Context and Memory
299 episodes · Page 4 of 13
#4340: Building an AI Tutor That Teaches You to Code Without Writing It For You
How to build an AI tutor that assigns projects, reviews code, and remembers what you've learned — without writing your code for you.
#4316: How to Build Memory That Survives AI Sessions
Why AI agents forget between sessions — and how to fix it with markdown files instead of black-box memory.
#4314: The Hidden Layer Shaping Every AI Chat
Context windows are huge now, but relevance is the real bottleneck. How middleware decides what your AI actually sees.
#4312: Why Speech-to-Text Still Fails at Its Own Name
When OpenAI's Whisper misheard its own name as "Wispr," it revealed why 95% word accuracy still isn't good enough.
#4296: Auto-Splitting AI Threads: Smarter Context Management
How to build a system that automatically detects topic shifts and routes messages to the right thread.
#4194: Custom GPTs: When to Build, When to Skip
A decision framework for knowing when a custom GPT is worth the overhead — and when to just open a fresh chat.
#4157: Prompt Engineering Is a Misnomer — Managing Ambiguity in AI
Why the best AI outputs come not from tighter prompts, but from knowing where to leave room for surprise.
#4139: The Hosepipe-to-Digest AI: Your Outbox Middleware
An AI middleware that intercepts your outgoing emails, buffers them, and delivers a crisp executive summary.
#4106: Embedding Models vs LLMs: What Actually Connects?
Can you mix any embedding model with any LLM? And why are new embedding models still dropping if they're "solved"?
#4104: Why 20% of AI Scripts Loop on Themselves
Debugging the mysterious repetition bug affecting one in five podcast episodes.
#4094: One Mind or Two? AI Podcast Dialogue Showdown
Can two AI agents create better podcast banter than one? We explore the tradeoffs.
#4092: How AI Remembers What You Never Told It
How ChatGPT connected "wall anchors" to a power tool you bought days ago — without being asked.
#4069: How AI Is Rewriting Your Tech Stack Choices
What happens when AI agents change how we pick frameworks, ORMs, and databases?
#4058: Can AI Agents Ever Be Truly Social?
Text-based AI simulations look social, but do they understand anything? We explore the gap between pattern-matching and real social intelligence.
#3846: How to Save Your Company's Secret Second Brain
Tacit knowledge is walking out the door. Here's how to capture it before it's gone.
#3816: How to Stop AI Scripts From Falling Apart
Why long-form AI generation breaks down and how hierarchical memory fixes it.
#3673: Knowledge Graphs vs SQL: How Custom Relationships Change Retrieval
Why naming relationships (not just connecting data) transforms how you retrieve information.
#3661: What 1000 AI Podcast Episodes Actually Prove
Scaling an AI podcast to 1000 episodes reveals what no 10-episode pilot can teach you about sustainability, cost, and habit formation.
#3171: How to Break an LLM's Bad Verbal Habits
Blacklists fail and regex inverts meaning. Here's what actually works to clean up AI writing tics.
#3127: Crafting AI Characters That Feel Alive
Move beyond system prompts with structured character bibles that give AI personalities real inner lives.
#3120: What Makes Agentic Search Tools Like Exa Actually Work?
Why swapping Google for Exa transformed our show's accuracy — and what agentic search does differently.
#2936: Why AI Still Can't Really Teach You to Code
Code generators ship code. Real tutors build understanding. Why the gap is bigger than you think.
#2914: Can AI Read the Room? TTS Prosody Explained
Can TTS models truly infer emotion from text, or just mimic patterns? We break down the science of prosody.
#2808: Falling for Your Chatbot: Love, Loss, and Language Models
Real cases of people falling in love with AI companions, why memory makes it feel real, and what happens when the illusion breaks.