THE 2025 TWISTY AWARDS! Biggest Trends, Best Guests, Top Name Drops, and more | E2229

THE 2025 TWISTY AWARDS! Biggest Trends, Best Guests, Top Name Drops, and more | E2229

Author: Jason Calacanis December 30, 2025 Duration: 55:48

This Week In Startups is made possible by:


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Today’s show: 


We’re saying goodbye to 2025 with our annual TWISTY Awards, looking back on our favorite pod moments from throughout the year.


Featured clips include Jason’s message to the members of Reddit’s r/AntiWork community…


Why JCal would NEVER work with Sam Altman or OpenAI…


The time that Jason got doxxed and then found the guy responsible on LinkedIn…


Why LA Mayor Karen Bass earned a *disgraziad*…


Alex saying “Yessir!” in a weird way…


And much more classic TWiST content.


See y’all next year!


Timestamps:


(00:00) It’s the final episode of the year: The TWiSTY Awards for our favorite moments and guests of the year


(2:06) The nominees for Best Name Drop


(7:02)2025 in Trends


(9:52) LinkedIn Ads: Start converting your B2B audience into high quality leads today. Launch your first campaign and get $250 FREE when you spend at least $250. Go to http://linkedin.com/thisweekinstartups to claim your credit.


(14:28) The best Jason anecdotes and personal stories


(19:43) Squarespace - Use offer code TWIST to save 10% off your first purchase of a website or domain at https://squarespace.com/twist


(22:28) Our favorite 2025 guests, including Doug Leone, Coffeezilla, Anton Osika, and more


(29:03) The year in Jason Rants


(30:18) Hubspot: Check out the guide “How to Get Your First 100 Customers.” Download it for free at http://clickhubspot.com/twist1


(36:11) Controversial moments and the year’s hottest takes


(44:11) DISGRAZIAD! Here are the most shameful people and companies of 2025


(50:50)Alex’s best/worst Dad Jokes


(54:32) It’s a simple word… groceries


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


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


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Thank you to our partners:


(9:52) LinkedIn Ads: Start converting your B2B audience into high quality leads today. Launch your first campaign and get $250 FREE when you spend at least $250. Go to http://linkedin.com/thisweekinstartups to claim your credit.


(19:43) Squarespace - Use offer code TWIST to save 10% off your first purchase of a website or domain at https://squarespace.com/twist


(30:18) Hubspot: Check out the guide “How to Get Your First 100 Customers.” Download it for free at http://clickhubspot.com/twist1


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.
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