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
—
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
—
Transcript: https://www.lennysnewsletter.com/p/10-contrarian-leadership-truths
—
My biggest takeaways (for paid newsletter subscribers): https://www.lennysnewsletter.com/i/181916584/my-biggest-takeaways-from-this-conversation
—
Where to find Matt MacInnis:
• LinkedIn: https://www.linkedin.com/in/macinnis
• Email: macinnis@rippling.com
—
Where to find Lenny:
• Newsletter: https://www.lennysnewsletter.com
• X: https://twitter.com/lennysan
• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/
—
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
—
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
—
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.
—
Lenny may be an investor in the companies discussed.
Hello and Welcome, I’m your Code Monkey!
The end of 2025 is here! As always it feels like the past 12 months just flew by. I hope 2026 will be awesome!
I'm publishing a 2025 Recap video on YouTube tomorrow (premiere), I do this every year, you can see the page with all the best videos of the year (and all previous years)
In total 153 Videos, 3 FREE Courses, and lots of tutorials and miscellaneous videos!
Stay tuned for the Recap video tomorrow and Happy New Year!
Game Dev: Best Game Dev Report 2025

With the year reaching the end it's time to look back at the Best of the Game Dev Report of 2025!
I didn't miss a single week, so that's 52 new issues each covering all sorts of interesting news and articles all about Game Dev, Tech and Gaming.
Here are my highlights of the year:
Dev followed my FREE course, then made $150k!
I love hearing about people following my courses and then going on to find massive success! This was a great story. I hope YOU also find success like this!
Another Solo Dev makes $50 MILLION!
It's been a big year for small teams, Schedule I, Supermarket Simulator, PEAK, Megabonk. It's crazy how as an indie dev your game can either make $0 or $MILLIONS!
What do the best programmers do differently?
If you want to improve your craft then look at what the best people doing it do differently, that's a great way to learn!
Every Daily Deal of 2024 and how much they're worth
Do you know how to get a Daily deal on Steam? And how much is it worth? This year they actually increased the number of slots which means more devs finding more success!
This is an excellent exercise that I recommend you do. Look at something that seems super satisfying, and spend some time breaking it down to understand WHY it's so satisfying.
What makes an Indie Game look Low Effort?
It's important to know what to do, but also just as important to know what NOT to do. Here's a list of things that make games look low effort, study and avoid them!
Dev making MILLIONS with simple strategy
Nowadays finding success is tough so you need to find every edge you can, this one developer found a strategy that is working very well for them! I highly recommend you give it a try.
Roblox is MASSIVE! And maybe you can use that?
Another great strategy is one I covered in this report, use the massive size of Roblox for idea validation.
The NEW Indie Golden age is here!
Making a living as an indie dev is tough, but for some good news it seems we are actually going through an Indie Golden Age! Some genres that are easy to make are also the ones that are finding lots of success!
Game ideas that sound like they SHOULDN'T work, but do!
You can make games about literally anything! If you tell someone who doesn't play games "Oh when I go back home, for fun I like to work at a Supermarket" then that person will look at you like you're crazy, and yet Supermarket Simulator is loved by players!
Rejected by 58 publishers, then made $750k
Another story with a happy ending. Developer tried to get a publisher, failed, self-published instead, and made a ton of money!
The biggest mistake devs make is just making ONE game and then quitting the industry entirely. You learn a ton from every project so if you make more games you will improve your skills and your odds of success drastically.
All the marketing tricks in the world won't work if you miss the #1 rule. On the other hand, if you have it then marketing and finding success becomes infinitely easier!
And something I really enjoy is the FUN section where I've covered all sorts of random stuff, here are my highlights this year:
Really impressive simulation of a web that runs in your browser, you can cut and slice it in any way and the whole thing is physically accurate! The dev even made a tutorial explaining how it works.
I love 3D Printing and this is some fascinating piece of tech. It's a 3D printed cube with a specific shape and a sensor that allows you to know where its being touched and how intensely. Awesome for all kinds of robotics.
IKEA instructions are usually brilliant, 0 text and yet super easy to understand. One dev took that idea and applied it to algorithms, awesome!
3D render of how a T-Shirt is made
Visualizations are awesome and this one showing how a T-Shirt goes from cotton ball to an actual shirt is fascinating!
AR Glasses Screenshot the World!
I am still waiting for AR contact lenses, and when they arrive things like this will be insanely useful! Using AR you can slice a part of the world and identify what you're looking at. Imagine identifying some random fruit on a deserted island, or some piece in your car to help you fix it.
And if you want to see the Best of the Game Dev Report of 2024 then check this link!
Thank you so much for reading, I really hope you've enjoyed receiving the Game Dev Report every week!
![]() | I love researching and writing this newsletter every week, it's a great way for myself to stay up to date, and I really hope you enjoy reading it as well. I am really glad I started this newsletter and I plan to keep writing it until the end of time. Happy New Year and I wish you a great 2026! |
The year is coming to an end so the Unity Asset Store is running a New Year Sale!
Most of the usual Top Assets are 50% OFF, if you’re looking for recommendations you can watch my Highlights from Black Friday and all of those are on sale.
My own Toolkit asset is on sale! Next year I will be adding tons of Tools and Elements to it and if you pick it up right now you get all of those as FREE Updates!
The Publisher of the Week this time is QAtmo, it’s a publisher with a bunch of 3D models and environments.
Get the FREE Explosive Device C4 & Defuse Kit which is a pretty nice model, perfect for making your own Counter-Strike!
Get it HERE and use coupon QATMO at checkout to get it for FREE!
If you’re interested in realistic environments then there’s a HumbleBundle out right now with a ton of them at an insane 99% OFF discount!
Includes a Carnival, Apocalyptic Hospital, Gothic church, Feudal Japan, Pharaoh theme, Medieval, Elven, etc. Lots of variety to make tons of games!
Get it HERE!
Get Rewards by Sending the Game Dev Report to a friend!
(please don’t try to cheat the system with temp emails, it won’t work, just makes it annoying for me to validate)

Thanks for reading!
Code Monkey
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.
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:
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.
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.
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.
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.
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.
If you're already using Oh My Posh, adding Claude Code integration is as simple as:
claude segmentFor detailed configuration options and all available properties, check out the complete Claude segment documentation.
This integration opens up exciting possibilities. Imagine prompts that:
The foundation is there, and now it's up to the community to build amazing configurations that make AI-powered development even more seamless.