The Biggest Private Funding Round in History | E2256

The Biggest Private Funding Round in History | E2256

Author: Jason Calacanis February 28, 2026 Duration: 1:20:17
This Week in Startups
Technology

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Today’s show:

*$110 billion buys you 15% of OpenAI. Amazon, Nvidia, and SoftBank placed their bets on ChatGPT, which now has 900 million weekly active users and 50 million paying subscribers. Find out why Jason is anticipating the wildest J-Curve swing of all time, and believes we’ve ALREADY hit AGI… it’s just not implemented yet.

Plus a visit from our roving correspondent Nick O’Neill, checking in on the Crypto Chaos in Miami Beach, and hot demos from three young founders.

GUESTS:

Nick O’Neill: https://x.com/chooserich

Everest Chris: https://openclaw.unloopa.com/

Ben Broca: https://polsia.com/

Adi Gabrani: https://makemyclaw.com/

Timestamps:


    00:00 Intro


    01:33 We’re hiring a new producer!


    05:42 OpenAI raised $110 billion


    08:59 Understanding the LLM J-Curve


    00:11:25 Deel - Founders ship faster on Deel. Set up payroll for any country in minutes and get back to building. Visit ⁠https://deel.com/twist⁠ to learn more.


    00:15:02 CRYPTO CHAOS IN MIAMI BEACH!


    00:21:10 Wispr Flow - Stop typing. Dictate with Wispr Flow and send clean, final-draft writing in seconds. Visit ⁠https://wisprflow.ai/twist⁠ to get started for free today.


    00:22:54 Mass layoffs at Block


    00:30:50 Luma AI - Stop guessing and start directing with the all-in-one Dream Machine text-to-video platform. Visit ⁠https://lumalabs.ai/twist⁠ to try The Dream Machine for free.


    00:32:04 AI Scott Adams: The Saga Continues


    00:38:13 Make URLs for local businesses with Unloopa


    00:45:36 Rent a Polsia agent to run your company


    00:58:55 Deploy swarms in 60 seconds with MakeMyClaw


    01:05:05 LAUNCH FEST is coming to SF


    01:55:49 Will Paramount actually buy WBD?


    01:06:58 Why Lon loves “Knight of the 7 Kingdoms”


    01:07:21 On “Neighbors” and First Amendment Warriors


    01:13:43 All about Jason’s favorite chargers

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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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Every week, Jason Calacanis dives headfirst into the swirling vortex of Silicon Valley and global tech with This Week in Startups. It’s a direct line to the conversations shaping our digital future, moving far beyond surface-level news. You’ll hear Jason’s unfiltered analysis on everything from market shifts and media trends to the underlying mechanics of building a business, all delivered with a blend of enthusiasm and seasoned skepticism. The core of this podcast, however, lies in the guests. Jason sits down with the very people driving change-founders who have scaled impossible heights, operators managing daily chaos, and investors who spot trends before they become obvious. These conversations are less like formal interviews and more like insider debriefs, pulling back the curtain on real strategies, painful failures, and unexpected successes. For anyone curious about how technology is built, funded, and ultimately changes the world, this series offers a front-row seat. It’s the context behind the headlines, providing a deeper understanding of the forces at play in startups and technology. Tune in for a consistently engaging and insightful look at the ecosystem, straight from someone who lives and breathes it.
Author: Language: en-us Episodes: 100

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This Week in Startups
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