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

December 30, 2025

AI Summary

5 min read

🎙️ The Speakers & Context

The Format: Lighthearted panel awards show recapping 2025 podcast highlights through comedic clips, with high-energy banter and tiebreaker votes.
The Key Players:
- Jason Calacanis (Host/Investor): Angel investor who backed Uber early; hosts This Week in Startups, spotting trends like humanoid robots years ahead via pattern recognition.
- Alex Willems (Co-Host): Podcast co-host with venture insights; curates clips, emphasizing practical takeaways from guests like Lightspeed's fundraise.
- Lon Harris (Editorial Director): Sharp editor who winnows archives; surfaces asymmetric views, like Doug Leone's VC critique, for strategic edge.

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What you'll learn

1 **(00:00) 🎙️ Twisties 2025: Year-End Awards Kickoff**
2 **(01:39) Best Jason Name Drops of 2025**
3 **(07:00) Biggest Trend of 2025**
4 **(14:29) Best Jason Anecdote of 2025**
5 **(22:30) Best Guest of 2025**
6 **(29:05) Best Jason Rant of 2025**
7 **(36:12) Most Controversial Moments of 2025**

+ Full timestamped outline available in the app

Show Notes

This Week In Startups is made possible by:

LinkedIn Ads - http://linkedin.com/thisweekinstartups

Squarespace -https://squarespace.com/twist

Hubspot - http://clickhubspot.com/twist1

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:

(0:00) 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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Subscribe to This Week in Startups on Apple: https://rb.gy/v19fcp