Regular Expressions

For years, the golden rule of software development was to launch a "Minimum Viable Product" (MVP). This usually meant shipping something stripped down, unpolished, and barely functional just to test the market. But now that AI can generate functional code in seconds, the old rules of the MVP are changing. In this episode, Ben Griswold (Grizen) and Noah Heldman (OutcomeSource) sit down with product...

Anthropic recently launched its highly anticipated flagship model, Fable 5, boasting massive leaps in reasoning, agentic coding, and cybersecurity. But what should have been a triumphant pre-IPO release quickly devolved into a bizarre political soap opera. After Anthropic leadership publicly warned that their own advancements were becoming dangerous, the US government stepped in with heavy restric...

AI has already written an estimated 1.5 to 2 trillion lines of code, representing roughly 15% of all code in existence today. With platforms like GitHub feeling the strain of this massive output, developers are starting to question the long-term quality and security of an ecosystem increasingly built by machines. In this episode, Ben Griswold (Grizen) and Noah Heldman (OutcomeSource) examine the s...

Long before generative AI agents were writing code, platforms like Topcoder were using crowdsourcing to solve massive technical problems. It turns out that breaking down complex projects for a distributed network of human developers was the perfect training ground for how we interact with AI today. In this episode, Ben Griswold (Grizen) and Noah Heldman (OutcomeSource) welcome technology executive...

The tools we use to write software are evolving at breakneck speed. Cursor recently dropped version 3 featuring a brand new agent-first interface, while Anthropic continues to push developers toward the terminal with Claude Code. But are these new autonomous workflows actually an improvement for experienced engineers? In this episode, Ben Griswold (Grizen) and Noah Heldman (OutcomeSource) compare...

Rolling out AI tools in an enterprise requires a different strategy than a traditional software implementation. Because large language models are probabilistic and constantly evolving, top-down mandates often lead to poor adoption or employees quickly dismissing the technology as unreliable. In this episode, Ben Griswold (Grizen) and Noah Heldman (OutcomeSource) welcome Boz Vitanova, CEO of TeamLi...

Ever feel like basic professionalism (like returning a phone call, showing up on time, or actually listening to a client) has become a rare superpower? You aren't alone. In fact, it might be the easiest competitive advantage you can build. In this episode, Ben Griswold (Grizen) and Noah Heldman (OutcomeSource) unpack a simple but profound truth about the modern workplace: the bar for success is sh...

Organizations everywhere are rushing to implement AI, often measuring success by how many employees are actively using the tools. But treating AI adoption as a simple numbers game completely misses the mark. When speed becomes the primary goal, critical thinking is the first casualty. In this episode, Ben Griswold (Grizen) and Noah Heldman (OutcomeSource) welcome Rebecca George, an expert in organ...

The traditional software development life cycle used to follow a fairly predictable breakdown of time spent on analysis, design, coding, and testing. Now that AI agents are capable of generating the code itself, those old percentages are being completely flipped upside down. In this episode, Ben Griswold (Grizen) and Noah Heldman (OutcomeSource) examine how AI is changing the daily reality of soft...

The tech industry moved fast and broke things during the rise of social media, leaving society to figure out the consequences of screen addiction and algorithmic feeds years later. Now, artificial intelligence is evolving at a much faster pace, and the conversation around guardrails is already struggling to keep up. In this episode, Ben Griswold (Grizen) and Noah Heldman (OutcomeSource) look at th...

The ability to generate software with AI has revived the "Build vs. Buy" debate. If a team can spin up a custom CRM or invoicing tool in a few days using AI agents, the value of paying for expensive monthly SaaS subscriptions comes into question. In this episode, Ben Griswold (Grizen) and Noah Heldman (OutcomeSource) discuss whether the SaaS business model is actually in trouble. They share how th...

"Billability," "Utilization," "Chargeability." For consultants, these aren't just buzzwords... they are the metrics that often dictate your worth. But is an hour worked always an hour of value? And where is the ethical line when it comes to billing for research, learning, or dealing with slow internal processes? In this episode, Ben Griswold (Grizen) and Noah Heldman (OutcomeSource) unpack the psy...

"Vibe Coding" has become a popular way to describe building software by simply chatting with an LLM. It feels efficient, but it often lacks engineering rigor. In this episode, Ben Griswold (Grizen) and Noah Heldman (OutcomeSource) discuss the difference between this casual approach and "Spec-Based Coding." They share a recent experience using Cursor to build a complex feature. The AI agent got the...

What happens when a perfectly designed software system crashes in production because of a single deployment error? You learn the most important lesson in engineering: If you write it, you run it. In this episode, Ben and Noah welcome long-time colleague and technology thought leader Dave Holbrook (CTO at Owner.com ). Dave shares his journey from the world of massive enterprises to the fast-paced r...

We all know the problem: a company sets a high-level strategy, but the teams on the ground have no idea how their daily work connects to it. Enter EDGE , a value-driven operating model designed to close that gap. But can a framework built for massive enterprises actually work for smaller teams? In this episode, Ben Griswold (Grizen) and Noah Heldman (OutcomeSource) dive deep into the principles of...

What will break first as companies scale with AI? Which buzzword will we all be sick of by December? And what's the biggest lie tech leaders will tell themselves this year? It's time to make some predictions. In this special New Year's episode, Ben Griswold (Grizen) and Noah Heldman (OutcomeSource) put on their prognostication hats for a lightning round of tech predictions for the year ahead. From...

There are two hard things in computer science: cache invalidation and naming things. In this episode, we tackle the latter. A single word like "integration" or "account" can mean entirely different things to a COO, a salesperson, and an engineer, leading to confusion, rework, and failed projects. The solution? A "ubiquitous language." Join Ben Griswold (Grizen) and Noah Heldman (OutcomeSource) as...

For any consultant, especially one starting their own firm, the idea of saying "no" to paid work can feel unthinkable. But not all clients are created equal, and taking on the wrong engagement can be far more costly than turning it down. How do you spot the red flags of a toxic environment, avoid burnout, and know when to walk away? In this episode, Ben Griswold (Grizen) and Noah Heldman (OutcomeS...

What if the relentless pursuit of superhuman AI has only one possible, inevitable outcome: the complete annihilation of humanity? That's the terrifying premise of a new #1 bestselling book that's grabbing attention everywhere from subway ads to Silicon Valley. In this episode, Noah Heldman (OutcomeSource) dives into the chilling arguments from "If Anyone Builds It, Everyone Dies: Why Superhuman AI...

Every project starts with a bang and ends with a sprint to the finish line. But what about the long, messy middle? That's where "engagement drift" sets in—when focus blurs, momentum stalls, and even the best-laid plans go off the rails. In this episode, Ben Griswold (Grizen) and Noah Heldman (OutcomeSource) diagnose this common project ailment. They explore the dynamic between "starters" (like Noa...

What has truly changed in the world of technology consulting over the last 20 years, and what fundamental truths have stayed exactly the same? In this special episode, we welcome our very first guest, veteran consultant and startup CTO Jeff Treuting, for a deep dive into the evolution of the industry. Ben, Noah, and Jeff—colleagues and friends for two decades—share stories and insights from their...

In a special new format, we're turning the tables on ourselves! Before we ask our future guests to run the gauntlet, we're answering the five rapid-fire questions that will become a staple of the Regular Expressions podcast. What's the one buzzword we'd ban forever? What was our most embarrassing career fail? What's the one skill we'd instantly master? Join Ben Griswold (Grizen) and Noah Heldman (...

What happens when you push an AI so hard with a real-world coding problem that it... gives up? In a surprisingly human moment, Google's Gemini admitted its approach was "fundamentally wrong," lost its user's trust, and promised to "stop." This wasn't just a glitch; it was a profound lesson in the real-world limitations and opportunities of generative AI. In this episode, Ben Griswold (Grizen) and...

For two career technologists to say "technology is the easy part" might sound strange, but after decades in the industry, it's the most important lesson they've learned. The biggest challenges that derail projects and frustrate teams rarely have to do with code; they have to do with people, processes, and a fundamental disconnect from the business's real purpose. In this episode, Ben Griswold (Gri...

You've heard the buzzword "Forward Deployed Engineer" used by companies like OpenAI and Palantir, but what does it really mean? It’s more than just a senior consultant on-site; it’s a radical model of autonomy, strategy, and on-the-ground invention that challenges the very structure of traditional consulting. In this episode, Ben Griswold (Grizen) and Noah Heldman (OutcomeSource) explore the power...