Luis Calderon

Contextually Aware

What product managers can actually build with AI today—and where it still breaks.

Author

Luis Calderon

Category

Technology

Podcast website

contextuallyaware.com

Latest episode

Jul 10, 2026

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Episodes

Your Code Is Trash Anyway 10.07.2026

The production curve for generating code is steeper than understanding it. Teams that win store decisions, not commits—and specs are the moat. This episode is in DRAFT and has not been published yet.

Your Agents Have Amnesia — Stop Using Markdown! 10.07.2026

Why stuffing context into markdown files breaks production AI agents, and the six-layer memory architecture that actually works at scale. This episode is in DRAFT and has not been published yet.

Why Agent Memory Needs an OS, Not a Vector Store 10.07.2026

Production agents hit a wall around day 30: context drift, not retrieval, is the killer. Vector stores can't manage state across multi-agent workflows. The fix is treating memory like an operating system. This episode is in DRAFT and has not been published yet.

When Not to Deploy an Agent 10.07.2026

Luis explores five conditions that should trigger a pause before deploying an AI agent—and why a queue, form, or policy often solves the problem faster than autonomy. This episode is in DRAFT and has not been published yet.

What Broke When We Scaled to 17 Agents 10.07.2026

Luis walks through five coordination failures that emerge when agent systems scale past single digits—memory contention, context bloat, skill drift, context corruption, and operator blindness. The fix: a memory OS layer that governs writes, gates context, standardizes skills, checkpoints state, and This episode is in DRAFT and has not been published yet.

The Trillion-Dollar Fork: Who Owns the Harness? 10.07.2026

OpenAI and Anthropic's IPO valuations hinge on owning the work layer above AI models—not just cheap tokens, but proprietary harnesses. We explore why context, memory, and workflow engineering are where real competitive advantage lives. This episode is in DRAFT and has not been published yet.

Three things broke this week. None of them were the model. 10.07.2026

Palantir's CEO ranted about AI pricing, a ransomware agent proved harness engineering matters more than the model, and Mem0 benchmarked the memory layer nobody is paying attention to. The real fight isn't about weights—it's about what sits underneath. This episode is in DRAFT and has not been published yet.

The deployment PM is dead 10.07.2026

The job description we wrote for PMs in 2019 doesn't match the work in 2026. Luis breaks down what's actually required to survive the AI era. This episode is in DRAFT and has not been published yet.

The Audit Trail Is the Product 10.07.2026

Why the audit trail—not the agent's output—is what actually matters in production. Design it as a user interface, and autonomy becomes defensible. This episode is in DRAFT and has not been published yet.

The AI Strategy Slide Deck Is Dead 10.07.2026

Luis argues that static AI strategy decks are obsolete. The future is live orchestration graphs where agents execute workflows in real time while humans design the feedback loop. This episode is in DRAFT and has not been published yet.

The agentic GitHub stack is forming 10.07.2026

Five product layers are crystallizing in open-source AI agent repos right now. Learn which ones matter and how to borrow the patterns before they harden into expensive platform defaults. This episode is in DRAFT and has not been published yet.

The agent memory wall 10.07.2026

Every AI agent in production hits the same wall: they start from zero every Monday with no memory of past decisions. Luis explores why memory and governance is the one unsolved layer of the agentic stack—and what governed memory actually requires. This episode is in DRAFT and has not been published yet.

Stop Wasting Time Writing Better Prompts 09.07.2026

Prompt engineering is dead. The winning move is prompt systems—evolutionary optimization, self-refinement loops, harness engineering, and spec-driven contracts. Here's how to build them. This episode is in DRAFT and has not been published yet.

The NOC Console for Agent Teams 09.07.2026

When you're running multiple agents in production, you need more than a dashboard—you need a real operator console. Luis breaks down what that looks like and why it matters. This episode is in DRAFT and has not been published yet.

Most PMs Won't Become Agent Orchestrators. They'll Become Obsolete. 09.07.2026

Luis argues the comfortable narrative about PMs evolving into agent orchestrators is false. The real trend: agentic AI will automate the PM role itself, leaving only domain experts and compliance checkpoints. This episode is in DRAFT and has not been published yet.

The Harness Eats the Prompt (Every Time) 09.07.2026

A new paper proves what product builders have suspected: your system prompt is the least valuable part of your AI harness. The real wins come from tool architecture, middleware, and memory structure. This episode is in DRAFT and has not been published yet.

Google I/O 2026 was about distribution 09.07.2026

Google didn't release a smarter model at I/O 2026—it turned 12+ products into agent runtimes. The real story is distribution dominance, not AI capability. This episode is in DRAFT and has not been published yet.

Eval design before agent design 09.07.2026

The cheapest agent improvement happens before you build it. Write your eval first—it's the product spec that prevents plausible-but-untrustworthy outputs. This episode is in DRAFT and has not been published yet.

Build, Buy, Borrow, Hire, or Wait? The AI Investment Framework 09.07.2026

Your board is split on AI strategy. Luis breaks down the five investment motions—build, buy, borrow, hire, wait—and gives you the framework to pick the right one for each workflow. This episode is in DRAFT and has not been published yet.

Software is Dead. Long Live Services. 09.07.2026

Three startups shipped on schedule and hit milestones—then quietly vanished. The real moat isn't code; it's the relationship you build with customers. Read the full article: https://growthalchemylab.com/blog/software-is-dead-long-live-services This episode is in DRAFT and has not been published yet.

The Silent Killer in AI Agent Workflows: Context Drift 09.07.2026

Most agent failures aren't bugs—they're silent context drift happening after step five. Luis Calderon reveals why vector memory fails, and what actually fixes it. Read the full article: https://growthalchemylab.com/blog/the-memory-failure-i-keep-seeing-in-agent-stacks This episode is in DRAFT and has not been published yet.

The Five Breaks: Where Multi-Agent Systems Actually Fail 09.07.2026

Luis Calderon maps the four failure modes that kill multi-agent systems before launch—and the fifth that breaks them in production. Most teams only fix the first three. Read the full article: https://growthalchemylab.com/blog/the-four-places-multi-agent-systems-break This episode is in DRAFT and has not been published yet.

The 2 AM Write That Changed Everything: Building Approval Gates for Autonomous Agents 09.07.2026

When a single blocked write action prevented disaster, one team learned that strategic approval gates—not blanket permissions—unlock true agent autonomy while keeping humans in control. Read the full article: https://growthalchemylab.com/blog/we-blocked-one-write-action This episode is in DRAFT and has not been published yet.

Why Enterprise AI Projects Take 12 Months to Ship (When the Code Takes 2 Weeks) 09.07.2026

Accenture built an AI agent in two weeks but took twelve months to ship it. The bottleneck wasn't technology—it was organizational. We explore the five tensions that predict whether enterprise agentic projects survive. Read the full article: https://growthalchemylab.com/blog/enterprise-agentic-projects-doomed This episode is in DRAFT and has not been published yet.

Your Code Is Trash Anyway—And That's the Whole Point 07.07.2026

Your Code Is Trash Anyway—And That's the Whole Point Short, sharp take on why specs beat prompts, models rewrite everything anyway, and product teams that store decisions—not code—are the ones who win. Your code is going to be rewritten anyway. Models regenerate it. The next engineer rewrites it. Six months from now, nobody remembers why any decision was made. So why are you treating the code as t...

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