Risk-First: Stars of Software

Dave Thomas: Pragmatism, Feedback Loops, and Why AI Doesn’t Change the Fundamentals

In this episode of Risk-First: Stars of Software, Rob Moffat talks with Dave Thomas, co-author of The Pragmatic Programmer, original signatory of the Agile Manifesto, founder of The Pragmatic Bookshelf, and long-time thinker on software simplicity, agility, and feedback-driven development. 

Dave has spent decades shaping how software developers think about programming — from pragmatism and feedback loops, through Agile, Ruby, and testing, to his more recent work on simplicity and AI-assisted software development.

Along the way, Rob and Dave dive into:

• Why nearly every idea in The Pragmatic Programmer still applies in the age of AI 
• The role of feedback loops in software development
• Why Agile was originally about values and adaptability
• The origins of the Agile Manifesto and how it unexpectedly “went viral” after Snowbird
• How military concepts like “commander’s intent” parallel modern agile software teams
• Why organisations built around top-down command structures struggle to be genuinely adaptive
• How delighting users requires empathy, not just technical competence
• Why empathy matters not only for people, but for machines, systems, and software design itself
• The possibility that future AI-generated software may eventually become unreadable to humans
• Why AI may ultimately reinforce good software design practices like small modules, meaningful names, and readable structure
• The ongoing “CVE apocalypse”
• Why writing books — and software — is fundamentally about synthesising and refining ideas from reality into reusable forms
• Dave’s belief that the best way to navigate an increasingly complex world is to live “agilely”: taking small reversible steps guided by feedback

The Pragmatic Programmer
https://pragprog.com/titles/tpp20/the-pragmatic-programmer-20th-anniversary-edition/
Classic software engineering book introducing concepts like pragmatism, tracer bullets, orthogonality, and feedback-driven development.

The Pragmatic Bookshelf
https://pragprog.com
Technical publishing company focused on practical software development books across programming, AI, testing, and engineering.

Agile Manifesto
https://agilemanifesto.org
The original Agile Manifesto and principles created at Snowbird in 2001.

Simplicity
https://pragprog.com/titles/dtlang/simplicity/
Dave Thomas’ recent book exploring simplicity, empathy, systems thinking, and software design.

FINOS
https://www.finos.org
Open source foundation discussed in relation to software supply chain security and open source sustainability.

Dave Thomas’ Substack
https://newsletter.pragmaticengineer.com
Dave’s writing and commentary on software, AI, and programming ideas.

James McLeod: Open Source Communities, Hackathons, and Why Open Source Opens Doors

In this episode of Risk-First: Stars of Software, Rob Moffat talks with James McLeod, Open Source Lead at NatWest Group, FINOS board member, and organiser of London JS. 

James has spent years at the intersection of enterprise technology and grassroots developer communities — helping banks engage with open source while also building one of London’s best-known JavaScript meetups. Before NatWest, he worked directly within FINOS helping financial institutions collaborate through open source, standards, and shared engineering practices.

The conversation explores how open source communities form around uncertainty, why meetups and hackathons matter far more than most organisations realise, and how the current explosion of AI tooling mirrors the chaos and creativity of the early JavaScript ecosystem.

Along the way, Rob and James dive into:

• How the rise of React, Node.js, npm, and frontend frameworks created a “primordial soup” developers had to collectively figure out together 
• Why London JS was created to help developers learn collaboratively rather than depend on individual experts 
• The importance of creating communities where people can safely experiment, fail, and learn in public 
• Why meetups act as “distilled serendipity” — compressing useful collisions between people and ideas
• How open source communities help reduce dependency on proprietary ecosystems and centralized knowledge
• Why hackathons are valuable not just for innovation, but for exposing firms to external thinking and new technologies 
• The challenge of maintaining momentum after hackathons end and preventing ideas from “rotting in a repo” 
• How open source participation helps organisations avoid becoming technologically entrenched 
• Why enterprises often misunderstand open source as purely an IP issue instead of a collaborative engineering model 
• James’ experiences moving from highly proprietary Microsoft ecosystems into open source development cultures 
• How AI today feels similar to the early React ecosystem: lots of tools, rapid change, and nobody really knowing the “correct” answers yet 
• Why AI communities need openness, shared learning, and emotional intelligence — especially when many developers are anxious about the future of work 
• The idea that “open source opens doors” — creating careers, friendships, startups, and opportunities far beyond code itself

London JS
https://www.meetup.com/london-js/
London-based JavaScript and frontend development community bringing together developers, speakers, and technology enthusiasts.

FINOS (Fintech Open Source Foundation)
https://www.finos.org
Foundation enabling collaboration on open source projects and standards across financial services.

NatWest Group
https://www.natwestgroup.com
UK banking group active in open source collaboration and FINOS initiatives.

Viktor Petersson: SBOMs, Supply Chains, and the Reality of Software Transparency

In this episode of Risk-First: Stars of Software, Rob Moffat talks with Viktor Petersson, founder of SBOMify and co-founder and CEO of Screenly.

Viktor has spent years building real-world systems at the intersection of hardware, cloud, and security—from early Raspberry Pi-based digital signage through to globally deployed platforms used by organisations like NASA and Capital One. More recently, he’s focused on one of the most talked-about—and misunderstood—areas in modern software: Software Bills of Materials (SBOMs).

The conversation explores why SBOMs have suddenly become a regulatory and industry focus, whether they actually solve the problems they claim to, and what it really means to understand what’s inside the software we run.

Along the way, Rob and Viktor dive into:

• What an SBOM actually is—and why it’s often misunderstood as just “a file”
• Why software supply chain transparency is much harder than it sounds
• The gap between regulatory intent and engineering reality
• Why generating SBOMs is easy—but making them useful is not
• The problem of incomplete, inaccurate, or outdated dependency data
• How transitive dependencies create hidden and compounding risk
• Why most organisations don’t actually know what’s in their software
• The difference between compliance-driven SBOMs and operationally useful ones
• Why “perfect visibility” is probably unattainable—and what to do instead
• How SBOMs intersect with vulnerability management and incident response
• The role of tooling, automation, and standards in making SBOMs usable
• Whether SBOMs reduce risk—or just make it more visible
• How supply chain security is evolving alongside AI-generated code

sbomify
https://sbomify.com
Platform focused on generating, managing, and operationalising Software Bills of Materials.

Screenly
https://www.screenly.io
Digital signage platform originally built on Raspberry Pi, now deployed globally across enterprise environments.

Software Bill of Materials (SBOM)
A structured representation of the components, libraries, and dependencies that make up a piece of software.

Software Supply Chain Risk
Risks arising from dependencies on external code, including vulnerabilities, maintainership gaps, and compromised packages.

Transitive Dependencies
Dependencies of dependencies, which often introduce hidden complexity and risk.

SBOM Accuracy & Freshness Problem
The challenge of keeping SBOMs up to date and reflective of real-world deployed systems.

Compliance vs Operational Security
The difference between producing artefacts to satisfy regulators and actually improving security posture.

Vulnerability Management Integration
Using SBOMs as input into processes that identify, prioritise, and remediate security vulnerabilities.

AI-Generated Code Risk
The increasing difficulty of understanding software composition as AI accelerates code generation and reuse.

Jyoti Wadhwa: AI Governance at Scale, Decision Risk, and the Future of the SDLC

In this episode of Risk-First: Stars of Software, Rob Moffat talks with Jyoti Wadhwa, global leader in AI governance and enterprise technology risk, and contributor to FINOS AI governance efforts.

Jyoti has spent her career helping large organisations—from Fortune 100 companies to US federal agencies—adopt emerging technologies safely, translating regulatory expectations, risk frameworks, and responsible AI principles into governance models that actually work in practice. Which makes her the perfect person to explore what governance really means when you’re operating at scale.

The conversation explores how organisations move from individual experimentation with AI tools to coordinated, enterprise-wide adoption, why governance isn’t about slowing things down but enabling decisions, and how the shift to agentic, non-deterministic systems is fundamentally changing the software development lifecycle.

Along the way, Rob and Jyoti dive into:

• Why governance is really about decision-making at scale—not documentation
• The concept of decision risk as the most important risk in AI adoption
• How organisations must bring the right stakeholders together based on use case, not hierarchy
• Why governance enables innovation rather than slowing it down
• The three major AI risk buckets: regulatory/compliance, data & privacy, and operational visibility
• How policies translate from law → organisational agreement → technical controls
• Why the SDLC is shifting from deterministic pipelines to probabilistic, agent-driven systems
• The challenge of maintaining control and auditability in AI-driven development
• Why “human in the loop” systems must account for psychological limits like vigilance decrement
• The emergence of baseline architectures and reference models for safe AI adoption
• Why inconsistent LLM usage across business units is already a real-world governance failure
• How FINOS and industry standards help create shared “baselines of good” across firms
• Why vendor risk and AI tooling sprawl are becoming major enterprise concerns
• How regulation will continue to lag innovation—but increase rapidly in response

## Links

FINOS AI Governance Framework
https://github.com/finos/ai-governance-framework
Open-source framework defining risks and controls for adopting AI in financial services.

FINOS (Fintech Open Source Foundation)
https://www.finos.org
Industry foundation enabling collaboration on open standards and governance across financial services.

NIST AI Risk Management Framework
https://www.nist.gov/itl/ai-risk-management-framework
Widely referenced framework for managing AI risk, governance, and trustworthy AI systems.

MITRE ATT&CK Framework
https://attack.mitre.org
Knowledge base of adversary tactics and techniques used for threat modelling and security analysis.

Brittany Istenes: Open Source Readiness, OSPOs, and Why Contribution Is Risk Management

In this episode of Risk-First: Stars of Software, Rob Moffat talks with Brittany Istenes, open source strategist, InnerSource advocate, and contributor to FINOS’ Open Source Readiness work.

Brittany has spent years helping large organisations—especially in regulated industries—figure out how to actually work with open source, not just consume it. Which makes her the perfect person to explore one of the biggest blind spots in enterprise technology today: the gap between relying on open source and understanding how to manage the risks that come with it.

The conversation explores why so many firms depend on open source but struggle to engage with it properly, what OSPOs are really for (beyond compliance), and how organisations can move from passive consumption to active participation without losing control.

Along the way, Rob and Brittany dive into:

• Why open source is effectively critical infrastructure—but isn’t treated or funded like it
• The reality of “OSPOs of one” and why most firms underestimate their importance
• How dependency risk, licensing, and supply chain issues create hidden exposure in large organisations
• Why contributing upstream isn’t altruism—it’s a way to reduce risk and gain influence
• How InnerSource helps organisations learn open collaboration safely before engaging externally
• The role of foundations like FINOS in creating trusted environments for collaboration between competitors
• Why the cost of internal forks is often invisible—but significant
• How AI and “vibe coding” could massively increase the volume of open source (and the associated risks)

FINOS Open Source Readiness (OSR)
https://osr.finos.org

InnerSource Commons
https://innersourcecommons.org

FINOS (Fintech Open Source Foundation)
https://www.finos.org

Music Mentioned Includes:

• Oranssi Pazuzu (Finnish black metal)
• Nine Inch Nails – With Teeth
• MF DOOM – Doomsday
• Tom Waits
• The Bobby Lees
• Blackwater Holylight
• Wu-Tang Clan
• Puscifer
• Tool
• Tron: Legacy (Daft Punk soundtrack)
• The Crow (1994 soundtrack)

Colin Eberhardt: AI Governance, Agentic Coding, and the Future of Open Source

In this episode of Risk-First: Stars of Software, Rob Moffat talks with Colin Eberhardt, CTO of Scott Logic, long-time FINOS contributor, and one of the principal authors of the AI Governance Framework.

Colin has spent years helping financial institutions adopt new technologies safely—without slowing innovation to a crawl. Which makes him exactly the right person to talk to about the biggest technological shift the software industry has seen in decades: AI.

The conversation explores what AI governance actually looks like in practice, why banks struggled to work out whose problem AI even was, and how large organisations can adopt powerful new tools without accidentally causing chaos.

Along the way, Rob and Colin dive into:

• Why AI governance isn’t about bureaucracy, but about helping organisations understand risks they didn’t even know they had
• How non-deterministic systems break many traditional software engineering techniques
• Why testing and feedback loops may become the most important tools in AI-driven development
• The rise of agentic coding loops that can autonomously iterate until tests pass
• How AI could radically change legacy system migration, software delivery, and developer productivity
• Whether AI will flood the world with open-source projects… or quietly make open source less necessary

• Scott Logic
  https://www.scottlogic.com
  UK-based software consultancy focused on complex platforms, trading systems, and large-scale engineering challenges.
• FINOS AI Governance Framework
  https://github.com/finos/ai-governance-framework
  Open-source framework describing risks and mitigations when adopting generative AI in financial services.

• AI Augmented Coding Weekly — Colin’s newsletter
  https://newsletter.scottlogic.com
  Commentary and analysis on how AI is changing software engineering practices.
• The AI Daily Brief podcast
  https://podcasts.apple.com/us/podcast/the-ai-daily-brief/id1669813433
  Regular updates on AI developments, industry trends, and major model releases.

• Claude Code / Anthropic tools
  https://www.anthropic.com
  AI coding agents and autonomous development workflows.
• Next.js
  https://nextjs.org
  Popular React framework used as an example of modern web infrastructure and AI-assisted cloning.
• Ladybird browser project
  https://ladybird.dev
  Experimental open-source browser engine referenced during discussion of AI-assisted codebase recreation.

In this episode of Risk-First: Stars of Software, Rob Moffat speaks with Kunal Kushwaha—Senior Developer Advocate at CAST AI, founder of the global WeMakeDevs community, CNCF Ambassador, and one of the most recognisable voices in today’s cloud-native ecosystem.

Kunal’s work sits at the intersection of cloud infrastructure, developer education, and community-driven learning, focused on helping organisations reduce cloud waste, improve reliability and performance, and navigate the growing complexity of Kubernetes and AI-driven platforms. At its core, his perspective highlights that risk in modern technology is not just technical—it’s human, organisational, and economic. 

Together, Rob and Kunal explore:

• Why cloud complexity and over-provisioning create hidden financial and reliability risks
• How developer relations connects human relationships to business outcomes
• Lessons from building data-centre infrastructure and global developer communities early in a career
• Real-world failures—from data-centre fires to open-source contribution overload—and what they teach about resilience
• How open source, AI agents, and autonomous cloud platforms are reshaping the future of software
• Why success in technology still depends on focus, learning-by-doing, and strong human networks

• CAST AI
  https://cast.ai
  Autonomous cloud optimisation platform focused on performance, reliability, and cost efficiency.
• WeMakeDevs community
  https://wemakedevs.org
  Global developer community running hackathons, events, and learning programmes across 20+ countries.

• Tech With Nana (YouTube)
  https://www.youtube.com/c/TechWorldwithNana
  Clear, practical explanations of cloud-native and DevOps concepts.
• TLDR Newsletter
  https://tldr.tech
  Daily curated updates across software engineering, AI, and startups.
• Hacker News
  https://news.ycombinator.com
  Community-driven discussion of technical trends and projects.
• Product Hunt
  https://www.producthunt.com
  Discovery platform for new developer tools and technology products.
• Kubernetes Blog
  https://kubernetes.io/blog
  Official updates and deep dives from the Kubernetes ecosystem.

• Stuff You Should Know
  https://www.iheart.com/podcast/105-stuff-you-should-know-26940277/
  Broad, curiosity-driven explorations of everyday topics.
• Science Vs
  https://gimletmedia.com/shows/science-vs
  Evidence-based deep dives into popular claims, including AI and technology.

Episode 2 — Steve Tendon: Constraints, Flow, and the Human Side of Organisational Risk

In this episode of Risk-First: Stars of Software, Rob Moffat speaks with Steve Tendon—creator of the Tameflow approach and a leading thinker in systems thinking, organisational performance, and flow-based management.

Steve’s work sits at the intersection of theory and real-world change, helping organisations improve economic, operational, organisational, and human performance by focusing on constraints, decision-making, and the social dynamics of collaboration. At its core, Tameflow is about understanding how people communicate, make trade-offs, and ultimately manage risk—whether explicitly or by intuition. 

bobmkite9s-studio_risk-first-st…

Together, Rob and Steve explore:

• Why organisational success depends on decision-making and trade-offs, not just process
• How the Theory of Constraints applies to knowledge work and software systems
• The hidden risks in mergers, acquisitions, and organisational culture clashes
• Why certifications signal capability—but real expertise requires evidence and outcomes
• The importance of feedback loops, systems thinking, and human collaboration in avoiding failure
• What it means to “think more differently” in a rapidly changing, AI-shaped future

From last-minute product disasters caught minutes before release to breakthrough organisational turnarounds, this conversation reveals a powerful theme: performance improves when we focus on what truly constrains us—and have the courage to change how we think.

If risk is about navigating uncertainty and trade-offs, then mastering flow, constraints, and human decision-making may be the most important skill of all.

https://www.amazon.co.uk/dp/0884271951
A classic introduction to the Theory of Constraints, presented as a narrative about improving organisational performance. Steve highlights it as a book worth rereading many times because new insights emerge with each pass.

https://www.goldratt.com/resources/books
Further exploration of constraints thinking, flow, and systemic improvement across organisations and industries.

https://patternlanguage.com
Foundational ideas behind patterns, organisational design, and systems thinking, which strongly influence the Tameflow approach.

https://tameflow.com
Steve’s organisational performance and systems-thinking consultancy focused on improving economic, operational, organisational, and human flow.

https://tameflow.com/circle
A discussion community exploring systems thinking, constraints, organisational design, and knowledge-work performance.

https://tameflow.com/career-booster
Steve’s programme aimed at helping individuals improve professional effectiveness using constraints thinking, conflict resolution, and systemic decision-making.

Episode 1 — Dom Vogel: Cybersecurity, Leadership, and the Risks We Choose Not to See

In the very first episode of Risk-First: Stars of Software, Rob Moffat sits down with cybersecurity leader Dom Vogel to explore what risk really means beyond code, tools, and technology.

With more than two decades in the field, Dom shares how cybersecurity has evolved from a niche IT concern into a core business risk—and why many executives still fail to see it that way. From boards of directors who only pay attention when their yachts are on the line, to companies brought to a halt by ransomware because no one ever tested their backups, this conversation reveals a simple truth: most disasters aren’t sophisticated—they’re preventable. 

bobmkite9s-studio_risk-first-st…

Together, Rob and Dom unpack:

• Why cybersecurity must be owned by business leaders, not just IT
• How poor governance—not missing technology—causes most breaches
• The hidden risks of dependency on digital systems and “shadow AI”
• Why networking and human skills matter more than technical brilliance in security careers
• How AI could transform security from burnout-driven alert chasing into meaningful risk management

This episode sets the tone for the series: understanding that success in technology—and perhaps any profession—comes down to making better decisions about risk.

If you want to get better at what you do, start by understanding the risks that shape it.

• Dark Reading
  https://www.darkreading.com
  Focuses on current security threats, research, and trends with strong links back to business impact.
• CSO Online
  https://www.csoonline.com
  Covers security leadership, governance, and risk from an executive and organisational perspective.

• Bruce Schneier’s blog (Schneier on Security)
  https://www.schneier.com
  Long-running, highly respected commentary on security, privacy, and real-world risk.

• LinkedIn – easiest place to connect and follow his daily “stories from the trenches”
  https://www.linkedin.com
• Vogel Security Leadership & Training
  https://vogelleadershipcoaching.com