Microsoft, every mention

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every year anyone Harry Stebbings 480Rory O'Driscoll 98Jason Lemkin 70Tomasz Tunguz 24David Cahn 24Hadi Partovi 21Raz Herzberg 19Howie Liu 19Frank Quattrone 19Kaz Nejatian 16

Verbatim, from the transcripts: the passages where Microsoft comes up

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The Five Year Desert to Product Market Fit & a $5.3BN Valuation with Shiv Rao, Founder @ Abridge · 20VC with Harry Stebbings May 16, 2026 · 1 mention

  • ▶ 1:06:43 Shiv Rao And there was Microsoft and it looked like silos pointing guns at each other.

Anthropic Buys Compute From Elon & Commits $200BN to Google | Cerebras IPO | Ramp Raises at $40BN · 20VC with Harry Stebbings May 14, 2026 · 10 mentions

  • ▶ 14:38 unnamed speaker No more than Microsoft is happy they're doing two hundred billion dollars of revenue with OpenAI. 2 times in the scene
  • ▶ 31:56 unnamed speaker Microsoft in the nineties, they dominated, yeah, they were the operating system, so they dominated broad horizontal, um, off, you know, application software for the consumer and the individual knowledge worker, the office suite. 6 times in the scene
  • ▶ 31:56 unnamed speaker Microsoft in the nineties, they dominated, yeah, they were the operating system, so they dominated broad horizontal, um, off, you know, application software for the consumer and the individual knowledge worker, the office suite. 2 times in the scene

Cliff Weitzman: What I Learned from 100 of the World’s Top CEOs & Why Tokens Will Outspend Salaries · 20VC with Harry Stebbings May 9, 2026 · 1 mention

  • ▶ 1:44:54 Cliff Weitzman Sam and Ilya and Greg and Elon went and got a ton of money from essentially Bill Gates, right, Microsoft.

Anthropic's Raise & What It Means for Potential IPO? Mag7: Google & Amazon Up, Meta & Microsoft Down · 20VC with Harry Stebbings May 7, 2026 · 21 mentions

  • ▶ 0:14 Harry Stebbings Microsoft, eh. 2 times in the scene
  • ▶ 5:45 Rory O'Driscoll It is Microsoft.
  • ▶ 9:01 Rory O'Driscoll I think, and let's kind of play it back to hyperscalers, and let's compare it to Microsoft, who went down after the results. 9 times in the scene
  • ▶ 9:22 Rory O'Driscoll Hey, our co-pilot is so cool that we don't care which LLM we use, and enterprises are just ripping it off the shelves. 2 times in the scene
  • ▶ 14:05 Rory O'Driscoll But if you take out, um, you know, Co-Pilot growth and Azure growth, the rest of the business is flat to slightly down.
  • ▶ 25:24 Harry Stebbings Of the four, Alphabet, Amazon, Meta, ah, and Microsoft, you can buy one and sell one. 5 times in the scene
  • ▶ 29:51 Rory O'Driscoll Yeah, you can sign up something with Entropic and OpenA, you can, you can buy Co-Pilot, or you can buy Co-Work, or you can buy Claude for every one of your employees, and that kind of gets individuals using AI, but doesn't move the needle,…

Inside Clay's Sales Playbook | Becca Lindquist · 20VC with Harry Stebbings May 2, 2026 · 1 mention

Anthropic Raises $45B but Falls Short on Compute & Thoma Bravo Hand Back Medallia Keys to Creditors · 20VC with Harry Stebbings Apr 30, 2026 · 5 mentions

  • ▶ 8:27 unnamed speaker So, so my mental model remains at the three way oligopoly, just like cloud is a three way oligopoly with, you know, Google Cloud, Amazon and Azure, right?
  • ▶ 22:26 unnamed speaker Microsoft had to hire no one when they exploded in revenue.
  • ▶ 28:02 unnamed speaker Microsoft, CoreWeaver, Oracle will actually, quote, have the compute.
  • ▶ 29:20 Jason Lemkin So they have all this capacity for themselves that they can allocate even better than Microsoft. 2 times in the scene

Replit CEO: Why the SaaS Apocalypse is Justified & Why Coding Models are Plateauing | Amjad Masad · 20VC with Harry Stebbings Apr 25, 2026 · 1 mention

Cursor Acquired for $60BN | Anthropic Hits $1TRN in Secondary Markets & Figma, Adobe, Canva Dead? · 20VC with Harry Stebbings Apr 23, 2026 · 7 mentions

  • ▶ 23:13 Jason Lemkin NVIDIA, Apple, Meta, Amazon, Alphabet, Microsoft all can buy a startup for a hundred billion. 2 times in the scene
  • ▶ 1:00:54 Rory O'Driscoll It was email, you know, and effectively a docs and a spreadsheet, which just gnawed away at the bottom end of the Microsoft Office Suite. 2 times in the scene
  • ▶ 1:01:12 Rory O'Driscoll Yanking Microsoft's chain on a forty billion dollar business.
  • ▶ 1:26:19 Jason Lemkin Of course, just like, it's a bad analogy, but just like in the end, Google, Microsoft, et al, were well placed for, for the last generation of AI.
  • ▶ 1:41:24 Rory O'Driscoll Is it just a competitive trading, you know, partners, competitor in the way that Microsoft and Apple compete?

Aaron Levie: Everyone is Wrong; We'll Have More Developers in 5 Years · 20VC with Harry Stebbings Apr 20, 2026 · 2 mentions

  • ▶ 48:00 Aaron Levie Azure had just launched, and GP, and GCP was called Google App Engine, and it had a little, like, a turbine logo, uh, with, like, wings or something. 2 times in the scene

SpaceX's Financials Leaked: Is it Worth $2TN | Meta Debuts Muse Spark: Are They Back in the AI Race? · 20VC with Harry Stebbings Apr 16, 2026 · 6 mentions

  • ▶ 59:23 unnamed speaker If you are correct, and I'm not sure you are, what it says is the people who should go into guidance counseling are Microsoft and OpenAI, because they need to get their relationship back together again, because who is the dominant part to… 4 times in the scene
  • ▶ 1:26:00 unnamed speaker Again, back to the same therapist that they're using for their relationship with Microsoft could actually do some internal relationships too. 2 times in the scene

The Early Days of Anthropic & How 21 of 22 VCs Rejected It | The Four Bottlenecks in AI | Anj Midha · 20VC with Harry Stebbings Apr 14, 2026 · 4 mentions

  • ▶ 12:40 Anjney Midha Because the context, the mission-critical context of those workloads is so important to be run locally that you can't run them on Amazon, AWS, GCP, or Azure, and it's the first time
  • ▶ 18:29 Anjney Midha This was very legible to Amazon because they were watching what was happening with Azure and open AI.
  • ▶ 55:57 Anjney Midha But there's a reason why, you know, Anthropic also has a thing called Cloud Code, and there's all, there's a reason why Mistral has something called Mistral Compute, and there's something called, there's a, there's a reason why, you know,…
  • ▶ 55:57 Anjney Midha But there's a reason why, you know, Anthropic also has a thing called Cloud Code, and there's all, there's a reason why Mistral has something called Mistral Compute, and there's something called, there's a, there's a reason why, you know,…

OpenAI Buys TBPN & Their Management Team Reboot | Mercor Hack & Why Now is the Time for Cyber · 20VC with Harry Stebbings Apr 9, 2026 · 2 mentions

  • ▶ 8:42 unnamed speaker And again, I mean, look, Antropic does some of the same stuff in the sense of, given that your biggest expenses are, you know, compute and then distribution, you know, from Microsoft on with OpenAI to all the recent Antropic deals, there's…
  • ▶ 32:30 unnamed speaker You know, the top four or five, Nvidia, Apple, Microsoft, Alphabet, and I think Meta is, you know, approximately 30% of the total S&P, right?

OpenAI Kills Sora & Hits $100M ARR on Ads | Oura Going Public & Whoop Raises at $10BN · 20VC with Harry Stebbings Apr 2, 2026 · 5 mentions

  • ▶ 25:09 unnamed speaker The change in the paradigm is good for everybody except, you know, Windows Defender from 1996. 2 times in the scene
  • ▶ 30:41 unnamed speaker And what they're saying there is if OpenAI sells through Microsoft and Microsoft takes some money off the top, OpenAI only reports the net amount. 2 times in the scene
  • ▶ 1:11:22 unnamed speaker Microsoft, same thing, right?

Marc Andreessen: Will a16z Go Public & Why Labour Displacement with AI is Wrong? · 20VC with Harry Stebbings Mar 30, 2026 · 1 mention

  • ▶ 57:29 Marc Andreessen Um, but by the way, the free ones are pretty good now, and by the way, Google gives away a lot of AI value for free, and Microsoft is starting to do that, and others, others are doing that as well.

Why Margins Don't Matter for Early-Stage Startups | Gili Raanan · 20VC with Harry Stebbings Mar 28, 2026 · 1 mention

  • ▶ 22:57 Gili Raanan And, you know, think about the bank that's using an island browser instead of, uh, Google or Microsoft browsers.

Why You Need a $1B Fund To Do Series A | SpaceX at $2TRN & Data Centers in Space | Groq's $20BN Deal · 20VC with Harry Stebbings Mar 26, 2026 · 3 mentions

  • ▶ 40:57 Harry Stebbings And I was like, fuck, if, if Sequoia and Azure are buying thirty-five million bucks, I'll put in some of my money.
  • ▶ 57:48 unnamed speaker Well, obviously the market rejected Microsoft co-pilot products as things they didn't want to pay more for, right?
  • ▶ 1:10:35 unnamed speaker Microsoft is not buying a hundred companies.

Gokul Rajaram: How to Analyse for Durability and Defensibility in a World of AI · 20VC with Harry Stebbings Mar 16, 2026 · 4 mentions

  • ▶ 38:33 Gokul Rajaram You would never assume, why would you ever buy a PowerPoint thing or a presentation thing separately?
  • ▶ 38:51 Gokul Rajaram As you know, Microsoft tried to crush Intuit again and again and again, back in the eighties and nineties with bundling everything into office, but Intuit TurboTax survived and thrived.
  • ▶ 38:51 Gokul Rajaram As you know, Microsoft tried to crush Intuit again and again and again, back in the eighties and nineties with bundling everything into office, but Intuit TurboTax survived and thrived.
  • ▶ 39:26 Gokul Rajaram I don't know why Gamma would not create a, just like they've, they've taken their riff on PowerPoint, why can't they have their own take on documents or slides the same way?

Elena Verna: How Lovable Launches Product & Hacks Social to Go Viral · 20VC with Harry Stebbings Mar 14, 2026 · 1 mention

  • ▶ 16:46 Elena Verna And then in order to solve for that, companies start going after tooling and they start creating these community platforms and forums, basically trying to almost replicate what Microsoft has created or like another like core, so to speak.

Anthropic vs The Pentagon: Who Wins? | The Data Center Arms Race | The Ultimate Stock Picks · 20VC with Harry Stebbings Mar 12, 2026 · 5 mentions

  • ▶ 3:23 Rory O'Driscoll There was one version that said, if you use Antropic at all, Microsoft or Amazon, then we won't use you at all in the US government. 2 times in the scene
  • ▶ 23:47 Rory O'Driscoll Google actually has a business, and Microsoft is quietly stepping back from the table.
  • ▶ 54:00 Rory O'Driscoll I mean, you know, Microsoft and Google are all going at 13, right?
  • ▶ 1:13:39 Rory O'Driscoll The other two are early teens EBITDA, which is roughly the same as Microsoft and Google, pretty boring, right?

"Cursor is Dead" is Total BS: Here is Why | Miles Clements · 20VC with Harry Stebbings Mar 9, 2026 · 1 mention

  • ▶ 37:16 Miles Clements Google, and Microsoft, and Amazon, then of course you want to participate in those companies in the private markets.

Mitchell Green: Why 50% of VCs Should Not Exist · 20VC with Harry Stebbings Mar 7, 2026 · 4 mentions

  • ▶ 8:38 Mitchell Green Or is Google, Microsoft, and Meta right?
  • ▶ 16:55 Mitchell Green Microsoft is a legacy software company.
  • ▶ 36:51 Mitchell Green Um, right, and look how much earnings a company like Facebook and Google and Microsoft and Amazon and Nvidia generate, like, profits.
  • ▶ 50:46 Mitchell Green Because you have the big public companies, like, being like, oh, Microsoft telling people, like, oh, this company's going to go out of business.

Anthropic vs The Pentagon: Who Wins? | OpenAI's $110BN Mega Round | Cursor Hits $2BN in ARR · 20VC with Harry Stebbings Mar 5, 2026 · 5 mentions

  • ▶ 1:11:02 unnamed speaker I mean, all you have to do is look at Azure's market share in cloud, where for 20 years, the value proposition, having said in millions of board, not millions, but tens of board meetings where we've talked about, you know, we're running on… 3 times in the scene
  • ▶ 1:11:18 unnamed speaker And the value proposition of Agile for 20 years was it's not nearly as, it's not as good, but it's getting there, and Microsoft have great relationships with every CTO, so it'll be fine.
  • ▶ 1:20:12 unnamed speaker Obviously it turns out Microsoft stock is holding up pretty well.

Monday.com CEO on Is SaaS Dead: Will Everything Be Vibe Coded | Eran Zinman · 20VC with Harry Stebbings Mar 2, 2026 · 4 mentions

Insights from Coatue's Growth Investor Lucas Swisher · 20VC with Harry Stebbings Feb 23, 2026 · 3 mentions

  • ▶ 25:48 Lucas Swisher The largest SaaS company in the world that's independent outside of Microsoft and the hyperscalers, Salesforce, right?
  • ▶ 48:19 Lucas Swisher Being able to express a company in a few, a complex company in a few lines in Excel and tell stories with data is like an incredible skill.
  • ▶ 50:03 Lucas Swisher Live in Excel all day, and you are like just missing the forest through the trees.

OpenAI's Codex Lead: Why Coding as We Know It is Over · 20VC with Harry Stebbings Feb 21, 2026 · 3 mentions

  • ▶ 7:55 Harry Stebbings That's where I think, like, Claude has done well in terms of the packaging they've done, like Claude for legal, Claude for Excel, where you can implement it and have a DCF model.
  • ▶ 43:24 Harry Stebbings And like the majority of the market will be on Codex or Claude Code, or is it like a AWS, Azure, Google Cloud, and a 33, 33, 33?
  • ▶ 1:01:05 Alexander Emberikos For instance, there's none that exists on Windows.

Thrive Raises New $10B Fund | OpenAI Buys OpenClaw | Stripe at $140B: Is Adyen Wildly Undervalued? · 20VC with Harry Stebbings Feb 19, 2026 · 4 mentions

  • ▶ 6:43 Rory O'Driscoll I went back and plowed through the early Microsoft, the early Google, the early compact. 3 times in the scene
  • ▶ 8:35 Rory O'Driscoll These companies aren't like, you know, aren't like the explosive growth of internet companies or software companies like Microsoft because they are wildly capital intensive.

Anthropic's Super Bowl Ad: Who Won & Lost? | Sierra Hits $150M ARR: Is Customer Support Too Crowded? · 20VC with Harry Stebbings Feb 12, 2026 · 6 mentions

  • ▶ 1:56 Rory O'Driscoll If you don't believe in TAM expansion and it's a zero sum game, then if two companies are going to do four hundred billion, then we can probably assume Microsoft, who's already at two hundred billion, going to roll over and die. 4 times in the scene
  • ▶ 1:09:55 Mike Cannon-Brookes Microsoft has to do it. 2 times in the scene

a16z, Anish Acharya: Is SaaS Dead? Do Margins Still Matter? Why We Are Not in an AI Bubble? · 20VC with Harry Stebbings Feb 9, 2026 · 2 mentions

  • ▶ 8:34 Anish Acharya So Microsoft will make a better word processor than they've ever made.
  • ▶ 15:07 Anish Acharya Word and Docs and Spreadsheet and all of these other products around that core primitive, does OpenAI have the sort of prioritization, the resources, and the ambition in that direction to build all the feature surface around the primitive?

20VC: From $6.2BN Market Cap to $2.8BN: What Is Not Translating About Navan's Public Story | Are Any Public Company CEOs Actually Happy? | Why Navan Built It's Own Customer Service AI and What it Could Mean For Customer Service AI with Ariel Cohen Feb 7, 2026 · 1 mention

  • ▶ 26:50 Ariel Cohen To I need to create a development platform here, which is kind of in a way similar to what Microsoft did, you know, in the nineties.

The SaaS Massacre: Public Market Collapse |Microsoft Lost $360B & NVIDIA’s $100B Dispute with OpenAI Feb 5, 2026 · 20 mentions

  • ▶ 12:38 unnamed speaker I mean, Microsoft said the same thing on their investor call.
  • ▶ 48:10 Harry Stebbings Um, anyway, Microsoft's second largest market cap loss ever. 13 times in the scene
  • ▶ 48:33 unnamed speaker Maybe miss Azure growth by one percent, 37 versus 38, all within a margin of error. 5 times in the scene
  • ▶ 58:29 Jason Lemkin I mean, Microsoft bailed them out for years, but if NVIDIA can afford it, it has to, it has to bail them out.

Oren Zeev: Why AI Growth Expectations Are BS & Won't Last? Why GPs Shouldn't Tell LPs Their Strategy Feb 2, 2026 · 2 mentions

  • ▶ 1:09:22 unnamed speaker Wiz is an interesting story because when I heard that, um, uh, I didn't know what stuff, but when I heard that he was, uh, leaving Microsoft, I didn't even know he was starting a company. 2 times in the scene

Anthropic Inference Costs Skyrocket |TikTok Deal Closes |The IPO Market:Wealthfront & EquipmentShare · 20VC with Harry Stebbings Jan 29, 2026 · 1 mention

  • ▶ 18:29 Rory O'Driscoll They cleaned it up for 12 to 24 months and then sold it to Microsoft and made three times the money on a ton of money on their first fund, so super shrewd that was.

Legora CEO, Max Junestrand: $7M ARR in a Day | Harvey vs Legora: Is a Legal AI Winner Takes All? · 20VC with Harry Stebbings Jan 26, 2026 · 7 mentions

Elon Musk vs Sam Altman | The Implosion of Thinking Machines | Can VC Survive Public Pricing? · 20VC with Harry Stebbings Jan 22, 2026 · 3 mentions

Harvey CEO Winston Weinberg: How to Make Mega Deals | Lessons from Rabois, Halligan & Grady · 20VC with Harry Stebbings Jan 19, 2026 · 4 mentions

Anthropic’s $10B Raise | a16z’s $15B Fund: Is the Middle Dead in VC? | How OpenAI Could Go to Zero? · 20VC with Harry Stebbings Jan 15, 2026 · 17 mentions

  • ▶ 7:19 unnamed speaker The idea is, is that if you're building PowerPoint, if you're. 3 times in the scene
  • ▶ 7:24 unnamed speaker If you're doing all the other knowledge work that those of us who aren't coders do, instead of bringing the AI to the Excel spreadsheet, which is what Copilot tried to do with Microsoft, you bring all these tools into the cloud space, into… 4 times in the scene
  • ▶ 7:24 unnamed speaker If you're doing all the other knowledge work that those of us who aren't coders do, instead of bringing the AI to the Excel spreadsheet, which is what Copilot tried to do with Microsoft, you bring all these tools into the cloud space, into…
  • ▶ 7:24 unnamed speaker If you're doing all the other knowledge work that those of us who aren't coders do, instead of bringing the AI to the Excel spreadsheet, which is what Copilot tried to do with Microsoft, you bring all these tools into the cloud space, into… 2 times in the scene
  • ▶ 8:14 unnamed speaker Every single knowledge worker uses the office suite. 2 times in the scene
  • ▶ 8:16 unnamed speaker You get PowerPoint, you get Excel, you get Word, right?
  • ▶ 17:27 unnamed speaker The second largest loser is Microsoft will survive.
  • ▶ 1:08:54 unnamed speaker And that's a lot, you know, I mean, the office windows offices, I used to know the 50, sixty billion, but, um, yeah, it's a, it's a big flood of revenue.
  • ▶ 1:08:54 unnamed speaker And that's a lot, you know, I mean, the office windows offices, I used to know the 50, sixty billion, but, um, yeah, it's a, it's a big flood of revenue.
  • ▶ 1:30:20 unnamed speaker I've decided after 27 years at Microsoft, I've decided January 15th is my last day.

Alex Rampell: The Best Founders Materialise Capital, Customers & Labour | The Future of Venture · 20VC with Harry Stebbings Jan 12, 2026 · 3 mentions

  • ▶ 25:54 Alex Rampell So, you know, you go back, like the infrastructure layer for PCs was, I don't know, like Microsoft and Apple, like the operating system players, the infrastructure player for the internet was like Cisco and Akamai. 2 times in the scene
  • ▶ 52:56 Alex Rampell It's called Microsoft Office, right?
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