Microsoft
includes Microsoft PowerPoint, Microsoft Excel, Microsoft Word, Microsoft Windows, Microsoft Paint, Microsoft Outlook, Microsoft FrontPage, Microsoft Office, Microsoft Publisher, Microsoft Research, Microsoft Teams, Microsoft Azure and 6 more
28 statements across 19 episodes · 6 bullish · 6 bearish · 18 people on the record · first statement Jan 23, 2017 by Tony Hsieh · said 347 times in 137 episodes since 2016 · across every show →
Mentions by year, the whole family
brought up most by Guy Raz (139), Rich Barton (19), Oliver Kharraz (7), Ben Chestnut (7), Tony Hsieh (6), Melanie Perkins (6), Luis von Ahn (6), Chris Zarou (6)
tap a year for its mentions
2026 19 mentions in 6 episodes 3 per episode
- Serena & Lily: Serena Dugan and Lily Kanter. They Built a $20M Brand—Then One Investor Almost Destroyed It
- Bogg Bag: Kim Vaccarella. The $100 Million Business She Almost Abandoned
- Build-A-Bear: Maxine Clark. A Former Shoe Executive Launches a Stuffed Animal Empire
- NVIDIA: Jensen Huang. From near collapse to becoming the world’s biggest company
- Advice Line with Miguel McKelvey of WeWork
- La Colombe Coffee Roasters: Todd Carmichael and J.P. Iberti. A Brotherhood Built on Coffee (2020)
- every mention in 2026, scene by scene →
2025 70 mentions in 21 episodes 3 per episode
- Skype and Kazaa: Niklas Zennström
- Exploding Kittens: Elan Lee. How cat-themed Russian Roulette changed game night forever
- Figma: Dylan Field
- UNTUCKit: Chris Riccobono
- Tecovas: Paul Hedrick
- (July 2021) Ben Chestnut: From Side Business to $12 Billion – The Accidental Triumph of Mailchimp
- Talenti: Josh Hochschuler
- Pressbox and Tide Cleaners: Vijen Patel. The $1.99 Gamble That Built a National Brand
- 13 more episodes that year, every mention in 2025 →
2024 26 mentions in 14 episodes 2 per episode
- Viator: Rod Cuthbert
- Groupon and Descript: Andrew Mason
- Building a decarbonization army with Shashank Samala of Heirloom
- Advice Line: Growing Beyond Your Niche
- AI is smarter than you think with Shane Legg of Google DeepMind
- Sonos: John MacFarlane
- Liquid Death: Mike Cessario
- BARK: Matt Meeker
- 6 more episodes that year, every mention in 2024 →
2023 30 mentions in 14 episodes 2 per episode
- reCAPTCHA and Duolingo: Luis von Ahn (2020)
- Spikeball: Chris Ruder
- Priority Bicycles: Dave Weiner
- When AI is your personal tutor with Sal Khan of Khan Academy
- Chomps: Pete Maldonado and Rashid Ali
- Charging up the electric vehicle market with RJ Scaringe of Rivian
- Sir Kensington's: Scott Norton and Mark Ramadan
- Leading through radical change with Julia Hartz of Eventbrite
- 6 more episodes that year, every mention in 2023 →
2022 30 mentions in 17 episodes 2 per episode
2021 60 mentions in 17 episodes 4 per episode
2020 41 mentions in 19 episodes 2 per episode
- Zocdoc: Oliver Kharraz
- reCAPTCHA and Duolingo: Luis von Ahn
- Calendly: Tope Awotona
- How I Built Resilience: Morra Aarons-Mele of Women Online
- Dropbox: Drew Houston
- Remembering Tony Hsieh of Zappos
- Sub Pop Records: Bruce Pavitt and Jonathan Poneman
- Wikipedia: Jimmy Wales (2018)
- 11 more episodes that year, every mention in 2020 →
2019 31 mentions in 13 episodes 2 per episode
- Canva: Melanie Perkins
- Live Episode! Walker & Company: Tristan Walker
- Live Episode! Luke's Lobster: Luke Holden and Ben Conniff
- Compaq Computers: Rod Canion (2019)
- Logic: Logic & Chris Zarou
- Squarespace: Anthony Casalena
- Zappos: Tony Hsieh (2017)
- Live Episode! OtterBox: Curt Richardson
- 5 more episodes that year, every mention in 2019 →
2018 12 mentions in 6 episodes 2 per episode
2017 26 mentions in 8 episodes 3 per episode
2016 2 mentions in 2 episodes 1 per episode
Everything said about Microsoft, oldest first
Jan 23, 2017
Jan 23, 2017
Tony Hsieh Walked Away From 1.5 Years of Unvested Microsoft Stock
“Well, in Silicon Valley, usually there's a four-year, what's known as a four-year vesting for your stock, and I'd only been there for two and a half years, so really had to stay for another year and a half after Microsoft acquired us in order to get the full a…”
Apr 3, 2017
Jan 15, 2018 neutral
Hoffman: There is a very low probability I will start another company
“I think so. You know, it's kind of this never say never thing, but you know, there's a wide variety of really important organizations that I sit on the boards of. Microsoft, obviously, one of them. Airbnb, Convoy there's a set of these different you know, kind…”
May 20, 2019
Tony Hsieh walked away from 18 months of Microsoft stock vesting
“Well, in Silicon Valley, usually there's a four-year, what's known as a four-year investing for your stock, and I'd only been there for two and a half years, so really had to stay for another year and a half after Microsoft acquired us in order to get the full…”
May 20, 2019
LinkExchange grew to 100 employees and sold to Microsoft for $265 million
“Over two and a half years, we ended up growing the company, which was called Link Exchange, to about a hundred or so people. And then ultimately ended up selling the company to Microsoft in 1998 for two hundred sixty five million.”
Nov 30, 2020 positive
Hsieh: LinkExchange Grew to 100 People and Sold to Microsoft for $265M
“Yeah, over two and a half years, we ended up growing the company, which was called Link Exchange, to about a hundred or so people. And then ultimately ended up selling the company to Microsoft in 1998 for two hundred sixty five million.”
Nov 30, 2020 neutral
Hsieh: Walked Away from Unvested Stock Following Microsoft Acquisition
“Well, in Silicon Valley, usually there's a four-year, what's known as a four-year vesting for your stock, and I'd only been there for two and a half years, so really had to stay for another year and a half after Microsoft acquired us in order to get the full a…”
Dec 14, 2020
Riot's early lead developer held secret pitch meetings with Sony and Microsoft
“So that was a really contentious moment in, in the office where it turned out that we heard that this individual was having meetings with, you know, Sony and Microsoft to try to go build games for, you know, the PlayStation network or the burgeoning Xbox marke…”
Jun 14, 2021
Barton's Microsoft team secretly pivoted Expedia from MSN to the open web
“We were building for MSN, which we recognized wasn't going to probably succeed as a platform. And so we quietly pivoted to building a web app and we kind of didn't tell anybody. And so we launched, we never launched on MSN, we launched on the broad internet.”
Jun 14, 2021 positive
Barton pitched Bill Gates on a graphical online travel booking service
“I showed him Prodigy, and it was all a command line really ugly thing, but I talked about how I could see him doing a Kind of a Windows version of this and giving it to consumers could be a complete game changer for consumer empowerment. And he agreed, yeah.”
Jun 14, 2021
Barton: Microsoft formed a travel agency to access airline reservation systems
“We knew that if we started a travel agency, that from an equal access perspective, we ought to be able to plug into these electron, these big mainframe based reservation systems that ran the industry and act like a travel agent. And if we got discriminated aga…”
Jun 14, 2021
Barton: Egghead Software Held First Midnight Madness Sale for MS-DOS 5
“MS-DOS-V was the first time that Egghead Software, which was the big retailer, software retailer at the time, had ever seen, they ran a midnight madness sale on the first day that the DOS-V upgrade was released, and they had people camping out and lining up ou…”
Jul 26, 2021 negative
Reffkin: Traditional brokerages pocketed profits instead of investing in R&D
“This has been a model for over a hundred years where brokerage firms had taken the profits from the agents, split it between the manager, the manager's manager, and the owner, and on balance that owner put in their pocket and then they went on vacation. But wh…”
Sep 6, 2021 positive
Lynda.com secured massive enterprise adoption entirely through organic employee demand
“A lot of people who taught web design and Photoshop were using our courses, and they were bringing it into their schools and into their companies, so we'd be installed in all of Apple, all of Adobe, all of Microsoft, all of Google, and the employees were start…”
Nov 1, 2021 negative
Mar 7, 2022
Citron: Discord rejected acquisition offers because the team wanted to keep building
“The interesting thing about the experience we went through earlier this year, you know, I can't comment on any specific companies, but it was a really crystallizing moment because, you know, I was talking to some of the folks on my team about sort of what path…”
Jul 7, 2022 neutral
Donnel Baird: Goldman and Microsoft debt provides most of BlocPower's capital
“The majority of the capital that we've raised is actually from Goldman and Microsoft, and we have to repay them. And so, every dollar that we take in from them has to have a plan where we can give them four, five, six, seven percent return. Out of the profits …”
Feb 8, 2024 bullish
Feb 19, 2024 negative
Major 1990s Software Giants Refused Internet Sales Over Channel Conflict Fears
“The folks that kind of were the gatekeepers at the big software companies at that time, Microsoft, Borland, Lotus Weren't interested in selling their software over the internet. They were more worried about hurting their sales through the conventional channels…”
Mar 17, 2025 neutral
Mar 17, 2025 bearish
Mar 17, 2025 neutral
Jun 16, 2025
Jun 16, 2025 positive
Microsoft threatened to drop Figma unless it started charging for its product
“One of their design leaders came to our office and spent some real time with me, and he I think was sussing out, like, is, are they serious or not? And at the end, he goes, you know, your tool is free. I said, I know, I, we gotta make some improvements, I thin…”
Nov 3, 2025 positive
Dec 22, 2025 negative
May 18, 2026 negative
Huang: NVIDIA's initial graphics architecture was incompatible with Microsoft's DirectX API
“And Microsoft is about to announce Windows 95. And Windows 95 has a API called DirectX, and DirectX does it the right way, and we were incompatible with DirectX. And so anyways, we chose some approaches that were just fundamentally wrong.”