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Paul Thurrott is back to talk about everything that happened to Windows in 2025, and what that might hold for 2026.

The post RunAsRadio #1016: What Windows Wants for Christmas with Paul Thurrott appeared first on Thurrott.com.

Matt MacInnis is the chief product officer and former longtime COO at Rippling, a unified workforce management platform valued at over $16 billion.

We discuss:

1. Why “extraordinary results demand extraordinary efforts”

2. Why you should deliberately understaff projects, and how to know when you’ve gone too far

3. Matt’s transition from COO to CPO and what surprised him about leading product

4. The “high alpha, low beta” framework for evaluating people, processes, and products

5. When founders should quit their startups (hint: much earlier than VCs want you to)

6. How to fight entropy in your organization through relentless energy and intensity

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Brought to you by:

Google Gemini—Your everyday AI assistant: https://ai.dev/

Datadog—Now home to Eppo, the leading experimentation and feature flagging platform: https://www.datadoghq.com/lenny

GoFundMe Giving Funds—Make year-end giving easy: http://gofundme.com/lenny

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Transcript: https://www.lennysnewsletter.com/p/10-contrarian-leadership-truths

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My biggest takeaways (for paid newsletter subscribers): https://www.lennysnewsletter.com/i/181916584/my-biggest-takeaways-from-this-conversation

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Where to find Matt MacInnis:

• X: https://x.com/stanine

• LinkedIn: https://www.linkedin.com/in/macinnis

• Email: macinnis@rippling.com

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Where to find Lenny:

• Newsletter: https://www.lennysnewsletter.com

• X: https://twitter.com/lennysan

• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/

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In this episode, we cover:

(00:00) Introduction to Matt MacInnis and Rippling

(04:38) The importance of extraordinary efforts

(08:37) The challenges and rewards of relentless effort

(10:11) Your job as a leader is to preserve intensity

(12:39) You learn far more from success than failure

(16:34) Transitioning to chief product officer

(19:54) Fixing product management at Rippling

(25:27) The “high alpha, low beta” framework

(28:55) The PQL framework

(35:16) Hiring frameworks and team dynamics

(36:52) A helpful interview tactic

(40:00) Leading as a COO vs. a CPO

(42:34) The reality of product-market fit

(46:38) The problem with venture capital

(49:29) When founders should quit their startups

(41:48) The immutable market

(54:13) Lessons from Notion’s success

(57:43) Investment strategies and narrative violations

(01:00:42) The power of compounding, power law, and entropy

(01:07:02) Maintaining intensity and fighting entropy

(01:11:33) The importance of feedback and escalations

(01:14:31) Rippling’s vision and success

(01:17:48) AI’s impact on SaaS and business software

(01:23:42) AI corner

(01:26:23) Final thoughts and lightning round

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Referenced:

• Rippling: https://www.rippling.com

• Sunil Raman on LinkedIn: https://www.linkedin.com/in/sunilraman

• Dan Gill on LinkedIn: https://www.linkedin.com/in/dangill

• Carvana: https://www.carvana.com

• Brian Chesky’s new playbook: https://www.lennysnewsletter.com/p/brian-cheskys-contrarian-approach

• Parker Conrad on LinkedIn: https://www.linkedin.com/in/parkerconrad

• Inkling: https://www.inkling.com

• Akshay Kothari on LinkedIn: https://www.linkedin.com/in/akothari

• Notion: https://www.notion.com

• Conway’s law: https://en.wikipedia.org/wiki/Conway%27s_law

• Seeking Alpha: https://seekingalpha.com

• Dennis Rodman’s website: https://dennisrodman.com

• Dancing pickle emoji: https://slackmojis.com/emojis/456-dancing_pickle

• Pickle Rick: https://en.wikipedia.org/wiki/Pickle_Rick

• SPOTAK: The Six Traits I Look for When I’m Hiring: https://finance.yahoo.com/news/spotak-six-traits-look-m-181335267.html

• Geoff Lewis on LinkedIn: https://www.linkedin.com/in/geofflewis1

• Zenefits: https://en.wikipedia.org/wiki/TriNet_Zenefits

• New banking records prove Deel paid thief who stole trade secrets from Rippling: https://www.rippling.com/blog/new-banking-records-prove-deel-paid-thief-who-stole-trade-secrets-from-rippling

• Workday: https://www.workday.com

• Matic robots: https://maticrobots.com

• Wall-E: https://www.imdb.com/title/tt0910970

• Conviction: https://www.conviction.com

• Mike Vernal on X: https://x.com/mvernal

• Sarah Guo on X: https://x.com/saranormous

• No Priors: https://linktr.ee/nopriors

• Gemini: https://gemini.google.com

• ChatGPT: https://chatgpt.com

• Claude: https://claude.ai

• Bryan Schreier on LinkedIn: https://www.linkedin.com/in/bryanschreier

• Heated Rivalry on HBO Max: https://www.hbomax.com/shows/heated-rivalry/50cd4e99-04ee-427b-a3b4-da721ed05d9c

• Fellow coffee maker: https://fellowproducts.com/products/aiden-precision-coffee-maker

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Recommended books:

• Pale Blue Dot: A Vision of the Human Future in Space: https://www.amazon.com/Pale-Blue-Dot-Vision-Future/dp/0345376595

• Conscious Business: How to Build Value Through Values: https://www.amazon.com/Conscious-Business-Build-through-Values/dp/1622032020

• Thinking in Systems: https://www.amazon.com/Thinking-Systems-Donella-H-Meadows/dp/1603580557

• The Effective Executive: The Definitive Guide to Getting the Right Things Done: https://www.amazon.com/Effective-Executive-Definitive-Harperbusiness-Essentials/dp/0060833459

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Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.

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Lenny may be an investor in the companies discussed.

Terminal customization just got a lot smarter. Oh My Posh now integrates with Claude Code through its statusline functionality, bringing real-time AI session information and development context directly into your Claude Code prompt.

This isn't just another segment: it's a bridge between your development workflow and AI-powered coding assistance.

What is Claude Code's statusline?

Claude Code's statusline feature allows you to create custom status displays that appear at the bottom of the Claude Code interface, similar to how terminal prompts work in shells. The statusline receives rich JSON data about your current AI session via stdin, including:

• Model information: Which Claude model you're using (Claude Sonnet, Claude Opus, etc.)
• Token usage: Input/output tokens, context window utilization, and usage percentages
• Cost tracking: Real-time cost calculations and session duration
• Workspace context: Current and project directories
• Session metadata: Unique session IDs and version information

The statusline updates automatically when conversation messages change (throttled to every 300ms max), and Oh My posh creates the status display with full ANSI color support.

Setting Up the Integration

Configuration is straightforward. Add this to your Claude Code settings:

{
  "statusLine": {
    "command": "oh-my-posh claude"
  }
}

That's it! Oh My Posh will automatically detect when Claude Code provides session data and display the relevant information in your prompt.

It's important to note that the claude CLI command operates differently from your regular prompt configuration. When used as a statusline command, Oh My Posh runs in a special mode that's completely separate from your standard terminal prompt. This means you'll likely want to create a dedicated, minimal configuration specifically for Claude Code that focuses on displaying AI session information rather than your usual prompt elements.

By default, the oh-my-posh claude command provides a built-in statusline that shows your current working directory, git context, active model name, and context window usage as a visual gauge. To customize this display, use the --config flag to specify your own theme configuration file that includes a custom claude segment tailored to your preferences.

The Claude Code segment

Oh My Posh's new claude segment taps into this statusline data to bring AI session awareness directly into your terminal prompt. When you use the oh-my-posh claude command as your statusline command in Claude Code, you get access to a wealth of session information that can be displayed in your prompt without needing to know the technical details.

Example Configuration

Here's a sample configuration that shows the model name and context usage:

{
  "type": "claude",
  "style": "diamond",
  "leading_diamond": "\ue0b6",
  "trailing_diamond": "\ue0b4",
  "foreground": "#FFFFFF",
  "background": "#FF6B35",
  "template": " \udb82\udfc9 {{ .Model.DisplayName }} \uf2d0 {{ .TokenUsagePercent.Gauge }} "
}

This displays something like: 🤖 Claude 4.5 Sonnet ▰▰▰▱▱

The gauge provides instant visual feedback on how much of your context window you've consumed, which is crucial for managing long coding sessions.

The Technical Details

Under the hood, Oh My Posh reads the rich JSON session data that Claude Code provides via stdin when used as a statusline command. The segment only activates when Claude Code session data is available, so there's no performance impact when you're not using Claude Code.

Getting Started

If you're already using Oh My Posh, adding Claude Code integration is as simple as:

1. Install Claude Code if you haven't already
2. Add the statusline configuration to your Claude Code settings
3. Optionally create your own configuration including the claude segment
4. Start a Claude Code session and watch your prompt come alive

For detailed configuration options and all available properties, check out the complete Claude segment documentation.

What's Next?

This integration opens up exciting possibilities. Imagine prompts that:

• Change color based on token usage percentage
• Show different icons for different AI models
• Display cost warnings when sessions get expensive
• Integrate with any other segment to show additional development context

The foundation is there, and now it's up to the community to build amazing configurations that make AI-powered development even more seamless.