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

30 Dec 2025 · 56 min · 31 chapters

Ask about this episode

Ask anything about it. ChatGPT or Claude reads this page and answers with the times it was said.

Connect VO and ask about every podcast you hear, including the moments you saved. Add to ChatGPT · Add to Claude

In short

This Week in Startups: Episode E2229 - THE 2025 TWISTY AWARDS!

Podcast Overview Host: Jason Calacanis Description: This Week in Startups covers startups, tech, markets, media, and hot topics in business and technology, featuring interviews with top founders, operators, investors, and innovators.

---

Episode Summary In this final episode of the year, Jason Calacanis hosts the annual TWISTY Awards, reflecting on the standout moments from the podcast throughout 2025. The episode features clips from various guests, memorable anecdotes, significant trends, and key discussions from the year.

Key Highlights

  • Introduction to the TWISTY Awards and wrap-up of 2025.
  • Nominees and winners across various categories, including Best Name Drop, Biggest Trends, and more.

---

Categories and Discussions

  1. Best Name Drop
  2. Nominees:
  3. Jason's experiences at XAI with Elon Musk.
  4. Courtside seats with Ben Stiller and Timothée Chalamet at a Knicks game.
  5. High-profile gathering at F1 races.
  • Winner: Courtside seats anecdote, featuring a humorous dig at Detroit's ticket prices.
  1. Biggest Trends of 2025
  2. Trends Discussed:
  3. The return of M&A and regulatory changes under Lena Khan.
  4. AI job displacement and potential youth unemployment crises.
  5. Humanoid robots emerging as possibly the greatest products of humanity.
  • Most Important Trend: AI job displacement due to automation, with a focus on the implications for young job seekers.
  1. Best Jason Anecdote
  2. Memorable Stories:
  3. Jason's response to being doxxed, highlighting security measures taken.
  4. His guidance counselor's rejection of his college aspirations.
  5. Rules of flying on private jets, providing practical advice.
  • Winner: The doxxing incident as it combines humor with a serious undertone.
  1. Best Guest
  2. Nominees:
  3. Doug Leone (Sequoia Capital) discussing the venture capital model.
  4. Coffeezilla analyzing meme coins and fraud.
  5. Anton Osika (Lovable) predicting trends in single-founders startups.
  6. Rahul Vora (Superhuman) and Vlad Tenev (Robinhood) discussing design principles.
  • Winner: Doug Leone for his candid and humorous take on venture capital.
  1. Best Jason Rant
  2. Rants Included:
  3. Critique of the anti-work subreddit.
  4. Movie theater pricing and proposed changes for better experiences.
  5. Criticism of Sam Altman and OpenAI for data practices.
  • Winner: Critique of Zuckerberg and Meta for poor decision-making.
  1. Disgraciad of the Year
  2. Nominees:
  3. Apple and Tim Cook for lack of innovation.
  4. Vail Resorts for poor management.
  5. LA Mayor Karen Bass for incompetence during crises.
  6. Bank of America's app interface.
  • Winner: Apple for failing to deliver groundbreaking products.
  1. Best Alex Dad Jokes
  2. Featured Jokes:
  3. Playful remarks about using the “C-word” and clever wordplay.
  4. Humor regarding the ability to produce raunchy comedies due to Alex's personality.
  • Winner: "Yes, sir!" for its enthusiastic delivery.

---

Conclusion The episode wraps up with reflections on the year's achievements, humor, and the camaraderie between Jason and his co-hosts, Lon and Alex. They also express gratitude towards listeners and partners, setting the stage for another exciting year ahead.

Subscribe: [This Week in Startups on Apple](https://rb.gy/v19fcp)

---

Additional Links

  • [LinkedIn Ads](http://linkedin.com/thisweekinstartups)
  • [Squarespace](https://squarespace.com/twist)
  • [HubSpot](http://clickhubspot.com/twist1)

Follow the Hosts:

  • Jason Calacanis: [X](https://twitter.com/Jason) | [LinkedIn](https://www.linkedin.com/in/jasoncalacanis/)
  • Alex Wilhelm: [X](https://x.com/alex) | [LinkedIn](https://www.linkedin.com/in/alexwilhelm/)
  • Lon Harris: [X](https://x.com/lons)

---

*Note: This episode serves as a humorous and insightful retrospective on the year, filled with engaging discussions and entertaining anecdotes from the world of startups.*

Written by AI. May contain mistakes. Listen to the episode to check what was said.

Chapters

Tap a time to open that second in VO

Predictions for 2025 Products

0:45 to 1:01

Discussion on predictions about job creation and the impact of Optimus.

“This was one of my favorite episodes of the whole year just to get personal.”

The Best Jason Name Drops

1:01 to 1:42

Hosts begin discussing the nominees for the best name drops of the year.

“Download it for free at clickhubspot.com slash twist1.”

Name Dropping Highlights

2:35 to 3:44

Discussion on the nominees and highlights from Jason's past name drops.

“The first clip, this is Jason discussing his experiences hanging out at the XAI offices.”

Memorable Anecdotes from F1

3:44 to 5:35

Jason shares experiences from an F1 event with notable personalities.

“hanging out at F1 with some notable, notable notables.”

Trends of 2025: M&A and Job Displacement

5:35 to 7:45

Exploration of major trends, including M&A and AI job displacement.

“He's got, you know, he was on the sphere today.”

Predictions on Humanoid Robots

8:01 to 10:10

Discussion on the potential impact and success of humanoid robots.

“When I graduated, there weren't a lot of jobs in 94, 92, 93.”

2025 Trends Recap

10:10 to 13:18

Recap and discussion on the biggest trends for 2025, including M&A.

“You're going to target your ads based on job title, based on industry, based on skills.”

Best Jason Anecdotes of 2025

13:18 to 14:01

Recap of Jason's best anecdotes and stories from the year.

“M &A returns, Lena Khan is gone, AI job displacement, the rise of the humanoid robot.”

Jason's Doxxing Incident

14:01 to 17:01

Learn about Jason's personal experience with doxxing and how he handled it.

“End of Lena Khan and I'll stop talking about it.”

Jason's Origin Story

17:02 to 18:23

Discover Jason's journey and how a guidance counselor's doubt fueled his success.

“the wife neatly just takes over the mom role.”
Show all 31 chapters

Private Jet Etiquette

18:24 to 19:51

Understand the important rules of etiquette when flying on private jets.

“This is a quick little anecdote, but I thought it was fun.”

Recap of Jason's Stories

20:41 to 21:49

Hear the team's favorites among Jason's anecdotes and their insights.

“You know, the next time you're on private jet, thinking about where the principal sits.”

Best Guests of 2025 Nominees

21:50 to 23:11

Explore the nominees for the best guests of 2025 and their impactful statements.

“I'm going to monitor whether he's reading the paper or whether he seems like he wants to talk now.”

Doug Leone on Venture Capital

23:12 to 24:48

Delve into Doug Leone's candid views on the venture capital industry.

“You wonder why the balance between greed and fear always lean towards greed.”

Coffeezilla on Crypto Fraud

24:49 to 26:21

Listen to Coffeezilla discuss the implications of fraud in the crypto space.

“like, we want to throw out the guys who are clogging the wheels before.”

Rahul Vora and Vlad Tenev on Design

26:22 to 27:58

Gain insights from Rahul Vora and Vlad Tenev about the importance of design.

“Well, break a little news here on the show, Jason.”

Best Guest of 2025: Raul, Vlad, and Doug

28:01 to 29:04

The hosts discuss their favorite guests from the past year, debating between several standout episodes.

“And the reason why is it was like, like we're almost like a reluctant knowledge because I feel like what Raul and Vlad were talking about, very interesting, but very much almost in their favor to say.”

Jason's Rant Highlights: Working from Home

29:05 to 30:38

Jason shares his passionate views on the importance of in-person work and its benefits for young professionals.

“Let me tell you, I had, this list was 10 plus at one point and I had to winnow it down.”

Jason's Rant on Movie Theaters

31:17 to 32:50

Jason critiques the pricing strategy of the movie theater industry and suggests a new model to attract customers.

“This is aimed, it was aimed at the time at AMC theaters and their management, but I think it just speaks generally to the theatrical exhibition industry.”

Critique of the T App

32:51 to 33:50

Discussion on the controversy surrounding the T app and its implications for user privacy and safety.

“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.”

Zuckerberg's Decisions Under Fire

33:51 to 35:56

Jason expresses his disdain for Mark Zuckerberg's leadership and decision-making processes at Meta.

“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.”

Controversial Celebrity Moments from 2025

35:57 to 37:46

The hosts discuss various controversial moments involving celebrities over the past year, including Katy Perry.

“You were already, remember you looked right into the camera and you were telling people about not to trust Facebook and Facebook.”

Jason's Response to Kara Swisher

37:47 to 41:24

Jason responds to comments made by Kara Swisher regarding their professional relationship and podcast success.

“a group of celebrities went on a Blue Origin flight into orbit.”

Criticism of OpenAI and Sam Altman

41:25 to 42:00

Jason warns against working with Sam Altman and OpenAI, highlighting potential risks for developers.

“This is from Halloween, October 31st of this year.”

Sam Altman's Revenue Strategy

42:00 to 43:16

Explore how Sam Altman analyzes API usage to maximize revenue.

“Remember, Sam Altman's been around the block.”

Controversial Moments in AI

43:16 to 44:15

Discussion on public reactions to AI models and trust issues.

“That was definitely the one the public found most controversial.”

Disgraciad of the Year Award

44:15 to 46:12

Jason presents the Disgraciad of the Year award to various nominees.

“got a first ever award this year, the Disgraciad of the Year.”

Critique of Apple's Innovations

46:12 to 48:16

Analyzing Apple's recent product releases and criticisms.

“So this organization, their stock price tells you that they're mismanaged and not run well, I think.”

Bank of America's Disgraciad

48:16 to 49:49

Discussion on the issues with Bank of America's mobile app.

“Like I really think that Apple is a company whose products I use, but I find interchangeable today.”

Best Dad Jokes of 2025

49:49 to 51:18

Reviewing funny dad jokes from the podcast throughout the year.

“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.”

Memorable Moments and Trump Impressions

51:18 to 55:39

Highlighting random memorable moments and Trump impressions from the year.

“Yes, you did say capacious multiple times.”
Hear the part that matters, and keep it.Open this episode in VO. Double tap your headphones to save a moment as you listen.
Get VO free

Transcript

Automatic transcript. May contain errors.

0:00It'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 discussion. Everybody agrees on that. 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. A bold prediction. I said, so you're married. I said, I'll tell you what.

0:34We'll talk to your wife. I'll tell you 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's seat. That is at 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. 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 slash twist1.

1:09Squarespace, turn your idea into a beautiful website. Go to squarespace.com slash 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 slash thisweekinstartups to claim your credit. All right, everybody. Welcome back to our year-end episode. It's the Twisties. Twisties 2025. These are the best of awards. Lon is here. Lon Harris, our editorial director.

1:53And, of course, my co-host, Alex Willem. Hey, hey, hey, hey, hey. Let's get started. 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. It's hilarious. By the way, I don't know the categories or the nominees. I'm coming in completely cold, so this is a new category. But okay, here we go. Best name drop. I can imagine Timothee Chalamet, Elon Musk, Trump. I mean, there's so many possible.

2:34You've left a few names off, but 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. I didn't realize you'd gone WWE and less nerdy. So yeah, at XAI on Saturdays, we push code. We get the new models out, GROC 3.5, and then we lift. We lift. But I met a bunch of great team members over at XAI. 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. Hanging out at XAI with Elon Musk.

3:07Number one name drop of the year. All right. We've 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. I bought courtside seats for me and my friends, Ben Stiller, Timothy Chalamet, and my brother josh and we all went to the game what a squad i kid you not i'm actually friends with ben stiller i'm not with timothy chalamet and so i was like dm 'ing 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 let's go to the game and i got the courtside seats and he's like oh yeah i want to go hilarious okay knew that would be in there we got we actually got uh timothy chalamet gets double shout outs our final what also features him uh this is a story about hanging out at F1 with some notable, notable notables.

3:53Let's take a look at that one. And I'm in Miami. I got to catch a flight right after this. You're not X-speed. I'm talking in my Brooklyn high speed, but I got to go to F1. I'm here for the all-in 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 a Sergey Brin as a surprise guest. We had Tony Robbins on the program. Antonio Garostas came to talk a little bit about a little bit about Doge and what he's working on.

4:27And then who am I missing? 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 play 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 um 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.

5:10And we had a great all-in VIP party. And yeah, Travis B, two of the other besties, Chamath Freberg, Shane from Polymarket, and Timothee Chalamet and a couple of his friends. So we had a nice poker game with Timothee Chalamet. I'm still jealous. Timmy Tim is the number one name drop of the year. He got in there multiple times. It's interesting. You know, Timothee Chalamet is a social media machine. When you think about it, he's 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. He's got this ping pong table tennis movie out, Marty Supreme.

5:48And the publicity for this movie has been nonstop for like a month now. He's everywhere promoting this movie. Even on All In and This Week in Startup. So here we go. I don't, I mean, you guys tell me who wins, what was the name drop of the year in your minds? You guys pick. Lon, you go first. I'll go second. 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, Timothy Chalamet. Yeah, that was a big drop. That's a deluxe name drop right there. I'm going to go with courtside seats because not only did Jason manage to name drop a lot in there, he also managed to get in a massive dig at Detroit.

6:30Tickets there are like$4. Fair. I appreciate the high-mindedness and the low-mindedness at the same time. It's literally a jump ball here. I guess I have to be the tiebreaker. I'll go with F1. I'll go with F1. Only because having a Sergey Brin, Tony Robbins drop, complimenting and bookending a Timothee Chalamet is like, that's a J-Cal, like six or seven 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. All right. Up next, we got the biggest trend of 2025.

7:08And I've got 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 &A. A huge theme for the year 2025. Let's take a look at a sample clip. if we had more M &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.

7:41So the wrath of Lena Kahn ending and the Trump M &A bonanza begins, which I would just say is a Republican M &A bonanza and hopefully less regulation on M &A. We need to let M &A rip or else we will not have risk capital at work. Let it rip, president jd lambs i mean trump so that was march that was may 12th of this year a theme that continued throughout the rest of the year 2025 up next to the second major trend of 2025 ai job displacement uh and here's a clip from june with jason predicting a youth unemployment crisis that may in fact already be upon us let's take a look we're gonna 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 uh to create jobs and that's going to be very interesting i think very interesting moment in time where you know group of five ten people like when you graduated from college or i did.

8:48When I graduated, there weren't a lot of jobs in 94, 92, 93. We're coming out of like, um, 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. Yeah. So that means we're looking at job destruction now from two different perspectives, because we've 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.

9:28That's worrying. And that's happening to White Collar too. So we've seen in big tech that they're like, yeah, we're not going to hire young people because 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 five years. If you're selling a business-to-business product, you're looking to reach professional customers who are doing business. And the question you have to ask yourself is, where do those business leaders spend their time?

10:04And 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.

10:41And 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 slash This Week in Startups to claim your credit. Well, yep. Guys, I think that's coming to be pretty darn true. But Lon, what is our third trend for the year? 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 become the world's greatest product. I believe Optimus is going to be the greatest product ever created by humanity, including the wheel in this, obviously.

11:29It 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 that used to make rice cookers and hot blankets, heating blankets. I think the first product was a rice cooker and a heating blanket. What did you think it was, the Walkman? Well, I was just thinking back to like the 90s and I was like, people, I think of the Walkman. Yeah, I realized while I was bantering that I was off by a couple of decades. Anyways, keep going, rice cookers, blankets, fantastic. This could be, like, we could be sitting here thinking like, all these incredible cars, EV, revolution, self-driving, all a footnote.

11:59These 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. A bold prediction. Top trend here. Long, why don't I go first this time in the spirit of fairness? Do it. I think no more jobs is the most important trend of the year. Even though M &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. See, I'm going to counter you. I think humanoid robots.

12:29We actually, for All In, a few weeks ago, we were talking about, because 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 One X. 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.

13:02But this is the trend of 2020-25. How do we frame it? The twisty award title. The twisty. This is the biggest trend of 2025. Ah, see, that's interesting because it is of 2025. And I, so my choices are M &A returns, Lena Khan is gone, AI job displacement, the rise of the humanoid robot. Okay, I have to go with because of the twisty title, that M &A is the one that most acutely landed in 2025. Fair enough. Job displacement feels like it's coming next year. 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 &A deals.

13:52I got to go M &A. So wait, do we each pick a different one? Yeah, so it's now tied for each of the ones. We each picked a different one, but I think it's your show. You're the host. All right, great. We'll go with mine. End of Lena Khan and I'll stop talking about it. Everybody's upset that I keep talking about it. I will not bring, I will not say Lena Khan in the wrath of Lena Khan in 26. It'll just be Trump's M &A train. The Trump, the M &A Trump train. All aboard. Boop, boop. Can we do a polymarket on how long it takes Jason to say the wrath of Lena Khan in the show in 26? I won't do it. I'll put all my money behind it and not do it.

14:29Up next, the category is the best Jason anecdote of 2025. I rounded up some of our favorite Jason story. Sometimes Jason likes to go on a little tangent, tell us a little story from his exciting life in technology. Guilty as charged. 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. 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 oh yes this is this is true it's a little dark i had somebody else 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 dollars 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 They've reversed and searched it and they tweeted it.

15:26This is on July 4th weekend. I say to the guy, I look the guy up, I Google search him because I have security protocols. So now I gotta get the security company involved to find out if this person's gonna jump my fence. Right? Okay. You know, I have security, I have guns, I got cameras, I got alarms, I have security details. I mean, I got it all. I don't talk about it, I'll talk about it here for Bruce. I finally got on LinkedIn. I looked at the company, hey, that company looks very familiar to me. I clicked the company. I know the CEO who we worked for. I screenshot it. Checkmate. I send it to him and I say, hey, dipshit, first of all, happy Independence Day.

15:53Number two, your boss and I had drinks at this conference, played cards, yada, yada. And I'm about to email them what you just did. And 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. I said, hey, dum-dum, 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's your kid? This is four weeks.

16:17I 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 me 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's seat. Yeah, they're a donkey, you think? And I said, considerate lesson learned, water on the bridge. I wish you great success with your four-year-old. I encourage you to have more kids that are a blessing. And next time I see your boss, I'll tell them what an amazing individual you are.

16:48And I will never mention the signal. Wife responds back. Thank you, Jacob. It's a true story and pretty crazy. People have too much time on their hands, I think is 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. I like that at a certain point in a man's life, the wife neatly just takes over the mom role. That would be if a child did something, you'd be like, 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.

17:18Next 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. 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 April of this year. Well, you know, I read about Brown. And I said, you know, they let you make your own degree. You can kind of roll your own concepts. So my concept is psychology and like human behavior plus computers.

17:49Cause I, you know, I'm into computers and online services specifically. He 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 I don't want to be a cop. I almost was one. And he said, yeah, do that. Like it's better. Like you're not barely getting into Brooklyn college. And I got into Brooklyn college and I wound up getting into Fordham.

18:08But 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. That pissed me off so much. I was like, this guy, maybe 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. I like that story. It's a true story. It's your story. Wow. I got a crazy life. Keep going. 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 flying, including that you must never be late for the private jet.

18:37and here's why there's like two rules there's three rules of private jets none'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 um it was just 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 stand and say don't worry about it we're late we can go to another and it was like i hit massive traffic and we did have to divert from one airport to the other bummer uh 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 gonna sit first so you come in you place your bag somewhere neutral.

19:09You 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, 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're having a conversation with them or cross from them if they don't want to spread their feet out or catty corner to them. Or you sit at the table back there if they want to have privacy. So you just say, hey, where do you want me to sit? You got a preference? You just say them. Yeah, because they're paying for it.

19:28Well, yes, it's like being in somebody's car, you know, or their house. 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 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 number one best way to start a website for your company.

19:57And 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 design an entirely customizable website that perfectly suits your aesthetic, your voice, your personality.

20:30Support Twist's longest running sponsor by going to squarespace.com slash twist for a free trial. And when you're ready to launch, go to squarespace.com slash 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. Now everyone knows. You know, the next time you're on private jet, thinking about where the principal sits. Clip that for your prince riding a private jet for the first time. So those are our three. Now it's time for everybody to pick their - You guys pick. You guys pick.

21:02I mean, I think the answer is Jason getting doxxed and responding in kind. For sure, that's my pick. The reason why I like that story, Lon, is because at the end of it, he says, we're going to put water under the bridge. I'm not going to blow up your life. I thought that was quite good of him. Of course. I don't want to blow up anybody's life. But the best story is clearly the private jet story, because 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.

21:31I took notes. I took diligent notes on that because I know one day it's going to come in hand. One day he'll be on my jet. When Jason does eventually get a jet, I'm going to be like, hey, we've been friends for so long. I almost did in 25. Who knows what will happen in 26. We'll see. hope springs the eternal. No, I could get it. I just keep pushing it off. I'm going to monitor whether he's reading the paper or whether he seems like he wants to talk now. I know. I'm not. Watch for social cues. When we're on the J. Cal plane, I'm going to be, I'm going to feed up on the couch. I'm going to take the good seat.

22:05I'm going to like leave a mess in the kitchen. Well, I'll leave over and tell Marcus what, yes, Marcus, which one was his favorite story? Marcus, which one is your, of those three, which was your favorite? Marcus says doxing. Marcus is with me. Okay, doxing it is. He's a tiebreaker. That's a classic. That's a classic. And it's very much like a J. Cal story. That's exactly how he handles those kinds of situations. Yes. Hey, dum-dum. Talk to your wife. I like hey, dum-dum. That's good. Up next, I've got four nominees. This category was so packed. Now I had to go beyond three. The best guest of 2025.

22:38Huge category here. Maybe the biggest of all. Our first nominee, this was from an all-star episode. we had Gilly Renan 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. First of all, the sham of the scam that is called venture capital. Let's take a look at this. We get paid, 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 to keep somewhere between 20 and 30%. You wonder why the balance between greed and fear always lean towards greed.

23:16A 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 proclivity to lean in because of the compensation structure. Point one. Point two, we have seen every generation. And by the way, I know my partners are 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. Love what a guest says. They shouldn't say it, but they're old, so they're going to go for it.

Read the full transcript

23:42That to me is the best moment. Yeah, I shouldn't say this. That's how you know it's going to be something good. Up next, from early in the year, we had an online expert in crypto, Coffeezilla, to discuss the meme coin explosion. I thought 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. I also think there's an opportunity to demarcate out, even if you're saying, by the way, I hate meme coins. I think if you want to do it, that's fine, but I just think it leads to these kinds of bad incentives.

24:14but 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. They said they were gonna do it, they locked it up, right? 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 stuff should still be illegal and prosecuted heavily. What I wanna see, if it was my dream, is that, look, even if they wanna be like pro-crypto innovation, right?

24:42Meaning 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 throw out the guys 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 fraud. 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.

25:05So 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. 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 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 and 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 us humans we were kind of the bottleneck for the for software and that's typically what the product manager does and now now i think it's more like an ai builder or that is really good at understanding and testing with users so that's going to remain and we're like at 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 launch your lovable apps and get feedback from users.

26:07And then I think what you're going to see is that single people, companies, where the founder has great product taste, we'll be like single person SaaS companies and be able to launch and market them just thanks to the wisdom of the crowds figuring out where the best high value SaaS products are. And that's launching tomorrow. Yeah, that's launching tomorrow. Well, break a little news here on the show, 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.

26:36Oh. Double header of all-star guests. We had Rahul Vora of Superhuman, now, of course, of Grammarly, which has taken on the name of Superhuman, and Vlad Tenev of Robin Hood. Here they both are together discussing their approaches to great design. 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 Robin Hood Robin Hood, how have you taught those pieces to people?

27:13This is such a good question. Yeah. Professional development. Yeah. I mean, 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 the first go around, we hired some professional managers that 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 in leadership positions. And then 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.

27:50And meetings are not just forums where we review the work, but we actually do design in meetings and actually change things. There you go. Four amazing guest segments. What's your pleasure, guys? What did you think was the best? 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 going to go Raul, Vlad. But what do you got, Alex? You know, I'm going to take Doug. Doug was good. Yeah. Oh, God. And the reason why is it was like, like we're almost like a reluctant knowledge because I feel like what Raul and Vlad were talking about, very interesting, but very much almost in their favor to say.

28:26Whereas I feel like Doug is kind of like walking and throwing hand grenades behind him, which makes him extra special to me. Okay, what do you got, Lon? What do you got? Yeah, I'm gonna break the tie. I think Rahul 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 gotta give it to Doug Leone. A legend. I'm with you guys. Yeah, you guys both convinced me to change my vote. And funny. It's one of the funniest episodes of the year, for sure. He's just got a great personality and a great way of speaking.

28:57and it's a delight to listen to him. All right, I'm going to go with you guys. Doug Leone, legend. Congratulations. Up next, the best Jason rant of 2025. Lots to choose from. Let me tell you, I had, this list was 10 plus at one point and I had to winnow it down. First up, Jason got a little fired up after hearing about the r slash 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. 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, it's some crazy capitalist and they're forcing you to come to work, it's actually in your benefit.

29:40I 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. So they literally lost graduation of college or graduation of 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.

30:06We 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 Foundry 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.

30:32So 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 Puri, you know, the hosts of My First Million, which is a great podcast.

31:03I listen to every single episode. They're just awesome. So download the guide for free at clickhubspot.com slash twist one, or just find a link in the description of this show. And thanks to our friends at HubSpot for sponsoring today's episode. 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 theatrical exhibition industry. Here's Jason's thoughts on how to fix movie theater. They made skiing into a drug for a certain cohort of people where you just get that high, you want to keep doing it.

31:39Movies 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, the 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 were, and then maybe you got the Epic Pass. Maybe you go skiing for the entire day for free.

32:01People 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 going to add$2 to everything for 3D. I'm going to make you watch a movie in 3D that you never asked for 3D. Oh, I'm going to put it on IMAX. We charge another 3 bucks. So now you're getting to 16 bucks. Oh yeah, I'm going to make it a luxury theater. You're going to be able to order food to your seat. Now the 10 bucks in popcorn and drinks went to 25 bucks to chicken fingers, et cetera. I literally spend$250 when I go to the movies now. Let that sink. Five people,$250, about$50 a person.

32:22I go to an IMAX. I like the IMAX dinner. That's$18 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 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, J. Cal. I give myself a pat on the back for that one. That one definitely holds up.

32:49Holds up, for sure. This one from late July was aimed at the T 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. 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.

33:32Yep. And if that person had posted about somebody they dated who they felt was dangerous, let's say in the worst circumstance. Yep. 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. Other than that, great application, though. Right? Fantastic. Brutal. 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 a lot of problems that are going to develop.

34:08Last one on our Jason rant lineup. up uh i'll just say the title you can't trust zuck let's take a look i remember this one 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've said since the beginning, you can't trust Zuck. Zuck can't trust Zuck. Zuck should understand. He's made the wrong decision about Instagram, kids on Instagram, banning Trump from the platform.

34:51Every decision he could make, he makes the wrong decision on these social issues. Therefore, he needs an abudsman. He needs a group of people on that board or around him that's not Mark Andreessen or not Peter Thiel. I was about to say, he's got Mark right there. 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 gonna 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 gotta be zuck right because i was so fired up well no you're You win on that one because you said meta and then metastasize, which I believe is a really good play on.

35:39Yeah, I didn't catch it the first time. I didn't catch it either. It wasn't intentional. What do you think, Lon? You favor the movie one? 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 grant. And it's such a twist class. 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 to trust Facebook and Facebook. apps. That was like six months into the show. So it's a classic. Yeah. 15 years ago, I was like, listen, he's going to steal your ideas.

36:10Okay. Let's keep moving. Let's keep rolling. All right. My favorite category is up next. The most controversial moments of 2025. These are times when the show got a little spicy. Sometimes the podcast gets a little spicy. 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. Yes. John Denver was for everybody. So John Denver was for everybody. And as I always warn my friends who want to become pilots, if you've 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.

36:57It'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. Listen, sometimes just have a need for speed, Jason. No, I gotta tell you, it's so dumb. Cave diving, experimental flying, and motorcycle racing. None of that. Don't do them. Also, experimental subs, please. Let James Cameron do the submarine tech. He's the expert. That's another one.

37:27A billionaire and his son decide they're going to go on an experimental submarine. if it has experimental or test in the word. 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 points. Unless you're Tom Cruise, it's hard to argue with all of those points. RIP John Denver. What's next? 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. it here's uh here's that clip she looks terrified yeah and then when they were walking onto the space shuttle she's having second thought and then the moment they got katie perry vomiting no the moment they got back this is right when the spacecraft landed katie perry kissed the ground yes okay once again katie perry making herself the center of attention of course oh even more gail let us know that as they were attempting re-entry katie perry treated them all to a little song the best part was when we got back in our seats after zero g's katie's saying what a wonderful world.

38:26She did. Oh my God. Oh yes, yes, yes. Oh, because you're in a spacecraft, you kick it away. It's a command performance. You can't escape. Wow. I can't think of anything worse. Just let us enjoy the moment. Get out of space. 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. I mean, wow. I just want to shout out Orlando Bloom. Now we all know what this poor man has to go through. 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.

39:01Oh, it couldn't look more wang-like. There's nothing you could do to make it look more like a wang. No, it is literally designed to evoke a certain, yes, a phallic image. I mean, rockets inherently look like penises, and then this one is designed to just look like a circumcised penis. Oh, God. Very graphic. No lie in that entire clip. oh god i'm having more fun than i expected all right what's next all right up next from august uh jason responded kara swisher former former friend uh former confidant went on i guess the host of the pivot podcast now i thought 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 um 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 here i'll just call her on it 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 this might be reverse jealousy that that show is so popular um but it makes a magnitude more money than uh 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 dollars it doesn't matter and I have much more than that so I don't care about money I've never cared about money um 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.

40:38I just am 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 capitals do. They manipulate politicians. They back them with money to get the result they want. This has nothing to do with Jason Gallagher. This has to do with how the world has always worked.

41:13After$10 million, guys, it doesn't matter, clearly. It does. What you got that much? Take it from me. Between that and the private jet stuff, I really think that I'm learning a lot today. I'm growing as a man. 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. If I was a developer of any kind, I would never work with Sam Altman and OpenAI.

41:50Let 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 isn't 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.

42:26Microsoft had a platform and operating system. They let people build Lotus 1-2-3. Then they did Microsoft Excel. They let people build of product called WordPerfect and WordStar, and then they built Microsoft Word. Now, wait, what category are we in again? Most controversial moments. Most controversial moments. 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. 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.

43:03And 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? That was definitely the one the public found most controversial. To me personally, I got to 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 spicy. It got pretty personal. Yeah. I think Jason went too far on the Orlando Bloom comment. Also, he's out of date. 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 language on the show.

43:44What do you got for most controversial? I mean, it's got to be the Katy Perry thing. Katy Perry wins. There it is. Congrats to Katy Perry. 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 question. I would say in an elevator, I would be pretty counting the floors. Two more categories left. We're almost out of here. Almost out of here for the twisties. We're getting there. We're getting there. 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.

44:14So up next, we've got a first ever award this year, the Disgraciad of the Year. Jason 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 disgrace-y-od. This is in episode 2162 back in 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.

44:52Just how disgrace-y-od this company is. It's disappointing. That's how I feel. I feel disappointed. When we got the iPad, when we got the iPhone, you were looking forward to a lifetime of exciting Apple products. You were gonna, every five years, there was gonna be some new, amazing innovation. And it has not been realized, that vision. 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. We waited in line overnight, 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.

45:27And I think once we got through the pipeline of whatever Steve Jobs had thought of, there was 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 I might've said that. And it was like - Disgross the odd 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. Which is Vail Resorts. The company, the stock ticker is MTN. Oh, MTN. I looked that up before. MTN. And let's see, five years. I'm looking at the five-year stock. It's down.

46:08Yeah, if 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. Correct. 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 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. Disgraciad, as we say in Brooklyn, Disgraciad.com. I own the domain Disgraciad and I am going to redirect it.

46:45I don't even know how to spell that word, but you should redirect it to Vale's IR page. It's D-I-S-G-R-A-Z-I-A-D, as I have learned this year. That's how you spell Disgratziad. Disgratziad.com. And now it's infected all in. And now, yeah, it's everywhere. Timothee Chalamet will be doing Disgratziad soon. Next to Phil Helme is on the poker table. Sorry, Lon. Go for it. Up next, here's a clip from June. The only politician to make the Disgratziad list, L.A. Mayor Karen Bass. Here's what Jason had to say. For people who just landowners, I heard you mention they were going after ranch owners, et cetera, who have to deal with fires too.

47:26And by the way, I was spending time with Rick Caruso, who ran for mayor, lost to Karen Bass. In LA. In LA. Karen Bass, complete incompetence, disgraziade, like the worst leader you could ever have during a crisis. As we saw her 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. The African nation of Ghana. That's where she was while LA was burning. Finally, from October 1st, an app has made the actual disgraciated list. It's Bank of America's mobile interface.

48:02Let's take a look at this clip. There's some poor team who has to relive their trauma. All right, here we go. 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 when compared to using venmo or using robin hood it's 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 like literally just go find a design firm to tell you what to do and just spend to 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 taste say this one yeah is all mobile banks i think would be up for that disgrazia but i'm glad we neared single out one of them who's yours alex who's your disgrazia i'm gonna go with with your gut yeah i'm gonna go with apple uh not because it was the best like angry riff on why they're bad, but just because I really fundamentally agree with it.

49:17Like I really think that Apple is a company whose products I use, but I find interchangeable today. And that loss of magic is a crisis. Blond? Yeah, I totally agree. If we're going on who deserves the disgraciate 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? I air buds are the only ones I can think of air pods, not air. You want to do a way in. I got to go Apple. I think it's the most logical of all the discrepancy. 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.

49:59It'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. But even that, it's not an original idea. They already did the Air. Like we already got the thin laptop and the thin iPad. They're just doing that again for the phone. Yep, should have made a cheaper Vision Pro to begin with, y 'all. Got some market share. 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.

50:34Make it twice as big and give me three times the battery life and I'll buy four. Yeah, 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. I mean, it feels nice in your hand. That's all I'll say. It does feel nice in your hand. 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 uh he's got a pass to call jason the c word but he doesn't it's true that c word let's take a look 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 in i'm zooming in from england i'm in english right now i have the uk pass i'm australian I'm allowed to say that Jason is capacious.

51:34You're correct. Yes, you did say capacious multiple times. I took it the right way. I took it in the spirit. It was intended. We have fun here at Twist, ladies and gentlemen. We have fun. From the same episode, here is another Alex dad joke from the same episode. The same episode. Same episode. Back to back dad jokes. This is around the time my second child turned one, so I must have really been on one. All right, here we go. Into these dad jokes. Here we go. To find stuff. If only I knew a guy 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.

52:03I mean, making raunchy stoner comedy seems like a genre that, you know, you could do some real damage. That's like my personality after 8 p.m., so I'm totally here for it. That was a dad joke from Alex. Sorry. I heard that. No, don't apologize. We love it. I don't even mean to. Anyways, keep going. There it is. Falling, falling right into them. This is a very recent one from December 15th. Only last week we got, we snuck it in under the wire. This is Alex on Lightspeed Ventures and their latest fund. Let's take a look. Oh, yeah. Right. All right. Here we go. 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.

52:41Shout out to everyone at Lightspeed. Please take everyone out to lunch because you have enough cash for that. Yeah, absolutely. And that immediately goes into the Alex's Best Dad Jokes of the Year. Thank you. Well, I'm running out of time. I mean, I got to squeeze them in, man. Makes them easier to find when I tag them. Right, Lon? I tag them like that. Makes them easier to find at the end of the year. They come right up in notebook when you put that. But I will say, this category, I did a pretty exhaustive search. I looked even for ones that didn't come up in the notebook LM deep dive. Hard to find them.

53:14You know what I wanted for Christmas? I wanted to force Lon to endure my crappy humor for hours on end. So I got it. We had the whole team. We broke it up into fiscal quarters. but we had the whole team rewatch almost every episode. I did Q1. We had Jacob doing Q2. Marcus doing Q3. We really exhaustively searched. We didn't want to leave anything out. So finally, from April 16th, not so much a dad joke. We all, the entire team, just really liked the way Alex said, yes, sir, in this clip. This is just hazy. A quick look from April 16th. I am so excited today because I know that Alex's grin can mean only one thing.

53:55Somebody filed to go public. Who was it? Yes, sir. It's Figma. Yes, sir. Yes, sir. Yes, sir. It's Figma. That was my honest feeling. I was so excited. What do you got, Lon? You're such a student of the comedic arts. I mean, we all, I have been saying yes, sir, like that all week. So I think that has my... I'm going yes, sir. I think that's my history. No, the correct one was capacious, clearly. What a good year, guys. We did like 150 some episodes. We covered so much fricking ground. The world changed so much. And we even mostly got along. Yeah, absolutely. Mostly. There's your dad joke early for next year.

54:35I got, I got one more clip there. Well, we'll exit on. All right. We've got 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 of 2025. We have this expression here in Texas, as the crow flies. Yeah. I don't know if you've heard this. It's also in Tennessee. I think it's in Tennessee. Groceries, that old-fashioned term, groceries. But as the...

55:11It'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. Like simple old-fashioned word, groceries. Groceries. Made me chuckle, so I wanted to throw it. How many Trump impressions were there to choose from? Because I feel like it happens like once a month at least. We had four or five in the category, and I just thought, you know what? 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. Oh, I'm happy for us. Happy end of the year, guys.

55:40Happy New Year to everyone listening. We're back next year. And we'll see you in the new year on Twist. Bye-bye.

From the publisher

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


*


Subscribe to the TWiST500 newsletter: https://ticker.thisweekinstartups.com


Check out the TWIST500: https://www.twist500.com


Subscribe to This Week in Startups on Apple: https://rb.gy/v19fcp


*


Follow Lon:


X: https://x.com/lons


*


Follow Alex:


X: https://x.com/alex


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


*


Follow Jason:


X: https://twitter.com/Jason


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


*


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

More from This Week in Startups

All 653 episodes
THE 2025 TWISTY AWARDS! Biggest Trends, Best Guests, Top Name Drops, and moreThis Week in Startups · 56 min
Listen in VO