Aakash Gupta

How I Use Claude Code to Run My Entire Work Life (No Coding Required)

Dave Killeen is the Field CPO at Pendo.io with 25 years in product. He built a personal operating system called DEX in Claude Code that runs his entire workday from one terminal command, pulling from his calendar, CRM, meeting notes, LinkedIn, YouTube, and 120 newsletters. In this episode, he walks through the full system live on screen and shows you how to build your own. Full Writeup: https://www.news.aakashg.com/p/dave-killeen-podcast Transcript: https://www.aakashg.com/the-personal-operating-system-from-pendos-field-cpo/ DEX GitHub: https://github.com/davekilleen/Dex --- Timestamps: 0:00 - Intro 1:47 - Live demo of the daily plan command 5:43 - Daily plan output and account intelligence 10:13 - Ads 11:53 - Claude Code terminal vs Cursor 16:46 - From backlog idea to a full PRD 21:42 - The Claude MD file walkthrough 25:02 - Kanban board for managing PRDs 28:38 - Career planning with the career MCP server 31:00 - Ads 33:42 - Skills vs MCP servers vs hooks explained 36:36 - Intelligence scanning across YouTube and newsletters 40:11 - Hooks deep dive and session start hooks 44:58 - Pi, Open Claw, and LLM-neutral agents 49:02 - What is overhyped vs underhyped in AI tooling 52:14 - Outro --- 🏆 Thanks to our sponsors: 1. Pendo: The #1 software experience management platform - http://www.pendo.io/aakash 2. Jira Product Discovery: Plan with purpose, ship with confidence - https://www.atlassian.com/software/jira/product-discovery 3. Amplitude: The market-leader in product analytics - https://amplitude.com/session-replay?utm_campaign=session-replay-launch-2025&utm_source=linkedin&utm_medium=organic-social&utm_content=productgrowthpodcast 4. NayaOne: Airgapped cloud-agnostic sandbox - https://nayaone.com/aakash/ 5. Product Faculty: Get $550 off the AI PM Certification with code AAKASH550C7 - https://maven.com/product-faculty/ai-product-management-certification?promoCode=AAKASH550C7 --- Key Takeaways: 1. One command replaces your morning routine - Dave's daily plan slash command pulls from calendar, CRM, Granola, LinkedIn, YouTube, and 120 newsletters in five minutes. No tab switching. No manual assembly. 2. MCP servers are the key to connecting everything - Point Claude at any API documentation with your API key and it builds an MCP server for you. MCP provides structured guardrails that make the AI's behavior consistent and deterministic. 3. Skills, MCP, and hooks are three different things - Skills are plain English job descriptions for what the AI should do. MCP servers are structured integrations for connecting external services. Hooks are triggers that fire at specific conversation moments. 4. Session start hooks make the system compound - Every new Claude Code chat gets injected with weekly priorities, quarterly goals, working preferences, and past mistakes. The AI never starts from scratch. 5. Living markdown files are the compounding mechanism - Every project, person, and company gets a markdown file that accumulates context from meetings, messages, and intel over time. The more you use the system, the smarter every file becomes. 6. You can build a mobile app in 37 minutes - Dave built the full app with Claude and spent more time in Xcode publishing it. The constraint is taste, not building speed. 7. The AI should hold you accountable - Dave's Claude MD file includes "harsh truths for Dave" that the AI wrote after auditing his system. This gets injected into every session to prevent the same mistakes. 8. Career planning should compound like product data - A career MCP server collects evidence, runs gap analysis, and calculates promotion readiness. When review time comes, the evidence is already assembled. 9. Be precise about your goal, not the path - The kindest thing you can do for the AI is give it a very clear destination. Do not tell it how to get there. Let it figure out the most elegant approach itself. 10. Voice-first changes everything - Using Whisperflow or Super Whisper instead of typing fundamentally changes how you interact with Claude. You think out loud. The conversation flows. You build faster. --- 👨‍💻 Where to find Dave Killeen: LinkedIn: https://www.linkedin.com/in/davekilleen/ Pendo: https://www.pendo.io DEX GitHub: https://github.com/davekilleen/Dex 👨‍💻 Where to find Aakash: Twitter: https://www.x.com/aakashg0 LinkedIn: https://www.linkedin.com/in/aakashgupta/ Newsletter: https://www.news.aakashg.com #claudecode #aipm --- 🧠 About Product Growth: The world's largest podcast focused solely on product + growth, with over 200K+ listeners. 🔔 Subscribe and turn on notifications to get more videos like this.

AGAakash GuptahostDKDave Killeenguest

Mar 9, 2026·53m·Watch on YouTube ↗

📖 CHAPTERS

1. 1

   Why Claude Code feels like a “personal operating system” (and why it compounds)

   Aakash introduces Dave Killeen and tees up the core claim: Claude Code can run a large portion of your work life without you manually gathering inputs. Dave frames the key advantage as compounding “living files” that get smarter over time—like an always-on executive assistant with perfect memory.

2. 2

   Live demo: the “Daily Plan” command that pulls your whole day together

   Dave runs a single command (via voice) and explains that it aggregates calendar, goals, meeting notes, and multiple intel feeds into one daily brief. The emphasis is on orchestration: Claude pulls from many sources, formats into Markdown, and presents priorities and next actions.

3. 3

   How the system connects to everything: MCP servers, APIs, and voice-to-text

   Aakash probes how the workflow integrates with tools like CRM, forecasting, and newsletters. Dave explains why he prefers MCP servers over direct APIs (guardrails and determinism), and he shares his voice workflow using Whisperflow/Superwhisper to avoid typing.

4. 4

   Daily plan output: account intelligence + market/social intel in one place

   They walk through the generated daily page: top priorities, weekly alignment, and proactive suggestions for customer/account follow-ups. Dave shows how it summarizes YouTube/newsletters, surfaces LinkedIn messages worth replying to, and drafts outreach messages—reducing context switching across tools.

5. 5

   Cursor vs Claude Code in Terminal: why hooks change the game

   Aakash asks about terminal fear and why Dave sometimes uses Cursor. Dave explains that terminal usage unlocks Claude Code hooks—especially session-start hooks that automatically inject context and make every new chat smarter and more consistent than relying on a static Claude.md alone.

6. 6

   X-ray skill: exposing how a command works (Mermaid diagrams + dependency checks)

   Dave demonstrates an “X-ray” command that reveals the internals of the Daily Plan flow. It outputs a diagrammed pipeline showing which files are read, which digests must exist, and how missing intel is generated before composing the final plan.

7. 7

   Beyond planning: proactive account health scoring and deal attention

   After daily planning, Dave runs a health score skill to quickly assess which accounts need help. The key takeaway is creating reusable “skills/commands” that operationalize repeated leadership tasks and make proactive support easier.

8. 8

   From backlog idea to PRD in minutes (and why “taste” matters)

   Dave shows a Dex backlog that ranks ideas and then converts a selected idea into a full PRD using the system’s context. They discuss the PM/CPO role shifting from writing everything to exercising taste—selecting, refining, and steering AI-generated outputs.

9. 9

   Claude.md as your operating manual: progressive disclosure + “harsh truths”

   They open Dave’s Claude.md file and discuss how it encodes product identity, sparring style, and anti-bloat rules. Aakash advises version-controlling Claude.md because iterative tweaks can regress behavior; Dave highlights progressive disclosure to keep prompts token-efficient.

10. 10

    Taming PRD sprawl with a local Kanban UI (built in hours)

    Dave demos a localhost React app that visualizes PRDs as a Kanban board, including scoring and next-step recommendations. He frames this as “malleable software”: when a pain appears (overwhelm), you build the missing interface to match how you work.

11. 11

    Career planning via a ‘Career MCP server’: evidence, gaps, readiness scoring

    They expand the ‘operating system’ beyond tasks into personal development. Dave shows a career MCP server that gathers evidence from work artifacts, runs skills-gap analysis, and maps career goals down to quarterly and weekly actions to highlight missing activity.

12. 12

    Skills vs MCP servers vs hooks: what each is for (and when to use them)

    Aakash asks for a clear mental model. Dave distinguishes skills/commands (job descriptions), MCP servers (deterministic tool access with guardrails), and hooks (automatic lifecycle triggers that inject context and write learnings).

13. 13

    Intelligence scanning across YouTube, newsletters, Twitter—and auto-improving Dex

    Dave explains his daily intel pipeline: ingest transcripts/newsletters/bookmarks into Markdown, cluster themes, and surface contrarian/novel insights. He also describes a “Dex improve” command that monitors Anthropic releases + HN/Reddit and suggests system upgrades in priority order.

14. 14

    Hooks deep dive: session-start context, mistake logs, and preference learning

    They go deeper on why hooks are transformative: every new session starts preloaded with priorities, pillars, and tasks, and the system can write to files when mistakes happen or when preferences are expressed. The result is a system that improves like ‘compound engineering’—but for knowledge work.

15. 15

    Getting started + the future: onboarding Dex, LLM-neutral agents, and hype check

    Dave walks through cloning Dex from GitHub, running setup, and role-based scaffolding for non-engineers. They discuss Pi/OpenClaw and the direction toward LLM-neutral agent harnesses, then close with what’s overhyped vs underhyped and final encouragement to stop watching and start building.