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Aakash GuptaAakash 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.

Aakash GuptahostDave Killeenguest
Mar 8, 202653mWatch on YouTube ↗

At a glance

WHAT IT’S REALLY ABOUT

Claude Code-powered personal OS automates planning, intel, and workflows daily

  1. Dave Killeen demonstrates a “daily plan” command that automatically compiles calendar, goals, meeting notes, CRM signals, and market intel into a prioritized, redactable briefing each morning.
  2. The system is built on “living” markdown files that continuously accumulate context (projects, people, tasks, meetings), making future AI assistance more accurate and personalized than cloud chat history alone.
  3. He explains how MCP servers provide deterministic guardrails for pulling/structuring data from external tools (e.g., CRM, LinkedIn scraping, analytics) while skills/commands orchestrate repeatable workflows like health scoring and PRD generation.
  4. Claude Code hooks—especially session-start hooks—turn each new chat into a pre-primed workspace by injecting goals, priorities, preferences, and mistake logs, enabling compounding improvement over time.
  5. The workflow extends beyond work execution into career planning by collecting evidence, identifying skill gaps, and mapping career goals down to quarterly and weekly actions with ongoing feedback loops.

IDEAS WORTH REMEMBERING

5 ideas

Treat your work system as compounding “living files,” not chat threads.

Dex appends new evidence (meetings, stakeholder updates, tasks) into entity-centric markdown pages (people/project/company), so Claude can reliably retrieve fresh context later instead of relying on opaque chat memory.

Start your day with a single command that assembles decisions, not data.

The daily plan command aggregates calendar, weekly/quarterly goals, action items, CRM/account signals, and external intel, then outputs “three things that matter today” plus suggested scheduling and drafted messages.

Use MCP servers when you need consistency and guardrails; use skills for workflows.

Killeen frames MCP as more deterministic than skills: MCP enforces structured steps for integrating services and creating artifacts (e.g., tasks with required pillars), while skills/commands are higher-level job descriptions that may be less reliable.

Session-start hooks are the ‘guarantor’ of context and behavior.

Because Claude.md isn’t always adhered to, he prefers Claude Code hooks (available in terminal/desktop) to inject priorities, projects, preferences, and mistake-prevention context at the beginning of every new session.

Your Claude.md should be short and act like an index (progressive disclosure).

He recommends keeping Claude.md token-light—identity, behaviors, “sparring” instructions, bloat radar—then pointing the model to deeper files as needed to maintain performance and reduce drift.

WORDS WORTH SAVING

5 quotes

So I run one command in the morning, and five minutes later, I know what deals need attention, who I'm meeting, what I owe them, and what they owe me. And I didn't gather any of it. The system does it all for me.

— Dave Killeen

It never forgets anything. It never needs to be brought up to speed, and it operates at the speed of our conversation. Everything compounds. All the files get smarter and smarter. They're living files. The more you dance with them, the more useful they become for you and your AI.

— Dave Killeen

Everything and anything that I can get my dirty, grubby hands on that has an API, I create an MCP server for and I bring it in.

— Dave Killeen

I think with AI, it's all about the taste, right? I mean, you could go to town and go, "Okay, implement the entire backlog here." That's just Frankenstein territory, right?

— Dave Killeen

The kindest thing you can do to the AI is give it a very, very clear goal. If you give it that, it'll work out how to get there. Don't tell it how to get to a place. Let it figure it out itself, and it will do it in the most elegant way possible.

— Dave Killeen

Dex open-source personal operating system (markdown-first PKM)Daily plan command (goals + calendar + intel digests)MCP servers vs skills/commands (guardrails vs orchestration)Claude Code hooks (session start, preferences, mistakes logging)Account/deal intelligence and health scoring (CRM-driven)PRD generation from backlog ideas + “taste”/editor roleIntel scanning across YouTube/newsletters/Twitter + clusteringClaude.md design and progressive disclosureKanban board UI for PRD/agent work-in-progress managementLLM-neutral agent harnesses (Pi, OpenClaw) and tool hype debate

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