Microsoft Layoffs, Immigration Blunders, & Office Hours with Jeremy Redman of Airfive | E2127
This Week in Startups
Jason Calacanis
4.4 • 1.3K Ratings
🗓️ 16 May 2025
⏱️ 64 minutes
🧾️ Download transcript
Summary
Today’s show: Microsoft lays off 6,000 employees despite record profits, signaling a ruthless new phase in big tech. Jason, Lon, and Alex discuss what it means for the talent market, why tightening U.S. immigration could cripple startup innovation, and whether AI startup Windsurf is selling too early as OpenAI circles. Plus, Klarna’s AI customer service backfires, IPO momentum returns, and Office Hours with airfive founder Jeremy Redman pitches a bold new prepaid SaaS model.
Timestamps:
(0:00) Episode Teaser(2:40) Why ex-Microsoft staffers are talking smack on Blind(10:08) Atlassian - Head to https://www.atlassian.com/startups/twist to see if you qualify for 50 free seats for 12 months.(15:58) Checking out ElevenLabs’ wild new AI soundboard(20:28) Fidelity Private Shares℠ - Visit https://fidelityprivateshares.com! Mention our podcast and receive 20% off your first-year paid subscription.(24:02) What is Bottom Up TAM and why it isn’t dirty like it sounds(30:10) Google Gemini - It uses AI to help you write, code, and create in one interactive space. Try it at gemini.google.com/canvas.(33:52) Cohere missed revenue estimates but things aren’t THAT bleak!(37:01) Why America NEEDS highly skilled immigrants(43:12) Working the “I Have a Secret” strategy with Jeremy from Airfive
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Links from episode:
EleveLabs Sound Board: https://elevenlabs.io/sound-effects/soundboardLikable: https://likeable.co/airfive: https://airfive.com/
Follow Jeremy:X: https://x.com/thejeremyredmanLinkedIn: https://www.linkedin.com/in/thejeremyredman/
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LinkedIn: https://www.linkedin.com/in/jasoncalacanis
Thank you to our partners:
(10:08) Atlassian - Head to https://www.atlassian.com/startups/twist to see if you qualify for 50 free seats for 12 months.
(20:28) Fidelity Private Shares℠ - Visit https://fidelityprivateshares.com! Mention our podcast and receive 20% off your first-year paid subscription.
(30:10) Google Gemini - It uses AI to help you write, code, and create in one interactive space. Try it at gemini.google.com/canvas.
Great TWIST interviews: Will Guidara, Eoghan McCabe, Steve Huffman, Brian Chesky, Bob Moesta, Aaron Levie, Sophia Amoruso, Reid Hoffman, Frank Slootman, Billy McFarland
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Transcript
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| 0:00.0 | If we make it harder to get a visa to come build here and to hire here, we are literally |
| 0:05.8 | handing the baton of technological leadership to places where those people would have come |
| 0:10.3 | from. |
| 0:11.1 | Like, U.S. technology companies would not be as strong if so many Europeans weren't hopping |
| 0:16.2 | United flights over from London and Paris. |
| 0:18.2 | Not even just Europeans. |
| 0:19.8 | I mean, you know, Indian people and people from China, |
| 0:22.6 | South America. |
| 0:23.6 | All around the world. |
| 0:24.6 | I was just thinking about a couple of companies in particular, but to me, this is seeding |
| 0:29.4 | our competitive advantage as the technology and startup capital of the world. |
| 0:33.0 | That is a mistake. |
| 0:34.2 | That is stupid. |
| 0:35.2 | A huge mistake. |
| 0:36.2 | I want more companies here. |
| 0:37.2 | Yeah. This ourselves in the foot. Yeah. |
| 0:40.4 | This weekend startups is brought to you by Atlassian. From MVP to IPO, Atlassian for startups |
| 0:46.3 | provide your team the right tools to plan, track, and collaborate on work. Head to atlasian.com |
| 0:51.0 | slash startup slash twist to see if you qualify for 50 free seats for 12 months. |
| 0:56.3 | Fidelity Private Shares. If you want the all-in-one equity management platform, FidelityPrivate |
| 1:00.8 | shares has you covered. Visit FidelityPrivate shares.com and mention this podcast for 20% off your |
| 1:06.3 | first year subscription. And Google Gemini. Unlock the power of AI with Google Gemini. |
... |
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