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Microsoft

includes Microsoft Excel, Microsoft Azure, Microsoft PowerPoint, Microsoft Word, Microsoft Outlook, Microsoft Office, Microsoft Copilot, Microsoft Windows, Microsoft Teams, Microsoft Bing, Microsoft 365, Microsoft Research and 18 more

175 statements across 124 episodes · 74 bullish · 49 bearish · 93 people on the record · first statement Mar 12, 2015 by Harry Stebbings · said 2,014 times in 508 episodes since 2015 · across every show →

Mentions by year, the whole family

brought up most by Harry Stebbings (480), Rory O'Driscoll (98), Jason Lemkin (70), Tomasz Tunguz (24), David Cahn (24), Hadi Partovi (21), Raz Herzberg (19), Howie Liu (19)

tap a year for its mentions
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050100201520162017201820192020202120222023202420252026episodes it came up in
004508100201520162017201820192020202120222023202420252026episodesmentions per episode
2026 364 mentions in 81 episodes 4 per episode
2025 572 mentions in 95 episodes 6 per episode
2024 313 mentions in 75 episodes 4 per episode
2023 181 mentions in 48 episodes 4 per episode
2022 103 mentions in 42 episodes 2 per episode
2021 74 mentions in 29 episodes 3 per episode
2020 96 mentions in 29 episodes 3 per episode
2019 41 mentions in 21 episodes 2 per episode
2018 49 mentions in 18 episodes 3 per episode
2017 103 mentions in 32 episodes 3 per episode
2016 49 mentions in 22 episodes 2 per episode
2015 69 mentions in 16 episodes 4 per episode

every mention, scene by scene, with the transcript →

Everything said about Microsoft, oldest first

Mar 12, 2015
Assertion Supported
Microsoft acquired calendar app Sunrise.am for $100 million
“Sunrise.am, which was recently acquired for a hundred million by Microsoft.”
Harry Stebbings Mar 12, 2015 ▶ 0:27 20 VC 019: Funding the Future with James Wise of Balderton Capital
Aug 14, 2015 neutral
Disclosure
Valade: Sunrise sold to Microsoft because the team couldn't monetize it
“I think we didn't know exactly how we could take it from a great product to a great business. I think we've done a good job building a great product. We didn't really know how we could make money. Or turn it into, and turn this into a successful business. And …”
Pierre Valade Aug 14, 2015 ▶ 15:55 FF 08: Pierre Valade, CEO @ Sunrise on Being Acquired By Microsoft for $100m and Building Beautiful Products
Aug 14, 2015 neutral
Disclosure
Valade: Some Sunrise investors wanted to reject Microsoft's $100M offer
“Yeah, so this, so some of them thought that we should go for more, but I also think investors who really respect entrepreneurs, And, ah, and I think those investor that we worked with respect the entrepreneur decision at the end of the day.”
Pierre Valade Aug 14, 2015 ▶ 17:27 FF 08: Pierre Valade, CEO @ Sunrise on Being Acquired By Microsoft for $100m and Building Beautiful Products
Aug 14, 2015 positive
Disclosure
Valade: Microsoft Paid the Acquisition Price Sunrise Asked For
“You just, you know, for us, you know, we knew that we had a price, and we got the price we wanted, and the vision were aligned, and we liked the people we met there, so, you know, we said, okay, you know, we should do it.”
Pierre Valade Aug 14, 2015 ▶ 17:05 FF 08: Pierre Valade, CEO @ Sunrise on Being Acquired By Microsoft for $100m and Building Beautiful Products
Sep 6, 2015 positive
Disclosure
Accompli had millions in enterprise pipeline before Microsoft acquisition
“At the time, We were very, very, very fortunate to already have, like, multiple millions of dollars of sales pipeline, and customers actually two in Europe, one in the UK, and two in the US, who were working with us very closely to really sign up and craft wha…”
Javier Soltero Sep 6, 2015 ▶ 22:39 FF 012: Acquired by Microsoft for $200m with Javier Soltero @ Microsoft
Sep 6, 2015
Assertion Supported
Microsoft Acquired Accompli for $200 Million in 2014
“Prior to Microsoft, Javier co-founded Accompli, the mobile personal information manager acquired by Microsoft for two hundred million dollars in 2014.”
Harry Stebbings Sep 6, 2015 ▶ 0:13 FF 012: Acquired by Microsoft for $200m with Javier Soltero @ Microsoft
Sep 6, 2015 bullish
Prediction Not checkable as stated
Soltero: Microsoft will modernize email into a beloved medium within five years
“Over the next five years, we're here to make email awesome, and really take this incredibly powerful and pervasive medium that, that we often sort of complain about and hate and really turn it into something that people genuinely love and feel like it has adap…”
Javier Soltero Sep 6, 2015 ▶ 28:59 FF 012: Acquired by Microsoft for $200m with Javier Soltero @ Microsoft
Sep 9, 2015 neutral
Assertion Supported
Ver Ploeg: Microsoft went public at a sub-$1B market cap
“I mean, people like to talk about how when Microsoft went public, it was a sub one billion dollar market cap company.”
Eric Ver Ploeg Sep 9, 2015 ▶ 18:44 20 VC 070: Do Investors in California Outperform The Rest of The World with Eric ver Ploeg @ Recursive Capital
Oct 9, 2015 bullish
Prediction Held up
Wunderlist will become Microsoft's core task layer and spread its startup culture
“Ah, so for me and Wunderlist, it is integrate deeply into, to Microsoft, be the layer that connects things in terms of tasks, things you need to get done, and continue to both learn from one of the largest, most important technology organizations ever, but als…”
Chad Fowler Oct 9, 2015 ▶ 24:15 FF 016: Chad Fowler, CTO @ Wunderlist, App Of The Year 2013
Oct 9, 2015 positive
Assertion Not checkable as stated
Wunderlist maintained complete operational autonomy in Berlin after Microsoft acquisition
“Really nothing has changed. We're operating in Berlin. We're a solid team making decisions the same way we did before. Like I said, we, you know, we have freedom to do things exactly as we did in the past, but we have more help when we need it.”
Chad Fowler Oct 9, 2015 ▶ 20:16 FF 016: Chad Fowler, CTO @ Wunderlist, App Of The Year 2013
Mar 16, 2016 bullish
Prediction Not checkable as stated
O'Leary: Great European startups will always be acquired by global capital
“No, because the capital is global, highly mobile. The biggest occurs in Europe are Google, Microsoft, SAP, and I don't care. And now Chinese companies Chinese companies, Japanese companies, I think that that makes it less of a problem. So big companies will be…”
Ciaran O'Leary Mar 16, 2016 ▶ 21:04 20VC: The Three Fundamental Forces in Society with Ciaran O'Leary, Partner @ BlueYard
Sep 2, 2016 bullish
Prediction Not checkable as stated
Minshew: Microsoft acquiring LinkedIn opens competitive room for The Muse
“I think that, that the Microsoft acquisition does have Shareholder value, and there's some interesting synergies, but if anything, I believe it will pull LinkedIn a direction that opens up even more space for us to really focus on the experience of an individu…”
Kathryn Minshew Sep 2, 2016 ▶ 25:12 20VC: How To Win The Strategic Process Of Fundraising and Optimising Co-Founder Relationships and Break Ups with Kathryn Minshew, Founder & CEO @ The Muse
Jan 23, 2017 bearish
Opinion
Lilly: Microsoft has completely lost its software distribution advantage
“Microsoft has completely lost the distribution advantage, because people don't really create as much as a higher percentage of their material anymore on, on Windows machines.”
John Lilly Jan 23, 2017 ▶ 14:50 20VC: Greylock's John Lilly on How Greylock Continues To Invest In The Next Big Markets, The Importance Of Building Tribes & Why There will Be Another Boom In Mobile
Feb 20, 2017
What-if
Nozad missed massive returns by not maintaining pro-rata ownership in Danger
“Had we participated and kept our ownership after the initial investment, we would have made a lot of money through a half a billion dollar acquisition of Danger by Microsoft.”
Pejman Nozad Feb 20, 2017 ▶ 16:54 20VC: Pejman Nozad: Tech's Most Unlikely VC: From Yoghurt Shop To Investing In Startups Now Worth $20Bn+
May 10, 2017
Assertion Contradicted
Wolfe: Kymeta is the only board Bill Gates joined besides Berkshire and Microsoft
“It's the only company that Bill Was on the board of besides Berkshire Hathaway and Microsoft.”
Josh Wolfe May 10, 2017 ▶ 11:54 20VC: The 3 Forms Of Edge A Founder Can Have, Lessons From Being on A Board With Bill Gates & Why There Are A Lot Of Tourist VCs Who Are Going To Lose A Lot Of Money, with Josh Wolfe, Co-Founder @ Lux Capital
Nov 1, 2017 neutral
Assertion Supported
Buchheit: Microsoft's first product targeted only a few thousand potential customers
“Microsoft's first product was Altair Basic, which was a little basic interpreter for, or compiler for this computer called the Altair that had probably several hundred or maybe thousand possible customers.”
Paul Buchheit Nov 1, 2017 ▶ 6:31 20VC: Y Combinator's Paul Buchheit on Creating Gmail Version 1.0 & Leadership Lessons from Working With Zuckerberg and Larry Paige
Jan 10, 2018 negative
Disclosure
Every infrastructure startup pitches something Amazon, Microsoft, or Google could build
“Every pitch that I hear about infrastructure is ostensibly something that Amazon could do one day, right? Or Microsoft or Google”
Crystal Huang Jan 10, 2018 ▶ 20:56 20VC: 3 Key Differences Between US and Asian Tech Markets & With Such Large Incumbents Chasing Early Acquisitions, Is There A Market For Later Stage VC with Crystal Huang, Investor @ GGV Capital
Mar 23, 2018 positive
Disclosure
Dan Lewis says Amazon influenced Convoy's culture more than Google
“I think the one that certainly influenced me the most, primarily because I was doing it right before I started Convoy, was Amazon.”
Dan Lewis Mar 23, 2018 ▶ 4:33 20VC: How To Strategically Build The Right Investor Base, Why Startup Timing is Like Surfing & How To Determine Whether Someone is Scaling with the Organisation or Not with Daniel Lewis, Founder & CEO @ Convoy
Apr 20, 2018 positive
Opinion
Zappacosta: Forming a founding team before finding an idea is valid
“So we kind of did what you're not supposed to do, which is decide to start a business and then go hunt for an idea. However, I think that actually gets a very bad rap here in the And it's a very tried and true method. You know, Amazon did that. Microsoft did t…”
Marco Zappacosta Apr 20, 2018 ▶ 3:22 20VC: Thumbtack's Marco Zappacosta on The 3 Core Elements To All Board Meetings, Raising $250m from Sequoia and Why You Have To Win Supply Side Acquisition First For Marketplace Success
Jul 20, 2018
Assertion Not checkable as stated
Gates and Ballmer initially saw Linux as a bigger threat than Google
“We had done the early work that got Gates and Bomber focused on Google as a threat to the business, and at the time, back then, they were more focused on the enterprise side and on the threat that Linux kind of represented, and so we had gotten the company pre…”
Fritz Lanman Jul 20, 2018 ▶ 14:07 20VC: ClassPass CEO Fritz Lanman on Betting His Career Facebook Would Be A $10Bn Company, Lessons From Travis and Uber on Scaling A Global Marketplace & Whether Growth and Capital Efficiency Are Mutually Exclusive
Jul 20, 2018 positive
Disclosure
Steve Ballmer asked Lanman to bet his career on Facebook's $10B valuation
“I remember Steve Ballmer asked me if I'd bet my career on Facebook being worth ten billion, which is what my team and I had kind of come up with, and we didn't have much downside, so we were willing to take the bet”
Fritz Lanman Jul 20, 2018 ▶ 15:33 20VC: ClassPass CEO Fritz Lanman on Betting His Career Facebook Would Be A $10Bn Company, Lessons From Travis and Uber on Scaling A Global Marketplace & Whether Growth and Capital Efficiency Are Mutually Exclusive
Sep 14, 2018
Insight
Lerman: History's Greatest Companies Are Built Organically Bottom-Up
“I will say that I think if you historically look back at the greatest companies in history, they typically have come from more of a grassroots organic type of feel like Microsoft or Apple or even IBM or going back to the Ford Motor Company, going back eons ago…”
Howard Lerman Sep 14, 2018 ▶ 5:03 20VC: Behind The Scenes of a $Bn IPO Process, What Startups Can Learn From Teddy Roosevelt's "Five Minute Meetings" and What John Lennon Teaches Founders About Storytelling with Howard Lerman, Founder & CEO @ Yext
Dec 3, 2018 bullish
Assertion Not checkable as stated
Danny Rimer: Enterprise Software Is Adopting Consumer Selling Metaphors
“So whether it's Dropbox, or Slack, or the Microsoft, the three, six, five efforts, or what Adobe is magnificently doing, a lot of the enterprise is actually moving towards the consumer metaphor to sell software.”
Danny Rimer Dec 3, 2018 ▶ 7:36 20VC: Index's Danny Rimer on His Biggest Lessons On Price, Ownership, Board Dynamics & Building Consumer Businesses from Backing The Likes of King, Skype, Farfetch, Glossier and more...
May 10, 2019
Assertion Partly supported
Romanow: Bill Gates Owned 50% of Microsoft at IPO
“When Microsoft went public, Bill Gates owned half of that company”
Michele Romanow May 10, 2019 ▶ 16:08 20VC: Clearbanc's Michele Romanow on Why 40% of VC $ Raised Today Goes To Google and Facebook, How To Create A Financing Mechanism For The Repeatable Parts Of Your Business & Why We Need To Stop Celebrating Fundraises
Jul 8, 2019 bullish
Assertion Supported
Microsoft is aggressively gaining market share in enterprise public cloud
“They are several years into this transition and as Microsoft generally does, they're doing a great job of being a fast follower. And are very aggressively gaining share and making strides on the enterprise segment of public cloud specifically.”
Byron Deeter Jul 8, 2019 ▶ 8:13 20VC: Bessemer's Byron Deeter On Lessons From Investing in 14 $Bn Companies, What The Heck Is Going On In Cloud Today and Why Cloud IPO Floodgates Are About To Burst Open
Jul 22, 2019
Insight
Beyroutey: Startups compete with Big Tech by attacking niche flanks
“I think that that's fair in a whole host of markets, and so I think of that as a strong default, and I might compare that sentiment to the strong defaults in the nineties and early 2000 that you can't compete with Microsoft. And that's a strong default because…”
Jesse Beyroutey Jul 22, 2019 ▶ 8:54 20VC: IA Ventures' Jesse Beyroutey on Game Theory and How It Impacts Investor Mindset, How To Avoid "The Pressure To Deploy" Today In Venture & Why Ownership Is The Single Most Important Parameter When Investing
Oct 28, 2019
Assertion Not checkable as stated
Steve Ballmer's executive presence won Microsoft the early cloud battle against Google
“But, you know, in the early days of that battle, when they had way better product, Google had a way better product, Balmer would, and Balmer's still CEO at the time, would show up in companies and say, I'm here. Is Larry Page going to come visit? And of course…”
Ben Horowitz Oct 28, 2019 ▶ 15:51 20VC: a16z's Ben Horowitz on How To Create An Environment of Trust with Founders, How and Why Creating Shocking Rules Is So Impactful To Culture & What The Samurai, Shaka Senghor and Toussaint Teach Us About Company Culture Building
Aug 31, 2020 neutral
Assertion Supported
Hartz: Microsoft and Amazon both IPO'd at $500M valuations
“If you look back at Microsoft in the 19 eighties or Amazon in the 19 nineties, one would maybe not recall that they went public at a five hundred million dollar valuation each”
Kevin Hartz Aug 31, 2020 ▶ 10:49 20VC: SPACs. What Are They? Why Now? How Do They Change The Venture Landscape? Are They Better Than IPOs & Direct Listings? How Should Founders Think About Them? Kevin Hartz & Troy Steckenrider @ A*
Dec 7, 2020 positive
Disclosure
Satya Nadella allows Reid Hoffman to meet freely across Microsoft teams
“Satya feels perfectly comfortable having me meet with, like, everybody, like, people in company, product groups, and everything else, because he knows that I'm actually, in fact, very capable of giving that kind of advice and listening and so forth, without sa…”
Reid Hoffman Dec 7, 2020 ▶ 9:43 20VC: Reid Hoffman on Investing in Airbnb and Passing on Stripe, The Different Styles of Truly Great Leaders, How To Think Through Ownership and Price in Venture & How To Ensure Venture Partnerships Always Have Trust and a Learning Mindset
Dec 28, 2020
Assertion Not checkable as stated
Clark: Winning a debate against Bill Gates was a Microsoft rite of passage
“And it was a rite of passage to be in a conference room with Bill and in a debate with him and win a point. Like, just to win a debate, right, was this major rite of passage.”
Quentin Clark Dec 28, 2020 ▶ 5:15 20VC: Lessons From Working with Bill Gates, How To Lead Without Authority and The Difference Between Leadership and Management & How Fundraising Changes In A COVID World with Quentin Clark, Managing Director @ General Catalyst
Dec 28, 2020 negative
Opinion
Clark: Microsoft's culture was insular and disconnected before Satya Nadella
“Microsoft before Satya was a little insular. Like, we're up there in the woods in Seattle, and we didn't really kind of get down to the valley very much, right?”
Quentin Clark Dec 28, 2020 ▶ 3:22 20VC: Lessons From Working with Bill Gates, How To Lead Without Authority and The Difference Between Leadership and Management & How Fundraising Changes In A COVID World with Quentin Clark, Managing Director @ General Catalyst
Feb 15, 2021 negative
Assertion Contradicted
Reber: Wunderlist ceased to exist three years post-acquisition
“So, like, Wanderlust is a very good example, right? After selling it three years later, it doesn't exist anymore.”
Christian Reber Feb 15, 2021 ▶ 7:50 20VC: Wunderlist & Pitch Founder, Christian Reber on His Personal Relationship with Risk, Money, Whether the Sale to Microsoft was a Mistake, What Great Product Designs Means Today & Why Founders Investing External Capital is a Distraction
Feb 15, 2021
Assertion Contradicted
Reber: Real-Time Sync Was the Primary Reason Microsoft Bought Wunderlist
“And it actually, in the end, it was the reason Microsoft bought us, because of the real-time synchronization we've had.”
Christian Reber Feb 15, 2021 ▶ 26:21 20VC: Wunderlist & Pitch Founder, Christian Reber on His Personal Relationship with Risk, Money, Whether the Sale to Microsoft was a Mistake, What Great Product Designs Means Today & Why Founders Investing External Capital is a Distraction
Feb 15, 2021 negative
Disclosure
Reber: Selling Wunderlist to Microsoft felt like selling to the enemy
“When I sold Wanderlust, it felt like I'm selling my child to the enemy. I didn't want to get bought by Microsoft. I viewed Microsoft as the enemy, and it was just stupid.”
Christian Reber Feb 15, 2021 ▶ 21:50 20VC: Wunderlist & Pitch Founder, Christian Reber on His Personal Relationship with Risk, Money, Whether the Sale to Microsoft was a Mistake, What Great Product Designs Means Today & Why Founders Investing External Capital is a Distraction
Feb 15, 2021 negative
Opinion
Reber: Microsoft screwed up its acquisitions of Yammer, Skype, and Wunderlist
“I think Microsoft has Screwed up multiple acquisitions like Yammer or Skype, and they promised me when we sold it that they will try their very best not to screw up Wunderlist, and I think they did.”
Christian Reber Feb 15, 2021 ▶ 10:23 20VC: Wunderlist & Pitch Founder, Christian Reber on His Personal Relationship with Risk, Money, Whether the Sale to Microsoft was a Mistake, What Great Product Designs Means Today & Why Founders Investing External Capital is a Distraction
Apr 26, 2021 positive
Assertion Not checkable as stated
Conrad: Most massive tech outcomes are compound startups with broad portfolios
“If you look at the really big outcomes, most of them end up being compound companies. You look at Microsoft, Salesforce, those are all companies that succeed because they have this broad product portfolio, and because of the ways that all of these products int…”
Parker Conrad Apr 26, 2021 ▶ 10:58 20VC: Rippling's Parker Conrad on Why The VC/Founder Marriage Analogy is Weird, Why The Notion of Focus, Focus, Focus is Overrated, Why Narrow Point Solutions Are Not Best in Class Products & The Rise of the "Compound Startup"
Apr 29, 2021 positive
Insight
Xbox forced Roblox to prioritize game quality over quantity at launch
“In order to do that, they couldn't just open up all the millions of games that they have on Roblox that can look like YouTube in terms of almost too much choice, and Microsoft and Xbox forced them to have a very limited small number of games that were on that …”
Chris Fralic Apr 29, 2021 ▶ 30:47 20VC: The Roblox Memo: First Round's Chris Fralic on The 17 Year Journey to Build a $41BN Market Cap Company, Why It Is Way Harder To Increase Ownership Across Rounds Today & What Happens Post SPACMania
Jun 10, 2021 positive
Disclosure
Simons: Atlassian drew inspiration from Microsoft's platform ecosystem strategy
“We drew a lot of inspiration from Microsoft, which I think is a textbook case here.”
Jay Simons Jun 10, 2021 ▶ 10:03 20VC: Why and How The Best Companies Build Economies Around Themselves, When, Why and How To Build Effective Partner/Channel Networks & The Power of Compounding Growth in SaaS with Jay Simons, General Partner @ Bond
Jun 10, 2021 bullish
Assertion Not checkable as stated
Simons: Partner ecosystems and certifications made Microsoft a generational business
“I think if you look back on time before they had the brand and direct reach that they have today, they had reached through this incredibly durable partner ecosystem and the customer economy built around getting Microsoft certified and having that sort of crede…”
Jay Simons Jun 10, 2021 ▶ 10:18 20VC: Why and How The Best Companies Build Economies Around Themselves, When, Why and How To Build Effective Partner/Channel Networks & The Power of Compounding Growth in SaaS with Jay Simons, General Partner @ Bond
Jul 22, 2021
What-if
Immelt: GE should have partnered with Salesforce or Microsoft for software
“Here's what I would have done differently, you know, Harry, in all honesty, I've had four years to think about it, is I would have either bought a part of a startup company or done a joint venture with maybe salesforce.com or Microsoft and created a new co, cr…”
Jeff Immelt Jul 22, 2021 ▶ 8:50 20VC: Jeff Immelt on Leadership Lessons from 16 Years as CEO @ GE, Incumbent Innovation; Why Some Have Failed and Other Succeeded, When Boards Have A Positive vs Negative Impact on a Company & The One Fear Startup Founders Are Allowed To Have
Jul 29, 2021
Assertion Supported
Quarles: OpenTable Ran on an Old Microsoft On-Premises Database
“When I got into the company, we were at a point at which the software that we had inside the restaurant was an old Microsoft on-prem distributed database, like not in the cloud.”
Krista Quarles Jul 29, 2021 ▶ 12:27 20VC: A Masterclass in Leadership and Scaling Companies: The Decisions only the CEO Can Make, The Secret To Talent Acquisition and Retention and How To Find The Unscalable Things that are Fundamental To Scale with Christa Quarles, CEO @ Corel Corporation
Apr 8, 2022 negative
Opinion
Liaw: Regulatory fear has chilled M&A for Meta, Google, Amazon, and Apple
“I think that probably the bigger challenge is for a lot of the biggest mega cap tech companies, fear of regulation and regulatory authority intervention is probably causing a lot of them to say, this is probably not worth our time, right? So it's kind of a fun…”
Eric Liaw Apr 8, 2022 ▶ 11:53 20VC: What Happens To Growth Rounds in this New Environment? Where is the Funding Crunch? How Does This Impact M&A and Going Public? How do Crossover Funds Respond? What Does it Mean For Early Stage and more with Eric Liaw, General Partner @ IVP
Jul 25, 2022
Insight
Fadell: Incumbents react to disruption by laughing, suing, then joining
“Every single, almost every single thing I've ever done, the first thing is the incumbents laugh at you. So whether it was an iPod, what happens? Microsoft laughs, ha, ha, ha, ha, ha. IPhone, iPhone comes out. Nokia, ha, ha, ha, ha, ha. Nest, Honeywell, ha, ha,…”
Tony Fadell Jul 25, 2022 ▶ 30:59 Tony Fadell: Why You Can't Be a Solo Founder; Mercenary vs. Missionary Operators | 20VC #910 · 20VC with Harry Stebbings
Sep 2, 2022 positive
Assertion Partly supported
Haas: Masayoshi Son lost 90% of his net worth and recovered it
“Arm is owned by SoftBank. So, Masayoshi-san, who's, I think, in the top 50 most wealthy people in the world, in the year 2000, he was the wealthiest man in the world, I think, for, he likes the joke, for about 20 nanoseconds when the SoftBank stock was higher …”
René Haas Sep 2, 2022 ▶ 26:02 20VC: Arm CEO Rene Haas on How The Best Leaders Make Decisions and The Trade-Off Between Speed and Quality | Leadership Lessons from 7 Years at Nvidia | How Companies Can Retain Speed, Innovation and Agility at Scale
Oct 25, 2022 positive
Assertion Supported
Microsoft offered Tellme Networks an acquisition term sheet for $800M
“By the end of the weekend, three days later, I had a term sheet for seven hundred sixty million dollars. Plus the cash and imbalances. So just about eight hundred million dollars.”
Emil Michael Oct 25, 2022 ▶ 9:17 Emil Michael: How I Negotiated the $4B Uber-China Deal, Why DoorDash Caught Up to Uber | 20VC #941 · 20VC with Harry Stebbings
Nov 14, 2022 neutral
Assertion Supported
Wood: FAANGs, Microsoft, and Nvidia made up nearly 50% of Nasdaq 100 in 2021
“Last year the market reached all-time highs in twenty-twenty-one as we were selling off, and it was the Fangs, it was Microsoft, it was Nvidia, and those, if you look at the Nasdaq 100, account for, account ed at that time, for nearly 50% of that index”
Cathie Wood Nov 14, 2022 ▶ 18:21 Cathie Wood: Elon & Twitter; Why Facebook is a Value Stock Now; ARK's Performance | 20VC #949 · 20VC with Harry Stebbings
Nov 14, 2022 bullish
Insight
Wood: Zoom and Microsoft lead enterprise comms cloud rip-and-replace cycle
“It and Microsoft are the two beneficiaries of the first rip and replace cycle that we've seen in the enterprise communication space since the early nineties when Cisco was building out the internet now, but that was on-prem and hardware oriented. Now we're mov…”
Cathie Wood Nov 14, 2022 ▶ 55:49 Cathie Wood: Elon & Twitter; Why Facebook is a Value Stock Now; ARK's Performance | 20VC #949 · 20VC with Harry Stebbings
Dec 16, 2022 positive
Assertion Supported
Partovi: Microsoft earnings grew fantastically under Steve Ballmer's CEO tenure
“The Steve years were not great for Microsoft's stock price. They were fantastic for Microsoft's earnings and earnings growth.”
Hadi Partovi Dec 16, 2022 ▶ 8:24 Hadi Partovi: How I Became an Advisor to Mark Zuckerberg; Lessons from Steve Ballmer | 20VC #961 · 20VC with Harry Stebbings
Dec 16, 2022 positive
Opinion
Partovi: Steve Ballmer deserves far more credit for building Microsoft
“Steve Ballmer does not get anywhere near enough credit for having built Microsoft's into the powerhouse that it is right now.”
Hadi Partovi Dec 16, 2022 ▶ 8:06 Hadi Partovi: How I Became an Advisor to Mark Zuckerberg; Lessons from Steve Ballmer | 20VC #961 · 20VC with Harry Stebbings
Dec 16, 2022
Assertion Not checkable as stated
Partovi Personally Competed Against Steve Ballmer to Recruit Harvard and MIT Talent
“Even while I was at Tell Me, we were fighting, I was personally fighting Balmer on recruiting Harvard graduates and MIT graduates. I would call a student, He would call a student. I would call them back. He would call them back. And he knew that this was happe…”
Hadi Partovi Dec 16, 2022 ▶ 6:36 Hadi Partovi: How I Became an Advisor to Mark Zuckerberg; Lessons from Steve Ballmer | 20VC #961 · 20VC with Harry Stebbings
Feb 1, 2023 bullish
Prediction Open · timeframe Feb 2028
Only Microsoft or SAP are large enough to potentially acquire Deel
“I think right now, unless you know, Microsoft or SAP, more Microsoft decides they want to get into HR. I don't see anyone being able to bring us in”
Alex Bouaziz Feb 1, 2023 ▶ 53:36 Alex Bouaziz: How We Became a $12B HR Company with 2,000 Remote Employees | 20VC #973 · 20VC with Harry Stebbings
Mar 8, 2023 bullish
Insight
Coates: Microsoft's AI Bing launch is an asymmetric attack on Google
“Search is like a non-part of their business, but search is everything to Google. Like if search ads stop working, Google doesn't, is not a thing anymore. And so they are swinging for the fences with a completely novel approach, which might not work, but if it …”
Glen Coates Mar 8, 2023 ▶ 55:26 Glen Coates: Why Shopify Will Dominate Amazon; How Microsoft Made Smartest Move of 2023 | E986 · 20VC with Harry Stebbings
Apr 28, 2023 positive
Opinion
Guo: Satya Nadella and Kevin Scott led Microsoft's AI transition brilliantly
“I mean, how could you not, right? I think Satya has done an amazing job making a, making Satya and Kevin Scott have done an amazing job championing, like really believing in this set of technologies, taking a bunch of bets, open AI and otherwise, using it as a…”
Sarah Guo Apr 28, 2023 ▶ 24:46 Sarah Guo: On Her New $101M Fund; How AI Impacts Inequality; AI Startups vs Incumbents | E1007 · 20VC with Harry Stebbings
May 3, 2023 neutral
Assertion Not checkable as stated
Hankes: Best AI Talent Remains Heavily Clustered in Big Tech
“If you think about where the best talent in AI is right now, I think it's OpenAI, And then I think you'd, everyone would tell you it is Google and Facebook and Microsoft and Amazon. And maybe there are folks that have kind of dripped their way into the startup…”
Vince Hankes May 3, 2023 ▶ 25:18 Vince Hankes: Why We Put $300M into OpenAI; Sam Altman's Pitch; Lessons from Josh Kushner | E1009 · 20VC with Harry Stebbings
Jun 2, 2023 bearish
Assertion Not checkable as stated
Hanks: Top AI talent remains heavily concentrated in big tech
“If you think about where the best talent in AI is right now, I think it's open AI. And then I think everyone would tell you it is Google and Facebook and Microsoft and Amazon. And maybe there are folks that have kind of dripped their way into the startup ecosy…”
Vince Hankes Jun 2, 2023 ▶ 8:03 20VC: Who Wins the AI Race; Startups or Incumbents & Does Having Proprietary Data Really Matter For Startups Today?
Jun 30, 2023 positive
Opinion
Douwe Kiela: Microsoft repositioned itself as an AI leader via OpenAI
“So I, I've been very impressed actually by how Microsoft has managed to turn everything around by strategically collaborating with a better AI lab in the shape of open AI. And they've just really turned that into this narrative where Microsoft is an AI leader …”
Douwe Kiela Jun 30, 2023 ▶ 45:35 Douwe Kiela: Why Data Size Matters More Than Model Size; Why Open Source Isn't Going to Win | E1032 · 20VC with Harry Stebbings
Jul 12, 2023
Insight
Egan: Early startup sales hires require intellectual range over big-company logos
“I think for a founder who's hiring, I could absolutely see where the big logo hire does not work out. I think, again, what you're looking for there is intellectual range, and that often doesn't just show up from, by the fact that they worked at Microsoft or ca…”
Kevin Egan Jul 12, 2023 ▶ 20:22 Kevin Egan: Biggest Lesson on Managing Sales Teams at Slack and Atlassian | E1034 · 20VC with Harry Stebbings
Aug 11, 2023 bullish
Opinion
Lessin: The most obvious AI bets are Facebook, Amazon, and Microsoft
“It's like, you want to bet on AI? Bet on Facebook. Bet on Amazon. Bet on Microsoft. It's so obvious.”
Sam Lessin Aug 11, 2023 ▶ 0:05 DEBATE: State of Seed Investing w/ Jason Lemkin, Sam Lessin, Frank Rotman & Harry Stebbings | E1047 · 20VC with Harry Stebbings
Aug 25, 2023 bullish
Prediction Held up
Howie Liu: Microsoft Copilot Will Drive Significant ARPU Growth Across Office
“When you think about like Microsoft's co-pilot offering, it's going to add significant ARPU to every single seat of office, which is a massive install base, right?”
Howie Liu Aug 25, 2023 ▶ 21:58 Howie Liu: Decoding Airtable's $11B Valuation; The Impending AI Revolution in Enterprise | E1053 · 20VC with Harry Stebbings
Sep 22, 2023 positive
Opinion
Kleinerman: Satya Nadella proved early Microsoft doubters wrong
“I was super wrong. When Satya came into the enterprise business, this is before he was CEO, he came in in very short order and made a lot of really difficult decisions. How the org was structured how contractors were hired, how we thought about the cloud versu…”
Christian Kleinerman Sep 22, 2023 ▶ 44:08 Christian Kleinerman: Do OpenAI and Anthropic Have a Sustaining Moat? Who Wins the AI Wars? | E1063 · 20VC with Harry Stebbings
Sep 22, 2023 positive
Assertion Not checkable as stated
Kleinerman: Copyright fears stall enterprise AI; Microsoft's legal indemnity is material
“Because enterprises are worried about if they incorporate Gen AI into any of their products or services in a way that they truly depend on them, and at some point lawsuits start to fly, they're exposed, and because of those concerns, it has held back enterpris…”
Christian Kleinerman Sep 22, 2023 ▶ 28:47 Christian Kleinerman: Do OpenAI and Anthropic Have a Sustaining Moat? Who Wins the AI Wars? | E1063 · 20VC with Harry Stebbings
Nov 15, 2023 bearish
Opinion
Stebbings: AI Upside Is Already Priced Into Microsoft and Nvidia
“And my hard thing is like, as a general capital allocator and capitalist who wants to make money, I think the upside is already priced into Microsoft or Nvidia, where I'm not looking at them like, oh, there's a buying opportunity now because they're so richly …”
Harry Stebbings Nov 15, 2023 ▶ 56:00 Des Traynor: How to Survive and Thrive in a World of OpenAI | E1082 · 20VC with Harry Stebbings
Dec 4, 2023 positive
Assertion Not checkable as stated
Microsoft CEO Satya Nadella mentors Procore CEO Tooey Courtemanche
“I have the fortunate privilege of having Satya be a mentor of mine, and I am absolutely fascinated by the complexity of that business, and how he makes sense out of it all.”
Tooey Courtemanche Dec 4, 2023 ▶ 1:18:21 Tooey Courtemanche: From Construction Worker to Billionaire CEO | E1090 · 20VC with Harry Stebbings
Jan 10, 2024 bullish
Prediction Partly held up
Sim: Microsoft's AI leadership will drive cloud market share and H2 revenue
“Because of their lead on everything AI that they're taking market share on the cloud side. So I think that that's going to drive a lot of their business. And I'm hoping that by the back half of the year, you know, you start seeing some of the revenue numbers r…”
Ed Sim Jan 10, 2024 ▶ 1:06:52 Ed Sim & Jamin Ball: Did Figma Kill M&A Markets & 3 Requirements to IPO in 2024 | E1101 · 20VC with Harry Stebbings
Jan 17, 2024 negative
Insight
Software R&D costs continuously increase over time, contrary to government expectations
“Software, first of all, software R&D costs only increase. You know, it's like no one, no investor thinks Microsoft's gonna spend less in the future on R&D than they spend in the present moment. That would be crazy. But the government somehow expects that to be…”
Shyam Sankar Jan 17, 2024 ▶ 17:19 Shyam Sankar: The Broken Incentive Structure of How Governments Buy Defence | E1104 · 20VC with Harry Stebbings
Jan 19, 2024
Disclosure
Google and Microsoft rejected Zaria Parvez's job applications out of college
“I've been rejected from big brands for jobs and I was applying out of college because I, my resume, I can send it to you after this, but it's definitely not a traditional resume. It's very different. It's very, it's unhinged. And my whole like life mantra was …”
Zaria Parvez Jan 19, 2024 ▶ 40:06 Zaria Parvez: How Duolingo Scaled to 8M TikTok Followers & How to Create Viral Content | E1105 · 20VC with Harry Stebbings
Mar 1, 2024 neutral
Assertion Supported
Quattrone: Salesforce submitted higher unsolicited bids during LinkedIn's exclusivity window with Microsoft
“So they went into like a 30 day exclusivity to try to get to definitive agreement. And during that period, Salesforce lobbed in Several offers that were higher. And that meant that towards the end of that period, we had to inform Microsoft, Hey, your deal is n…”
Frank Quattrone Mar 1, 2024 ▶ 35:04 Frank Quattrone: Lessons from 650 M&A Deals Worth Over $1TRN & Taking Amazon and Cisco Public| E1121 · 20VC with Harry Stebbings
Mar 1, 2024 neutral
Assertion Supported
Quattrone: Microsoft and Salesforce submitted nearly identical bids at every stage for LinkedIn
“With LinkedIn, we had interest from several parties, but it really kind of came down to Microsoft and Salesforce. And I've never seen companies bid privately and come up with such close prices on every stage Like, 151 151 162 163. It was very, very close, and …”
Frank Quattrone Mar 1, 2024 ▶ 33:36 Frank Quattrone: Lessons from 650 M&A Deals Worth Over $1TRN & Taking Amazon and Cisco Public| E1121 · 20VC with Harry Stebbings
Mar 4, 2024 bullish
Disclosure
Microsoft is the Norwegian sovereign wealth fund's largest equity position
“Our biggest position is Microsoft. We have big, very big positions in you know, Nvidia, AMD. Alphabet. You name them, we have. Those are our biggest positions.”
Nicolai Tangen Mar 4, 2024 ▶ 23:05 Nicolai Tangen: Managing the Largest Sovereign Wealth Fund in the World | E1122 · 20VC with Harry Stebbings
Mar 20, 2024 positive
Assertion Contradicted
Stebbings: Microsoft generates $350 million per day in free cash flow
“They don't have the cash flow capabilities of Microsoft doing three hundred and fifty million dollars a day in free cash flow.”
Harry Stebbings Mar 20, 2024 ▶ 53:38 Jean-Michel Lemieux: Three Product Decisions Every Team Needs to Make | E1129 · 20VC with Harry Stebbings
Apr 3, 2024 negative
Disclosure
Stebbings: Prefers Legacy Sectors Over Competing With AI Giants
“For me, it's like a non-competitive industry. I never want to compete against fucking Sam Altman doing foundation models and Dario from Anthropic and Satya at Microsoft. I want, like, legacy architecture. I want, like, high pricing power. I want really, really…”
Harry Stebbings Apr 3, 2024 ▶ 14:08 Trae Stephens: Why No Company is Successful Because of their VC | E1135 · 20VC with Harry Stebbings
Apr 8, 2024
Assertion Contradicted
Stebbings: Microsoft generates $350 million per day in free cash flow
“We've never had incumbents who throw off three hundred and fifty million a day in free cash flow like Microsoft does”
Harry Stebbings Apr 8, 2024 ▶ 56:18 Bastian Lehmann: How the Uber Deal Went Down and How a $2.65BN Deal Turned into $5BN | E1137 · 20VC with Harry Stebbings
Apr 22, 2024 neutral
Disclosure
Daniel Dines Saved $150,000 During Five Years at Microsoft Before Founding UiPath
“So in five years working in Microsoft, my old savings were like a 150,000 dollars.”
Daniel Dines Apr 22, 2024 ▶ 30:13 Daniel Dines: From a Dollar a Day to Romania's Richest Man| Happiness, Wealth, Risk and more | E1143 · 20VC with Harry Stebbings
May 8, 2024 bullish
Assertion Supported
Stebbings: Microsoft generates $350 million in cash daily
“Microsoft is throwing off three hundred and fifty million in cash a day.”
Harry Stebbings May 8, 2024 ▶ 54:50 Tom Hulme: Lessons from a 24x Angel Track Record, 275x on Robinhood & Making Billions on Uber |E1150 · 20VC with Harry Stebbings
May 8, 2024 negative
Assertion Contradicted
Hulme: Microsoft acquired Inflection primarily for its 12,000 H100 GPU cluster
“I do not believe that Microsoft were buying the Pi model. I think Microsoft are GPU constrained, and we're buying a cluster of 12,000 H-one hundreds.”
Tom Hulme May 8, 2024 ▶ 49:13 Tom Hulme: Lessons from a 24x Angel Track Record, 275x on Robinhood & Making Billions on Uber |E1150 · 20VC with Harry Stebbings
May 20, 2024 bearish
Prediction Not checkable as stated
Stebbings: Vertical AI applications will lose to Microsoft's distribution advantage
“Actually, I think they will lose despite being better products because Microsoft has Distribution. They will tack on the product, which is the same, maybe five, 10% worse, and win because they have distribution.”
Harry Stebbings May 20, 2024 ▶ 7:33 Nikesh Arora: Lessons from $102BN Market Cap & How to Create & Sustain Competitive Advantage | E1155 · 20VC with Harry Stebbings
Jun 10, 2024
Assertion Not checkable as stated
US Tech Giants Have Legal Autonomy That Chinese Counterparts Lack
“Google does not work for the US government. Microsoft does not work for the US government. There is, there's ways they're accountable by law, but they have to go through a legal process for that kind of thing. And so, given that legal process doesn't exist wit…”
Reid Hoffman Jun 10, 2024 ▶ 57:56 Reid Hoffman: The Future of TikTok and The Inflection AI Deal | E1163 · 20VC with Harry Stebbings
Jun 10, 2024 neutral
Assertion Partly supported
Microsoft Board Approved $1B for OpenAI Despite Having No Clear Product
“The very first OpenAI Microsoft deal was, you know, Satya and Kevin Scott brought to the Microsoft board. We want to put a billion dollars into the investment in this vehicle. From a five one C three that doesn't really have any particular plans at making its …”
Reid Hoffman Jun 10, 2024 ▶ 29:58 Reid Hoffman: The Future of TikTok and The Inflection AI Deal | E1163 · 20VC with Harry Stebbings
Jun 10, 2024 positive
Opinion
Satya Nadella Demonstrated Unprecedented Large-Scale Cultural Transformation at Microsoft
“Look, Satya has been, probably the thing I've most learned from Satya has been, how do you do cultural transformation of massive scale organizations? And he has demonstrated that that is doable and possible. In ways that I don't know if anyone ever has before.”
Reid Hoffman Jun 10, 2024 ▶ 1:07:24 Reid Hoffman: The Future of TikTok and The Inflection AI Deal | E1163 · 20VC with Harry Stebbings
Jun 10, 2024 bearish
Insight
Startups Cannot Finance Pre-Revenue Billion-Dollar AI Compute Runs
“Look, if you're saying what really matters is, like, the driving function here will be the billion dollar compute run to make this model, it'll be very difficult for startups to do that, right? I mean, even in this more modern global venture capital where star…”
Reid Hoffman Jun 10, 2024 ▶ 27:22 Reid Hoffman: The Future of TikTok and The Inflection AI Deal | E1163 · 20VC with Harry Stebbings
Jul 19, 2024 negative
Prediction Open · timeframe Jul 2029
Adams: Paid AI add-ons will commoditize into standard tiers
“I think in the short term, it might allow them to make more money. So, like, I think Microsoft and Google both have add-on packages that you pay for to get access to their AI stuff. I think that's a very short-term thing where it'll just become commoditized, p…”
Cameron Adams Jul 19, 2024 ▶ 22:21 Cameron Adams: How Canva Builds Products: Lessons Learned, What Works? What Flopped? | E1179 · 20VC with Harry Stebbings
Aug 14, 2024 bullish
Opinion
Nejatian: Stripe-Shopify relationship is the most value-creating in software history
“And this Stripe-Shopify relationship Is likely the most value creating relationship in the history of software. It would have been Intel, Microsoft before Intel and Microsoft had had divorce is too hard a word, but had like the thing they did.”
Kaz Nejatian Aug 14, 2024 ▶ 43:45 Kaz Nejatian: How Shopify Built a $90BN Business to Last 100 Years | E1189 · 20VC with Harry Stebbings
Sep 25, 2024 positive
Opinion
Vishria: Tech incumbents are too paranoid and alert to be easily disrupted in AI
“Today's incumbents are and you know, this is a trope and not really an insight. Everyone's saying the same thing, but today's incumbents are paranoid and on top of things and like, you know, like is, is Microsoft and Nuance gonna move slower and whatever than …”
Eric Vishria Sep 25, 2024 ▶ 21:54 Eric Vishria: Where is the Value in AI - Chips, Models or Apps? | E1206 · 20VC with Harry Stebbings
Oct 7, 2024 bullish
Prediction Held up
Kant: Poolside, OpenAI, and Anthropic will rival Big Tech in AI
“What I would like to see and what I think is going to happen is that it's not just Google, Amazon, and Microsoft. It's going to be, you know, an open eye, an anthropic, a poolside, and a set of companies who are able to get that massive escape velocity needed …”
Eiso Kant Oct 7, 2024 ▶ 53:29 Eiso Kant, CTO @Poolside: Raising $600M To Compete in the Race for AGI | E1211 · 20VC with Harry Stebbings
Oct 7, 2024 neutral
Disclosure
Kant: Poolside deliberately excluded Google, Microsoft, and Amazon from $500M round
“If look at our capital raise, our last five hundred million dollar round, you'll see that there's none of the big hyperscalers, Google, Microsoft, you know, Amazon were part of the round.”
Eiso Kant Oct 7, 2024 ▶ 43:43 Eiso Kant, CTO @Poolside: Raising $600M To Compete in the Race for AGI | E1211 · 20VC with Harry Stebbings
Oct 7, 2024 negative
Disclosure
Kant: Rejecting GitHub's all-stock acquisition offer was my worst financial decision
“It was probably the dumbest financial decision of my life, considering it was an all stock offer and GitHub sold to Microsoft, I think, less than a year later.”
Eiso Kant Oct 7, 2024 ▶ 1:07:14 Eiso Kant, CTO @Poolside: Raising $600M To Compete in the Race for AGI | E1211 · 20VC with Harry Stebbings
Oct 21, 2024 positive
Disclosure
Hamid: Yammer's $1.2B sale freed him to invest in Slack
“There's one particular example that I think ended up working out pretty well. This is when Yammer got acquired by Microsoft it was a 1.2 billion dollar acquisition. At the time it felt like, man, we've got so much ahead of us. Yammer can become the next Slack,…”
Mamoon Hamid Oct 21, 2024 ▶ 28:32 Mamoon Hamid: AI - Where Value Accrues, Startups vs Incumbents & Scaling Laws | E1217 · 20VC with Harry Stebbings
Oct 23, 2024 negative
Opinion
Slack lost to Microsoft by over-relying on product-led growth
“We lost the distribution war at Slack. I think part of why we lost that war was, yes, like, monopolistic behavior by Microsoft, but Because we didn't lean into other effective fast distribution strategies other than PLG.”
AJ Tennant Oct 23, 2024 ▶ 1:03:56 AJ Tennant: How to Build a Sales Machine and Where Most Go Wrong | E2118 · 20VC with Harry Stebbings
Nov 25, 2024 positive
Disclosure
Jason Citron explains why Discord rejected Microsoft's acquisition offer
“Microsoft has been a really fantastic partner for us. And there certainly are things that we could have done together with them that we can't do independently, but ultimately it was about You know, controlling your own destiny, I suppose, and really seizing th…”
Jason Citron Nov 25, 2024 ▶ 30:31 Jason Citron, Co-Founder/CEO @Discord: The Untold Story Behind Scaling to 200M Users | E1230 · 20VC with Harry Stebbings
Dec 6, 2024 bullish
Opinion
Stebbings: OpenAI has virtually no downside risk due to Microsoft backstop
“I didn't actually think there's actually any chance that it's a goose egg. I mean, maybe it's like a one or a two percent. I think the chance that Microsoft actually takes something with it and It, you get the press stack back at least.”
Harry Stebbings Dec 6, 2024 ▶ 1:04:29 Zachary Bookman: Why Valuations and Fundraising are BS | E1235 · 20VC with Harry Stebbings
Jan 8, 2025 bearish
Disclosure
Dan Gill would pass on investing in OpenAI, Anthropic, and xAI
“I wouldn't invest in any of them. I think that the foundational models are trending towards commoditization and it's gonna be difficult to capture all of the gains relative to what, you know, Google, Google can capture and Microsoft can capture and others.”
Dan Gill Jan 8, 2025 ▶ 1:04:37 Dan Gill, CPO @Carvana: The Most Wild Story in Public Markets | E1243 · 20VC with Harry Stebbings
Jan 13, 2025 negative
Opinion
Pishevar: Steve Ballmer was a terrible CEO despite massive wealth
“Steve Ballmer. You know, the decade that he was CEO of Microsoft, Microsoft was completely just flat, right? And he's now richer than Bill Gates, right?”
Shervin Pishevar Jan 13, 2025 ▶ 1:11:21 Shervin Pishevar: What Really Happened in the Firing of Travis Kalanick | E1245 · 20VC with Harry Stebbings
Feb 12, 2025 bullish
Opinion
Odoo's product is years ahead of Microsoft and SAP
“I think our product is years ahead of the competition. There is no way they can do what we do.”
Fabien Pinckaers Feb 12, 2025 ▶ 20:06 Fabien Pinckaers, CEO @Odoo: The Billionaire Founder Who Doesn’t Care About Money | E1259 · 20VC with Harry Stebbings
Feb 12, 2025 negative
Opinion
SAP and Microsoft enterprise software is shitty, slow, and expensive
“On the market, you have two types of market. You have the large players, like SAP and Microsoft. They do several applications, but it's shitty, it's slow, it's expensive. And people are not happy using it.”
Fabien Pinckaers Feb 12, 2025 ▶ 40:41 Fabien Pinckaers, CEO @Odoo: The Billionaire Founder Who Doesn’t Care About Money | E1259 · 20VC with Harry Stebbings
Feb 24, 2025 positive
Assertion Not checkable as stated
Morin: Microsoft's AMD chip deployments made OpenAI inference profitable
“Microsoft comes along and buys it all, makes, by the way, OpenAI, or at least on the inference side, puts OpenAI in the green because of the efficiency gains.”
Steeve Morin Feb 24, 2025 ▶ 39:44 Steeve Morin: Why Google Will Win the AI Arms Race & OpenAI Will Not | E1262 · 20VC with Harry Stebbings
Mar 10, 2025 bullish
Prediction Not checkable as stated
Jake Saper: Microsoft is the safest 10-year stock index for B2B software
“I think Microsoft, and the reason that's the case is because I'm obviously long B to B software, and that's probably the best index.”
Jake Saper Mar 10, 2025 ▶ 1:21:25 Jake Saper, GP @ Emergence Capital: "We Sold Salesforce Early and Lost Out on Billions" · 20VC with Harry Stebbings
Mar 14, 2025 bullish
Opinion
Biilmann: Microsoft is the safest 10-year stock buy under Satya Nadella
“It's a hard one, but I would probably say Microsoft. I think again, if you can only buy one, you probably want it to be a pretty safe one. You want it to be one that benefits from all of the disruption AI is going to bring to the field rather than like falls f…”
Matt Biilmann Mar 14, 2025 ▶ 40:03 20Product: How to Design and Build Products in a World of Agents | Why AI Will Kill Many SaaS Products | What Products Will Thrive and Die in a World of 100M Developers with Matt Biilmann, Co-Founder and CEO @ Netlify
Mar 17, 2025 bullish
Prediction Not checkable as stated
Rangan: Microsoft is the single public stock to buy and hold for 10 years
“Oh, Microsoft.”
Yamini Rangan Mar 17, 2025 ▶ 49:20 Yamini Rangan, CEO @ HubSpot: How HubSpot Competes Against Salesforce · 20VC with Harry Stebbings
Mar 21, 2025 bearish
Opinion
Torres: Nobody is using Microsoft Copilot because the product doesn't work
“Copilot, everybody was like, they're just ahead making all the money first because people, the problem is people are, they just have so much hard time trusting someone, right? And so they're reaping the benefit of being early, But nobody's using the product, r…”
Elias Torres Mar 21, 2025 ▶ 13:34 Elias Torres, Co-Founder and CEO @ Agency: What No One Tells You About Selling Your Company · 20VC with Harry Stebbings
Mar 31, 2025 positive
Prediction Not checkable as stated
Scott: AI agent memory will improve significantly over the next year
“I think one of the things is going to happen because I know lots of people are working on it right now is memory is going to get a lot better over the next year or so, which means that as you're using an agent, like, and it remembers more and more about your p…”
Kevin Scott Mar 31, 2025 ▶ 26:08 Kevin Scott, CTO @ Microsoft: An Evaluation of Deepseek and How We Underestimate the Chinese · 20VC with Harry Stebbings
Mar 31, 2025 bullish
Assertion Not checkable as stated
Scott: AI scaling laws have not hit a limit yet
“I can very clearly see what we're doing now and like what we're doing next. And I don't see the limit to the scaling laws. Like if you're just sort of thinking about the raw capability of the models and like how well you can condition them to reason over incre…”
Kevin Scott Mar 31, 2025 ▶ 8:31 Kevin Scott, CTO @ Microsoft: An Evaluation of Deepseek and How We Underestimate the Chinese · 20VC with Harry Stebbings
Mar 31, 2025 neutral
Prediction Not checkable as stated
Scott: AI will render traditional product engineering teams obsolete within ten years
“It basically means, and like, I don't think this is next year, but it's probably not going to be 10 years. This whole notion that the, That, that you have teams of people who are, who, whose job is to go anticipate a bunch of very granular user needs in some n…”
Kevin Scott Mar 31, 2025 ▶ 20:35 Kevin Scott, CTO @ Microsoft: An Evaluation of Deepseek and How We Underestimate the Chinese · 20VC with Harry Stebbings
Mar 31, 2025 bullish
Prediction Open · timeframe Mar 2030
Scott: 95% of net new code will be AI-generated within five years
“95% is going to be AI generated. I think very little is going to be line by line is going to be human written code.”
Kevin Scott Mar 31, 2025 ▶ 30:30 Kevin Scott, CTO @ Microsoft: An Evaluation of Deepseek and How We Underestimate the Chinese · 20VC with Harry Stebbings
Mar 31, 2025 bullish
Disclosure
Scott: Microsoft chose not to launch models more interesting than DeepSeek-R1
“We've had models more interesting than Deep Seek R-One that, like, we didn't even We chose not to even launch them.”
Kevin Scott Mar 31, 2025 ▶ 15:05 Kevin Scott, CTO @ Microsoft: An Evaluation of Deepseek and How We Underestimate the Chinese · 20VC with Harry Stebbings
Apr 24, 2025 neutral
Assertion Open
O'Driscoll: Only Two or Three Independent PC Productivity App Companies Scaled
“After 20 years of the PC wars, there was really only two or three companies at scale That were selling apps that were personal productivity apps independent of Microsoft. It was, you know, you had Adobe, you had Quicken and maybe some of the security apps.”
Rory O'Driscoll Apr 24, 2025 ▶ 9:18 How LP Deployment to Venture Will Change in 2025 & Are Endowment Funds in Trouble? · 20VC with Harry Stebbings
May 1, 2025 bearish
Opinion
Lemkin: Destroying Cursor and Windsurf is existential for Microsoft's GitHub
“Co-pilot versus Cursor and WinServe is number friggin' one on their gotta kill list for Microsoft, number one. It's all over. It is existential for that, for GitHub to destroy them.”
Jason Lemkin May 1, 2025 ▶ 55:09 What Does it Take to Be Good at Series A and B Today? · 20VC with Harry Stebbings
May 1, 2025 negative
Opinion
O'Driscoll: Box's valuation suffers from competing against free Microsoft and Google
“The reason the stock price is always hard is we're competing against Microsoft and Google who give it away for free.”
Rory O'Driscoll May 1, 2025 ▶ 51:41 What Does it Take to Be Good at Series A and B Today? · 20VC with Harry Stebbings
May 15, 2025
Assertion Supported
Lemkin: Microsoft Laid Off 3% of Its Workforce
“Microsoft laid off three percent of their company today.”
Jason Lemkin May 15, 2025 ▶ 0:10 OpenAI, SBF & Perplexity: What VCs Know That You Don’t · 20VC with Harry Stebbings
May 15, 2025 positive
Assertion Contradicted
Lemkin: Microsoft's OpenAI Deal Includes 10% Revenue Share Until AGI
“Getting everything they get plus 10% of all revenue until there's AGI plus the returns.”
Jason Lemkin May 15, 2025 ▶ 56:04 OpenAI, SBF & Perplexity: What VCs Know That You Don’t · 20VC with Harry Stebbings
May 22, 2025 negative
Opinion
O'Driscoll: Microsoft Open-Sourcing VS Code Signals Relative Weakness
“If you were the developer behemoth, which was Microsoft, the fact that you have to do this now to remain relevant at a zoom out level, This is a sign of relative weakness, not absolute weakness.”
Rory O'Driscoll May 22, 2025 ▶ 1:05:22 Rippling vs. Deel Lawsuit: WTF Happens Now? The Future of the Late Stage Private Market · 20VC with Harry Stebbings
May 29, 2025 negative
Prediction Not checkable as stated
O'Driscoll: OpenAI will declare AGI based on Microsoft contract negotiations
“It'll achieve open AGI whenever it suits Sam Altman in his negotiations with Microsoft over the open AGI term in that contract to declare it to be AGI. Because it's a meaningless, ill-defined term that will be used for economic leverage.”
Rory O'Driscoll May 29, 2025 ▶ 1:08:05 OpenAI’s $6BN Jony Ive Deal & YC Is Both Chanel and Walmart, and Has Officially Won! · 20VC with Harry Stebbings
Jun 19, 2025 positive
Opinion
O'Driscoll: Microsoft holds leverage in ambiguous situations because it isn't existential
“In situations of ambiguity, the person who has the most leverage has the best chance to win, and I would argue Microsoft has quite a lot of leverage because it's not existential for them, especially now.”
Rory O'Driscoll Jun 19, 2025 ▶ 41:50 Chime IPO: Are IPOs Hotter Than Ever? · 20VC with Harry Stebbings
Jun 19, 2025 neutral
Prediction Didn’t hold up
O'Driscoll: AGI's arrival will be defined by Microsoft and OpenAI litigation
“My comment is we're going to hit AGI when Microsoft and OpenAI litigate what OpenAGI is.”
Rory O'Driscoll Jun 19, 2025 ▶ 42:53 Chime IPO: Are IPOs Hotter Than Ever? · 20VC with Harry Stebbings
Jun 19, 2025 bearish
Opinion
Lemkin: Microsoft has no leverage over OpenAI because AGI is imminent
“The reason I think they have no leverage is because I think that whatever AGI is, we're going to be there pretty soon.”
Jason Lemkin Jun 19, 2025 ▶ 42:14 Chime IPO: Are IPOs Hotter Than Ever? · 20VC with Harry Stebbings
Jun 26, 2025 positive
Prediction Held up
Lemkin: OpenAI and Microsoft will settle antitrust tensions privately
“I don't think Microsoft wants to be sued by any trust. So I think it's going to get worked out.”
Jason Lemkin Jun 26, 2025 ▶ 1:08:53 Navan Files to Go Public and Canva Pulls the Brakes: Why and What Happens? · 20VC with Harry Stebbings
Jun 26, 2025 positive
Prediction Open · timeframe Dec 2025
Rory O'Driscoll: OpenAI will publicly accuse Microsoft of antitrust in 2025
“Accused, by the way, is a wonderfully vague word. Will they file a lawsuit and prevail? Maybe not, but will Sam throw words out? Yeah. That two and a half x on a yes, I'd take that chance.”
Rory O'Driscoll Jun 26, 2025 ▶ 1:07:55 Navan Files to Go Public and Canva Pulls the Brakes: Why and What Happens? · 20VC with Harry Stebbings
Jul 21, 2025 positive
Assertion Not checkable as stated
Chen: Surge AI has more daily working PhDs than Big Tech combined
“Like if you think of all the PhDs, even at Google or Meta or Microsoft, we have way more than all of them combined doing work for us in a single day.”
Edwin Chen Jul 21, 2025 ▶ 40:23 Surge CEO & Co-Founder, Edwin Chen: Scaling to $1BN+ in Revenue with NO Funding · 20VC with Harry Stebbings
Jul 24, 2025 bearish
Prediction Not checkable as stated
O'Driscoll: AI model providers will eventually squeeze out software wrappers
“At some point when things get tougher, just like Microsoft did in the nineties, the platform provider starts to grind everyone's balls. And, you know, take more of the share away. There ain't 10 versions of PowerPoint in 20, 25.”
Rory O'Driscoll Jul 24, 2025 ▶ 17:45 How Do All Providers Deal with Anthropic Dependency Risk & Figma IPO Breakdown: Where Does it Price? · 20VC with Harry Stebbings
Jul 27, 2025
Insight
Fanton: Playing Chess And Guitar Is A Strong Heuristic For Exceptional PMs
“If you know how to play chess and play guitar, your will be a great PM because it's the creative side together with analytical side. Chess is a great proxy for analytical capability and playing instruments is an amazing proxy. For creativity.”
Fernando Fanton Jul 27, 2025 ▶ 18:07 20Product: Should We Kill the PM Role Entirely | How Does Product Design Change Most in a World of AI | How Do Monzo Build Product Today: What Works, What Does Not | Why Most Product Sucks and What Makes Truly Great Product
Jul 27, 2025 neutral
Disclosure
Fanton: Never Wrote PRDs After His Early Years At Microsoft
“I don't think I've ever done a PRD myself, except the first few years in Microsoft.”
Fernando Fanton Jul 27, 2025 ▶ 45:45 20Product: Should We Kill the PM Role Entirely | How Does Product Design Change Most in a World of AI | How Do Monzo Build Product Today: What Works, What Does Not | Why Most Product Sucks and What Makes Truly Great Product
Jul 28, 2025
Prediction Not checkable as stated
Stebbings: Whatever Sam Altman and Microsoft decide is AGI will define AGI
“I think to be honest, Sam Altman, that's the definition of what AGI is. So whatever him and Microsoft decide is AGI will be AGI.”
Harry Stebbings Jul 28, 2025 ▶ 1:05:34 a16z GP, Martin Casado: Anthropic vs OpenAI & Why Open Source is a National Security Risk with China · 20VC with Harry Stebbings
Aug 4, 2025
Assertion Partly supported
Big Four Tech Giants Generate $600B in Annual Operating Cash Flow
“You look at Google, Microsoft, Amazon, and Meta combined, I mean, they're doing six hundred billion of operating cash flow, just cash coming off the company every single year”
Miles Dieffenbach Aug 4, 2025 ▶ 1:11:57 Miles Dieffenbach: Inside Carnegie Mellon’s $4BN Endowment & The Math Behind DPI, TVPI, Illiquidity · 20VC with Harry Stebbings
Aug 4, 2025 positive
Disclosure
Microsoft remains Databricks' largest commercial partner
“Ali and I did the deal with Microsoft, right? Which became kind of pretty historical, I think in legend. And it's still, you know, Microsoft's our, you know, biggest partner. It's a amazing partner for us.”
Ron Gabrisko Aug 4, 2025 ▶ 43:15 20Sales: $0-$3.7BN: The Databricks CRO's Playbook to Build the Fastest GTM Engine in SaaS History | How Databricks Beat Snowflake | How To Build a Sales Org of 5,000 and Close $190M Deals with Ron Gabrisko
Aug 7, 2025 bullish
Opinion
O'Driscoll: Microsoft's post-OpenAI deal execution under Nadella has been perfect
“If you accept the constraint, That you can't build the core technology internally, which is what Microsoft Had to accept, and he accepted, right? Execution since then has been perfect.”
Rory O'Driscoll Aug 7, 2025 ▶ 1:04:45 Figma's 250% Pop - The Greatest IPO Mispricing Ever? Meta & Microsoft Blowout Quarters: Broken Down · 20VC with Harry Stebbings
Aug 21, 2025 negative
Assertion Supported
O'Driscoll: Microsoft's capital expenditure has reached 25% of its revenue
“Microsoft CapEx as a percentage of revenue has crept up to 25%.”
Rory O'Driscoll Aug 21, 2025 ▶ 1:10:34 Databricks at $100BN, CoreWeave’s $11B Debt Bet & Nubank’s $2.5B Profit Shocker - Ep.19 · 20VC with Harry Stebbings
Aug 21, 2025 bearish
Prediction Open · timeframe Aug 2028
Lemkin: CoreWeave will show signs of an AI slowdown before hyperscalers
“Core weave, if core weave struggles, if it can't service its debt, if it can't raise more debt through this weird through, through the hyperscalers guaranteeing it, that's where we'll see, even if there's just a bump in this cycle, that's not that, that doesn'…”
Jason Lemkin Aug 21, 2025 ▶ 58:17 Databricks at $100BN, CoreWeave’s $11B Debt Bet & Nubank’s $2.5B Profit Shocker - Ep.19 · 20VC with Harry Stebbings
Aug 28, 2025 negative
Assertion Partly supported
Benioff: Microsoft holds only 3% CRM market share
“Why Microsoft has three percent CRM market share because of nonsense.”
Marc Benioff Aug 28, 2025 ▶ 18:30 Anthropic's $10B Round, Klarna's IPO, Inside a16z's 72 Deal Seed Investment Machine ft. Marc Benioff · 20VC with Harry Stebbings
Sep 4, 2025 bearish
Opinion
O'Driscoll: $4T AI infrastructure investment requires impossible $800B annual profit
“Four, let's do four billion dollars. You want a 20% return on equity. You gotta be generating eight hundred billion of profit a year. That's a lot of profit when, you know, Facebook met, all these guys make a couple hundred billion a year, right? So you've got…”
Rory O'Driscoll Sep 4, 2025 ▶ 49:12 Anthropic Raises $13BN & OpenAI Buys Statsig for $1.1BN All Stock · 20VC with Harry Stebbings
Sep 5, 2025 positive
Assertion Not checkable as stated
Alex Schultz: Microsoft leads major tech hyperscalers in quantum computing
“They're leading in quantum. We don't talk about quantum very much, but Microsoft is leading of the big players In quantum.”
Alex Schultz Sep 5, 2025 ▶ 56:13 20Growth: Meta CMO Alex Schultz on How All Founders Have to Change Their Marketing Playbook in a World of AI | Is AI Plateauing, What it Means if China Wins the AI Race and Why Zuck is a Generational Leader
Sep 18, 2025 neutral
Assertion Contradicted
Lemkin: Microsoft shifting default model choice to Anthropic across several products
“Microsoft I think today said they're moving not just parts of office to Anthropic, but that it is the default choice for several other products and that Microsoft today said several months ago, they told their teams to start using cloud code several months ago…”
Jason Lemkin Sep 18, 2025 ▶ 44:01 Opendoor CEO, Kaz Nejatian: OpenAI and Oracle, How Can Either Afford to Do This · 20VC with Harry Stebbings
Sep 18, 2025 positive
Prediction Held up
O'Driscoll: OpenAI Will Buy Compute From Oracle If Cheaper Than Microsoft
“Do I think the Oracle will book a fair amount of cloud compute from OpenAI? Absolutely. Maybe not three hundred billion, but if he's willing to provide it at a lower price than Microsoft, my guess is those fine people at OpenAI will take it.”
Rory O’Driscoll Sep 18, 2025 ▶ 52:22 Opendoor CEO, Kaz Nejatian: OpenAI and Oracle, How Can Either Afford to Do This · 20VC with Harry Stebbings
Sep 18, 2025 bullish
Opinion
O'Driscoll: OpenAI and Anthropic No Longer Need Microsoft or Amazon
“In both these cases, the small company won. They got the money, they got the critical mass, they got the credibility, and now they've pulled away. And neither on top of now open AI needs Microsoft or Amazon at this point. They don't need them for money. They d…”
Rory O’Driscoll Sep 18, 2025 ▶ 49:41 Opendoor CEO, Kaz Nejatian: OpenAI and Oracle, How Can Either Afford to Do This · 20VC with Harry Stebbings
Sep 22, 2025 bullish
Assertion Contradicted
Taneja: Microsoft generated the highest multiple return among OpenAI investors
“Taking that bet was hugely, hugely valuable for Microsoft. I think, and if you look at the return, by the way, if they put in twenty billion, they are the ones who have the highest multiple return as well. So it was a great investment on a financial basis and …”
Hemant Taneja Sep 22, 2025 ▶ 39:43 General Catalyst CEO, Hemant Taneja: Lessons Scaling GC to $40BN in AUM · 20VC with Harry Stebbings
Sep 22, 2025 bearish
Opinion
Taneja: Microsoft and OpenAI's partnership is fracturing over colliding ambitions
“Is that an enduring investment? No, obviously now they've gone at odds with each other because there's an ambition that collides between the two companies and so they want to have more choice. They want to have anthropic at the table as well.”
Hemant Taneja Sep 22, 2025 ▶ 39:27 General Catalyst CEO, Hemant Taneja: Lessons Scaling GC to $40BN in AUM · 20VC with Harry Stebbings
Sep 29, 2025 negative
Opinion
Ross: Amazon lacks AI DNA compared to Google, Meta, and Microsoft
“Amazon, I think doesn't have AI DNA. And they, like, if you compare them, so you didn't mention Meta, right? But Meta and Google always had the AI DNA, and Microsoft bought it with OpenAI, but that bought them time. Amazon still doesn't have that DNA, but they…”
Jonathan Ross Sep 29, 2025 ▶ 1:29:14 Groq Founder, Jonathan Ross: OpenAI & Anthropic Will Build Their Own Chips & Will NVIDIA Hit $10TRN · 20VC with Harry Stebbings
Sep 29, 2025 positive
Assertion Not publicly verifiable
Ross: Microsoft withheld Azure GPUs because internal usage made more money
“Microsoft in one quarter deployed a bunch of GPUs, and then announced that they weren't going to make them available in Azure because they made more money using them themselves than renting them out.”
Jonathan Ross Sep 29, 2025 ▶ 2:01 Groq Founder, Jonathan Ross: OpenAI & Anthropic Will Build Their Own Chips & Will NVIDIA Hit $10TRN · 20VC with Harry Stebbings
Oct 9, 2025 bullish
Insight
O'Driscoll: OpenAI and Nvidia are repeating Microsoft and Intel's 90s playbook
“Fast forward to today, the company that's dominating everything is OpenAI. They're the Microsoft of today. They have the consumers. They have the eyeballs, right? They're building this new monopoly, and the equivalent of Intel is now Nvidia.”
Rory O'Driscoll Oct 9, 2025 ▶ 6:57 OpenAI's Multi-Billion Deal with AMD & Polymarket, Vercel and Supabase Raise Mega Rounds · 20VC with Harry Stebbings
Oct 9, 2025 negative
Opinion
O'Driscoll: Microsoft enabled OpenAI just as IBM enabled Microsoft 30 years ago
“The role of IBM has been played by Microsoft. They set this Viper in motion, and they've allowed it to exist, and in one sense for a while it looked like Microsoft got a good deal because they got access to OpenAI's technology early on, and they got a little b…”
Rory O'Driscoll Oct 9, 2025 ▶ 7:58 OpenAI's Multi-Billion Deal with AMD & Polymarket, Vercel and Supabase Raise Mega Rounds · 20VC with Harry Stebbings
Oct 17, 2025 negative
Opinion
Zach Lloyd: Microsoft screwed up GitHub Copilot
“I guess, but they, like, I think that they kind of screwed up Copilot.”
Zach Lloyd Oct 17, 2025 ▶ 59:18 20VC: The Startup Adding $1M ARR Every Week | Competing Against OpenAI's Codex and Claude Code: Who Wins | Why Gemini is Failing and GPT-5 Is Winning | Do Margins Matter in a World of AI | The Ugly Truth About AI Coding with Zach Lloyd, Warp
Oct 23, 2025 negative
Opinion
O'Driscoll: Microsoft leadership nailed OpenAI deal, but failed on shipping technology
“I think when all is said, and as I said before, on Microsoft's side, when all is said and done, the shareholders should award medals to Satya, The CFO and their GC and they should hire someone else to do their technology because they haven't shipped, right?”
Rory O'Driscoll Oct 23, 2025 ▶ 42:16 Why VC Today is Worse than 2021 · 20VC with Harry Stebbings
Oct 23, 2025 neutral
Assertion Not checkable as stated
Calacanis: OpenAI capital requirements are 100x Microsoft's initial high-end estimates
“OpenAI needed much more capital than they thought when they started. Microsoft bailed them out in buying 49% of the company. Now they need much more capital than Microsoft thought. Probably two orders of magnitude more than Microsoft's, ah, you know, high-end …”
Jason Lemkin Oct 23, 2025 ▶ 42:50 Why VC Today is Worse than 2021 · 20VC with Harry Stebbings
Oct 27, 2025 negative
Assertion Supported
Cahn: Microsoft walked away from two data centers in early 2025
“Microsoft walked away from two data centers and it sent a message to the market like, hey, we're not stepping up.”
David Cahn Oct 27, 2025 ▶ 23:26 Sequoia Partner, David Cahn on Who Wins in AI, Defence & The New $0–$100M Playbook · 20VC with Harry Stebbings
Oct 30, 2025 neutral
Assertion Supported
O'Driscoll: Microsoft was the only investor to give OpenAI $1B in 2019
“No one else was writing open AI, a billion dollar check in 2019. Microsoft did, and they got that return.”
Rory O'Driscoll Oct 30, 2025 ▶ 8:58 OpenAI Restructuring: Who Wins and Who Loses & Mercor Raises $350M at a $10BN Valuation · 20VC with Harry Stebbings
Oct 30, 2025 positive
Assertion Supported
O'Driscoll: OpenAI finalizes restructuring deals with Microsoft and state regulators
“The big news today is OpenAI cut their deal. They cut their deal with Microsoft, and they cut their deal with the attorneys general, the plural of attorney general of Delaware and California, which means they have been able to implement their restructuring, wh…”
Rory O'Driscoll Oct 30, 2025 ▶ 1:31 OpenAI Restructuring: Who Wins and Who Loses & Mercor Raises $350M at a $10BN Valuation · 20VC with Harry Stebbings
Oct 30, 2025 positive
Assertion Supported
O'Driscoll: Microsoft Achieved a 10x Return on its $13B OpenAI Investment
“They put in thirteen million, thirteen billion dollars. They got a 10 X on their money as of today.”
Rory O'Driscoll Oct 30, 2025 ▶ 5:52 OpenAI Restructuring: Who Wins and Who Loses & Mercor Raises $350M at a $10BN Valuation · 20VC with Harry Stebbings
Nov 13, 2025 neutral
Assertion Not checkable as stated
Lemkin: OpenAI Now Purchases Software Like Traditional B2B Enterprises
“Like open AI is buying like a normal, buying like an Adobe or a Microsoft now.”
Jason Lemkin Nov 13, 2025 ▶ 1:01:57 Michael Burry Shorts NVIDIA and Palantir & Has Defensibility Died in a World of AI? · 20VC with Harry Stebbings
Nov 20, 2025
Assertion Partly supported
Tom Tunguz: Microsoft went public with $50M revenue and $2M fees
“Like I went back and looked at Microsoft, you know, you needed like fifty million in trailing revenue and six quarters of profitability to go public, right? And the cost to take a company public was a couple million bucks.”
Tomasz Tunguz Nov 20, 2025 ▶ 1:04:06 Peter Thiel and Softbank Sell NVIDIA - Why? & Why VC Will Hit $1TRN and The Opening of Retail · 20VC with Harry Stebbings
Nov 27, 2025 positive
Opinion
Rory O'Driscoll: Microsoft-Anthropic-Nvidia compute deal has better fundamentals than peers
“Of all the round tripping deals, I would argue a Microsoft, Entropic, Nvidia deal probably has better principles and upside than most. I mean, some of the other round tripping deals look like they're already, you know, a bit shaky.”
Rory O'Driscoll Nov 27, 2025 ▶ 4:13 Anthropic Raises $30B from Microsoft & NVIDIA & NVIDIA’s Core Business Faces TPU Threat · 20VC with Harry Stebbings
Nov 27, 2025 bullish
Prediction Held up
Rory O'Driscoll: Microsoft compute spending will grow 30% next year
“Is Microsoft going to increase another 30% next year? Is Antropic going to invest in compute? And right now, all those answers to those questions are yes.”
Rory O'Driscoll Nov 27, 2025 ▶ 19:49 Anthropic Raises $30B from Microsoft & NVIDIA & NVIDIA’s Core Business Faces TPU Threat · 20VC with Harry Stebbings
Feb 9, 2026
Insight
Acharya: Incumbents improve legacy categories while startups own new AI categories
“When you have this product cycle and you have a capable incumbent, what happens is they usually make their product better for their existing categories. So Microsoft will make a better word processor than they've ever made. Google will make a better search eng…”
Anish Acharya Feb 9, 2026 ▶ 8:25 a16z, Anish Acharya: Is SaaS Dead? Do Margins Still Matter? Why We Are Not in an AI Bubble? · 20VC with Harry Stebbings
Mar 7, 2026 neutral
Assertion Supported
Green: Apple spends far less on AI CapEx than tech peers
“And, you know, like Apple's spending very little right now, you know, and those other three or four companies are spending insane amounts of money.”
Mitchell Green Mar 7, 2026 ▶ 8:41 Mitchell Green: Why 50% of VCs Should Not Exist · 20VC with Harry Stebbings
Mar 16, 2026 positive
Assertion Partly supported
Intuit TurboTax thrived despite Microsoft's 1990s Office bundling
“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.”
Gokul Rajaram Mar 16, 2026 ▶ 38:50 Gokul Rajaram: How to Analyse for Durability and Defensibility in a World of AI · 20VC with Harry Stebbings
Apr 2, 2026 neutral
Assertion Supported
O'Driscoll: Anthropic reports gross AWS revenue; OpenAI reports net Microsoft revenue
“There was this kind of whole meme of OpenAI reports net on their partner revenue and Entropic reports gross. 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. If A…”
Rory O’Driscoll Apr 2, 2026 ▶ 30:31 OpenAI Kills Sora & Hits $100M ARR on Ads | Oura Going Public & Whoop Raises at $10BN · 20VC with Harry Stebbings
May 7, 2026 bullish
Opinion
O'Driscoll: Investors should buy Amazon and sell Microsoft stock
“You buy Amazon and you sell Microsoft, but these are weekly held.”
Rory O'Driscoll May 7, 2026 ▶ 25:33 Anthropic's Raise & What It Means for Potential IPO? Mag7: Google & Amazon Up, Meta & Microsoft Down · 20VC with Harry Stebbings
May 7, 2026 bearish
Assertion Contradicted
O'Driscoll: Microsoft's revenue growth is flat without its AI initiatives
“Without the AI initiative, Microsoft is flat revenue.”
Rory O'Driscoll May 7, 2026 ▶ 0:41 Anthropic's Raise & What It Means for Potential IPO? Mag7: Google & Amazon Up, Meta & Microsoft Down · 20VC with Harry Stebbings
May 14, 2026 bearish
Opinion
O'Driscoll: Microsoft does not have an AI model worth a damn
“And in Microsoft case, I really wish I even had a model that was worth a damn, which I don't.”
Rory O'Driscoll May 14, 2026 ▶ 14:52 Anthropic Buys Compute From Elon & Commits $200BN to Google | Cerebras IPO | Ramp Raises at $40BN · 20VC with Harry Stebbings
May 16, 2026
Assertion Supported
Microsoft bought Nuance for $20B+ and competed with Abridge
“And the first big competitor for us was Microsoft. They had bought a company called Nuance for 20 some billion some years ago, and they had a product in our category and we still compete with them in the marketplace.”
Shiv Rao May 16, 2026 ▶ 34:04 The Five Year Desert to Product Market Fit & a $5.3BN Valuation with Shiv Rao, Founder @ Abridge · 20VC with Harry Stebbings
May 16, 2026 negative
Opinion
Microsoft obfuscates pricing and overcomplicates enterprise software
“Especially like the Microsofts of the world just obfuscate things so much and make things so complicated.”
Shiv Rao May 16, 2026 ▶ 35:56 The Five Year Desert to Product Market Fit & a $5.3BN Valuation with Shiv Rao, Founder @ Abridge · 20VC with Harry Stebbings
Jun 11, 2026 neutral
Prediction Not checkable as stated
O'Driscoll: Anthropic Sales Force Will Resemble Oracle's Within 5 Years
“The entropic sale force in five years will look like the Oracle sales force, the Microsoft sale force, and the IBM sale force, 50 years ago”
Rory O'Driscoll Jun 11, 2026 ▶ 46:19 SpaceX Launches Largest Ever IPO | OpenAI Files to Go Public | Uber Cuts 23% of HR · 20VC with Harry Stebbings
Jun 11, 2026 negative
Opinion
O'Driscoll: Partnering with OpenAI is no longer a sufficient AI strategy
“This was the end of the period where you could Fool yourself even slightly that your plan for your plan for AI is to partner with open AI. That's just not the answer anymore.”
Rory O'Driscoll Jun 11, 2026 ▶ 1:11:44 SpaceX Launches Largest Ever IPO | OpenAI Files to Go Public | Uber Cuts 23% of HR · 20VC with Harry Stebbings
Jun 29, 2026 negative
Opinion
Shridhar: Single Large Tech Monopolies Like Microsoft and Google Are Fading
“I see the world more and more being not monopolized by single large companies. You know, Microsoft used to be considered a monopoly and everybody was afraid of it. No longer. Google was considered to be the monopoly. No longer.”
K.R. Shridhar Jun 29, 2026 ▶ 23:22 Bloom Energy CEO: Why We Aren’t in an AI Capex Bubble | Energy Sovereignty & The Future of Power · 20VC with Harry Stebbings
Jul 2, 2026 bearish
Opinion
O'Driscoll: Microsoft lacks compelling proprietary AI products beyond OpenAI stake
“So when you zoom out a million miles, Microsoft, which is in the software business, unlike Apple, and therefore can't afford to stay apart from the great AI wars, other than its equity ownership in open AI doesn't have anything compelling to bring to the table…”
Rory O'Driscoll Jul 2, 2026 ▶ 35:09 Coinbase Cuts AI Spend by 50% | Kalshi's $40B Valuation & Impending IPO | The Year for SaaS Roll-Ups · 20VC with Harry Stebbings
Jul 6, 2026 negative
Opinion
Stebbings: Microsoft beats superior startup products through enterprise bundling
“Microsoft has built a business on doing 60 to five to 70% meh products, but with the power of bundling, beat the competitors.”
Harry Stebbings Jul 6, 2026 ▶ 40:39 Why Now is the Time for the App Layer | Why Startups Should be TokenMaxxing | Mike Mignano, USV · 20VC with Harry Stebbings
Jul 6, 2026 bearish
Prediction Held up
Mignano: Incumbent tech companies will constrain employee token spend budgets
“There's too many employees at a Salesforce or I don't know, a Microsoft such that every employee can just have an unlimited token spend budget. So I think we're going to see a lot of those companies start to constrain their spends.”
Mike Mignano Jul 6, 2026 ▶ 22:47 Why Now is the Time for the App Layer | Why Startups Should be TokenMaxxing | Mike Mignano, USV · 20VC with Harry Stebbings
Jul 9, 2026 bearish
Prediction Not checkable as stated
Lemkin: Microsoft's enterprise AI deployment strategy will fail
“I think this is going to fail because I don't think there is enough talent To do what we want to do in the enterprise. The idea makes sense to on a spreadsheet. It makes sense. Sad is smarter than me, but I, my today, my experience is it's going to fail with a…”
Jason Lemkin Jul 9, 2026 ▶ 1:07:56 Enterprises Fear Frontier Models | Sam Altman Offers Trump 5% of OpenAI | DeepSeek Builds Own Chips · 20VC with Harry Stebbings
Jul 9, 2026 bullish
Prediction Not checkable as stated
O'Driscoll: Microsoft will build a massive, lower-margin AI services business
“So summary, I think Microsoft will build a huge services business here if they want to, which also speaks to it won't be nearly as profitable as selling operating systems.”
Rory O'Driscoll Jul 9, 2026 ▶ 1:11:58 Enterprises Fear Frontier Models | Sam Altman Offers Trump 5% of OpenAI | DeepSeek Builds Own Chips · 20VC with Harry Stebbings
Jul 9, 2026 negative
Opinion
O'Driscoll: Microsoft and OpenAI Are in a Stale Marriage Looking for Divorce
“Microsoft owns 30% of OpenAI. If ownership stake resulted in besties, they'd be besties. They're not besties. They're in a stale marriage looking for a divorce, but can't quite pay, you know, pay the tax, right?”
Rory O'Driscoll Jul 9, 2026 ▶ 9:10 Enterprises Fear Frontier Models | Sam Altman Offers Trump 5% of OpenAI | DeepSeek Builds Own Chips · 20VC with Harry Stebbings
Jul 9, 2026 bullish
Prediction Open · timeframe Jul 2027
O'Driscoll: AI capex spending will be stopped by demand, not supply
“This isn't, this spending isn't going to stop because the supply side says stop. Facebook aren't going to say stop. Google isn't going to say stop. Microsoft isn't going to say stop. Really, it boils down to the demand side. As long as, and enterprise customer…”
Rory O'Driscoll Jul 9, 2026 ▶ 41:39 Enterprises Fear Frontier Models | Sam Altman Offers Trump 5% of OpenAI | DeepSeek Builds Own Chips · 20VC with Harry Stebbings
Aug 7, 2026 bearish
Opinion
Frankel: Microsoft Has Done a "Crappy Job" With AI
“So I think Microsoft have done a crappy job of AI generally.”
David Frankel Aug 7, 2026 ▶ 1:04:43 The AI Boom Will Create Enormous Roadkill: Who Wins & Loses? | David Frankel
Aug 20, 2026 neutral
Opinion
O'Driscoll: Owning developers is 100% existential for Microsoft
“I don't think owning the developer is existential for AWS. I definitely don't think it's existential for Meta. It's a hundred percent existential over the medium term for Microsoft.”
Rory O'Driscoll Aug 20, 2026 ▶ 14:20 Stripe's $8B OpenRouter Bet | Anthropic's First Profit & The Math Behind Reaching $600B in Revenue?
Aug 20, 2026 bearish
Opinion
O'Driscoll: GitHub is now a trailing edge product
“And the fact that they've lost that connection with developers, that GitHub is now a trailing edge product, is to me, over the medium term, a pretty significant loss.”
Rory O'Driscoll Aug 20, 2026 ▶ 13:51 Stripe's $8B OpenRouter Bet | Anthropic's First Profit & The Math Behind Reaching $600B in Revenue?
Aug 27, 2026 neutral
Assertion Not checkable as stated
O'Driscoll: Anthropic and OpenAI exist only due to hyperscaler funding
“The only people capable of financing a state-of-the-art frontier model in the United States of America has been the hyperscalers themselves. The only reason Entropic and OpenAI exist is because Microsoft, Google, and Amazon gave them enough money to play becau…”
Rory O'Driscoll Aug 27, 2026 ▶ 10:06 Anthropic's $30T Assumption & OpenAI Confirms IPO | Why Customer Service & Robotics are Overinflated
Aug 29, 2026 bullish
Prediction Not checkable as stated
Reyes: Microsoft Will Win in AI Regardless of Which Model Succeeds
“The biggest thing that Microsoft has going for it is that infra. They own so many of these data centers. They're spending so much on build out. No matter what model runs on top of that, Microsoft is going to win.”
Eno Reyes Aug 29, 2026 ▶ 51:43 Should American Enterprises Work With Open-Source Chinese Models? | Only 10% of Neo-labs survive
Aug 31, 2026 positive
Assertion Not checkable as stated
Katz: ClickHouse powers Microsoft's largest analytical workloads
“Microsoft's one of our power users. We power the largest analytical workloads at Microsoft”
Aaron Katz Aug 31, 2026 ▶ 55:00 ClickHouse CEO: AI Margins Need to Improve | Revenue Concentration Should be a Concern
Sep 5, 2026
Insight
Weitzman: Large-scale AI training requires co-located memory and GPU clusters
“If you want to do large scale training like we do, You need the memory to be co-located with a large cluster of GPUs. I can't just rent from Google or Microsoft or even base 10 and run the size of training that I want because I need a gigantic memory card next…”
Cliff Weitzman Sep 5, 2026 ▶ 3:39 How to Build Your Own Data Center & Why Every Startup Should Do It
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