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

Summary

Podcast Summary: "THE 2025 TWISTY AWARDS! Biggest Trends, Best Guests, Top Name Drops, and More"

Podcast: This Week in Startups
Host: Jason Calacanis
Episode: E2229
Date: December 30, 2025

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Overview

In this special year-end episode, Jason Calacanis and co-hosts Lon Harris and Alex Wilhelm present the "Twisty Awards" — a playful, rapid-fire review of the biggest trends, best guests, top moments, and the most memorable episodes from "This Week in Startups" in 2025. The team debates, reminisces, and often jokes about the standout moments, providing both nostalgia and critical insight into the past year's tech and startup landscape.

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Key Discussion Points & Insights

1. Best Name Drop of 2025

• Nominees stroll down celebrity lane: Jason recounts run-ins and hangouts with figures like Elon Musk, Ben Stiller, Timothy Chalamet, Sergey Brin, and Tony Robbins.
• Highlight: The F1 race poker table with "basically the greatest table ever seen," featuring Timothy Chalamet, Travis (Uber), Chamath, David Friedberg, Shane from Polymarket, and more.
  • Quote (Jason, 05:02):
    “We had a nice poker game with Timothy Chalamet.”
• Court-side Knicks seats story also wins praise for both the names dropped and a dig at Detroit ticket prices.
• Winner: The F1 event edges out as the "deluxe name drop" for the sheer density and caliber of luminaries.

2. Biggest Trends of 2025

• Major themes debated:
  • The return of M&A (mergers and acquisitions) post-Lina Khan era.
  • AI-driven job displacement and looming youth unemployment crisis.
  • The arrival/rise of humanoid robots (Tesla's Optimus, etc.)
• Debate between hosts: Each panelist votes for a different trend, tying up the results.
  • Jason’s tie-breaker: M&A resurgence is crowned the most acutely “2025 trend.”
  • Quote (Jason, 07:29):
    “The wrath of Lina Khan ending and the Trump M and A bonanza begins...We need to let M and A rip or else we will not have risk capital at work. Let it rip.”
• Second place: Both AI job displacement and humanoid robots recognized as massive, soon-to-land phenomena.

3. Best Jason Anecdote

• Nominees:
  1. Jason confronts a LinkedIn doxxer — "Hey, dum dum, talk to your wife." (15:05–16:53)
  2. Jason’s guidance counselor origin story — being told he’d never get into college, and how that drove him.
  3. Private jet etiquette lessons — the four unspoken rules of flying with VIPs.
• Winner: The doxing saga, chosen for both its drama and Jason’s unorthodox but diplomatic resolution.
  • Quote (Jason, 16:36):
    “I said, so you’re married. I said, I tell you what, go talk to your wife, tell her what you did and ask her what she thinks is the best thing for you to do. I get an apology letter from him with his wife CC.”

4. Best Guest of 2025

• Nominees:
  • Doug Leone (Sequoia Capital): Venture capital's “sham/scam” and honest industry critique.
  • Coffeezilla: Dissecting meme coin scams, fraud, and crypto regulation.
  • Anton Osika (Lovable): The future of software, single-founder SaaS, and AI’s place in product development.
  • Rahul Vohra (Superhuman/Grammarly) & Vlad Tenev (Robinhood): Scaling, design culture, and leadership.
• Winner: Doug Leone for his candid, "hand grenades behind him" style honesty about VC incentives and greed.
  • Quote (Doug Leone via Jason, 22:57):
    “First of all, the sham of the scam that is called venture capital…We get paid…If we lose the money, so what? If we make money, we get the key...You wonder why the balance between greed and fear always lean towards greed.”

5. Best Jason Rant

• Rants in contention:
  1. Anti-remote work and pro-office socialization for young professionals.
  2. Movie theaters pricing and experience (AMCs, 3D, food costs).
  3. The security and privacy debacle with the “T app.”
  4. Mark Zuckerberg's decision-making — "You can’t trust Zuck."
• Winner: The enduring Zuck/META rant, praised for both passion and historical continuity ("since the beginning, you can't trust Zuckerberg.").
  • Quote (Jason, 35:01):
    “He needs an ombudsman...Zuckerberg does not have anybody around him telling him when they're doing stupid. This is a dangerous place for somebody with that much power to have.”

6. Most Controversial Moments

• Show’s spiciest moments include:
  • Jason’s argument against rich people piloting experimental vehicles.
  • Katy Perry's infamous Blue Origin spaceflight performance ("What a Wonderful World" in zero-G).
  • Podcast rivalry with Kara Swisher—"after $10 million, money doesn't matter."
  • Jason’s public and viral warning: "Never work with Sam Altman and OpenAI."
• Winner: The Katy Perry-in-space segment, for sheer entertainment, irreverence, and graphic rocket humor.
  • Quote (Jason, 39:11): “Rockets inherently look like penises. And then this one is designed to just look like a circumcised penis. Oh, God.”

7. Desgraciad of the Year

• “Disgraziad” defined: Jason’s Brooklyn-derived insult for entities that have deeply disappointed.
• Nominees:
  • Apple/Tim Cook: “Where are the new ideas??”
  • Vail Ski Resorts: Management and stock losses.
  • LA Mayor Karen Bass: Crisis leadership.
  • Bank of America mobile app (and legacy banking UX).
• Winner: Apple, for the loss of magic post-Jobs and underwhelming innovation since the iPhone/iPad golden years.
  • Quote (Jason, 44:37): “It is disgraceful that they can't come up with something super compelling other than this, like, tiny, thin phone...the camera sucks so bad.”

8. Best Alex Dad Jokes

• Nominees: Alex’s penchant for bad jokes, wordplay, and comedic timing.
  1. “Capacious” as the “c-word” he's allowed to call Jason.
  2. Raunchy stoner comedies as “my personality after 8pm.”
  3. “Please take everyone out to lunch because you have enough cash for that?” (re: Lightspeed Ventures $9B fund)
  4. Honorable mention: The enthusiastic “Yes, sir!” for Figma’s public filing.
• Winner: The “Yes, sir!” Figma moment, unanimously beloved by the team for its wholesome delivery.
  • Quote (Alex, 53:57): “Yes, sir, it's Figma.”

9. Bonus: Trump Impressions

• Most memorable Jason Trump impression:
  • “It's just a word. Groceries.” (55:10)

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Notable Quotes & Moments

• On AI and Job Market Anxiety:
  “We're going to have job destruction. Everybody agrees on that... if we can create new jobs in that time period.” — Jason (08:19)

• On the ‘T app’ privacy bomb:
  “They didn’t encrypt the driver’s licenses, pictures and reviews of former dates or boyfriends that women were leaving in this app. So this is incredibly damaging on, like, multiple vectors.” — Jason (33:12)

• On private jet etiquette:
  “You let the principal decide where they're going to sit first... you wait for the principal to pick their seat…” — Jason (18:38)

• On podcasting and old rivalries:
  “All In makes much, much, much more money than Pivot does ... I think a little of this might be reverse jealousy.” — Jason (40:10)

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Timestamps for Key Segments

• Name Drops: 02:16–06:17
• Trends of the Year: 07:03–14:01
• Best Jason Anecdote: 14:29–16:53
• Best Guest: 22:57–29:00
• Best Rant: 29:30–36:12
• Most Controversial Moments: 36:20–43:57
• Disgraciad of the Year: 44:08–50:50
• Alex Dad Jokes: 51:21–54:17
• Memorable Moments/Outro: 54:39–55:44

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Tone & Style

The episode is self-aware, irreverent, and energetic — blending sentimental reflection, inside jokes, candid industry critique, and generous doses of friendly ribbing. The hosts’ chemistry and history together is palpable, with Jason’s trademark bluntness and Alex and Lon’s pop culture-savvy commentary keeping things lively.

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Summary Takeaway

The 2025 "Twisty Awards" encapsulated not only the hottest stories and trends in tech, startups, and AI, but also the camaraderie and sharp humor that define the show. Whether for the best celebrity run-in, the "disgraziad" of the year, the most viral rants, or the most groan-worthy dad joke, this episode doubled as a yearbook for devoted listeners and a lively tech industry snapshot for newcomers.

Transcript

[A]

It's the twisties for me and my friends Ben Stiller, Timothy Chalamet and my brother Josh. I'm talking in my Brooklyn high speed, but I got to go to F1. We're going to have job destruction. Everybody agrees on that. The, the only thing people don't agree on is the timeline. And if we can create new jobs in that time period, I believe Optimus is going to be the greatest product ever created by humanity, including the wheel in this. Obviously it is going to be the most successful product in history and people will forget that Tesla ever made cars.

[B]

A bold prediction.

[A]

I said, so you're married. I said, I tell you what, go talk to your wife, tell her what you did and ask her what she thinks is the best thing for you to do. I get an apology letter from him with his wife C.C.

[C]

That is at once the most interesting and useless piece of information that has ever been given out on this show.

[A]

That's. That to me is the best moment. Yeah, I shouldn't say this.

[B]

This was one of my favorite episodes of the whole year. Just to get personal.

[A]

Okay, I have to go with. Because of the twisty title, this week in startups is brought to you by HubSpot. Check out the guide how to get your first 100 customers. Download it for free at clickhubspot.com twist1 squarespace Turn your idea into a beautiful website. Go to squarespace.com twist for a free trial. When you're ready to launch, use offer code twist to save 10% off your first purchase of a website or domain. 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 LinkedIn.com thisweekinstartups to claim your credit. All right everybody, welcome back to our year end episode. It's the twisties.

[B]

Woo.

[A]

Twisties. 2020 25. These are the best of awards. Lon is here. Lon Harris, our editorial director and of course my co host Alex Willem.

[C]

Hey, hey, hey, hey, hey.

[A]

Let's get started.

[B]

Now these are going to air a little after Christmas, but I'm still wearing my most festive Christmas sweater. I figured last episode of the year, why not? So our first category, the best Jason name drops of 2025. There were a lot of these. I had to winnow it down to just the top three.

[A]

That's hilarious by the way. I don't know the categories or the nominees. I am coming in completely cold. So this is A new category, but.

[B]

Okay, here we go.

[A]

Best name drop. I can imagine. Timothee Chalamet, Elon Musk, Trump. I mean, there's so many possible.

[B]

You've left a few names off, but you got. You guessed. You correctly guessed a few of them. Okay, so I see this first clip. The first clip. This is Jason discussing his experiences hanging out at the XAI offices. Let's take a look.

[C]

I didn't realize you've gone WWE unless nerdy.

[A]

So, yeah, XAI on Saturdays, you know, we push code. We get the new models out. Brock 3.5. And then we. We left. We left. But I met a bunch of great team members over at X. I spent the day there with Elon and some friends. That's the original from Roman. Roman's a great guy. Working on cool stuff over there at X. And Xai.

[B]

Hanging out at XAI with Elon Musk. Number one name drop of the year. All right, we got another one coming up at you. Here's number two, A little story about courtside seats for a big Knicks game featuring some very special guests. Let's take a look at that one.

[A]

I bought courtside seats for me and my friends Ben Stiller, Timothy Chalamet, and my brother Josh, and we all went to the game.

[B]

What a squad.

[A]

I kid you not. I'm actually friends with Ben Stiller. I'm not with Timothy Chalamet. And so I was like, dming him after the second game. We're in the playoffs now. And I said, hey, are you going to the game? Because courtside seats in Detroit are basically, like, $17. So I was like, ben, hey, go to the game. And I got to score side seats. And he's like, oh, yeah, I want to go. Hilarious. Okay.

[C]

Knew that would be in there.

[B]

We got. We actually got Timothy Chalamet gets double shout outs. Our final also features him. This is a story about hanging out at F1 with some notable. Notable notables. Let's take a look at that one.

[A]

And I'm in Miami. I gotta catch a fly right after this. You're not xbe. I am talking in my Brooklyn high speed, but I got to go to F1. I'm here for the Owen F1 Spectacular. I had a great time. We did a couple of interviews. We had, like, a stage show here in Miami, some great speakers. Nico, the guy who won F1, and I guess, like, 10 years ago or something, he was on the program. He's now in Venture capital. We had Sergey Brin as a surprise guest. We had Tony Robbins on the program, Antonio Grastos came to talk a little bit about. A little bit about Doge and what he's working on. And then who am I missing? Oh, oh, Mayor Francis Suarez came. Yeah, the mayor was there. So that'll all be coming out from all in in a week or two. And I went to my first F1 race, Alex, which was exciting. And I was in the trophy house, which is the right at the turn at the finish line. I was like right there. And we had a poker table set up. So me and my besties played cards. Quite a lineup at F1. We had myself, Shane from Polymarket, shout out to Polymarket. We love Polymarket. Travis from Uber, Chamath obviously from all in, and David Freeberg from All In. That's a picture from the poker table, basically. But we were right there. I mean, it was the greatest table ever seen thanks to my friend Ford who runs Trophy House. He gave us one of the three floors of their thing and we had a great All In VIP party. And yeah, Travis Mee. Who are the other besties? Chamath Freiberg, Shane from Polymarket, and Timothy Chalamet and a couple of his friends. So we had a nice poker game with Timothy Chalamet.

[C]

I'm still jealous.

[B]

Timmy Tim is the number one name drop of the year. He got in there multiple times.

[A]

It's interesting. You know, Timothy Chalamet is a social media machine when you think about it. Integrated himself into the Knicks. He's got, you know, he was on the sphere today. He's got some hip hop stuff going on. He's everywhere. He is a machine.

[B]

He's got this ping pong table tennis movie out. Marty supreme in the. The publicity for this movie has been non stop for like a month now. He's everywhere promoting this movie, even on All In.

[A]

In this week in Startup. So here we go. I don't. I mean, you guys tell me who, who wins? What was the name drop of the year in your minds? You guys pick.

[C]

Lon, you go first, I'll go second.

[B]

Oh, I mean, to me, I think the clip was that last One we showed F1. So many names. You got Shane from Polymarket, Nico Rosberg, former F1 champion, Sergey Brin, Tony Robbins, J. Timothy Chalamet.

[A]

Yeah, that was a big drop.

[B]

That's, that's a, that's a, that's a deluxe name drop right there. I'm.

[C]

I'm gonna go with courtside seats because not only did Jason managed to name drop a lot in there, he also managed to get in a massive dig at Detroit tickets that are like $4 fair. I appreciate the, the high mindedness and the low mindedness at the same time.

[A]

It's literally a jump ball here. I guess I have to be the tiebreaker. I'll go with F1. I'll get go with F1 only because having a Sergey Brin, Tony Robbins drop complimenting and bookending a Timothy Chalamet is like that's a jcal like 6 or 7 name drop. Only person who's name dropping more than me is obviously Hellmuth. Phil Hellmuth who was there. But I don't drop Phil Hellmuth because then it becomes too meta. Let's keep moving through the bestie awards. Well done.

[B]

All right, up next, we got the biggest trend of 2025 and I've got a clip, a clip from each to represent. These were things that came up on multiple, multiple episodes that we discussed throughout the year. And I just had to pick out a good clip. The first one, the wrath of Lena Khan slash the return of M and A, a huge theme for the year 2025. Let's take a look at a sample clip.

[A]

If we had more M and A, which over the weekend, I'm not gonna say which company. We were informed one of our portfolio companies was getting bought. This is a great transaction, apparently we'll see the devils in the details. But another great transaction for us if it goes through and it looks like it's going to. So the wrath of Lina Khan ending and the Trump M and A bonanza begins, which, you know, I would just say is a Republican M and A bonanza and hopefully less regulation on Eminem. We need to let M and A rip or else we will not have risk capital at work. Let it rip. President J.D. lance. I mean Trump.

[B]

So that was march, that was May 12th of this year. A theme that continued throughout the rest of the year.

[A]

2025.

[B]

Up next, the second major trend of 2025, AI job displacement. And here is a clip from June with Jason predicting a youth unemployment crisis that may in fact already be upon us. Let's take a look.

[A]

We're going to have job destruction. Everybody agrees on that. The, the only thing people don't agree on is the timeline. And if we can create new jobs in that time period. And then Philippe had something, you know, I think, I think it was Philippe who just said something really interesting about like people have to also be motivated to start jobs, to create jobs. And that's going to be very interesting, I think, very interesting moment. In time where, you know, group of five, 10 people, like when you graduated from college or I did, when I graduated, there weren't a lot of jobs in 94, 92, 93 were coming out of like a recession and everything. Some people didn't get jobs. They just stayed at home. I think that might be a trend that we're going to see. Young people without jobs.

[C]

Yeah. So that means we're looking at job destruction now from two different perspectives. Because we talked a lot on the show, Jason, about our concern that AI is going to automate early career positions in law and programming and other kind of like knowledge heavy industries. But now if we take away the gig economy safety net as well, I mean, that does really give people right out of college or just right out of high school, frankly, a pretty limited set of gigs. That's, that's worrying.

[A]

Well, and that's happened to white collar too. So, you know, we, we've seen in big tech that they're like, yeah, we're not going to hire young people because we don't have to. We don't want to have to train them. And the time it takes to train a young person versus the time it takes to automate some amount of work at your job just might be easy to automate it. So I think this is the tension that's going to become very real in the next, you know, five years. If you're selling a business to business product, you're looking to reach product professional customers who are doing business. And the question you have to ask yourself is, where do those business leaders spend their time? And the answer is obvious. LinkedIn. And these are the real decision makers. So when you advertise on LinkedIn, you're not wasting your money. You're going to target your ads based on job title, based on industry, based on skills. So maybe you want a CFO in the technology space who has been in their job for five years. Right. You want to zero in on those demographics and behaviors. LinkedIn has over a billion members and 10 million of them are C suite executives. They're going to help you reach exactly the right person with the authority to pay for your product. Right. Go right to the top. Use LinkedIn. And we've got a special offer just for twist listeners. Launch your first campaign and get $250 free. When you spend at least $250, go to LinkedIn.com thisweekinstartups to claim your credit.

[C]

Well, yep, guys, I think that's, it's coming pretty darn true. But lon what is our third trend for the year?

[B]

Third and final major trend. This was one that I saw multiple, multiple clips going back through the entire archive. The arrival of humanoid robots. Here's a clip from September 2nd with Jason predicting that one of these humanoid robot projects will, will become the world's greatest product.

[A]

I believe Optimus is going to be the greatest product ever created by humanity. Including the wheel in this. Obviously it is going to be the most successful product in history and people will forget that Tesla ever made cars. In another 10 or 20 years. People are going to say remember the company Sony? They used to make rice cookers and hot blankets, heating blankets. And there was this, I think the first product was a rice cooker and a heating blanket. What did you think it was? The Walkman?

[C]

Well, I was just thinking back to like the 90s and I was like yeah, I realized well, Bantrain that I was off by a couple of decades.

[A]

Anyways, keep going. Rice cookers, blankets, fantastic, right? This could be like we could be sitting here thinking like all these incredible cars, EV revolution, self driving, all a footnote. These robots are going to become the best selling products in the history of humanity and they're going to change the world more than the Internet.

[B]

A bold prediction.

[C]

Top trend here. Lon, why don't I go first this time in the you, you know, in the spirit of fairness do it. I think no more jobs is the most important trend of the year. Even though M and A is getting better and it's good for everybody. Even though we all like robots. I think the no more jobs thing is going to be the most salient point that lands the quickest and therefore it's the most important.

[B]

See I, I'm, I'm, I'm going to count to you. I think humanoid robots we, we actually for all in a few weeks ago we were talking about because at the, at the all in holiday party they pick what they think are like the biggest trends right now. And so we were sort of discussing that a few weeks ago and I also said humanoid robots for that one. I just feel like you know we had the Sunday robotics Mimo bot. We had Neo from 1X. I feel like all, all of a sudden this year figure had those really impressive demos where the bot is sorting packages. I just feel like all of a sudden this year we're seeing all these different companies and they're reaching critical mass.

[A]

But this is the trend of 2020 25. How do we framing the twisty award title the twistiest.

[B]

The this is the biggest trend of 2025.

[A]

Ah, see, that's interesting because it is of 2025 and I.

[B]

So my choices are M and A returns. Lina Khan is gone. AI job displacement. The rise of the humanoid robot.

[A]

Okay, I have to go with. Because of the twisty title that M and A is the one that most acutely landed in 2025.

[B]

Fair enough.

[A]

Job displacement feels like it'. Year. Rob Robots and AI job displacement certainly are what we're talking about, but I think it will land in 26. I think M&A landed 2025. We had so many M and A deals. I got to go M and A. So wait, do we each pick a. Do we each pick a different.

[C]

Yeah, so it's now tied for each of the one.

[B]

We each picked a different one. But I think it's your show. You're the host.

[A]

All right, great. We'll go with mine. End of Lena Kahn, and I'll stop talking about it. Everybody's upset that I keep talking about. I will not bring. I will not say Lina Khan in the Wrath of Lina Khan in 26. It'll just be Trump's M and A train. The Trump. The M and A Trump train. All aboard.

[C]

Can we do a polymarket on how long it takes Jason to say the Wrath of Lina Khan.

[B]

The Wrath of Lina Khan?

[A]

I won't do it. I'll put all my money behind it, and I do it.

[B]

Up next, the category is the best Jason Anecdote of 2025. I rounded up some of our favorite Jason star story. Sometimes Jason likes to go on a little tangent, tell us a little story from his exciting life in technology. So first up, this is from last holiday season. This was one of the first episodes of 2025. Jason tells the story of how he found a guy on LinkedIn who had doxed him.

[C]

Let's take a look as you watch this clip. Appreciate the upgrades we made to the lighting on the show as you watch this clip.

[B]

Oh, yes, this is true. It's a little dark.

[A]

I had somebody. I'll just tell a little story here. I had somebody dox me based on a picture of, like, my backyard. This person. I'll just tell the story. Okay. Person is upset because of something I said on the show. They decide to dox me. They decide to put my primary residence is worth $10 million. What do I know? Blah, blah, blah. And you know how they got my photo? They went back two years when I took a picture of the tree line in my backyard. They reverse image searched it and they tweeted it this is on July 4th weekend. I say to the guy, I looked the guy up, I google search him because I have security protocols. So now I got to get the security company involved to find out if this person's gonna jump my fence. Right, right. Okay, you know, I have security, I have guns, I got cameras, I got alarms, I have a security detail. I mean, I got it all. I don't talk about it. I'll talk about here for Bruce. I finally got on LinkedIn. I look at the company. Hey, that company looks very familiar to me. I click the company. I know the CEO who we work for. I screenshot it, checkmate, send it to him. And I say, hey, dipshit, first of all, happy Independence Day. Number two. Your boss and I had drinks at this conference, play cards, yada yada. And I'm about to email them what you just did. What do you think their response is going to be to you doxing me? He says, are you going to do that? I said, well, why don't you call me? So I get off the treadmill July 4th, they say, hey, dumb dumb, do you realize how dangerous this is for me? I have kids. I know you don't have kids and I know you're probably 24 year old. And he goes, no, I'm actually married. I just had my first kid. I said, oh, that's great, what a blessing. How old your kid this is? Four weeks. I said, you got a four week old kid, it's July 4th and you're doxing me knowing that I could have my kids get attacked. It's serious shit here, kid. And I said, so you're married. I said, I tell you what, go talk to your wife, tell her what you did and ask her what she thinks is the best thing for you to do. I get an apology letter from him with his wife, C.C.

[C]

Yeah, they're don't you think?

[A]

And I said, consider it lesson learned, water under the bridge. I wish you great success with your 4 year old. I encourage you to have more kids are a blessing. And next time I see your boss, I'll tell them what an amazing individual you are and I will never mention this again. Wife replies back, thank you, Jake. The true story.

[C]

And pretty crazy people have too much time on their hands. I think it's the moral there. Because if someone's looking up your tree line and going back in time, I mean like go out and touch some grass.

[B]

I like that at a certain point in a man's life, the wife takes neatly, just takes over the mom role. Like, that would be if a. If a child did something, you'd be like, I'm gonna what. What would your mom say if I told her? And then at a certain point in a man's life, you could just swap that neatly in with wife, and it works exactly the same.

[C]

Next up on the show after that lovely segue from Lon is a Jason clip talking about his origin story and how a guidance counselor really turned his life in an interesting direction.

[B]

Yeah, Jason told this story on Twist, and then he later told it live at south by Southwest with Bill Gurley. I saw this same story to a crowd. So, yes, here it is. A little taste of Jason's origin from. From April of this year.

[A]

Well, you know, I read about Brown and said, you know, they let you make your own degree. You can kind of roll your own concept. So my concept is psychology and, like, human behavior plus computers, because I'm into computers and online services specifically. You laughed at my face. This is when I was like 16 years old. And the guidance counselor, like, spit out his coffee laughing. He said, you're. You're barely going to get into any college. You have like a 72, three year average. Like, aren't you going to take the cop test? I said, yeah, I'm taking the cop test with my brother Josh and doesn't want to be a cop. I almost was one. And he said, you know, do that. Like it's better. Like, you're not barely getting into Brooklyn College. And I got into Brooklyn College and I woke up getting into Fordham. But just imagine, like a young person getting laughed in your face. And you know what that did to me? That was like, made me who I am. Yeah, that pissed me off so much. I was like, this guy made me be like, you know what? I'm going to show this guy. I'm going to get into a good school and I'm going to have a career.

[C]

I like that story.

[A]

It's a true story. True story. Wow, I got a crazy life. Keep going.

[B]

All right, one more. This is a quick little anecdote, but I thought it was fun, so I included it. Jason tells us the rules of private jet flag lying, including. Oh, yes, that you must never be late for the private jet. And here's why.

[A]

There's, like, two rules. There's three rules of private jets. No, there's four. I can tell you these. Number one, don't be late. I was like an hour late for a jet with Chamath. He still tells the story. It was his. It was my fault because I was like, I have a speaking gig and I'll go to Toronto with you to interview you for this other Shopify thing or whatever. But I'm leaving the shopping, this gig here. I gotta get all the way to San Jose. Like, don't worry about it. We're late. We go to. And it was like, I hit massive traffic. And we did have to divert from one airport to the other. Bummer. Second thing. Second thing, you don't take pictures or talk about it. That's what I'm saying. Third thing, you let the principal decide where they're going to sit first. So you come in, you place your bag somewhere neutral. You don't sit down, you wait for the principal to pick their seat, which is typically, if you go in, if there's like a four top in the front, like four seats, not no table, it would be the right one facing forward. That's where the principal sits, typically, in my experience. So you can sit to the left if you have a conversation with them, or crossroom if they don't want to spread their feet out, or caddy corner to them, or you set the table back there if they want to be. Have privacy. So you just say, hey, what do you want me to sit? You got a preference? You just say that.

[C]

Yeah, because they're paying for it.

[A]

Well, it's. Yes. It's like being in somebody's car, you know, like, or their house. Like, you don't just go into the master suite and you're like, I'll stay here. It's the biggest bet. And number four, you have to read the room. Is the principal, is the owner of the plane, like reading the newspaper or doing work and put their headphones on, or are they like, hey, how was your day? And they want to talk. So read the room. It's time to talk about one of my favorite companies in the world. Not just a sponsor, but a true friend of this podcast. Of course, I mean, the one, the only, Squarespace. Squarespace is the, the number one best way to start a website for your company. And that's going to help you stand out online, whether you're just getting started with your website or you're upgrading and scaling your existing business. Like, I'm constantly doing well. Squarespace is going to give you every tool you need, a great domain name, the ability to book meetings, sell content online, and it's going to be gorgeous because they have a new AI powered blueprint website builder you can use, or you can just use a template. It's up to you. And With a couple of simple prompts, with the blueprint tool, you can do design an entirely customizable website that perfectly suits your aesthetic, your voice, your personality. Support Twist's longest running sponsor by going to squarespace.com twist for a free trial. And when you're ready to Launch, go to squarespace.com twist for 10% off your first website or domain purchase. All right, this is all very. I like the last one. It's tactical and practical. Most people don't know how to behave.

[C]

Now everyone knows. You know, the next time you're on private jet thinking about where the principal.

[B]

Sits, clip that for your friends riding a private jet for the first time. So those, those are our three. Now it's time for everybody to pick their.

[A]

You guys pick. You guys pick.

[B]

I mean, I think the answer is Jason getting doxxed and responding in kind for sure. That's my pick.

[C]

The reason why I like that story, Lon, is because at the end of it, he says, we're going to put, you know, water under the bridge. I'm not going to blow up your life. I thought that was, that was quite good of him.

[A]

Of course, I don't blow up anybody's life.

[C]

But the best story is clearly the private story because that is, that is at once the most interesting and useless piece of information that has ever been given out on this show. Because the average listener is not going to get within a kilometer of a private jet.

[B]

Are you, kid? I took notes. I took diligent notes on that because I know one day it's going to come in hand.

[A]

Yeah, one day he'll be on my jet.

[C]

When Jason, when Jason does eventually get a jet, I'm going to be like, hey, we've been friends for so long.

[A]

I almost did. In 25, who knows what will happen in 26. We'll see.

[C]

Hope springs eternal.

[A]

No, I just, I could get it. I just keep pushing it off.

[B]

I'm going to, I'm going to monitor whether he's reading the paper or whether he seems like he wants to talk. Now I know, I know. For social, social cues.

[C]

When we're on the j. Cow plane, I'm going to be. I'm going to feed up on the couch. I'm going to take the good seat. I'm going to like, leave a mess in the kitchen.

[A]

Well, leave over and tell Marcus what? Well, yes, Marcus. Which one was his favorite story?

[B]

Marcus, which one is your. Of those three, which was your favorite? Marcus says doxing. Marcus is with me.

[A]

Okay. Doxing it is. He's a tiebreaker.

[B]

That's a classic. That's a classic. And it's very much like a J. Cal story. Like that's exactly how he handles those kinds of situations.

[A]

Yes. Hey dum dum, talk to your wife.

[B]

I like hey dum dum. That's good. Up next, I've got four nominees. This category was so packed. No, I had to go beyond three. The best guest of 2025. Huge category here, maybe the biggest of all. Our first nominee, this was from an an all star episode. We had Gilly Ranan on with this gentleman. But the nominee from Sequoia Capital, the legendary Doug Leone. Here he is on why he thinks venture capital is a scam.

[A]

First of all, the sham of the scam that is called venture capital. Let's take a look at this. We get paid. We, we raise money for which we get paid fees for the pleasure of investing the money. If we lose the money, so what? And if we make money, we get the key somewhere between 20 and 30%. You wonder why the balance between greed and fear always lean towards greed. A much more fair review would be here's the money, no fees and you have to match dollar for dollar what you raise with your own money. Now you would see the greed and fear balance. So already you have this, this proclivity to lean in because of the compensation structure. Point one, Point two. We have seen every generation. By the way, I know my partners or certainly in Sequoia Marketing won't be happy that I said all that, but who cares, you know, I'm old enough that I can say that. Great. He's right. Keep going.

[B]

Love what a guest says. They shouldn't say it, but they're old so they get. They're going to go for it.

[A]

That's. That to me is the best moment. Yeah, I shouldn't say this.

[B]

That's how you know it's going to be something good. Up next, from early in the year, we had on online expert in crypto Coffeezilla to discuss the. The meme coin explosion. I thought this was, this was one of my favorite episodes of the whole year. Just to get personal, here he is discussing whether or not crime is going to be legal in the future.

[A]

I also think there's an opportunity to demarcate out even if you're saying you. Like I said, by the way, I hate meme coins. I'm. I think if you want to do it, that's fine, but I just think it leads to these kinds of bad incentives. But that is different from fraud. Right. So when the President launched the coin, as much as I loathe it and I think it sets a bad precedent, whatever. They locked up their coins. Yes. They said they were going to do it, they locked it up.

[B]

Right.

[A]

Yeah. Whereas what we're talking about with Hayden Davis is fraud is when there's deception involved. Right. You said one thing and there's something else going on that the public doesn't know about that is materially harming them. That is like the sniping. That's a. That stuff should still be illegal and prosecuted heavily. What I want to see if it was my dream is that, look, even if they want to be like pro crypto innovation. Right, Meaning we want some rules of the road, that's fine. Still go after the fraud. Because fraud has never been legal, it never should be legal, but because some of these agencies are being gutted. Because I think there's this feeling of like, we want to, we want to throw out the guys who are, you know, who are clogging the wheels before you're going to get a lot less of that, unfortunately, which we need. We still need the fraud guys taking down the property. If you want XRP to do its thing and you want Ripple to be able to innovate, okay, whatever, you can make that case, but leave the fraud guys in place to still take down the bad guys. So there isn't a feeling at large that, oh, there's like, kind of like crimes legal for the next four years. Yeah, that is a valid concern.

[B]

Great coffee, Zilla. Hats off to him. Up next, one of our favorite founders of the moment on one of the fastest growing companies ever, Anton Osika of Lovable came by to talk about how he's predicting a coming wave of single founder startups. Let's take a look at that software.

[A]

And SaaS is just going to be absolutely disrupted. The amount of software, great software, much better software, is going to explode, but the prices are going to absolutely collapse. I think there is a case for people customizing, building almost their own software. But one of the pieces, even though the engineering time is kind of almost reduced to zero thanks to AI, there's a cost of building good software, which is to test it with a human. As humans, we were kind of the bottleneck for the software and that's typically what the product manager does. And now I think it's more like an AI builder that is really good at understanding and testing with users. So that's going to remain. And we're like Lovable. We're very bullish. On finding who are the best people building with our tools. So tomorrow we're launching something where we can easier, where we can launch your lovable apps and get feedback from users. And then I think what you're going to see is the single people companies are with great, where the founder has great product taste, building like single person SaaS companies and being able to launch and market them just thanks to the wisdom of the crowds figuring out where the best high value SaaS products are.

[C]

And that's launching tomorrow?

[A]

Yeah, that's launching tomorrow.

[C]

Well, very little news here on the show.

[B]

Jason, great guest. We've had him back, I believe, even since then. And then finally now, Jason, actually we have the clip predicted at the top that this was going to be the best episode of the year. Oh, double header of all star guests. We had Rahul Vora of Superhuman, now of course of Grammarly, which has taken on the name Superhuman, and Vlad Tenev of Robinhood. Here they both are together discussing their approaches to great design.

[A]

But Vlad, my question was going to be, I mean, you've had such a success, you've scaled your organization much further than Superhuman is right now. And we hope to be where you are at some point. How have you scaled the teaching of design? So I think we've heard things like don't design by committee, but the actual nuances of the craft and what makes Robinhood Robin Hood? How have you taught those pieces to people? This is such a good question. Yeah. Professional development. Yeah. I think it starts with great people, people that you trust being in leadership positions where they have influence. We've gone through this as we've grown the company and the design team where, you know, the first go around, we, we hired some professional managers that, you know, were kind of further from the work. But I think the balance we've reached is the people that are the best at the work, whose taste we trust the most, are, are in leadership positions. And then, you know, they're, they're kind of, they're kind of pushing things forward and you kind of supplement. I supplement that with being in meetings with them, being in jam sessions with them. And meetings are not just forums where we review the work, but we actually do design in meetings and actually change things.

[B]

There you go. Four amazing guest segments. What, what's your pleasure, guys? What did you think was the best?

[A]

Gosh, it's a tough one. Lovable. That was a great guest. I think Raul and Vlad is all time. So I think I'm gonna go Raul, Vlad, but what do you got?

[C]

Alex, you know, I'm gonna take Doug.

[A]

Doug was good. Yeah. Oh, God.

[C]

And the reason why is. Was like. Like, we're almost like reluctant knowledge because I feel like what Rahul and Vlad were talking about. Very interesting, but very much almost in their favor to say. Whereas I feel like Doug is kind of like walking and throwing hand grenades behind him, which makes him extra special to me.

[A]

Okay, what do you got, Lon? What do you got?

[B]

Yeah, I'm gonna. I'm gonna break the tie. I think Rahul and. And Vlad. One of my favorite episodes this year. I went back this week. I was re watching all these. I think that's obviously a standout episode, but I got to give it to Doug Leone, a legend.

[A]

I'm with you guys. Yeah, you meet. You guys both convinced me to change my vote.

[B]

And funny, like, it's one of the funny, funniest episodes of the year for sure. He's just got a great personality and a great way of speaking, and it's a delight to listen to him.

[A]

All right, I'm going to go with you guys. Doug Deglione, legend. Congratulations.

[B]

Up next, the best Jason Rant of 2025. Lots to choose from. Let me tell you. I had this list was 10 + at one point, and I had to winnow it down. First up, Jason got a little fired up after hearing about the r anti work subreddit and went off on his feelings about working from home. Let's take a look at this clip from April 30th of this year.

[A]

If you are a young person, I think, and you've been doing this for a while, and you're convinced, like, it's, you know, you're. It's some crazy capitalist, and they're forcing you to come to work. It's actually in your benefit, I think not socializing with people is making a generation of very weird people. I've been talking to some parents who have kids older than us who lost their entire college years or lost their high school years to the COVID lockdown.

[B]

Yeah.

[A]

So they literally lost graduation of college or graduation high school. You should demand as a young person to be in office and to be near the locus of power and to be mentored and to be professionally developed, you should be demanding that you're getting ripped off. Alex and I came up at a time, you know, me a little bit earlier, where we were in rooms with editors reading our work out loud, telling us we sucked, telling us how to be better. We got to watch other people do the job, and we had people model it first and the professional development that's happening on when we have our Monday editorial meeting for Founder university, which I've been at two or three of them. I mean, the learning and the feedback I'm getting back from people is like, whoa. That is like the best part of the job. One of the core challenges facing every single early stage company is getting your first 100 customers. And I say this all the time here on this week in startups, to get there, sometimes you have to do creative things, even things that don't scale. So what does that actually mean? And what are some tried and true techniques that have worked for founders in the past? And which one of those can you tap for inspiration? To find out, you could join an accelerator or you could just check out this free resource online at HubSpot called how to get your first 100 customers. This isn't just some little pamphlet with generic ideas. No, it's a full framework. And that framework is filled with practical tips and real world case studies from amazing founders and experts, including my pal Sam Parr and Sean Purry, you know, the hosts of my first Million, which is a great podcast. I listen to every single episode. They're just awesome. So download the guide for [e-mail] twist1 or just find a link in the description of this show. And thanks to our friends at HubSpot for sponsoring today's episode.

[B]

All right, next rant. This is from May. This is aimed. It was aimed at the time at AMC theaters and their management, but I think it just speaks generally to the, the theatrical exhibition industry. Here's Jason's thoughts on how to fix movie theaters.

[A]

They made skiing into a drug for a certain cohort of people. Where you just get that high, you want to keep doing it. Movies have done the opposite. Movies have said, every time you want to come here, we're going to make it more painful for you. You want to buy a ticket and you bring your family of five. Great. You know, it's 10 bucks a ticket on average, 50 bucks. And you want to buy stuff at the concession stand, it's going to be 10 bucks per person, minimum. Probably more like 15. So family of five, you know, if mom and dad sit it out and kids get $15 each, now you're at 95 bucks. 95 bucks for two hours of entertainment. That's not cheap, right? And so people, and then maybe you got the epic. Maybe you go skiing for the entire day for free. People are making these trade offs in their mind. Then they were like, oh yeah, we need more money. So how do we get more money? We're gonna add $2 to everything for three day. I'm gonna make you watch a movie in three day that you didn't never ask for. Three day. Oh, I'm gonna put on IMAX. We charge another three bucks. So now you're getting to 16 bucks. Oh, yeah. I'm gonna make it a luxury theater. You're gonna be able to order food to your seat. Now the 10 bucks in popcorn and drinks went to 25 bucks in chicken fingers. Etc. I literally spent 250 when I go to the movies now let that sink in. Five people, 250 bucks. About 50 bucks a person. I go to an IMAX. I like the IMAX there. That's 18 bucks a ticket. And everybody orders dessert. And so it's basically combining dinner anyway. If they just went with an all you can eat model of 20 bucks per person, and then maybe if it's a family of five, you discount a little bit. You get to $50 per month for a family of five. We would go to the movies two or three times a week. They could do, I believe, what the ski industry did, which is make people addicted again to the experience of going out and seeing movies. Love it. Great, great rant, Jake. I give myself a pat on the back for that one.

[B]

That one definitely holds up.

[A]

Holds up for sure.

[B]

This one from late July was aimed at the Tea app. You'll recall this was an app that was briefly available in the App Store that let women discuss problematic men in their lives privately without men having access. It got pulled from the App Store. It got hacked. There was all sorts of controversy around it. Here were Jason's thoughts on the T app.

[A]

They didn't encrypt the driver's licenses, pictures and reviews of former dates or boyfriends that women were leaving in this app. So this is incredibly damaging on, like, multiple vectors. Number one, a person's driver's license and their photo being released in a hack opens them up to subsequent hacks.

[B]

Yep.

[A]

And if that person had posted about somebody they dated who they felt was dangerous, let's say in the worst circumstance.

[C]

Yep.

[A]

If that's true and that person was dangerous, well, then you've just let a dangerous person know that you wrote a review of them that you thought was anonymous.

[C]

Other than that, great application though, right? Fantastic.

[A]

Brutal.

[B]

Yeah, it's one of those things that grew from, like, women used to have, like, spreadsheets that they would share like this or like in person networks. And I feel like those Kind of whisper networks make sense, but the moment you put it on an app that's in the App Store, there's. There's a lot of problems that are going to develop. Last one on our Jason Rand lineup, I'll just say the title. You can't trust Zuck. Let's take a look at.

[C]

I remember this one.

[A]

Oh, boy. It's every year I do this one. But then the weakness to that is empathy and humanity and at the cost of some, like, logical discussion. And then he put people around him who cannot make or do not have the ability to tell him when he's doing something that is absolutely abhorrent, stupid, and long term bad for society. And this is why I like to. I've said since the beginning, you can't trust Zuckerberg. Zuck can't trust Zuck. Zuck should understand he's made the wrong decision about Instagram. Kids on Instagram, you know, banning Trump from the platform. You know, every decision he could make, he makes the wrong decision on these social issues. Therefore, he needs an ombudsman. He needs a group of people on that board or around him. That's not Mark Andreessen. We're not Peter Thiel.

[C]

I was about to say. He's got Mark right there.

[A]

No, these people are going, you know, the people who you made money with. That's like putting me, you know, on Travis's board or on Robin Hood's board. Like, those are my guys. I believe in them. I'm going to be like, yeah. Now I'm a little bit unique in that. I would tell them when they're up, but whatever's happened at Meta has metastasized to the point where Zuckerberg does not have anybody around him telling them when they're doing stupid. This is a dangerous place for somebody with that much power to have. Oh, yeah, that's pretty clear. It's got to be Zuck, right? Because I was so fired up.

[C]

Well, no, you're, you're, you win on that one because you said Meta and then Metastasize, which I believe is a really good play on. Yeah, that I didn't catch the first time.

[A]

I didn't catch it either. It wasn't intentional. What do you think, Lon? You favor the movie one?

[B]

No, no, I think it's unanimous. The moment I picked this one out and clipped it, I was like, oh, it's absolutely going to be the Zuckerberg. And it's such a twist clap. I mean, it goes back to the very first season of Twist. You were already. Remember, you looked right into the camera and you were telling people about not trust Facebook and Facebook apps. That was like, yes. Six months into the show. So it's a classic.

[A]

Yeah. Fifteen years ago, I was like, listen, he's gonna steal your ideas.

[B]

Yeah.

[A]

Okay, let's keep moving.

[B]

Let's keep rolling. All right, my favorite category is. Up next, the most controversial moments of 2025.

[A]

Okay.

[B]

These are times when the show got a little spicy, sometimes the podcast. So up next, we've got from my first episode back on the show February 10th. We were discussing super bowl ads. That's why I've got the super bowl image behind me. And we're talking about Jason and his rejection of dangerous rich guy hobbies. Let's take a look.

[A]

Yes.

[B]

John Denver was for everybody.

[A]

So John Denver was for everybody. And as I always warn my friends who want to become pilots, if you got a great life and you're rich and you're famous or any combination of those things, love, you've got a family, you don't need to be an experimental pilot. It's like right in the name, like test pilot. You don't need to do that. If you're rich, you're powerful, you're famous, you could have a test pilot. You could let other people be the test pilots. I'm of course referring to the fact that people don't know John Denver died young flying, like some experimental plane.

[B]

Listen, some guys just have a need for speed, Jason.

[A]

No, it's just how it's so dumb.

[C]

Cave diving, experimental flying and motor driving. None of that. Don't do them.

[B]

Also experimental subs. Please let James Cameron do the submarine tech. He's. He's the expert.

[A]

That's another one down there. Billionaire and his son decide they're going to go on an experimental submarine. If it has experimental or test in the word if.

[B]

If it's being operated with a PlayStation controller, you don't need to be on that. Hard to argue. Hard to argue with. I think those point. Unless you're Tom Cruise, it's hard to argue with all of those points.

[C]

RIP John Denver, what's next?

[B]

Up next, in April, you'll recall a group of celebrities went on a blue origin flight into orbit. The group included Katy Perry. So we all had some thoughts about Katy Perry's flight and return from orbit. Here's. Here's that clip.

[A]

She looks terrified.

[B]

Yeah. And then when they were walking onto the space shuttle, she's having second thoughts.

[A]

And then the moment they got Katy Perry vomiting.

[B]

No, the Moment they got back. This is right when the spacecraft landed. Katy Perry kissed the ground. Yes.

[A]

Once again, Katy Perry making herself the center of attention.

[B]

Of course. Oh, even more. Gail let us know that as they were attempting re entry, Katy Perry treated them all to a little song.

[A]

The best part was when we got back in our seats after zero GS, Katy sang what a Wonderful World. She did that. Oh, my God. I see trees. Oh, yes, yes, yes.

[B]

Because you're in a spacecraft, you can't get away. It's a command performance. You can't escape.

[A]

Wow. I can't think of anything worse.

[B]

Just let us enjoy the moment.

[A]

Get out to space. You're.

[B]

We're looking at Earth, the majesty of the cosmos all around you. And Katy Perry's got to be like, hang on, I need to make this moment better.

[A]

I mean, wow. I just want to shout out Orlando Bloom. Now. We all know what this poor man.

[B]

Has to go through.

[A]

There's a lot going on here. I'll just leave it at that. Because that rocket kind of feel like the design of the rocket is a little bit trolling.

[B]

Oh, it couldn't look more wang? Like, there's nothing you could do to make it look more like a wang?

[A]

No. It is literally designed to evoke a certain. Yes.

[B]

Phallic image. Yes.

[A]

I mean, rockets inherently look like penises. And then this one is designed to just look like a circumcised penis. Oh, God. Very graphic.

[B]

No lie in that entire clip. Oh, God.

[C]

I'm having more fun than I expected.

[A]

All right, what's next?

[B]

All right, up next, from August, Jason responded. Kara Swisher, former, former friend, former confidant. When I guess the host of the Pivot podcast now, she went on the Bulwark podcast, and they were discussing her. Her on again, off again friendship with Jason, and then Jason responded on Twist. So here. Here is that clip.

[A]

I just feel like he had. He just has made a trade that I don't love. And I wish you would call me because I'm like, it's fine to argue, Jason. Maybe I'll call her right now on air. Should I call Kara Swisher on air right now? Just have her go on air. I'll just call her on air. What people don't know is all in makes much, much, much, much, much more money than Pivot does, and it's higher in the rankings than Pivot every weekend. So I think a little of this might be reverse jealousy that that show is so popular, but it makes a magnitude more money than Pivot like multiples already. And Pivot's been around forever and this is like a four year old podcast. So it's really not about money. And then in terms of money, like, yeah, what I learned about money is after $10 million, it doesn't matter. And I have much more. So I.

[C]

That's in joke.

[B]

That's interesting.

[A]

I don't care about money. I've never cared about money. And maybe, maybe that's a problem for people, that I'm not motivated. If I was motivated by money, I would be sucking up to Zuckerberg. I think I do a pretty good job calling balls and strikes. I just, I'm very pragmatic here and honest with Tim on his podcast. People on the left were over the moon giving money to the Democratic Party to get all kinds of concessions around DEI and all kinds of concessions around regulation for AI. And now there's a ton of the same people, same people who flip to Trump because it's good for their business. This is what business people do. You just mentioned in the last one. What do capitalists do? They manipulate politicians. They back them with money to get the result they want. This has nothing to do with Jason Calicatis. It has to do with how the.

[C]

World has always worked after $10 million. Guys, it doesn't. It doesn't matter.

[B]

It doesn't. What? You got that much? Take it from between.

[C]

Between that and the private jet stuff, I really think that I'm learning a lot today. I'm growing as a man.

[B]

All right, last one. This is from Halloween, October 31st of this year. This is actually, I believe, among our most viral clips of the year. We cut this one into a short. It's got hundreds of comments, tens of hundreds of thousands of views. I would never work with Sam Altman. And OpenAI would be the title. Let's take a look.

[A]

If I was a developer of any kind, I would never work with Sam Altman and OpenAI. Let me say that this is a warning. People can clip this. This is a warning for anybody dumb enough to use Sam Altman's OpenAI API. They are studying. You remember, Sam Altman's been around the block. I've known him since Loop. He's an incredibly savvy person and he wants every bit of revenue from the ecosystem. He is taking no prisoners. He's going to study how you're using the API, which he has the right to do. Sam Altman comes from the Zuckerberg school of business, which is give dumb people access to your tools, study them, and like the Borg steal every innovation they have. And Zuckerberg got it from Bill Gates and Microsoft. Microsoft had a platform and operating system. They let people build Lotus 1, 2, 3, then they did Microsoft Excel. They let people build a product called WordPerfect and WordStar, and then they built Microsoft Word. Now, wait, what category are we in again?

[B]

Most controversial moments.

[A]

Most controversial moments.

[C]

And people, I think were a little surprised, Jason, that you were so critical, I think, of companies using commercially available AI models via popular API hooks. I mean, like a lot of companies are doing this.

[A]

I think I'm right. I think if you use the commercially available models and you're not containing the learning, they could benefit from it. And I honestly don't believe that they're not figuring out ways to backdoor your data into their models. So I think maybe for me, that was the most controversial moment, saying, don't trust the large language models. But what do you think, Juan?

[B]

That was definitely the one the public found most controversial. To me personally, I gotta go with Katy Perry in space. I thought we covered a whole lot of ground in that clip. I think all of it was pretty.

[A]

Spicy, pretty personal with.

[C]

Yeah, I think Jason went too far on the Orlando Bloom comment. Also, he's out of date. That was out of line. She's dating Justin Trudeau. But also critically, in that segment, we got Lon to say Wang like, which I think was an all time surprise. In terms of.

[A]

What do you got? What do you got for most controversial?

[C]

I mean, it's got to be the Katy Perry thing.

[A]

Katy Perry wins. There it is. Congrats to Katy Perry.

[B]

I mean, I can't think of anything worse than being trapped with Katy Perry on a space flight. That's a controversial statement. That's a big.

[A]

I would say in an elevator, I would be pretty. I would be counting the floors.

[B]

Two more categories left. We're almost out of here.

[A]

Almost out of here for the twisties. We're getting there. We're getting.

[B]

We're getting there.

[A]

We're.

[B]

We're at the home. This is like the fourth hour of the Oscars where they start making jokes about how long it's been. So up next, we've got a first ever award this year, the disgraciad of the year. Jason gave out. He gave out a whole lot of these. Notebook LM pulled up many, many examples, but I've winnowed it down to the top four. Up first, Apple and Tim Cook got a big descrizion. This is in episode 2162 back in.

[A]

August let's take a look and listen. I mean say what you will, if we're sitting here a year from now and actually Apple's making products here, that's what Steve Jobs actually wanted to do. He wanted to make these products here. And you and I were having a private discussion about Apple. I think we'll start here. Just how disgrace this company.

[B]

It's disappointing. That's how I feel. I feel disappointed. I. When we got the iPad, when we got the iPhone, you were looking forward to a lifetime of exciting Apple products. You were going to, every five years there was going to be some new amazing innovation and it has not been realized that vision.

[A]

And you and I were in Santa Monica doing mahalo and we would go to the Apple Store which had just recently opened. We were there for the iPhone launches.

[B]

We painted in line overnight.

[A]

Yeah, yeah. And it was like some of the greatest moments in technology history was that showmanship and that commitment to releasing new groundbreaking technology. And I think once we got through the pipeline of whatever Steve Jobs had thought of, there was no, nothing bold left. And I said on cnbc, I think there's a case for Tim Cook, you know, leaving. I didn't say get fired. I don't think think I might have said that.

[B]

And it was like descrat to Apple. Up next, this is another clip from early, early in the year January 6th. Jason taking aim at the Vail ski resort. Let's take a look.

[A]

Which is Vail Resorts, the company, the stock ticker.

[C]

O MTN.

[A]

I looked it up before MTN and let's see, five years. I'm looking at the five year stock.

[C]

It's down.

[A]

You bought the stock in 2021 for $272. You've lost half your money. You've lost half your money. So this organization, their stock price tells you that they're mismanaged and not run well, I think yes, and they probably should. There should be some stock shareholder lawsuits here just based on the just utter incompetence of this. There should be a no vote. And listen, I, I have an epic pass for I don't know, six, seven years and I love it. But this is a terrible organization. It's a disgrace. Descriptiad, as we say in Brooklyn, descartes.

[B]

Com.

[A]

I own the domain descritiad and I am going to redirect it.

[C]

I already know how to spell that word. But you should redirect it to Vail's IR page.

[B]

It's D I S G R a Z I a D as I've Learned this year.

[A]

That's how you spell disgraziadial.com. and now it's infected all in.

[B]

And now, yeah, it's gone. It's everywhere.

[A]

Timothy Chalamet will be doing disgraciad soon.

[C]

Next to Phil Hellmuth on the poker table. Sorry, Lon.

[B]

Go for it. Up next, here's a clip from June. The only politician to make the disgraciad list, LA Mayor Karen Bass. Here's what Jason had to say for.

[A]

People who just landowners. I heard you mention they were going after ranch owners, etcetera, who have to deal with fires, too. And by the way, I was spending time with Rick Caruso, who ran for mayor, lost to Karen Bass in la. Karen Bass, complete incompetence to scratch like the worst leader you could ever have during a crisis. As we saw her, like, freeze up when they were just asking her questions about what you're going to do when she was on some boondoggle out of the country while the city burned. And I hope he runs again and I hope they put him in there.

[B]

But the African nation of Ghana, that's where she was while LA was burning. Finally, from October 1st, an app has made the actual Descartes. It's bank of America's mobile interface. Let's take a look at this clip.

[C]

There's some poor team who has to relive their trauma. All right, here we go.

[A]

There's just a generational shift. Most people don't want to use these old banks, they want to use the new banks. Most people don't want to use the last paradigm, they want to use the new paradigm. The interfaces on these are incredible. You know, if you open up your bank of America, it's just disgraciad when compared to using Venmo or using Robinhood. It's so crazy to me that these big companies can't just hire elite designers to refresh their app. If you were working at bank of America or any of these major banks, literally just go find a design firm to tell you what to do and just spend a million dollars having three different design firms make you three different versions each. Now you get nine versions and just have the CEO or the president, whoever's got tastes, say this one.

[C]

Yeah. Is all mobile banks, I think would be up for that. Descartes. Yeah. But I'm glad we singled out one of them.

[A]

Who's yours, Alex? Who's your disgrace?

[C]

I'm going to go with your gut.

[B]

Yeah.

[C]

I'm going to go with Apple. Not because it was the best, like like, angry riff on why they're bad, but just because I really fundamentally agree with it. Like, I really think that Apple is. Is a company whose products I use but I find interchangeable today, and that loss of magic is a crisis.

[B]

Vaughn. Yeah, I totally agree. If we're going on who deserves the descrit of the year the most, I think you've got to go with Apple. The AI disappointments aside, just where are the great compelling Apple products of this generation? AirBuds are the only ones I could think of. AirPods, not Airbus.

[C]

You want to do you want to weigh in?

[A]

I got to go. Apple. I think it's the most logical of all the descriades. It is disgraceful that they can't come up with something super compelling other than this, like, tiny, thin phone, which, like, if that's the big innovation, it's thinner, it's nice. I think it's, like, beautiful. But honestly, like, after buying it, I would never buy it again. I'm going back to the other one the second I get a chance because the camera sucks so bad.

[B]

But even that, it's not an original idea. They already did the. The air. Like, we already got the thin laptop and the thin iPad. They're just. They're just doing that again for the phone.

[C]

Yep. Should have made a cheaper Vision Pro to begin with. Y' all got some market share.

[B]

I also don't really. I don't want a thinner phone in my pocket. I feel like that wouldn't feel right. It's at the right level of bulkiness, I think right now.

[C]

Make it twice as big and give me three times the battery life and I'll buy four.

[B]

Yeah, I just. I don't. That's never been a thought where I'm like, gee, I wish my phone was lighter. Like, I've never had that thought once in my life.

[A]

I mean, you. It's. It feels nice in your hand. That's all. I'll say. It does feel nice in your hand.

[B]

Well, there you go. That's something that counts. All right, our final category. I saved a fun one for last. These are the best Alex dad jokes of 2025. Again, so many to choose from. A lot. A bevy of options. And we actually have two nominees from the same episode. Episode 2174 from September 5th. Here's the first one where Alex says he's got a pass to call Jason the C word, but he doesn't have that C word. Let's take a look.

[A]

Well, it was just like, you know, before we got on the show. And you were using the C word over and over again. And I was like, you can't call me the C word, Alex. You're like, I'm zooming in from England. I'm in England right now. I have the UK pass.

[C]

I'm Australian. I'm allowed to say that Jason is capacious. You're correct.

[A]

Yes. You did say capacious multiple times. I took it the right way. I took it in the spirit it was intended.

[C]

We have fun here at Twist, ladies and gentlemen.

[B]

We have fun from the same episode here. Here's another Alex dad joke for the same episode. The same episode, back to back. Dad.

[C]

This is around the time my second child turned one, so I must have.

[A]

Really been on one.

[C]

All right, here we go.

[A]

These dad jokes. Here we go. To find stuff. So that's why I knew a guy.

[C]

Who wanted to be a studio head and had some money. I mean, like, it's almost like if that person had money and time, they could.

[A]

I mean, making raunchy stoner comedies seems like a genre that, you know, you could do some real damage.

[C]

That's like my personality after 8pm so I'm totally here for it.

[A]

That was a dad joke from Alex. I heard crickets. I heard that. No, don't apologize. We love it. I don't even mean to.

[C]

Anyways, keep going.

[A]

There it is.

[C]

Falling. Falling right into them.

[B]

This is a very recent one from December 15th. Only last week we got. We snuck it in under the. Under the wire. This is Alex on Lightspeed Ventures and their latest fund. Let's take a look.

[C]

Oh, yeah, right.

[A]

All right, here we go.

[C]

Very impressive fund. I did not know they were all of those names, but now I can see why they managed to put together 9 billion. Shout out to everyone at Lightspeed, please take everyone out to lunch because you have enough cash for that?

[A]

Yeah, absolutely. And that is that. That immediately goes into the Alex's Best Dad Jokes of the Year.

[C]

Thank you. Well, I'm running out of time. I mean, I gotta squeeze them in, man.

[A]

Makes them easier to find when I tag them, right, Lon? I tag them like that. Makes them easier to find them.

[B]

They come right up in notebook when you put dad. But I. I will say this category, I did a pretty exhaustive search. Like, I. I looked even. Even for ones that didn't come up in the Notebook. LM deep dive.

[A]

Hard to find them. Hard to find.

[C]

You know, I wanted. For Christmas, I wanted to force Lon to endure my crappy humor for hours on end. So I got it got it.

[B]

We had the whole team. We. We broke it up into fiscal quarters, but we had the whole team rewatch almost every episode. We were. I did Q1, we had Jacob doing Q2, Marcus doing Q3. We really, we really exhaustively searched.

[A]

Great.

[B]

We didn't want to leave anything out. So finally, from April 16, not so much a dad joke. We all, the entire team, just really like the way Alex said yes, sir in this clip.

[C]

This is just hazy.

[B]

A quick look from April 16.

[A]

I am so excited today because I know that Alex's grin can mean only one thing. Somebody filed to go public. Who was it?

[C]

Yes, sir, it's Figma.

[B]

Yes, sir.

[A]

Yes, sir, it's Figma.

[C]

That was my honest feeling. I was so excited.

[A]

What do you got, Lon? You're.

[B]

You're.

[A]

You're such a student of the comedic arts.

[B]

I mean, we, we all. I have been saying yes, sir like that all week. So I think that. I think that has my.

[A]

Yes, sir. I think that's my twisty.

[C]

No, I. The correct one was capacious, clearly. What a. What a good year, guys. We did like 150some episodes. We covered so much fricking ground. The world changed so much, and we even mostly got along.

[B]

Yeah, absolutely. Mostly.

[A]

Got a lot of. Mostly. There's your dad joke early for next year.

[B]

I got, I got one more clip there. We'll. We'll exit on.

[C]

All right.

[B]

We put some random memorable moments that didn't necessarily fit into any category. So I've got, I've got one here. We were going to do a whole category of Jason's Trump impressions. It felt a little overkill to me, but I've saved this one from episode 2109 on April 9th. Here was, I think, the best Jason Trump impression expression of 2025 that we.

[A]

Have this expression here in Texas as the crow flies. Yeah. I don't know if you've heard this.

[C]

It's also in Tennessee. I think it's in Tennessee.

[B]

Groceries. That old fashioned term. Groceries.

[A]

But as the. It's a word. Groceries. Okay. It's just a word. I love that. It's like one of my favorite trump clips of all time. I don't know. It's a simple word.

[B]

Simple old fashioned word. Groceries. Groceries made me chuckle. So I wanted to.

[C]

How many Trump impressions were there to choose from? Because I feel like it happens like once a month at least.

[A]

We.

[B]

We had four or five in. In the, in the category. And I just thought, you know what? That's a lot. That's a lot of Trump impressions. I don't know if we need to make it a whole thing, but I wanted to show that clip at least.

[C]

No, I'm happy for us. Happy, happy end of the year, guys. Happy New Year to everyone listening. We're back next year and we'll see.

[A]

You in the new year on Twist. Bye.

[B]

Bye.