Essays

50 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 Peril 2026-05-07
Near-Future-Anticipation

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-Engineering 2026-05-04
Software-Engineering Software-Development State-of-the-Art Code-Generators +1

Software Development with Code Generators

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

Best Practices 2025-12-27
State-Of-The-Art-Practices Vibe-Coding-Practices Near-Future-Anticipation

Technology wants to be Emergent

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

Conceptual Frameworks 2025-12-15
Technology-Trends Conceptual-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-Context 2025-12-10
AI-Models Model-Vendors Cloud-Infrastructure Data-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 Peril 2025-11-30
Near-Future-Anticipation Management-Strategies Technology-Trends

Are Code Generators really the Death of SaaS?

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

Code-Generators 2025-11-24
Near-Future-Anticipation

Embrace Pirates or See Mutiny

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

Management-Strategies 2025-11-24
Management-Strategies War-for-Talent

Non-Developers will become Prototypers.

Vibe Coding gives more accessing to getting something working.

Near-Future-Anticipation 2025-11-24
Near-Future-Anticipation

the-jaded-product-development-playbook

Counterintutive-Approaches 2025-11-24
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-Art Continuous-Deployment Continuous-Integration Continuous-Refactoring +2

From Rags to Riches

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

Full-Body Commitments 2025-11-16
Best-Practices AI-Human-Workflow AI-RAG-Stack Retrieval-Augmented-Generation

On Data Gathering

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

Full-Body Commitments 2025-11-16
Data-Augmenters Data-Capture Data-Wrangling Data-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 Frameworks 2025-11-11
Best-Practices Collaboration-Tooling Conceptual-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 Spots 2025-10-19
Abstract-Syntax-Trees Near-Future-Anticipation Additional-Context Markdown +1

On the Need for Stack Engineering

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

Full-Body Commitments 2025-09-27
JAM-Stack

Load up on CARBS

Align more people through vigilant visual communication.

Agile-Organizations 2025-09-26
Management-Strategies War-for-Talent Visual-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-Development 2025-09-25
Demand-Generation Marketing-Automation

Opinionated Engineering

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

Counterintutive-Approaches 2025-09-24
Management-Strategies Developer-Experience War-for-Talent Talent-Development

The Geography of Innovation

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

Near-Future-Anticipation 2025-09-24
Conceptual-Frameworks Near-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-AI 2025-09-23
Advanced-Documents Knowledge-AI Knowledge-Bases Business-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 Peril 2025-09-23

From Qualitative Love To Quantitative Love

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

Best-Practices 2025-09-23
Business-Intelligence Web-Analytics Data-Analytics Founder-Toolkit

Open Source is now the Starting Line

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

Counterintutive-Approaches 2025-09-23
Open-Source Open-Source-Alternatives Developer-Experience Developer-Tools

Tectonic Shifts and Business Configuration

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

Counterintutive-Approaches 2025-09-23
Conceptual-Frameworks Near-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 Approaches 2025-09-23
Marketing-Strategies State-Of-The-Art-Practices Explainers Explorations +1

Holacracy-Inspired Reorganization

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

Agile-Organizations 2025-09-17
Management-Strategies War-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-Visualizations Diagrams-as-Code Charts-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-Anticipation 2025-09-15
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 Approaches 2025-09-15
Management-Strategies Product-Development Best-Practices

The Power of Challenges

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

Counterintutive-Approaches 2025-09-05
Management-Strategies State-Of-The-Art-Practices Best-Practices

Timeline of Milestones in Technology

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

Tectonic Shifts 2025-09-05
Additional-Context Explorations Explainers

A New API Standard for chaining AI -- Model Context Protocol

Chain and sequence AI operations with Model Context Protocol, a game-changer for AI use and code generation.

AI-Workflows 2025-08-28
Model-Context-Protocols AI-Workflows Code-Generators Agentic-AI +1

Give them a Tool

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

Agile-Organizations 2025-08-22
Management-Strategies Talent-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 Approaches 2025-08-20
Explainers Explorations Web-Security Privacy-Cloud

How Docker Changed Everything

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

Tectonic-Shifts 2025-07-28
Container-Runtimes Developer-Tools DevOps State-Of-The-Art-Practices

How GitHub Changed Everything

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

Tectonic-Shifts 2025-07-24
Continuous-Integration Version-Control Collaboration-Tooling Collaborative-Workflow +1

How Markdown Changed Everything

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

Tectonic Shifts 2025-07-19
JAM-Stack Open-Specifications Content-Generation Content-Automation +1

How Rest APIs Changed Everything

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

Tectonic Shifts 2025-07-19
API-Standards State-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 Approaches 2025-07-08
Near-Future-Anticipation Home-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-Practices 2025-06-05
Near-Future-Anticipation Best-Practices Conceptual-Frameworks

Consistent Go-to-Market

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

Product-Development 2025-05-28
Demand-Generation Marketing-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 Spots 2025-05-04
Recommendations Linux-Distributions State-Of-The-Art-Practices

Why User Research Repositories

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

Tools-of-the-Trade 2025-05-04
User-Experience Design-Practices State-Of-The-Art-Practices Product-Development +1

The Irony of UI Stability

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

Counterintutive-Approaches 2025-04-30
Software-Development Design-Practices UI-Design

The New New Founder Stack

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

Keeping-Up 2025-04-30
Explorations Collaboration-Tooling

The Resurgence of the Terminal

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

Counterintutive-Approaches 2025-04-30
Technology-Trends State-Of-The-Art-Practices Developer-Experience Productivity

How Kubernetes Changed Everything

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

Tectonic Shifts 2025-04-28
Cloud-Infrastructure Opsless-Deploy Deployment