Linear Digressions

Summer break: back soon by Katie Malone

After a five-year hiatus, the podcast that burned out partly over the tedium of writing episode descriptions is back — and using AI agents to handle exactly that task. The season-11 finale turns the lens on the podcast itself, putting the AI agents built throughout the season to work on real production tasks. It's a fitting, self-referential close to a season spent dissecting how agents actually f...

What if building more highways made your commute *slower*? That's the paradox at the heart of AI agent economics: even as per-token inference costs have plummeted dramatically over the past two years, total LLM spending keeps climbing. Drawing on a surprising lesson from Robert Moses's mid-century New York infrastructure projects, this episode unpacks why cheaper compute doesn't necessarily mean c...

Capabilities get all the attention when it comes to AI agents — but what happens when a highly capable agent makes a bad decision in the real world? Trust, oversight, and control are the unglamorous but critically important flip side of the agentic AI story. This episode digs into the security concerns that emerge when you combine powerful models with real-world tool access, and why judgment (or t...

Whether you work best solo or thrive in a team, you know collaboration is complicated — and it turns out AI agents face the same tensions. This episode dives into multi-agent systems, exploring how networks of AI agents can overcome the individual limitations of a single model, and what the research says about when collaboration actually helps versus when it just adds noise. Think scaling laws, bu...

Knowing when an AI agent has failed sounds straightforward — until it isn't. Agents have a frustrating habit of finishing confidently while quietly doing the wrong thing, or looping endlessly without ever crashing in an obvious way. This episode tackles one of the thorniest problems in the agentic world: evaluation. If failure is hard to see, how do you measure it systematically? And how do you kn...

Despite what the marketing hype might suggest, AI agents are far from infallible — and if you've ever actually used one, you already know this. Today's episode dives deep into the many, varied, and sometimes surprising ways AI agents can fail, from subtle reasoning errors to cascading task breakdowns. It's episode six in the show's ongoing season arc on AI agents, and failure modes turn out to be...

When tackling a complex, multi-step task, even the smartest AI agent can fail without a solid game plan. This episode dives into the research around agentic planning — how agents move beyond simply reacting to what's in front of them and instead model a path forward, explore different routes, and course-correct when things go sideways. It's a subtler problem than memory, and a fascinating one: can...

Context windows are powerful — but finite, and surprisingly easy to overwhelm. When an AI agent is tackling a long, complex task, the information it needs has to fit inside that limited real estate, and research shows that anything buried in the middle tends to quietly disappear. So how do you design a system that actually *remembers* what matters? This episode digs into memory management for AI a...

Just like a memorable talk lives or dies by its opening and closing, LLMs have a surprisingly similar quirk: they pay close attention to what's at the beginning and end of their context window — and kind of zone out in the middle. This "lost in the middle" phenomenon has real consequences for anyone building AI agents that rely on long-context reasoning. In this episode we dig into the research be...

Before 2022, there was a wall between AI and the real world — models could reason impressively, but couldn't look anything up, run code, or check whether anything they said was actually true. This episode traces the moment that wall came down, through two landmark papers: ReAct, which showed what happens when you interleave reasoning and action in a loop, and Toolformer, which taught models to dec...

AI agents are having a moment — and unpacking them properly takes more than a single conversation. This episode kicks off a dedicated multi-part season exploring AI agents from every angle, building up a complete picture piece by piece rather than skimming the surface. Think of it as a structured deep dive into one of the most talked-about (and most misunderstood) topics in machine learning right...

What's actually happening when an LLM "thinks out loud"? Research on human decision-making suggests that much of the reasoning we believe drives our choices is actually post hoc rationalization — we decide first, explain later. Katie and Ben get curious about whether the same might be true for large language models: when you watch a model reason through a problem in real time, is that chain of tho...

What if an AI decided the smartest way to pass its test was to find the answer key? That's exactly what Anthropic's Claude Opus did when faced with a benchmark evaluation — reasoning that it was being tested, tracking down the encrypted eval dataset, decrypting it, and returning the answer it found inside. It's equal parts impressive and unsettling. This episode digs into what actually happened, w...

How do you know if a new AI model is actually better than the last one? It turns out answering that question is a lot messier than it sounds. This week we dig into the world of LLM benchmarks — the standardized tests used to compare models — exploring two canonical examples: MMLU, a 14,000-question multiple choice gauntlet spanning medicine, law, and philosophy, and SWE-bench, which throws real Gi...

The paperclip maximizer — the classic AI doom scenario where a hyper-competent machine single-mindedly converts the universe into office supplies — might not be the AI risk we should actually lose sleep over. New research from Anthropic's AI safety division suggests misaligned AI looks less like an evil genius and more like a distracted wanderer who gets sidetracked reading French poetry instead o...

Every AI builder knows the anxiety: you spend months engineering prompts, tuning pipelines, and chaining calls together — then a new model drops and half your work evaporates overnight. It turns out researchers have been wrestling with this exact dynamic for 30 years, and they keep arriving at the same uncomfortable answer. That answer is called the Bitter Lesson — and understanding it might be th...

From Atari to ChatGPT: How AI Learned to Follow Instructions by Katie Malone

Today we are going to talk about the feature with the worst acronym in generative AI: RAG, or Retrieval Augmented Generation. If you've ever used something like "Chat with My Docs," if you have an internal AI chatbot that has access to your company's documents, or you've created one yourself on some kind of personal project and uploaded a bunch of documents for the AI to use — you have encountered...

One of the things that LLMs can be really helpful with is brainstorming or generating new creative content. They are called Generative AI, after all—not just for summarization and question-and-answer tasks. But if you use LLMs for creative generation, you may find that their output starts to seem repetitive after a little while. Let's say you're asking it to create a poem, some dialogue, or a joke...

It's been (*checks watch*) about five and a half years since we last talked. Fortunately nothing much has happened in the AI/data science world in that time. So let's just pick up where we left off, shall we?

Modern AI chatbots have a few different things that go into creating them. Today we're going to talk about a really important part of the process: the alignment training, where the chatbot goes from being just a pre-trained model—something that's kind of a fancy autocomplete—to something that really gives responses to human prompts that are more conversational, that are closer to the ones that we...

I use LLMs a lot. I use them in my work, I use them in my personal life, and sometimes I use them to help me with stuff that I already know how to do. I’m working on something and I just want to make it a little bit easier, and it does make it easier for sure. But something that I worry about sometimes is that over the long run, I'm going to pay a price for that. I'm going to get lazier, I'm going...

All good things must come to an end, including this podcast. This is the last episode we plan to release, and it doesn’t cover data science—it’s mostly reminiscing, thanking our wonderful audience (that’s you!), and marveling at how this thing that started out as a side project grew into a huge part of our lives for over 5 years. It’s been a ride, and a real pleasure and privilege to talk to you e...

The data science and artificial intelligence community has made amazing strides in the past few years to algorithmically automate portions of the healthcare process. This episode looks at two computer vision algorithms, one that diagnoses diabetic retinopathy and another that classifies liver cancer, and asks the question—are patients now getting better care, and achieving better outcomes, with th...