Essays

49 essays — long-form writing on technology, investing, and building from The Lossless Group.

AI is full of Hot Air.

From hallucinations to probabilistic creativity, to the need to fulfill its trained duty. AI Models can just make things up. Sometimes amazingly, sometimes catastrophically.

Avoid and Peril2026-05-23
Near-Future-Anticipation

Non-Developers will become Prototypers.

Vibe Coding gives more accessing to getting something working.

Near-Future-Anticipation2026-05-22
Near-Future-Anticipation

Software Development with Code Generators

Code generators are reshaping software development—speeding up delivery while raising new challenges.

Best Practices2026-05-22
State-Of-The-Art-PracticesVibe-Coding-PracticesNear-Future-Anticipation

Win The Market On Getting Started

The new way to get traction and win the market is to make it easy to get started.

Counterintuitive Approaches2026-05-14
Marketing-StrategiesState-Of-The-Art-PracticesExplainersExplorations+1

From Software Engineering To Managing Large Codebases

AI is already supporting individual engineers with particular tasks. How can it support large organizations with many teams and millions of lines of code?

Software-Engineering2026-05-04
Software-EngineeringSoftware-DevelopmentState-of-the-ArtCode-Generators+1

Technology wants to be Emergent

Emergent technology evolves unpredictably—shaping and reshaping our world in surprising ways.

Conceptual Frameworks2025-12-15
Technology-TrendsConceptual-Frameworks

The AI Model Wars

Mindbending sums of money and leadership panics all over the technolgoy world has set a frenzy of activity in the AI Model Wars.

Megatrend-Context2025-12-10
AI-ModelsModel-VendorsCloud-InfrastructureData-Centers+2

Someone's Gotta Keep Up with It

Keeping up with rapid tech change is a relentless challenge, but it’s the key to staying relevant.

Avoid and Peril2025-11-30
Near-Future-AnticipationManagement-StrategiesTechnology-Trends

Are Code Generators really the Death of SaaS?

At what point is building everything you can dream of cheaper than paying subscriptions?

Code-Generators2025-11-24
Near-Future-Anticipation

Embrace Pirates or See Mutiny

Organizations that embrace their renegade employees can spark innovation—or risk a mutiny.

Management-Strategies2025-11-24
Management-StrategiesWar-for-Talent

the-jaded-product-development-playbook

Counterintutive-Approaches2025-11-24
Product-Development-Pitfalls

The New Software Development Playbook

AI has changed how to develop software, and in many surprising ways.

2025-11-24
State-of-the-ArtContinuous-DeploymentContinuous-IntegrationContinuous-Refactoring+2

From Rags to Riches

Retrieval Augmented Generation transforms raw data into enterprise AI gold—if you set it up right.

Full-Body Commitments2025-11-16
Best-PracticesAI-Human-WorkflowAI-RAG-StackRetrieval-Augmented-Generation

On Data Gathering

Effective data gathering is the foundation for building intelligent, reliable AI systems.

Full-Body Commitments2025-11-16
Data-AugmentersData-CaptureData-WranglingData-APIs

A Theory of Lossless Innovation

To go forth and innovate while not losing the core business or loyalty of the current customer base is the challenge of our new era.

Conceptual Frameworks2025-11-11
Best-PracticesCollaboration-ToolingConceptual-Frameworks

Why Text Manipulation Is Now Mission Critical

AI models speak in text, JSON, and Markdown. Manipulation of these formats has become essential for productivity, automation, and insight.

Blind Spots2025-10-19
Abstract-Syntax-TreesNear-Future-AnticipationAdditional-ContextMarkdown+1

On the Need for Stack Engineering

Effective data gathering is the foundation for building intelligent, reliable AI systems.

Full-Body Commitments2025-09-27
JAM-Stack

Load up on CARBS

Align more people through vigilant visual communication.

Agile-Organizations2025-09-26
Management-StrategiesWar-for-TalentVisual-Communication

When to Partner with a Startup? When it's time for them to Scale Up

Timing is critical, because startups are not prepared to partner and scale ups will choose partners quickly.

Product-Development2025-09-25
Demand-GenerationMarketing-Automation

Opinionated Engineering

Opinionated engineering delivers clarity and speed—but can also spark debate.

Counterintutive-Approaches2025-09-24
Management-StrategiesDeveloper-ExperienceWar-for-TalentTalent-Development

The Geography of Innovation

Innovation may be global, but it still clusters in a few creative hotspots.

Near-Future-Anticipation2025-09-24
Conceptual-FrameworksNear-Future-Anticipation

Can Organizations Know what their People have Known?

Decades of data and experience are valuable, but how to bring them into the age of AI?

Knowledge-AI2025-09-23
Advanced-DocumentsKnowledge-AIKnowledge-BasesBusiness-Intelligence

Evolutions In Managing Large Codebases

While Vibe Coding is causing challenges as Software Developers use AI Code Assistants, AI is also showing to give engineering managers superpowers at managing large codebases.

Avoid and Peril2025-09-23

From Qualitative Love To Quantitative Love

Innovators can de-risk product and market development just by changing what they see as progress.

Best-Practices2025-09-23
Business-IntelligenceWeb-AnalyticsData-AnalyticsFounder-Toolkit

Open Source is now the Starting Line

Open source has become the ultimate catalyst for rapid innovation and zero-to-one breakthroughs.

Counterintutive-Approaches2025-09-23
Open-SourceOpen-Source-AlternativesDeveloper-ExperienceDeveloper-Tools

Tectonic Shifts and Business Configuration

Tectonic shifts in technology force businesses to reconfigure or risk being left behind.

Counterintutive-Approaches2025-09-23
Conceptual-FrameworksNear-Future-Anticipation

Holacracy-Inspired Reorganization

Holacracy-inspired reorgs promise agility, but require buy-in at every level to succeed.

Agile-Organizations2025-09-17
Management-StrategiesWar-for-Talent

We Need Better Charts

We have the opportunity to make data visualization as easy as the AI chatbot. Let's do it!

2025-09-17
Data-VisualizationsDiagrams-as-CodeCharts-as-Code

AI is first a Trojan Horse

A Taste of using AI effectively can be magical, but afterwards is a massive amount of reconfiguration and technology adoption.

Near-Future-Anticipation2025-09-15
Near-Future-Anticipation

The Multiverse Theory of Spatial Value Capture Dynamics in Innovation Markets

Innovation markets behave like a multiverse—value clusters, shifts, and leaps across invisible boundaries.

2025-09-15
Conceptual-Frameworks

Tiny Teams with Tiny Ideas

Small teams with focused ideas can spark outsized change.

Counterintuitive Approaches2025-09-15
Management-StrategiesProduct-DevelopmentBest-Practices

The Power of Challenges

Challenges ignite innovation—people rally around a cause, and breakthroughs follow.

Counterintutive-Approaches2025-09-05
Management-StrategiesState-Of-The-Art-PracticesBest-Practices

Timeline of Milestones in Technology

Technology’s history is a timeline of breakthroughs—each milestone reshapes what’s possible.

Tectonic Shifts2025-09-05
Additional-ContextExplorationsExplainers

Give them a Tool

The right tool at the right time can spark creativity and accelerate progress.

Agile-Organizations2025-08-22
Management-StrategiesTalent-Development

Why Vertical Wrappers Have Better Odds For Investors

2025-08-21

Web Security is about Preventing Naivety

Web security isn’t just about code—it’s about anticipating naivety at every layer.

Counterintuitive Approaches2025-08-20
ExplainersExplorationsWeb-SecurityPrivacy-Cloud

How Docker Changed Everything

Docker revolutionized software deployment by making containers the new standard for portability and scalability.

Tectonic-Shifts2025-07-28
Container-RuntimesDeveloper-ToolsDevOpsState-Of-The-Art-Practices

How GitHub Changed Everything

GitHub transformed how developers collaborate, making open source and distributed teamwork the global default.

Tectonic-Shifts2025-07-24
Continuous-IntegrationVersion-ControlCollaboration-ToolingCollaborative-Workflow+1

How Markdown Changed Everything

Markdown made digital writing simple, portable, and universally accessible—empowering everyone to publish.

Tectonic Shifts2025-07-19
JAM-StackOpen-SpecificationsContent-GenerationContent-Automation+1

How Rest APIs Changed Everything

REST APIs revolutionized digital integration, making it easy for apps and services to communicate everywhere.

Tectonic Shifts2025-07-19
API-StandardsState-Of-The-Art-Practices

Build Your Own PC

Building your own PC is the gateway to running powerful AI models locally, unlocking performance beyond cloud costs.

Counterintutive Approaches2025-07-08
Near-Future-AnticipationHome-Labs

Back to the Future

Old-school, textbook approaches are the secret to mastering the future of AI — sometimes, progress means going back to proven basics.

Best-Practices2025-06-05
Near-Future-AnticipationBest-PracticesConceptual-Frameworks

Consistent Go-to-Market

A disciplined, step-by-step approach is the key to derisking new product launches.

Product-Development2025-05-28
Demand-GenerationMarketing-Automation

Why Everyone needs to become a Linux User

Linux isn’t just for pros—everyone can benefit from its power, freedom, and flexibility.

Blind Spots2025-05-04
RecommendationsLinux-DistributionsState-Of-The-Art-Practices

Why User Research Repositories

User Research Repositories are an upfront investment for enormous gains over time.

Tools-of-the-Trade2025-05-04
User-ExperienceDesign-PracticesState-Of-The-Art-PracticesProduct-Development+1

The Irony of UI Stability

UI stability often wins over constant change — consistency keeps users loyal.

Counterintutive-Approaches2025-04-30
Software-DevelopmentDesign-PracticesUI-Design

The New New Founder Stack

The founder’s toolkit is evolving faster than ever—what’s essential today may be obsolete tomorrow.

Keeping-Up2025-04-30
ExplorationsCollaboration-Tooling

The Resurgence of the Terminal

The terminal is making a comeback — simplicity and power are winning over flashy GUIs.

Counterintutive-Approaches2025-04-30
Technology-TrendsState-Of-The-Art-PracticesDeveloper-ExperienceProductivity

How Kubernetes Changed Everything

Kubernetes made cloud-native infrastructure scalable, resilient, and automated for everyone.

Tectonic Shifts2025-04-28
Cloud-InfrastructureOpsless-DeployDeployment