Microsoft
includes Microsoft PowerPoint, Microsoft Excel, Microsoft Windows, Microsoft Azure, Microsoft Office, Microsoft Teams, Microsoft Word, Microsoft Copilot, Microsoft 365, Microsoft Bing, Microsoft CoreAI, Microsoft Outlook
19 statements across 11 episodes · 7 bullish · 5 bearish · 11 people on the record · first statement Dec 21, 2023 by Steve Blank · said 220 times in 35 episodes since 2023 · across every show →
Mentions by year, the whole family
brought up most by Brett Berson (43), Jon Noronha (30), David Cramer (20), Sam Schillace (15), Steve Blank (12), Christopher Payne (12), Jay Parikh (11), Dennis Pilarinos (9)
tap a year for its mentions
2026 75 mentions in 5 episodes 15 per episode
- How Gamma pulled off their AI pivot | Jon Noronha (Co-founder and CPO of Gamma)
- Scaling DoorDash to market dominance | Christopher Payne (Former COO, DoorDash)
- The product wisdom every CPO should ignore | Jeremy Epling (CPO, Vanta)
- The most expensive mistake in outsourcing your tech stack | Jay Parikh (EVP CoreAI, Microsoft)
- Snowflake’s first sales hire on scaling from $0 to $3.5B | Chris Degnan (Former CRO, Snowflake)
- every mention in 2026, scene by scene →
2025 45 mentions in 11 episodes 4 per episode
- How rejecting conventional wisdom grew Sentry to a $3 billion company | David Cramer (Co-founder)
- How to build a company you’ll run forever | Zack Kanter (Founder and CEO of Stedi)
- From reluctant founder to $2B valuation: The story of Persona | Rick Song (Co-founder and CEO)
- What Braintrust got right about product-market fit | Ankur Goyal (Founder and CEO)
- Go hard early: How lessons from Verkada shaped this AI-native IT platform | Jake Stauch (Serval)
- Starting an education giant in a “bad market” | ClassDojo’s story | Sam Chaudhary (Co-founder & CEO)
- From Chrome extension to $5B platform | Postman’s journey | Abhinav Asthana (Co-founder & CEO)
- 1Password’s growth story | How they went from bootstrapped to $6B company | Jeff Shiner (CEO)
- 3 more episodes that year, every mention in 2025 →
2024 76 mentions in 11 episodes 7 per episode
- Developing technical taste: A guide for next-gen engineers | Sam Schillace (Microsoft, Google Docs)
- Building products that delight customers | Adam Nash (Daffy, Wealthfront, LinkedIn, eBay, Apple)
- Essential lessons for building and scaling DevTools | Dennis Pilarinos (Unblocked, Buddybuild)
- Inside Figma’s early days: How to build a world-class sales org | Kyle Parrish (VP of Sales)
- How Figma taps into taste, simplicity, and storytelling | Yuhki Yamashita (CPO)
- The secret lever Replit pulled to scale ahead of its competition | Amjad Masad (Co-founder and CEO)
- The human side of world-class engineering leadership | Michael Lopp (Apple, Palantir, Slack)
- How to find — and keep — product-market fit | Bob Moore (Crossbeam, RJMetrics, Stitch Data)
- 3 more episodes that year, every mention in 2024 →
2023 24 mentions in 8 episodes 3 per episode
- Mastering modern entrepreneurship | Steve Blank (Author of The Four Steps to the Epiphany)
- AI Hot Takes and Unusual Twitter Fundraising Strategies with Dan Siroker (Rewind AI)
- How Vercel found extreme product-market fit by focusing on simplification | Guillermo Rauch (CEO)
- Lessons in leadership | Scaling an org and tactical management advice | Jack Altman (Lattice)
- The business of growing and monetizing an open source product | Ashley Kramer (GitLab CMO/CSO)
- How to leverage intuition, customer support, and raw effort | Colin Zima (Omni & Looker)
- A guide to building product in a post-LLM world | Ryan Glasgow and Kevin Mandich from Sprig
- How to supercharge your engineering org | Kellan Elliott-McCrea (Adobe, Dropbox)
- every mention in 2023, scene by scene →
Everything said about Microsoft, oldest first
Dec 21, 2023 negative
Blank: Ballmer collapsed Microsoft OS share by missing mobile and search
“He basically took Microsoft operating system share from 98% to probably two percent today, right? If you now count mobile devices, right? They're just irrelevant. Because he was so focused on extending the windows ecosystem. They missed mobile. They missed sea…”
Jan 25, 2024 positive
Mar 21, 2024 negative
Mar 21, 2024 negative
Pilarinos: Calling internal big-tech projects 'startups' is disingenuous
“When I was at Microsoft, I remember people had gone and started companies, and I'd be like, oh yeah, I'm doing a startup inside a company, and you're like, that is the most disingenuous thing you can say. I was like, really? If you fail, does your paycheck sto…”
Jun 6, 2024 neutral
Schillace: Microsoft's experimental AI team explores agent mechanics instead of shipping products
“I've got a team right now at Microsoft that's This sort of experimental prototyping team. It's just the whole thing is like a jazz ensemble. It's really wild. We don't really ship products. We're trying to explore the space and understand some deep things abou…”
Jun 6, 2024 neutral
Jun 6, 2024 neutral
Schillace: Microsoft cloud tools must preserve desktop compatibility, unlike Google Docs
“They're trying to keep the cloud very strongly competitive roundtrip, or very strongly compatible, you know, roundtrip compatible with the desktop. That's a design point Google does not care about, but Microsoft does care about.”
Jun 19, 2025 positive
Cramer: Windows is much better than Mac for work these days
“I am a Microsoft loyalist now. And I was like the old school, like hate on windows kind of guy, you know, and now I use windows almost exclusively for like even work. Fortunately, I just don't need to log into certain things, and I love it. Like, I actually th…”
Sep 11, 2025 negative
Sekar: Legacy operations tech point solutions lacked scale to fund R&D
“Most of the technology providers, again, weren't Silicon Valley companies. They weren't even big tech companies like the Microsofts of the world. There were a lot of these point solutions that were building technology for a very specific problem in a very spec…”
Oct 23, 2025 positive
Stauch: Serval supports the entire Microsoft stack via API context
“For us, it's as simple as giving our system context on the Microsoft API, and now we support everything Microsoft. And that architecture decision allows us to just, you know, serve those customers instantly and with very few Hours of development”
Mar 19, 2026 neutral
Epling: Post-acquisition GitHub ran independently on Google tools and AWS
“That company was run very independently. Like, I literally quit Microsoft. Like, your contract ended. It was like, we used all Google tools. Everything was built on AWS. Everything was Zoom. When Satya sent emails to the company, they didn't go to anybody that…”
Mar 19, 2026
Epling: Nat Friedman gave GitHub Actions a strict nine-month GA deadline
“Talked to Nat, and he's like, hey, we've got GitHub Actions, and he was like, you have, like, nine months to get this to GA. And there's like no question of like, could I ask for more time or not? But it's like basically build it and get it to GA in nine month…”
Mar 19, 2026 negative
Epling: Microsoft product teams are disconnected from go-to-market motion
“Like, I feel like there's a lot of great things about Microsoft, but in my experience there, you kind of feel disconnected from the go-to-market motion. Like, it's, it kind of feels like it's on another planet. It's like you're just trying to build the best pr…”
Apr 17, 2026 positive
Payne: Bill Gates's intellectual range made meetings with him terrifying
“Bill Gates is like that. I mean, I used to be terrified to go into a meeting with him because you'd be like, what's he going to ask? I have no idea what he's going to ask. It's going to be, you know, literally you could come in and be talking about, I don't kn…”
Apr 17, 2026 neutral
Jul 24, 2026 positive
Noronha: Gamma mixes multi-provider models while incumbents are tied to in-house models
“We're also able to combine different models from different providers in a way that some of our competitors structurally aren't. They're kind of tied into their own House models, and so we get to directly test, you know, particularly in the world of image model…”
Aug 27, 2026 positive
Parikh demands teams escalate 24-hour blockers directly to him, bypassing managers
“If you get stuck for more than 24 hours in anything that you're doing, you call me, right? Because I don't want this to be like, oh, we have to talk to our manager who talks to their manager who then comes to me two weeks later.”
Aug 27, 2026
Microsoft CoreAI runs manager-free 'brain trusts' of individual contributors
“One of the things that I do at Microsoft is I have these brain trusts. And they're in different parts of our stack, and these brain trusts are formulated with, like, six to eight senior ICs, mid-level ICs only, and no managers, right?”
Aug 27, 2026 positive
Small Microsoft CoreAI teams ship code multiple times per day
“We have teams now in Core AI and Microsoft that, you know, that I support, that I work with, that, Are shipping daily, sometimes multiple times a day, and, you know, some of this stuff is, like, newer products, so they don't have lots of tech debt and whatnot,…”