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This Week in Startups

Microsoft Layoffs, Immigration Blunders, & Office Hours with Jeremy Redman of Airfive | E2127

May 16, 2025
01:04:13

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/

Follow Lon:

X: https://x.com/lons


Follow Alex:

X: https://x.com/alex

LinkedIn: ⁠https://www.linkedin.com/in/alexwilhelm


Follow Jason:

X: https://twitter.com/Jason

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


Check out Jason’s suite of newsletters: https://substack.com/@calacanis


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Substack: https://twistartups.substack.com


Subscribe to the Founder University Podcast: https://www.youtube.com/@founderuniversity1916

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