THE 2025 TWISTY AWARDS! Biggest Trends, Best Guests, Top Name Drops, and more | E2229
This Week in Startups
Jason Calacanis
4.2 • 1.4K Ratings
🗓️ 30 December 2025
⏱️ 56 minutes
🧾️ Download transcript
Summary
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:
(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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Follow Lon:
X: https://x.com/lons
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Follow Alex:
X: https://x.com/alex
LinkedIn: https://www.linkedin.com/in/alexwilhelm/
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Follow Jason:
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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
Transcript
Click on a timestamp to play from that location
| 0:00.0 | It's the Twisties. |
| 0:01.5 | For me and my friends, Ben Stiller, Timothy, Chalame, and my brother, Josh, I'm talking in |
| 0:05.6 | my Brooklyn high speed, but I got to go to F1. |
| 0:08.9 | We're going to have job destruction. |
| 0:10.3 | Everybody agrees on that. |
| 0:12.3 | The only thing people don't agree on is the timeline, and if we can create new jobs in that |
| 0:17.8 | time period. |
| 0:18.3 | I believe Optimus is going to be the greatest product ever created |
| 0:22.6 | by humanity, including the wheel in this, obviously. It is going to be the most successful |
| 0:27.2 | product in history. And people won't forget a Tesla ever made cars. A bold prediction. |
| 0:32.9 | I said, so you're married. I said, I tell you what, we'll talk to your wife. Tell what you did. |
| 0:37.4 | And ask her what she thinks is the best thing for you to do. I get an apology letter from him with his wife, CeC. That is, I've once the most interesting and useless piece of information that has ever been given out on this show. That, to me, is the best moment, yeah, I shouldn't say this. This was one of my favorite episodes of the whole year, just to get personal. Okay, I have to go with, because of the twisty title. |
| 0:57.7 | This Week in Startups is brought to you by HubSpot. |
| 1:00.9 | Check out the guide how to get your first 100 customers. |
| 1:04.6 | Download it for free at click HubSpot.com slash Twist 1. |
| 1:09.3 | Squarespace. |
| 1:10.1 | Turn your idea into a beautiful website. Go to |
| 1:12.9 | Squarespace.com slash twist for a free trial. When you're ready to launch, use offer |
| 1:17.4 | code twist to save 10% off your first purchase of a website or domain. LinkedIn ads. Start |
| 1:23.8 | converting your B2B audience into high-quality leads today. |
| 1:32.7 | Launch your first campaign and get $250 free when you spend at least $250. |
| 1:37.5 | Go to LinkedIn.com slash this weekend startups to claim your credit. |
... |
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