every angle.
I studied at Imperial College London 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. When I advise on AI strategy, it's grounded in what I've built myself — not what I've read in a vendor pitch deck.
15+ years as CEO and CTO of PE-backed companies, directing technology strategy and multi-million pound initiatives.
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